Jody Transformed
Introduction:
Jody has to dress as a woman to get a job
The job market at that time and in my area was really shitty. I couldn’t even get an interview very often, and never a second interview. I had a college degree, not that a sociology degree got me much, but there were scads of people with much more experience and better education than me applying for every available job. Hell, I couldn’t even get a job bagging groceries or flipping burgers.
My parents were separated and in the middle of a messy divorce. Neither of them had the time or money to help me, besides living a few hundred miles away. They mostly seemed concerned with screwing each other over in the divorce. As it stood, the only ones getting any money from them were their lawyers. From the looks of things, by the time it was over, they’d both be broke too.
So when my college friend Rob invited me over to have dinner with him, his girlfriend Ellen, and another friend, I accepted. It would be a good meal and with my money problems, I wasn’t sure how many of those I could look forward to. Rob and Ellen live together in a one bedroom place. I’d already begged him to let me just sleep on the sofa, and promised to stay out of the way.
“Dude, I love you and I wish I could. But if you move in, Ellen will walk out, and without her paying part of the rent and utilities, my ass will be on the street before long too.”
Still, I was getting a free meal, and I’ll take what I can get. Saved me a couple dollars that a hamburger would cost. Besides Rob, Ellen, and me, Stephanie a friend of Ellen’s was there. Stephanie was a cute brunette a couple of years older than me. She was about my height, but easily fifteen pounds lighter, and dressed very nicely. Nice ass, with some good curves and probably b-cup boobs, as best I could tell.
Rob had previously told me that Stephanie and Ellen had a thing at one time, but that Ellen decided she liked boys a lot better. That kind of surprised me, as both Ellen and Stephanie looked pretty feminine. I know that lots of lesbians aren’t very butch, but thought maybe it was just a wild fling for the both of them. Weirder things have been known to happen.
Of course during the night, my problems came up. Stephanie looked sympathetic, but also stared at me in a funny way. I told all three that if they heard of any kind of job at all, to let me know, that I’d do whatever I needed to. Little did I know exactly what I’d need to do.
Later that evening, Rob and Ellen were in the kitchen and Stephanie and I sat in the living room. Stephanie looked at me and smiled.
“Are you really willing to do whatever you need to do to get a job?”
“God, yes. In about a week, my ass will be out on the street if I don’t.”
“I want an answer from you to a couple of questions, and I want the truth. I’ll know if you’re lying, and if you don’t answer, you don’t really want a job that bad.”
“I’ll tell you whatever you want to know.”
“Have you ever thought about wearing women’s clothes?”
I blushed, which I don’t often do, and squirmed before I answered.
“When I was in my teens, I had a little fetish for women’s clothes.”
“Did you ever actually wear them?”
“I was in a play in high school, and for part of it, I was dressed up as a woman.”
“I’ll bet you were pretty convincing as a woman. Weren’t you?”
“Because I’m short and slender, I did look like one. But I caught a lot of shit from the other boys in school. They started calling me a faggot. The theatre director wanted to cast me in another cross dressing role, and I turned it down, because I already had more than enough shit in my life.”
“Any other times?”
“Before that, one time I tried on a pair of my mother’s old panties.”
“For how long?”
“I wore them to school for a few days – that was all.”
“You look like this is making you uncomfortable.”
“I like girls, not boys. How many girls want a boyfriend who wears women’s clothes?”
“You might be surprised.”
“Why are you asking me all these questions?”
“My company has a job opening for an administrative assistant. They almost exclusively hire women for that role. We only have one male admin, and he is gay, working for a gay VP.”
“Isn’t that sexual discrimination?”
“The males who apply, somehow either their qualifications are lacking, or it is felt that they don’t fit the company culture as well. Besides, if you try to apply as a guy and get rejected, I’ll deny all of this.”
“So what good does it do me then?”
“Jody is both a girl’s name and a boy’s name.”
“I caught plenty of shit for that growing up too.”
“Your hair is kind of long for a guy.”
“I haven’t had the money for a haircut for quite a while.”
“Are you really willing to do whatever it takes to get a job?”
“What is it going to take?”
“Dressing up as a woman, applying for a job at my company and putting on the application that you are a woman.”
“But that’s a lie.”
“And if they find out it’s a lie they’ll fire you, but if you don’t lie, they won’t hire you.”
“But the first time I show up in men’s clothes…”
“Your ass is fired. You’d have to come to work dressed as a woman every day for as long as you work there.”
“I don’t have the money to buy any women’s clothes.”
“I’ll spring for some thrift store buys. You’d be amazed what you can find sometimes.”
“My hair doesn’t look that feminine. I don’t have a wig or makeup. I don’t know that I can pass that well on close inspection.”
She looked carefully at me, shifting angles somewhat. “I’ll pay to have your hair styled, and for a manicure and pedicure. We’ll shave all body hair, including underarms. I think we can make you pass.”
“In a week, I won’t have a place to live anyhow.”
“As long as you follow my rules, I’ll let you stay at my place.”
“What kind of rules? And what do you get out of this?”
“You keep your feminine identity 24 hours a day, seven days a week for starters. For me, I get what I think will be a cute girlfriend.”
“But I’m a guy – I have a dick.”
“You’ll get your pleasure too, but mine is first and most important.”
“I don’t know if I can do that.”
“So the person who said they’d do whatever they had to for a job, is having second thoughts, even with the chance of a job and a place to stay.”
