In the mid-1990s I decided to try meeting guys using AOL’s Men4Men Discussion Chat and Bulletin Board. It was a new medium, and it held promise by allowing one to be anonymous and get to know someone before actually meeting in-person and getting to “know them biblically." For the most part, these encounters left much to be desired. Eventually, the internet would offer far better hook-up websites and apps, some of which I have used, but at first there just wasn’t any option other than the Bulletin Boards and chat rooms. I crafted the following post (which I found in my old email files) for AOL’s Men4Men Bulletin Board.
GWM, 32yo, 6’1, football player’s body, hairy-bear, vers/top, iso GWM, 18-30yo, <6’, slender, smooth, twink, btm or vers, for conversation, dinners out, movies, and intimate bb encounters in the Chicago area. You must be clean, ddf, have no serious hang-ups, be self-supporting, intelligent, educated, and have a good sense of humor. My faith is important to me, and you should be ok with that. Pref given to those interested in long-term relationships. Reply via aolBB this entry or e-mail: XXXXXXX
My post got a lot of responses. Some were trolling from outside the area, which made it very difficult but not impossible to meet them. Others were nearby but they were flaky even in their posted or emailed responses. One of my college friends (Ryan) saw my ad and responded with a very suggestive post that drew a lot of inquires of its own; we had a good laugh about that … and, of course, I fucked him for it.
The first “real” response I got was from a guy who went by the AOL screen name of DavidX. We talked for several days in the M4M group chat, then set up a date via email. He was nice, interesting to talk with, and appeared to be acceptable as a possible sexual partner if not as a boyfriend. He wasn’t particularly attractive in the face, but on the other hand he also wasn’t ugly. We had a lite meal at a restaurant and then went back to my place and started making out. That went ok, though he was clearly very nervous … more so than I had anticipated. After about an hour of making out and watching some TV (which seemed like a long time to me), I started to rub his back and explore his body by touch. He kept getting fidgety, and at one point he stood up and stepped away from the couch.
I asked him if something was wrong, and he admitted that he had never done anything like this before. I told him that it was ok, and we could take it more slowly, so he sat back down, I put an arm around his shoulders, and we watched some more TV. After a bit, during which I suppose he was trying to get his courage up, he suddenly turned to me and asked: “can I see you without your clothes on?” To be honest, I was a bit surprised by the request. However, not being overly shy, I stood up and took off my shirt. I then dropped my pants and stood before him wearing only my underwear. David sat and looked at me for a minute or so, quietly exploring me with his eyes. While he looked, I started to feel my cock get hard, and I let it tent my underwear, pulling the top of my underwear away from my lower abdomen. David’s eyes were drawn to that, and I watched as he absent-mindedly reached down to touch his own dick through his pants.
Being examined like this was, strangely, very exciting. I guess David was calmed down enough after seeing me like that, for he finally stood again and took off his own shirt and dropped his jeans. I liked what I saw: he was, indeed, very slender, had a hairless, wiry, thinly muscled body with narrow hips and shoulders … physically, he was attractive in many of the ways that I like. He was about 5’11” and, by my guess, must have weighed about 115 pounds. He had told me that was he was 22 years old, and based on his appearance I mostly believed it … although I suspected at the time that he might actually be a little older than that, he was certainly younger than me.
I stepped over to him, put my arms around him, and cuddled him; I then kissed him, and he sighed and relaxed into my arms. After a minute or so of this, I proceeded to maneuver him slowly down the hallway and into my bedroom. When we got here, he stopped me with hands on my chest and asked, “what are we about to do?” I told him that we weren’t going to do anything that he didn’t want to do, but that I was in hopes I could make love to him and make him feel very good. With that he began trembling quite uncontrollably. I pulled down the sheets on the bed, laid him in the middle of it, got in next to him, and pulled the sheets up over us; I then proceeded to cuddle and kiss him again. He began crying gently, and when I asked him what was wrong, he admitted that he had never done anything like this before and that he was scared. I told him that we didn’t have to do anything, if he didn’t want to, and he said he understood and thanked me for that. After a little while, his trembling subsided to the point that I could start caressing his body more explicitly, enjoying the feel of his flat chest, his skinny tummy, his sides, his protruding hip-bones, and his crotch. Even though he was clearly frightened, nevertheless he had sprung a boner, tenting his underwear; I asked him if I could remove his shorts and he said “yes.” I did, and removed mine as well, and then I got up and settled my body down on top of his, holding myself up by my knees and elbows as I kissed him and put a bit more weight on him to further comfort him. It worked, and within 10 minutes we were making out passionately and excitedly. As we made out, I positioned my cock in the ridge of the cum gutter that ran from his left hip down to his crotch, and slowly began to hump. The precum was already flowing heavily out of my cock, and so as I frotted against him I was also lubing the path for my dick. His penis was also raging hard and leaking precum, smearing onto my stomach as I pumped against him. This went on for a short period of time, while he whimpered and wiggled underneath me and also stroked my back and arms and sides with trembling hands.
