Chapter 1 Salon Trouble
I'm Andrea (Andy) Miles, and it was the summer after my freshman year of high school. Maybe I was paranoid, but in the past year, a tech billionaire from Silicon Valley and various other people had made my life difficult. They took special delight in humiliating me, and had used some "gentle persuasion" to convince me to get my hair cut while in bondage.
My hairdresser at the salon isn't judgmental, and she was happy to comply with my bizarre request to be tied up when I had my hair done. Karen is actually very friendly, and also very chatty. I go to the salon every two weeks just to have my bangs trimmed, but for some reason, she always has to wash my hair first (with me tied up) and then go through some elaborate ritual of brushing out my hair, and then finally depositing me in a chair under a hair dryer. So a trim that should take five minutes always turns into an hour-long stay at the salon, with her chatting at me for most of it.
Over the course of several visits, she hadn't really gotten much out of me, other than I liked to play the part of a damsel in distress, and it was fun for me to be tied up. Since I wasn't very talkative anyway, she started gagging me after she had finished trimming my hair. She even gave me a pink scarf to wear to the salon, because she thought it made a very pretty cleave gag.
I was nervous the first couple of times she tied me up, but she didn't take advantage of me, and she always made my appointment the last one of the day, so there wouldn't be any other customers around. After a while, I got used to being tied up and helpless while having my hair done, and I really did start to feel comfortable with it. In fact I enjoyed it so much that I actually started wearing the penis chastity that I hated so much, just so my dick wouldn't be bulging up through my panties! Although it was out in public, I started thinking of the salon as a safe place where I could enjoy being humiliated, because no harm would come of it. As usual, I was wrong, but we'll get to that.
My prep school was actually a boarding school, but last year I had lived at home, and attended school as a day student. But now that I was more familiar and comfortable with the school, I was going to live on campus for my sophomore year. Caroline, the younger sister of my swimming rival Nigel from Australia, is my girlfriend, and would be my roommate. Both Nigel and their parents weren't sure it was a good idea for her to live with someone who was, as they put it, "not really a girl." But she pointed out to them that we had already lived together for a year at my estate, and nothing had happened. Actually, A LOT had happened, but nothing sexual with her, so they gave in and let her live with me on campus.
In September, Nigel and Caroline returned from Australia. He went to live on campus at the university, and Caroline and I moved into our room at prep school. My estate would still be maintained by Bob and Jenny, the young couple who were very discreet at ignoring Caroline and me unless they heard blood-curdling screams.
Caroline and I were on the swim team, so we got up early every morning to swim laps and have Coach Collins scream at all of us, the way coaches do. But we had a very strong swim team, so he was less unhappy this year. Me being the star of our swim team meant that the faculty, or at least the swimming coach, had a vested interest in keeping me alive.
It was Friday of my first week at school when I met a couple of girls walking across the campus. The blonde was named Summer, the redhead was Kaitlin, and like everyone else at this school, they were taller than me. After they introduced themselves, Summer held out her phone and said, "Andrea, maybe you can explain this?"
It was a picture of me at the salon. My hands were tied behind my back, and I had a big grin on my face. I stared at the screen, my eyes wide, and just said, "Uh
"
"Feel free to use words," Summer said.
"I
I..uh," I said, trying to think of some way to explain this.
"It's a funny thing. I was in town, just window shopping when I walked by the salon, and look what I saw. A cute little girl having her hair done," she said, and then brought up another picture.
It was another picture of me tied up, only now gagged with a pink scarf. Then she showed me another picture of me under a hair dryer, still tied up and gagged. Now I could feel myself blushing.
"Uh, well you see, Karen and I are friends," I said.
"And you're into bondage?" Kaitlin said.
"Um, kind of," I mumbled, and I was sure I was turning bright red.
"Don't worry, sweetie, so are we," Summer said, resting a hand on my shoulder. "Why don't you stop by our room tonight around seven, and we can have some fun?"
"I
I don't know
" I said.
"Don't worry, we won't hurt you," Kaitlin said. "We're not going to injure our school's best swimmer. We're just going to have some fun together, just us
girls!"
They gave me their room number, promised me it would just be the two of them, and told me not to disappoint them. So I agreed to pay them a visit, and they agreed not to share those photos with anyone else. I was starting to think maybe living on campus wasn't such a good idea after all.
That evening, I went over to see Summer and Kaitlin. I was still wearing the same clothes, a white blouse, blue skirt and black boots. When I showed up at their dorm room, both of the girls were wearing T-shirts and blue jeans. They invited me to sit in a chair, and both of them sat on the bed across from me.
"Nice outfit, Andrea," Summer said. "You look cute in it."
"Um, thanks," I said nervously. I wasn't sure where this was going.
"You've been at this school for a whole year, and it seems like you always wear skirts. I don't think we've ever seen you wear pants. Not even in the winter, when it's cold," Kaitlin said.
"Oh yeah," I said. "I always dress like a girl now. I'm just trying to fit in."
"Maybe you haven't noticed, but most of the girls here wear jeans like us," Summer said. "If you wanted to fit in, you'd be wearing shorts or pants."
"I didn't think of that," I said. "I'm a trans-girl, so I was just trying to dress like a girl."
"All right, trans-girl," Kaitlin said. "So what kind of bondage are you into? Do you like ropes? Or do you prefer to be chained up?"
"Um, well, I'm used to ropes, I mean if they aren't too tight," I said. "I just don't want my circulation getting cut off."
"Don't worry, sweetie," Kaitlin said. "We have plenty of ropes, and we won't even leave any marks!"
As the girls got up, I said, "I'm a swimmer, and I have to go out to the pool half-naked every day, so if I have marks on me anywhere, the coach and everyone else will see them."
"Don't worry about a thing," Summer said, walking around and drawing my arms behind me. "We didn't bring you here to hurt you!"
Then I felt ropes tying my wrists together. I half-expected this, but it still made me nervous. "So then what did you bring me here for?" I asked.
As Kaitlin tied my ankles together, Summer said, "To get to know you better! We want to know all about you!"
Then they picked me up out of the chair and laid me on the carpeted floor. "Um, OK, what do you want to know?"
Both girls knelt beside me. "So how long have you been into bondage?" Kaitlin asked.
I thought about my trip to Australia. "About two, maybe three years," I said.
"And how long have you known you wanted to be a girl?" Summer asked.
"Well, ever since I was little, I guess," I said. "But I wasn't sure until about three years ago."
"Oh, so then you got into bondage about the same time you knew you wanted to be a girl?" she asked.
In fact, I had gotten into bondage and become a girl at the exact same time, but I wasn't going to tell them about all of that. "Yeah, I guess so," I said.
"You know, Andrea," Kaitlin said, "that doesn't quite ring true."
"What
what do you mean?" I asked.
"The way you always dress up, the way your hair is so pretty, and your bright red nails," she said. "And you like being tied up. I think it all adds up to you being a submissive little sissy boy!"
This was hitting a little too close to home for me, and I wasn't prepared for it. "I
uh
I-" I stammered.
"It all makes sense," Summer said. "You're a pretty little sissy who likes to play dress up, and you like being tied up and gagged. It all fits together, doesn't it?"
"Do you think I got these breasts just because I like to play dress up?" I asked.
Kaitlin caressed one of my breasts, and said, "Wow, those ARE impressive! And they feel so real! You really went to a lot of trouble to look like a girl, didn't you?"
"That's what I'm trying to tell you!" I said.
"Well then, let's look between your legs and see how you're fixed down there!" she said.
"Now wait a minute!" I said, but then a red ball was forced against my teeth, and into my mouth. A moment later, the ball gag was tied off behind my neck.
"It won't hurt to take a peek, now will it, Andrea?" Summer said.
I just groaned into the gag as the girls lifted my skirt, pulled my panties down, and pried my knees apart.
"Andrea, it looks like you aren't really a girl after all, now are you?" Kaitlin said.
I just lay there flat on my back as the girls pushed my knees further apart, and inspected my genitals.
"It's kind of small," Summer said. "I wonder if it stretches?"
I craned my neck to try to look up, and just then she grabbed my dick, and pulled on it, and not in a good way. "Stop that!" I tried to shout into the gag.
"I think that upset her," Kaitlin said. "Or upset him, I'm not sure now."
Summer let go of my dick, and said, "You know, Andrea, you really can't be a girl if you still have a penis!"
Then the two girls got up, and stood over me. I just lay there on my back, helpless and staring up at them.
"What do you want to do with sissy boy?" Kaitlin asked.
"He doesn't look happy," Summer said, looking down at me. "He must not be tied up enough. I'll get some more ropes."
As I shook my head, Kaitlin said, "Good idea. After all, the little sissy did come here for bondage!"
I groaned into the gag, and briefly struggled against the ropes, but it was hopeless.
"Oh look, sissy boy is trying to struggle!" Kaitlin said. "So he definitely needs more ropes!"
I shook my head and tried to kick out at her with my bound legs.
"It looks like he's being difficult," Summer said. "I think you need to give him a spanking!"
Kaitlin stood over me and asked, "Is that right, Andrea? Do you need a spanking?"
I shook my head again, but she just picked me up, sat in the chair and threw me across her lap.
"Time to teach Andrea to be a good little girl," Summer said. "Or boy. Or whatever it thinks it is."
"Right. Little Andrea needs to learn a lesson." Kaitlin said. Then she pulled up my skirt, and slapped my naked bottom.
I groaned when I heard the slap, but it didn't really hurt. Compared to the times I had been beaten, caned, and whipped, this was nothing. But I was supposed to be safe at this school, and now I was being bullied by girls.
She slapped me four or five more times, and said, "Andrea, I'm really surprised at how nice and round your butt is. The rest of your body is so lean, do you have implants here, too?"
I just groaned again, and nodded my head.
"You can take a good look later," Summer said. "Time for me to tie up the little sissy!"
They set me on the carpet again, and I felt ropes winding around my elbows until they were tied together.
"Flexible, aren't you?" she remarked.
I just nodded again.
"I can see we'll have a lot of fun together," she said, as she bound my legs together, just above the knees. Then she turned me over on my stomach, and drew my ankles up and tied them off in a tight hogtie. None of the ropes were really tight, but I could barely move an inch.
Then Kaitlin pulled me up on my knees, and said, "Andrea, whatever you are, you make a very pretty little slave! Would you like to be our slave?"
I just looked up at her and shook my head.
Then she went and got a hairbrush. I winced as I expected her to hit me with it, but instead she started brushing out my long hair. "Your hair is so pretty. You'd make a very pretty slave. We could put a collar around your neck, with your name on it!"
"That's a good idea," Summer said. "I think it would be fun to have this little cutie on a leash, kneeling in front of us."
"So tell me, Andrea, do you have a boyfriend?" Kaitlin asked.
I shook my head and tried to tell her I had a girlfriend, but I'm sure it came out too garbled.
"Wait, it's trying to talk," Summer said, and pried the ball gag out of my mouth, letting it dangle about my neck.
I worked the stiffness out of my mouth, and said, "No, I like girls."
"Oh, so would you like to go out with one of us?" Kaitlin asked.
"Um, I already have a girlfriend," I said.
"Really? Sissy boy has a girlfriend? Anyone we know?" she asked.
"My roommate, Caroline," I said. "She's on the swim team with me."
"The Australian girl?" Summer asked. "I'd seen the two of you together last year, but I wouldn't have guessed she would be into you."
"Well, she is," I said. "We've been together for more than a year."
"So is she into bondage, too?" Kaitlin asked.
"Yes
well, no," I said. "I mean, she doesn't get tied up, but she'll tie me up."
"So then you're the submissive that always gets tied up, and she's the dominant one in the relationship," she said.
"That's pretty much it," I said.
"Then when you're together with her, you do play the part of a submissive sissy, don't you?" Summer asked.
"Sometimes, I mean it depends on what I'm wearing," I said.
"All right, then you're supposed to be a girl at school," Kaitlin said. "But when you're in bondage, you can still be a sissy boy, right?"
"Something like that, yeah," I said.
"Then I've got another gag for you to try on," she said.
"Another one? What's that-" I said, and then saw a penis gag pointing at my mouth.
"Sissy boys like these!" she said.
"What
what is that?" I asked, as she slid it into my mouth.
"Little sissy boy's never seen a penis gag?" Summer asked. "You must really be an amateur at bondage. But there's a lot we can teach you!"
As she tied the gag in place, I could only think it was these girls who were the amateurs. I had been taken advantage of, and been victimized by professional bondage experts over and over for the past few years, but I wasn't going to tell them that. I just groaned into the gag.
"Don't you like your new gag?" Kaitlin asked. "I thought sissies liked sucking cock!"
"Maybe Andrea wants a real cock," Summer said. "We should call one of the guys over. Then sissy boy can see what it's like to have a real cock in his mouth!"
I shook my head as hard as I could. I had already been through that last year with those guys Bill and George.
"No, you'd rather play with girls?" Kaitlin asked. "You'd rather just stay here with us as our slave?"
I just groaned again.
"I think Andrea wants to go home," Summer said.
I looked over at her and nodded my head.
"All right, I think that's enough," she said. "For tonight! So if we let you go now, will you come back and play with us some other time?"
I nodded again.
Then the girls started untying me, and got the gag of my mouth.
"See, we told you we weren't going to hurt you," Kaitlin said.
"Yeah well, I'm never sure about this when I meet new people," I said, rubbing my wrists.
"So now you know," Summer said. "And we aren't new people any more. See ya around!"
So I left, and went back to my room to tell Caroline about these two crazy girls.
Chapter 2 Andrea On Ice
Caroline and I were on the swim team again. The team had lost two kids from last year as graduating seniors, and added two new incoming freshmen to replace them. Coach Collins told me he had warned them not to bother me, and since they were new kids anyway, they didn't want to start any trouble.
Our first swim meet was in late September, against our long time nemesis, Central High, and I was relieved that this year they came to our school. Before the swim meet, their coach took me aside and apologized for what had happened last year (me getting beat up and molested by their kids) and I told him I appreciated that. He had done the right thing, and suspended or expelled those kids.
But he paid for it at this swim meet. They had lost all of their best swimmers, and now their team was mostly freshmen and sophomores. Meanwhile, our team had improved steadily throughout last year, and this year the outcome was never in doubt. We beat Central High so badly that our coach almost looked pleased with us. He even made a new rule that if we won a swim meet, we would rewarded with a day off. No swimming practice the following Monday. A day off?? We all looked at each other, wondering if the next announcement would be that Hell just froze over.
I found out that living on campus could be fun. Sure, I had to remember to do my laundry and basic housekeeping, but I didn't have to commute back and forth to school, and I could eat with the other kids and spend more time with my friends here.
The following Friday evening, I took my weekly load of laundry down to our basement laundry room. The room was empty, or at least I thought it was, so I had my choice of washing machines. Then someone grabbed me from behind and pulled my arms behind my back. Before I could even say anything, a hand came up under my chin and squeezed my mouth shut.
"Well, well. If it isn't the little faggot who likes to swim against girls!" he said.
Then he punched me in the stomach twice, and I doubled over in agony, barely able to breathe.
"I hear you did a job on Central at the swim meet last week," he snarled. "Now we're gonna do a job on you!"
"Sam, shut up and just pop him!" the other one said.
As I tried to catch my breath, he lifted my chin, so I could see him
and then an uppercut landed on my chin. My head snapped back, and everything went black.
When I woke up, I couldn't move. My hands were tied behind my back, and my ankles were bound, too. There was a cloth tied around my mouth, and someone was carrying me over his shoulder like a sack of potatoes. All I could see was the floor, but we were indoors and the floor was made of concrete. Then he set me down on my feet, and I could see boxes stacked on wooden pallets. We were in some kind of storeroom.
I looked up at these two guys, and I recognized them. Their names were Sam and Rick, and they were two of the swimmers from Central who got expelled last year after they made me give them blow jobs.
"You ruined our lives, you little bastard, and now we're going to ruin yours!" Sam said.
They dragged me over to a large block of ice about two feet high, and Rick draped a rug over it. "This way you won't slip on the ice," he said.
He picked me up and stood me on the carpet, and as I tried to tell them to let me go, a noose swung out in front of me! I screamed into the gag, but Sam tied the noose around my neck, and tightened it to take out the slack. When the rope went taut, he said, "Have you figured it out, faggot? You're gonna stand here while the ice melts. No one's gonna come in here until business starts up on Monday morning, and you know what they're gonna find then? A dead little faggot dressed up as a girl, hanging by his neck over a wet rug!"
I looked up at the rope tied off above me, and then down at the rug I was standing on. I was going to die here, and then someone would find me, a boy, wearing a blouse, a skirt, and boots. I shook my head and tried to scream into the gag.
But he just laughed and said, "Save it, faggot! Try standing on your tiptoes, and you might live a little longer!"
Then they both started laughing, and walked out, leaving me strung up on a block of ice. I struggled against the ropes, but I couldn't get any slack on my wrists, and now there was a puddle forming on the floor in front of me. The ice was already starting to melt.
Chapter 3 What Kind Of Reswcue Is This?
The ice kept melting, and the puddle on the floor grew larger. The noose was taut around my neck, and I was standing on my tiptoes. I don't know how much time had passed since they left me here, but I didn't have a lot of time left. Then I heard a woman's voice.
"Andrea, this is a fine mess you've gotten yourself into!"
I looked over to the right, and there was a woman wearing a bandanna over her face. I didn't know or care how she found me. "Help!" I tried to say.
She held up one finger and said, "Hold that thought! I need to make a phone call."
I just whimpered and tried to suck air through the gag with the noose tight around my neck, as she wandered around the room whispering into her phone.
She finally returned and said, "Mr. Silvers has an offer for you. He would like the pleasure of your company on his yacht this weekend."
"Yes!" I tried to mumble into the gag.
