Going All In

This is the story of a long time fantasy of mine that I finally had the courage and luck to see play out.

I'm happily married and love sucking and fucking my wife's beautiful bald pussy. However, for years I couldn't ignore my strong bi-curious urges that eventually led into the bookstore scene and a handful of experiences with men. Over the past couple of years, I'd managed to try just about everything once - giving and getting handjobs and blowjobs, getting my ass rimmed and fucked and all kinds of other quick and anonymous experiences. It was all very exciting and helped expand my sexual thinking and took sex at home to new places. I hadn't told my wife and didn't know how, but we were trying new and exciting things from relatively modest upbringings and our sex life seemed to be heading in a new direction.

About 6 months ago, I was away on business and found a nice adult store just a few blocks from my hotel. I hadn't been with any guys for about a year, so one night after dinner I wandered in and quickly found a large and busy arcade. I made eye contact with a few guys on my way to a booth, pulled up some porn and hopefully left my door unlocked. I sat down on the couch and my cock started to harden, so I unzipped my pants and started stroking. Within a few minutes a good looking black guy stepped in and wordlessly dropped his pants down and started stroking his dick. His dick started to grow and I realized that this was going to be the biggest dick I'd ever seen. As I reached for it, it filled my hand and I got down on my knees for a closer look. I began licking and kissing the head while slowly jacking the shaft and working it into my mouth. I went slow, building saliva and my rhythm. At 8 or 9 inches I could only get a few inches in my mouth, but I stroked the shaft as I sucked on what I could. After a few minutes, the guy started fucking my mouth and I could feel his cock bumping against the back of my throat. I'd swirl my tongue all over the shaft and head, while stroking the base as he pumped in and out. He started moaning and pumping faster, and I could feel his cock grow in my mouth. I knew he was close, so I sucked a little harder and jacked a little faster. Within a minute, that monster cock erupted in my mouth, blasting cum down my throat as fast as I could swallow, but quickly spilling around my lips and down my chin. The guy kept his cock in my mouth, still slowly stroking in and out as he softened. Without warning, he pulled out, zipped up and left. I barely had time to sit back down on the couch and start cleaning up, when another guy entered the booth, pulling out his fully erect cock. He must have been watching, as he mumbled something about how hot that was and he shoved his cock toward my still cum covered mouth. He too started fucking my mouth, so I reached up with my left hand and fondled and squeezed his balls. I was incredibly turned on too, so I stroked my now fully exposed cock. We were both too far gone to last long, and when he started blowing his load into my mouth, I let go too and exploded with my orgasm. As he relaxed, I licked and sucked the head of his dick, rubbing it all over my lips and chin. I completely cleaned him off, he thanked me and left.

I cleaned up and left a few minutes later. While this had been a fantastic experience, it was getting to be a bit of been there, done that. I didn't see how I could ever tell my wife about experiences like these, so I went back to my hotel room and pulled up my AFF profile. I realized I'd never done much with my profile or responded to any hits, and decided maybe it was time to go to the next level. That thought quickly developed into a full fantasy of a complete sexual encounter with another guy in a classy hotel. I had no interest in a relationship of any kind, but progressing beyond the anonymous encounters I'd come to know and doing something more intimate and complete seemed to be a good idea. I looked at my schedule and found a major city I'd be traveling to in a couple of weeks, changed my profile to reflect that location and started looking at profiles there. Within a couple of days, I started getting hits, I responded to a few and found a good looking guy to chat with. We traded emails, I explained that I was looking for a discreet encounter and we set a time and place to meet at the hotel I'd be staying at. My excitement level grew as the day came closer, I knew this was the right move.

