WelldressedBear – check him out on Squirt.org!

A quick bio – I’ve been bi for as long as I can remember. I love sex with men and women. When I was younger, I was a fit wrestler – six-one, 190-ish, with a six-inch, cut cock. My previous Cocktale was my intro to sex with men. This story happened the summer after my first experience when I was 19. I had put on about 15 lbs. of muscle from the previous year and was quite hairy.

As previously mentioned, my single mom had many gay friends, men whom I often fantasized about. Two guys she was very close with were a mid-40s couple who lived in a neighbouring town where my grandparents resided.

Growing up, we would often visit this couple at their home. They had a large, in-ground pool, which we had an open invitation to use. Swimming with them and seeing them in their sparse swim shorts – especially Paul – always turned me on. Paul was slightly shorter than me, Italian, with fur all over, a bushy moustache, and a thin but muscular bicycling body. The swim shorts he would wear when we visited left nothing to the imagination. I jacked off all the time, thinking about his cock outline and hairy pecs. I loved visiting Paul but never thought of him as more than a fantasy and respected his long-term relationship with his bearish partner. However, our family had fallen out of touch with the duo since going to college, and we hadn’t been swimming there in several years.

Fast forward to a hot summer day while visiting my grandparents. I was doing yard work in their front yard when I spied a familiar figure on a ten-speed, riding by in a form-fitting, one-piece biker Speedo.

“Paul!” I called out as he got closer.

At first glance, I could tell he did not recognize me, and he stared, puzzled, as he flew past. A couple of hundred feet later, with a shake of his head, he made a U-turn and returned.

As he pulled up in front of me, I couldn’t help but stare at the unzipped onesie and its trail to that familiar bulge. Immediately, I could feel my cock firming up as I relived those old fantasies. But I played it cool and sat on my grandparents’ porch as he rode up the short driveway.

“Man, I did not recognize you at first! You’ve filled out a bit since we last saw each other,” he remarked, with little effort to conceal looking me up and down. That look did little to calm what was going on down below, and I struggled to keep things from becoming obvious. It didn’t help that I was wearing light grey sweat-shorts and sneakers.

We talked for several minutes about life since our last visit. He shared that he and his partner were no longer together. While certainly sorry to hear this, as I liked the guy, I also felt there was some opportunity here. As the conversation started wrapping up, I reminisced about the pool and the summer days I had spent in it at his invitation. He took the bait.

“Hey, the invitation is still open! Looks like you have put in some hard work today. Come over when you are ready, and cool off. It will be like old times,” he suggested. Being the polite person I am, I readily accepted, and we made plans for later in the afternoon. I watched his tight ass ride off and scrambled to finish my work.

Around mid-afternoon, I made my way to Paul’s house, dressed in my swim trunks and a t-shirt, showing off the work I had been putting in at the gym. He answered the door in a short-sleeved button-down, completely unbuttoned, and thigh-high swim shorts. We made small talk again as we went to the fenced-in backyard and pool.

“Jump in,” he offered. “I went in after my ride, and I am going to lay out and get some sun.” He stripped off his shirt, and the problem in my shorts resurfaced. He was still slightly damp, chiselled in all the right places, and his abs pointed my eyes to that beautiful package. I jumped in immediately to “cool” things off.

As I did laps around the pool, I could feel Paul’s eyes on me, following me as I swam. At first, I was nervous, given our years-long friendship, but as I relaxed, I started to give him a show. I would sit on the shallow-end ledge and sun myself, jump in and float on my back, swim a bit, then sun myself again.

After about 15 minutes, I glanced over to see Paul gently tracing the outline of a hardening cock through his shorts, eyes completely on me. Feeling bold, I swam to where he was sunning himself and stared back.

“Looks like you need to cool off again,” I cheekily suggested. “Why don’t we enjoy this pool together, like old times?” Paul nodded his assent and jumped in.

Like a cat and mouse, we swam opposite each other at first. Paul shallow, me deep, then the reverse. As the minutes wore on and my lust grew, I stopped in the shallow end and waited for Paul to swim up. Facing away from him, resting my arms and chin on the ledge, and kneeling, I felt the water pressure on my back as he swam up behind me.

“I can’t cool off,” he whispered in my ear as he knelt with his legs on either side of mine.

“What can I do to help?” I mouthed as his lips found my neck. He pressed into me, ran his tongue from my neck to my ear, and then back down.

I grabbed his head to keep him there and felt his hard cock press up against my back. On his swim up, the shorts had disappeared. As he continued to kiss me, his hands found my sides and worked their way down to my trunks and into them. Kneading the lobes of my ass, he kept grinding into me and tonguing my shoulders.

“Turn around,” he urgently said. I eagerly complied to find him standing now. Facing me was an amazing eight-inch specimen. Cut, thin, with a full bush and big-ass balls. He stepped towards me, and my lips parted hungrily to take him in.

Paul was horny as hell, and it wasn’t long before he was pumping that meat in at a rapid pace. While gentle, his balls and the pool water were splashing with each thrust. I knew the drill and took that dick as he gave it. It wasn’t long before he announced that he was going to cum. I grabbed his hips and held him there as he came in loads, so much that it leaked into the pool.

As he finished, he slid back into the pool before me and moved in for a kiss. I readily shared his load back with him as his hands again found the waistband of my swim shorts. I was rock-hard from what just happened and stood up to help him pull them down. My dick slapped his chin as it was released. He pushed me to the ledge of the pool and spread my legs.

“Fuck, that is just what I have been imagining all day,” and he dove in on my cock without further comment. Friends in school in the past had sucked me, but this was different. This man knew what he was doing.

Grabbing the base of my dick, he pulled the skin tight and licked from my taint to the tip. Slow, with heavy suction at first. I was in heaven. When I thought it couldn’t get better, he picked up the pace and jacked me in rhythm. Again, the pool water rocked as I bucked my hips to his talented mouth. Like Paul, it was not long before I had to cum. The excitement of the moment, and his expert work, had me on the verge quickly. He knew it too and buried my dick in his mouth, to the balls. I came loudly and as hard as I ever had, not caring if neighbours heard.

As my orgasm subsided, I sank into the pool, and he pulled me in for another kiss. Despite the cool water, we were both sweaty and spent. We floated together for a while to come down from the high.

This was my first experience with a real man who helped me get off. In return, and for the rest of the summer before school, we often “swam” together to cool off. This was also the first guy to fuck me, but that is a story for another time. Hope you enjoyed this one.