Chapter 10
Monday - Day 10
I woke up Monday morning conflicted. On the one hand, it was Monday, and I had to go back to work after such a lovely and interesting weekend. On the other hand, I was getting a blowjob from a beautiful woman. I decided I'd worry about work later. For now, I'd just revel in the wonderful blowjob.
I did revel, but I soon grabbed Becky and pulled her up for a kiss. "All ready for work?" I asked her.
"Almost, sir," she replied. "I was just getting my breakfast."
"Well, today you are going to have to do without breakfast," I told her.
"No breakfast for Becky?" she said with a pout.
"No, my nasty little cum slut," I replied. "You'll have to get a donut or something to tide you over. You and Jamie nearly killed me this weekend, and I need time to recharge, especially given what I have in store for you."
This was another thing that Becky and I used to disagree about. Sometimes I just wanted to play without reaching a conclusion. But Becky never let me start anything unless we had time to finish. She always said that it would leave her too frustrated.
As for me, I felt that being frustrated was not always a bad thing. I'd rather she popped me in her mouth and licked me for 10 seconds than do nothing. As long as I knew that eventually we'd finish up what we started, both the memory of the short tease and the anticipation of what was to come delighted me. This morning's session would keep me wound up all day, and tonight I had something planned that I thought we would both like.
"What do you have in store for me?" Becky asked eagerly.
"You'll find out when you get home," I told her. "I'm going to leave a new outfit on the bed for you. You can wear it in the apartment."
"Oh, Goody!" she said. "Are you sure I can't have my breakfast?"
"No, you can't!" I said, spanking her ass. "Go to work!"
"Yes, sir!" she said, and off she went.
I got ready for work and left after setting out her outfit for her.
I was sitting at work when I got the phone call from her. "Hi, Becky. What's up?"
"Sir, I have a favor to ask," she said.
"Yes?" I replied.
"Rachel and I have been talking," Becky told me, "and we'd like to go out for girl's night out. Sir, may I please have permission to go out with her tomorrow night?"
"Is she right there?" I asked.
"Yes, sir," she replied.
"And are you trying to tweak her buttons?" I asked.
"Yes, sir," she said.
"So you want me to do something outrageous?" I queried.
"I'm not sure what you mean, sir," she responded.
"Let me talk to her," I instructed.
"Yes, sir," she said. I heard her talking to Rachel and then she handed the phone to Rachel.
"Hello?" said Rachel.
"Hi," I responded. "I hear you want to go out with Becky. That's fine with me, you just need to make sure of a couple of things."
"What?" Rachel asked, sounding confused.
"You need to make sure she is home by 11PM, and you should make sure she doesn't flirt too outrageously with any men. Can you do that?" I asked her.
"Can't she do that herself?" Rachel replied.
"Yes, she can," I said, "but I find it best to make sure that someone is in charge of her when she is out of my direct control. I'll make sure to tell her that she has to listen to you tomorrow night and do what you say. Now, you have a good time!"
"Ummm, OK," Rachel said, sounding very unsure of herself.
She handed the phone back to Becky who said, "Yes, sir?"
"I've told Rachel that I will instruct you to listen to her tomorrow night. That she is to have you home by 11PM and she should not let you flirt with any men too badly. She thinks she will have to be in charge of you. Is that about what you were looking for?"
"No sir," she replied, "but it will do. I'll see you at home tonight. I love you, and thank you for taking care of me."
This should lead to an interesting discussion tonight.
When I got home in the evening, I came in expecting to see her waiting for me in her new outfit, but the apartment was empty! I was quite surprised that she hadn't called me to tell me that she was going out. I was about to call her on her cell phone when there was a knock on the door.
I opened the door and there she was. She was standing outside the door in the outfit that I had picked out, a bag in her hand. Let me describe the outfit. She was wearing a button down white shirt, a size or two too small. It was clear that she was not wearing a bra, as the shirt was not that thick and her nipples were standing out quite prominently. She was wearing what could be called a catholic schoolgirl uniform skirt, plaid and very short. She was wearing white knee socks and black patent leather shoes.