After a while I lifted myself up, encouraged him to roll over, and then I settled myself down on his back with my cock pressed against the bottom of his spine. I then kissed my way down his back from between his shoulder blades to his soft ass. When I got there, I gently worked my hands in between his cheeks and was touching his hole when he became very ridged. “What are you doing?” he asked. I told him that I was getting ready to prepare his hole to be fucked. He lay there, quietly, for a moment, and began to tremble slightly. Eventually, however, he said with a halting voice: “ok. but, please, don’t hurt me.” I kissed both of his ass-cheeks and said, “Don’t worry, you’re going to love this.” I then spread his cheeks wide and noticed how nice and clean he was … he didn’t have any hair in his crack and his hole was pink, fresh, and tiny. I leaned in and allowed my tongue to slather up and across his hole. It twitched, and he yelped. “Did you just lick my asshole?”
“Yes,” I said. And then I did it again, lingering longer on his tight opening. He gasped, moaned, and arched his back slightly while I continued to slather his ass with my tongue. As I licked, I allowed the tip of my tongue to probe ever more deeply into his tiny hole, and David’s whimpering became louder. After several minutes of this, his hole began to relax, and it actually opened some, allowing me to tongue deeper into him. At one point I paused, worked up a large glob of spit in my mouth, and then allowed it to ooze into his hole; I watched as it pooled there for a moment, then as his hole opened, it drained into him. My heart nearly stopped … that was so incredibly sexy, I just couldn’t wait any longer to fuck this virgin! I reached over to the nightstand, got the bottle of lube, and poured some onto his hole and watched as that also drained down into his ass. I then applied some to my hand and began to work my fingers into him. David didn’t protest, but moaned even louder, arched his back, pushed his butt toward me, and first one, then two, and finally three fingers sank into his ass. After 5 or so minutes of gentle probing, he seemed to be really getting into it; I kept asking him how he was doing, and he gasped out that it was wonderful.
When his hole was ready, and my cock was leaking pre-cum by the bucket load, I got up on my knees, flipped him over onto his back, and settled between his legs; I put a pillow beneath his hips, draped his legs over my shoulders, rested my cock against his taint between his balls and his hole “Are you ready?” I asked. He admitted to being very afraid, but also very curious and willing to try. So, I started to push my cock’s mushroom-shaped head against his pucker and waited. His sphincter was very rigid, and it began spasming as I pressed against it. I reached down and petted his tummy, caressed his chest, and gently stroked his cock and balls, careful to make sure that he wasn’t close to cumming … something that I wasn’t too sure about because his dick was very hard, throbbing with his heartbeat, and had deepened to a darker shade of purple while I had been playing with his ass. This boy was ready to cum; more importantly, for me, he was ready to get fucked.
After a minute, I began applying a gentle bouncing pressure: first a bit more, then a bit less, then a bit more, then a bit less … with each time I applied the pressure, I increased it just a tiny bit more. I remember looking down and watching as my dick, looking enormous against his tiny hole and turning a deep shade of purple with my mounting excitement, began to disappear ever so slowly into his anus. This was incredible: my cock head is large and thick, and my dick is 6.5 inches around and 7.5 inches long: to be the first penis to penetrate this guy’s hole was going to be amazing for us both. It had been a long time since I’d fucked a virgin, but I remembered that it would take patience to get into his ass, and so I practiced patience. I eased back, allowing the head of my cock to pop out of his hole. I added more lube, then pressed in again and held my cock there, the ridge of its head finally vanishing inside his anus … where it stuck. I tried backing up, but the ridge of my cock’s head held me inside, so I pushed in more forcefully and, all of a sudden, I felt that wonderful SNAP of his sphincter giving way and my thick cock went plowing into his hole in two successive, increasingly deeper trusts. He was very tight and very hot and he cried out at the sensation of being breached. I paused for a moment, with my dick about half-way inside him, and waited for his spasming hole to calm down. I looked at his face … his mouth was open, his eyes were closed, and he appeared to be in utter shock at what was happening to him. But, he didn't protest or tell me to stop. I backed up a tiny bit, then leaned forward and allowed my cock to surge the rest of the way down into him until I tapped the back of his rectum. He was so close to cumming that, when I hit bottom, he couldn’t stop it … he blew a load high into the air and all over himself. I stayed still with my cock in his ass while I began to slowly work his creamy ejaculate into his skin. He apologized for cumming so quickly, and I told him not to worry about it, it happens to lots of guys the first time they’re breached.
