Yep, I'm the macho guy who picked up this great babe in a hotel bar, took her back to her room, boffed her butt good, then discovered the next morning a transformation, a change in gender from knock out babe to dude. That day there was a tell all discussion about what she was and wanted to be, with a bunch of intimacy thrown in to keep my interest. We had just finsihed a really good fuck, showered and were recouping on the bed.
We gulped the wine quenching our thirst, then sipped lanquidly laying together. Sherry looked at me and asked, "What now?"
The male in me recovering from my orgasm stupor responded dumbly, "You'll have to wait till I recover a bit."
"That's not what I meant." Sherry said, "So now that you and I have to go home, away from each other, what now?"
"Somehow" I said, "somehow, we have to stay in touch, get together, or something. You are too facinating for me to just forget." I squirmed a bit trying to stall think of an answer. "Sherry, for starters, let's compare our travel schedules and locations so we can see if they conincide very much."
Sherry pulled herself up to sit, leaning back against the pillowed heardboard next to me. "You know I don't travel much, just to a few corporate headquarters to work with buyers and their store managers when needed. I work mostly from home and go into our main plant once a week or so. Almost all my contact work is done from my home office."
I turned to look at the gorgeous creature next to me. At that second convinced it was a she and wondering how I got so lucky. She was definitely messing with my mind.
"My travel comes from new customers. When we implement their new software there is usually some compatibilty problems integrating the old with the new. So I do a discovery mission, then make sure the modifications work, then split before the trainers come. Most of my work is done from my home office too, either on the phone discussing issues, minor programming, and reports. My boss says he wouldn't recognize me if we were on an elevator with each other." I paused, took a sip of wine then said, "It really doesn't matter where I am as long as I have my cell phone, can poll my email and send and receive a little data."
Sherry turned toward me now sitting with a legs crossed indian style looking at me. She took my hand and said, "Steve, could you come to Dallas to visit? Could you come for a day or two?"
"I guess so." I answered. "For anything special?"
"Yes you jerk, for me, to see me." Sherry said giving me gentle punch on the are muscle.
"Oh, OK, that would be nice."
Then she gave the head down looking up look. "I want you to meet my sister. She is my only family and I want her to meet someone who accepts me for the person I am. It's really important to me, Steve. My sister Mary will be extremely pleased to meet you and may be even a little jealous."
"Jealous?"
"You know you're good looking. And, the more I know of you, a good catch too."
"Well, we'll see." I said. "Want me to go to Dallas from here?"
"Why not? We could fly together."
"Sounds like a plan. I'm not ready to let you get to far away yet. You are still a big mystery to me and there's no way better than to stick as close to you as possible."
We settled down after that gently kissing then drifting off to sleep.
Light was starting to show through the room curtains when my eyes opened. That didn't wake me up though. What woke me was the insistant pulling of my dick by something that was warm, wet and making mmpfffing sounds.
All I could see was a beautiful head of auburn hair bobbing in my lap. About the same time my view and all the sensations started to make since, my body spasmed and I launched a large load into the sucking mouth.
The mouth kept right on sucking, a little gentler, but still sucking, coaxing the last of my essense from me. Then pulling back her head, my dick made a popping sound, then she turned to me. Sherry's face had a tight lipped grin on it. I reached to pull her up to me and she came willingly. When her lips met mine she gave me an open mouth kiss that released everything she had taken from me into my mouth. She kept kissing, sucking my cream back out of my mouth, smearing it with wet kisses all over our face. Sherry pushed herself up with her hands on my chest showing those beautiful breasts and grinned some more. She had a twinkle in her eye when she said, "Better'n Listerin, don't you thinK?"
With that she rolled out of bed and said on the way to the bathroom, "I gotta' get going. Have a short meeting at 9:00 then should have everything wrapped my noon. Whatta you have today?"
I swung my legs off the bed, sitting and scratching like most male mamals do first thing in the morning. "Well after that wake up, I need a nap. But, If all the changes were sent and work, I could be outta here."
