First Time Dressed… at an Electronica Conce
I had been dressing as a girl to get off for some time now. For some reason there is nothing that turns me on more than a tight little cotton thong stretched across the bud of my asshole, holding my tiny little boy toy down where it should be. Over the years I’ve slipped into my mom and s****r’s underwear drawers while they were out and stolen the sexiest piece of clothing I cold find, most likely leaving them wondering where all their stuff went. This practice has gradually become a longer and longer as every time I do it I have a hard time taking the clothes off. Within the first few times, I began sticking things up my ass and loving it. First starting with tiny little razor blade handles, including on that vibrated, and eventually got myself a dildo. I still have trouble getting the dildo into my tight asshole, but once I do, I can fuck myself with it for hours, literally.
Looking at porn and reading stories dressed up always made me extremely horny. I would fantasize about being with a man. Being dressed like a dirty slut and having some sexy stud figure out I wasn’t actually a girl. The idea of dressing up and going out never really received much consideration, until one night when I ended up going to a techno concert by myself. My friend and I had planned on going to see a DJ, then last minute they ended up getting called into work. It was disappointing to find out with such short notice, but I quickly started thinking. I had gone to plenty of shows like this, but never by myself.
I happened to be on my computer at the time and decided to look at some videos of t-girls. In one video, a sexy retro crossdresser was dancing at a nightclub and some super ripped guy started dancing with her. They ended up going to the bathroom and having sex, at first he acted surprised that she wasn’t a real girl, but of course ended up screwing the shit out of her. Anyway, I decided that I was gunna try and dress up for the concert. I quickly went to my dresser and pulled open the drawer I kept my gurl clothes in. I figured it was going to be pretty hot and sweaty at the show so I would dress as if I were going to workout. I had the prefect outfit for this look, in fact I had even worn it a few times while actually workout. I figured id try and be as sexy as possible, so I went into my bathroom and shaved my entire lower body. I put on a pair of black, thigh-high, athletic socks. Then chose a pink cotton thong, which I covered merely with a very small pair of grey cotton shorts that hardly covered my whole butt. On top I wore a black sports bra and a loose fitting, yellow tank top. I had put make up on before, so I already knew what to do. I definitely looked passable after applying a decent amount of eye shadow, some bright red lipstick, and a bit of blush. I had pretty long hair at the time, so I put it up into pigtails with some yellow hair ties. Then I grabbed the tickets and left for the show.
Since my friend couldn’t make it to the show, they had asked me to try to scalp their ticket so it would go to waist. I didn’t live far from the venue so I walked. On the way I noticed several men looking at me, which was a huge turn on. As I approached the venue I slowed down to look for someone to unload the extra ticket to. Eventually, after a few minutes of pacing around, I noticed a big black man looking at me. He walked over to me and asked if I needed any tickets. I told him no, that I was actually trying to sell an extra myself. He told me that even though he was having a hard time selling any of the tickets he already had, he would buy mine off me to help me out. As he spoke to me, his eyes moved from my face down to my legs and then back to my face, and gave me a big smile, followed by a wink. I awkwardly said thanks, turned and walked towards the doors. As I walked away I quickly glanced back at the man and saw him looking right at my ass. Once I got inside, I just tried to act cool. I found a spot on the dance floor and started dancing a little bit. By this time the ecstasy I took at home was beginning to take effect. I found myself moving more and more to the music. It was such a rush to be out at a show in girl’s clothes strutting my stuff. I began gyrating my hips and shacking my ass. My hands began to move across my body. I was in heaven. Then from outta of no were, I felt someone else’s hands on my waist. Followed by a body grinding up against my butt. I turned around and saw that it was the same big black guy I sold my extra ticket to earlier. Before I could say anything he moved in towards me and kissed me full on, tongue in my mouth and everything. It felt incredible to be kissed by this big strong black man, having him grab each and every inch of my body, digging his hands into my butt cheeks. Eventually he made his way around to my front side and felt my little dick. He paused for a moment, then simply continued to kiss me. Apparently he didn’t mind that I was actually sissy slut instead of a real girl. After some more kissing I eventually turned back towards the stage, grinding my butt up against his now semi-erect cock. As we danced on I guided his hands around my body, and occasionally turned my head back to kiss again. As we continued to grind hips, and he continued to grind his now fully hard dick up into my ass, I myself began to start hardening. I felt hornier than I ever had. My gapping butt was pulsing, longing for something to penetrate it. I turned around and started kissing him again. I broke the kiss started sucking on his earlobe. Then I grabbed his hand and reached it down into the back of my shorts, I whispered into his ear for him to finger fuck me, and almost instantly his fingertips began prodding the bud of my asshole. I took his hand out of my shorts and gave his fingers a nice long such, then let him return them to my asshole. I was in a state of bliss, dancing to some amazing music, grinding and making out, and being fingered by a big hot black man. After letting him finger my ass for a little while he told me he was ready, and I knew exactly what he meant. He asked if I wanted to get off of here, we could go back to his place, but I said didn’t want to leave the concert yet. He took me by the hips and turned me back towards the stage. Then he reached down underneath the bottom of my shorts and kinda yanked them up and little but and to the side, then pulled my tight cotton thong across to the other side of my butt hole. I instinctively undid his zipper as he was doing this and pulled his cock out. I spit as much spit as I could onto my hand, stood up on my tippy toes, and lathered my hole as well as I could. He did the same to his dick, then pressed it up against my bud. I turned to him and told him that he was taking my anal virginity. With out hesitation, he slammed his hard cock through my opening, almost lifting me up into the air. I let out a huge scream, but no one seemed to notice from the music. I instantly began panting, gasping for air. I had never felt anything like this before. At first he was slow with his thrusting then as I started grinding my hips once again, he increased his speed. I honestly couldn’t say how long this lasted before I eventually lost control. I could feel myself getting closer to climaxing and all of a sudden my body went partially limp and I shot a big load of cum into my panties. He must have sensed what was coming because he held me up while I came. A few moments after I came, so did he, shooting his hot jizism deep into my ass. After he finished, he put his cock back into his pants and we continued to grind our hips. I could feel his hot semen begin to drip out of my wet hole and down my inner thighs. He reached his hand into the front of my shorts and caressed my small cock, trying to get a sample of my cum on his fingers. He pulled his hand out of my shorts and shoved it into my mouth, telling me to lick it off. My own cum tasted excellent, so I reached down between my legs and tried to scoop up whatever of his cum that hadn’t gotten to far down my legs. I decided to quit while I was ahead, so I gave him one more long kiss and told him I was leaving. As I walked out of the concert, I could tell that some people were noticing the cum stain on my shorts, I didn’t care what they thought though, I was so satisfied from having just lost my virginity. That show might just go down as my favorite ever.