My Initiation by islutmyself54

A literotic sexstories: My Initiation by islutmyself54 ,
I am a bisexual man, or transvestite. I love women, everything about them. I get really turned on by them and love fucking them. But I also get turned on by the thought of being a woman. I love dressing like a girl, acting like one, sucking dick, getting fucked. I’m not even turned on by men at all, but I get turned on by wearing women’s clothes, sometimes even by looking at them. It makes me want to be a girl, and just please any guy, anywhere, just for men’s pleasure, I don’t even care if I enjoy it myself. I love feeling like a slut, a whore, like I’m a piece of ass for men’s pleasure. I don’t care what the man looks like, as long as he is older, has a dick, and it works. I love having men wanting to look at my ass, trying to grope me, and use me like a blow up doll. I will be writing some of my experiences and hope people out there enjoy it.It all started when I was in that 1st grade age, maybe a little younger. It might have been the summer between 1st and second, I’m not sure. My front neighbor was Caeser, a kid about a year younger than I. We would hang out and roam around with other kids in our neighborhood. Caeser took me to the house of an older kid named Alex. Alex was about 15 or 16. He was a poor kid, that seemed to always be alone, I never saw his parents around. He had this playhouse type deal, behind his actual house, that we would always hang out at. It was like a treehouse of sorts, except not in a tree. It had a really low ceiling, to where you had to bend down even as a kid to walk around, but it was pretty big. It had about 4 rooms, with like old mattresses in each one. Alex claimed he made it himself, which was really impressive for us. The walls were wooden with a wooden ceiling that leaked, and no actual doors and glass windows. He had a sister about our age, but we wouldn’t see her around too much either, she was always roaming in the street, mostly by herself, sometimes with other girls. I remember one day we were hanging out and she showed up with another girl about our same age. Alex said that was his girlfriend. His sister sat down with us, eating some chips. The other girl sat next to Alex and they began making our a bit. Alex reached up her skirt, pulled her panties down, and went between her legs missionary style. The girl seemed elsewhere, she would moan with every thrust Alex gave her, but she didn’t do much else, just lay there with her legs open. Her moans were really loud, it even sounded like she was in pain. But she kept taking it. Her moaning is something I remember to this day. It was the first time me and Caeser saw sex, so we didn’t really understand the whole concept. Alex’s sister sat there watching and eating her chips, like it was nothing. Alex finished and his sister walked away. She came back with a roll of toilet paper, that she handed to her friend that was still laying there. She took the roll and wiped her pussy. Throuhout the whole time, I didn’t know where to look, they were all so calm about it, I would look away and back constantly. Caeser just watched the whole thing with his mouth half open, half smiling, amused by the whole thing. The little girl made out with Alex a bit then left.