“And if I accept?”
“You can come home with me tonight and we’ll spend the weekend getting you made over.”
“Shit. Do I have much of a choice?”
“What’s worse, being broke, jobless, and homeless, or dressing as a woman and living with a girlfriend?”
“How long would this be?”
“If you dress and act like a woman and if you please me, it could last as long as you want.”
“Sounds like a devil’s bargain.”
“I’m no angel, but I’m no devil either.”
“I accept.”
She smiled, beckoned me over to her, and gave me a kiss.
. . . . . . . .
We went back to her place that night. It was a comfortable little one bedroom place, actually nicer than Rob and Ellen’s place. I was concerned since I know she likes women and she wants me to be a woman 24/7 for her. We had to make some accommodations, but not as many as I feared. We came in the door and we kissed and touched each other for quite a while.
“Jody, baby, let’s get you cleaned up.”
“Cleaned up? I took a shower just a few hours ago.”
“Some of that nasty body hair. It’s going to have to go anyhow, so let’s get rid of it up front.”
She took my hand and led me to the bathroom, where she had me take off my clothes. She shaved my face very clean, then put depilatory cream all over my chest, arms, and legs, plus a little on what small amount of back hair I had. It stung a bit, but wasn’t too bad. After it sat a bit she had me wash the cream and hair off. She shaved very carefully around my dick and balls and around my ass. She also shaved my underarms. I felt weird as hell, but I knew if I wanted that job, I’d have to do that anyhow.
She kissed me regularly throughout this and stroked my hairless body afterwards. Stephanie was quite sweet, and when I was hairless to her satisfaction, she led me into her bedroom and we lay down on the bed. She had shed her skirt and top during the hair removal. She said it was only fair that if I had to take off my clothes that she should take off most of hers too. I sure as hell had no argument with that.
She began kissing my lips then worked her way to my ears, and my neck. I’d never had a woman do that to me before. I found myself getting hard just from the way Stephanie kissed me. She got down to my chest, then kissed her way to my nipples. I’d never thought of them as being all that sensitive, but the way she kissed them and sucked on them, it sure felt like it. As she kissed my nipples and stroked my body, I had a tingling feeling run through me from head to toe. I didn’t cum, but it was the damnedest pleasurable feeling that I’ve ever had.
She had me unhook her bra and take it off her. I then did to her what she’d done to me, and began kissing her from her lips down to her boobs. As I got to her breasts, I paused and smiled, then took one nipple between my lips, kissed it and sucked on it as she moaned and squirmed. I brought a hand up and caressed her other boob as I kissed and nibbled on the first one.
As she started to mellow out, I switched and began kissing, sucking on, and nibbling the second nipple while fondling the first one. She ran her fingers through my hair as I worked her breasts over, until she stiffened and I could feel her muscles rippling through her abdomen as she panted and moaned and arched her back.
As her orgasm eased up, Stephanie lifted her hips and I took my cue to pull down her panties. I got them all the way off her and she stroked and gently pushed my head down to her pussy. As I moved down, she spread her legs wide. I put my hands under her boobs, squeezing them, before slowly bringing them down her body. I came down her sides, then onto her thighs and to her inner thighs just below her pussy. I massaged her inner thighs as she moaned and thrust her hips forward, then back repeatedly.
“Please, Jody. Touch me, lick me. I need you.”
I moved my face forward to her cute shaved pussy. I kissed it, as though her labia were the lips on her face. She was already dripping wet between her legs, and I tenderly licked her juices from her pussy, from the bottom up to her clit, which was just starting to peek out of its hood. I gave it a quick nibble, before moving down to lick her again, this time getting my tongue slightly between her pussy lips.
Stephanie wrapped her legs around my neck, pulling me so close I could barely breathe as I licked her pussy and sucked on her clit. She began panting even more, making indecipherable noises and pulling my face tight to her cunt as she pumped her hips back and forth, fucking my tongue which was between her pussy lips. I could feel her pussy tighten around my tongue, as she held me tight and even squirted a bit as she came.
“Jody, that was wonderful. I know you deserve to get off too, and you can. I hope you don’t mind.”
“Why would I mind, love?”
“I can’t take birth control, and I don’t dare get pregnant.”
“So how should I get off?”
“You can have my ass. I have some lube in the table beside the bed. I know lots of women don’t like anal, but I don’t mind. Is that okay?”
I wanted nothing more than to fuck that little pussy unmercifully, but I smiled and nodded, then reached over to get the lube. She rolled onto her stomach, the raised her hips to give me better access to that cute ass. I put some lube near her bunghole, then used first one finger then two to work it into her. Her ass was tight, but as my fingers worked her over, she began to loosen up. She moved her ass back and forth as I lubed her up, then rubbed some lube onto my prick.
“Fuck my ass, please. Pound it, make me scream. Fill me up with that dick of yours. Cum deep inside me.”
Who am I to turn down that kind of request from a lady? I came up behind her and teased her asshole with the end of my prick as she squirmed and thrust her as back, trying to ensnare me. I eased forward and put the head of my cock just inside her ass. She gasped, then made the most contented sigh. I slowly edged it back then forward getting into her an inch at a time.
Finally I made it balls deep into her ass, then began to gently fuck her ass, as she fucked me back. Her ass was so tight, it felt absolutely marvelous – tighter than any pussy I’d ever fucked. I’d still have rather had her pussy, but this felt damned good. I could feel it starting to build as I neared my own climax, and matched her moaning with my own.