We showered together with me marveling at the top half being 1000% babe but the middle part showing the unmistakable guy stuff. "Oh my" I thought, "What have I gotten myself into."
I slipped on my pants and shirt then scooted across the hall to shave and dress. I called into the home office lab and was told it appeared all the changes were working at that time. I was just opening the door when there was soft knock. Opening the door I was greeted with that guy again. Gorgeous eyes, hair pulled back tight in a pony tail, dressed in fashionable suit with what I now knew had some heavy shoulder pads.
"Oh." My surprise look and wide open mouth giving my surpise and astonishment away.
Sherry/Terry said, "Just wanted to find out if I should call you or what before I left?"
"Yeah, that'd be good." I said, still confused over the vision presented to me. I had to just stare, trying to figure out what she did with those knock out tits when she had on a suit. Try as I did, I still couldn't tell "IT" apart from some high fashion dressed guy.
Sherry/Terry grinned and said, "You'll get used to it. Hang in there until I can be all Sherry later and then forever."
"Okay, let's get going so we can get going." I said this with a true enthusiasm knowing I was going to see that facinating Sherry soon.
By eleven o'clock we had both finished and met up at the hotel. I was able to change flights around and make reservations to Dallas with Sherry. Because of making the late changes, I knew we probably would not sit together. When we left for the airport I was surprised to see Sherry as Sherry and not Terry. She just said she needed to travel this way with me. At the airport, Sherry asked for my ticket and went to the counter. Before she left Sherry told me to go into the bar and get us a table so we could have some lunch and a smoke before we left.
Sherry came in beaming. She said, "Had no problem getting us seated together. Now I don't have to let you out of my sight for a second."
We ate, smoked, then heard our flight announced. When they called for the steerage to board I started forward, but Sherry held me back. She just said, "Let's wait until everyones on, then we'll go, less struggle don't you think." Who am I to argue with this beautiful babe on my arm.
We went through the passage way and boarded the airplane. A hostess looked at our tickets and said to follow her. We went to the last seats in first class and she stood with her hand indicating for us to sit there. I started to say something when Sherry gave my arm a little shove and said, "Sit."
I shut my mouth and sat. Pretty cool, don't sit up in first class often. I turned to Sherry and asked, "What's up?" She just turned to me smiled and said, "I wanted to travel as Sherry and this was the safest way to do it. Kind of insurance of not being too obvious. Besides I only used a few of my extra frequent flyer miles for the upgrade."
We put the chair arms up between us so we could sit closer. In reality we could have been comfortable in coach the same way as we were so close. Sherry then said, "This will give us a chance to talk more. There's so much I want to tell you about and so little time. I just want to see if we can convince each other we're right for each other."
"Don't worry Sherry," I said. "I'm not running. I want to see what you're all about before I run. So tell me about your home. Tell me about your work. Tell me about your sister. You know, tell me more about yourself."
Sherry surprised me again when she said, "My sister looks exactly like me."
I asked, "Exactly like you?"
"Well, all except for the boy/girl part. We're twins."
"Twins?"
"Yeah, twins. Mary is ten minutes older than I am, so she claims she's my big sister. Wait till you meet her, she is gorgeous and much better built than I am."
"Now that's hard to believe." I said.
Our conversation continued throughout the two hour flight so when we landed we had told each other a ton of ourselves. We retrieved our luggage then took a shuttle to the long term parking to Sherry's car. Sherry's company car was a cream colored Linclon. Not bad, considering I drove a beat up Chevy. She was going to have me drive but then said, "You know, I better drive cause the traffic here is really strange and fast. Once we get home you can drive when you need."
We pulled up to the garage of a very nice home in a nice tree lined subdivision. The houses had big lots and lot's of privacy. When the houses were built, they were probably for the very high middle class. Now they were the home people fantasize about while they decorate their starter homes.
Sherry jumped out and said, "Come on, leave the bags and come inside, quick." Sherry nearly drug me to and through the door.