We were hanging out at his playhouse one night, the playhouse didn’t have light, but the light from the street came in through the door and windows and gave us enough light. Somehow the subject of sex came up, something Caeser and myself had no experience in. Not like sex with girls, just sex. Can’t remember how it went, but somehow Alex got us into agreeing to take turns fucking each other. I didn’t know anything about being gay, at least not in the concept I know now, I guess we saw it as a game. I don’t remember exactly how we decided, but I had to play the girl first, and let them fuck me. I pulled my pants down and lay face down in one of the mattresses. They both got closer on both sides of my ass. I felt their hands gently pass over my ass and legs. I remember it felt really good being touched like that. Alex said I had a nice ass, that it was really white, while they both continued groping me. I got a few small spanks. They both began kissing my ass and the back of my legs. Caeser seemed really excited and telling Alex, “look at this.” as he opened my ass. Ceaser hands held firmly to both my asscheeks, and held them open, admiring the view. I felt Alex reach his larger hand between my cheeks, and slowly began pushing a finger inside. His finger felt really thick, and it hurt. I complained and Alex pulled out, then tried again. He fingered me on and off, then pulled his pants down. Caeser moved to the side next to us to watch. Alex climbed on top behind me, and began pushing his dick into my ass. It was really painful. I screamed and he pulled out. He put some spit in my ass and tried again going a little deeper, then pulled out when I screamed. I turned around, and his dick looked huge to me. I felt really opened just from that penetration, like I was gaping. My anus was in pain. I told him his dick was too big while caeser looked at it in awe, agreeing that it was huge. He decided to give it another shot, and put it in me again, with the same results. We decided he was too big, so he let Caeser have his turn. Caeser pulled his pants down, his dick was much smaller, even than mine. He climbed on top behind me. I felt his small dick go into my ass a bit, and he began thrusting slowly. He wasn’t going deep inside, he might have been too small, he was just fucking the entrance. It didn’t hurt at all, it felt awesome. I wasn’t about to orgasm or anything close to it, I just liked the way it felt having his dick in my ass. He only went for about a minute, while Alex watched. Then they switched again. Alex climbed on top of me, and put his dick in my ass. He went really deep and I screamed in pain. He pulled out and said he would just put it the tip. I suppose since he was older, he actually knew much more than us about this. He pushed the head of his dick into my ass, which hurt, but it was tolerable now. He began fucking me, not going very deep. He told me to push ass up when he fucked me so he could feel it better. I began moving my ass like he wanted, while caeser watched amused and turned on by the situation. Alex eventually stopped fucking me, I don’t know if he came, and didn’t even know he was supposed to. He just stopped and I told them it was my turn. Caeser laid down face down to replace me. I remember he had a very distinct smell when I got close to his ass, it wasn’t like he stinked, it was just weird. Alex and I groped at his little ass for a while, and Alex began trying to finger him. He complained about how it hurt, and we moved on to me being next to fuck him. I climbed on top of him, and began putting my dick in his ass, he complained a little, but he didn’t need me to pull out. I began fucking him, and it felt good, but at the same time, I didn’t like it too much. I fucked him a little and let Alex take his turn. Alex got on top of him and I saw his huge dick going in. Caeser complained about it being too big and he pulled out. He put spit in his ass then went again with no better luck. Eventually he gave up, and Alex lay down and replaced Caeser. I remember getting close to Alex and he did stink, he had a musky smell. I got on top and put my dick in him. He didn’t complain at all, and I probably didn’t go very deep. I fucked him for a little bit, then Caeser took his turn. He didn’t even feel him. We gave up on trying to fuck him. We decided caeser and I would be the ones getting fucked. So we switched back and forth a few times, neither of us getting off. Alex would jump in and out trying to fuck us. Caeser gave in trying to fuck, and he would let us try to fuck him. Eventually I gave up trying also, I hadn’t really enjoyed fucking, only getting fucked by Caeser. Alex asked me if I wanted to continue taking turns with him, but I didn’t feel like fucking him so I said no. So he asked me to let him fuck me cause I had a good ass. I layed down again while both Alex and Caeser agreed I had the best ass to fuck. Alex got on top, and put his dick in my ass again. It hurt, but this time he put about half of it in. It felt a little better this time, so I began shaking my ass the way he wanted. I felt him fuck me and fucked me for what seemed a long time. I felt my ass was really open. Caeser would cheer him on and rub my ass and legs. After what seemed like forever, Alex said he was done. I don’t remember much after that, just me and Caeser telling him how huge his dick was, and him saying I had the best ass. we agreed we would take turns on each other again soon. As Caeser and myself walked back home, Caeser kept saying I had a great ass. I would not admit it, but I had enjoyed having my ass groped. Even the fucking, even though it was mostly pain. I was glad they had enjoyed my ass, and knew I wanted to try it again sometime. This would be the beginning of my journey.

I will be posting my second story soon. Because they are from memory, I can’t remember all the details from that age, but I will be more detailed in my later stories. Hope you enjoyed, rate, and comment.