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One day I was talking to a younger guy in my class. I was finishing my associates. I was 27 at the time and he was 18. He was think and petite with long brown hair. We had gone to his house a few times as study partners in our history class. One night I was just going to take my xbox over and were were both going to play some games. When I got there he had been drinking with some friends earlier. I started hooking up my xbox to his other tv we put next to his. I assumed he was straight until he turned on his tv and some gay porn was left where he stopped watching it. He quickly switched it and I pretended not to see. He awkwardly glanced over at me and I didn't make eye contact. He was obviously embarrassed. We played some games for a bit talking a little bit. so keep in mind im bi but no one I really know is aware. I took some shots and started to get a buzz. We played for about 15 minutes before i noticed he had his controller vibrating on the side of his penis. I still tried not to look directly as he was basically doing it on the down low. I started thinking that first of all he was watching gay porn so he may be open to having sex. He was getting him self semi hard with the vibration on the controller. I started thinking more and more how hot it would be if we actually had sex or a bj. He was wearing basketball shorts with no underwear and a t shirt. I asked if he felt like going out and smoking a cigarette. He said yeah lets go. We smoked and talked for a bit before going back in. He went in first and I couldn't help looking down at his ass as he walked back to his room. We played some more. I started getting horny and was thinking about how I could bridge the gap. I had a picture of my cock on my phone with some other regular pictures of my vacation to California. I figure let him flip through the pictures and he will see my cock. whats the worst that can happen. He started flipping through them making comments until he got to the one of my hard cock. He didn't say anything and I acted like it was an accident and said sorry going to grab my phone back. He pulled it towards him and said wait i want to see it. I immediately got hard. I said haha ok yeah you can look at it if you want. As he was looking at it i pulled my pants down to my hard cock was fully exposed. He looked over with surprise. He asked if it was ok if he touched it. I said yeah that's fine. He started stroking it gently and rubbing my balls. As he touched me i reached over and slid my had up his leg through his shorts. I felt his hard cock. Not the biggest cock but very nice and still average size. I asked if he could suck it a little bit. He got on his knees on the couch to the right of me. He leaned down and put my cock in his mouth. It was so warm I moaned with pleasure. As he was slurping on my cock I kept rubbing his cock and slide my had up to his smooth little butt cheeks. I could feel the warmth coming from his ass hole. With out asking i gently got some spit on my middle finger and reached it up over his back to his warm butt crack. I felt around until I got to the his butthole. He just moaned and kept slurping up and down my cock. I said lets get on the bed. We both got fully naked and got on the bed. He sucked me as i sat up on his bed. his long hair kept getting in the way so he put in into a pony tail. As he was sucking I grabbed another hair tie off the night stand and asked if he was down to put it in pig tails. He said yeah sure that sounds hot. His parents were out of town so I asked if he had any of his moms make up or clothes he could put on while we played around. He said he could grab some red make up and some eye eye shadow. He came back with the make up, a thong, bra, high heels and a little sun dress. He said I havent done this before and wanted help putting the makeup and bra on. One we were done he got on the bed and said what do you want me to do? I had him layback i lifted his dress and parted his legs. His cock and balls we contained in the black crotch of the thong. I pulled it to the side so his cock and balls were exposed. I started sucking his cock and fingering his ass with spit as lube. He moaned as I continued playing with him. I asked if he can flip over. He flipped over with his ass poking up. I pulled down his thing and pressed my face into his hot little butt crack. I started licking and kissing his balls and asshole. He said that he really wanted me to fuck him dressed up like this. I grabbed some coconut oil out of the kitchen for lube. I came back in and he was on the bed with his ass to the sky. His thong still around his knees I started something his little pink hole with oil. Playing with it and stroking his cock. i lubed my self up and put the tip of my cock to his hole. I started pressing in. he said go really slow. I started working the head in. I could feel him tensing up. it took about five minutes before I started to be able to slide my cock in and out. I kept pumping occasionally slipping it out and slapping it on his ass and balls. He said he wants to to finish inside of him. H kept drilling his little hole as he moaned and gasped. I grabbed his high heels and kept fucking the shit out of him. Ii was pounding his ass relentlessly and he started to say he cant go any longer and we wouldn't need to stop. I just kept drilling his but. He said really Its starting to hurt I need a break. I said just a little longer im almost there. He groaned and said ok but hurry. I spread his ass and pumped until I shot a fat load deep in his ass. I stayed there for a couple minutes before his ass squeezed out my cock followed by some of the load. He just laied the with cum dripping out of his ass. We cleaned up and I went home. I asked later if he wanted to do it again and never got a reply back. That was the end of it but it was definitely a hot encounter