Long Strange Trip

It’s been a long, strange trip and not one really in my control.

I should introduce myself, I am Stephanie, though I used to be Stephen. I grew up as a boy, though I suppose I was always a little odd. It kind of started in my senior year of high school, shortly after my 18th birthday. I was home alone after school. My parents both worked and my older brother, Carl was off doing God knows what with his friends.

Carl is about 6’ tall and 170 pounds and muscular. He is athletic and works out regularly and it shows. He has chiseled features and a rakish smile that makes the little girls swoon. In contrast, I am about 5’6” and 130 pounds. I had little facial hair, since I was a late bloomer. My hair was medium length. A lot of guys wore their hair longer, but I had people mistaking me for a girl as it was.

I made sure the house was securely locked, then went to my secret stash. I had a skirt, a girl top, a bra, and a couple pair of panties. When I felt sure no one would be around, I’d put them on. It gave me a sexual thrill to dress like that. So I got dressed in my girl clothes, then got a small dildo I had pilfered from my mother.

I got down on my hands and knees, pulled down my panties, stuck the dildo in my ass and began stroking my cock. Just dressing up like a girl got me hard, then putting the dildo in my ass added to that and I was jerking myself off and moaning, when I saw a flash of light. Carl was standing there with two of his friends and had just shot a picture of me.

“Well, looks like the little girl is having herself some fun.”

“Did … you just take a picture of me?”

“Nice one. You – dressed as a girl with a dildo sticking out of your ass. The kids at your school should love seeing that.”

“Please don’t. I can’t have anyone see me like that.”

“What’s it worth to you to keep it hidden?”

“What do you mean? What do you want?”

Carl turned to his friends. “What do you think, guys? Does she suck our dicks or do we fuck her ass, or both?”

“Please don’t make me suck your dicks.”

“But fucking your ass is okay?”

“I don’t - . As long as I don’t have to suck your dicks.”

“Damn, that sounds like consent to me. What do you think?”

The two guys nodded and smiled. Carl walked over to where I was frozen, cowering on the floor. He unzipped his pants and pulled out his cock. He knelt down and pulled my panties the rest of the way off, then pulled the dildo out of my ass. Carl dropped his pants and boxers and ranged behind me. I was scared as shit.

“You promise you won’t tell anyone or let them see the picture?”

“As long as you put out for us, we’ll keep your secret. Right boys?”

Carl’s two friends nodded and mumbled their agreement. I could feel the head of Carl’s prick at my bunghole. I bit my lip and whimpered, as he eased his dick into my ass. I loved the feel of Carl’s cock going in my ass, I just hated the fact that he could make me do that for him. As he got all the way in, I could feel his hips up against my ass.

“Bitch is tight. Feels damned good. I’m gonna enjoy this.”

Carl began to slowly fuck me, pulling nearly out before plunging deep inside me again. As he did, he began to pick up speed, until he was furiously fucking me, almost knocking me over from the force of it. But since he had tight hold in my hips, I didn’t fall over but got fucked longer and harder than I’d ever imagined. Soon he pulled me close and got his cock deep as I felt it throb and pulse as he filled my ass with his cum.

By this time, my head and upper body were on the floor, as Carl held my ass up. As Carl finished cumming in me, he turned to his two friends. “Who’s next?”

Carl’s friend Dirk, already had his pants open. Dirk had a hawkish mien and was a little older than me, but not as old as Carl who was just over a year older than me. Dirk was a bit shorter, and not as muscular as Carl. I tried to catch my breath as Carl pulled his dick out of me and Dirk got behind me. Dirk was rougher than Carl and began to fuck me hard and fast from the start.

Carl’s dick had been bigger around than Dirk’s, but Dirk was a little longer. Carl felt good, but Dirk hurt me as he fucked me hard. Mercifully, Dirk didn’t last as long as Carl and came in my ass very quickly.

“You were right, man. It was nice fucking this bitch.”

Dirk finished cumming in my ass and made way for Rob. Rob was about 6’2” and easily 210 pounds. He was a year older than Carl, but seemed to defer to Carl on everything. Rob’s cock was bigger than either Carl or Dirk, but he eased it into my ass. He stroked my hips as he slowly fucked me and it almost felt loving in comparison.

Rob lasted longer than either Carl or Dirk and when he came, it felt like he turned a firehose on in my ass. After cumming, Rob bent down and kissed the back of my neck. He kissed my neck for a minute or so, before he pulled out.

Needless to say, the three guys didn’t stop with fucking me once. I lost track after a while, but I think they each must have fucked me three times or more. They stopped when it was almost time for my parents to get home. By that time, my ass was sore and I could barely stand. They helped me to my feet and as they did, I could feel a flood of cum running down my legs.

They shuffled me into the bathroom, where I got out of my girl clothes and took a shower on legs that threatened to give way at any moment. I washed all the funk of our fuck session off me, and stood shakily under the water until most of their cum quit leaking out of my ass. I wrapped a towel around me and gathered up my girl clothes.

No one was in the bedroom as I came out, which was a relief. I could hear Carl and my parents talking in another room. I hid my clothes, which were rather a mess after what we’d done, and put on jeans and a tee shirt to come out.

Everything seemed almost unnaturally normal, and from everyone’s actions and reactions, you’d never suspect what had been going on just thirty minutes earlier. I was walking funny and my mother commented on that. Carl quickly replied.

“I tried to get Steph to work out a bit earlier, and you know how little exercise he does. I think he pulled a groin muscle.”

My father made a very dismissive grunt, but my mother came over, and stroked the side of my face. “Poor baby. What can we do to make it feel better?”

“He probably just needs some Advil and to rest a bit. Don’t worry, I’ll get him working out more often so he doesn’t suffer so much from a workout.”

I know I had a puzzled look as I glanced over at Carl. Carl had this smile that told me that today was only the beginning. I must have looked concerned as I gingerly sat down, while mom got me some water and pain reliever. Carl walked over to me and looked down.