I then straightened up, lifted his legs until they were over my shoulders again, and began fucking him. Yes, he lay back with his eyes closed and allowed me to fuck his tight ass immediately after his orgasm! His dick got hard again while I pounded his prostate, and he seemed to be enjoying it. While fucking him, I slowed down and allowed my hands to roam his body: his physique really was very attractive: he had an abdominal vacuous that beckoned to my touch, and I allowed my fingertips to trace the barely perceptible lines of his thin abs as well as the very sexy territory between his penis and his flat belly button. At one point, I allowed my hand to press down firmly in that magic spot and, yes, I could identify the hardness that was my cock, buried up inside him. I pushed my dick upward into him as deeply as I could and, as I looked down at him, I could faintly see the bulge that my fingers could easily discern; it was only the slightest of humps in the surface of his creamy-smooth skin, but it was definitely there, and when I would pull back with my dick, it would vanish. It was incredible.
David reached up to me as I fucked him and placed his hands on my chest. He ran his fingers through the fur he found there, and he traced the curve of my pecs around the underside, then up and over my nipples, which he fingered. “You’re a real man.” He gasped out as I kept fucking him. “A real man in my hole.” I smiled at him, leaned down, and kissed his lips. "Yes, I'm in your hole." I said, and he moaned as he put his hands up and around my shoulders, gripping hard against the muscles he found there while I continued pumping my dick into him very deeply. Each time I pushed all the way to the back of his rectum, he shuddered a little bit; for a moment, I thought of trying to go deeper, since perhaps a half inch of my cock remained outside his hole, but I feared that forcing myself into his colon might be too much for a virgin. Instead, I just kept fucking him, slowing down in order to prolong the experience for both of us.
About this time I noticed that his dick was leaking precut. Each time I pounded into him, a bit of cream came out, and was smearing into the fur on my stomach as his cock pressed against it. Yes, he was getting close to blowing again. His balls had even hiked up into the shooting position. I was glad ... he was really enjoying this. Well, so was I. The pressure to cum was mounting inexorably behind my cock, too, and I relaxed to allow it to happen without my having to push it. I knew I was going to nut hard, that it was going to be wonderful, and I wanted him know I was coming in him when it happened; I pulled back about half-way just as I felt my cock swell that last little bit, and then I felt that incredible rushing sensation down my back that signals a truly exceptional orgasm as I unloaded an enormous gusher into his rectum. I kneeled up straight, supporting myself with his legs, and looked down as the inches of my dick outside his hole spasmed with each pulse of my orgasm. Watching myself nut was so incredible, and I knew he could feel it because his moan of amazement, followed by his second orgasm triggers by the pressure of my cock on his prostate, was the best applause that he could have given me. Yes, I had initiated an anal virgin into the joys of fuckdom, and I was very pleased with myself!
When I was finished, and had pulled out and laid down on the bed beside him to try and catch my breath, David propped himself up on one elbow, looked me in the face, and asked matter-of-factly: “so, that’s how my wife feels when I fuck her pussy?”
I was polite with him, explained that vaginal intercourse certainly feels different to a woman, but that if he wanted to try fucking his wife in the ass, I was sure she would feel pretty much the same things that I had made him feel … other than the stimulation of the prostate, which she won’t get to feel because she doesn’t have one. Yes, I was mad at him … but I think I kept most of my irritation out of my voice.
I never saw him again. I never tried to contact him, and while he did email me a few times to ask about a re-match, I never responded to him. He had been a fun fuck, but I wish I’d known he was married. It bothered me that he was fucking around with guys and his wife didn’t know about it … or did she? I had been so peeved at him that I hadn’t bothered to ask. Perhaps I should have, and perhaps I could have had sex with him some more had I been willing to try; but, at the time I had other options available to me that didn’t involve someone potentially cheating on a spouse.
