I thought about doing this for a long time, but it took almost 25 years for it to actually happen. I was roughly 23 when "The Incident" with my best friend happened in college. I always thought that if I had reacted differently, my life might have played out in a very different way. For 25 years, I've wondered what would've happened if I had done something just a little different than what I did.
I was a student at a large southern university. I lived in an apartment near the campus, and my best friend lived off campus with his sister. Sometimes we hung out at my apartment, but at that time, my roommate had a girlfriend who was there all the time. So we went to my friend's place.
One night, we stayed up laughing, talking, and maybe drinking a little, and I slept over. I slept in his bed, and he was on the extra mattress on the floor of his bedroom. It was light outside, and I was in that lazy state before getting up. Not really asleep and not really awake. I was lying on my stomach, facing the wall, when I felt something touch my butt. I was wearing boxers and a t-shirt, and only covered by a sheet, so it wasn't difficult to feel it through the sheet. I shifted around and tried to get away from whatever it was. It happened again. Something was touching my ass.
Still facing the wall, I shifted again. When it happened again, that something was under the covers and felt a little more like an actual hand. The hand was shaking a little as it gently rubbed my ass. It didn't feel bad, but I still didn't know what or who it was, and I was scared to look!
The hand went away again. It returned a few seconds later though, snaking its way underneath my body to touch my early morning hard-on. Shaking again, the hand stroked it for just a few seconds, and then disappeared again. I surprised myself by lifting my weight slightly to let the hand touch my cock.
When it went away, the next sound I heard was the unmistakable sound of a man jacking off. At that point, I knew it had to be my friend. I had heard rumors about him and another friend – people saying that they were both gay – but I didn't know for sure. Now I did. Someone had even told me that he had a big crush on me. Of course I didn't believe them, though. We were just buddies, and nothing more.
But lying there in his bed, hearing him jacking off while kneeling on the floor next to the bed, I now knew that he wanted more out of our relationship. I had fantasized about sex with a guy before, but the opportunity never presented itself. I was exposed to porn early in life and was fascinated by pictures of cross-dressing men. I was intrigued by the big dicks sticking out from under the garter belts and lingerie, but never equated that interest with big dicks attached to regular guys.
To make a long story short, I got out of bed and almost ran out of my friend's house while he was in the shower. I graduated shortly after and we never spoke of what happened. Needless to say, things were a little weird between us the next time I saw him. He moved up north and I got married and had a family in a city close to the university we attended. We are "friends" on Facebook now, but that's about it. I haven't seen him in person in more than 20 years. But I still wonder what would've happened if instead of shifting away from his hand, I had turned over and given him easier access to my cock. But I guess I won't ever know.
Lately, I've been having those fantasies again. A couple of weeks ago, frustrated with the lack of romantic contact in my house, I decided to check out the personal ad postings on Craigslist. I have done this in the past, and responded to a few, but nothing ever materialized. Usually I chickened out, or the other guy just never contacted me back. I would usually end up just jacking off and moving on. But this time felt different. I decided that I was tired of wondering "what if," so I wasn't going to sabotage my desire for contact by jacking off. I would look for someone by answering ads, and see what came of it.
But then the guys I was responding to didn't respond back. Well, actually, one or two did, but then it didn't go anywhere. Damn. This was maddening. Didn't any of these guys want to actually do anything?? I was planning on going through with it, and no one would respond! Why do they place ads if they're going to chicken out??
I finally found one guy a little older than me. We met at a coffee shop and talked. He was not exactly my type – a middle-aged gay man with some very stereotypical mannerisms. He was very nice and encouraging to me in my exploratory mission, but we didn't contact each other again after that meeting. I think he was probably interested in me, but could sense that I was not really into him.
When that didn't work out, I placed my own ad. I got plenty of response. The first one I set up a meeting with was a 30-year-old guy who lived alone in some nearby apartments. He was very enthusiastic in his e-mails, saying that he was, "very very oral," but when I went to his apartment, he told me that he just couldn't go through with it. He apologized and I left. Again, more frustration.