“Don’t worry, Steph. We’ll get your ass in shape before too long.”

“Do we have to?”

“You know you enjoyed it.”

I did my homework and we ate dinner, though I couldn’t help remembering what had happened earlier. A bit later, dad was watching television, while mom cleaned up the kitchen. Carl spoke to me in a low voice.

“Tomorrow, after school, we’re going to have another workout session. Wear the same workout clothes you did today.”

“What… are you…?”

“After all, we have to get your ass in shape.”

“But I thought,,,”

“Well, I guess you thought wrong.”

Carl pulled out his phone and brought up pictures of me, first just in girl clothes with my dildo in my ass, then of Dirk fucking me, then of Rob fucking me. My mother saw Carl showing me pictures and spoke up.

“What are you boys looking at?”

“I was showing Steph pix of a girl I know.”

My mother walked over and I was scared shitless that she would see the pix Carl had just shown me. Carl showed my mom his phone, and she looked at it and smiled.

“She’s pretty. Who is she?”

“Just a girl I know.”

Carl angled his phone so I could see that he had a shot of a pretty young woman – not the pix of me. My mother seemed interested in it all.

“Is she someone you’re dating, or going to date?”

“I wish. She has a boyfriend. But she didn’t object to a picture.”

I resumed breathing, and my heart rate got closer to normal. My mother went to watch her shows on the other television. Dad, of course, had dozed off while watching a show. Carl turned back to me, once she was out of earshot.

“You are ours, just as long as we want you.”

“I don’t like that.”

“So you’d prefer being outed as a cross dresser who dildos his ass and lets guys fuck him?”

“I only did that because you made me.”

“And you came on the floor twice while we fucked you.”

“I really don’t have much choice, do I?”

“After school tomorrow, and the next day, and the day after that. As long as we like.”


So nearly every day, after school, I put on my girl clothes and got fucked by Carl, Dirk, and Rob. Honestly, I enjoyed dressing up as a girl. I even enjoyed being fucked, but what I didn’t like was having no say about it. There were days when I didn’t feel much like it or where my ass was sore from what they had previously done. It didn’t matter though, they wanted it, so I had to do it.

It didn’t take long before they got even more demanding. I think Dirk was the first.

“This bitch is too hairy. Look at the hair on her legs.”

“You want me to shave my legs?”

“I’ll bet her underarms are furry too.”

“Yeah, I haven’t shaved there.”

“Shave everything from the neck down.”

“Right now?”

“No, don’t cut into our fucking time, but before tomorrow.”

“But if people notice.”

“So you wear a shirt with sleeves and long pants.”

In one sense, I was happy to be a little more girly, I just would have preferred it to be my choice to do it and when to do it. After they were done fucking me for the day, as I was showering off, I began to shave the hair. The legs were pretty easy to shave, at least the lower legs and in front. Shaving the backs of my upper legs was trickier.

I had to be careful with the underarms, and I really had to be careful shaving around my dick and balls. I only had a few sprigs of hair on my chest, but I got rid of that, and even shaved my arms. It felt a little weird at first, but left my skin feeling so smooth. I took a full set of clothes in the bathroom with me so no one could see where I had shaved.

The next day, Carl, Dirk, and Rob seemed so much happier that I’d shaved. Rob was usually more tender and affectionate and he really began to treat me like a girlfriend. Dirk was kind of a jerk, but that was pretty normal. Carl even seemed a little more tender.

My hair started getting longer and I mentioned that I needed to get a haircut. Carl nixed that very quickly.

“Since you’re our girl, you need more than girl clothes, you need girl hair too.”

Carl knew someone who knew a hairdresser. They trimmed my hair such that I could brush it one way and look girlish, and another way to look more boyish. For a while, I was really concerned at school. I worried that in spite of what they said that one of the guys would share photos of me, or that someone would notice that I’d shaved my body hair. Since I was never in a locker room, that never became a problem.

Of course the changes didn’t end with hair. After a little while, Rob spoke up.

“You know our girl here would look prettier if she used some makeup.”

“Like what?”

“You definitely need some lipstick and eye shadow.”

“That’s all?”

“I don’t know. What do the other girls use?”

“I don’t know, and I can’t exactly just go ask them.”

“So google it, baby.”

So I went out online and found some makeup primers. There were videos showing how to apply it and what to use, most aimed at tween girls, but it served my needs. I was afraid to go to the department stores, so I just went to a drug store and picked up a few things. It felt like the female cashier looked at me funny when I went to check out.

“I’m… getting some items… for my mother.”

“Are you sure you have the right colors? You have items for a couple of different skin tones here.”

“I wasn’t sure what to get.”

“Is her skin tone perhaps close to yours?”

I know I had to have blushed, when she asked. “Pretty close.”

“Let me help you find some better items.”

There weren’t many people in the store, which I made sure of, and there was another cashier, so she went back over to cosmetics and helped me pick out some items that worked a little better. She finished and rang up my purchases and bagged them.

“Well, I hope ‘your mother’ enjoys what you bought.”

“I’m,,, I’m sure she will.”

“Come see me again if you need any more help buying things for ‘your mother’.”

I turned red again, because I just knew that she knew I was buying them for myself. I got antsy at school for several days after, just certain that word would get around that I was buying makeup for myself. Nothing much happened though so I relaxed again.

Rob, in particular got even more affectionate after I began wearing makeup. Rob didn’t just fuck me, he would kiss me and stroke my face and my body. I really felt like Rob liked the girl me, and I was beginning to like him too.

Most of our action took place weekdays after school, but on weekends, Carl would get horny and fuck me after our parents went to sleep. We have a three bedroom house, but the third bedroom is a small attic bedroom, so Carl and I share a room. He waited until my parents had been asleep for a while, and frankly I had even been asleep.

