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Long Strange Trip

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This story includes cross dressing, non-consensual sex, incest, forced feminization, transgender. If any of that bothers you, please skip the story.


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 Bostancı Anal Escort 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 Bostancı Yaşlı Escort 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 Bostancı Zenci Escort 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?”

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