So I re-posted my ad with more pictures. I finally got a response from a guy that was my age and in a similar family situation. He said he would like to meet, and had a private place. We set up a meeting for the next day. It turned out he was a realtor, and we met in an empty property he had listed.
I was happy when he sent me his picture that he was a nice-looking guy – a little bigger and taller than me, and he told me his cock was 7" and cut. That sounded good to me, although I didn't know for sure if I would go through with anything either. Boy, was I about to be surprised.
I arrived at the meeting place first and sat in my car to wait for him. When he arrived, I was pleasantly surprised. He really seemed like a nice guy, was very handsome, and a little bigger than me, which I liked. I'm 5-8 and about 155, so I'm not all that big, and I've always thought that with a guy, I would probably be a bit on the submissive side.
So, we went in and he asked me some questions about what I had done with a guy. It was weird to answer those questions out loud, because some of those things I've never told anyone. He was surprised that I had never done anything, and asked if I was sure I was ready. I wasn't sure what to say. "Come with me," he said, and started down the hall toward the bedroom.
The place was not lived in, so there was no furniture in the bedroom, but the blinds were closed. Very private. He asked me to sit on the floor next to him, against the wall. We talked just a little more, then I guess he decided to make a move. "Let's just make sure you are comfortable," he said gently, and placed his hand on my thigh. My heart was beating a hundred miles an hour! I said something, but I don't remember what, because right after that, he kissed my neck. His stubbly goatee was scratchy on my neck, and I liked it. I started to move with him, shifting to give him access to kiss my neck and ear. I could feel his breath on my neck. "Do you like that?" he asked as he continued on my neck.
"Umm...yeahhh..." I managed to get out, right before I turned my head, maneuvering around to return his kiss. "OMG. I am kissing a man!" I thought wildly. I literally couldn't believe what was happening. Couldn't believe I had the balls to do this!
We kissed, and kissed, and kissed some more. His tongue pushed into my mouth, and I returned the favor. My friend was emboldened by my lack of resistance to his kiss. I wasn't resisting, but instead was urging him on!
When he started unbuttoning his shirt, I started unbuttoning mine. Soon we were both shirtless, and he was lying on top of me as we kissed. I loved his weight on top of me, and the smell and feel of his body. This was unbelievable. Before I knew it, he was undoing his pants, so I began unbuckling my belt. Soon, we were both naked on the floor. This was fucking incredible. I was now naked with another guy and we were locked together on the floor in a very private place, with nothing but time. I was like a man possessed.
He talked a little during that time, asking how I felt, and telling me how good I felt on him. I felt his long cock rubbing against mine and against my stomach. I had to reach down to feel it – my first ever touch of another man's hard cock. It was hot. So nice in my hand. I felt its weight, heat, and ran my hand up and down its length. He did not exaggerate. It was seven inches, no doubt. A nice shape and length, but now I wanted more! I had waited so long for that touch, and now I was about to take full advantage of my opportunity.
I began rolling over to position myself on top. We were still kissing as I slid on top of him, feeling his cock against mine. Here was the moment I had been waiting for...I was about to taste my first cock.
I sucked on each of his nipples. While I sucked on one, I twisted the other in my fingers. I felt like a fucking porn star. I was doing the things I had watched countless times in movies. I kissed my way down his belly and smelled his scent. Then, still on the floor, I moved down between his legs and took his cock in my hand. I held it and kissed all around it, licking his balls and around the base of his cock. Then I put my mouth over it and took it almost all the way in!
It was fantastic. The most erotic, naughty thing I have ever done. As good as or better than eating pussy! I took to it like I was starving, wetting my lips and sliding them up and down his long shaft. I sucked hard on the head and he moaned loudly, before I slid my lips down his shaft again, taking it all the way in this time. I had the whole of his seven inches in my throat and felt like a total slut. Then I heard him say, "Let me taste that dick, baby," and he shifted his body around so we could position ourselves in a sixty-nine. Unbelievable. I was on fire!