I felt the bed move as he got on my bed. I was still half asleep as he uncovered me. He told me to keep quiet and turned me so I was on hands and knees. He pulled off my jockey shorts and took off his boxers. I was dry and my ass was kind of tight, but he got the head of his cock at my entrance. He tried to ease it in, but it hurt some, and I whimpered.

Carl had to work his prick in an inch at a time. An inch forward, then an inch or two back, Carl slowly got his dick deep inside me. I was concerned because I tended to moan while being fucked, and I was afraid my parents would wake up, hear something and come to investigate. Not only did I not want people in my school to know, but I didn’t want my parents to know I had Carl and his friends fucking me.

I stayed pretty quiet and in spite of my fears, neither of my parents heard or came to see what was happening. On weekdays, Carl fucked me two, three, or four times. Dirk and Rob did likewise. Since it was a weekend, Carl hadn’t fucked me that day. He slowly and sensually fucked my ass, until he came in me. He took a break before fucking me once more before letting me get some sleep.


It became pretty typical for Carl to get his solo weekend fucks after a week of the three guys tag team fucking me. After a few of the weekend fucks, Carl had an idea.

“On the weekends, I want you in bra and panties when I fuck you.”

“You want me to wear a bra and panties to bed?”

“Sure. Why not? Our folks never wake us on weekends, and seldom during the week.”

“Can I take the bra off after you’ve fucked me?”

“If you have to, but I want you to keep the panties on.”

“I mean, I like wearing panties, but – “

“Yeah, I think you do. Maybe you should wear panties all the time, not just when you’re being fucked.”

“But if I do that – “

“Do you go showing your underwear to people at school?”

“No, of course not.”

“Then how would they ever know?”

“If something happened – “

“You just need to make sure nothing happens.”

“What about laundry? I need to sneak to do my girl clothes as it is.”

“Figure it out.”

“And I’m not sure I have enough panties.”

“Well then, I guess you need to buy more.”

Carl was not willing to be dissuaded, so I bought several more pair of panties and wore them in place of my boy underwear all the time. I told my mom that I felt a need to help a little more around the house, so I’d do my own laundry from now on. I tried to do it when neither of my parents could accidently see what I was washing and drying. I almost got caught a few times, but basically succeeded.

In one way, I was happy. I felt more and more like a real girl, between wearing panties, being fucked, and my dress up sessions for the three guys. I still worried deeply about other kids at my school finding out. Carl, Rob, and Dirk kept their word and as long as I let them fuck me, they kept the pix secret. I wore panties to school, but no one seemed the wiser.

Dirk’s father got a promotion that required them to move to another city. Dirk was the roughest of the three, so in one sense I wasn’t unhappy that he was going. Just before he moved, we had a session where every other time I got fucked, it was by Dirk. I worried that once he wasn’t getting fucked anymore that Dirk would release the pix. Carl and Rob threatened him though.

“I know you aren’t going to be getting a piece of her any longer, but Rob and I still have a good thing. If you screw that up, I swear we will track your ass down, and hurt you.”

“I promise, I won’t screw things up for you guys.”

Carl and Rob seemed satisfied with his promise and I was relieved. Dirk came over and squeezed my ass cheeks, then gave me a hard swat to the ass.

“Damn, I’m going to miss fucking this regularly.”

“Well, bro, maybe you can come back for a visit and get some then.”

“Maybe, maybe.”

So now I had only two guys to satisfy, instead of three. I did enjoy being fucked, but three of them was almost too demanding. With two, it was more like having lovers. We continued with Carl and Rob during the week, and Carl late at night on the weekends.

One Tuesday, Rob fucked me a few times, but had to leave early. Carl and I continued, but lost track of time. As usual, I was in skirt, blouse, and bra, with Carl’s dick deep in my ass. It had been a particularly satisfying fuck, and I felt Carl cum in my ass, when the bedroom door opened. My father stood there, and when he saw us, his face was almost purple.

Dad slammed the bedroom door. Carl pulled his cock out of my ass and pulled up his jeans and boxers. I was in shock as my mother opened the door. I cowered on the bed as Carl dashed from the room. My mother looked at me with sorrow and disdain.

“Put your panties on and sit up.”

I scrambled to put my panties on, then realized how I looked.

“I should change.”

“Sit down and shut up.”

I was shaking visibly as a sat down on the bed, still in my skirt and such.

“Your father said you are no longer his son. Whether you even live here depends on whether you do exactly as I say.”

“Yes, ma’am.”

“Do you have any other female attire?”

“A few things.”

“I should have known. Where are they?”

I had two other skirts, blouses, and bras with a lot of pairs of panties. I told her where she could find them all. She gathered them all up and turned to me, still cowering on the bed.

“Come with me.”

“You mean dressed like this?”

“Yes, now do it.”

I got up on shaky legs and followed her out of the bedroom. She went to the spare bedroom in the attic, with me following. When she got there, she threw all my girl clothes on the bed.

“You can put your clothes away.”

“What do you mean?”

“This is now your room. We won’t have a girl and a boy sharing a bedroom.”

“But I’m not – “

“You’re no longer my son. You’re now my daughter.”

“But, I’m a boy.”

“Not by what you’re wearing, and not by your actions.”

“What about the rest of my clothes?”

“We’ll have to buy you more skirts, tops, and bras.”

“But my boy clothes?”

“If you’re a girl, you’ll wear girl clothes, not boy clothes.”

“But I still have a month of school. What do I wear?”

“Since you’re a girl, you’ll wear girl clothes to school.”

“Please don’t make me do that.”

“You made a choice to dress like a girl and get fucked like a girl. Now everyone can see the girl you are.”

“Can’t we do something else?”

“You can take your stuff, leave here, and not come back. Then you can dress anyway you want.”

My mother was adamant. She had me take a shower and change into clean clothes, then said we were going to buy some additional clothes.

“Can I change first?”

“You changed into clean clothes.”