We finally met at the hotel bar where I was staying on a Sunday night. Over a beer, we chatted about sports and the weather. I was a bit nervous, but mostly excited, and he finally suggested we go upstairs. As the elevator door closed and I pushed the button for my floor, he reached around and grabbed my crotch, giving it a firm squeeze and whispering how much he was going to enjoy this. I looked at him and agreed, grinding my crotch into his hand. The elevator finally made it to my floor, we quickly keyed into my room and it was on. I wasn't sure I wanted to be kissed by a guy, but when he grabbed me by the hips, pulled me close and started kissing my neck, I suddenly didn't care. We kissed and tongued each other, while backing towards the bed and dropping clothing along the way. By the time we got to the bed, we were both naked, standing face to face. I took his already hard cock in my hand and began slowly stroking it. He did the same to me and after a minute, I pulled him closer, slowly stroking our cocks together. Stroking and fondling our cockheads together felt amazing, and when he rolled his head back and began softly moaning, I took the opportunity to drop to my knees and inspect his tool. He had a beautiful 8 inch cock with clean shaven, large balls and just a small patch above the shaft. While still slowly stroking his shaft, I began lightly tonguing and sucking on his balls. When I started to kiss and lick the underside of his shaft, he got weak in the knees and sat down on the edge of the bed. I moved forward and slowly pumped and squeezed the head of his cock into my waiting mouth. I sucked on just the head for a few minutes, flicking my tongue up and down and all around, and enjoying his taste and feel. As I started sucking the shaft into my mouth, I'd slowly drag my tongue up the vein, taking my time to pick up the speed and pressure. When I started massaging his balls on the upstroke, I could tell he was losing control. I increased the speed again, his cock began to throb in my mouth and then erupted in orgasm. I swallowed it all like a champ as he slumped down on the bed, and I slowed down and licked him clean. I gently squeezed a few more drops off of his dick, and sexily licked and swirled those drops around his cockhead before taking him in my mouth one last time.

He said, "Wow! I don't know how going to top that." I leaned in and kissed him and told him he'd find a way and stood before him with my raging boner pointing straight at him. He sat up and reached for my cock, slowly jacking it while looking me in the eyes. He had a hungry look in his eyes, and I knew this was going to be good. He started by licking up and down both sides of my shaft, getting it good and wet while still stroking it. I too was getting weak in the knees, so he spun around and I sat down on the edge of the bed. He moved into position between my legs and in one motion swallowed my clean shaven cock whole. I gasped hard at that point and tried to stay sitting, but when he started working his tongue on my shaft as he was working his way back to the head, I fell back on the bed. He slowed way down and slowly, almost lazily, began sucking up and down on my dick. He'd fondle my balls while kissing and lightly working on the head, then lick and stroke the shaft. My head was spinning and when he began sucking faster and deeper, I started to lose control, moaning that I was about to come. Just as my orgasm hit and my first blast of cum erupted in his mouth, he pulled off my cock and quickly put his lips on the head, kissing and licking all around as my cum splashed on his lips and back down my shaft. He was far from done, as he was smearing my load all over my balls and eventually began kissing and licking his way down there. I assumed he was going to lick my balls clean, but he kept working my cum lower, his lips and tongue following until he started working a cum covered finger into my ass as he licked the bottom of my balls. Working my cum and his saliva into my ass, I knew what was coming next and incredibly I stayed hard.

I scooted up onto the bed and spread my legs as his anal probing loosened my asshole. He would alternate between rimming me and working a finger deeper into my ass and I began to relax as his lubrication had me ready. I could see that he had a raging hard on again, and I begged him to fuck me. He carefully moved up over me on the bed, straddling my head and bringing his cock back up to my mouth. I slathered it with my own saliva, sucking it into and out of my mouth as fast as I could. I whimpered when he pulled back, not because of what I just lost, but what I was about to get. I spread my legs and pulled my ass cheeks apart as he put his cockhead at my now slippery hole. He rubbed his dick up and down my crack and over my balls, and teased putting in just the tip. I was writhing and moaning with anticipation and finally he couldn't take it any longer and lined his dick up and slowly slid into me. I was relaxed and ready and took him all the way in to his balls. He stayed still for a minute to let get used to his size, and we passionately kissed and tongued each other. The taste of my cock and cum on him was hugely erotic, but I wanted to be fucked and slowly started rocking back against his hard on. He started doing the same, sliding his cock almost all the way out, then slowly back in. I was in complete ecstasy as his cock stretched wide and my own dick began twitching. He was a true cocksman, slowly building the tension and then back down, before building back up a faster each time. We both had a light sweat going and when I started squeezing my asshole around his cock on his downstrokes, he started losing control. He began plunging into me faster and faster, both of us moaning and groaning. I started stroking my own cock and within a minute I blew a huge load that hit his chin and splattered all over his chest and stomach. That set him off and his dick exploded deep inside of me, his cum coating my anal cavity. He collapsed on top of me as his cock spasmed and softened inside my ass. I kissed and licked my own cum off his chest and neck as we both came back down.

We were both speechless and quietly kissed and licked each other, but after a few minutes regained our composure and I suggested we take a shower. I was in a nicer hotel, so the shower was bigger and we continued this erotic encounter by showering together, lathering and cleaning each other off. While toweling off, we talked about how amazing that experience had been and that just got us both turned on again. We went back to the bed with growing hard ons, stroking each other to full erections. We rolled onto the bed and I climbed on top of him and we lazily sucked each other off in a sensual 69, something else that I'd never done before.