"What's that?" she said, cupping her hand around her ear. "Andrea, I can't hear you."
I tried to nod my head but that only seemed to make the noose even tighter. I just tried to scream, "Yes!"
Then she went on, "You understand, it's not just this weekend. He would like to see you on his yacht one weekend a month from now on?"
"Yes," I tried to say again.
"He is aware that you may be busy with swim meets, or schoolwork, so he is willing to be flexible. It can be any weekend of your choosing."
I tried to scream, "Yes!" as loudly as I could. "Why won't you take 'yes' for an answer?"
"All right, cut her down," she said.
Then two men wearing bandannas approached me, cut the rope and untied the noose from my neck. One of the guys threw me over his shoulder and carried me outside. They put me in the back of their van with the woman, and the two guys went up front.
As we drove off, the woman sat next to me and said, "I see you've been making friends again."
This woman just saved my life, and I should be grateful, but I still didn't know how she knew where to find me, or what she had in mind for me now, so I just groaned at her.
"First in Australia, and now here," she said. "You really seem to know how to piss people off, don't you?"
"It wasn't my fault!" I tried to say into the gag.
"You look really cute all tied up with that gag in your mouth, but I can't understand a word you're saying," she said, and pried the gag out of my mouth.
"How did you know where I was?" I asked. "Are you always watching me?"
"Yes, we are," she said. "Now aren't you going to thank me for saving your life? Again?"
She did have a point. I sighed, and said, "Thank you for saving my life. Now what are you going to do with me?"
"This weekend will be your September visit to the yacht. You're going to be the star of some videos, as usual."
"More videos," I muttered. "Don't you already have enough videos of me?"
"They can't get enough of you in Australia." she said. "They love you."
"They hate me," I said.
"Well yes, but they love to hate you. You're an underground porn star in Australia," she said. "You'd be amazed at how much people will pay for those videos of you."
I just lay there and looked straight up at the roof of the van. "I'm a porn star in Australia," I said.
"See?" she said. "And you thought you'd never amount to anything as a girl!"
After that, I just kept quiet for the rest of the ride. When we arrived at the marina, it was dark, and the place was deserted. They carried me onto the big yacht, took me down below, and then deposited me on the big canopy bed. Finally they replaced my ropes with much more comfortable leather cuffs, and left me tied up on the bed.
I don't know how long I lay there on the bed before I heard someone walk in. I looked up and saw Mr. Silvers, the tech billionaire. Just when I thought this day couldn't get any worse.
"Andrea, it's so good to see you again!" he said. "I'm glad you decided to join me here for the weekend!"
My other option had been to die by slow strangulation, but I just said, "I didn't have any plans for the weekend, anyway."
"Oh, good!" he said. "Now would you like to get down on your knees and suck my cock?"
We both knew that wasn't really a question, so I just said, "Yes, sir."
He picked me up, put me on my knees in front of him, and then unzipped his pants. I was still tied up, so I just waited for him to do whatever he wanted with me. He took a handful of my hair, pulled me up to his dick, and slid it into my mouth. He rocked me back and forth as his dick swelled in my mouth and then after a few minutes started spurting. I swallowed all of it, but I still had the salty taste in my mouth as he picked me up and laid me face up on the bed.
"I understand you've going to come and visit me one weekend every month," he said. "Or actually you're going to visit, and I'm going to come!"
I ignored his joke. "Yes, sir. But I need something from you, too."
He stood over me and smiled, and said, "Andrea, you aren't in much of a bargaining position here."
"I need some help from you," I said.
"And what would that be?" he asked. "I'm listening."
"I'm told that if you wanted, you can disappear me," I said. "So that means you can make other people disappear too, right?"
"Possibly. What did you have in mind?"
"Two boys beat me up tonight, and then strung me up and left me to die," I said.
"So I've been told," he said. "And why did they do that?"
"They were students at Central High. After we beat them at a swim meet last year, they were mad at me because they thought it was cheating for me to be swimming against girls. So their swimmers gave me a beating in the locker room, and then four of the boys made me give them blow jobs. My coach complained to their school, and those boys were expelled. So now they blame me for ruining their lives, and they tried to kill me tonight."
"I can why you'd be upset over that. So what do you want me to do?"
"If you can make people disappear, I want you to make those two boys, Rick and Sam, disappear."
He stroked his chin, and said, "Andrea, just so we understand each other, you want to put out a contract to have two boys killed, is that right?"
"They tried to kill ME first! And when they find out I'm still alive, they'll come back and finish the job!" I said. "And if they kill me, then you don't get to play with me any more!"
"You have a point," he said. "Very well. I will have this investigated, and if your story checks out, I will see what I can do."
So the good news was that I was still alive. The bad news was that I was trapped on this yacht. They had me send a text to Caroline, telling her I was spending the weekend with friends, and that I would be home Sunday evening. At least that confirmed that they planned to let me go home on Sunday.
But I spent the next two days making videos for them. They had some very pretty costumes for me to wear. In one video I was a cute little cheerleader who wanted to give blow jobs to an entire football team. In another video I was barely dressed in a harem girl outfit, on my knees for the Sultan and all of his men. In still another video I was dressed as a nurse, who had the uncanny ability to take a patient's temperature by placing his dick in my mouth. I'm still not sure how that was supposed to work.
At least they didn't make me eat Vegemite. They must have been happy with the videos because they gave me real food. Pizza, cheeseburgers, spaghetti, and even some ice cream.
Sunday night, Silvers told me he was very happy with the videos they had made.
"Sir, I've already made so many videos. Why do you need more of them?"
"We've already told you, it's the Australians who want them. They can't get enough of you!"
"But you're already a billionaire! How much money can you make selling videos?"
"It's not the money," he said. "I have business relationships in Australia, and this is what my business contacts want."
"They want videos of me?"
"Actually, what they want more than anything is a personal appearance," he said.
"A personal appearance?" I asked, and then my eyes went wide. "They want me to go to Australia??"
"Oh, they'd love to get their hands on you!," he said. "You have no idea what they'd like to do to you!"
A shiver went down my spine. "But
but you aren't going to send me to Australia, are you?"
He shrugged. "Everything is negotiable. After all, business is business."
I shook my head. "Please, I don't want to go to Australia again!" I begged. "Please don't send me there!"
"Relax, Andrea. Just be a good little girl, and do as you're told. All you have to do is come back here one weekend a month."
"And I don't have to go to Australia?" I asked.
He nodded. "So for you," he said, "going down isn't nearly as bad as going down under, is it?"
That night, one of Silvers' henchmen took me back to the campus, and dropped me off near my dorm. I just told Caroline I spent the weekend with the people who wrote the magazine article about me, which was basically the truth.
Chapter 4 Splish, Splash
A few days later, I received a text message requesting my presence at the yacht for the weekend. The month of October had just started, so I just assumed I was getting my October visit out of the way early, and I told Caroline I would be gone for the weekend.
Friday night, my self-driving car parked at the marina, and I walked up to the big yacht. It was kind of depressing that the security guard didn't even bother to question me. He knew who I was, he knew what I was here for, and just stepped aside for me.
After I got on board, the yacht got under way, and they had me dress up in a bunny outfit, all in pink. I wore a leotard that covered my breasts from the nipples down, and barely reached down to my butt, which had a white cotton tail on it. I wore fishnet stockings and high heels. My hairband had a big pair of floppy bunny ears. I had a pink collar around my neck, with a bow tie attached to it. I looked like a Playboy bunny, all dressed in pink.
Their hair and makeup women went to work on me, my long hair was all brushed out, and I wore bright red lipstick. I thought we were going to make a video, but the magazine editor Marge Watkins told me to come up on deck with her. I followed her upstairs, and we walked out onto the open deck.
By now we were out on the open ocean, and it was nice up here. The ocean was calm, the salt air smelled nice, and the sky was full of stars. I thought it must be nice to live like this, except I was here on this wonderful yacht to be abused and humiliated for the pleasure of others.
"Andrea, come on over here," Silvers called to me.
I headed over to him, and then stopped dead in my tracks. Behind him, there were several men in blue uniforms, and two guys standing next to the ship's railing. Those two were naked and gagged, and their faces were red and swollen, as if they were beaten and crying. Their hands were tied behind their backs, and each of them had a cinder block tied to his ankles.
"What
what's going on?" I asked.
"Andrea, are these the two who beat you, strung you up, and left you to die?"
My eyes went wide as I recognized Sam and Rick, the kids who had tried to kill me. I nodded my head, and finally found my voice. "Yes, sir."
"Do you have anything you'd like to say to them?" he asked me.
I shook my head, hardly believing what I was seeing. "No, sir," I said.
"All right then, you can go," he said. "You have a video to make."
"Yes, sir," I said. I turned to leave, and Watkins walked with me.
Then I heard a loud splash, and then another one. I turned to look back, and the men were standing next to the railing, but the boys were gone. I rushed over to the side of the railing, and looked down, but all I saw were lots of bubbles in the dark water.
"Andrea, is there something wrong?" Silvers asked me.
I shook my head. "No, sir. I know nothing! I see nothing!"
"Good!" he said. "Now go make your movie!"
I plodded along, my mouth open, and went downstairs. I could hardly believe what I just saw, but they weren't kidding when they told me Silvers could make people disappear. One thing I was sure of was that I was not going to cross this man. I never wanted him getting mad at me.
We spent the next two days making videos of me being humiliated and being forced to do whatever men wanted. I did the best I could, getting down on my knees and begging men to let me suck their cocks, because the last thing I wanted was to get on the wrong side of Silvers. But all I could think was that I had killed those two guys. I wasn't the one who tied them up and threw them overboard, but I was the one who asked Silvers to get rid of them. He wouldn't have killed them, or even known about them, if I hadn't told him about what they did to me.
Of course they had tried to kill me, but that didn't mean I could play God and have them killed. We have courts to decide on punishments when people ommit crimes. But I hadn't wanted to go to court, because it would have been embarrassing for me. Me, the kid who just dressed up like a slut and gave blow jobs all weekend, didn't want to be embarrassed, so now those two boys were dead.
By Sunday afternoon, I guess Silvers could see that my mind was somewhere else. I had just finished making a video, and was still wearing only my bra, panties, and high heels.
"Andrea, what's the matter?" he asked me.
"Sir
um
it's just that those two boys are dead, and I feel responsible," I said, staring down at my feet.
"As you should," he said. "You told me you wanted them dead."
"I know, but uh-"
As I looked up at him, he took a device out of his pocket, fiddled with it, and then I heard my voice asking him to make those boys disappear. "So tell me, Andrea, did I misunderstand you?"
Suddenly I felt very small in front of this large, powerful man. "No, sir," I said.
"I didn't think so," he said. "All right, your weekend is over. Get dressed, get something to eat, and go back to school. I'll see you next month."
"Yes, sir," I said, and just walked away.
I could barely taste my cheeseburger. I felt like they should have given me Vegemite instead. Then the ride back to school felt like it took forever. I kept thinking over and over about what I had done. It's not that I thought I was in any trouble, at least not with the police. I'm just a kid, and I don't think I could get arrested for asking him to kill those kids. But I still felt I was guilty of doing something horribly wrong. No matter how many awful things had been done to me, I could always tell myself that I was better than the people who took advantage of me. That I wasn't like them. But now all of a sudden, even that was gone. I didn't have the moral high ground any more. I was no better than the people who hurt me.
When I got back to my room, it didn't take Caroline long to ask me what was wrong. I just told her I was tired and going to take a shower and get to bed early. When she asked me what happened, I just told her I might have eaten too much, and didn't feel good. She already knew about my past, but I didn't want to involve her in my present.
The next day I went to school, and things weren't much better. While a teacher was droning on about some boring subject, my mind would wander. I would fantasize about some guys dragging me away, tying me up, and taking turns giving me the abuse I deserved. And then I'd have to put a book in my lap to keep my penis from sticking up through my skirt.
After class, I called Karen at the salon. My hair was getting in my eyes again, and she said I could come over that evening for a trim. But when I got there, I asked her to curl my bangs instead of trimming them. She did what I asked for, and I ended up tied to a chair, and gagged with a scarf, under a hair dryer with curlers in my hair to think about what I wanted to do. When my hair dried out, I went shopping for some jewelry. Bracelets and necklaces, just cheap stuff. Also I had duplicates made for the key to my penis chastity. From now on I was going to wear earrings every day, too.
So the following morning, I wore a pink dress, along with my new necklace, bracelets, and new hair. I also wore my penis chastity because the last thing I wanted was for my dick to make a tent out of my dress, or worse yet, my swimsuit.
Caroline said, "You're going to class like that?"
"Um, yeah, I thought I would try a new look. Don't you like it?"
She shrugged. "I think you look pretty," she said. "It's just that you look like a girly girl now."
"Well, maybe I'll try this for a little while," I said. I didn't want to explain to her that I felt guilty and was ashamed of my part in getting those boys killed, and dressing up like this was a humiliating form of punishment that I deserved. Of course I didn't really expect my new look would get me any abuse from the kids at school. But Caroline and I looked like an interesting couple, eating lunch together. Me in all of my finery, while she wore her usual T-shirt and bluejeans to school. Not only was she taller than me, she literally wore the pants in our relationship.
That evening I went looking for those two girls, Summer and Kaitlin. I found Kaitlin and asked her if I could come over to their room on Friday night, and she was delighted to agree. Every day that week was the same. Every morning I curled my bangs, and wore my new jewelry, earrings, a dress, high heels and the penis chastity to school every day.
Thursday evening, I saw on the news that two boys, Sam and Rick, had gone missing, and I winced and shook my head. Of course they weren't really missing. I didn't know exactly where they were, but it was somewhere offshore, at the bottom of the ocean.
Friday night, I went to see the girls. When I showed up at their door in a white dress, Summer said, "don't you look pretty! Come on in!"
"See, didn't I tell you our little cutie had a new hairstyle?" Kaitlin said. "And she's wearing some bling, too!"
"Yeah, what's up with the new look, Andrea?" Summer asked.
"I want you to tie me up again, and I want to look like a sissy!" I said.
Both girls looked at each other with wide grins. "Oh, we can help you with that, little sissy!" Kaitlin said. "So what brought this on?"
"I did something bad," I said. "And I want you to punish me for it."
"So we can do whatever we want?" Summer asked.
"Well, within reason," I said. "I don't want you to put any marks on me."
"All right, sissy boy, let's tie you up then!" Kaitlin said.
The two girls quickly bound my wrists behind me, and then tied my ankles. Then they got me down on the carpet at my feet, and sat next to me. "So what did you do?" Summer asked.
"I can't tell you that," I said. "But I deserve to be punished."
"Are you in some kind of trouble?" Kaitlin asked.
"No, I just kinda hate myself right now," I said.
"All right then, I can think of some ways to punish our little sissy!" Summer said.
Then she pulled up my dress, pulled down my panties, and slapped my naked butt. I barely felt it.
"How did you like, sissy boy?" she asked.
"Is that the best you can do?" I asked.
"No," she said. Then she hit me a half dozen times with a hairbrush, and those started to sting.
"Better," I said.
"Be quiet!" Kaitlin said, and held a penis gag up to my mouth. "You like sucking cocks, don't you?"
I opened my mouth and she shoved it in,and then tied it in place. While I was working it around in my mouth, I felt something press against my butt. I tried to look up at them, and then I squealed as something forced its way into my butt.
"Does that feel good, Andrea? You've been bad," Summer said. " and bad little sissies deserve to be fucked, don't they?"
I groaned as it went inside me. It wasn't really that big, but I wasn't expecting it from them. Then my butt cheeks closed around it, and the girls tied my ankles up to my wrists in a hogtie, forcing the thing further into me, making me groan again.
The girls pulled me up on my knees, and Kaitlin said, "Andrea, from the size of your butt hole, I'm sure that isn't your first butt plug. Fags like you must use butt plugs all the time, right?"
I tried to shake my head, but that just made my curls fly across my forehead.
"What, did you think we didn't know you're really a fag?" Summer asked. "Look at you with your pretty hairdo, all dolled up in your dress and jewelry. Even fags don't dress like you! You're just a total sissy, aren't you? A sweet little sissy who likes having cocks in both his mouth and his ass!"
"Let's invite some guys over to play with sissy boy! Just wait till they see our school's star swimmer on his knees, sucking on a fake cock!" Kaitlin said. "What do you think the guys will do then?"
I shook my head again, and squealed into the gag.
"Look, he's getting all excited!" Summer said. "I'll bet he can't wait to suck on a real cock!"
I just whimpered into the gag.
"Now look, Andrea!" Kaitlin said. "You told us you were bad, and we could do whatever you wanted, didn't you?"
I just looked up at her, pleading with my eyes.
"Answer me, you little faggot!" she snarled at me. "Didn't you tell us that?"
I reluctantly nodded my head, my eyes downcast. I didn't think they would do this to me, not right here at the school.
"Who do you think the lucky guy should be?" Summer asked.
"I think the guy with the biggest cock, don't you?" Kaitlin said.
"I'm sure Andrea would appreciate that," she said. "But I'm wondering, maybe this little fag would like it better if we had another fag come over to keep him company!"
"Good idea!" Kaitlin said. "That way Andrea can get a cock shoved up his ass, instead of down his throat!"
I just groaned and bowed my head. I had invited them to do whatever they wanted, and they were going to take me up on it.
"But you know, I have another idea," Summer said. "Maybe this little fag would like to try a taste of something different!"
"What did you have in mind?" Kaitlin asked.
The next thing I knew, Summer's panties were around her ankles, and her naked groin was in my face. "Do fags like you eat pussy?" she asked.
I instinctively recoiled, my eyes wide. I couldn't believe this was happening.
"I think sissy boy needs some encouragement," Summer said.
"Good idea," Kaitlin said.
As I dreaded what that might mean, the plug inside me started vibrating! I let out a startled scream.