As soon as the door closed quietly, a voice rang out, "Terry, that you?" Sherry pulled me toward the voice which was down a hall toward an open door. I was pushed into what apparantly was an excercise room and there was a girl reclining on an excercise machine pulling weights toward her tummy. The greatest part of this whole view was the girl looked exactly like Sherry with her hair in a pony tail. She looked exactly like Sherry except her chest. This was obviously bigger than Sherry's and not enhanced as her breast sagged to each side from the sheer weight of them. There was another difference as she had her feet spread toward the door, you tell she was girl. How could I see all this you ask? Easy, she was naked.
I gasped.
Sherry said, "Opps!"
The girl said "Oh shit," and tried to sit up and cover herself with her hands at the same time.
I turned to leave and Sherry pulled me back out of the room, then pocked her head back around the door and said. "Damn, Mary put some clothes on, I've someone for you to meet."
The voice said, "Go into the living room and I'll be right there. But jeez, give a girl some warning next time."
We went back to the living room where Sherry commented, "As you can see we're not real modest around the house. Sorry if that overly surprised you."
I just smiled and said, "Well, that's one good way to see the family resemblence."
Sherry hollered, "Come on Mary, hurry it up."
The voice responded, "I'm coming, I'm coming." And at that moment the voice rounded the corner presenting me with another big eyed beauty in a robe, bursting at the top, lots of cleavage due to being tightly belted beneath her breasts. "How come your dressed up? You never travel that way."
"Mary," Sherry said, "Please meet my new friend Steve. Steve, Mary my sister."
Mary said, "Sister and Twin."
"Sherry?" Mary asked, "Uh does your friend know you very well?"
"Yes he does." Sherry answered. "He knows about a lot of me and has accepted me as I am. He's here to meet you and to get to know more about me. And, if he gets to know more about me, he'll have to know more about you."
"Glad to meet you Steve," Mary said sticking her hand out as an offering. She did this with a smile but you could still see the wariness in her look.
"Happy to meet you Mary. Sorry about the intrusion a moment ago."
"That's Okay, just my boneheaded brother forgets others may not be used to our casual dress around the house."
"Don't mind me," I smiled. "Your casualness was very interesting."
Sherry elbowed me in the ribs and said "Sit."
On the way down I just grumbled that she was treating me like a dog.
Mary chuckled and sat directly across from me. When she sat, the bottom of the robe spread showing a lots of thigh and the top blossomed showing even more cleavage.
Sherry said, "You're about to fall out." Gesturing toward Mary's chest.
Mary said, "Well he's seen 'em already anyway so sit down and tell me about this Terry."
"Don't call me Terry Okay, Steve likes me as Sherry and I like to be Sherry so try for me Huh?"
"Okay, whatever, it's just hard to remember sometimes."
Sherry spent the next half hour giving her/his sister a detailed account of the past couple of days. How we met, nearly a play by play of our fun times, the chance meeting, and then our talks and subsequent fun times. Right up to the point of her driving instead of me.
Then Shrry said, "Well, whadaya think?" "He followed me home, can I keep him?"
Mary continued to have a quizical look on her face. She turned to me staring, seeming to peer into my mind. "Are you gay?"
So much for the gentle approach.
"No!" I said. "I have never been with a guy."
She interjected, "Until Terry that is."
Sherry blurted, "Call me Sherry, Okay?"
"Yeah, you're right, not until Sherry." I said, humbled by my admission that I had had sex with a guy.
Sherry saw my long face and said, "Honey, it won't be long. I'll be a real lady."
Mary laughed, "You're already more of a "lady" than most of the women I know." "But you are just packing a little extra down there."
Sherry again flashed her eyes at Mary with a displeasing glare. "You don't have to remind everyone."
Mary leaned forward, spreading her legs then leaning her elbows on her kneew clasping her hands. This did two things. Her robe blossomed, baring all of her huge hanging breasts. With her legs spread, something else blossomed and was staring at me. I had to take a deep breath, my face turning red. Sherry gasped and started to say something but Mary held up her hand.