Her red hair was done up in a ponytail and she was either wearing no makeup, or just a small amount. She looked like she was 15 or 16 years old, and that is only because her breasts were so obvious. If I was really into this kink, I would have gotten her a tight white bra and she could have passed for 13 or 14.
My cock, which had been half hard all day, suddenly popped all the way up.
"Excuse me, sir," she said. "I'm sorry to disturb you, but I am selling some things to raise money for my school, and I was wondering if you were interested in buying anything from me?"
It took me a second, then I said, "Certainly little girl. Why don't you come in and you can show me everything that you have."
"OK, sir. My name is Becky," she said, skipping into my apartment. She skipped! I had her sit on the couch, while I sat across from her.
"So what are you offering today, little Becky?" I asked.
She reached over into her bag, and started taking some things out of it. While she did, I noticed that she was sitting with her legs spread a little, and I could see right up her skirt; she was wearing plain white cotton panties. The illusion was slightly spoiled by the fact that she had a very large wet spot right over the entrance to her pussy, but I could live with that.
"We have chocolate," she said, pulling out some chocolate bars and putting them on the table, "and cards and wrapping paper," she continued, pulling those out as well, "and a catalog of cookies and cakes." When she pulled out the catalog, something else fell out and she quickly and guiltily shoved it back in the bag.
"Is there something else in there for me to see?" I asked.
"Oh, no sir!" she said. "I'm not selling anything else. That's just something I have to give back to my best friend Jamie."
"What is it?" I asked.
"It's personal, sir," she said. "I would be very embarrassed to show you."
"Oh, I feel like we are becoming friends, Becky," I told her. "You can tell me what you have."
"Do you promise not to make fun of me, sir?" she asked.
"Of course I won't make fun of you!" I said. "I would never make fun of a friend."
"OK, sir," she said. My little actor was actually blushing!
Becky pulled out the last thing from the bag. It was a medium sized dildo!
"That is your friend Jamie's?" I asked, taking it from her.
"Yes, sir," she replied.
"How come you have it?" I asked.
"She let me borrow it," she said.
As I was holding the dildo, I noticed that it was wet and sticky. I held it up to my nose, and it was quite fragrant.
"This is wet," I said.
"Oh! I'm sorry, sir!" Becky said, burying her face in her hands. "I used it before and I didn't wash it off! I'm so embarrassed!"
"There is no need to be embarrassed," I told her. "Everyone masturbates sometimes. I do it all the time! It's OK. You are lucky to have a friend like Jamie who will lend you her personal items."
"But I'm not, sir!" Becky cried out. "She only gave it to me because she said I couldn't get my own boyfriend! She has a boyfriend, and she's done all sorts of things with him, and she always tells me about it! Soon she's even going to go all the way with him!
"It's not fair, because I don't have a boyfriend, and she treats me like a little girl because I haven't done anything, and she thinks she is such an expert just because Tommy Michaels felt her up and she jerked him off! I am not a baby!"
"Why don't you have a boyfriend?" I asked. "Surely someone as pretty as you has a boyfriend!"
"Do you really think I'm pretty, sir?" she asked. "No one wants to be my boyfriend. All the other girls have bigger boobies and boys think that since I've never gone out with anyone, and since my parents are so strict, they won't get anywhere with me. It's not fair!"
"So your friend Jamie keeps teasing you because she is more experienced than you?" I asked.
"Yes, sir!" she said vehemently. "And it's not because I'm more of a prude than she is! It's just that I haven't had the opportunity!"
"Well, if the boys in your school are too dim to see how attractive you are, maybe you should look elsewhere for someone who does think you're pretty," I said.
"But, sir!" Becky cried, "Where would I find someone like that? Ohhhh!" She lowered her eyes and said, "You said that you thought I was pretty, didn't you sir?"
"I certainly did, Becky," I told her. "I think you are a very pretty girl, and I think your boobies are just perfect on you! Would you like me to show you some things? I can show you things that Jamie and her little boyfriends would never think of doing!"
"Would you, sir?" Becky asked, bouncing up and down on the couch. "She would be so jealous if she thought that I had done more than she had!"
"Maybe," I said. "But if we are to do this, there are a few things you will have to agree to, OK?"
"Yes, sir. Anything!" she said.