"What's the matter, faggot?" Summer asked. "Doesn't that remind you of one of your boyfriends banging you?"
I shook my head, and squirmed against the ropes.
"Turn it up," Summer said. "He needs more convincing!"
The evil thing inside me started buzzing and vibrating even louder as I shook back and forth on the floor.
"Change your mind, sweetie?" Summer asked. "Ready to eat me now?"
I nodded my head as hard as I could.
Mercifully, the plug stopped vibrating. Summer stood over me, and as Kaitlin got the penis gag out of my mouth, I was staring at her pubic hair.
"Uh
what
uh-" I started.
"Andrea, what are you waiting for?" she asked.
As I just stared at her open-mouthed, Kaitlin said, "I think the little sissy is used to sucking cocks, and he doesn't even know how to eat a pussy!"
Summer just scoffed, and then grabbed my hair, and shoved my face into her. "Just lick me up and down, you'll figure it out!"
I did as I was told, and she started breathing harder. This was all new for me. As I licked her, I thought she tasted tangy, almost sweet. Then she let out a moan, and I pulled away, and looked up at her. "Did I do something wrong?" I asked.
"Don't stop, you idiot!" Kaitlin said, and helpfully shoved me forward again.
Once again, I went tongue-first into her. Her moans got louder, and I didn't know how long this would go on. Then she shoved me away, and pulled up her panties. I had expected a Niagara Falls of fluid to spill all over my face when we were done. But before I could even say anything, Kaitlin stood over me, and pulled my face into her. She was already wet, and I just started licking, and she started moaning louder and louder. I thought she tasted more salty or even bitter, but then she was also done with me.
As I watched her pull up her panties, Summer pressed the penis gag back into my mouth, tied it off, and shoved me face down on the carpet. "It looks like the little sissy may be useful after all," she said. "That little thing between his legs isn't good for anything, but at least his tongue works!"
Then the two girls stood over me. Kaitlin stuck her foot under my ribs, and flipped me over on my back. As I lay there looking up at them, she asked me, "So what do you think, sissy boy? Was that more fun than sucking cocks?"
I didn't have to think about it. Being bullied by girls, and made to service them was humiliating, but it wasn't as bad as having to get down on my knees so another guy could shove his cock in my mouth. Besides, dicks are nasty. I thought maybe I could get used to eating girls, so I nodded my head.
"So then you aren't really a faggot? You'd rather eat pussy than suck cocks?"
Again I nodded my head.
"It figures because he really is a pussy," Summer said. "Tell you what, pussy boy. We'll let you go now, if you promise us you'll come back here and do this again."
I looked up again and nodded, maybe a little too enthusiastically.
Kaitlin pulled me up on my knees. "I think the little cutie loved every minute of this, and can't wait to do this again," she said. "Isn't that right, sissy boy?"
I had had enough fun for one evening, and I wasn't going to disagree with her, so I nodded again.
They undid the hogtie, stood me up, and then worked the penis gag out of my mouth. "Just so there's no misunderstanding, Andrea," Summer said, lifting my chin to make me look up at her, "you really do want to come back here and be our little plaything again, now don't you?"
"Yes," I said, nodding my head. "I really do."
"Good," she said, as they finished untying me. Then they bent me over again, and I groaned and then gasped as they worked the butt plug out of me. "Now run along home, and we'll think up more fun things to do with you!"
I dragged myself up to my feet, relieved that nothing was broken, and I wasn't seriously injured. "OK girls, bye," I said.
Chapter 5 Mistress Caroline
As I shuffled back to my dorm room, I thought over and over about what the girls had done to me. I had played so many bondage games with Caroline, but her body was off limits to me. These girls would do things that Caroline wouldn't. When I got back to my room, Caroline was waiting for me.
"Andrea, what's going on?" she asked.
Caroline wasn't just my girlfriend, she was also my best friend, and what I had done tonight had to be considered cheating on her. For all I knew, she had some kind of female sixth sense, and could smell those girls on me. I couldn't tell her all of the truth, but I didn't want to lie to her, either.
"I did something bad last weekend, but I can't tell you about it, because then that would involve you," I said.
"How bad is it?" she asked.
"As long as I don't say anything, I'll be OK. I did something at the party on the yacht last weekend that I don't want the police to know about."
"The police? Just how much trouble are you in?"
"I won't really be in any trouble as long as I don't say anything, and I keep showing up at those parties on the yacht."
"That must have been some wild party," she said.
"Yeah, you really wouldn't want to go to one of their parties," I said.
"So where were you tonight?"
I had to be honest with her. I took a deep breath, and said, "There are these two older girls, Summer and Kaitlin. They're seniors. One of them somehow took pictures of me at the salon when I was tied up. They have pictures of me bound and gagged, having my hair done."
She just stared at me, and finally said, "What do they want from you?"
"Well, they're into bondage, too. And I think they want to play with me. They said if I didn't do what they wanted, they would show the pictures to their friends, and then a whole lot of people would want to play with me!"
"So now it's just two girls playing with you?"
"I didn't have a choice!"
She frowned, and asked, "What did they do?"
"I told them they can't do anything that would leave any marks on me that would show at the pool. So they tied me up and gagged me. They spanked me a little, and mostly just taunted and humiliated me."
"Then it's basically the stuff I do with you," she said. "Maybe the four of us could get together some night."
"No!" I said. I really didn't want that. The last thing I needed was for these girls to get together and start comparing notes on bondage. "They're a lot meaner than you!"
"Oh, I can be meaner if you want!" she said.
"I really don't think I want that, either!" I said.
"So are you going to see them again?" she asked.
"Uh, they said they would let me go if I promised to come back some other time, but we didn't set a date or anything."
She scowled and said, "I hope you aren't getting yourself into more trouble with them!"
I sighed. "I'm always in trouble. But those two girls are the least of my problems right now."
The following afternoon, I went back to my room and found Caroline waiting for me with a handful of rope.
"Caroline, what did you have in mind?" I asked.
She made a twirling motion with her hand, and said, "We haven't done this in a while, so turn around and put your hands behind your back."
I did so, and she bound my wrists behind me. Then she helped me get down on the floor, and quickly bound my ankles, and pulled them up into a hogtie.
"Now for the gag," she said, and held a metal ring up to my mouth.
"A ring gag?" I asked. "Why do I need a-"
She shoved it in my mouth, forcing it open, and buckled it behind my neck.
"I have to go out to the library, but I'll be back in a little while," she said. "Try not to drool on yourself too much!"
And then she left me there, slamming the door shut behind her. So there I was. Being tied up can be a turn on for me, but I thought she would be here to have fun with me. So all I could do was lie here on the floor in my pretty white dress until she returned.
But it wasn't long before I heard the door being unlocked. The thing is
it wasn't Caroline. Her brother Nigel walked in.
He shut the door behind him, and called out, "How are you doing, mate? It's been a long time!"
"Nigel??" I tried to say through the gag as I strained to look up at him.
He pulled me up on my knees, and said, "Caroline told me you were out of sorts. That you needed some cheering up!"
As he stood over me, he pulled his shorts and underwear down to his ankles, and his penis sprang out!
I tried to shake my head, but he had already grabbed me with both hands to put his dick up against my mouth. Now I realized why Caroline used this gag on me!
"She said you had this coming, and I'm only too happy to help out a friend!"
Then he was in my mouth, and there was nothing I could do as he rocked me back and forth, his penis growing inside me. When he started spurting I just swallowed over and over until he was done.
He put his pants back on, sat next to me, and worked the gag out of my mouth. "Feel better now, mate?" he asked. "Was that what you deserved?"
I worked the stiffness out of my mouth and said, "Nigel, I thought we were already even!"
"Yeah well, we are, more or less. But Caroline told me you did something bad, and you thought you needed to be punished, so she asked me if I could come over and take care of it for you."
"How nice of you," I said. "And her."
"Come on, mate, I missed you!" he said, and then wrapped an arm around me, and drew me in and planted one on me, a full, open-mouthed kiss with plenty of tongue.
I'm still not used to being kissed by him, but I finally recovered and said, "You know I'm with your sister now, right?"
"Yeah, I know," he said, and started untying me. "It's just that you're really cute all dressed up like this, and like I said, I missed you!"
After he untied me, he brought me up to date on his swimming at the university, and I told him about our swim team. Before long, Caroline returned.
"Oh, you untied her?" she asked. "Did you have your fun first?"
He didn't say anything, but just looked at me. "Yes, he did," I said, scowling at her.
"And sissy didn't like it?" she asked. "I thought you needed to be punished!"
"Well, that wasn't exactly what I had in mind!" I said.
"OK, then we'll need to work that out later," she said.
After a while, Nigel said he had to go, something about having dinner with his friends at the university. After he left, Caroline picked up some rope, and turned to me.
"Since that must not have been the punishment you wanted, turn around so I can tie you up."
"Um, OK, does this have something to do with-"
She slapped me across the face hard! "Oooh!" I gasped, and held my hand up to my burning cheek.
"Don't make me repeat myself, sissy boy!" she said, glaring at me. "Do it NOW!"
I turned around and felt my wrists being drawn together and bound with rope. Then she spun me around and held a ball gag up to my mouth. I opened my mouth, she shoved the gag in, buckled it tight, and then turned me back to face her.
"Maybe you don't understand our relationship, sissy!" she said, cupping her hand under my chin, and tilting my head back to make me look up at her. "You are just a slave. I am your mistress, and you will do whatever I tell you!"
I tried to nod my head, despite her grip on me.
She stood nose to nose with me, and said, "If you understand me, you little faggot, say 'yes, mistress.'"
"Yes, Mistress," I tried to say through the gag.
"I see now I was wrong to think sucking a cock would be the right punishment for you," she said. "Of course. You fags love sucking cock, so it's no punishment at all for you, is it?"
"No, Mistress," I tried to say.
"But I think I know what a better punishment would be," she said. She had one hand on my chin, and now the other one slid down over my breasts. "Since you want to dress up and look pretty at school, we need to take you shopping for some more outfits."
I just looked up at her, afraid to speak.
"You need some slutwear!" she explained. "Low-cut dresses with those big boobs of yours practically falling out of them! That will get the attention of the boys at school, don't you think? That'll be perfect for a fag like you, then you can give all the blow jobs you want!"
I tried to protest but only little sounds came out.
"And while we're at it, let's pick up some new swimsuits for you, too. Instead of those one-piece racing suits, we can get you some string bikinis, the kind that barely cover your nipples. You'll love swimming laps in those every morning! I can't wait until the guys on the swim team see you! Oh wait, never mind the swim team, every boy in the school will be getting up at six o'clock in the morning just to watch you at swimming practice!"
"Caroline!" I tried to say.
"Every morning after swimming practice you can give all our teammates blow jobs, too! Just think of what that will do to help recruitment for the swim team. Once the other kids find out little sissy Andrea gives blow jobs to the rest of the team, every boy in the school will be competing to join the swim team!"
Then she backed me over to my bed, threw me onto it, and started binding my ankles.
"I'm sure you'll do that for us," she said, throwing herself on top of me. "Once the whole school finds out how good the little faggot Andrea is at giving blow jobs, don't you think all of the boys will be after you? You're willing to take one for the team, aren't you?"
Oh, my God. I was pinned underneath her, and her breasts were pressed against mine, and now my dick was stirring. The thought of being made to dress up like a slut at school, being forced to swim my laps in a string bikini while the other kids watched
it was overwhelming!
She started working the gag out of my mouth, and said, "Do you have anything you'd like to say?"
I just gasped and tried to catch my breath.
"What's this?" she asked, reaching a hand down to my groin, which made my penis spring erect. "Is little Andrea getting all excited now?"
My dick was rock hard, the rest of me was tied up and couldn't move, and I didn't know what to say. She waited maybe a couple of seconds and then kissed me hard enough to rattle my teeth.
When she finally released her lip-lock, she said, "See, I told you I could be meaner."
I just looked up at her and said, "Yeah, I see that now."
"But don't worry," she said. "As long as you do what I tell you, we'll get along fine."
"Absolutely," I said, nodding.
"Good, because Halloween is coming up, and the swim team costume party. I was thinking you'd look adorable in your maid's costume. You know, that shiny pink satin one. The one with the frilly little cap," she said.
"Good idea," I said. "I haven't worn that in a while."
"And no one's ever seen you in it except me, Bob and Jenny," she said. "I can't wait for the rest of the swim team to see how cute you look in that outfit!"
"What are you going to wear?"
"You're going to buy me a Supergirl costume!" she said.
"Actually, that's very appropriate," I said.
"Yes, and it's just as appropriate that you're going to be my maid, isn't it?" she said, stroking my hair.
"Yes, Mistress," I said. "Whatever you want."
After an extended session of making out, she finally decided to untie me. I understood why she had punished me. I really hadn't treated her very well lately, between feeling sorry for myself and going to see Summer and Kaitlin. But I decided that since Caroline had forgiven me, I must not be that bad. So I put my dresses and penis chastity away, and went back to wearing blouses and skirts, although I kept wearing jewelry. The first chance I got, I made an appointment to have Karen trim my bangs, and go back to my old look. Of course I had to put up with being tied up and gagged with a scarf again, while Karen complimented me on my hair. She questioned me about going back to my old look, but she accepted that a girl could change her mind, even a fake girl like me.
I was a little nervous about going to the Halloween party in a maid's uniform, but it went very well, aside from some of my teammates and their friends ogling me in this outfit. Lots of people took pictures of us together, with Caroline in red and blue tights, and me in pink satin with puffy sleeves, a big white apron tied with a bow, and lace everywhere, including my frilly cap.
When John complimented me on my costume, Caroline said, "Oh, that's not a costume! That's her uniform, I make her wear it every night to clean our room!"
I just rolled my eyes and said, "Yes, that's one of her super powers, she can make me do whatever she wants!"
Everyone had a good laugh, but it all turned out well because I wasn't one of the new kids on the team any more. Now I was star of the swim team, and no one harassed me because they didn't want to lose their meal ticket. One of the guys asked me when I was going to learn how to surf, and I had to make some lame excuse that I had been too busy. Of course the real problem was that every time I had gone somewhere to find out about surfing lessons, I had been kidnapped, or worse. But tonight I was actually more worried about Caroline doing something that might put me in some kind of compromising situation, but even she behaved herself (most of the time, anyway) and another disaster was averted.
Speaking of disasters, I had sent Mr. Silvers a text explaining that I had a swim meet coming up in mid-November, and then Thanksgiving late in the month. So if he wanted to use me for a weekend of abuse and debauchery, it would have to be early in the month. Of course I didn't put it in those terms. I humbly asked if I could be invited to his yacht on a weekend earlier in the month. Apparently being the boss means his schedule is flexible, that is, he can do whatever he wants, and he agreed to the first weekend in November. So that was settled. I had a vague idea that I was going to be an Australian porn star again, but I had no choice but to go through with the arrangement.
Chapter 6 Blonde Beauty
Friday night, I wore my jewelry, a white blouse, blue skirt, and white boots. I told Caroline I was going away for another weekend on the yacht, and she gave me one of those looks. "It's an obligation and I have to go, but ll be back Sunday night," I said.
My car parked itself at the marina, and there was the huge yacht in front of me. The security guard let me through, and I went up the gangplank and aboard the yacht. I looked around and saw various people working in the dining room, and wondered how many people lived and worked on this yacht. I figured they had to know what went on here. Who knows how many others like me, had been abused below decks. Those two boys being thrown overboard into the ocean. For a yacht of this size, there must be dozens of crew members. Maybe they ignored whatever happened here because they were all in the pay of the tech billionaire. After all, anyone who spoke up might get thrown overboard too.
Then the editor Watkins saw me. "Andrea, I'd like to show you to the guest bedroom."
I followed her downstairs to the now familiar room with the large canopy bed.
"Now take off all of your clothes and jewelry. Everything but your high heels, I understand you need to stand on those."
"Um, OK. I just got here, but I have to get naked now?" I asked.
"That is what I said, isn't it?" she snapped at me.
"Yes, Ma'am," I said, and started taking off my jewelry, and then peeling off one item of clothing after another until they covered the bed, and I was standing there in my birthday suit.
"Now turn around and put your hands behind your back," she ordered me.
I did so, and felt a pair of handcuffs snap into place around my wrists. Then she used a pair of leather cuffs to chain my ankles together. "Am I going to bed already?" I asked.
"Not exactly," she said. Then she put a collar around my neck and tied it off to the top of one of the posts of the canopy bed. "Wait right here, and someone will be along to see you."
Then she left, and a feeling of dread came over me. I was tied up and naked and some guy was probably on his way here right now. Probably a big guy with an organ fit for a horse, and I was going to have to do whatever he wanted.
Then I heard footsteps. The good news was that it wasn't a big guy, it was a girl. The bad news was that it was the teenage girl they called Brittany, who wanted to throw me overboard.
"They told me the little sissy was back. I didn't think you'd come here again unless you wanted another beating!" she said. Then she held up a tiny key, and went on, "But in case you don't really want a beating, here's the key to your handcuffs, so you can escape."
Then she threw it across the room, where it landed next to the far wall. I was tied to a bedpost, and it was way over there. "But I can't reach it!" I protested.
She pressed a ball gag against my mouth, then into it, and tied it off behind my neck. "Sweetie, I know some guys are into getting beat up by pretty girls, so I'll be happy to play along with you," she said. "But if I'm wrong about you, the key is right over there."
I looked over at the key, and shook my head, but she was already gone. The rope from my collar was tied up to the top of the bedpost, and there was no way I could reach it with my hands cuffed behind me. So I hopped over to the side of the bed, and threw myself onto it, flat on my back. Then I tried to pull my legs back in the hope that I could somehow get them close to my hands. Then maybe I could pull my legs through and get my hands in front of me so I could reach up and untie my collar from the bedpost. I was squirming around on the bed, and not making much progress. That's when Brittany returned, and saw me writhing on the bed.