“I mean into boy clothes.”

“You have no boy clothes. They’ve already been given to charity.”

“So I have to go shopping like this?”

“Put on some makeup and brush your hair decently.”

I did that and came back. My mother looked at me and seemed more satisfied.

“So let’s go clothes shopping.”

My mother led me downstairs, though I hated the fact that I had to go out dressed in my girl clothes. I really didn’t want anyone I knew to see me in them, even if I did like wearing them. We got to the living room, where my father sat glowering. Carl sat there looking very chastened. My father saw me and looked even angrier.

“You disgust me.”

“I’m sorry. What can I do - ?”

“I thought you were my son. I guess I was wrong.”

“I want to be your son.”

“You gave up that right when you dressed like a girl and let guys fuck your ass.”

“So I can’t – “

“You can try to be a good girl.”

“I have to be a girl?”

“That was what you chose.”

“I can’t unchoose?”

“Not living in this household.”

“I only have a month left of school. Can’t I be a boy for that?”

“No you can’t. You’re going to be punished for what you did, and your punishment is for everyone you know to see you as the girl you seem to be.”

“I could get my boy clothes and leave.”

“You have no boy clothes. They were given to charity. You can leave, but as the girl you are.”

“And if I stay?”

“You stay as a girl – and you do not have sex with your brother – ever again.”

“I only did that – “

“Don’t fucking lie to me. You did it because you wanted to.”

“I’m sorry.”

“At least I understand why you never dated any girls.”

“I never found any who’d go out with me.”

“I wonder why. And if you date any boys, you’d better not fuck them here.”

“Yes, sir.”

My mother took me out shopping and bought me some additional skirts and tops, along with a dress, some bras and some flats. I felt humiliated walking around the store dressed as a girl. Luckily, I didn’t see anyone I knew, but I just felt like people were looking at me and they knew. There wasn’t much I could do though.

“What about getting me some jeans and tees?”

“Since you’re going to be a girl, you’ll dress 100% girl.”

“But they know me as a boy at school.”

“I’ll go in with you tomorrow and we’ll address that.”

Then my mother took me to a nail salon, where she had them put bright pink polish on my fingernails and toenails. She made sure that I had flats that showed my toenails. I had never worn nail polish before and felt strange at how it made me so out there. She clearly was going to make me as feminine as she possibly could.


The next day, I was dressed in skirt, blouse, bra, and panties, as my mother drove me to school. I wanted just to skip the rest of the school year, but my mother and father wouldn’t let me.

“You live here, you’re going to school, period.”

She walked back to the office with me, and I could see other kids looking funny at me. Some laughed out loud. She sat down with me in the principal’s office, along with the dean of boys and dean of girls.

“The student who you knew as Stephen is now Stephanie. She is transitioning to female and will be dressing as such from now on.”

“We are going to have an issue with the locker rooms.”

“I’ve completed my phys ed credits. I won’t be in any locker room.”

“I don’t want you in the girl’s bathrooms, or the boy’s for that matter.”

“There’s a couple of single person unisex bathrooms.”

“Those are primarily for certain handicapped persons.”

“Can I please use those?”

“I suppose that is the best alternative.”

“Why the hell did you have to do this now?”

“I didn’t have much of a choice.”

“You made your choice, so you’ll live with the consequences. Don’t come crying to us about how the other students treat you.”

I was never exactly a popular person before that, but I was not decidedly unpopular. Most students now avoided me, but the ones who didn’t were a real problem. I was called a faggot and a tranny. I had guys saying I should suck their dicks or let them fuck me. I had some pull up my skirt as I walked down the halls. One even pulled up my skirt and stuck his hand in my panties.

The teachers kept it from getting too bad during the day. Once school was over and I left the school grounds I had boys who beat me up. One time a couple of guys held me down as others pulled my panties off. A couple of guys tried to take my skirt off me. Luckily there were adults who intervened before things got too bad.


When my mother said she had a doctor’s appointment for me right after school one day, I was ecstatic. At least for one day, I’d escape the harassment after school.

“Stephanie here is transitioning to female. What can you do to help ease her transition?”

“I’m guessing you want HRT?”


“We’ll start her with a shot and give her weekly shots after that.”

I had no idea what they were talking about, but they gave me a shot. I figured that if I was in a doctor’s office I was at least safe from the harassment. I felt a little odd, after the first shot, which continued with subsequent shots. Little did I know what the shots were doing to me.

I no longer had guys fucking me after school each day, and Carl was not allowed to fuck me at all. Dirk had moved out of town, but Rob was around and was interested in dating Stephanie. I accepted a date from Rob, which turned out to have side benefits. Rob was big enough so no one was going to give him trouble about dating me. Beyond that, Rob had friends at my school. He told them to make sure no one laid a hand on me. I still had kids calling me names and making rude suggestions, but no one touched me after that.

Friday evening, Rob picked me up for a date. He had a job and a car and a place of his own. He didn’t make a lot of money, so we just had fast food for dinner and went to see a movie, before going back to his place. It was just a little studio apartment, hardly lavish, but it gave us some privacy and gave me an escape from my parents.

Rob was sweet and he got me something to drink and we sat down on his small sofa. He stroked my face and kissed me. I kissed him back and we spent quite a while kissing as Rob stroked my body. Eventually we moved over to his bed, where he took off my skirt and top. He pulled off my panties and tenderly fucked my ass. He repeated that a couple more times before driving me home.

I began to date Rob regularly and we both seemed to care for each other. After a couple of dates, we were sitting on his sofa after we’d kissed and stroked each other for a while. Rob stopped and pulled back slightly then dropped his eyes slightly.

“You said before that you didn’t want to suck dicks.”

I took a deep breath before replying. “When I was being gang banged by three guys, I didn’t want to suck your dicks too.”

“And now?”

“What I do for one person I care about may be different.”

