This is the story of my first she male. I had always been curious about dicks. I had always been attracted to women and I loved to watch a woman get pounded by a big cock. But after awhile I realized that when I tried to imagine the porno, I always imagined myself in place of the girl. One day, when I was sixteen, I decided to see what it felt like to be a girl. I had never tried anal before (I could never bring it up to my girlfriend) but I knew I had to try something. So I gathered all the necessary tools and went into my room. I locked my door so my mom wouldn't accidentally walk in on me and slowly got undressed. I had a full-length mirror that I loved to look at myself in.
I was about 140 lb with dark brown hair that got into my eyes occasionally. I had a flat stomach, a nice bubble butt, and a 7-inch cock. As I was looking in the mirror at myself I slowly got turned on thinking about my own virgin asshole. I turned, with my ass to the mirror and bent over to I could see my tight little sphincter as clear as possible in the mirror. While I watched I grabbed the jar of honey that I had brought down. I put a little on my finger and softly touched my asshole jut to see how it felt. It felt like it felt pretty good and I slowly rubbed circles around it. I decided I should just go for it. With one quick poke my finger was all the way inside my ass.
It was extremely uncomfortable and my first instinct was to pull out but I stuck with it. I started moving my finger inside and feeling around. That’s when I discovered the spot that changed my life. I didn't know what I had just touched but a warm feeling just went over me and my cock stood at attention. I just couldn't stop rubbing that special spot in my ass because it felt so good! I was still looking in the mirror, through my legs, and I could feel my cock about to let go of its salty load. Without warning my cock started spewing cum all over my little boyish face. I was absolutely unprepared for how much cum I had and when I stood up and looked in the mirror I could have sworn I looked just like the bukkake porn I had watched that morning. Looking at myself in the mirror, I licked my lips like the whore slut I was imagining myself to be. Then and there I knew: I liked things in my ass.
Pretty soon I started to imagine what it would be like to have someone else’s finger fucking me from behind. I couldn’t bring it up to my guy friends because it was far too embarrassing (and besides, none of my guy friends seemed all that attractive to me.) and my girlfriend was most definitely not into anything kinky. So I was stumped for a good week or so. But then I had the brilliant idea to go on the Internet and try to find someone who suited my needs. I decided the craigslist personals would be a good bet.
Now, as I mentioned before, I was fairly new to all this. So when I browsed the ads, I had no idea what a ts, tv, or even a shemale was. One ad wrote, “I’d love to make your fantasy cum true. Drop by after eleven cause I can host xoxo ts Brianna p.s. please reply with pic” and then it had a picture of a drop dead gorgeous woman. I figured what the hell right? The worst she could do is tell me to fuck off. So I emailed her that my fantasy was to have someone explore my ass. She replied almost instantly, saying that she would love to meet me tonight if I was available. This was far earlier than I had imagined. But I was the one who contacted her so I would feel terrible if I flaked out on her now. I asked for her address and she gave it to me. I told my mom that I was headed to a friend’s house to stay the night and I wouldn’t be back until tomorrow. I decided to wear some loose fitting clothes so I could get out of them easily. Her house was only a few blocks away and I decided to walk because it was a nice night.
As I approached her door my stomach got all knotted up from the nervousness. I almost had to f***e myself to knock on the door. She didn’t answer. I had just decided to go home and forget about it when I heard the latch turn. And when the door opened my jaw dropped. Her face was so beautiful it took my breath away. She had dd tits with a tight short sleeve shirt that showed her midriff and a mini skirt that left her legs wide open to my young, perverted stare. She stood about an inch taller than me with her high heels on. “Hello, you must be tony right?” she asked. All I could do was nod my head. She must have sensed my nervousness because she said” I won’t bite. C’mon in and make yourself at home.” I followed her in through the front door all the while watching her magnificent ass sway back and forth. We both sat on the couch and she said “ so tony, have you ever done this before?” I said” no, this is actually my first time. But I learn fast.” She just laughed and said, “ Would you like a glass of water or anything?” I politely declined and we sat and chatted for a minute. As we were talking I noticed that her hand had started to creep up my leg. I was slowly getting aroused and it was becoming pretty obvious even through my loose jeans. She glanced down and with a huge smile asked, “Would you like to see my bedroom?” yet again; all I could do was nod.