"Oh, aren't you having fun?" she said. "I knew you were really into this!"
I shook my head, and then was even more alarmed to see she was carrying more rope. She untied my collar from the bedpost, and then sat me on the floor. Then she threw a long rope over a bar set in the ceiling, and when the free end of it dangled next to me, she tied it to my ankle cuffs. The she pulled out the slack in the rope until my legs went straight up. I screamed into the ball gag, and she lifted me off the floor until I was suspended upside down, and then she tied the rope off somewhere.
"How are you feeling now, sissy boy? Is this everything you hoped for?" she asked. "Are you ready for your beating?"
I shook my head again, and tried to tell her to stop. Then I saw she was holding a riding crop, probably the same one she had previously used on me.
She used it to poke one of my breasts, and the pain made me squeal. "What's the matter, sweetie? Are you sensitive there?"
I nodded my head, and she pressed the crop against my dick, which made my entire body shudder.
"You're sensitive there too?" she asked. "You're just a big baby, aren't you?"
I just groaned into the gag, and she spun me around, and I felt a sharp pain in my butt as she smacked me. Then another loud crack as she hit my other butt cheek. I tried to scream into the gag as she spun me around, and then the crop landed on my breast. I strained against my bonds, but then she hit my other breast, and my eyes filled with tears.
"What's the matter, faggot, are you crying?" she asked. "Then I'll give you something to cry about! You wanted a beating, didn't you?"
Then she hit my butt another half-dozen times, until I was sobbing and squirming, and my hair went flying every time she hit me.
She grabbed a handful of my hair, and pulled my head up to make me look at her. "Is that all you can take?" she asked me. "Have you had enough, sissy boy?"
I tried to nod my head and say yes, and she let go of me and left me to dangle upside down.
Then she walked out and left me hanging there. But it wasn't long before she returned with Watkins. "The little faggot was crying like a baby, and I didn't even hurt him enough for a Band-Aid!" she said.
Watkins took me in her arms, untied the rope from my ankles, and carried me over to the bed. But when she laid me down, my butt felt like it was still on fire, and I rolled over onto my side.
Then Brittany climbed onto the bed next to me, turned my face to make me look at her, and squeezed my cheeks. "You aren't going to tell anyone anything about what happens on this yacht, are you?" she asked.
"NO!" I tried to shout into the gag.
"You sure about that, faggot?" she asked. "Because if you do, I'll be the one that gets to throw you in the ocean!"
I tried as hard as I could to shake my head.
Finally she let go of me, got up and told Watkins, "He's your problem now."
After Brittany left, Watkins got the gag out of my mouth, uncuffed me and gave me some time to get cleaned up. Then she put me to bed in a white nightgown and leather cuffs for my wrists and ankles. "Tomorrow is going to be a much more interesting day for you," she said.
I didn't even want to think about what that might mean, because these people had a lot of imagination when thinking up ways to abuse me. Besides, I was so exhausted from the beating that even with my sore butt, and my wrists bound behind me, I fell asleep right away.
They let me sleep in the next morning before Watkins got me out of bed. I had a few minutes to shower and throw on a white dress before she hustled me over to what looked like a small beauty salon, only without any mirrors. They had told me there was a salon on the yacht, but I hadn't really believed it until now. She tied my hands behind my back, backed me into a chair, and told me to stay there. I squirmed a little because my butt still hurt, but most of the weight was on my upper thighs, so it wasn't too bad.
Soon a young blonde woman walked in, smiled at me, and said, "Andrea, I'm Mary, and I'm going to do your hair. You don't mind being tied up while I do your hair, do you?"
"No, Ma'am, I'm used to it," I said.
"Yes, I know," she said.
"You know that I'm used to being tied up in a salon?" I asked.
"Of course!" she said. "They're watching you all the time, including when you have your hair done! So now I'm going to give you a new look!"
I wasn't sure which of that was more upsetting. They're always watching me, or I was getting some new look. It seems that every single person on this yacht knows about the awful and illegal things that go on here, and they either enjoy it, or just don't care.
Meanwhile she was using a brush to smear stuff all over my hair. and this seemed like a much more involved process than anything Karen ever did in her shop. Then I had to get my hair washed and shampooed over and over again. It seemed like this was taking forever, and then she and another young woman descended on me, and started brushing my hair, and waving portable hair dryers and curling irons around.
Most of my hair had been pulled back behind my back, but occasionally I saw a flash of something much lighter. "Is it the lighting in here, or did you change the color of my hair?" I asked.
"You'll see. We're almost done," Mary said. "I think your bangs are very pretty, so we aren't changing the style, but the dye job turned out very well."
"Dye job??" I asked, my panic rising. "What
what did you do?"
Then she brushed out my hair, and let it fall over my shoulders and down to my breasts. I saw a bright, shiny cascade of yellow. "Andrea, you look lovely as a blonde!"
She held a small mirror in front of me, and I saw the reflection of my face framed in pretty yellow hair. "Oh my God!" I said.
"Yes, it looks wonderful, doesn't it?" the other woman asked.
"I
I'm just wondering what the boys on the swim team are going to think when they see me."
"Andrea, you were pretty to begin with," Mary said. "But now I think you'll get even more attention from the boys!"
I was going to tell her that wasn't really a good thing when Watkins showed up to collect me. She got me up and turned me around and around. "Andrea, you should have gone blonde a long time ago," she said. "I think my magazine might do another feature on you. Think of the before and after pictures of a cute little boy who becomes a beautiful young lady!"
"I can hardly wait," I said. The last time they did a story on me, I started out by getting stuffed in a suitcase, and then it went downhill from there.
She marched me out of the salon and into another room I had never seen before. The room was long and narrow with a dark blue carpet, and it was empty except for a chair with a pink dress draped over it. She untied me, and I got a good look at the dress. It was a flimsy pink outfit with a pair of tights, and a large pair of pink wings on its back.
"You're going to be a fairy princess!" she said. "Isn't it pretty?"
By now I knew better than to complain, and I was resigned to my fate, so I just said, "Yes, Ma'am."
Oh, but then it got even better. She held up a wand, with a pink star on its end. "And this is your magic wand!"
It's not the star that worried me. It was the handle that caught my attention.
She noticed that, and gave me a wolfish smile. "Sweetie, do I have to tell you where the wand goes?"
I had already guessed. The end of my magic wand was a butt plug, already glistening with lube. "I think I can guess," I muttered.
"Then bend over the chair," she said. "The guests will be here any minute."
So I bent over the chair, and wondered what guests were coming here, when the butt plug started pressing into me. I tried to relax, but I squeezed my eyes shut, and groaned just the same.
"Andrea, stop being a baby!" she snapped at me. "This is a small plug, and your butt hole is big enough now to take it!"
"If you say so, Ma'am," I said, groaning again as my butt closed around it. Now I was dressed as a fairy princess with my magic wand sticking out of my ass. I wondered what else could go wrong today.
Then two photographers showed up, and started taking pictures of me, telling me where to stand, turning me around, and making comments about how pretty my hair was.
"Of course we can't use these pictures in my magazine, but they will go in a very special gallery," she said. "Now I need to put some cuffs on you."
I wondered where this special gallery was. Most likely somewhere in Australia where I was an underground porn star. Meanwhile, she applied leather cuffs to my wrists and ankles, both of which were connected by a foot of chain, which gave me plenty of freedom of movement. Then a pink collar with the word "SISSY" written on it went around my neck, and she hooked a leash onto it.
"The guests are here," one of the photographers said, and I watched them take up their positions on either side of the room.
"Andrea, get down on your hands and knees," Watkins said. "When I tell you to start, you will begin to crawl across the room."
"Yes, Ma'am," I said, and the plug shifted as I got down on all fours.
"And when I tug on the leash, you will stop," she said.
"Yes, Ma'am," I said.
"Then you will turn to the left, blow kisses to those guests, and then turn to the right and blow kisses to those guests," she said.
I looked up at her. "Ma'am, you want me to blow kisses?"
"You know how to do that, don't you?" she asked, and then put her hands up to her mouth to demonstrate by blowing a kiss.
"Yes, Ma'am" I said, and watched as men filed into the room, and lined up along both long sides of the narrow room.
Then Watkins said, "Sissy Andrea would like to welcome you to the yacht!"
I heard some laughter from around the room, and Watkins told me to start.
I was chained up on my hands and knees, wearing a collar that said, "SISSY" dressed up like a fairy princess with a magic wand sticking out of my ass, and now I had to blow kisses to these men. I looked up and stared at a sea of smiling and laughing faces.
"We seem to have stalled," Watkins said. Then she gave that magic wand a twist.
As the plug shifted inside me, I let out a scream and then a whimper. That made even more men start laughing, and I felt my face turning red with embarrassment. I crawled forward a couple of steps before I felt a tug on my collar.
I did as I had been told. I stopped, turned to the left, and blew kisses to those men. Then I turned to the right, and blew kisses to them.
Then the whole room exploded into laughter, and I turned bright red with humiliation. I put my head down, and curtains of yellow hair draped around me.
"Get moving, Andrea," Watkins said.
So I started to crawl again, but after two more steps, she tugged on the leash again. I duly stopped, and blew more kisses to the men on both sides of the room.
"Hey fairy princess," a man called out to me. "Do fairies like to suck cock?"
"Yeah, fairy!" another man yelled out. "Or do you just like having stuff shoved up your ass?"
"Move it, Andrea," Watkins said.
But I only got two more steps before another tug on the leash stopped me, and I had to blow more kisses.
"Hey faggot, why don't you come over here and kiss my dick right now?" a man yelled at me.
"Yeah, faggot, are you going to suck all our cocks?"
"Don't worry, guys. Sissy Andrea will do his best to take care of all of you!" Watkins said, and then she looked down at me and added. "Won't you, Andrea?"
I looked wildly around the room, and there had to be at least thirty guys here. But I just said, "Yes, Ma'am," and I started to crawl again.
"Look on the bright side, Andrea," she said. "As long as you've got that wand inside you, nothing else will get shoved up your ass!"
That wasn't a very comforting thought as my ordeal went on.
"Andrea, that's a pretty name for a fag!" a man called out.
"Sissy Andrea, you must be the sweetest little sissy ever in that outfit!" another man yelled at me.
Then I had to stop and blow kisses again. It went on and on, and I wondered how so many people on this yacht could let things like this happen. Finally I made it to the end of the room.
"How many of you want blow jobs?" Watkins announced to the room.
A roar went up.
"That sounds like everyone, but don't worry because Andrea has never met a cock he didn't want to suck," she said, and then turned to me. "Isn't that right, Andrea?"
"Yes, Ma'am," I mumbled.
"What he means is that a sissy never says 'no' to sucking cock," she said. "Right, Andrea?"
"Yes, Ma'am," I mumbled.
She gave a sharp tug on the leash, and snarled, "Because you fags give the best blow jobs, don't you?"
That jolted me, and I looked up at her angry face and said, "Yes, Ma'am, we fags give the best blow jobs."
Then the room burst into laughter, and I blushed bright red again, and wanted to start crying right then and there.
"All right, guys!" she said. "Make a single line in front of the little fairy, and lets see how much cum he can swallow!"
As the men hurried to line up, she untied my wrist cuffs, and then I winced as she bound my wrists tightly behind me with rope.
"That rope stays on until you take care of all of our guests," she said. "So if hurts, then get to it!"
In front of me was a line of men that stretched the length of room, and I was on my knees dressed up as a fairy princess. Just about every guy was hard before he even got his thing out of his pants, and just about every one of them grabbed me by my pretty hairdo, and slammed his dick into my face over and over. My mouth was always full of that salty taste, as they made me swallow most of the cum, but some of them sprayed it on my face and into my hair. In a few rare moments between men, I noticed the photographers were at work through all of it.
I was exhausted and my jaw ached when the last guy was done with me. Then Watkins untied me, and my wrists ached as the blood flow returned, and as I tried rubbing and shaking them, Watkins said, "Very good, Andrea. I'm impressed with your stamina."
"I'm an athlete. I work out to build endurance," I said. "But this isn't what I normally train for."
"Well then, lucky you," she said. "Now that we know what you're capable of, we can have even more fun with you!"
That didn't sound good at all. I just looked up at her, but I didn't say anything. It turned out my day was over, although getting that wand out of my ass made me groan again. But then they let me have dinner, and go to bed. But as Watkins tied me to the bed, she mentioned that there would be a reception tomorrow afternoon, and I was invited. "Invited" meant that I was going to be there whether I wanted to or not.
Sunday morning they let me relax up on the deck, sipping from a glass of iced tea as the yacht cruised along on the open ocean. So this is how the super-rich live. But I wasn't one of them; I was the plaything of the super-rich. And we were headed back to the marina, where I knew that Silvers' friends would be waiting to come aboard.
That afternoon, Watkins took me down below to the pool. That's right, there is 25-yard pool inside the yacht. Of course it didn't look like the pools I swim in. The bottom was covered by a mosaic of tiles in a rainbow of colors. There were marble statues all along the walls. A bartender was on duty to provide anyone's beverage of choice. Even the ceiling was lit up with a projection of puffy white clouds floating by. I didn't think they brought me down here to swim laps.
She told me to get undressed, and soon I had stripped down to my high heels. Then she had me hold out my hands, chained them together with leather cuffs, and tied them over my head to the wall next to the last statue. Now I felt completely exposed and vulnerable, tied up and naked, just like another statue, but she wasn't done with me yet. She wrapped the pink SISSY collar around my neck, and then held a red scarf up to my mouth, and said, "What do you think of this color?"
As if I cared what color scarf would be shoved in my mouth. "It's lovely, Ma'am," I said.
"I think so, too. You're fair skinned, and it really goes with your new hair!" she said. "Open your mouth!"
I did so, and she tied it through my lips, and under my hair around the back of my neck. Then she straightened out my hair, and let it cascade across my shoulders and down to my breasts.
"Andrea, as pretty as you are as a blonde, you look even sexier when you're chewing on a cleave gag!" she said. "I'm sure you'll get plenty of attention from the guests!"
The only nice thing about cleave gags is that they are only for show. I could still speak reasonably well, and asked, "What are the guests going to do to me?"
"How does this feel?" she asked, and then picked up what looked like a flyswatter, and smacked my breast with it.
It barely stung, but the shock of it still made me squeal.
"Would you like me to replace it with a wooden cane?" she asked.
"No, Ma'am," I said.
"I thought so," she said, and then rested it against the statue. But then she slipped a blindfold over my eyes, and I was startled as everything went dark.
I started to speak, but she said, "Be quiet now, Andrea. The guests will be arriving soon. Speak only when spoken to, and you'll be fine."
"Yes, Ma'am," I mumbled through the gag.
"Oh, don't worry, sweetie," she said. "I'm sure a little cutie like you will be very popular with them!"
That didn't make me feel any better at all.
Then I heard more talking behind me, and then the sounds of people milling around. Then another smack on my breast made me yelp. But no one spoke to me. I relaxed, or at tried to relax, which isn't easy when you're tied up, naked, blindfolded and gagged in front of a room full of strangers. I only heard bits and pieces of conversations when another smack on my breasts would get my attention. But no one talked to me; I was here just to provide the guests with the entertainment of swatting my breasts.
Then after another whack on my breasts, a woman spoke to me. "You're a pretty little thing, aren't you?"
"Thank you, Ma'am," was my automatic reply.
"What's your name?"
"Andrea," I said.
"That's a pretty name. They told me you were half boy and half girl," she said. "But look at you with your big breasts and your tiny little penis. You're much more of a girl, aren't you?"
"Yes, Ma'am," I said. "I'm living as a girl now."
"I can see that, with your bright red nails, and all this lovely blonde hair," she said, stroking my hair.
"Thank you, Ma'am," I said, but being blindfolded was scary, and I tried not to shiver at her touch.
"With that figure of yours, someone must have gone to a lot of trouble to sissify you," she said. "Or did you do it yourself?"
"I, uh, I'm just trying to live as a girl, Ma'am," I said.
"And why is that?" she asked, taking my chin, and turning it from side to side. "Were you too girly to live as a boy?"
"No, Ma'am, I, uh, I was just, uh-"
"Oh, it sounds to me like you're a sissy. Your collar says so. You're small and cute, and you must have been growing your hair for years to get it this long," she said. "Now here you are on display for us. How did that happen?"
"I, uh, I just come here for a weekend sometimes," I said.
"So you're a little sissy boy, and you like to spend your weekend getting naked, and being all tied up and helpless here?"
"Well, Mr. Silvers invited me-" I started.
"Oh, he invited you, so then you couldn't pass up the chance to suck his cock, right?" she said. "You have sucked his cock, haven't you?"
I nodded my head.
"You know what?" she whispered, very close to me now. "I heard a rumor you sucked a whole room full of guys yesterday. Is that right?"
I just nodded again.
Then a man said, "How are things going here?"
I recognized the voice, it was Mr. Silvers. "Ah, Mr. Silvers, I was having a lovely chat with this little sissy. Is he for sale?"
I gasped. For sale??
"Everything is for sale. Everything has its price," he said. "Business is business."
"Then how attached are you to this child?" she asked. "I think I could have a lot of fun with this one!"
"You'd have to outbid the Australians," he said. "Andrea here would be very expensive."
"If I can't do an acquisition, maybe we could work something else out."
"Are you thinking of a short term rental?" he asked. "Try before you buy? I'll give you some videos so you can watch Andrea perform."
I couldn't believe what I was hearing. They were discussing whether or not they would sell me or just rent me??
"That sounds wonderful," she said. Then I felt another whack on my breast, and she added, "See you later, Andrea!"
