Evolution of Keri

This story includes cross dressing, feminization, gender change, non-con, and sex between a male and a trans female. If you object to any of those, please skip this story.

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I’m Keri and this is my story. I was assigned male at birth and named Kerry. I know that Kerry is used by both males and females, but I wanted to distinguish who I am now from who they thought I was. I was raised as a boy, but knew I wasn’t what they thought I was. I also knew it wasn’t safe or good to try to be anything else.

Some people say it’s a choice. I know better. When I was born, the doctors said I was a boy. From my earliest memories, I knew I was a girl. My parents, my friends, my neighbors, everyone I knew tried to tell me that I was a boy. I always knew better. When I tried to dress as who I really was, people hurt me. My parents spanked me. Other kids beat me up. Some kids were satisfied just calling me queer.

It hurt me, but after a while, just to stay alive, I pretended to be the boy they said I was. I never liked sports, or any of that stuff, but I dressed in boy clothes, and played with boy toys. Sometimes I thought it would drive me crazy. I just wanted to run away -- away from my home, away from everyone I knew, even away from life.

I never actually tried to kill myself, though I thought about it. Sometimes I thought very long and hard about it, but in the end, I felt that somehow, some day I’d have a chance to be what I really was. The worst part was when puberty hit. The other girls got breasts, and started to have periods. I started getting hair in places where I didn’t want it, among other things.

It really pained me -- it pained me a lot. I wanted to have breasts. I wanted to wear skirts and dresses. I wanted to wear cute bras and panties. None of that happened. I tried to just dress androgynously. Everyone wears jeans and tee shirts, so I did that. I wished for more, but at least no one paid attention to me and no one tried to hurt me.

I found boy’s sport style briefs -- not colorful, but closer than jockey shorts to what I really wanted. There were some that were more colorful, but I knew that I’d catch a lot of grief if I wore those, even though they were for boys or men. While I was at home, while I was in high school, I’d play it straight and try to hide who and what I was.

When I graduated from high school, I moved out. I was 18 and I’d been working part time and saved some money, so I moved far away from home. I had let my hair grow as long as my folks would let me, though I wore it the way most boys wore longer hair. I got a scholarship that paid a lot of my college expenses and I worked to pay what I could of the rest.

I couldn’t afford a place of my own, so I lived in dorms with males. There was no way to dress or act as I really was, not in a dorm. Dorms can be brutal and the denizens of dorms will pounce upon and maul anyone who seems too different. For my own survival, I pretended to be like all the others. It caused me some real pain, but not as much pain as I’d have suffered by being the real me.

When I graduated, I had some debt from student loans. I managed to get a job, but between shitty wages and debt, I couldn’t afford my own place and had to share a two bedroom place with someone. Bret was an okay guy and didn’t give me a lot of crap. He wasn’t a slob at least in the common areas and cleaned up after himself in the living room and kitchen.

Unlike me, Bret seemed to have some social life. He went on dates and had some friends he’d meet occasionally. He worked but his hours tended to be a little different from mine. He would occasionally tell me he was going to be out for the evening, which pleased me to no end, though I tried to hide that fact.

While Bret might seem to be a nice guy, I had no intention to be at all girly around him. I had a few ‘alternative’ clothing items, skirts, blouses, panties, bras, and flats, along with a little makeup and a few toys. I never used any of that if he was going to be home. When he had a date, and I knew he wouldn’t be there for some time, then I could express my feminine side.

One Friday evening I got home from work and Bret was dressed.

“Hey, Kerry, I’m not sure when I’ll be back.”

“Hot date, or are you out with the guys?”

“I might have a chance to hook up tonight, but I’m not sure.”

“I wish you luck.”

He gave me a funny smile before replying. “If it plays out the way I hope it will, I might just have that luck.”

“So when should I expect to see you back?”

“All I can say is don’t wait up for me. I might be late.”

Bret gathered his stuff and left. I waited for a while after he left, just in case he came back for something. I checked to make sure the door was locked securely. After about thirty minutes, I figured I was safe. To be honest, even when I dressed up, I mostly stayed in my room. Once I felt like he was gone, I went to my room to enjoy myself. I started by brushing my hair in a more feminine style.