With that, I slid off the sofa and moved right in front of Rob on the floor. I looked up at him, and he looked down at me, then I reached up and slowly unzipped his pants. His legs were already somewhat spread, but he spread them even wider and slid his hips forward on the sofa. I undid his belt and the button on his pants and pulled his cock out.

I wrapped my hand around the base of his dick and leaned forward with my lips loosely closed. I let the head of his prick spread my lips, almost like they would a pussy, and eased his rod into my mouth. I kept my lips firmly around his cock as I bobbed my head back and forth, fucking my mouth with his dick. Rob leaned back and moaned even as he stroked my head with one hand.

I took it slow and easy as he began to move his hips slightly back and forth. I took as much of his prick in my mouth as I could without choking. I lovingly worshiped his cock until he held my head tight and came with a gush in my mouth. He held me firm as he filled my mouth with his cum. I swallowed it several times and he finally released me as the last few spurts of cum trickled out.

I worked his softening prick in and out of my mouth, sucking all the cum off him. Finally I had only the head still in my mouth as I let my lips close as I pulled the tip out. Then I licked the glans and particularly the tip and the slit for the last few drops of cum. I finished and climbed back on the sofa with Rob who began kissing me, no doubt tasting his own cum in my mouth.

After we kissed for a while he got up, picked me up and carried me over to the bed, where he tenderly undressed me and fucked me. After he came in my ass, he thanked me for sucking him off.

“For you, I’m happy to do that. I just ask that after you’ve fucked my ass, that you wash your dick off before I suck it.”

“For you, I’ll do that, baby.”


I finally made it through the horror show that was the last month of school. I was finally going to graduate and be out of that place. I didn’t want to go to my graduation, but of course my parents insisted. I felt like their life was not complete unless they could humiliate me a little further. In cap and gown, it was hard to see my girl clothes, but my mother made sure my hair and makeup told the story.

As though to add to the whole load of humiliation, when they called my name for me to come forward, they called for Stephen Miller rather than Stephanie, which made it clear to even more people that I was born male but living as a female. As I walked up to get my mock diploma, I could hear loud laughter, along with hoots and a few people even shouting ‘faggot’ or ‘tranny’ at me.

Of course there had been more comments both before and after I was on stage. I wanted to cry, but had no intention of letting them make me cry. Rob was there also, and hugged me once it was all over. My parents seemed somewhat conflicted about Rob, largely because he was a positive in my new life that they had imposed on me.

My parents insisted that I needed to get a job, now that I’d graduated. They got me an ancient Honda, cheap, but still very reliable for transportation and told me besides working, they felt I should go to a community college nearby. I had a few months before the fall term started so I began looking for work, mostly as a sales clerk.

I had my driver’s license redone with my picture as I now looked, but it still had my name as Stephen, and gender as male, as did my social security card. My parents said that I could pay for my name change from what I earned, and just live with that until I could afford that. A couple places looked at me and looked at the name and gender on my ID, and sent me on my way.

After many tries, I finally found someone who would hire me. My boss seemed mostly okay with it all, but some of my co-workers were damned unhappy about it. This place had no unisex bathrooms and a few people called me a pervert and threatened me if I went into the women’s restroom. I tried to drink as little as possible during the day, and use the bathroom where I went to lunch.

Occasionally, I even got some grief at lunch, but at least there they were less likely to know my birth gender and object to me. I worked in a small department store and they put me in women’s wear. I guess in one sense that was fitting, though I got some nasty reactions if women asked for help in the changing rooms.

I tried to be friendly and helpful in spite of the grief I got from some co-workers. Eventually, a couple of the women grew to like me. They helped run interference with some of the nastier people.


As the summer progressed, the hormone treatments began to take some effect. I hadn’t really known quite what to expect, so when my breasts became more sensitive and started to grow, it was kind of a shock. My waist seemed to narrow and my hips grow as fat distribution changed. I never had a lot of chest or facial hair, but lost some and got no more.

Rob loved the changes and as I started to get boobs, he enjoyed playing with them, though they were very small at first, and never really got much beyond an a-cup. Carl seemed to get jealous of Rob and the fact that Rob could still fuck me even though Carl was forbidden. Carl kind of hinted that we should find some way for him to fuck me, but I told him I wasn’t going to get thrown out over him.

I suppose I could have moved in with Rob, though he never brought that up. We dated and fucked, but he wasn’t ready for me to be a live-in lover, at least not as I was. With what I was being paid, I couldn’t afford my own place, so I was stuck with living by what my parents wanted until I could afford something better.

It occurred to me that if I moved out, I could go back to living as a boy, but with the effects of the hormone treatments that seemed unlikely and I wasn’t sure that was what I wanted anyhow. In most ways, I was far happier as a girl, even if I did get a lot of shit over having been born as a boy. Rob and I began to talk about it all when we were together.

“Have you thought about getting surgery to get a pussy?”

“It’s expensive, and I have to live as a female for a year before they’ll do it.”

“That stinks. If you were all girl, I’d have you move in with me.”

“I wish I were, for both of us. My parents still seem to hate me.”

“I guess we’ll keep going like this for a while then.”


Community college started in the fall, and while some of the other students knew me, many others didn’t. I’d gotten the money to do a name change and gotten my driver’s license changed to show me as female, so that reduced some of the friction. But along the way, Rob began to back off. He started to date another girl, someone who was born as a girl.

Before long, Rob and I seemed to be history and he was seen all over town with his new girlfriend. There were a few guys and even a few girls who seemed interested in me, but I knew that most of them would not like what I was. A couple of times, people who had been interested, got tipped off by folks who knew me. Those people invariably began avoiding me afterwards.

I mostly became the lonely girl, though I had a few girls who were willing to hang with me, though they had no interest in anything physical. After a while, I almost wished I could go back to having Carl fuck me occasionally, but I wasn’t going to risk having my parents throw us both out over it. So I worked, I went to school, I hung with my few friends, and got very comfortable with being a girl.