Then both of them walked away and left me alone. So I just stood there and heard the sounds of a party going on. Glasses or bottles clinking together, people splashing around in the water, and conversations going on, mostly people talking about the stock market, and how much money they were making.
After a while, things quieted down, and then my blindfold was pulled off. I blinked against the light, and looked up to see Mr. Silvers.
I looked around at the empty room, and asked him, "Everyone's gone?"
"Yeah, party's over," he said. "I hope you weren't too bored, but some of my associates were quite taken with you."
"Who was that woman that wanted to buy me? She was kinda scary."
"She's the president of a tech company. But don't worry. If you do as you're told, I won't sell you to her."
"Yes sir," I said. "Whatever you want."
"Good!" he said, pulling the gag out of my mouth. Then as he untied my wrists, added. "Now get down on your knees for me!"
"Yes sir," I said. When my hands came free, I got down on my knees, and his pants were already down.
He forced my head down, I took him in my mouth, and it didn't take him long to start spurting in my mouth. He made me swallow all of it, and then let go of me. "Andrea, I think you may have promise."
"Sir?" I asked, swallowing, and trying to get the salty taste out of my mouth.
He waved his hand. "Never mind, we'll discuss this another time," he said. "Your weekend is over. Get something to eat, and then go on back to school."
"Yes, sir," I said.
So I got dressed, and then went to the dining room to have dinner. I didn't understand this place at all. Every time I came to this yacht, they abused me like a piece of meat. But once they were done using me as a sex toy, they would treat me like an honored guest at a fancy hotel. I ate well, and I was going back to school with new hair. I wondered how I was going to explain that.
When I got back to my room, Caroline took one look at me and her mouth dropped open. "I didn't know you wanted to go blonde!" she said.
"Neither did I," I said.
"So what happened?"
I just sprawled on my bed and said, "Another one of those wild parties. The magazine editor thought I needed a new look. She said they might even do another feature story on me now."
She grinned at me. "It IS very pretty, you know!"
I knew what that grin meant. She wanted to tie me up right now. "Caroline, it's late, and we have to get up early tomorrow to swim laps," I said. "So we can play games tomorrow night, OK?"
"I can hardly wait!" she said.
I went to sleep that night wondering what the other kids would think of my new look.
Chapter 7 Slave Girl
The following morning I actually made it through our morning practice without anyone seeing my hair, thanks to my swimming cap. No one noticed until after I had showered, dressed, and dried my hair, and then walked out across the pool deck with Caroline. That's when I heard all of the gasps from our teammates, and looked over to see the guys staring at me.
"You'd think they'd never seen a girl before," Caroline said.
At least they didn't make any rude comments as we left. Actually, as the day went on, I received lots of compliments on my hair from girls, some of whom wanted to know where I had my hair done. So I made it through the day with my new hair, and that night Caroline took me up on my offer to tie me up and play with me. At least she didn't leave me with any bruises, and we got to bed early enough to get up for the morning swimming practice.
By Friday, I figured everyone was used to seeing me with blonde hair, and nothing horrible had happened to me. That night, Caroline told me we could have some real fun since we could sleep in the next day.
"Sure, whatever you want," I said.
Soon I was lying face-down on the floor in a hogtie, wearing nothing but snug white ropes. Then she shoved a ball gag into my mouth, tied it off behind my neck, and then gathered up my hair, and let it spill all around my face. "Andrea, don't you look cute?" she asked.
I just mumbled into my gag.
"I'll be right back," she said. "Now don't you go getting into any trouble on your own!"
"Huh?" I tried to speak. She was leaving me here like this? But then I heard the door slam shut, and she was gone. So I waited, and maybe ten minutes later, I heard the door open. I thought I heard more than one person come in, but thanks to this mane of golden hair all around me, I had no peripheral vision. All I could see was the carpet in front of me.
Then she spun me around and pulled me up on my knees. Summer and Kaitlin were looking down at me, and both of them were grinning from ear to ear.
"Hi, Blondie!" Summer said.
"Don't you look pretty with your new hair!" Kaitlin said.
Caroline squatted next to me and she didn't look happy. "Andrea, I understand these girls are also bondage friends of yours," she said. "And that you've been a lot more intimate with them than with me!"
I looked up at her in terror, but I was gagged and couldn't say anything.
She grabbed my chin, and turned my face up to make me look at her. "Did you think we wouldn't talk to each other?"
I tried to shake my head, and made only squeal sounds into the gag.
"Do you have something to say?" she asked me.
I nodded my head vigorously.
She pulled the gag out of my mouth and said, "Speak!"
"Caroline, they have pictures of me tied up, and they said they would show them to their friends if I didn't do what they wanted!"
"That's true," Summer said. "But then little sissy boy came back to us and asked us to do it again. That's when we let him eat us."
"Is that what happened, Andrea?" Caroline asked me.
"But that was when I told you I did something bad," I said. "Remember, I said I deserved to be punished? That's why I went to see them."
"Oh, so you went to them," she said, "so they would punish you by making you eat them?"
"Yes," I said, and quickly added, "but I didn't know they were going to make me do that!"
"Then you know what, sissy boy?" she said. "I think you need to be punished again!"
"What
what do you mean?" I asked.
"Summer, Kaitlin," she said. "How do you feel about sissy Andrea going down on you again?"
Both girls exchanged savage grins. "That sounds like fun!" Kaitlin said, and she turned to me. "Does that sound like fun to you, Andrea?"
I looked up at my roommate. "Caroline, I'll do whatever you want me to!"
She sat in a chair, and nodded to the girls and said, "I'd like to see this."
Summer started unzipping her blue jeans. Kaitlin walked around behind me, and as soon as Summer's panties dropped, she shoved my face into her. I had to do this while my girlfriend was watching. I had this strange taste in my mouth again, but all I could think about was Caroline, and what she would think of all of this. But I was tied up and had to keep licking Summer, and she kept moaning until she finally came. Then she traded places with Kaitlin and I had to do it all again. I glanced over at Caroline but she never said a word until both girls were done with me.
"See that, Caroline?" Summer said. "Even sissies are good for something!"
Caroline made a non-committal grunt that didn't tell me anything.
Soon both girls got dressed, thanked Caroline for the use of her sissy, and left. I was alone with Caroline, and she sat in the chair with me in front of her on my knees.
"I'm sorry, Caroline!" I said. "Please forgive me!"
"Andrea, I can think of a way you can make it up to me," she said.
"Anything, whatever you want!" I said.
"From now on, when we are alone here in this room, you will address me as 'Miss" and you will be my slave."
"Uh, OK," I said. "That's fine with me."
"Are you sure about that? It's for the entire school year," she said.
"Yes, Miss," I said.
"And one more thing. Your Thanksgiving holiday is coming up. Were you going to invite Nigel and me over for dinner at your house?"
"Yes, Miss," I said. "Of course!"
"Good. Then when my brother shows up at your house, I'd like you welcome him by giving him a blow job."
"But
but my parents will be there!" I said.
"It's a big house. I'm sure the two of you can sneak off somewhere, and then when you're alone, you can ask him
or beg him to let you suck his cock. I'm sure he'll take you up on it."
I looked up at her. "Miss, is that all I have to do, and you'll forgive me?"
"That's all. I mean, sucking cocks isn't really a problem for you, is it?"
"No, Miss. I'll be happy to do that for you," I said.
"Good!" she said. Then she shoved me face down in front of her, and said, "Now kiss my feet."
"Yes, Miss," I said. I kissed the foot next to me, and then when she shoved my face over to her other foot, I kissed that one too.
Then she untied me, and after I rubbed the stiffness out of my wrists, she sat in the chair, and said, "Now do it again!"
"Do what again, Miss?" I asked.
She pointed down at her feet. "Kiss my feet again!"
"Oh," I said, and got back down on my knees. "Yes, Miss." I kissed her feet again.
"I'm glad we understand each other," she said. "Now go to bed!"
"Yes, Miss," I said.
The next day we went off to another school for a swim meet. As usual, we brought along extra faculty members for security, but no one bothered me more than usual. One girl spit in my lane just before our race started, but that was about it. I beat her badly, and we won the swim meet by a wide margin. Caroline treated me like a teammate and friend throughout the swim meet, which didn't really surprise me. When we were out and about, we were a couple. I wouldn't become her slave again until we were back in our room together.
That night when we got back to our room, she said, "Andrea, you were great at the swim meet today!"
"Thank you, Miss," I said.
"Now just to make sure you remember your place, take your clothes off."
"Yes, Miss," I said.
As I stripped down to my underwear, she said, "Now put your pink maid's uniform on. And don't forget your cap!"
"Yes, Miss," I said, and hurried to get into my shiny pink maid's outfit. I looked in the mirror, and adjusted my frilly cap to get it on straight.
"Good," she said. "Now turn around so I can tie you up."
I did so, and felt the ropes wrapping around my wrists and binding them together. Then she spun me around to make me face her. She's taller than me, so as she pulled me close I had to tilt my head back to look up at her.
"Andrea you may be the star of our swim team, but in here, you're just a helpless little sissy, aren't you?"
"Yes, Miss," I said, looking up at her.
"So you're going to do whatever I tell you to, because you're my slave, isn't that right?"
"Yes, Miss, of course!" I said.
"You're never going to see those girls Summer and Kaitlin again, are you?"
"But they have those pictures of me!" I protested.
"I talked to them, and we all agreed that they've had enough fun with you, so that should put an end to it," she said. "Unless you liked using your tongue on them? Is that a turn on for sissies like you?"
"No, Miss! I didn't want to do that. They made me do it! I didn't enjoy that at all!"
"I know. Because while you were licking them, I was watching that tiny little penis of yours," she said. "I was waiting to see if it got hard, and lucky for you, it didn't! Do you have any idea what I would have done to you?"
"No, Miss," I said. "And I don't think I want to know!"
"Yeah, you probably don't!" she said. "But I would have started by giving you a new hairdo. Maybe some big bimbo style from the '1980's. Or maybe I would have given you a perm. Then you'd be walking around with a big yellow afro for the next month! With all of your hair, you'd have to turn sideways to walk through a door."
"I
I kinda like my hair the way it is," I said.
"I'm sure you do. It's very pretty, and it suits you, what with you being a cute little sissy," she said. "But otherwise I would have to come up with some other kind of punishment, like making you wear a butt plug to class all day."
"All day long??" I gasped.
"Wouldn't that be fun? By the afternoon, you would be squirming pretty good!
"I
I can't-"
"Oh, don't worry, I wouldn't make you wear it to swimming practice. That would be cruel, expecting you to swim laps with a butt plug inside you, now wouldn't it?"
"Very, very cruel," I agreed.
She patted my cheek, and said, "And that is why you're going to be a good little sissy, and do whatever I tell you."
"Yes, Miss," I said. "Whatever you want!"
So that was what my life was like. I was student-athlete by day, and Caroline's slave at night. Except for one weekend a month, when I really was a sex slave, which helped me keep things in perspective. Whatever Caroline might do to humiliate me in our room was nothing compared to those weekends on that yacht.
A few days before Thanksgiving, my dark roots were starting to show, so I made an appointment with Karen at the salon, but I neglected to tell her about my dye job.
So when I showed up at the salon, she said, "Miss, can I help you?"
That's when it dawned on me that she didn't even recognize me with blonde hair. I said, "Karen, it's me. I have an appointment."
Then her eyebrows went up and she just stared at me. "Oh, Andrea! You look amazing! If you wanted to be blonde, why didn't you tell me? Oh, never mind, let me get the ropes to tie you up!"
So as she tied me up, I explained about the magazine editor who thought I should have a new look. Karen then assured me that she could take care of my new hair. Dyeing my roots meant a longer stay in the salon, which meant more time being tied to a chair with a scarf gag in my mouth, but I didn't mind that so much. My real worry was that Caroline would have told her to do something horrible to my hair to make me look ridiculous, as some twisted form of punishment. Fortunately, my roommate wasn't holding a grudge after all, and Karen only trimmed my bangs as usual.
On Wednesday night, my parents drove up to the estate for the Thanksgiving holiday, and I was there with Bob and Jenny to meet them. I had asked Jenny for help with my wardrobe, and she suggested that white goes with everything, so I wore a white dress with my yellow hair.
Mom looked at me and said, "Andy, you're blonde!"
You can't put anything past my Mom. "Yes, that magazine editor thought I might try a new look, so I went along with it."
"Well, it's certainly attractive," she said, and then went off to offer Jenny some unsolicited advice about how to stuff and cook a turkey.
"Your hair is very pretty," Dad said. "Does Caroline like it?"
I shrugged. "As far as I can tell. But she's a girl, and I never really know what she's thinking."
"And you never will, so don't let that bother you!" he said.
The following morning, Nigel and Caroline showed up. Bob was working with Jenny in the kitchen, and Caroline went to see if she could help them. My parents had gone out to relax at the pool, and with everyone else busy, I went to chat with Nigel.
"Good to see you again, mate!' he said, looking very pleased with himself. "Caroline said you wanted to ask a favor of me!"
Of course she did. "Um, yeah, I did something to get on the wrong side of your sister-"
He couldn't help but laugh, and said, "By now you should know better than to do that!"
I nodded. "Yeah, I kinda figured that out, but you know what she wants me to do, so can we get this out of the way now?"
He just said, "Lead the way, mate!"
So I took him into our utility closet, and got down on my knees as he unzipped his pants. At least he wasn't going to make me beg for it. His dick was already half-erect, and I started sucking on him as fast as I could. I just wanted this over; I did NOT want my parents wandering back into the house while this was going on! His dick grew in my mouth, and he started spurting. As he pulled out, he got some on my face, but I was glad it was over.
"Always glad to help, Andy!" he said, opening the door to go. "But you might want to clean up before you go back out there."
There weren't any mirrors in here, so I just wiped a paper towel all over my face, as best I could. Then I crept outside, and headed for the nearest bathroom to clean up and wash this taste out of my mouth. And I ran smack into Caroline.
"Um," I said.
She looked at me, reached into her pocket, took out a tissue, and wiped off the side of my cheek. As I stood there turning red, she just looked down at me, grinned, and said, "We've only been here five minutes! You couldn't wait, could you?"
"I did what you told me," I said.
"Of course you did, sweetie," she said, patting me on the head like a puppy. "That's why I like you so much!"
Well, at least she liked me. That probably meant she wasn't mad at me. The rest of the Thanksgiving holiday went well. My parents were glad to see that I didn't look like I was starving, I was doing well at school, and our swim team was winning. I watched a football game with my Dad, but I had given up on explaining football to Nigel and Caroline. I had tried that last year on Thanksgiving, and I might as well have been speaking Greek.
Chapter 8 I Dream Of Sissy
The following week, I received a text from the tech billionaire requesting the honor of my presence on his yacht for the weekend. Wondering what fresh new Hell awaited me there, I texted back my RSVP to confirm.
Friday night, my car parked itself at the marina, and I walked up to the security guard in front of the yacht. It was a different guard this time, but it didn't matter. I sighed as he stepped aside to allow me on board, thinking that by now all of them must know who I am, what I am, and why I'm here.
This time Silvers himself was the first one to meet me. I thought that was odd until I saw the bulge in his pants. "Andrea, how good of you to come!" he said, with a smile that somehow looked sinister to me. "Follow me to my private quarters."
Like I really had a choice about coming here, I thought, and followed him. It was only a short walk, and as soon as we were were inside, he told me to get down on my knees. I did so, and barely had time to look around the room before his dick was in my mouth. He must have really been horny tonight because it was only a few moments before he was blasting away inside my mouth, holding my head in place, and making me swallow all of it.
"Good girl," he said. "I've really been looking forward to seeing you tonight!"
"Yes, sir," I said, swallowing a couple of times. "I could tell."
"Now Andrea, by now you should have learned that I can be a very good friend," he said, "or a very bad enemy!"
I knew about the bad enemy part of it. There were two boys at the bottom of the ocean who were proof of that. I still wasn't sure about him being a friend. "Um, sir, what happens if we're friends?" I finally dared to ask.
"Didn't my magazine publish a very nice story about you?" he asked. "If you play your cards right, you can make the right friends, and there are other ways we can promote you."
I still didn't see how he was going to help me, or even why I would need his help. I already had lots of money, and here I was on my knees every month being prostituted for him and his friends. But I figured he would explain it to me when he was good and ready, so I just said, "Yes, sir."
He just told me to get some rest tonight, because we were making another video tomorrow. Then Watkins came by, took me down to my favorite canopy bed, and tied me down for the night. I fell asleep thinking that for me, this was a normal weekend here.
The next morning, I was in the salon with their hair stylist working on me. "Andrea, your hair has so much volume, this is going to look wonderful!" she said, as she wound my hair around and around.
It wasn't until she finished that I found out what I looked like. She had piled my hair up into this giant beehive hairdo that had been popular with pop singers back in the 1960's. "Um, thanks, I think," I said. "Why am I supposed to look like this?"
"You'll see," she said, patting me on the shoulder. "I'll call Miss Watkins and she will explain everything."
Watkins took me to lunch, gave me a copy of the script of the video they were going to make, and told me to memorize my lines.
I knew immediately from the title, "I Dream of Sissy" that this production was unlikely to win any academy awards. But I read it over and over, and learned my lines.
They got me dressed in a red and pink harem girl outfit. I had a halter top that barely covered my breasts, and my flimsy see-through pantaloons were no better. They placed a headpiece on the beehive hairdo, a pink veil was draped over my face, and they brought me into a larger room.
A man dressed in a blue military uniform started rubbing an antique lamp, and then there was a puff of smoke.
That was my cue. I ran up to him, fell to my knees, pulled the veil down below my chin and said, "You've freed me from the lamp! You're my new master, and I will do anything you want!"
"Are you really a genie?" he asked.
"Yes, I am Sissy, and I've been trapped in that lamp for five hundred years!"
"Your name is Sissy?" he asked. "Is that short for something?"
