Jody Transformed

My name is Jody. When this all started I was a 22 year old man who was unemployed, unable to find a job, and about to be evicted because I hadn't paid my rent. I was about to the point where I was going to beg for money on street corners and sleep under bridges at current rates. That was dangerous because I was only about 5'5" and 140 pounds, and not at all athletic.

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.