“Oh God, Steffie, I’m going to cum.”
“Do it baby. Fill my ass with your cum.”
As I came, I plunged deep into her and held her hips tight, to cum just as deep into her as I could manage. I almost slumped across her back as I came. As my cock stopped spurting and throbbing in her, I rolled off to one side, and Stephanie rolled the other way to face me. She kissed me and stroked my face as I came down off my post-orgasmic high.
We kissed and caressed each other for a long time, before she rolled over to snuggle up to me as the little spoon to my big spoon. I pulled her tight and held her boob as we drifted off to sleep.
. . . . . . .
The next morning, I awoke to Stephanie kissing me. I ate her out again, then fucked her ass again. No, I might not get to fuck her cunt, but I was still getting to fuck her and cum in her. After a bit of bliss, we showered together and soaped and stroked each other as we showered. She used her hand to get me off again in the shower, and I fingered her to another orgasm. We teased, tickled and made each other feel good as we dried off, then Stephanie said we needed to work on getting me ready.
She started by brushing my hair differently than I normally would. She wouldn’t let me look at it until she was done, then I was amazed at how much more feminine my face and hair looked with what she’d done. She took me back into the bedroom and said we’d need to do some clothes shopping, but I needed to look more feminine to do that.
She got a bra that was not a wonderful fit, but which she had me put on, then she stuffed the cups to make it look like I really had boobs. She got what appeared to be a pair of heavy panties that smoothed my penis and hid it between my legs, so it almost seemed not to be there. She them had me put a pair of lacy panties on over those. I looked in the mirror and between the panties, the bra and what she’d done to my hair, I was shocked at how feminine I already looked.
She found a skirt that I was able to get into, and a top that seemed to emphasize the boobs I seemed to have. She sat me down and shaped my eyebrows, then put foundation, concealer below my eyes, then highlighter along my cheekbones, hairline and such. She put eyeshadow on my eyelids and some light eyeliner, and finished with some light pink lipstick. I would never have recognized myself, and was astounded at how I looked.
She managed to find a pair of flats that were backless and were not uncomfortable for me to wear. Stephanie got dressed and we stood side by side facing the mirror and for all the world, looked like two beautiful girls getting ready to go out.
We hit one thrift shop very near her place and found some flats and low heels that fit better than Stephanie’s shoes did. She bought me about four pair, only paying a few dollars per pair. We hit another place that had tops, some with the original tags still on them, again for only a few dollars each. We got half a dozen or so tops, and even found some nice skirts that went with them. I went into the women’s dressing room to try on the items, and nobody even looked twice at me.
By the end of the shopping trip, I had pretty much a wardrobe of clothes, and excepting bras and panties, Stephanie had not even spent a hundred dollars. We hit a discount store and got several bras and pairs of panties for not tht much money. She hit the drugstore for some discount cosmetics. She said that the name brands were better, but for the moment, I’d be fine with lower tier goods.
“I should go back to my place and get my clothes and stuff, if I’m going to stay with you.”
“Personal effects, perhaps, but NO clothes. You will be dressing like a woman for the foreseeable future. Don’t tempt yourself with male clothes. You can’t wear them anyhow.”
“That kind of assumes I get the job.”
“You’re going into apply for the job Monday. If you flop, there’s still time to get a few clothes before you hit the streets.”
“If I don’t get the job, you’ll throw me out?”
“You’ll get the job if you really want it. And you’ll dress as a woman at all times if you live with me.”
“I stay with you, and I live by your rules.”
“Exactly.”
Stephanie was very stern as she laid down the law with me. But once I made it clear that I accepted it, her face softened, she smiled, and kissed me. We took the clothes back to her place and then she took me to a salon where they cut my hair to look even more feminine than Stephanie had made it. She then had the stylist work with me a bit so I knew how to style it myself. I never realized how damned much work it was for a woman to take care of hair and makeup.
From there she took me to a nail salon where they gave me a manicure and pedicure. She had them paint my fingernails and toenails a bright pink. She told me that a red was a little much for an interview, that I’d look prettier and more businesslike with the pink. By the end of the day, with the new shoes, clothes, makeup, and nails, I looked gorgeous. I fell in love with myself every time I looked in a mirror.
Of course as time went on, I began to look for the flaws in my appearance in the mirror, but those first few days, I felt beautiful, if weird as shit. We went to lunch and Stephanie had to teach me how to sit ladylike. I also had to learn how to pick things up without showing the world my panties. By the end of the weekend, I’d learned how to smooth and tuck my skirt and cross my legs to stay modest.
Stephanie made me spend part of a day just learning how to do and touch up my makeup. She took me to a little shop and bought me a set of breast forms with a skin tone close to my own, along some medical grade adhesive. The clerk paid little attention to me as we got them and Stephanie told me that mastectomy patients used them, along with cross dressers and some transwomen. When we got home she had me take off my bra and she used the medical adhesive to glue the breast forms to my chest. I was now a c-cup and since the skin tone was close, I could even show a little cleavage.
All this sounds like I was gung ho, but a real part of me was rebelling all the way. It was like a whirlwind though. She bought me all sorts of things, which I sure didn’t have the money for, but which made me look very much like the woman she said I needed to be. Now my voice was never too deep, more like a high tenor, though I could sing a low alto. Stephanie had me practice keeping my voice soft and higher pitched. If I stopped to think about it, I felt ill, but I hated the thought of being homeless and loved fucking Stephanie, even if I only ever got her ass.