"Terry,, ahh,, Sherry, how much have you told him. Just about you? About me? About us?"
"Huh, I thought." Clang, Clang, alarm bells started going off. Wonder what Mary was alluding too.
Sherry quickly said, "He barely knows anything of me. We really haven't had much time together yet."
"That's what bothers me." Mary said looking hard at me. "Love at first sight? Or looking for a scam? What is it?"
I could barely talk but finally almost whispered, "Best I can say is, initially I was totally captivated. Now? Still captivated, but intriqued of who Sherry really is. I still can't hardly except Sherry is male. Guess that makes my gender a little mixed up too, but I have to find out where this relationship is going."
Sherry said smiling, "Honey, your gender is secure, you are all male." With that she squeezed my arm and gave me a buss on the cheek.
Mary still hunched over displaying everything said, "Terry,, ah,, Sherry, this IS the first guy you've ever brought to meet me, so it must me something." Then she looked hard at me again and said, "Steve? There is a lot more to know of Terry-Sherry and a lot more to know about us. We'll see how it all goes."
She turned to Sherry and said, "Meanwhile, baby brother, if you think I'm gonna walk around in my own home dressed to the nines, you gotta another thing coming. I'm usually naked and don't intend to start now. But I will respect your guy and try to stay a little covered for a bit."
With that she got up walking out of the room and hollered back, "Have to finish my workout before I'm out of the mood, talk to you guys later."
Sherry pulled my face to hers for a sweet kiss. She pulled back, "There is lots I have to tell you, but first, let's get our stuff and put it away."
We got our bags and put them in her room. Remarkably her room was a girls room. Frilly. Pinks, yellows, light blues. Lacy bed spread. Canopied queen size bed. Very feminime. Even a make up table - chest with a big mirror and surrounding lights. I changed to some shorts and a T-shirt then sat in a huge stuffed chair in the corner. I watched Sherry put away stuff, separate her dirtly clothes mostly female underwear, hang up her clothes then change to some short shorts and T-shirt losing her Bra along the way. She kept her thong pantied butt toward me while changing into her shorts but gave me a great look at her beautiful chest while putting on her T-shirt. Ah, the tease. I love to be teased.
When she was done, she said "lets get a snack" and started out the door. I followed her to the kitchen. Nice kitchen. Huge, with an island counter, high chairs on one side, a nice table and chairs by a window overlooking a patio and pool. Sherry said "sit at the counter and I'll make us some sandwiches. Want a coke? a beer? coffee?"
"A cup of coffee would be great, what can I do?"
"Nothing," Sherry said, "I know how to take care of my man."
I was just sitting in a counter chair when Mary came with a very short robe flapping open as she walked. "Yep he,, ab,, Sherry knows how to take care of me too." She said with a smirk.
"Mary!" Sherry snapped, "Cool it, will ya? I'll tell Steve everything there is to tell him shortly. Meanwhile just be nice. Okay?"
More alarm bells.
"Just don't want you to lead this guy on. Can I have a snack too. And, can I stay and help with the discussion with Steve? I promise to be nice and to be honest." Mary said all this without taking a breath. It was obviously important to her.
Sherry must have heard her need as Sherry said, "Yes, Mary, you should be here too. If Steve is interested in me, he'll have to interested in you as well."
Gong, Gong, Gong
We ate at the table, drank some coffee, all three of us smoked some, then Sherry pushed her chair back, folded her arms across her bontiful chest then said. "You know, when I got my tits done, I asked the doctor to make mine just like Mary's. He said he couldn't make 'em that big all at once. I was really dissapointed. Mary said there had to be some difference between us. Guess I have always wanted to be just like Mary, look just like Mary."
Mary started to say something but Sherry held her hand up. "Let me. I need to tell Steve as much as I can."