"First," I began, "even though you want to be a woman, most people see you as a little girl. I could get into trouble helping you, so you mustn't tell anybody about me, not even Jamie. You can tell her what we do, but not exactly who you do it with."
"OK, sir," she replied. "You are so nice that I wouldn't want to do anything to get you into trouble!"
"Good," I told her. "Next, since I am the teacher, you'll have to do everything I say, OK?"
"OK, sir!" she replied.
"If you don't listen to me, I may have to punish you," I said, with a twinkle and grin.
"Ooooh, would you pull my panties down and spank my bare fanny?" she asked.
"I might have to," I responded seriously.
"I understand, sir," she said, just as seriously. "If I am naughty, you should spank me."
"OK, then," I said. "Tell me what you've done so far."
"That's just it, sir!" she said with exasperation. "I haven't done anything. I once kissed a girlfriend to practice, and I've played with my thing with my hands and just today I used that thing I borrowed from Jamie on my thing. But that is all!"
"Well clearly," I started, "the first task that you have to do is learn some words. Not everything is a 'thing.' The item in your bag is a dildo. The place you use it on is your pussy or your cunt. And you don't have boobies; you have tits. And if you get lucky, a boy might put his cock or dick into your cunt. Do you remember all those words?"
"Yes, sir," she said, and damn if she wasn't blushing! My Becky, of 'Fuck me hard up the ass, sir!' fame, was blushing while I pretended to teach her these words.
"OK then, my little Becky, tell me again what you've done so far," I instructed her.
She looked me in the eye and said, "I once kissed a girlfriend to practice, and I've played with my pussy with my hands and just today I used that dildo I borrowed from that bitch Jamie on my cunt. And I want to do more!"
"OK then, lets start with the basics," I told her. "Come sit on my lap and we'll practice kissing." She hopped off the couch and dropped into my lap, wrapping her arms around my neck. She brought her face to mine and kissed me. It was actually a pretty crappy kiss!
"First, you need to relax your lips more," I told her. "Also, keep your mouth slightly open, so that I can slip my tongue in. Are you ready to try again?"
"Yes, sir, I'll do better!" she said. And she did. The second kiss was much better. After I slipped her my tongue, she drilled right back. We probably kissed for about 10 minutes, and I swear I had flashbacks to my first girlfriend, kissing me in the back of a movie theatre.
"That's a lot better Becky," I told her, "but you know that if a boy has you in his lap, he is going to want to run his hands all over your body. Are you ready for me to show you how boys do that?"
"Oh, yes sir," she said. "But what if I get ticklish?"
"We'll deal with that if that happens," I said to her, smiling. Then I moved in to kiss her again. I started by running my hands up and down her back. Then I ran my hand around her side, causing her to shiver, and then lightly cupped her tit. I ran my hand all around it, and over to the other one. Late nights in cars flashed in my mind. Becky moaned into my mouth as my hand caressed her breasts.
She gasped and pulled back when I unbuttoned the top button of her shirt. "Sir!" she exclaimed.
"Do you really think that any red-blooded boy, having felt your sexy tits over your shirt, will be satisfied? They will want to feel them first hand!"
"Do you really think my tits are sexy?" little Becky asked in a small voice.
"I think they are sexy, and arousing and perfect!" I said.
Becky plastered her lips to mine and had no complaints as I unbuttoned her shirt all the way. She sighed deeply when I slipped my hand in and tweaked her nipple. "Oh, sir!" she moaned as I slipped my head down and licked at her swollen nipple.
"No bra?" I asked.
"My boobies, I mean tits, are too small," she said. "My mom won't buy me one yet."
"Well, I personally love it when the girl I'm kissing isn't wearing a bra," I said.
"Then I won't ever wear one when I come over!" Becky said.
I went back to kissing her, and I moved my hand down to rub her leg. I started to move my hand up under her skirt when she slammed her legs together. I started to pull away to talk to her, but she grabbed the back of my head and pulled me back as she let her legs slip open.
I rubbed around her thighs for a while, getting closer and closer to her panties. When I reached her panties, they were sopping wet. I pushed my hand up against her crotch and she shuddered, cumming on my hand.
"Oh, sir!" she said. "That was better than when I play with myself!"