. . . . . . . .
Come Monday morning, we woke up and began getting ready, Stephanie to work and me to apply for that job. We showered, dressed, did makeup, and then she took me in with her to her office. What I learned was that Stephanie was no VP, so she didn’t have serious pull, but she was a department manager, so she certainly had some influence.
I filled out my employment application, making sure to show my sex as female and went through a preliminary interview with Human Resources. I was bright, cheery, positive, and eager to work and do a good job. I passed the first interview and they quickly moved me to a second interviewer, who also liked me. The third interviewer was the VP who I would be working for, if hired.
The VP was a middle aged man, with a few extra pounds and a receding hairline – seriously receding. When I met him, his eyes got bigger for a few seconds, and he licked his lips. I thought, oh shit, what have I gotten into. He was both very cordial and very proper. He saw that my marital status was single, so I mentioned that I was seeing someone and that we were serious. I wanted to discourage any thoughts he might have about trying to seduce this babe he was interviewing.
As it turned out, he was married and his wife kept him on a short leash, but he sure as hell liked to look and even fantasize about hot women. And it seemed in his view I was one hot woman. As it turned out the fact that Stephanie referred me, helped me get the job, and paid her a bonus for the referral, which was more than she’d spent on my clothes and such. She said I’d owe her nothing for the clothes, and she even gave me some of the referral bonus so I’d have some walking around money until I started getting regular paychecks.
We had lunch together, which the VP saw, and Stephanie discretely made it clear that I was a friend of hers and that she wouldn’t appreciate any untoward comments or actions directed at me. I got the job, and they wanted me to start the next day.
I hung out in the area of her office until she got off work, though I had to deal with several nice looking men hitting up on me. They were professional men, but they wanted to take me out for dinner and drinks, and god knows what after. Actually I knew what, but I knew that would not go over well. Even if I was inclined toward guys, which I wasn’t, one look at my prick, and I’d probably get the shit beaten out of me.
. . . . . . . .
It sounds like I settled right into being a woman, which was far from the truth. I had to constantly think about which bathroom I was going into, how I greeted men I met, how I spoke with them, beyond coping with the cognitive dissonance of living as a woman. I didn’t have very thick hair on my face, but had to be super careful about shaving so what I had wasn’t obvious. I was using depilatory creams and shaving underarm hair more than I’d have realized.
It got to be a nuisance and I complained to Stephanie. She said there were drugs that would help minimize the body and facial hair, if I wanted. I said absolutely, never even thinking about what side effects there might be. What she did was get me put on t-blockers and female hormones – hormone replacement therapy is what they call it. It’s what transwomen take, and I signed on, never thinking.
Sure enough the facial hair decreased, and the body hair got much finer than it had been. I started getting fat in places more typical to women, including developing breasts. When I realized that, it bothered the shit out of me. I was still a man – I still had a prick. Fake boobs were find, even gluing them on was fine but I was queasy about having my own real ones.
Stephanie worked to calm me down and I found the boobs were actually quite sensitive. When she stroked my boobs it felt like electric shocks going through my body. Having her play with my boobs brought me to an orgasm, though not an ejaculation. Our sex play changed along the way. I still fucked her in the ass, though she now was using a strap-on to fuck me in the ass as well. I wasn’t sure I liked that all that much, but I was far too deep to back out now.
My hair grew out more and we had it styled in a longer women’s style. I kept getting manicures and pedicures, and it began to feel natural to have my nails painted. What little facial hair I had left, we had removed my laser. So my face was as smooth as Stephanie’s, and with no more shaving. It even felt like my hips started to change shape. It looked like I now had a woman’s ass and hips.
Once in a while, Stephanie and I saw Rob and Ellen. Rob looked at me weird any time we saw them.
“Jody, I know you’re the guy I went to college with, but I swear to God, when I see you like this, I want to fuck you. You’re one hot chick.”
“Rob, I’m not into guys and I never have been, and I’ve still got a dick – no pussy.”
“Damn girl. My eyes still say you are really fuckable.”
“Bro, don’t think that way. I’m not anything you want to fuck, and I sure as shit don’t want to fuck you.”
That was mostly true. Part of the effect of the hormones was that I began to find men more attractive. They sure seemed to find me more attractive as well. If Stephanie and I went to a club, unless it was one frequently by lesbians, I was constantly having men ask me to dance and having men offer to buy me drinks and wanting to take me to dinner. The killer was when I looked at one handsome man and remembering Stephanie’s strap-on, could almost feel his dick in my ass. That scared the shit out of me, and I tried to quit even looking at guys after that.
Even Stephanie called me ‘girl’ when we were alone.
“Why do you call me ‘girl’ when there’s no one around to hear. You know I’m a guy.”
“I don’t dare get in the habit of thinking of you or speaking of you or to you as a guy, or I might do it by mistake when people are around, then we’d have real trouble. Besides, except when you take your special panties off, you look one hundred percent girl.”
Stephanie got promoted to VP, and I moved from being an administrative assistant to being an assistant department head. We were jubilant, until she started thinking.
“Jody, your driver’s license and all your docs say you’re a man.”
“But aren’t I?”
“If anyone at the company looks deeply, you lose your job, and it might cost me mine too.”