She took me by the hand and slowly led me to her room, which had a full length mirror on her closet doors (much like mine) and a four-post king size bed. She pushed me softly onto the bed. “ Don’t be nervous.” She said, “Just try to relax and let me take care of everything.” She pushed me all the way back so that I was lying on the bed. To my surprise she kissed me. I was already so turned on. She slowly worked her way down to my pants, all the while, keeping eye contact with me. She had such a seductive smile. As she unbuttoned my pants, my cock strained to be free. When my pants were gone she kneeled in front of me with nothing between her mouth and my cock but a thin piece of cotton. She pulled down my boxers in one swift motion and my cock sprang out and slapped her in the face. I was so embarrassed but she just laughed and took it in her hand. I hadn’t developed far enough to grow any hair yet so it looked huge in her tiny hand. I could have exploded right when she touched it. I wanted her to keep touching it and to put it in her mouth but she had other plans. “Turn over” she said “ onto your stomach. I want to see your cute ass.”
As I turned over I felt so slutty with my bare ass and balls facing her. She slowly ran her finger down my crack and I shivered with pleasure. “ Have you ever had anything inside you?” he asked. “ Only my finger and just once” I replied. She let out a giggle. “So you’re really a virgin?” “An anal virgin, yes.” I answered. “mmm, well I bet it’s really tight then” she moaned. The whole time we were talking I could feel her hands caressing my balls and my ass and her fingers exploring the outside of my little hole. She reached into her dresser drawer and pulled out a small bottle of lube, of which she proceeded to squirt down my crack. I could feel it slide over my asshole. Soon her finger added to the feeling as it slowly probed the outside. She started pushing a little harder and I moaned a little. Bent over the bed with my ass to a strange woman, I felt so vulnerable but I had never been more turned on. Her finger slowly started to slide inside me. She was far more careful and slower than I had been and I could feel every nuance of her finger as it entered my rectum. I felt the first knuckle entered and then the second. I couldn’t help but moan a little more. She took her time, slowly sliding her middle finger in and out, enjoying the sounds I was making. Then I felt something else. It was her other finger. I decided to trust her to do her thing and raised my ass a little higher in acceptance. As both fingers twisted in my ass I almost came right there. And I would have if she hadn’t pulled out.
I glanced back in time to see her pull up her miniskirt and move aside her panties. What I saw shocked me to my core. It was a long, thick, cock. I was stunned by how huge it was. I got extremely frightened and started to get up. “ I can’t do this” I said, “I’m not gay” I started to gather my clothes but she had my pants. “ What the fuck did you think a TS was you idiot?” I was thoroughly scared now because she looked angry enough to hurt me. “ I… I don’t know… I didn’t even think about it,” I stammered. I reached for my pants and she grabbed my wrist. “ No! I gave you your fantasy, now you can do something for me!” and with a quick push she shoved me back on the bed. I was still in shock at her sudden roughness and I didn’t even react. I could have easily overpowered her but I just wasn’t thinking straight. Before I even knew what had happened she had grabbed a pair of handcuffs and handcuffed my hands behind my back. My ass was to her again just as it was before. Except this time I was far more startled. “now we’re going to fix this virgin problem of yours” she said with an evil grin. I couldn’t see behind me but I could hear her lather up her cock with the lube. Then I felt the large head against my asshole. I begged her no but she just ignored me. I held my breath as she pushed it into me.
There was a pop and a pain unlike anything I had ever experienced tore through my ass. She had buried her gigantic cock in an instant. “dear god, you are tight aren’t you? She said with obvious pleasure. I had started crying but as she held it inside of me the pain slowly started to subside. Ever so slowly she worked it in and out of my ass. I could feel it sliding back and forth and I could hear the sound of her balls slap against mine as I lay face down on the bed with may ass over the edge being plowed by the biggest cock I had ever seen. But to my amazement, her cock started to feel good! It was rubbing inside that nice spot in my ass and I started to feel myself get a boner again. It was rubbing against the bed as she started increasing her pace and rocking my body back and forth. I knew I was practically being ****d but I couldn’t help but start moaning again. “the little bitch likes it doesn’t she?” she asked me. When I didn’t answer she slammed cock into me as hard as she could and shouted “doesn’t she?!” I whimpered and said” yes, the bitch does” she increased her pace even more and I felt my ass being slapped like the bitch I had become.
Then in midst of it all, I felt an explosion of warmth inside of me. I knew she had coated the inside of my ass with her cum and the feeling sent me over the edge and I came too. She quickly pulled out and turned me over. Getting on top of me, she straddled my face and when I opened my mouth to protest, she dropped her balls into my mouth. I could taste her sweat and her cum as it dripped down from her huge cock. What else was I supposed to do? When you have balls in your mout it’s just instinct to suck them. I even started getting into it and playing with them with my tongue and rolling them around in my mouth. All the while I could feel the cum drip out of my used ass. When they were all clean she turned around so that her cock was pointed down my throat. She didn’t make me suck it that time but she made me clean her cock of all the cum that was on it.
To be continued…….
Assuming everyone likes it. J a few good comments and I’ll tell you the rest of the story!