"We're just getting started," I told her. I lifted her up and carried her to the couch. I laid her down and knelt next to the couch. I pulled her shirt open, and leaned back to look at her. Her hair was still in the ponytail, her shirt was open to expose her chest, which was heaving as she struggled to breathe. Her skirt was hiked up exposing her panties, which were soaked all through the crotch. She looked utterly sexy.
I leaned over and kissed her mouth. Then I kissed down her neck till I reached her breasts. I kissed and bit each nipple, bringing gasps from Becky. I moved down and reached under her skirt to pull her panties down.
"No, sir!" Becky cried, holding my hands in place.
"Why can't I take off your panties?" I asked.
"I'm too embarrassed! You'll think I'm a baby!" she cried.
"Why would I think you are a baby? I asked.
"Because I don't have any hair there!" Becky said in an anguished voice. "Most of the other girls have hair on their things, I mean their pussies. But I haven't gotten mine yet. I look like a little baby!"
I kissed her on the lips and said, "You silly girl! Do you know that half the men my age want their women to shave off their pussy hair? They want them to have pussies that look just like yours!"
"Really?" she said.
"I would never let my girlfriend grow hair on her pussy," I told her.
"OK, sir," she said with a shy smile, releasing my hands.
I pulled her panties down, and she put her legs down, close together. "Open up for me," I said.
I went back to kissing her as she opened her legs up and allowed my hand in. I ran my hand all over her body, from her neck, to her tits, to her waist, to her pussy. I moved my fingers into her wet crack and I said, "This is where you put the dildo? Did you push it all the way in?"
"Yes, sir," she said. "Even though I'm really a virgin, I don't have my hymen anymore. I think I broke it in gym one time."
"That just makes it better for you when you do fuck for the very first time," I said.
"Are you going to fuck me, sir?" she asked.
"Do you want me to?" I countered.
"I'm not sure," she said. "I'm afraid, but your fingers are making me so fluttery. I feel like I'm going to explode again!"
"Do you mean that you think you are going to cum?" I asked.
"Yes, sir! I feel like I am going to cum soon!" she replied.
"Well that is a very good thing," I said. "Lets see if I can't help you." I dipped another finger into her cunt and let my thumb rub her clit.
In just a few seconds Becky was yelling, "Oh, sir! You're going to make me cum, you are!" And she did.
After she calmed down, I kissed Becky again and asked, "What did Jamie do with her boyfriends?"
"They felt her up, and she played with their things till they spurted," she said. "But it was in the dark, and I don't think she ever got to see it good."
"So they don't get her off?" I asked.
"I don't think so, sir," she replied. "If they made her feel like you already made me feel, she would be bragging about it all the time!"
"Then would you like to see a cock in the light?" I asked.
"Oh yes!" she squealed.
I stood up and took off my shirt, my shoes and socks, and then my pants. I stood there in just my jockeys and asked, "Would you like to take these off?"
"OK," she said. She sat up and reached for my briefs. Her face was level with my cock, and when she pulled my underwear down, my cock bounced out and hit her in the face.
"It's so big!" she whispered. Then she said, "Hey! You don't have any hair down there either!"
I had forgotten that, and I said, "I told you that I didn't let my girlfriend grow her hair, so I let her shave off mine to be fair."
"It's so big," she repeated. "How can that go into a girl?"
"Well, it usually doesn't go into girls," I told her. "It goes into women. Do you think that you are a woman?"
"I want to be, sir!" she said quietly. "But I'm a little scared!"
"Don't worry my little Becky," I reassured her. "We won't do anything that makes you uncomfortable. Do you want to play with it a little bit?" I asked, sitting down next to her.
"Can I, sir?" she asked.
"You can look, you can touch, you can feel, you can smell, you can taste," I told her. "Anything you like. You can play as hard as you like with my cock, just be careful of my balls below it".
She then spent the next ten minutes exploring my cock as if she'd never seen one before. As she played I slipped off her shirt so that all she had on was the sexy schoolgirl skirt.
"How does Jamie get the boys off?" she asked.
"She moves her hand up and down, like this," I said, and demonstrated. She replaced my hand with hers and gave me an admirable handjob.