“So what can I do?”
“File, the way you would if you were trans, and have all the docs changed to female.”
“But I don’t know.”
“Girl, right now if you got arrested, they’d throw your ass in a man’s jail. What do you think those men would do to you?”
“Why would I be arrested?”
“Who knows? And what if you’re driving and get stopped? What do you think the cop would do looking at you and looking at a license that shows you as male?”
“I’d be in a world of shit.”
“At the very least. Please. Do it for your protection and for me.”
. . . . . . . .
I was now legally a woman, at least according to my driver’s license and birth certificate. It felt weird as shit, but in many ways it was safer. Besides, in the way that counts, I was still male, even if the equipment seemed to be faltering a bit. I wasn’t sure why, but I was having a harder time getting it up and keeping it up. It didn’t seem to bother Stephanie that much, but it kind of disturbed me. I mean, I have a dick, I just can’t fuck anything with it. I still got pleasure from sex, just no ejaculation.
Work was going well. I was made department head and was running my department so it became more efficient and more effective. Management seemed to love my performance. Stephanie was also doing well and was now responsible for the development and rollout of a new product. She spent months and months working on creating this new product and making sure it worked right and was what the market wanted. There were some similar products, but ours was better – she made sure of it.
While the new product was better, it also cost more to make than competing products, which meant we had more trouble competing on price. We could match what the competitors were charging at rollout and still make money, but if they started a price war, they could afford to undercut us. That made the rollout dicier.
There were four companies which would be the primary market for the product, and the market leader for that industry would likely determine which way those four would go. If they went to the less expensive alternative, so would the others to compete on price. If they went for our product, the others would eventually follow to compete on quality.
After extensive negotiations, a senior VP for that company came to town to meet with Stephanie and negotiate with her. Stephanie and her team, spent a couple of days meeting with Brad and his team. Brad seemed to like our product but still seemed not to be convinced. At the end of one work day, Stephanie and Brad were to meet for dinner and Stephanie invited me to join them.
I was flattered. This was a big deal. This product could move us ahead of our industry if Brad signed on, and that would make Stephanie’s career, and give us both real job security. I dressed in my best and classiest outfit and did my hair and makeup accordingly. Brad was about 6’1” and 170 pounds with a lean athletic physique and a handsome face. In spite of myself, I began to find myself drawn to him.
We went to the best restaurant in town and had what was probably the best meal I’ve ever eaten. There was some business talk along with a lot of personal talk. Among other things, Brad seemed quite taken with me and told me repeatedly how beautiful I was. Frankly, it was almost embarrassing. We ate, we drank, and we talked for hours. Well mostly Brad and Stephanie talked while I watched and listened. Finally, around 11pm, Stephanie hit Brad with a biggie.
“What would it take for you to make a commitment to buy our product?”
“You seem to have a good product, assuming it performs the way you say it will and the way the limited tests seem to show.”
“It will. We’re willing to guarantee it.”
“It is still a gamble on our part. We’ve all seen products that looked wonderful in testing that failed in real life situations.”
“We won’t fail, but even if we did, you could go back to your current supplier.”
“We have to redesign our product to use yours. Then we have to retool our plant. If you fail, we get beaten by our competitors.”
“And if we succeed, and we will, you have a leg up on your competition.”
“It’s still a gamble, and I’m putting my career on the line with this decision.”
“We will do whatever we need to in order to make this deal work.”
“I believe you will. I’m just hesitant.”
“Please. Tell me what you want. Name it.”
“Perhaps if your beautiful friend Jody were to come back to my hotel room and spend a little time convincing me, that would be enough to close the deal.”
I couldn’t believe Brad would even suggest something like that. I turned at looked at Stephanie. She smiled at me and turned back to Brad.
“Jody is trans, and she hasn’t had the surgery.”
Brad turned to me and just looked at me for a minute, then smiled.
“That’s a little kinky, but I’ve been known to do kinky.”
I sat there shocked. Brad wanted to fuck me, even knowing I had a prick. Worse, Stephanie seemed to be considering it. I was speechless.
“Brad, may I have a minute to talk to Jody?”
“Certainly, Stephanie. I need to use the restroom anyhow.”
Brad gave me a huge warm smile, leaning over toward me as he got up. He stood, still looking at me, licked his lips, turned and walked to the restroom.
“Stephanie – darling. You can’t expect me to just let this man fuck me.”
Stephanie scooted over, stroked my face, and kissed me.
“Jody, honey. This deal is absolutely critical to my career, your career, and to the whole company. If it weren’t, I’d never even consider it. But it is, and I need you to make a sacrifice for me – for us both. I swear to God, I’ll make it up to you – any way I can. I promise I will, but please, please just do this for me. I don’t like this any more than you do, but we have to.”
“It isn’t you he’s planning to fuck. I’ll let you go fuck him to close the deal.”
“Honey, he doesn’t want me. He wants you. If I could do this in your place, I would, but I can’t.“
Stephanie was stroking my head, my neck, and my back, while kissing me. I was crying. Here I was with my lover pimping me out to close a business deal. I saw Brad starting to walk back to the table, and I stood up and ran to the women’s restroom, almost knocking over a man on the way. I went in a stall, closed the door, latched it, and just sat on the toilet weeping. After a couple of minutes, I heard the door open and heels walk across the floor to the door to my stall, which apparently was the only one occupied.