I took off all my boy clothes and got a pair of lacy pink panties and put them on. I followed that with a lacy pink bra, which I stuffed to make it look like I had boobs. I put on a cute skirt that came almost to my knees and a pullover top. I sat down to do my makeup, with a little base and some blush, then some eye shadow and a pink lipstick almost the color of my panties.

It wasn’t quite what I’d like. I never shaved my body hair, because that might be too obvious - especially around Bret. I didn’t paint my toenails or fingernails because it took too long to dry and too long to remove. I wanted to stay very deep in the closet with no suspicions whatsoever. As it turned out I wasn’t as careful as I should have been.

I paraded around my room, looking at myself in the mirror and feeling very satisfied with my appearance. I am only about 5’5” and 120 pounds and my face is somewhat feminine and my Adam’s apple is not pronounced. When I looked in the mirror, I saw a woman, not a man or even necessarily a man in drag. I put on some music on my computer and danced around to that for several minutes.

After dancing, prancing, and parading, I wanted to get myself off. I had some toys, including a pink plastic dildo which I could attach to the wall. I put it on the wall, and then lubed it up. I pulled up my skirt and pulled down my panties and scooted up easing the dildo into my ass. It felt wonderful going in me and once my ass adjusted to the size I began to fuck myself with the dildo.

I moved my ass back and forth taking the toy deep in me, then nearly out. Before long I was fucking myself in time with the music and the stimulation to my prostate was such that I came in great spurts. I had my skirt pulled out of the way and a towel on the floor to cum onto so I didn’t make a mess. I guess I was panting and moaning pretty good by the time I came.

I was there on the floor on my hands and knees in my girl clothes with the dildo stuck in my ass as I came down from my orgasm, when I heard a sound. Bret was standing there with his phone and had just taken a picture of me in my current state. I was shocked. I didn’t think he was going to be back for hours. I was also shocked and humiliated by how he found me and was frozen in place.

“Well, well, well, Kerry. Isn’t that a pretty picture?”

“What are you doing, Bret?”

“Just admiring the view and getting some pix of it.”

“I thought you were going to be out most of the evening.”

“Obviously. You wouldn’t have let yourself get caught like this if you thought I’d see it.”

“Please, don’t tell anyone. Don’t show anyone the pix. Please.”

“I don’t HAVE to tell anyone.”

“What... what do you mean?”

“I can keep your secret, if you make it worth my while.”

“I don’t have much money, you know that.”

“It isn’t money that I want.”

I was still frozen in place with the dildo in my ass as Bret walked over to me. I could feel my lips trembling and my eyes starting to tear up as he knelt on the floor beside me. He put his hand on my head as he bent over to kiss me. I was shocked and couldn’t even respond for a second, then I kissed him back. I whimpered as he continued to kiss me.

As he pulled back, I could see some of my pink lipstick on his lips from our kissing. His hand which had been on my head moved down my neck and along my back, until he reached my ass. He rubbed my ass cheeks, never quite touching the toy that was still firmly in me. As he caressed my ass, he bent over and kissed me again.

“Kerry, I want to make you feel good, and I want to feel good too.”

“What do you mean?”

He resumed kissing me and stroking my ass for a few minutes, before pulling back. He unzipped his pants and dropped his pants and boxers down. He had a cock that was standing straight out and he looked back at my ass, still impaled on the toy on the wall. He eased me away from the wall, with the dildo coming out of my ass as he did, and he turned me around with my ass towards him.

“Well, Kerry, I’ve got something that can make you feel good and me feel even better.”

He moved close behind me and I could feel the head of his prick at my still gaping bunghole. He eased the head just inside me, then slowly, inch by inch, got his dick in my ass, until I could feel his hips up against mine. I was stunned and couldn’t even react. I wasn’t sure I wanted Bret to fuck me, but his cock felt even better in my ass that the toy had.

He slowly pulled back until only the head of his prick was in me then pushed back in again. I couldn’t help but moan as he slowly fucked my ass, gradually getting a little harder and faster. Before long, he was actually pushing me forward as he penetrated me fully. Bret was in control and he was fucking me as I’d never expected to be fucked.

He couldn’t last that long, and pretty soon, he grabbed my hips, pulled me tight against him and I could feel his dick throb and pulse as he came deep in my ass. He moaned and held me tight as his balls emptied themselves into me. He slumped onto my back in the throes of his orgasm, and my bowels felt awash in his cum.