Soon I was on top of him with his long, wet cock down my throat again, and I felt his tongue on my cock. He took it all the way down his throat and I moved my hips with his sucking motion, all the while slurping on his hard cock. His dick tasted so good. I used my hand on his shaft as I sucked faster. He pulled back a little, and said, "Don't make me cum yet, baby," so I let him slip out of my mouth, and we took a breather. I rolled over on my back, and pushed him so he straddled my chest, facing me. I wanted him to feed me his cock, and wanted to lick and suck on his balls, too.
I sucked on the head of his cock more, like I did before, which elicited more moans from my partner. I lifted my head, and he fucked my face slowly with his cock. I was loving it. I closed my eyes and let my lips slide up and down his shaft as he fucked my wet mouth. "Yeahhhh...suck my dick, baby," I heard from above. Cock sucking suited me well.
After a couple of minutes of this, he turned his body around to face my feet and we began sixty-nine in earnest again. But this time, he urged me to lift up slightly, because he wanted to lick my ass. OMG. Un-fucking-believable. Soon I felt his mouth on my balls, and then he licked his way down to my asshole. Holy crap, it felt so fantastic. So nasty. I was a total slut. What I wanted at that point was for him to fuck me, and fuck me good. I had waited a long time for this!
While he licked and sucked my asshole, which was amazing, I had his long shaft all the way down my throat, and it stayed there as I moaned around it. I tried to move my head to get it out, but I was trapped in that position – legs up, his mouth on my ass, and a long, hard cock down my throat. Not a bad place to be!
When I had to have air, I moved my head hard to one side and his dick slipped out of my mouth. He lifted off me and turned around, lying on top of me again, with our cocks rubbing together. I reached down and held both of them together, stroking both of them at the same time. We rubbed them like that for a minute or two, and then he shifted his weight a bit. I thought he was wanting to fuck me, and I wanted him to, so I said breathlessly, "Do you have a condom?"
He replied, "Oh, I'm not going to fuck you, today. I want you to come back to me, baby." While this did not make me happy right then, it did give me something to look forward to. But then he said, "I might let you fuck me, though." I told him not today, because I wanted to use a condom. So we went back to work.
He laid back down on top of me and we continued the making out. I reached down and rubbed our cocks together again, which I loved. The feel of his hard cock rubbing up against my own was so hot. We lay on our sides kissing again, as I used one hand to rub the length of our shaft together, jacking us both off.
He finally decided he wanted to suck my dick again, so he straddled my chest and turned around to get us in a sixty-nine position. From there, I had his nice, long dick hanging in my face. Too good to be true. I lifted my head and took it back into my mouth, making plenty of wet noises with my lips and tongue, and moaning as the position I was in drove his cock further down my throat. I was pinned there with his dick all the way down my throat. So fucking hot.
Meanwhile, he was going to town on my cock, sucking faster and faster, taking it all in his mouth. He was great at his job. I was getting close to an enormous orgasm, and I let him know. "I'm about to cummm..." I managed to get out around his cock, and then it hit. Huge cum.
My cock began exploding in his mouth. I don't know how many jets of cum I shot, but that cum felt like it lasted 10 minutes! He took it all in his mouth, too. After I came, he laid back and I stroked his cock until he shot his load, which I watched with fascination. He shot a huge load, all over his stomach. I felt his cock jerk in my hand as his cum arced up, spattering onto his belly. Now we were both spent.
When I showed up to meet him about an hour before, I didn't expect to leave with the taste of cock still in my mouth! But that's what happened.
We dressed and got ready to leave, and made a tentative plan to contact each other later. Later, he e-mailed, telling me it was nice to meet me and that he wanted to get together again soon. I seconded everything he said, and told him there were a couple more things I wanted to try, so I wasn't ready to quit yet!
As of today, we are planning to get together next week. I plan on taking condoms, for me and for him. And probably some lube.