"No, Master, I'm called Sissy because I'm a sissy!" I said. "I've been dying to suck a man's cock for centuries! Can you please help me, Master?"
Yes, I really said that. I'm just the actor, I didn't write the script.
"All right, Sissy, I can help you with that," he said, and started unzipping his pants.
So I gave him the blow job, and even though it was just as disgusting as ever, I licked my lips and said, "Master, could I have more?"
"Uh Sissy, not right away," he said. "I mean, it's going to take me some time-"
"But Master must have friends!" I interrupted him. "Master, please! I've been waiting five hundred years, I must have more cock!"
"Well yes, I have friends-" he started.
"Master, please call all of your friends!" I begged, looking up at him. "I want to suck ALL of their cocks! Sissies can never have enough cock!"
"Certainly, Sissy!" he said. "Just wait a minute, and I'll have my friends come over!"
There was a pause in the action, and I wondered what my parents would think if they ever saw this video. Me on my knees, in this outfit. I think I blushed almost as red as my costume.
Then a dozen guys showed up. Master's friends, as I had asked. I had to suck all of them, but at least I wasn't tied up. When it was over, Watkins said, "I think the guys will like you dressed up as a harem girl. We may want to make a sequel."
"I can hardly wait," I said.
Afterward they untangled my hair and brushed it out, and then left me alone for the evening. I could only imagine what more fun they had in store for me tomorrow.
The following morning, I found out what they had in mind. They gave me another script to read for my next video. After lunch, they took me down to the pool. Watkins handed me my costume. A string bikini. Part of it, anyway. All I saw were little triangles of white cloth tied together. "Where's the rest of it?" I asked.
"That's all you'll be wearing," she said.
"I've heard of topless swimsuits, but never a bottomless one," I said.
"Andrea, of course there's a bottom!" she said. "But we're going to use it to gag you!"
"I should have known," I said, because that was in character with everything else they have done to me on this yacht.
So I dressed in the bikini top, she tied my wrists behind my back with a rope, and then sat me down on a beach chair at poolside. Then she slid a penis chastity onto me, locked it in place, and tied my ankles together. That's all I was wearing, some ropes, a bikini top, and a steel tube on my penis. As a final touch, Watkins pulled the bikini bottom through my mouth, and tied it off behind my neck.
Now I was getting a little nervous, as two big guys in swimsuits carried me into the water, and stretched me out on an inflatable red-and-white raft. I didn't know if they were going to dunk me or waterboard me, but for now at least I was safe on the raft.
"Andrea, can you say your lines through that gag?" Watkins called out to me.
"Yes, Ma'am," I yelled back. This gag was just for show, not to keep me quiet.
"All right then," she said. "Whenever you're ready."
I struggled against my ropes, twisting from one side to the other, and screamed, "Help! Someone please help me!"
"Are you OK?" one of the big guys yelled back. "What happened to you?"
"Sir, please help me!" I yelled. "A little girl beat me up! Then she tied me up and left me here in the pool!"
The man waded out into the pool toward me. "A little girl beat you up?" he asked.
"Yes, sir," I said. "I'm just a sissy! Girls are much tougher than me. She beat me until I cried, and then she tied me up!"
"Oh, I get it now," he said. "Well, don't worry, sissy! I'll save you!"
Then he turned and called out to the other guy, "Throw me that chain!"
A chain was thrown into the water, he grabbed it, and then swam out to me. Then when he reached me, I saw that the chain ended in a hook. He used it to attach the chain to a ring on my penis chastity.
That wasn't in the script. I expected him to carry me out of the pool. Instead, he swam back to the shallow end of the pool, and climbed out. Then he and the other guy started pulling on the chain!
I flailed with my bound limbs and screamed as they tugged on my poor penis, and dragged me the length of the pool by it. I don't know whether this should be considered bad engineering, or a bad plot device, but I was not happy by the time I reached the end of the pool. Still, the show must go on. If I messed up, I knew they would just make me do it again, and I really didn't want that.
He scooped me up in his arms like a baby, pulled the gag from my mouth, and said, "You're safe now, sissy!"
"Oh, thank you so much!" I said. "I was hoping a big strong man would rescue me, because with my tiny sissy brain, I would never have known what to do!"
"I understand," he said. "After all, you're blonde. You couldn't possibly know what to do, now could you?"
"No, sir!" I said. "There was no way I could have gotten out of that all by my little self! How can I ever thank you for rescuing me?"
"I can think of a way," he said, and gently placed me on my knees on a foam kickboard. "Would you like to give me a blow job?"
The size of the bulge in his swimsuit was frightening, but I had to smile as best I could, and say, "Oh, yes sir, I'd love to!"
He turned to his friend, and said, "Get the other guys."
Then he dropped his swimsuit, his dick sprang out, and I said, "You're so big! I can't wait to get you in my mouth!"
"I'm a big guy!" he said. "Didn't you expect I would be big all over?"
"Oh, you're right, I should have known. I mean, I'm so small because I'm just a little sissy, so I should have guessed that you'd be so big! Please don't make me wait any longer!"
Then his big dick was in my mouth, and it got even bigger. I choked on it a couple of times, but he let me stop and catch my breath, and then he spurted over and over, and made me swallow all of it.
"Thank you, sir," I said, swallowing the salty taste. "There's nothing a sissy likes more than a big dick!"
"Then you're in luck today," he said. "Because my friends are back!"
I turned to see that five more guys in swimsuits had arrived at poolside. All of them made me swallow, because I told them that's what sissies like me love to do.
At last it was over, and I knelt there with that taste in my mouth, hoping Watkins got what she wanted, and I wouldn't have to do this again.
Then she walked up to me, and said, "Andrea, that was excellent! I think you're a natural at this!"
I should probably be insulted by that, but I decided to take it as a compliment for many reasons, not the least of which was that I was tied up and naked with a penis chastity on me, that I really wanted off me. So I said, "Thank you, Ma'am."
At least they were done with me. They hadn't beaten me, or tried to drown me, and to be honest, I'd had much worse weekends on this yacht. She unlocked the penis chastity, untied me, and sent me off to get dressed, have dinner, and go home.
After I ate dinner, I didn't go directly home. I was tired and worn out from the day's abuse, so I went up on deck and plopped myself down on a very comfortable reclining lounger, and looked out over the ocean. I pondered that his yacht would be a really nice place to spend a weekend if it didn't involve being abused over and over.
Then to my great surprise, Mr. Silvers sat in the lounger next to me. I expected he wanted a blow job; I mean, what else was I good for? But instead he said, "Andrea, today's video was very entertaining. I think you're getting better and better at this!"
I guessed that was a compliment, and eventually I said, "Um, thank you." Then after a few moments, I added, "Sir, may I ask a favor of you?"
His eyes narrowed as he looked over at me. "Who do you want me to kill now?"
"What?" I asked.
"The last time you asked me for a favor, I had to kill two boys," he said.
I shook my head. "Oh, no, no! Nothing like that!" I said. "It's just that I've wanted to learn how to surf for a long time now."
He shrugged, and asked, "What does that have to do with me?"
"Um, it's just that every time I've tried to go somewhere to ask about surfing lessons, some of your goons would kidnap me, and I haven't even gotten in the ocean yet."
"Goons?" he asked. "You mean the Australians?"
I nodded, thinking maybe goons wasn't the best choice of word. Maybe I should have said henchmen or thugs, but I don't know if that would have been any better.
"Actually those 'goons' don't work for me, they work for one of my associates, a woman of considerable skills, who prefers to remain anonymous."
"Well, whoever they are, I think they're watching me all the time, and I'm afraid to go anywhere."
"I see. I'll tell you what
next spring or summer, when the weather is warmer, I'll find a place where you can learn to surf."
"Thank you, sir," I said.
"And you'll even get to make some videos at the same time! Surfing Sissy, or maybe Sissy Surfer Girl. I'll have Miss Watkins brainstorm some ideas, I'll sure she'll come up with something that will suit you!"
"Thanks," I muttered.
But he just laughed, and said, "Be careful what you wish for, Andrea
because you might just get it!"
So I thought maybe something good had come from this weekend. I went home, and Caroline was waiting for me when I got back to the room. This was the first time since I had become her slave that I had come home after a weekend on the yacht. I really didn't want to play any bondage games with her tonight, but it wasn't my decision to make.
"Andrea, did you have a good time on that yacht?"
"Yes, Miss," I said mechanically.
She got right in front of me, and took a good look at me. "You look like you could use some rest," she said. "Get to bed!"
"Thank you, Miss," I said. That's why I liked her so much. She put up with all of my nonsense, and she was still a good friend. But she made up for it over the next couple of nights. She decided that with blonde hair, I looked even more like Sailor Moon, and I spent the next two evenings dressed up as such, bound and gagged at her feet.
Chapter 9 Bad Sissy
Now Christmas was coming up, my parents were coming to spend the holiday, and I had once again invited Caroline and Nigel to our estate.
"You need a new dress for Christmas," Caroline told me.
"Why can't I just wear that red thing you made me buy last year?" I asked.
"Because you wore it last year!" she said, as if that explained anything.
I was still wondering whether party dresses explode or somehow disintegrate if you try to wear them a second time when she dragged me to a dress shop in town. After I tried on a half-dozen dresses, she found one she liked.
I stared at myself in the mirrors. I was wearing a white knee-length dress covered in lace. It fit well from my large breasts to my narrow waist, but then it flared from the waist down, thanks to stiff petticoats extending out in all directions. "Will I even fit through the door in this thing?" I asked her.
"It's not that big," she said. "Try swishing your skirts."
"And how do I do that?" I asked.
"Just swivel your hips back and forth."
I did so, and watched in the mirror as my skirts swished back and forth.
"That's it. If you do it slower, you'll be more graceful," she said. "Also try smiling while you do it. You're supposed to having fun, all dressed up in a pretty outfit."
So I did it more slowly, and presumably more gracefully. Somehow Caroline, who almost always wore bluejeans, knew how to do this and I didn't, but then I figured this must be some innate skill that real girls take for granted.
"How do you sit down in this thing? How do you pee in this thing?" I asked.
She just huffed, and said, "We'll get to all of that later. Just buy the dress, it looks nice on you."
My parents showed up on Christmas Eve, and Mom loved my new dress. Of course she made me prance around in it, so my new skirt-swishing skill came in handy. Actually that would turn out to be valuable knowledge, but we're getting ahead of ourselves. The holidays went well, and my parents never suspected I was leading a double life. Student-athlete, except for one weekend a month spent as a sex toy on a super yacht.
In January I was back at school, and inevitably came the text inviting me for a weekend on the yacht. I accepted, and told Caroline I would be gone for the weekend.
"What do you do on that yacht? And who are you doing it with?" she asked.
"You don't want to know. But I'll be back Sunday night. I think," I said, wondering what Silvers and his associates had thought up for me.
Friday night, I arrived at the marina, wearing my usual blouse, skirt, and heels. Silvers must have been really busy. He barely had time for me to give him a blow job, and then told me I would be making another video tomorrow.
The following day, Watkins told me we were going to have a fashion show. "We're going to model clothes?" I asked.
"No, YOU are going to model clothes," she said. "We're going to make a video about a sissy fashion show, and it's all about you!"
I stifled a groan. If Caroline made me do something like this in our dorm room, I might enjoy it. But I never got aroused on this yacht because I was always so nervous about what might happen next. I expected to be walking around in some ridiculous outfits with my boobs hanging out all day long. I assumed I was going to be the star of a video called, "Scantily Clad Sissy" or something similar. But I was wrong (again.)
Watkins took me to a small room adjacent to the long narrow room I had been made to crawl through with a wand stuck up my butt as I had to blow kisses to the crowd. Just walking through that room, even fully clothed, still made me shudder.
She had me strip down to my underwear, and then laced me into a corset. A boned corset that felt really tight, and made my narrow waist even narrower. Then the hair and makeup women brought in a pink dress for me. A HUGE dress. There were layers and layers of it. It looked like something women might have worn in England two hundred years ago.
"What is that?" I asked.
"This is a hoop dress," Watkins said. "I think you'll look very pretty in it."
"Can I even walk in that thing?" I asked. "It's so long
how do I keep from tripping over it?"
"You need to take small steps," she said. "Let's get this on you."
Then the dress was draped over my head, and billowed out all around me down to my ankles. I looked like Cinderella on her way to the ball. "OK, so what do I do now?"
"Now you walk slowly and gracefully the length of that room, turn around, smile, and walk back here," she said. "That's all for now."
I looked at the door, looked down at the width of my dress, and asked, "How do I fit this dress through the door?"
"Just pull up the hoops on one side of your dress, and let them back down once you're through the door. Now go!"
"Yes, Ma'am," I said. I pulled up the hoops on the right side of my dress, squeezed through the door, and let my dress fall again.
There were men seated all along both sides of the room, and photographers pointed their cameras at me. I took as deep a breath as the corset would allow, and slowly walked out into the room. Mercifully, the men didn't mock me or hurl insults at me as I walked through the room. I made it to the end of the room, turned around as gracefully as I could, swiveling my hips as Caroline had taught me, smiled, and headed back across the room. I slowly retraced my steps, and as I lifted my hoops to fit through the doorway, one of the men called out to me, "Andrea, you sure are a pretty little sissy in that get up!"
That startled me, and I blushed as I squeezed through the door.
"Very nice, Andrea," Watkins said. "Where did you learn to swish your dress like that?"
"Um, my girlfriend taught me to do that," I said.
"Oh, that's nice that your girlfriend is helping to sissify you," she said.
I just stared down at the floor, but I'm sure I blushed even redder.
"But with a long dress like this, you can look even more sissified if you lift your skirts a bit, and then keep swishing them as you walk all the way down there and back."
Then she demonstrated the swishing motion on her own skirt. I just frowned and said, "Yes, Ma'am."
As I turned to go, she said, "Andrea, let's turn that frown upside down! Remember to smile!"
"Yes, Ma'am," I said.
So I squeezed through the door again, and tried to smile as I started swishing my dress back and forth. A few of the men burst into laughter, and it wasn't long before the entire room was laughing at me, and I had to mince my way across the entire room with this stupid smile plastered on my face. Then I had to turn and walk back again, and I could feel my face turning bright red. As the men yelled some more rude comments at me, I couldn't run or even hurry in this dress, but I finally swished my way across the room and squeezed through the door again.
As I tried to catch my breath, Watkins said, "That looked like fun, Andrea. Didn't you have a good time modeling that pretty dress for us?"
I was afraid that if I said no, she would send me out there again, so I just mumbled, "Yes, Ma'am."
"Good, then let's get you out of that dress and into something else," she said. "Have you ever heard of Lolita fashion?"
"No, Ma'am," I said.
"Oh, I'm sure you'll love it!" she said.
Actually I didn't love it. She dressed me up in one frilly outfit after another, and made me parade around in front of a bunch of guys who were getting raunchier and more lewd with each frilly costume I wore. At least there were only about a dozen guys here this time, not nearly as many as last month. These costumes had to be designed to make me look ridiculous.- Every blouse was full of ruffles and frills, and every skirt billowed out from my waist. I always had something on my head, whether it was a bonnet, or a hairband with a big bow or a flower in it. Sometimes I wore these lacy little gloves that were fingerless, just to show off my red nails. When my outfit would permit, I had to curtsy as I smiled at those jerks, even as they laughed at me.
After about a dozen of these Lolita outfits, Watkins asked me, "Would you like to stop now, and give them blow jobs?"
I desperately wanted this to be over. I had expected to be wearing underwear or maybe a bikini, and I had no idea how embarrassing being fully clothed could be. "No more modeling these outfits then?" I asked.
"Unless you'd rather continue," she said.
I was wearing a pink and white ball gown. My chest was covered in white ruffles, with a big pink bow at my waist, and everything was trimmed in lace. My pink princess dress was knee-length, and I wore white socks with pink bows. I looked like a girl from a cartoon. "Yes, Ma'am," I said. "This seems like a good time to stop."
"All right then, go out there and get down on your knees, and tell the guys you want to give all of them blow jobs!"
"Yes, Ma'am" I said, and slowly walked out into the room again to face the inevitable. I got down on my knees, faced the men on one side of the room, and said, "Could I give you guys blow jobs?"
"What's that?" one of the guys asked, as he headed toward me. "I'm not sure I heard you!"
Then a couple more guys headed toward me. "I think Sissy Andrea wants to give us blow jobs!"
The guys behind me against the other wall must have heard that, and one of them called out, "What's going on? The little sissy wants to give blow jobs?"
Now they were all crowding around me, unzipping their pants. These guys didn't want to wait in line, and suddenly I had two erect dicks in my face!
"Guys, there are so many of you, and only one of me!" I said. "Please, one at a time!"
But they didn't back off. One guy got his dick in my mouth, and everyone else still crowded around me as I worked him in and out of my mouth. And as soon as I was done, and had a mouthful of cum, another guy took his place. And another and another, until all of them were done with me. I just stayed there on my knees with that salty taste in my mouth, just wishing this day was over.
"Very good, Andrea," Watkins said.
I looked up to see her standing over me, and all of the men were gone. "So now what do I do?" I asked.
"You're free for the rest of the day. Get cleaned up and have dinner," she said. "This was a very productive day for my magazine."
"For your magazine?" I asked.
"Oh yes, you looked lovely in those outfits," she said. "I think we may do another feature story on you, showing just how adorable a transgirl can be when she gets all dressed up!"
I tried not to groan. I wondered what my teammates on the swim team and the other kids at school would think if they saw me parading around in those outfits.
At least the food was good here. I went to dinner in the dining room, and the chef came out to ask me what I wanted. I just asked for a cheeseburger and a Coke, and then I wondered what they had in mind for me tomorrow.
