Just after my 23rd birthday I finally decided to follow through with a Grindr hookup. For the past few years I had added the app, chatted with guys, and eventually deleted it without meeting anyone, mainly out of fear, shame, and questioning my sexuality. But then I met Shane.
One evening in October I found myself chatting with a rugged 45-year-old businessman. He seemed to live a hippie lifestyle. He had numerous pics with plants, outdoors, in just his briefs, etc. Long hair and short, black beard. As someone who mainly finds men closer to my age to be my preference, I was oddly drawn to his profile. I soon found myself chatting with a Dominant personality. As a submissive myself, it came naturally and I continued to be drawn to him. After a few messages it was time to exchange nudes and when he sent his pics I was hooked. As a submissive bottom with rather average manhood of 5.5", my special asset is my thicker than average bubble butt. That is my main tool for attracting men with my nudes. Shane was no different. After showing myself off to him, he replied back with a set of nudes still imprinted into my mind to this day.
I suddenly found myself salivating at image after image of an absolutely perfect cock. A soda can thick, uncut, 8" tool. I just knew I had to follow through and let him take me. We continued chatting and sharing pics, and the messages got naughtier and naughtier. I found out he lived in the woods in a cabin on 60 acres at the base of a mountain. It was a secluded area and I knew he would protect my privacy. I had mentioned before that he was a businessman. His prominent local establishment reassured me that I would be safe with him. He was enough of a public figure that I knew he wouldn't risk anything on his end, making me feel more comfortable with meeting.
After a couple days of chatting, it was a cool Sunday evening in mid-October. It was the perfect evening. It was time to meet him. His house was about 25 minutes away so I set off and arrived about 5:00 pm. Shane greeted me in the driveway with a calm, determined personality. He wore a T-shirt and baggy jeans, and was very gracious as I nervously greeted him. He was watching Rick & Morty as we sat down on the couch and made idle chit-chat. Within two minutes, his body pressed against mine and his hands began to explore me. I wanted to reciprocate but with my inexperience, I hesitated. "It's okay, go ahead and touch it," he said calmly as I began slowly massaging the growing shaft through his jeans. As we continued touching and feeling each other, his hands gradually found my ass. After a few strong squeezes, *wham*. A firm smack on my right cheek made my libido increase and inhibitions begin to melt away. He suggested a better place to get to know each other, so we proceeded out the back door and about 50 yards through the woods to a smaller cabin.
Arriving at the cabin, I was immediately led up the stairs to the second floor where a bed was ready and waiting. Lube on the nightstand, I knew this was the bed he'd fucked countless asses previously. When I told him where I was from in conversation, he asked me if I knew Thomas Dunn. I replied that I knew who he was, as we'd gone to high school together. Thomas was a year younger than me and had obviously come to terms with his sexuality at a much younger age than I had. I'm sure by the time he was 18, he was getting pounded regularly, and Shane confirmed that Thomas was a frequent visitor to his cabin. He had apparently recently gotten a boyfriend his age and had stopped coming over. Thomas was the token twink, about 5'6 with shoulder-length hair, no body hair, an ear stud, and always in the middle of a group of giggly girls. He's the type of bottom that would almost make me wanna top. It came as little surprise that he had matured into getting dicked down on the regular.
Shane laid me back on the bed and made sure I was comfortable. He removed his shirt and began massaging and eventually kissing my neck and shoulders. He knew I was brand new to this and slowly and patiently guided me toward his end goal. I wanted him to take the lead, to feel his Dominance over me. I needed to be submissive in that instance, to ensure that his needs were satisfied. l of course knew that I wouldn't be his best, but I just tried to focus on exploring the sensations and enjoying the experience.