As my school year ended, my mother came to me and told me I ought to go ahead with bottom surgery, and said she would help underwrite the cost. I had some vacation time saved up from my job, so I took time off and went ahead with it. At that point, I wasn’t sure it would matter to anyone but me and my mother, but I was ready.

It also was nice because I really did have a choice this time. My mother encouraged it, but the decision was mine to make. I doubt that I’d have made that if it weren’t for what I’d already been through. It had kind of reached the point where the surgery just confirmed things. Even if I moved out, I was never going to even try to live as a guy any longer.

I was comfortable as a woman and that seemed to be who I really was. I still got grief from co-workers and some other students, but more and more seemed to accept me as a woman. I still had to watch my step, as a few of the haters looked like they could become violent. One disappointment was when I ran into Rob while out somewhere.

Rob had been the most supportive in the early days of this journey. It was disappointing to find that he had now flipped and was hostile and dismissive. I was with a few friends when he saw me and came over. It was about a week before my surgery was scheduled. A handful of us were celebrating the end of another work week, as well as congratulating me on my upcoming operation.

“I don’t know if you know it, but Stephanie here is actually a boy who dresses like a girl and lets guys fuck him in the ass.”

“Which you did more than anyone else and that didn’t seem to bother you then.”

“I didn’t know any better then.”

“You fucked me in the ass repeatedly, over a few months and couldn’t tell I had boy parts?”

“I thought that’s what you wanted.”

“So you and your friends threatened to send photos of me dressed as a girl and being fucked, in order to get me to continue to let you fuck me.”

“You sure as hell seemed to enjoy it.”

“Like you didn’t.”

“I moved on and found something better – a real girl.”

“I’m sorry for her.”

Rob turned and stormed off. I wanted to cry, but didn’t want to give him the satisfaction and didn’t want my friends to know he made me cry.


I took two weeks vacation and had my surgery. My mother was there to support me and comfort me. I wish I could say I’d gotten any support from Carl or my father, but I didn’t. After two weeks, I returned to work, but still wasn’t moving as well as I might. Standing on my feet during a sales shift was tough, but I could sit at a cash register part of the time and that helped.

By the time school started in the fall, I seemed almost back to normal. I still wasn’t cleared for vaginal sex, but since I wasn’t seeing anyone, that really didn’t matter. I started my classes and found fewer of the people who knew Stephen. Basically people just seemed to know and accept me as Stephanie. I even had a few guys who seemed interested in me, though I tried to discourage that.

Some guys get really hostile if they find that the girl they are with is trans, even if she has had the surgery. I didn’t want to chance that. Now there are some guys who fetishize trans women, but I didn’t really want anything to do with them either. I had a few girlfriends who I hung with but tried to avoid guys as much as possible.

In a way, that was sad. I felt like a girl, and had girl parts, including a pussy and boobs that were now roughly a b-cup. I wanted to have a boyfriend – someone to date me, kiss me, and even fuck me. Now that I had a pussy, I wanted to be fucked there, though I wouldn’t mind the occasional ass fuck. I was afraid though – afraid of having a guy get interested then being repelled when he found I was trans.

There was one guy, named Tom, who I had not known before, who talked to me a few times after a class we shared. Tom was hardly an Adonis, but seemed kind of quiet and even shy. Tom was about 5’9” with an average face and average body – certainly not ripped. He wore glasses and was somewhat studious. After a while, he suggested that we study together.

I certainly was good with studying, but only in public places and not with any physical affection. We began to spend a little time together like that when Tom finally worked up the nerve and asked me for a date. I’d been worried about that, mostly because I was afraid of his reactions.

“I’m not sure it’s wise for us to date.”

“Why? Because we’re taking classes together?”

Now was what I’d feared. “No, because I’m trans.”

“What do you mean?”

“I was assigned male at birth. I lived most of my life as a boy. There are still people in town who know me as a boy.”

“But you look like a girl.”

“I am a girl.”

“But are you a girl there?”

Obviously, he wanted to know what I had between my legs. I still wasn’t quite to the point where I’d been cleared for vaginal sex, though I’d been dilating it very regularly. Still I felt insecure and felt his question was intrusive.

“At this point, it doesn’t really matter what I am there. If we get to a point where it does matter, you’ll know.”

“So I would be going out with you not knowing if you’re a girl or a boy?”

“I’m a girl, regardless of what I have there. If you have to know that before going out with me, then you shouldn’t date me.”

“I like you, and want to go out with you.”

“Even if you don’t know that?”

Tom looked at me, bit his lip and looked at his shoes. He shook his head very slightly, then looked back at me again.

“You’ll let me know before we get – intimate?”

“I will.”

“I … I think I still want to go out with you.”

“If you really mean it, then give me a kiss.”

“A kiss?”

“On the lips.”

Tom looked very uncertain. He seemed nervous, then he took a deep breath.

“I’ve never kissed a girl before.”

“Then it’s time to start.”

Tom’s eyes got very wide, as he leaned forward. His lips parted slightly, then he closed his eyes and touched his lips to mine. He didn’t do much more than touch his lips to mine, but I leaned into him and kissed him. He began to kiss me back, and after about thirty seconds, I pulled back. Tom bit his lip again and looked at me.

“I enjoyed that.”

“Assuming you still want to go out, at the end of our date, you can have a better kiss.”

“You promise?”

“Just as long as you treat me right.”


I still felt nervous, even knowing that Tom knew I was trans. I didn’t want him to pick me up at my house, so I met him at a restaurant for dinner. We had a nice meal and then went to see a movie next door to the restaurant. In the theatre, Tom put his arm around me, which made us both feel a little funny. I had not really been close to anyone since Rob broke up with me months earlier.

After the movie, Tom walked me to my car, and we talked for a long time. I realized that Tom was quite shy and nerdy.

“I have to admit, I’ve never really had a girlfriend before.”