"Are you going to spurt soon?" she asked.
"It's called cumming," I replied. "And no, I won't. Schoolboys can cum if a girl gets near them, but it often takes more to make a man cum."
"What can I do to make you cum?" she asked.
"Well, what you are doing now is called a handjob," I explained. "Something that feels even better is a blowjob."
"I've heard of that!" she said. "You want me to put it in my mouth?"
"All the women that I have dated have done that," I said. "But I bet a little girl like Jamie never has."
"You're right," Becky giggled. "Jamie never did it, but I will!" And she leaned over and put my cock in her mouth. And the little bitch bit me! It's one thing to fake bad kissing, but faking a bad blowjob can be dangerous.
"Ouch!" I said. "The only time you ever use your teeth in a blowjob is to gently run them up and down a cock, and then only after you've had a lot of practice. Be careful, and use your tongue and lips a lot!" She suddenly got a lot better at it.
"Wow, you do that better than most of the full-grown women I know," I told Becky.
She took her mouth off my cock and smiled proudly at me. "Thank you, sir! I'm trying. That will show Jamie!" and she started blowing me again.
"All the guys are going to want you to do this, but should I tell you a secret?" I asked her.
"Oh, yes, tell me more," she said eagerly.
"Most of the boys will want you to make them feel good," I explained, "but won't do anything to make you feel good. So what you should do is have them make you feel good first. You shouldn't blow them until they eat you!"
"Eat me?" she squeaked.
"Yes, I'll show you," I told her, and I laid her down and started licking her bald little pussy.
"Oh! This is even better than your fingers! Even better than a dildo! This is great!" Becky continued a stream of encouragement right through when I made her cum again.
"Oh, that was so good, sir!" she told me. "I bet Jamie has never done any of this! She thinks she's so grown up, but all she's ever done is jerk off a couple of guys. She never had someone eat her!"
"You know what would really show Jamie?" I asked.
"What, sir?" she responded.
"If she were still a little girl virgin, but you were a woman who has fucked a man!"
"Oooooo! That would steam her so much!" Becky said. "Lets do that. Please do it to me now!"
"Do what to you now?" I asked.
She smiled widely at me and said, "Please fuck my little girl pussy and make it into a woman's cunt. Please fuck me and play with my titties. Please make me a woman!"
"I think it would be better if you made yourself a woman," I said. "Don't go back to Jamie and say 'I let a man fuck me.' Go back and say, 'I fucked a man!' Climb on me and fuck me yourself.
"Yes, sir!" she said, and she climbed on my lap.
"Wait a minute!" I cried. "I don't have a condom. You should always fuck with a condom so you don't get pregnant! We shouldn't do this."
"But sir, I just finished my period a few days ago!" she said. "I learned in health class that this time is pretty safe."
"But I could still make you pregnant," I said.
"I don't care, sir! I'll take the chance. If you make me pregnant I'll never tell who it was. Please just let me fuck you!" And with that, she slipped her very wet pussy over my cock.
'Very tight, ' I thought to myself, 'but not quite as tight as a 15 year old virgin.'
"Oh, it is so big!" Becky moaned. "Please let me wait to get used to it." But Becky herself couldn't wait long, and very shortly she was bouncing up and down on me while I cupped her ass with my hands.
Becky wrapped her arms around my neck and her head was resting on my shoulder. As she bounced up and down she said, "I'm fucking my first man! Jamie will be so jealous. I can be just as slutty as her. I'm not the little girl, she is! I'm a woman. She'll believe me when she sees my stomach getting bigger. You're going to spurt in me. You're going to make a baby in me. Make a baby in my 15-year-old tummy. Knock me up! Put a baby in me. Do it! Do it! Cum in my while I cum!"
With that, Becky came hard, and took me with her. I came in her, amazed at the fantasy that she was acting out. After she relaxed for a few moments she pulled off of me and looked at my cock. It was covered in our cum. She reached over and ran her fingers up my cock, scooping up as much liquid as she could. She then reached over and shoved her fingers up her cunt.
I looked at her in surprise and she said, "Since you already put your cum in me, I thought I should get all of it. And don't worry. I promise that if I do get pregnant I'll never rat you out. But next time I'll bring condoms."