Shane raised up and took his shirt off, telling me to remove mine as well. I removed my long sleeve shirt but just slid my pants and briefs below my ass. Upon seeing my stiffening cock for the first time, he forcefully exclaimed, "I said OFF!" My pants, briefs, and socks came off and hit the floor beside the bed within five seconds. After touching my now fully erect protrusion, he slid his hand slowly up and down the shaft a few times before getting back on top, our bare chests quickly becoming acquainted. He continued kissing my neck and chest, and my hands found his back. Delivering light scratches, I seemed to have flipped a switch in him and he abruptly got off the bed and stood beside it. Motioning me over, I took the hint to undo his button and zipper. Inside, I found no briefs but instead was greeted by an absolutely massive package. His cock looked even better in person, and I don't think saying his balls were each twice as big as mine is even remotely an exaggeration. I, still standing, grabbed the massive shaft and started moving back and forth at the head.
I expected to be forced down told to service him but instead was thrown back onto the bed and flipped onto my stomach. Shane then delivered 5 hard slaps to each cheek. I had mentioned during our chats over the previous couple days that I was into exploring BDSM to an extent, and that I wanted to be spanked. He came through on that wholeheartedly. Turning me back over he repositioned us into the spot from moments before, this time our naked bodies grinding together and his lips exploring my face. Within 30 seconds, my fingers dug into his back and my feet wrapped around his ass. I clung tightly to him, needing to feel his body against mine. He asked if I had kissed a man before and when I said no, he looked knowingly into my eyes. I knew this was the day, and I shut my eyes and weakly puckered. I was met with a deeply sensual kiss lasting at least 20 seconds.
As we broke the kiss, we looked into each other's eyes once again before I grabbed the back of his neck and brought him into a wet and sloppy makeout session that continued for at least five minutes. I was all in tonight and wanted everything he had to offer.
I soon found myself in the position I had anticipated, kneeling before him, his cock in hand. He leaned against a wall beside the bed as I slowly but steadily became acquainted with the massive third leg hanging before me. After a couple minutes of stroking, I slide the foreskin back and took him into my mouth. It was a little musky and honestly not the best taste at all, but I couldn't break away. I began sucking the head and trying to lick the frenulum underneath. He reacted positively and began forcing my head lower and lower onto him. After maybe 15 minutes, his shaft was buried at least halfway into my mouth, while my hand serviced the remaining half. My saliva kept the entire length lubed as I worked at pleasuring his wonderful tool. My old, questioning self would have shied away from sucking a cock, thinking about how many guys' assholes that thing had been buried in. But on this evening, all that mattered to me was that he felt as much pleasure as my body could give him. My jaw began hurting and he sensed it, so we returned to the bed and made out a little more. Finally grabbing the bottle of lube, he applied a generous amount to both our cocks and we began stroking each other's shafts as we kissed. After a few minutes, he told me to lay back and hold my feet back in the air. I did as he requested and found my knees up by my shoulders, my shaved boyhole fully exposed.
After a brief rimjob, he inserted a lubed finger into my ass while continuing to stroke my little erect shaft with the other. By this time, I was hard as a rock as he began to focus on my pleasure. He soon found my prostate and began pleasuring my inner and outer parts in perfect unison. I could tell this definitely wasn't his first rodeo, he probably did this to all the boys. I relaxed in sheer pleasure as his finger rubbed my spot just perfectly and the other slowly but steadily serviced the shaft. It was clear I was being coaxed to provide my sperm, and I was in ecstasy during this inaugural milking. After about 10 minutes his pace picked up dramatically as I began to spasm and moan with pleasure. My eyes rolled back as I moaned, "I'm cumminggggg" and proceeded to shoot my first three cum shots over my head onto the wall behind the bed. Never, ever had I shot a load that far. By the end, it was probably the biggest load my little balls had ever produced, and I was soaked in so much cum, Shane had to get a towel to clean me off. When I get super horny, I enter a different headspace, and even a massive orgasm like that doesn't finish me off. This was one of those cases, and after just a couple minutes, I was ready to go again. Of course, Shane was incredibly backed up and needed to drop a massive load himself, so he reached into the nightstand and produced a Trojan Magnum. Sliding it onto his bulging, throbbing cock, he generously lubed both his sword and his intended holster.