"You see," Sherry began, "Mary and I were orphaned when we were 16, near 17. Our parents were killed in an automobile accident. We were both in high school. Both of us were pretty much loners as we spent more time studying and being part of a great family than with other kids. We always had each other to pal around so we didn't socialize that much. I was confused with my gender since about 12 or 13 and would sometimes sneak Mary's clothes to dress in. But mostly I wanted to be exactly like Mary. When Mary started to date, occassionally, I wanted to date guys too. Like I said, confused. Mary wanted me to date some girls but I was too shy. She kept after me but I kept her off by saying I was too shy and wouldn't know what to do. Well, Mary said she would teach me how to get along with girls."
With that Mary started to speak, "Umm Sherry?"
Sherry just said. "I'm gonna tell it all. If Steve and I are gonna work, it's has to be. Wanna leave while I tell him?"
"No way." Mary said. "Have to stay here just to be sure you tell it right."
Sherry continued, "Well, at around 14 Mary said she was going to teach me. So one night when our folks were out, we sat on the sofa where I had my first "girl" kiss. At first we kissed on the lips then did some tongue kisses. We really got into it. It made me hot and horny. Both of us couldn't believe we were reacting like that. We quit that night and both of probably wore our hands out satisfying our itch. Then a week or so later we tried it again. Same result. Both of us hot as heck. We started talking and comparing experience. Both of us had none in reality. Mary had been groped at the movies while the only groping I experienced had been with guys. Since we had always been openly nude with each other and had discussed how we would have to masturbate after we kissed we decided to kiss some more then try to handle each other too. We were successful at that, instantly. The more we did, the more we liked it. Just before our parents were killed, we went the final step. One night, while alone, we played and played. Mary said she wanted to find out what it felt like to be, ah, to be."
"Fucked, I wanted to be fucked." Mary said.
"Okay," said Sherry, "She wanted to be fucked. She wanted me to do it and not one of her goon boy friends. She said it would mean more if I did it and I would watch out for her more. Well, we did it. We liked it and did it again. We did it over and over again. We were doing it when our parents were killed." Sherry said the last of that choked up some with tears in her eyes.
Mary jumped in, "That's not the reason they died. It was an accident."
"I know." Said Sherry, "But I still think about it."
"Well just forget it Terry,, ah,, Sherry, let it go baby. One had nothing to do with the other."
"Okay, Okay. Let me finish." Sherry said. "I went off the deep end. I didn't want to do that anymore with Mary. I wanted sex, I wanted a relationship, but with whom. I didn't want to be a boy. I wanted a boy friend. So I started trying out the guys that would come on to me. I started dressing up. I copied Mary's clothes. I did that right through college. I became better and better at disquising myself. You couldn't tell till you got my panties off. Then one day after being used and abused I got scared. My life style was pretty raw. I was worried I might have caught something. I went to the county health clinic and was tested. My test was fine but they scared the shit out of me by telling me to come back in six months to be tested again to be sure. Let me tell you, I became a recluse, celibate, not even Mary could tempt me. The only thing I did was work. I was lucky. A cosmetic company hired me as a salesrep. It gave me lots to do. When I was tested again and found to be clean, I was estatic. I thought that it was a fresh start. I started planning on how to become a real girl."
"That's about when we became friends again." Said Mary. "We lived in the same house, saw each other most every day, but we were distant. Not hardly talking to each. It was the worse time of my life. My best friend was gone and I thought it was because of me."
"It wasn't because of you, Mary." Sherry said. "I knew that. I just thought it was because of what we had done. I was ashamed." "Then," she continued. "I was ashamed of what I had become and wanted to be more. More like you, Mary. That's why I came to you to beg you to forgive me for being so crazed and distant."
"Yeah, that was an emotional time." Choked Mary.
"Steve, Mary and I became friends again. She finally recognized that I was determined to become a girl. She started to help me. She taught me how to dress properly, how to walk in heels, about foundations, about make up. And she taught me how to love again."
With that Sherry was looking down, hanging her head.
I said, "Sherry?"
"We started fooling around again. It still confuses me some. I love Mary, more than just my sister, but still."
"Get over it baby." Mary said. "You needed some intimacy, I needed some intimacy, who better than your best friend and brother. We're good together. We know what each other enjoys"
"Yeah but." Sherry started.