The next day, Watkins took me through the long narrow room into a small adjacent room, and pointed to a pair of scissors lying on top of a stool. "You may find those useful," she said. Then she took me back through the long room into another room on the other side, where the two photographers were waiting.
"Are we making another video today?" I asked. At least I was dressed in normal clothes today, a white blouse, blue skirt, and white high heels.
"Yes, of course," she said. "Now put your hands behind your back."
I did so, and felt ropes tying them together. Then she sat me on the floor, tied my ankles together with more rope, and held up a penis gag to my mouth. As soon as I opened my mouth, she slipped it in, and tied it off behind my neck.
"Andrea, we're going to make a video of you struggling and trying to escape from this. You know where the scissors are, so get up! The sooner you get free, the better!"
I couldn't say much of anything with this gag in my mouth, so I just groaned. But she left me alone with these two guys pointing their cameras at me. It was all I could do to roll over against a wall, rub up against it, and finally get my feet under me. It took a long time just to get up on my feet. I didn't want to try to hop on these high heels, so I just took baby steps with my ankles bound. I hobbled over to the door, and now there was a problem. This room was one step higher than the long narrow room. I would have to hop down into the other room. I just stood there looking at the photographers, pleading with my eyes. But they just kept recording; these guys weren't here to help the tied-up little sissy.
So I tried to take a deep breath around the gag, and jumped down in to the next room. But I hopped too far, landed off balance, and screamed as I toppled over face-first. I turned my head just in time to keep from breaking my nose as I hit the floor. I just lay there on the floor, and could barely see the photographers standing over me, up through a veil of my hair draped all around my face.
I decided that was enough. I was just going to lie here on the floor until someone came along to collect me. They could have enough fun watching the video of my face plant. I wasn't going to give them any more entertainment by getting myself killed. The ropes weren't really uncomfortable, so I lay there face down on the floor, and waited.
I don't know how long I was there. A half-hour, maybe an hour, before I heard someone else come into the room. The photographers came and went, and then a folding chair was set up next to me. Then someone grabbed me, and picked me up; this felt like a girl!
She sat on the chair and threw me across her lap. Then she pulled my skirt up, and my panties down, exposing my butt, and said, "It looks like Andrea needs to learn a lesson!"
I looked up, and she pulled my hair back so I could see her. Oh no! It was that awful teenage girl, the one they called Brittany. Then I felt a sharp pain in my butt, and then another one!
"How do you like the feel of this paddle?" she asked. "I think the wood will make your ass nice and red, don't you?"
I just groaned, and shook my head, but she just hit me again and again. After about a dozen blows, my butt was starting to burn when she finally stopped.
"That's a nice color, sissy boy," she said. "Take my word for it."
I just whimpered into the gag, but there was nothing I could do. Then I felt her fingers spreading something into my butt, and I tried to scream.
"Relax," she said. "You've already got one dick in your mouth, so I'm sure you want one in your ass too, right?"
I tried to scream and shake my head, but then I felt something pressing into my butt. Being tied up like this, she couldn't even spread my cheeks, but the plug (or whatever it was) was pushing into me anyway. I tried to squirm, and clawed at the air with my fingers, but it went all the way in, and then my butt closed around it.
"Oh, stop complaining, I know you fags love being fucked like this!" she said. "Besides, it's just a small plug, so stop acting like a baby!"
I tried to say a few choice curse words to her, but I just ended up groaning into the gag some more.
"What's that, faggot? It sounds like you wish the plug was bigger?" she said. "Don't worry, I can do something about that. I'll just squeeze this bulb a few times."
Bulb? I wondered. But then the thing inside me started growing! Oh God, this wasn't a regular plug, and that bitch was inflating it! I screamed and screamed as it pressed against my insides. Then she shoved me off her lap onto the floor.
"Maybe you'd like some alone time now," she said, and pulled my ankles up to my wrists. As she tied them together in a hogtie, that made the plug press even further into me. "Now don't you look adorable? A cute little sissy, sucking and fucking. I know some other fags who would love to have a good time with you! Maybe next time, I'll bring them with me. Or better yet, I'll tell them where to find you at your school!"
I just lay there at her feet, whimpering. This bitch was bad enough, I really didn't want to meet any of her friends.
Then she grabbed a handful of my hair, and pulled me up on my knees. "Next time you come to this yacht, would you like to meet a couple of fags?" she asked me. When I didn't try to answer, she slapped my face hard enough to make it burn and knock me over on my side.
I just moaned into the gag, and she pulled me upright by my hair again, and said, "I can't hear you, faggot!" The she slapped me again, knocking me over. She pulled me upright, and lifted my chin to make me look up at her.
I just shook my head and whimpered, my cheek on fire.
"Then from now on, sissy boy, you better do as you're told," she snarled at me, and shoved me face down on the floor.
I heard her walk away, and after a while, the photographers left. At least they were done recording my beating and humiliation. I lay there face down for quite awhile until I heard someone approach. I was dreading whatever would happen to me next, when I was gently pulled upright on my knees. Watkins crouched next to me, and started untying my wrists. She said, "Get cleaned up, have dinner, and go home."
She left me to finish untying myself and getting the toys out of my orifices. It took me a while, but I finally got loose. Both my butt and face were a little sore, but to be honest, I've had worse beatings. By the time I got to the dining room for dinner, it was late, and as usual it was empty. But this time, instead of the chef, a young man dressed as a waiter came out to see me.
"Oh, hi," I said. "Can you take my order?"
"I know what you want," he said. "It's no secret what a slut like you wants between your lips, and it's not on any menu, is it?"
I just stared at him, my mouth open.
"What, don't you think everyone on this yacht knows what you are?" he said, and then grabbed a handful of my hair, and jerked my head back.
"Ow!" I said, trying to pull away from him.
"Get up, slut!" he said, pulling me up to my feet by my hair. "I'm going to take you into the kitchen and give you an appetizer!"
"OK, OK," I said, as he dragged me away into the kitchen.
When he dragged me into the kitchen, no one else was there, and he shoved me down on the tile floor. "Get on your knees so you can suck my cock!" he snarled at me.
"All right," I groaned as I massaged my scalp where he had grabbed my hair.
By the time I got back up to my knees, he had already unzipped his fly, and shoved his dick in my mouth. As it grew in my mouth, he wrapped both of his hands around the back of my head, and slammed his dick into me over and over until he started spurting. The salty tasted filled my mouth, and he made me swallow all of it before he let go of me.
"I hope you enjoyed your appetizer, slut!" he said. "Now get back in the dining room!"
I dragged myself up and back into the dining room. And now I was just supposed to sit here with this taste in my mouth, after what the waiter had just done to me?
A few minutes later, the chef showed up. "Andrea, I understand you've already had an appetizer," he said. "Would you like to order something else now?"
"Um, could I please have a cheeseburger and a Coke?" I asked, wondering what else might happen to me here.
But he just said, "Of course!" and disappeared back into the kitchen.
Fifteen minutes later I had my burger, I ate it as fast as I could, and then hurried to leave the yacht. Watkins was waiting for me up on the deck.
"Andrea, I understand you were served an appetizer that you didn't like," she said. "Perhaps next time you'll make more of an effort for us?"
So that's what this was all about? "Yes, Ma'am. I promise I'll do better next time," I said.
"I hope so, for your sake. The Australians like to see videos of you tied up and struggling. But what they like more than anything is to see you being beaten," she said. "Just something to keep in mind when we see you next month."
I swallowed, nodded, said goodbye, and hurried to my car for the trip home. On the ride home, I told myself that the next time I was on that yacht, I would do whatever they told me to do, no matter what it was. Then maybe they wouldn't let that girl Brittany get her hands on me.
Chapter 10 The Stick
Later that month, we had another swim meet, which we easily won, and then I had nothing to worry about until my February weekend on the yacht. That's what my life revolved around now. The occasional swim meet, going to the salon every few weeks to have my dye job touched up, and then who knows what kind of a monthly nightmare on that yacht. Otherwise, I dressed like a proper young schoolgirl, wearing skirts, blouses and boots, with my various accessories; earrings, necklaces, bracelets. My two lives intersected in the evenings, when Caroline would tie me up, but that was just for fun.
Then at the end of the month, I got the text asking me to come out to the yacht for the weekend. I hesitated for a moment. I could put this off for a week or two, but there was no avoiding it. This had always been in the back of my mind, as I went to class, and when I did my homework and swam laps. Even the swim meet had been secondary; I trained hard and I knew I could beat those kids in my sleep. But I wasn't as interested in impressing my teachers or parents or swimming coach as I was in satisfying the people on the yacht, who could beat me (or even kill me?) if they got mad at me. So I texted that I would be there.
I wanted to look my best, so I wore a white dress and high heels when I went to the marina for my February visit. My bright red nails were perfect, and I really hoped to make up for getting them pissed off at me last month.
Watkins was there to meet me, and just pointed me toward Silvers' room. I went in, and found him standing there alone.
"Sir, I'm sorry about last month," I said. "Please forgive me, I know I can do better."
"For your sake, I hope you're right, Andrea," he said. "You can start by asking me if you can suck my cock!"
So that was the way this weekend was going to be. No small talk, no foreplay, just start right in. But I had been well trained during my year as a slave in Australia, and I knew how to abase myself completely. This wasn't something I had never done before. I got down on my knees, and looked up at him. "Sir, I'd like very much to give you a blow job," I said. "May I please suck your cock?"
"Be sure and swallow all of it like a good little slut!" he said, unzipping his fly.
"Yes sir, of course," I said, just before he shoved it in my mouth.
His dick swelled as it slid in and out of my mouth, and soon he spurted over and over. Somehow I could never get used to the salty taste and the goo filling my mouth. But I just looked up at him and smiled.
"Andrea, do you expect me to put this sticky thing back in my pants?" he asked me.
"Oh, no sir!" I said. I licked it clean, and then kissed the head of his dick. "Thank you so much for letting me suck your cock! I'm a sissy, and there's nothing I like more than sucking cock!"
"I'm glad to hear that," he said, zipping up his pants. "Then you're going to have a lot of fun this weekend!"
I spent the night as usual, chained up with leather cuffs on the canopy bed. The following morning after breakfast, Watkins took me back to the bedroom and told me to get undressed.
As I stood in front of her naked, she handed me a pair of white high-heels, and said, "put these on, and then turn around with your hands behind your back so I can tie you up."
"Yes, Ma'am," I said. As I put on the shoes, I remembered thinking this day didn't look promising. Then I felt ropes binding my wrists behind me. As usual, snug but not real tight. Then a collar went around my neck. It was pink, with the word "SISSY" written on it, and she attached a leash to it.
Then she tugged on the collar, and pointed toward the door. "Let's go, Andrea!" she said. "It's show time!"
I walked out the door, hoping this was just going to be a photo shoot of me in my birthday suit. But she marched me out into the long narrow room, not only were the two photographers there, but I also counted twelve men sitting in chairs, six on either side of the room. Some of them wore polo shirts and shorts, others were in dress shirts and pants. Then Watkins tugged on the leash, and led me up to the two rows of men. I was going to have to walk through the gauntlet of all of these men, naked and bound.
As I started to walk between them, the first man on my left grabbed me around the waist, picked me up, and sat me on his lap. "Lucky me!" he said. "I get first crack at the sissy's crack!"
I heard him unzip his shorts, and already I could feel his dick bulging out. Then he smeared something into my ass that made me gasp. I tried to lean forward to get away, but it was hopeless. He just grabbed the leash and pulled me back to his chest.
"Little sissy has a nice sized butt hole!" he said. "Maybe this won't hurt so much!"
I tried to turn to face him. "Sir, please don't-" was all I got out before a large hand squeezed my mouth shut. I looked up to see another man standing over me.
"Andrea, they told us you would behave yourself, and do as you're told!" he said. "You ARE going to be a good little sissy, aren't you?"
"Yes sir," I managed to say. But the other man's started pushing into my ass, and made me groan as I squeezed my eyes shut. When it finally stopped pushing, I gasped and opened my eyes, only to find another dick pointing at my face.
"You can take both of us at once, can't you, Andrea?" he asked, with a wicked smile that made me cringe even more than the dick up my butt did.
"Yes sir," I said, and he shoved his dick in my mouth. I had one guy with his arms wrapped around my waist, bouncing me up and down, while the other guy grabbed a handful of my hair, and slammed his dick into my mouth over and over. I felt like a rag doll, being thrown back and forth, choking on one cock while another one forced its way into my ass over and over. Finally both guys came, leaving me with a salty mouth full of goo, and my aching butt suddenly felt empty.
Then one of the guys asked me, "Did you like that, sissy?"
I just groaned and licked my lips, trying to get rid of that taste. Then he slapped one of my breasts hard. I just gasped and bowed my head, and tried to pull away from him.
But he just lifted my chin and said, "I asked you a question, did you like that?"
"Yes sir," I cried out. "I liked it!"
"Good!" he said. "Because now you can take care of my friends, too!"
Then the guy who had just raped me lifted me up, and handed me to the man sitting next to him. He was already hard. And the guy sitting across from him had already gotten up and was unzipping his pants. All I could think was that I had to do this five more times.
By the time the third pair of guys were done with me, my butt ached and I had tears spilling down my cheeks. But they didn't care; it just made them laugh at me more. They started slapping my face, my breasts and my butt cheeks, which only made me cry even more, but there was no escape for me. I was tied up and they were going to do what they wanted. As each new guy started raping me he would ask, "What's the matter, sissy, can't you take it?" or "Are we bigger than your boyfriends?"
When all six pairs of men were done with me, they left me lying on the floor, tied up and naked, sniffling and trying to stop sobbing as my tears spilled onto the floor. Then only the photographers were left, and they stayed on the job, recording every second of my abuse and humiliation. All I could think was that maybe Silvers would be satisfied with me now, and I hoped he wouldn't want to hurt me any more.
Eventually Watkins stopped by. But she didn't untie me. Instead she bound my ankles with rope, and then bound them to my wrists in a hogtie. Then she shoved a penis gag in my mouth, and tied it off. "Andrea, now you can relax," she said. "Take the afternoon off."
She left me there for the entire afternoon. My butt really ached, and I had to spend most of the day hogtied on the floor with that penis gag in my mouth. When she finally untied me, and told me to go have dinner, my wrists and ankles ached, and my jaw was sore from being gagged for so long. Then I stood up, and my butt hurt so much with every step that I had to be careful putting each foot down.
At least the chef gave me dinner that night, and I didn't have to deal with that waiter abusing me again. I hoped that meant they thought I had been punished enough. After dinner, Watkins brought me back to the canopy bed, bound my ankles, and tied my hands behind my back with leather cuffs, and left me in the bed. I thought it was kind of early to be going to be, and she left the lights on, but I didn't care. I was just glad that I could get some rest.
Some time later, Watkins came back into the room, followed by a young man wearing blue pajamas. He looked at me, and asked, "What's this?"
Watkins glanced at me and said, "Oh, I brought you a bed warmer. Something to take the chill off your sheets."
"Ah, something to warm my bed!" he said. "Very thoughtful of you!"
This bed was the only place I had ever slept on this yacht, and I had come to think of it as MY bed. Now I realized how foolish that was. It was HIS bed. He was an important person, and I was just a tied up, naked little sissy put here for his pleasure. I just sighed and wondered when this day would ever end.
He climbed into bed next to me, and all I could think was that I really didn't want another guy using my ass tonight. I started, "I'm Andrea-"
He said, "Yes, I know. I know who you are, and what you are."
Oh, God. Now he's going to use me, too. "Sir, my butt really hurts," I said. "Could I please give you a blow job?"
He's lying there next to me, just looking at me, and I'm wondering what he must be thinking of me. Here I am begging him to let me suck his cock. Finally he said, "You DO have a pretty mouth."
Then he reached behind my head, pulled me close to him, and started caressing my hair. I was lying there, practically nose to nose with him. He wasn't bad looking, and he didn't look like an evil bastard, but that didn't really mean anything.
"You aren't a natural blonde, are you?" he asked.
"Uh, no," I said. "They told me to become blonde."
"And you always do what Mr. Silvers tells you?" he asked.
"Yes sir," I said. I didn't want to end up on the bottom of the ocean.
"Then let's make good use of your mouth," he said. Then he pulled me in and kissed me. A real open-mouth kiss, with his tongue darting into my mouth.
When he let go, I pulled back, my mouth open and eyes wide in surprise.
"Something the matter?" he asked.
"I
uh
I wasn't expecting that," I said.
"Maybe you just haven't kissed properly yet," he said, and drew me in for another kiss.
Another kiss with lots of tongue, and I just closed my eyes and pretended I was kissing a girl. It was better than having to suck his dick, anyway. We spent quite a while making out, and I thought it was only a matter of time before he did what he wanted with me.
What he wanted was to reach over to turn out the light, and then he said, "Good night, Andrea."
I was absolutely shocked. Finally I asked, "That's it?"
In the dark, I could see him turn to look over at me. "I hope you aren't too disappointed."
"No sir," I said. "Good night."
I was going to sleep next to a man who didn't want to rape me. I figured maybe Silvers and Watkins had decided I had had enough abuse for the day, and didn't want to kill me all at once. They could have more fun with me tomorrow.
When I woke up in the morning, my bedmate was gone. I still didn't know his name. After a while, Watkins came in to untie me. Then she marched me onto the deck wearing only my high heels and pink "SISSY" collar. Walking still wasn't a lot of fun, but at least my butt didn't hurt as much as yesterday. It felt so weird walking around naked like this, although the few people I saw didn't pay any attention to me. If I had to be naked, at least it was a nice day up on deck, warm but with a cool breeze.
"I want you to get some sun this morning," Watkins said as she stood me up against a pole, and bound my wrists with leather cuffs up over my head. Then she gagged me with a scarf, and said, "You'll stay here until it's time for lunch. Don't try to speak to anyone, and don't even look at anyone else. Just stare down at the deck and behave yourself!"
