I was living with a few of my friends at the time. None of them knew or know to this day that I've felt this way or acted upon it. So needless to say, I was being very secretive that day. I kept in my room most of the time, especially after I found the guy I would end up hooking up with on Craigslist. His name was Chris, in his mid 30's (about 10 years older than me), slightly taller than me, in decent shape, and a bottom... He was a good fit for my first time. I explained to him my inexperience and nervousness about being with a guy the first time and he was totally accepting. He assured me he wouldn't pressure me into anything I didn't want to do and that I would enjoy my first time... He would be right.
We messaged each other for a few hours leading into the evening. Going over things I wanted to do and things he liked. He was looking for mutual sucking and to bottom which worked for me because I was not ready to bottom and really wanted to suck my first cock. We decided that a night meeting would be best because he was discreet as well. We could not meet at each other's houses because of this, so after a little assurance from him we decided we would meet at a secluded spot outside his place around midnight.
Once midnight began to get close and I was positive my roommates were asleep, I headed towards his house. The whole drive I was fantasizing about what was about to happen. When I arrived at his place he was sitting on the porch waiting. He was better looking than I hoped, slightly taller than me, older ( a turn on for me), a nice frame, and a nice manly face. We briefly introduced ourselves and he started leading me to his spot. The spot being a small sidewalk, hidden by a retaining wall, next to a lake.
As soon as we got to our spot partially hidden behind the wall he turned around and began making out with me. I was timid at first but quickly gave in and began aggressively kissing him back. We kissed and groped each other for a few minutes until we both couldn't take the waiting anymore. He slowly knelt down in front me, his face level with my cock which was about to burst out of my pants. He slowly undid my belt and pants, reached in and grabbed my throbbing cock. He looked it over, noticing and complimenting on how hard I was and the precum that was already leaking out. He slowly kissed and licked the tip, driving me crazy while doing it, then slowly shoved the whole thing in his mouth till I felt the back of his throat (I'm only about 6" so not too difficult I guess lol). He proceeded to give me the best head of my life for a few more minutes until it was my turn. I slowly grabbed his head and pulled his face of my cock, gently pushing him back and up so he was sitting on the wall and I could see his rock hard cock through his pants. I knelt in front of him and pulled his cock out of his pants. It was about the same length as mine, a little thicker and rock hard waiting for my mouth. I grabbed his shaft, feeling nervous and excited about my first cock as I did, and slowly licked the tip. As I felt it twitch against my tongue the feeling of wanting the whole thing in my mouth was too strong to bare. I wrapped my lips around the tip and slowly shoved almost the whole thing in my mouth, I loved it. I sucked his cock for a few minutes, him moaning loudly and complementing on my ability that watching porn helped me develope, until he decided it was time to fuck.
He slowly pulled my face away from his cock and made me stand up, face still slightly covered with saliva and precum. Then he began getting fully naked, asking me to do the same as well. While taking my own clothes off I admired his increasingly naked body and couldn't help but get extremely excited I was finally living my fantasy. After he was naked, he slowly walked over to the retaining wall putting his elbows on top of the wall and bent over. He then reached his hands back and spread his ass cheeks, showing me his tight hole that was waiting for me to fuck it. I became overcome with excitement and quickly walked over to him to begin caressing his ass. I loved feeling his cheeks and hole against my hands and had a sudden strong feeling of wanting to rim him, something I didn't really plan on doing. I bent down behind him, spread his cheeks and buried my face between them. Rubbing my tongue around and in his hole, getting it sloppy wet and driving him crazy in the process. After a couple minutes of getting his hole wet and ready, I was finally ready to fuck him.
I pulled my face away from his ass and pulled a condom out of the pocket of my pants laying on the ground near by. I put the condom on and stood behind him again. I gently rubbed the tip of my cock around his hole to get the excess saliva on it and teased him by pushing against his hole but not entering. Finally I began to slowly push the tip in, him lightly moaning as I did. I slowly pushed the tip in and out, going deeper each time until about half my cock was inside him. I slowly fucked him like this not going any deeper because I wasn't sure what would hurt him. His moaning became louder and his wet, tight ass took my cock better and better with each passing minute. The pleasure for him from this after a few minutes must have become too great because he finally let out a loud "Ya, Fuck me hard!" Caught up in the moment and without missing a beat I slid my hands from his waist to the top of his shoulders and thrust my cock all the way in his ass, feeling my balls hit his balls and taint. He moaned loudly and I began fucking him harder and faster. Each pump driving me more and more wild. It was surprising I kept up fucking like this for a few minutes because the excitement of having gay sex finally and his tight ass made me want to cum any second.
After a few minutes I pulled out of him and layed our clothes down on the sidewalk for padding and put him on his back on top of them. I rushed down to his cock and shoved it in my mouth, sucking it aggressively. He squirmed with pleasure as I began running my tongue between his cock and hole, getting it wetter for another round. He finally pushed my head back off him and spread his legs in the air to show me his hole again. I put his legs on my shoulders and shoved my cock back in his hole, both of us moaning from the pleasure. I fucked him hard for several minutes until I told him I was about to cum. He pushed me out of his ass, pulled the condom off and began sucking my cock aggressively. Each time my cock hit the back of his throat I thought I was gonna cum, until I finally yelled "I'm cumming!". He shoved my cock all the way to the back of his throat almost as soon as I got the words out of my mouth. I came harder than I think I ever have, shooting my load in his wet mouth and throat while he swallowed every drop. He had been jerking his cock while sucking me and came all over the both of us when I blew down his throat. We both got cleaned up and agreed it was an amazing fuck and I thanked him for a fantastic first time before I left.
We would lose contact after this and to this day I wish we had not. I would love to find him and show him that I've gained more experience to use on him