"Steve gets your butt." Mary grinned. "I get your dick." Then with flip of her head she looked at me and said, "As long as you have one. Guess I'll have to rustle up a substitue pretty soon, huh?"
Sherry's head came up, "No, Mary. When I'm a real girl you will still be my best friend. You and I will still be as close. Guess it will be lots of tongue, huh? But I have an idea."
"What's that baby brother." Mary asked.
"Steve?" Sherry turned to me. "Would you be Mary's too? When I'm a real girl, and even before then, even now, would you consider being Mary's lover too? Or at least till Mary finds someone special?"
"Ummm,,, Ahhh'" I stuttered.
"Sherry! You can't just blurt something out like that." Mary gasped. "You don't know if I even like this guy, which I do, but still, you need to approach this a little more delicately. You know, like look at him and just say, wanna fuck both of us?"
With that Sherry sputtered and Mary started laughing slapping the table.
Sherry turned to me, leaned over too me, gave me a gentle kiss on the lips and said, "Will you consider loving both of us? Like I said before, if you want me, you get us both."
I'm no fool. These were two of the foxiest babes I've ever seen. I'm not a knockout hunk of handsome guy. Not bad, but no movie star qualities, nothing that would warrant two choice pieces such as this.
Mary was still chuckling, "What'll it be big boy? Wanna set o' babes or at least one babe and one babe to be."
My nervous grin must have been splitting my face. "Guess I'd like to try. Kinda fast isn't it? I meet you a few hours ago and already I'm committing to you two girls at once? Geez, this is something."
Sherry stood up and pulled my hand getting to stand also. "Let's get the last of the sun and swim, then we'll talk about supper."
With that she pulled off her T-shirt then reached to pull mine off too. She was quick. She undid the button on my shorts and pulled them down. I was red faced and glanced at the open robed Mary now standing. Since I was free ballin casual, I was stark naked except for my shoes. I sat and pulled off my shoes. Sherry dropped her shorts where she stood then took my hand and started pulling me toward the sliding kitchen doorway to the patio. Sherry still had her thong, covering her gender give-a-way. I looked back at Mary and she was coming after us while her robe was in a pile beside her chair. Wow, what a view. Two of em. Twin beauties, except one had panties on.
The day's last of the summer sun was still hot. At an angle we wouldn't burn but it was still at least 90 plus in the Texas evening. We all jumped in and splashed around. I tried to swim some laps but was waylayed by one of the girls on each pass. When I stopped they were sitting side by side on the edge of the pool. They were identical. Sherry had panties. Mary's slightly larger breasts had some sag, but they were identical, bookends. And perhaps, all mine.
I watched the two talking for a few minutes then spoke up. "All right girls, it's late, we probably need to clean up, eat supper, as this has been a long and emotional day. What do you think?"
Looking at the two, my hormone indicator was trying to register interest. So I climbed out of the pool quickly then hustled inside to grab my clothes. A hand startlingly slapped my butt cheek.
"No need for decorum now dude." Exclaimed Mary. "Looks like you're starting to show some interest in your surroundings huh? See something you like?"
"Mary!" Sherry said emphatically, "Steve may not be an exhibitionist or nudist like you. He may be embarrassed to be nude."
"No reason for that boy to be embarrassed. Looks like he's got what it takes to show off like a good man should."
"Oh Mary, I don't know whether you are a tease, a slut, or a blonde under that wig." Laughed Sherry.
With that Mary grabbed a handful of her hair and a hand full of Sherry's and pulled. "See, no wig, no blonde. The closest thing to blonde is this red beaver here." patting her pubic hair. "Can't understand, dark burnette on top and flames down below."
"Okay guys, ahh girls, what's it going to be for supper. Eat out or in." I asked holding my clothes in front of me.
Sherry and Mary answered almost simultaneously, "Let's eat out so we can dress up."
"Let's get ready then. Hustle." and I left for Sherry's bedroom.