“Honey, please. I know you hate this. I hate it too. But I really need you to do this for me.”
I got up, opened the door to the stall to look at Stephanie standing there. She walked me over to the sinks and the mirror. My eyes were red from crying and my makeup looked terrible. She helped me clean my face and fix my makeup, all the while talking to me in a soothing and conciliatory voice, stroking me gently, and kissing me.
After a few minutes, I had regained my composure and didn’t look quite so horrible. Stephanie put her arm around me and walked me back to the table. As we got there, Brad got up and held the chair for me as I sat, then leaned over and gave me a quick kiss. Brad and Stephanie both sat back down.
“Brad, I don’t think Jody has ever been with a guy before. She’s stuck with women lovers up until now.”
Brad turned to me with a sweet smile, leaning forward.
“I’ll be as sweet, gentle, and considerate as possible. I want this to be good for you too.”
Stephanie stood up, and I was shocked and stood as well. Brad also stood and Stephanie came over to me, hugged me and gave me a passionate kiss.
“Jody, honey. I’ll see you tomorrow. You know I love you dearly. Please, please.”
With that, Stephanie turned and walked away. I stood there and quickly Brad put his arm around me. He pulled me tight to him, and gave me a passionate kiss. I hated it, but found myself responding to him, and kissing him back. After a minute, he walked me to his car.
He was staying in a luxurious suite in a top rated hotel. The hotel has an ‘elite’ floor which ordinary folks can’t even go to, and he was in that area. There was an outer area and a separate bedroom. Brad walked me into the bedroom, closed and locked the door, then took off his suit coat and tie and hung both of them up.
He walked back over to where I was standing nervously. He stroked my face and put an arm around my waist and gave me a quick kiss.
“You really are beautiful, and I’m sorry if this has upset you. This is new to you, and it’s new to me too. I’ve been with women but never with anyone who has a package. I wish you had a pussy, because I’d like to do things to it and make you feel as good as being with you makes me feel.”
He began kissing me and stroking my back as he said that. He actually was making me feel good, even if it wasn’t what I wanted. While stroking and kissing me, he managed to unzip my dress, and eased it off me. I stepped out of it, and he quickly hung it in the closet, also taking off his pants and hanging them, before returning to me.
“Baby, I want this to be a night you remember, but for the right reasons.”
I was in bra and panties, while he was in boxer briefs as he walked me over to the king size bed. He unhooked my bra and slipped it off before lying down on the bed and pulling me down on top of him. I wanted to hate Brad. I wanted to hate what he was doing to me and what he was going to do to me. But he was so tender and loving that I couldn’t hate him.
He kissed me, not roughly as I’d expected, but sweetly yet passionately, exploring my mouth, my lips, and my tongue, drawing me deeply into the kisses. Stephanie and I had shared thousands of kisses, and I’d kissed other women more than a few times, as well. I loved all that, and still wanted to kiss and be with women, but I’d never had kisses like this. I can’t say Brad was better, but he was wonderful in his own different way.
He kissed across my cheek to my ear, where he kissed and nibbled on the earlobe before kissing his way down my neck. He kissed his way down to a boob, circling it with kisses, licks, and nibbles, slowly circling and working his way to the center and to my nipple. When he took my nipple in his lips, it was almost like electric shocks running through my body. I felt like I levitated off the bed. I know I arched my back and wanted him in a way that I never thought I would ever want a man.
He took his hand and teased and stroked the other breast as his mouth made sweet love to the first one. I no longer was even sure who or what I was or what I wanted. All I knew was that I didn’t want Brad to stop. After a bit, he switched sides, kissing the boob he’d been fondling and now fondling the boob he’d been kissing. He continued until I was gripped by waves of pleasure running through my body. Every nerve ending was alive and they all were consumed in pleasure.
As I came down off my high, Brad moved back up, kissing my lips again for a while, before slipping off his boxer briefs and rolling onto his back.
“Please, baby. Do me. Make me feel as good as I made you feel.”
I’d never touched another man’s dick. I’d certainly never had one in my mouth – never even considered it. I wasn’t thrilled about the prospect now, but I was still on such a sexual high that I couldn’t refuse. I slid down his body to where his prick was standing as hard as I could imagine one being – since I couldn’t seem to get hard any more, it was difficult to compare, but I don’t think I had ever been harder.
I looked at it, then looked up at Brad’s face. He could clearly see my ambivalence, and I could see his eyes asking ‘please’. I moved closer, taking the head between my lips and easing my lips back off. I heard Brad moan, and repeated it, going a little past the head the second time. I could taste the saltiness of his pre-cum on the end as I gradually took more and more of his prick in my mouth, until I had almost the whole length in.
I couldn’t quite get all of him in without gagging, but did what I could. I slowly took him in and out, giving him just a hint of teeth, as he had done on my boobs, not to hurt, but just to tease a little. He was clearly enjoying it, pumping his hips in rhythm with me, moaning, and holding my head. I could tell he was getting close as he got more urgent.
“Faster, please. I want to cum in your mouth.”
At this point, if I had any male dignity, it was long gone. I’d been kissing this guy, letting him suck my boobs, and I was now sucking him off. I might just as well let him cum in my mouth. I picked up the pace as fast as I could, fucking his dick with my mouth. He held my head tight with his dick so far down my throat I could barely breathe as he shot what felt like a gallon of cum in my mouth.
