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Up For It  

SRockets 47M
0 posts
11/19/2020 3:15 am
Up For It

As I've mentioned before, I have credit those old America Online rooms for allowing explore my sexuality. Although I rarely acted it. For years it was just an additional masturbation fantasy, because in the rooms it was interactive. From talking other men, I could get an idea of what I wanted try and what I didn't.

But in order for gather the courage go out and meet someone, as appealing as it sounded, I always made excuses for why I wouldn't actually go. I've written previously about going another man's house for a blowjob, but it was a few years before I met someone else online. That was a just a pants-less jerk off porn together. He was as inexperienced as I was and we didn't touch each other. I wanted to do more, but he didn't.

And that's fine...

I still had that desire for more, but not enough to actively pursue it. I spent a lot of my masturbation time in the rooms talking men (and men pretending be women), but nothing moved me enough move ...

A few years later, I started talking a guy that lived about 25 miles away from . Before long, we were online chatting at least once a week, if not more. He didn't consider himself gay, but he was single. He was also interested in helping live out my fantasies. I'd told him what I'd done and what I wanted to do. I really wanted to have my ass eaten, and I really wanted to fuck another man's ass. But I wanted to do it bareback and cum inside him. To , this seemed like a pretty tall fantasy. Multiple times he said that I could do all that with him and more.

But I had come over his house.

The problem now was that we had become friends through the online chatting. Meeting him might be<b> weird... </font></b>When I've met someone in the past, it was a spur-of-the-moment, impulse thing. He wanted make plans meet. While that makes sense for both of us, it wasn't comfortable for me do that. What if at the time agreed upon, I was feeling insecure and chickened out? That was very likely knowing my personality, as I do.

When we talked online he started giving me crap about that. He would complain about us just talking about what we wanted do each other online, but I'd never actually follow through on it. It made feel kinda bad after a while. I was working second shift at the time, and would get home around midnight. One night I got home and was extremely horny. I logged into my account and looked at the rooms.

After a couple minutes, I got an instant message from him. After brief small talk I said him:

"Are you available tonight? I'd like to come over."

He instantly agreed and gave me directions. I already had his phone number as we had our first conversations over the phone a couple weeks earlier. I'm sure having phone sex with him warmed me up and gave me the courage to meet up in person. I told him that I was going to take a shower and I'd drive over.

That shower was about as thorough as I'd ever taken. I soaped up and washed my cock several times. I washed not just my crack, but slipped a soapy finger inside my butthole and felt around. (And it felt good!) Just in case... I had no idea how the night was going to unfold. Then I rinsed off, got dressed in my favorite silk boxers, and drove over to meet him.

He invited me and led me to the kitchen, pulled up a stool for me to sit on and offered to make me a drink. Previously I told him that Jack and Coke was my go-to, and he had it for me a few seconds later. After handing me the glass, he kneeled down in front of my and started unzipping my jeans, I leaned back to give him better access.

"I want to taste what you brought!" he said, pulling my cock out and wrapping his lips around me. his mouth felt heavenly, but he stopped after a few seconds And said we should go downstairs. I took off my shoes and followed him to a living room on the lower level. He asked me to take off my clothes and sit completely naked with him for a while. He kept his clothes on while we sat on the couch. His hand exploring my body and making me feel really good.

Seemed strange to be sitting with a guy feeling my naked body, and he has all his clothes on. But I wasn't self-conscious. Which surprised me. From our talks before, he was aware that I was hardly a -pack abs type, and my five inches wasn't going split anyone in two. But he kept reassuring that he didn't care about any of that. He just wanted relax and feel comfortable with him. And I did, which surprised .

We stayed downstairs for about 20 minutes, talking about sex as he slowly played with my body. I felt relaxed and somewhat vulnerable, being completely naked while he was fully clothed. I had yet see his cock, and I really wanted ! He asked if I wanted go his bedroom, which I quickly agreed. Then he told leave my clothes downstairs. Which was odd, but maybe he just liked my nude body. Which would have been even more odd...

He took my upstairs, following behind while he gave directions his bedroom. With a pit stop in the kitchen for a refill my drink. I figured he stayed behind so could watch my ass as I walked the stairs. That was how I reasoned it in my head, but I didn't know how he felt about and my body.

Once in his bedroom, he had lay down his bed. He stood next to and undressed. I stared intently as his pants came down. He wore tight bikini briefs that hugged his bulge, a long cock made a clear outline in his underwear. When they came off, I finally got see in person what I'd only seen in a couple of low res photos he'd sent AOL. It was impressive even soft.

He took off his clothes and layed next his bed. I reached over and took his cock in my hand, feeling it get hard as I gripped it. We laid there for a few minutes, talking and stroking each other. It had been several years since I felt a cock that wasn't mine, and I loved gently pulling it. From our online chats, he knew that I'd never sucked one before and asked if I wanted try his. I agreed and he straddled my chest with his cock at my mouth. I leaned in and took it inside.

I'll never forget the taste of his hot flesh in my mouth. It was difficult to take much of it, but before long I was able to develop a rhythm of sucking and rolling my tongue around the tip, as it went in and out of my mouth. I was slightly alarmed when I tasted my first precum. When that slightly salty flavor my tongue, I wanted more. But he pulled his cock out of my mouth, turned around and started sucking again.

Now his ass was my chest, and I started rub his cheeks and tentatively and down his ass crack. I didn't even notice the bowjob I was receiving once I saw his buttholepucking in front of . I pressed a finger it and he opened right and it slipped inside. I had now sucked my first cock and was now fingering another man's ass. I got a tad overzealous and he jumped and asked slow down and take it easy.

Problem being, I was already too worked . After he moved off my chest and back down between my legs, he kept sucking , but started finger my hole and that sent over the edge. I shot a huge load onto my chest. This also got his going because he kneeled over , jerking his cock fast and shot his load my cock and stomach. He retreated to the bathroom and brought a towel. But I suddenly felt like I had to leave. As much as I wanted to stick around for more, I suddenly needed to leave.

After I left I felt a huge amount of conflicted feelings. I freaked myself out over what I had done and what it meant. Then in a stupid move, I stopped talking to him for five months. Basically ghosting him because I couldn't handle my feelings. After I gained some courage, I apologized and we talked it out. He told me it was okay. "You came so quick and then left..." We never did meet back up again as I moved out of state. So I didn't get to do the two things I really wanted with him.

I would about 2 years later. I met a guy online and he came to my apartment one morning. During our rushed session, he licked and tongued my butthole like I'd always wanted, and let me cum inside his ass without a condom. I was happy I got to enjoy those things, but really wish it would have been with the guy I met.

The guy who made me a couple nice Jack and Cokes, and let me cross off a few firsts I'd highly anticipated.

Would love to spend another night with him!

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