“But you’ve been on dates with other girls?”

“You’re the first.”

“So were you never intimate with any girls before?”

“None, at all.”

“You should know, I’m no virgin. I’ve been with boys.”

“You mean - . How?”

“I’m not going to give you any details, but if you want a girl who’s as innocent as you are – that’s not me.”

“You’re still not going to tell me – “

“Before we reach a point where it would matter, you’ll know.”

“I don’t know if I feel comfortable being intimate with someone who is still a boy there.”

“I understand.”

“I’m not sure - . How would we - ?”

I touched a finger to his lips and he stopped talking.

“I think it’s time for you to give me a real kiss, and for me to go home.”

Tom still looked uncertain as he moved toward me. I grabbed him and pulled him tight to me and lifted my head for him to kiss me. He very tentatively put his arms around me as he kissed me. He wasn’t the greatest kisser, but he was sweet. He had one hand loosely touching my waist. I reached down and moved his hand down onto my ass.

Tom made a funny sound as we kissed, but he didn’t stop kissing me. His hand rested loosely on my ass, so I reached down and pressed it more firmly into my ass. He kept kissing me, but through his clothes, I could feel his cock getting hard. He tried to turn so it was not pressed against me, but I held him tight so he couldn’t.

I loved that fact that kissing me and touching my ass was getting him turned on and hard. I had gotten the okay for vaginal sex from my doctor, but for some reason wanted to take it slow with Tom. We kissed for a little longer, before I pulled back.

“I need to be getting home, but thank you. I enjoyed going out with you and I’m glad you asked me.”

“Maybe we can do this again soon.”

“I hope so.”

I gave him a quick kiss, and got in my car. I was almost floating on air, but was brought back to earth by the thought that as we went along Tom might start to feel antsy about dating a trans woman. Not only that, but some of the other folks at school know I’m trans and might give him some crap about it. Would he still feel the same way if people teased or harassed him over dating me?


Tom and I began going out every weekend, in addition to studying together. At first I just let him kiss me and touch my ass. After a while, I let him touch my boobs too. I made it clear he was not to touch me between the legs. I wanted to get there and even beyond but after everything I’d been through previously, I wanted to take it slow with him.

“Stephanie, I almost don’t care what you have between your legs now. But if we get serious, I hope you’re willing to be a girl there too.”

“I already am a girl there.”

“I’m glad, even though I love you regardless.”

“I told you I’m not a virgin, but I am a virgin there.”

“But, how?”

“Anal and oral.”

“I didn’t think about how – “

“You’ve never been intimate with anyone?”

“No. Does that bother you?”

“It doesn’t, and I’m not sure I’m ready to go all the way, but I can make you feel good, If you’d like.”


We were in a basement room at his parent’s house, and his folks were out for the evening. I slid off the sofa and got on my knees on the floor in front of Tom. He looked uncertain, even though I could see that his dick was hard in his pants. I gently spread his legs, moved forward and unzipped his pants. I reached in and pulled out his cock which looked like it was trying to tear its way out.

“Are you sure about this?”

I leaned forward and took the head of his prick in my mouth. Tom moaned and slumped back in the sofa. I slowly took it in my mouth as deeply as I could. I’d never learned to deep throat, but Tom seemed to enjoy whatever I was able to do. I used my lips and tongue, getting it most of the way in, then slowly back out until I had only the head still between my lips.

I did my damnedest to make it slow, sensual, and loving as my mouth made love to his rod. It took almost no time before Tom erupted in my mouth. He had several spurts over about twenty or thirty seconds, and I wanted to get every bit of it. I kept working him in and out of my mouth as he unloaded his cum in me. As he stopped spurting and started to soften, I eased him out, cleaning him off as I went.

I tucked him back in his pants and zipped him back up. Tom almost looked like he was passed out on the sofa. I climbed back up and sat beside him on the sofa and he started to rouse slightly. I leaned over him and kissed him, giving him a taste of his own cum. He was almost frantic in his kisses for a few minutes, before he settled back down.

“That was wonderful, Stephanie. I just wish I could make you feel as good as you made me feel.”

“We’ll get there. We’re just not there quite yet.”

I heard his parents come back in the house, so I hopped up and smoothed my skirt and blouse. I ducked in the little powder room in the basement to check my makeup, which was a little askew after what I’d done. I touched that up and came out to find Tom’s dad had come down to check on us. Tom was standing talking to his father.

When Tom’s father turned to look at me, Tom tried to discretely adjust his dick in his pants.

“I hope I didn’t interrupt anything.” Tom’s father said with a look that said he knew damned well he had interrupted something.

I smiled at him before replying. “No, it was getting to be time for me to go home anyhow.”

Tom rushed over to me. “I’ll walk you out to your car.”

We went out to my car, and I felt certain one or more of his parents were watching us. Tom hugged me and gave me a long kiss.

“That was great, but I want so much more.”

“We’ll get there – soon.”


Several days later at school, I saw Tom and he appeared very upset.

“My father did some asking around and found out that you used to be a boy.”

“And he didn’t like that.”

“He told me to quit seeing you.”

“I’m sorry.”

“I told him I wouldn’t.”

“How did he react to that?”

“He turned purple and I thought he was going to hit me.”

“He didn’t, I hope.”

“No, but he threatened to kick me out of the house.”

“What will you do?”

“My mother put her foot down and said he wasn’t going to do that.”

“Thank God.”

“But he told me I’m never to bring you in the house again.”

“Not too surprising, I guess.”

“My mother is not angry like my dad, but she wants to talk with you.”

“You and I together?”

“You and her alone.”

Something told me this would not turn out good, but I agreed to meet with his mother. We set up a meeting where she and I could talk privately and not be overheard. I was almost afraid that I’d never be seen or heard from again.

“So you are ‘Stephanie’?”

“I am.”

“So why did you latch onto my son?”