He eased his hold on my head after ten or fifteen seconds, and I gasped for air and eased back and swallowed his load, though it took two or three swallows to get it all down. I gradually eased him out, cleaning him off as I went. His dick was already softening as I gave the head one last kiss and crawled up the bed alongside Brad. He kissed me, and I was sure he could taste his own cum in my mouth as he did, and caressed my boobs more as he recovered.
“Thank you, baby. Not only are you beautiful, but that was great.”
Brad pulled me on top of him and continued to kiss me as he stroked my back and my ass, while he fondled my boobs. He made me feel so good, I no longer cared that I was with a guy. All I knew was that I was fucking someone who made me feel wonderful. He was easily as good a lover as Stephanie was. And the last time I had better sex was when I could still get a hard-on. After a little while, I could tell that Brad was hard again.
“Baby, I need you. If you had a pussy I’d fuck that. Since you don’t I want to fuck your ass.”
“Do… do you have lube?”
He rolled me off him, smiled and reached in a drawer by the bed and pulled out a tube of lube. I bit my lip, then he kissed me and rolled me onto my hands and knees. He came around behind me and gently petted my back and my ass, as he pulled down my panties. I lifted up so he could get them past my knees, then he pulled them the rest of the way off.
I knew the drill. Stephanie had been using her strap-on to fuck my ass for almost two years. Brad got me to spread my legs farther apart to give him better access, then he used a glob of lube around my asshole and eased a finger into me. As I relaxed, he eased two fingers into me, lubing me up and stretching me out.
I looked back and could see my limp little dick hanging between my legs, as he slathered more lube all over his dick. He got up behind me and I could feel his super stiff rod around my ass and near my useless prick and balls. He grabbed my hips with one hand as his other hand guided his cock to my backdoor. He slid the tip just into my ass. He let go of his dick and grabbed my hips with both hands as he slowly pushed his prick in me an inch at a time, easing back a little several times as he did, then slipping it a bit further in.
Brad was bigger than Stephanie’s strap-on, and I couldn’t believe how wonderfully full I felt as he got balls deep in my ass. He paused once he was all the way in.
“Baby, you are so fucking tight and so fucking wonderful, I can hardly stand it.”
With that, he began fucking my ass, slowly and gently at first, then faster and harder as we went along. As he did, he leaned forward and slid his hands from my hips to my boobs, which he squeezed and fondled as he pumped his dick in my ass. After a little while, he began to breathe harder, panting and moaning, which I could hardly hear over my own moans. He eased his hands back to my hips and held me tight as he plunged his cock deep into my ass where I could feel him throb and spurt as he came in me.
I was surprised he had anything left after the way he’d cum in my mouth. I could feel his weight on my back, as he lost himself in his orgasm. Finally his dick stopped throbbing, and he lifted his weight slightly off me. He kissed the base of my neck, then kissed his way down my back as he eased himself out of my ass.
Brad rolled over onto the bed, and pulled me back on top of him. He kissed and stroked me as we both cooled down, and I could feel his cum starting to leak out of my ass.
“Baby, I know this wasn’t how you planned to spend your night, but thank you. Being with you is delicious.”
“I didn’t think I like it, but I really did. I’d say you were the best male lover I’ve ever had, but since you’re the only one, I’m not sure how much that means.”
He gave me a little smile that told me he’d gotten the joke, and kissed me again.
“I never thought about being with someone trans before, and certainly not someone who still had a prick, but you were so beautiful, I couldn’t resist. And it was worth it.”
“It was worth it for me too.”
“You’ll stay the night?”
“If you want me to.”
He kissed me and hugged me very tight. I could feel his cock beginning to stir again.
“As great as this was, I really wish you had a pussy. I’d love to fuck your pussy.”
“I wish I had a pussy too.”
I couldn’t believe I said that, even as I did say it, but I meant it.
“If you’re serious, baby, I’ll pay for the surgery and I’ll make the arrangements. I just want a chance to fuck that pussy, once it’s healed and ready.”
“And I want you to.”
I knew I had started to feel some attraction to men, even before that night, but I’d tried to ignore it and deny it. I was still attracted to women, and felt certain I always would, but now I was willing to swing both ways.
I sucked Brad off again, though he sweetly washed his dick off before I did. I guess he didn’t want to taste his shit on my lips any more than I wanted to taste it. He fucked my ass a couple more times before we were both exhausted and curled up together in bed and drifted off to sleep.
The next morning, I woke up to Brad caressing my boob. I moaned in pleasure and rolled over to kiss him. We kissed and stroked each other for a while before he fucked my ass once more. It was starting to get a bit sore from all the attention it had gotten between last night and that morning. After we cooled down from that, he swatted my ass, and told me to go get cleaned up, and he’d see me at lunch.
. . . . . . . .
Brad signed the purchase contract. He later told me that he probably would have anyway, but he was so taken with me, that he wanted to see if he could sweeten the deal. Brad, Stephanie, and I met for lunch and he gave Stephanie the signed agreement.
“Jody, babe, I talked to a friend of mine. If you are serious about the surgery, he has a friend who’ll schedule it for this Friday.”
Stephanie looked shocked, so Brad and I had to explain.
“Brad offered to pay for gender correction surgery for me, and I accepted.”
“What does that mean for us?”
“Stephanie, darling, you’ve had other women lovers. And I’ve been a woman in every way except between the legs. It isn’t a problem for me. Do you have a problem with it?”
