Bi Boy - The hang out

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The awakening, part 2 - the sex

We made plans to go out on a Friday night. Nick came over to the apartment that I was living in in the Boystown area of Chicago. He looked good. He was wearing a red shirt but it didn't matter what he wore. I wanted to rip his clothes off as soon as he walked into my apartment. We went out and had some drinks and talked. We had these great conversations, not the awkward first date conversation. It was as if we had known each other for ages. It was so natural. After a bit we headed back to my place. We both knew we were going to have sex that night. It was a foregone conclusion from the way we looked at each other when he arrived. We got back to my place and my roommate was up. We chatted for a bit with him and he eventually left us in the living room. We started kissing like bandits. He was such a good kisser. He knew how to kiss using his tongue but it never was over the top or sloppy. I remember sitting on the couch and watching him take his shirt off. He was wearing a tank top underneath but watching him calmed me down. The nervousness left my body. I wasn't thinking about my one month rule. I threw myself into the moment. We continued kissing until Nick suggested we go to my bedroom. We kissed all the way into the room, moving oddly but strangely in rhythm. We went into the bed and slowly the clothes came off as we moved further along. The first time I saw him naked, I stopped and almost pinched myself. I couldn't believe this was happening. I also thought that it so unfair. He's so beautiful and so much fun and to have a huge cock too. I started sucking his cock. I couldn't get it all in but I loved it. He was enjoying it too. He pushed me down to his ass. I had never eaten a man's ass out before. I was hesitant but knew from my experiences with girls that I liked eating out pussy so I went for it. Not knowing what I was doing wasn't a problem. I learned real quick that I liked it. A lot. I stuck my tongue in and out, moved it around, licked, dug deep. I couldn't get enough. He was turned on. He wanted me to fuck him. I grabbed the condom and did. It felt so good. Being inside him, kissing him, grinding my cock into him and having him want me as much as I wanted him. I was surprised that I lasted as long as I did. After I came, we kissed and he asked if he could fuck me. I wanted this to last as long as possible so I said yes. He tried to fuck me but as soon as he he stuck his dick in me, I felt pain like I had never felt before. I literally saw white flashes of light. I'm not sure if they were stars or not but he stopped. I told him I want to continue trying. I got on top of him and eventually lowered myself on top of him. He was so big it hurt but eventually it felt good. Right before he came I pulled off him and I can tell he wanted to cum inside but I'll never forget watching the cum accumulate in the condom as I watched. I fell onto him and we kissed. He told me that he never came that way before. Eventually we fell asleep. The next morning we woke up and I fucked him again and we well asleep in each others arms. It continued like that for the rest of Saturday and Sunday. The only time we weren't in bed was when we ate, went to the bathroom or showered. Looking back, I think Nick realized that I gave my virginity to him that night. He treasured it and respected it. The funny part was that I think he thought it was the first time I had ever been fucked. It wasn't but it was the first time that I had ever fucked a man. The curious part is, while I do remember it the most vivid memory of that night is me pulling off his cock and watching him fill the condom with his cum.

An evening with space

I spent a nice another evening with Space Cowboy who I think will keep this name from here on in as he is kinda dingy and does remind me of Jason Kay. It was last minute but we made plans to hang out, drink some wine and watch some videos. I arrive at his place and we had a long talk about whats going on with him. He's under a lot of pressure with school finishing up and looking for a job in this crappy economy. We cuddle and watch a TV show on DVD. We make it through one episode before we are kissing and all over each other. We take it to the bedroom where Space is really into sitting on top of me naked grinding his ass into my cock. We probably spent about 30 minutes of body grinding with intermittent kissing. I was totally horned up cause I was precumming all over him. i told him I wanted to fuck so he lubes up my cock and sits on it raw. He rides me for a good 10 minutes before I switch positions and start fucking him missionary. I'm fucking him pretty good, alternating between long strokes and fast, hard ones. All the while he's jerking his cock and he tells me he's close. I love to see a guy cum so I stop fucking and start sucking his cock cause I want to see him cum up close. He's a bit surprised but it doesn't stop him from cumming. I take his cum, use it as lube on my cock and start fucking him again. He complains about me using his cum as gross and asks me to stop because it hurts. I've fucked him 8-10 times and he's never told me he couldn't fuck after cumming. I usually cum first though except for maybe one time and he fucked after he came. But he did try to rush me, so it makes sense. We hang out in bed talking about life and kissing. I love feeling up his smooth twink body. It was nice to have this romantic banter going on. Not knowing how long is long enough, I ask him if he wants to fuck again. He says yes so he wraps his legs around me and I aim my cock against his hole and push it in bare again. I start fucking him again. I'm pushing myself this time cause I'm not sure how long he's going to be able to fuck and I really want to seed in him. After about 10 minutes, he asks me to stop cause he's getting sore. I do and he asks me to jack on him. I get on top of him and start jacking my cock and when I get ready aim for his face. I miscalculate and get it all over the pillow, the one I'm going to be laying on. Fuck it, it's my jizz so I do. We kiss and cuddle for a bit before I shower and return home to my bf who is sleeping soundly.