As he came down from his ecstasy, he straightened up and began to stroke my shoulders and my head. He eased his cock out of my ass, and turned me around and kissed me. He kissed and caressed me, head, shoulders, back, and ass. He more or less sat me down on my towel, and I could feel his cum start to leak out of my ass onto the towel.

“Kerry, baby, that was great. I hope I was as good as your other lovers.”

“I’ve never been with anyone before.”

“You mean, you were a virgin?”

“Except for my toy, yes.”

“No one? No guys, no girls?”

“Not anyone, ever. I wasn’t much interested in girls, and I was afraid to be with a guy.”

“Shit, I’m sorry. I’d have taken more time on foreplay if I’d known you were a virgin.”

“That’s okay. I didn’t really want that, but I did enjoy it.”

Bret stroked my face and leaned forward to kiss me again. He slowly turned us on our sides with him continuing to kiss and stroke me. I was in shock. I’d never have expected Bret to be interested in me sexually. In spite of it all, I wasn’t sure I liked that fact that he’d fucked me. Yes, it felt good, but I was uneasy about it all.

“I kind of suspected you were up to something.”

“What do you mean?”

“You just seemed to be perkier anytime I said I was going to be out for the evening.”

“I didn’t know that was obvious.”

“Then I did some snooping and found your girl clothes.”

“I tried to hide them.”

“It’s a small apartment. Hard to hide anything. So I knew you were dressing up, but only when I was out.”

“So you said you were going to be gone to get me to dress up?”

“When I found you fucking yourself with that thing, it was even better than I expected.”

“I don’t know if -- “

“I’m kind of pan. I like girls, I like girls who think they’re boys, and I like boys who think they’re girls.”

“Still, I think -- “

“Kerry, you’re cute as a girl.”

I kind of sputtered as I replied. “Tha -- thank you.”

“At least for now, I want you to be my girl.”

“Do you mean -?”

“No more hiding. When you’re here, dress as a girl. You’ll be my girl, and I’ll be your boy.”

“That’s what you want?”

“You need to dress as a girl anytime you’re home, and you need to get rid if that body hair.”

“I didn’t think you’d -- “

“You thought wrong. Now get rid of that body hair and fix your makeup. I’ll meet you in the living room.”

“You want me to be a girl for you?”

“You’ll be a girl, and you’ll be my girl. Now scoot.”

Bret kissed me, patted me on the ass. He got up and left my room. I sat there stunned for a moment, unable to process what had happened. So much had occurred so quickly that it was hard to believe. I caught my breath, went in my bathroom, since I had the room with the attached bath, and took off my clothes. I used a razor on my underarms and depilatory on arms and legs.

I had a little chest hair, though not much. I took care of that then carefully shaved around my dick and balls. I didn’t seem to have any back hair, just a little around my neck, so I cleaned that up. I looked in the mirror and what I saw was a flat-chested girl with a prick. I cleaned up a bit and put my clothes all back on, then touched up my makeup.

I still felt uncertain as I walked into the living room. Bret saw me, smiled, got up and walked us over to the sofa and we sat down. Once we were seated, he kissed me and caressed my back and my ass. I squirmed a little bit and he ran his other hand down the side of my face. He spent some time kissing and caressing me.

I hadn’t eaten dinner, and apparently neither had Bret. After a few minutes, the doorbell rang. I was frightened, but Bret stroked me gently and told me to relax and wait right there. I sat very nervously as he answered the door and got a pizza that he’d called in an order for. He paid the person then brought it over and set it down on the coffee table for us. He sat back down beside me put his arm around me and we ate the pizza.

After a while, he drew me to my feet and led me to his bedroom. We sat down on the bed and kissed some more as he ran his hands all over my body. He paused, then unzipped his pants and pulled out his hard cock.

“You’ve never sucked a dick before, have you?”

I shook my head and looked fearfully back and forth between his face and his prick.

“Please, Kerry. For me.”

He gently pushed my head toward his cock. I got down between his legs and looked at it for a few seconds, before looking back up at his face. He just nodded and I looked back at his cock moving slightly forward until my lips were almost to the head of his dick. I closed my eyes and took the end of his prick between my lips.

