First Time for Everything
I was 21 and I had been crossdressing for a while. I had no idea I would later transition and become a transexual. Back then, it was all about the excitement of doing something apparently taboo, which really excited me. I felt dirty and embarrassed afterwards (thanks to my catholic upbringing), but I still loved it. I had started wearing my mom's and my s****r's clothes since I was 10 but I was growing taller and they were not. Had a problem with the shoes too. Dressing as Santa Claus for a 3rd Grade Christmas party at school gave me the opportunity to wear Mom's black boots in public, that was so exciting.That was the main reason why I went for the stretchy clothes and luckily, Mom's wigs still fit. I still did everything behind closed doors and when everyone was not home. Nobody knew, at least that is what I thought. I really enjoyed prancing around when no one was home; I came savagely several times, usually with something big up my ass, all the time wishing I had someone to play with.
At that time I was still going to college. I was taking a Philosophy class that most people thought was boring. The class included several extra practice sessions for the exams, and the professor had hired a couple of Philosophy major students to take care of them. That is when I met Carlos. Carlos was one of those volunteers. He was tall and had a thick built. He had a moustache and glasses that made him look older than he was. I met him at the cafeteria one time, and he told me to sit next to me to chat. He was a very interesting fellow. We chatted and during the course of the practice sessions we became good friends. One night he invited me to a party at his house, and I said ok.
I used to keep myself shaved and smooth back then too. I usually wore long sleeves and never wore shorts because I didn't want my buddies to see my smooth legs, that I kept nice and soft with my mom's lotions. But I guess Carlos must have noticed at one point. Must have been when I raised my hand in class because what happened next was well beyond what I had ever experienced.
I arrived around seven and he opened his door in a bath robe. He lived alone because his f****y apparently was well off . We went past his living room and told me to follow him to his bedroom. I stood in a room surrounded by dozens of dresses, nylon stockings, shoes and wigs. He even had a vanity, which I suspected full of make up items.
" I did notice you are very feminine, so I took my chance and decided to show you all the stuff I had collected. I do not dress anymore, but I do like to help out guys who still do" , he smiled and told me not to freak out, that it was cool. He said there were several guys that were coming over to dress and play girl and he had been hosting them for a while. Carlos then showed me three or four mini dresses and a couple of patent stiletto boots.
"I think these would look great on you! I noticed you have long slender legs, do you shave them too? I have stuff in the bathroom if you need to " ... I was delighted. I told him I had shaved the nite before and he told me to take my clothes off and try out the outfits.
"I wiggled myself into the tight spandex, neon pink outfit. "Wow, you look very sexy in that!", he exclaimed. He produced some silicone breast forms from a dresser and helped me put them on.
" Now you will have some proper curves, sweetie", he made me look in the mirror and I got an instant erection. I had never looked this hot and I loved what the 5"heel ankle boots did to my legs.
"Hmmmm, we have a hair problem to solve now", he said. He walked into his closet and brought two longhaired wigs. "Straight or curly?" I chose the wavy, long wig. Brown hair with blonde hi-lites was in back then. I had no idea what to do with the make up he then proceeded to show me, so he taught me how to use foundation, blush, eyeliner and mascara. Done with the lipstick, he asked me to look at myself in the mirror. I was transformed into a very hot young girl and it got me more excited.
"You will have to pay my services with a blowjob hunny bunny", Carlos was already pulling his pants down. He made me handle his big tumescent dark cock, until it was hard and then he showed me how to suck it. It felt soft, hard and warm inside my mouth, I really was beginning to like it. He made me kiss it and use my tongue to lick it like a popsicle. I tried to take it all in but i gagged several times. My come had been dribbling on my under wear and they were literally a huge wet, sticky mess. I pulled the minidress up and took off my shorts, while Carlos jerked himself and watched.
"Come here sweetie, sit on my lap while you give me a handjob. I do not want to come and mess up your make up... yet", I grabbed his cock, squeezed it tight and gave it a vigorous handjob. Carlos groaned and came in long spurts. But he remained hard as a rock.
"You are going to like this a lot, come over here and bend over the bed, I promise i won't hurt you." I was petrified, I never thought I would be turning into some kind of gay guy playing with cocks, but I obeyed. He lubed me well and stuck a couple of fingers in. It was very tight, so he kept playing with his fingers in my ass for quite some time. By this time I had already cum twice on his sheets and he looked quite pleased.
"Have you seen porn? ", he asked. I nodded. "Ok when I penetrate you, you are going to scream, moan and call my name like a girl, you understand?" That really got me hard again, I nodded eagerly. I felt a burning sensation at first, and he was in. He thrusted it deeply and I moaned. He kept going in and out for several minutes while I wailed and enjoyed my first fucking.
"Oh you scream like a cheap whore, and your hole is so tight,mmmm. Nothing like a young man's virgin ass..." He kept thrusting but now he was groaning. " I'm coming baby, tell me how my cum feels in you, aaaahhhhh!!!!" I felt him tense up and then I felt a warm gush, like an enema up my poop hole. He fell on top of me and pinned me down for a few minutes, with his dribbling cock still inside me.
After a while, I turned around and he smiled. "Your make up is still perfect, lovely" . I smiled, and he stuck a finger up my ass, and his cum came out in a rush. It dribbled on the bed and made a big puddle.Since then, I have had a thing for creampies and guys cumming in my ass. I like the semen seeping out of my ass and the warm sensation as it finds it's way down my legs.
"Hurry up and clean yourself, the party is about to begin", he said. And what happened in it is the plot of my next story ...