“Tom asked me out. I wasn’t looking for any guy.”

“And just how ‘close’ have the two of you gotten?”

“Not that close, physically.”

“If you did, are you even capable of being close the way a man and woman would?”

“There’s more than one way that a man and woman can be close, but we could be close in all the ways a man and woman normally could.”

“And where do you expect the relationship with Tom to go?”

“I don’t know where he wants it to go.”

“Where do you want it to go?”

“I’m almost afraid to have any expectations.”

“Most normal guys would have no interest in the likes of you.”

“Don’t I know that? And some just want the kinky pleasure of saying they fucked a trans woman.”

“My son isn’t like that.”

“Which is why I agreed to go out with him.”

“Do you expect him to marry you?”

“We aren’t anywhere even close to considering that.”

“But you want to get married?”

“I’d like to get married to a man, if I can find one who truly loves me.”

“The word is that you slept with a couple of other guys.”

“I’m not proud of that, and I told Tom I’m no virgin.”

“If you do get married, you could never have a baby.”

“I have some female equipment but not the equipment for that.”

“My husband and I want grandchildren.”

“There’s always adoption.”

“Tom seems to be in love with you.”

“There are lots of romances that never go anywhere.”

“What do you want with Tom?”

“Just a normal relationship between a man and a woman.”

“Some people wouldn’t even consider you a woman.”

“Those are people that I’d never want a relationship with.”

“What if I told you to stay away from my son?”

“I didn’t pursue him, he pursued me. You’ll have to convince him to stay away from me.”

“I honestly expected something different from you, Stephanie.”

“I’m sure I’m not what you want for a daughter-in-law, but I don’t know that it will ever get that far.”

“And if Tom dumps you tomorrow?”

“It’ll hurt, but I’ll go on. I’ve already lived through hurt and abuse that you could never imagine.”

“I’m not sure you’re the right person for Tom, but he has to make his own decisions.”

“If he decides I’m what he wants, and if he’s what I want, I hope you can accept that.”


Tom was already working part time, while going to school. He managed to get full time hours and given the hostility of his father began looking for a place of his own. I was still working full time, so between it all, we didn’t have as much time for dating as we’d like. My brother Carl had moved away from home, and when my parents took a vacation, I brought Tom back to my house.

We spent some time making out on the sofa, then I took Tom to my bedroom. I still was in the little attic bedroom. I guess I could have moved into the bedroom that Carl vacated, but that still held some memories that I wanted to put behind me. When we got to my bedroom, Tom was afraid to think that it could mean something more.

We sat on the bed and kissed and I asked Tom to unbutton my blouse. His hands were shaking as he did, and he fumbled with a couple of the buttons before he finished. I shrugged off my blouse, and Tom sat there with a look of nervous anticipation on his face. I took one of his hands and put it on a bra cup. He hesitated before beginning to stroke my boob through my bra.

We kissed as he caressed my breasts through my bra, before I asked him to unhook my bra. I had to turn around so he could see the back of my bra, since he couldn’t unhook it without looking. I almost felt shy as I turned back around and let my bra fall off me. Tom saw my boobs and looked amazed. I put his hands on my titties and his eyes got very big.

He began to fondle my breasts as I lay back on the bed. He stroked them for a while, before I pulled his head down to one of them. He took the nipples in his mouth and began to suck on it, as though he could get milk out of my boob. I loved it. Rob was the only other guy to touch my boobs and they were smaller and less sensitive then.

Tom loved my titties and gave them the attention they had never had before. As he played with them, I could feel a heat rising through my body, and I almost felt like I was on fire, before waves of pleasure began to roll over my body. I’d never had a female orgasm before and it was like nothing else I’d ever felt. I sure wanted to feel it some more though.

I took off Tom’s shirt and pants, and had him take off my skirt. We got completely on the bed and kissed more when I took his hand and put it down between my legs. He fondled my pussy through my panties as we continued to kiss. After a while, I lifted my hips and told him to pull my panties off. As he got them off, I spread my legs and for a few seconds, Tom just stared at my pussy.

“Lick it please. You’re the first guy to get my pussy.”

I had shaved the hair from between my legs, so I was completely bare down there. Tom leaned over and did a tentative lick up my slit.

“More, please, baby.”

Tom dove in and licked and kissed my pussy like there was no tomorrow. He licked me to my second orgasm before I made him take off his boxers and move back up my body. I know I don’t have quite the natural lubrication of a normal pussy, so I had some lube and I lubed up his cock and had him range over me. I kissed him and then grabbed his prick and eased it into the entrance of my cunt.

I had been dilating, so I had things in there, but this was the first real dick I had there. Dilation felt good, but it was nothing compared to the feel of Tom’s cock in my pussy. I wrapped my legs around him, as Tom began to slowly and sweetly fuck my cunt. More than a year ago, I had guys in my ass, and that felt good, but this put that to shame.

I began to fuck Tom back as he fucked me and before long he was fucking me hard and fast. In one sense, I was sorry I had waited, but I needed to make sure that it meant something to Tom before we did this. I was panting and moaning as Tom drove his prick deep in my pussy. I looked at his face and it was like he was on another world and his being was centered on his dick in my cunt.

“Oh God, baby, I’m cumming.”

“Do it. Fill me up with that cum. I need you.”

Tom stiffened and drove his cock deep in my pussy as I felt it throb and pulse inside me. As he finished, he almost collapsed on me. As he regained his senses, we kissed for a long time before he rolled off me. We fucked several more times before falling asleep together in my bed. For the rest of my parents’ vacation, we spent the nights together in my bed fucking in every way we could.


Tom and I have a place together now. Tom’s mother and my mother seem to have reconciled themselves to the relationship. Tom’s father still hates me, and my father seems largely indifferent. Will this be forever? I don’t know, but for now it seems to be everything either of us could want. I am truly Stephanie, and for now, my long, strange trip has brought me someplace good.

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