I feminized and fucked him [f/m] | 2016

When I was in my Freshman year of college, I started having sexual fantasies where I dominated submissive men. I had "traditional" sex throughout high school, but was always bored with it. I needed mental aspects like humiliation and domination to be brought in for sex to be truly worthwhile. I get off on breaking social taboos.

In one of my philosophy classes, I met an androgynous guy named Justin who I got along with really well. He was on the skinny side with long hair and olive skin. We began spending our breaks between classes with each other, and within a few weeks, we were hanging out outside of class. In what was becoming our nightly ritual, I called him on the phone just to talk about nothing in particular. I wanted to find clues of his sexual personality (e.g. is he submissive? is he open to humiliation?) without actually asking about his sexual tastes. So I started by talking to him about his long hair and how pretty it was. I used the word "pretty" intentionally to see how he would respond. A typical guy would become defiant at the word pretty, but he genuinely said thanks. This made me curious, so I took it a step further by saying in a lighthearted tone, "you'd make a pretty girl!" Again, he didn't get offended. Interestingly, he got a little quiet and hesitantly said, "well, who's to say I haven't made a pretty girl before?" Although there was nothing overtly sexual in our conversation, I became slightly turned on as I noticed the dominant/submissive undertones of our conversation.

I began to dip deeper and asked him if I could dress him up sometime. He nervously complied and told me his close girl friend in high school used to dress him up as a girl frequently. Excited, I began going off, "I could do your make-up... and style your hair! You could wear my dresses and heels too!" He told me he would really like that and I knew I had found a submissive guy who would be open to interesting sex. A flood of thoughts entered my mind, and before I knew it, I told him, "I could bend you over, lift up your skirt, and fuck you with a strap on." He let out a small moan and told me how much he'd like that, so I continued to describe what I wanted to do to him. I told him how I was soaking wet and he replied by saying, "Well, I'm really hard too." I don't think he understood the situation, as men get hard all the time, but rarely did I get this turned on. I was fingering myself to orgasm as we talked about plans to meet up the following night and live out these fantasies. I continued to rub myself throughout the night, thinking of dominating him.

The next night, he came over really late. I think he was nervous about anyone in town finding out about his secret crossdressing hobby. I invited him down to my basement (I still lived at home when this story happened) and told him I had some clothes waiting for him. He stripped down naked and I handed him a pair of black panties alongside a lace body stocking. He put them on and sat down next to me on the floor as I began styling his hair and applying his make up. He looked so nervous, but was completely submissive to my every move. I was controlling him in every way, and not only emotionally: I was turning him into a defenseless, frail woman clad in make up and lingerie. He was now stuck in my "dungeon", as he couldn't simply leave in his current feminized state. I grew more and more confident as I realized his vulnerability.

After completing his transformation, I stood up and looked down on a beautiful, androgynous boy who could pass as a girl in most night clubs. I jokingly told him to find us a cute boy for the night, in which he nervously smiled. I extended my hand to him and led him over to the couch. He compliantly followed as I lay him down. I lifted my skirt and told him, "You wanna lick my pussy like a good girl, don't you?" He nodded his head as I sat down on his face, noticing his hard-on through his panties. I refused to touch it, as I wanted the pleasure to be all mine. Plus, I figured he liked the gender role switch: the girl gets to cum while the guy frustratingly remains horny with no outlet.

After he ate me out, I turned him onto his stomach and placed his arms behind his back. I took out my handcuffs and tightened them around his skinny, little wrists. After that, I strapped by ball gag into his mouth so he couldn't make a sound. I left him on the couch defenseless, and told him I'd be right back. I intentionally left the room for about ten minutes, letting him feel completely humiliated. There he was, handcuffed and dressed in lingerie, wriggling on my couch. I had all the power: I could take pictures of him, torment him, or make him concede to any of my demands. Of course, I wasn't going to do any of that, I was simply going to grab my strap-on vibrator from my room. When I returned, I showed him the vibrator and began gliding it across his face and lips. I told him it was going inside him. I noticed a small wet spot forming in the front of his undies.

I helped him get off the couch and bent him over the armrest. The taboo reversal of power - a woman dominating a man - continued to make me hot. With no notification, I lifted up my skirt, strapped on the vibrator and entered him. I began to pound him as my wide hips slammed against his little ass. Even with a ball gag in his mouth, his screams were loud. I entered him deeply and began pushing my clit against his tailbone, bringing me close to orgasm. I felt such a rush of power, getting to experience how a man feels when he fucks a woman. Due to our moans and my hips nailing his ass, I didn't realize how loud we had become. Soon enough, I heard my basement door open and began to scramble as I realized I had only a few seconds before someone came down and saw everything. Immediately, I ripped off the strap-on and hid it. There was nothing I could do about Justin, so I let him lay there, bent over the couch. I turned around to see my mom at the bottom of the stairs. Surprisingly, she wasn't the least bit upset. She just told me to keep the noise down before taking a bemused look at him. I apologized and told her we'd stop.

When the door closed, Justin was laying there with a look of shame on his face. I laughed at his nervousness and told him it was alright. What's more, I already came so I was taken care of. I took off his handcuffs and ball gag and laid down next to him on the couch. I held him in my arms and comforted him about being seen by my mom until he fell asleep.

The next day, I told Justin about how my mother brought up what she had seen. He was embarrassed but glad she wasn't upset. The best part was, I now had power over him. At school, I could get him to do anything I wanted, lest I tell his friends about our little escapades. When he disagreed with me over something in class during group discussions, I'd give him a look like, "you know I could tell everyone at this table about your girly side, right? and he'd change his choice of words. He even began wearing panties to wear to class, as it made both of us hot. Sometimes we'd take a restroom break in the middle class and I'd stop him in the stairwell. I would begin kissing him and put my hands down his panties to feel him get hard. Then I'd just smile at him and say, "better get back to class."

We never started an actual relationship, we were just friends with benefits for a few months. I eventually dropped out of school and ended up moving across country with a boyfriend, but every once in a while, Justin calls and I humiliate him over his lacking masculinity while we both get off.