“I was concerned that you were going to leave me for Brad.”
“No, but every once in a while, you might have to share me with Brad. Since you sent me to be with him last night, I’m not sure why that would be a problem.”
Stephanie leaned over and kissed me tenderly, and stroked my hair.
“As long as you’re my girl, it’s fine.”
The following Friday, Brad escorted me to the office of the doctor. Stephanie couldn’t be there that day, but would be there the next day. The doctor had me strip, and checked me out. He stretched out my limp dick and said there was enough there for a decent sized vagina. I would have trouble taking a man who was more than seven inches long, but I didn’t see an issue. Most men are smaller than that, and Brad was about six and a half, and anyway I didn’t plan on fucking any other men besides him.
The doctor said it was obvious that I’d been on hormone replacement therapy for well over a year, and I showed him pictures of me from more than a year earlier dressed as a woman. Apparently the AMA folks are real sticklers for making sure that someone who gets the surgery has been living as a woman for over a year. I clearly had, so there was no problem. I could even show where I’d been on HRT for a year and a half.
“Jody, are you sure you want to go ahead with this? This surgery is not reversible and even if you change your mind after surgery, you will never have a natural penis again.”
“My penis is useless as it is. I can’t get a hard-on any longer and the last few times I did, I couldn’t keep it long enough to do any good.”
“That’s occasionally one of the side effects of HRT. If that’s your only concern, you could take some testosterone supplements, and you might be able to get an erection again.”
I thought about it, looked at Brad, then turned to the doctor.
“No, doctor, I want to go ahead with this.”
“Well Jody, I see that your breasts a b-cup. Would you like implants to make them bigger?”
“I’ve been happy with them. Brad, what do you think?”
“Baby, if you’re happy with them, so am I.”
I signed a bunch of papers, authorizing God only knows what all. The doctor told me not to bother getting dressed, that the surgery would be that afternoon, and they would get me a hospital gown in the meantime.
“I’ll give you two some private time together. The nurse will be in shortly to begin prepping you for surgery.”
The doctor left and Brad kissed me and told me that he and Stephanie would be with me all the way.
I can’t tell you much about the surgery, as I was out of it. As the doctor explained it, they remove the erectile tissue in the penis, invert the skin and use it to form the new vagina. They use the skin around the balls to form the labia. They have to be careful through the process. Done improperly, the colon can be punctured, since they are displacing some of that for the new vagina.
This doctor was one of the best and he assured me there was little chance of problems, though there was no surgery that was 100% safe. They pack out the new vagina to give it shape for the first couple of days. After the packing was removed, I had to begin using a dilator to keep the vagina stretched out as it should be.
“You won’t really be able to use the vagina for sex for probably three months or so. We’ll do regular follow ups to make sure everything is fine and tell you when you’re ready.”
“What about anal?”
“We are doing a lot of work down there and you’re going to walk with difficulty for a while. I would avoid anal for several weeks, at least.”
“Anything else?”
“You won’t have the normal flow of fluids that other women have, so you’ll need to use lube for vaginal sex, and you’ll probably want to douche after your boyfriend comes inside you.”
Brad held my hand as I went under, and I woke up to Stephanie holding my hand. My legs almost buckled under me when I first tried to stand, but Brad, Stephanie, and a nurse helped me stay on my feet as I walked the tiniest bit. By the time I left the clinic, I could walk, at least for a hundred yards or so. It was weeks before I felt halfway back to normal.
Stephanie and I went home and she nursed me for a week, before returning to work. I stayed out another week before coming back. It took just over three months before the doctor cleared me for vaginal sex. Of course Stephanie used her strap-on to inaugurate me. She had to be gentle, but I was surprised how great it felt. I had my first vaginal orgasm courtesy of that strap-on.
A couple of days later Brad came to town to fuck my pussy, just as I’d promised. It was funny, Brad and I had fucked several times that first night, but somehow I was worried that he’d be disappointed in me. Brad was as sweet and tender as ever, as he kissed me and slowly undressed me and himself. As before, Brad spent a long time kissing and petting me.
He spent a long time kissing and sucking on my boobs, before he even touched my pussy. He stroked it sweetly and gently, and between that and what he was doing to my boobs, I had my first orgasm that night.
I was as nervous as a virgin as Brad ranged over me, lubed up his dick and began to ease it into my pussy. Stephanie’s strap-on was nice, but a real prick felt amazing as he slowly entered me until I could feel his balls against me and his loins tightly up to mine. I bit my lip and looked at Brad, who smiled and kissed me.
“Baby, you are beautiful and wonderful, and I’ve been waiting for this for a long time.”
With that, he began fucking my pussy, slowly at first and picking up speed. It felt so good, I couldn’t even remember why I’d ever been hesitant to be with a man. I couldn’t believe it as I felt my pussy tighten around his prick and my muscles contracted and released, starting at my pussy, running up through my torso, and down both arms and legs. I was fucking him back just as hard and fast as he was fucking me, when he plunged deep in and I felt him cum deep inside me.
A little later I had my first 69 with a guy as Brad licked his cum out of my pussy as I licked it off his dick. Brad and I fucked more times that night than I could count, including fucking my ass, once for old time’s sake. I knew I’d never leave Stephanie, as long as she didn’t mind sharing me with Brad occasionally. I know I’m going to enjoy sharing my body with them both for as long as they want me.