"So you'll be over again?" I asked.
"Of course! I'm sure there is sooo much more that you could teach me," she said while playing with my spent cock. "It's so funny how he can be so big and hard one minute and so small and soft the next. And he's so messy!"
"Well if you want to be a really good slut," I told her, "you would make sure that you clean any messes you make with your mouth!"
"Oh, sir, I'm sure you will teach me to be the best little slut, and not a little girl at all!" Becky said, and dropped down and cleaned my cock off with her mouth.
When she was done, she kissed me, and then started getting dressed. She put all her stuff into her bag, and then held up the dildo and said, "I have to drop this off at Jamie's and then go home and do my homework. Oooo, I have a wicked idea!" She pulled her panties to the side and inserted the dildo into her dripping cunt. "Maybe she'll use it tonight, and some of your cum will go in her and knock her up! That will show the bitch!"
She finished putting everything away, kissed me again and said, "Thank you for teaching me so much!" With that she skipped off into the bedroom, closing the door behind her.
About a minute later the door to the bedroom burst open and Becky ran out and literally jumped into my lap. She grabbed me and kissed me all over my face.
"How do you always know what will turn me on so much? That was great! Everything you did. Oh! I never knew how much that would turn me on. Thank you!"
"No! Thank YOU!" I said. "You were pretty fabulous yourself. You play a 15 year old girl perfectly!"
"And you play a dirty old man pretty well yourself!" she replied.
"Old?" I said, indignantly.
"Only from the perspective of a 15 year old girl," she reassured. "Was that costume for you, or did you know it would turn me on so much?"
"Well, since you've become more sexually open with me, you've let some things slip," I told her, "and some of the things that you've said made me suspect that this would get your motor running."
"Did it ever! I love the outfit!" she said.
"Well that's good," I told her, "because part of it is another house outfit. You may wear the skirt and the shirt, though the shirt must be unbuttoned and tied together underneath your pretty tits. No panties; they are only for when we are playing. And I like your bare legs. Also, when you are wearing it, I want your hair up in two ponytails, one on each side of your head."
"Do you really think my titties are pretty?" she asked, holding them up to me.
"Yes!" I said, kissing each of her nipples, "Now go take your sexy body, little girl, and get it cleaned up for dinner! I'll go make something for us to eat."
"Yes, sir!" she said as she scampered off to the bedroom.
At dinner I asked Becky about her day. In addition to the conversation that she had with Rachel, both Jamie and Christine had called her.
"Jamie wanted to talk more about our relationship," Becky told me. "She seems to be giving our proposal serious consideration. I guess I thought that she would just go along with it, but she appears to be taking your advice and thinking about all aspects.
"She asked me about all the things that you made me do, and which things I did myself. I actually got quite wet rethinking all those things. Have I told you how much fun I am having?"
"You might have said something once or twice," I told her, "but I always like hearing it."
"Well," Becky continued, "it is clear to me that Jamie has not made up her mind yet. She definitely is thinking it through all sides.
"Christine is another puzzle to me. She called and we just chatted. At first I thought that she had decided not to be my slave, and to just be friends, but when I asked her about it she very neatly sidestepped my questions. I am not sure what she was doing, and it is frustrating me.
"Sir, now I'm worried that we won't have Jamie or Christine!"
I pushed my chair back, opened my arms, and indicated she should come to me. She came over and sat in my lap. I held her and kissed her face. "My little Becky, would it be so bad if it was just the two of us? We'd still be able to have fun with Jamie, even if she wasn't your sister slave. And knowing you, you'd come up with other schemes to tweak both our buttons. I've told you before, I would be perfectly happy to spend the rest of my life only being with you."
Becky smiled at me and kissed me. I held her for a while longer, and then we hung around until bedtime, though Becky remained somewhat subdued. At bedtime, Becky came up to me, knelt before me and asked, "Sir, would you collar and cuff me and then make love to me?"
"Of course, my little tiger," I said. I collared her, put on her cuffs, unclipped, and took her to bed. I made love to her slowly and for a long time, and eventually we both came. We snuggled together (after she insisted on cleaning me off, of course) and drifted off to sleep.