I nodded, and she left me alone there. At first, I thought being tied up here for hours was going to be boring. But then I thought that on this yacht, boring wasn't a bad thing. Lots of exciting things had happened to me on this yacht, and none of them were good. So I just stared down at my bright red toenails, and hoped for more boredom.
I almost got the boring morning I wanted. But after perhaps a couple of hours, I heard a couple of people talking. I snuck a peek out of the corner of my eye, and saw a man and woman approaching me, and then looked down at the deck again. Here I was, tied up and on display with my breasts and penis hanging out for all to see.
They walked over and stopped in front of me. "Look at this!" the woman said. "He must not be be able to decide whether he wants to be a boy or a girl!"
"It makes sense," the man said. "Look at his collar. His name is Sissy!"
I just kept quiet and stared down at my toes, but then the man cupped his hands around my breasts, and made me gasp.
"Nice pair of knockers," he said.
Then the woman stroked my hair, and caressed it. "All this hair
it's real, it's not a wig."
Then she traced her finger down my back all the way to my butt, which made me shiver.
"Nice round butt too, but he's very fit. He must work out to keep this hourglass figure."
"He'd look cute in a maid's uniform," he said.
"And the housekeepers would have lots of fun playing with him," she said. "Are you thinking what I'm thinking?"
"We should ask Silvers if he's for sale," he said.
My eyes widened but I tried not to show any emotion. I wondered how these people could think of buying me? Didn't they understand that slavery has been illegal ever since the Civil War, or are they so rich that they think they can do whatever they want?"
"Definitely," she said. "He could please all of the women
and the men too!"
"Oh yeah," the man said. "I wonder how many dicks this little Sissy here has wrapped those full lips around! He must be good at sucking cocks!"
My throat went dry, and I was trying not to shiver and sweat at the same time. But at last these two would-be slave owners wandered off, most likely in search of Silvers to see if they could buy me.
After that, I just stood there hoping they wouldn't return with the news that I belonged to them now. But the only person who spoke to me was Watkins, when she came to untie me. After lunch, she took me down through the long narrow room and said, "Now we're going to try this again. See the scissors on that stool in the next room?"
"Yes, Ma'am," I said, looking through the doorway into the next room.
Then she marched me back through the long room up the step into the other room where last month's debacle started. "Take off your shoes," she said.
I sat down and took my heels off. Then she used some ropes to tie my wrists behind me, then my ankles, and then bound my ankles to my wrists. The ropes were snug, and it wasn't a tight hogtie, but there was no way I could stand up. Finally she shoved a ball gag in my mouth, and buckled it off behind my neck. I was lying there naked on the floor, wearing only my SISSY collar, and the gag was stretching my mouth.
She called for the photographers, and then turned to me. "Andrea, I don't care if this takes all night. You can use the scissors on that stool to free yourself. How you get there is up to you. But if you don't like the feel of those ropes or that gag, then you better not dawdle!"
The photographers walked in, and she rapped a long metal pole on the floor. "If he gets lazy, you can poke him with this as often as needed!" Then she looked down at me and said, "Put on a good show for me, will you?"
Then she left, and they started recording. I couldn't stand up and hop, so I had to roll over to move at all. And that's what I did. I had to rock back and forth until I could roll over on my back. Then I had to do it again until I could roll over on my stomach. It took me a long time just to make it to the door, and already I was sweating and drooling around my ball gag.
Finally I rolled down the step and landed in the long narrow room. It hurt and I had to stop to catch my breath, then roll over a few times as I slowly made my way across the room. At one point I must have stopped for too long because one of the photographers poked me in the stomach with the pole. I screamed into the gag, and looked up at him, but he just laughed and the other one moved in for a close up.
I'm an athlete in really good shape, but these aren't muscles that I normally use, and it took me a very long time to roll across that room. I finally made it into the other room where the scissors were on the stool. Up there where I couldn't reach. My solution to this problem was to roll and bang my legs into the stool over and over until it finally toppled over. At last the scissors were on the floor, and I could get my fingers into them.
Guess what? Scissors aren't really made for cutting rope. I got the scissor blades on the rope binding my wrists and ankles together, and just kept sawing back and forth, over and over. My fingers ached, but the rope finally snapped. I just lay there on the floor, exhausted, sweating and drooling, able to stretch my legs at last.
Then one of the guys stuck me in the stomach with the pole again. I screamed into the gag, and flipped over on my back. My hair spilled all around my face and I couldn't see much of anything
"Hurry up, kid," the photographer said, "or we might have to stick this pole up your ass!"
I groaned into the gag, and tried to get the tip of the scissors into the ropes around my wrists. This was even harder than sawing away at that first rope because I couldn't get the scissors all the way into it. I just kept working away at it for what seemed like forever, until I finally felt the rope snap. I flailed away and felt the ropes around my wrists start to go slack, and finally I was free. Then the pain came back into my wrists, and I groaned into the gag as I tried to massage them. I untied my ankles, and they hurt too, and then managed to get the gag out of my mouth.
One of the photographers left, and I was still sitting there on the floor exhausted, when he returned with Watkins. "Excellent, Andrea!" she said. "Now give both of them blow jobs!"
I sighed and said, "Yes, Ma'am."
They didn't even wait for me to crawl over to them. One of the guys was already standing over me, unzipping his pants. "This is one of the job's perks, dealing with disobedient children!" he said.
He shoved his dick in my mouth, grabbed a handful of my hair, and slammed me back and forth until he came in my mouth, and made me swallow all of it. The other guy was the same. When they were done with me, Watkins said, "Andrea, I hope you've learned your lesson."
"Yes Ma'am," I said. "I'll do whatever you want me to."
"Good. I hope we don't need to have a repetition of this," she said. "Now get dressed, have dinner, and then go home."
"Yes Ma'am," I said. "It won't happen again."
So my long weekend was finally over. After dinner I went home, and I must have slept in the car on the ride back to school. When I got home, Caroline looked at me and said, "Andrea, you look like you got run over by a truck! What do you do on that yacht??"
I just shook my head and said, "it's better that you don't know."
Chapter 11 The Carrot
Spring Break was coming up in March, and I got a text from Watkins, asking me about the first weekend.
I said I would be there, and then she responded by telling me not to make any plans for the following week. I texted my OK to her, and then wondered what I had gotten myself into. A whole week on that yacht? Then I told Caroline I would be gone all of Spring Break, and she wasn't real happy about it. I wasn't happy about it either, but I had to go.
Friday night, Spring Break started, and I drove to the marina, where I was welcomed to the yacht as usual. I didn't know what they would have in store for me, but at least they didn't bother me that night. I drank an iced tea up on the deck, and then I dozed off.
I woke up, stretched, and looked around. I wasn't tied to the canopy bed on the yacht. I wasn't on the yacht at all. I was in a normal bedroom with a nightstand and a chest of drawers. I sat up, dressed in a white nightgown, wondering where I was, and how I got here.
Then Watkins poked her head in from a doorway, and said, "Andrea, you're awake! Aloha!"
"Aloha?" I asked. "Isn't that what they say in Hawaii?"
"Yes, it is," she said. "There's a white swimsuit in your closet. Wear it under the pink summer dress. You're going to the beach today."
"Are we really in Hawaii?" I asked, hurrying over to the window.
"Of course. You said you wanted to learn how to surf, didn't you?"
I looked out the window at a sandy beach and was struck by the turquoise blue water, which I assumed was the Pacific Ocean. "I
I thought I would do that in California."
"You could have, but the surfing is better here, and you don't have to bother with a wet suit, so you can show off that figure of yours!"
I felt myself blushing. I was going to be showing off my figure on a public beach. Then I noticed something, and lifted my nightgown to take a peek. "Um, why is this on my, uh-"
"Your penis chastity? You're going to have to wear that here because we don't want an unsightly bulge in your swimsuit during your surfing lessons, now do we?" she asked.
"OK, yeah, I guess not," I said. "But how did we get here?"
"You see, many years ago they invented something called an airplane," she said.
"But I went to sleep last night on the yacht," I said.
"We gave you something to help you sleep, and you slept through both flights."
"BOTH flights?"
"Yes, we landed at Honolulu, and then an inter-island hop over here to Kauai, so we would have more privacy for you," she said.
Oh
more privacy sounds good," I said.
"I'm glad you approve," she said with a grin. "Now get dressed and come downstairs for breakfast."
At breakfast, she introduced me to Noelani, a pretty teenage girl in a light blue summer dress. She was tall, with an olive complexion and long dark hair parted in the middle.
"Noelani is an outstanding surfer, and she will be your instructor," Watkins said. "Do whatever she tells you, and there's a good chance you won't get hurt too badly!"
I nodded. "OK, not getting hurt sounds good," I said.
Noelani took me down to the beach where we stripped down to our swimsuits, and then I saw the two photographers from the yacht. "Why are the photographers here?" I asked her.
"They're going to make a video of your lesson," she said. "That way we can review it later, and correct anything you did wrong."
"Oh, all right," I said.
"Don't be self-conscious in front of the cameras, just focus on the surfing."
"That won't be a problem," I said. Those guys had made videos of me doing things a lot more embarrassing than falling off a surfboard.
"First of all, you need some sunblock. This is SPF-75," she said, and smeared some cream all over my face and shoulders.
"SPF-75??" I asked. I had never heard of any sun protection factor higher than 30. "What is that like, a sweatshirt and bluejeans?"
"You want to get tan, not red. And as pale as you are, you would burn very quickly here."
That's what I get for spending most of my time indoors, swimming laps in a pool. Then she had me lie prone on a surfboard on the beach, and showed me how to paddle, and when a wave starts to lift the board, how to slide my feet forward to stand up.
"Andrea, if you forget everything else I tell you, remember this! When you fall off your board, you want to fall backwards, not forwards."
"Why, what's the difference?"
"The difference is that you want the board in front of you, where it won't hurt you. You never want the board between the wave and you. Then the wave can can hit you with the board."
"Oh yeah, I didn't think of that," I said.
"That's how surfers drown, by getting hit by something. The waves may swallow you up, but they will almost always spit you out again. But if something hard like a board or another surfer hits you in the head, you can get knocked out and drown," she said. "So you want to avoid that, right?"
"OK, I get it. I'll fall backwards."
I did a lot of falling backwards. People see surfers riding the waves, and they think it's easy. It's not. Noelani makes surfing look easy, but it isn't. It's hard. Just trying to stand up was hard. I hit my chin on the board. I hit my head on the board. When I finally learned how to stand up, I fell off more times than I could count. After a couple of hours of eating seaweed, Noelani had seen enough.
"All right, that's a start," she said. "We can try again later."
"Later today, you mean?" I asked.
"Yes, we can go out again, just before dinner. The sun's getting high in the sky, and we don't want you getting too sunburned on your first day."
I shrugged. My shoulders didn't look red at all but I figured, when in Rome, do as the Romans do. So I went back inside, got showered and dressed again. When I came downstairs, two young women were waiting for me. Miss Hair and Miss Makeup from the yacht were here, too.
"Andrea," Hair said, "Miss Watkins said I need to do some work on you."
"Uh OK," I said.
So she sat me down next to a sink, trimmed my bangs, and then went to work touching up my roots. After brushing out my hair, she finally decided that she was satisfied with her work, and led me to the photographers. "All right, she's yours now!" she said.
They took me to a pool, which was oddly shaped, not quite round, and then I saw why. I pointed, and said, "From this point of view, it looks like the pool goes on forever. It merges into the ocean."
"That's why it's called an infinity pool," one of the photographers said. "It creates an optical illusion because the walls and bottom of the pool are painted so that the water in the pool looks the same color as the ocean. So you can't tell where the pool ends and the ocean starts. It looks like the pool never ends."
"Wow, I thought I knew everything about swimming pools," I said.
"That's why we want to photograph you here," he said.
They took lots of pictures of me, first in my dress, and then in my swimsuit. This was one of those rare occasions where they photographed me with my clothes on. Then as Noelani reviewed the video of my (dismal) performance with me, she tried not to laugh, and offered some constructive criticism. As I watched one pratfall after another, it occurred to me that a compilation video of my wipe outs would be very popular with my "fans" in Australia.
Later on that afternoon, Noelani smeared sunblock all over me again, and took me out for another surfing lesson. I didn't do much better, but at least I corrected some of the more glaring mistakes, and I was standing up and at least trying to ride waves. But there was so much to learn, how to read the waves, and figure out where they were going to break.
That night after dinner, Watkins told me, "Mr. Silvers just arrived. Just so you know, he will be expecting a blow job."
"Tonight?" I asked.
She looked down at me as if she were talking to an idiot. "EVERY night, Andrea."
"Oh
OK," I said.
"It's not much of a price to pay for a vacation in Hawaii, is it?"
"No, Ma'am," I said.
That was how the entire week went for me. Noelani would take me out to surf twice a day, and I actually did get better at it. By the end of the week I could ride small waves
more often than not, anyway. The photographers were always on hand to record my lessons, which I guessed meant that they would have plenty of material for at least two or three volumes of my more spectacular wipe outs that the Australians would love to see. At least Noelani didn't take advantage of me. Then again, she was probably having more than enough fun watching me fall off my surfboard over and over.
The rest of the time, the photographers took pictures of me. Me on the beach, standing next to my upright surfboard with my pretty hair blowing in the breeze, or me on my knees pretending to wax my surfboard. Those were probably the least embarrassing pictures they had ever taken of me on my knees. And of course I had to give Mr. Silvers a blow job every night. After a week under the tropical sun, I wasn't quite as dark as Noelani, but this was by far the best suntan I ever had. Friday night I went to sleep thinking these surfing lessons were wearing me out more than swimming laps ever did.
Then I woke up in a large bed. I recognized it; this was the canopy bed on the yacht. I was in my nightgown, and after a quick inspection, I was relieved to see that my penis chastity had finally been removed. Then Watkins walked in on me.
"Andrea, your Spring Break is over. Did you have a good time?" she asked.
"Yes, Ma'am. What day is it?"
"It's Saturday night," she said. "You can get dressed and go home."
"OK, thanks," I said.
I got dressed, and hurried to leave before they could think up anything else they might do to me. On the drive home I had a chance to think about the past week. Hawaii seemed like a nice place, although it was really hot there, and I hadn't seen anything but that one private beach. Still, I had learned to surf, at least a little, so I thought maybe with some more practice I could go surfing with my teammates.
I got home, and Caroline stared at me, her mouth open.
"What's the matter?" I asked.
"Andrea, where have you been? You look like you're at least three shades darker!" she said.
"Oh yeah, I got a suntan," I said. "I've been in Hawaii all week."
"Hawaii?? I didn't know you were going to Hawaii!"
"Yeah well, neither did I," I said. "But I did manage to take some surfing lessons. It's fun, but it's not as easy as it looks."
"Those magazine people took you there?" she asked.
"Yeah, they took lots of swimsuit pictures of me, so I might be in the magazine again," I said. That's all I told her. The less she knew about the sordid side of my life, the better. At least I was finally beginning to understand it. They offered me the carrot or the stick. If I did what they wanted, they rewarded me. If I didn't, they punished me. A week in Hawaii, or a weekend of abuse; it was up to me. The carrot or the stick.
Monday morning I showed up at the pool to swim laps, and everyone stared at me. Finally John, the team captain, asked, "Andrea, what did you do on spring break? Did you spend the whole week in a tanning salon?"
"Oh no, I went to Hawaii," I said. "I even took some surfing lessons!"
Now all of the guys got excited and crowded around me. "You're into surfing now? Did you have any good rides?"
"Eventually, a few of them," I said. "But it's really hard! There's so much to learn, it's a wonder I didn't kill myself!"
"We can teach you how to surf! We go surfing at a beach near here. There's a point break where the waves are usually cranking, and now that the weather is getting better, you can come with us," he said.
"Well maybe," I said. "I'll have to see how busy I am with school."
So we left it at that. It wasn't that I didn't want to go out to some remote beach with the guys, or that I didn't trust them. I was the best swimmer on the team, but I was sure I was also the worst surfer on the team. I didn't want to make a fool of myself out there in front of my teammates, and as clumsy as I was on a surfboard, I might actually be a menace to all of them. So I started thinking that when school was out for the summer, that might be my project. I could spend the entire summer learning to surf, and then maybe I would be good at it by the time I went back to school in the fall.
But first I had to find out if I would be free this summer. So I called Marge Watkins, the magazine editor, to see if they had any plans for me.
"So when school is done, am I free for the summer?" I asked.
"Andrea, you know we expect to see you one weekend a month. That is our agreement."
"But I thought that was just for the school year," I said.
"Your school year doesn't matter to us," she said. "In fact, once you're out of school, you could spend more time with us on the yacht this summer."
"Um, that wasn't what-" I started.
"Oh, so you don't want to change the deal after all?" she asked.
"No, Ma'am."
"You know, if you aren't happy with this arrangement, we could take you to Australia this summer. It will be much cooler in the southern hemisphere, and I'm sure your fans would be delighted to see you."
"Please, no-"
"I see," she said. "So then you'll be happy to continue with the present relationship, and we'll see you next month?"
"Yes, Ma'am." I said. "I'll be there, just tell me when."
"Good, I'm looking forward to seeing you again."
So that was that. I was lucky to get off the phone before I had talked myself into an all-expenses-paid trip to Australia. It wasn't bad enough that these people could kill me any time they wanted. They could also make my life miserable by shipping me off to Australia, or for that matter, by selling or renting me to their business associates right here in California. All things considered, one weekend a month on a luxury yacht didn't seem so bad.
That night I went to bed thinking I was a boy that looked like a girl, pretending to be a girl. I was rich enough to do anything I wanted, and yet I was a slave. Depending on the choices I made, my life could be a dream, and it could also be a nightmare.
The End
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