To be fair, I’d done this with my toy, just never with a real cock on a real guy. I realized he’d washed off his prick, since there was no tang from my ass on it. There was a mild flavor from the pre-cum at the tip. I couldn’t get it all the way in, but took about half of it. I moved my head back and forth, letting my lips and tongue do the work.

I could tell that Bret had leaned back on his elbows, moaning his satisfaction as I gave my attention to his wang. Before too long, he grabbed my head and held it tight as he filled my mouth with his cum. He wasn’t in my throat, but I had to swallow it in order to breathe. After a moment, he let me go and I swallowed the rest.

He pulled me up on the bed beside him and began to kiss me. As we kissed, he kicked his pants and boxers all the way off, then pulled off his shirt. He then pulled off my top and my skirt, leaving me in bra and panties. He stroked my back, then my chest, where my boobs would be if I had any. He could tell even through my bra how I had padded it. He pulled back and smiled at me.

“We need to get you some nice breast forms, baby.”

He resumed kissing and touching me, until he pulled off my panties. He moved me to my hands and knees on the bed as he ranged behind me. I looked back and could see that his cock was nice and hard again.

“Baby, I need you. I need to fuck you.”

“Do it, Bret.”

He fucked me and came in my ass again. Then we fucked, sucked, kissed, and caressed until we fell asleep from exhaustion.

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The next morning I woke up with Bret spooning me and holding me tight. I felt uneasy -- uneasy about being like that with Bret and uneasy about what we’d done the night before. I was trying to figure out if there was any way to get free from his grip and get out of his room without waking him up. I squirmed a bit and Bret woke up. He pulled me tighter and kissed the back of my neck.

“Good morning, baby. I hope you enjoyed last night. I certainly did.”

“I don’t know if -- “

“I know, and I think that was what we both needed.”

“I probably need to -- “

“All in good time, Kerry.”

Bret turned me to him and kissed me some more while stroking my back and my ass. In spite of my continued reservations, I kissed him back. After a few minutes, Bret’s cock was hard, and he set me on my hands and knees and fucked my ass again. My ass was really getting a workout -- far more than ever before. It was tender and I moaned from pain and pleasure as he fucked me.

He didn’t last very long and filled my ass with his cum one again. After he pulled out he kissed me for a while before pulling back and smiling at me.

“I mostly like girls, and boys who look like girls. And you’re a cute girl.”

“Tha... thank you.”

“I told you, I want you to be my girl.”

“That’s what you really want?”

“You need to be my good girl. That means when you’re home, you dress like a girl, you look like a girl, and you act like a girl.”

“All the time?”

“When you go to work, you can dress any way you want.”

“I don’t want them to know -- “

“But I think you like being a girl anyhow.”

“Well, I kind of do.”

“It’s safe being a girl with me. I like seeing you as a girl.”

“I didn’t think -- “

“Of course being my girl means doing what we did last night and this morning.”

“You mean fucking.”

“You object to being fucked as a girl?”

“No, I just -- “

“Because that’s not the impression I got when I saw you fucking your ass with that dildo.”

“I do enjoy that.”

“And we’ll enjoy it together. Now go clean up and put on some nice girl clothes for me.”

Bret kissed me, patted me on the ass and scooted me out. I picked up my clothes as I left and went back to my room. My toy from last night had fallen off the wall, so I picked it up and cleaned it off and put it away. The towel that I’d cum on was still on the floor, so I put it in my dirty clothes. I went in my bathroom, and showered off, then sat thinking for a few minutes.

I knew I was a girl, I wanted to be a girl, and now Bret was not only good with that, he expected me to be his girl. It was just a shock to go from being so deep in the closet to be both openly female with Bret and having him as my lover. I wasn’t sure why he’d settle for a girl with no boobs and no pussy, but he said that’s what he wanted.

I went back into my bedroom and dug out a clean pair of panties. My previous panties had Bret’s cum in them from where it leaked out of me. My bra was wet from sweat from our sex, so I needed a clean bra too. The skirt and top were not so bad, but I still got some clean ones. I didn’t really have a large collection of girl clothes, so I was going to have to get more and wash these pretty quickly.

After dressing, I did my makeup, though I was still uncertain and uncomfortable about it all. I was so used to hiding this side of me that being open about it around Bret bothered me. He made it clear that he wanted me to be this way, but I still was queasy about it. After I was done, I looked in the mirror, and could see the flaws in my appearance, but still basically saw a girl.