Hookup at the Wine Bar

I've been a secret bi bottom for about 15 years and I love it. I had long had curious urges towards men and I started all those years ago with anonymous Craigslist and adult bookstore encounters. It was scary and exciting but the sexual highs of playing out long time fantasies with strange cock and figuring out what I liked quickly had me hooked. Slowly taking a new cock past my lips and into my mouth, and feeling it pulse and throb with excitement as I bobbed up and down on it and coated it with my saliva before feeling it explode in orgasm down my throat often had me quivering in excitement. Rarely did I have to do more than touch myself for a few strokes before cumming back then.

Once I found my way in this world, my encounters got better and more meaningful. I've had some occasional blowjob regulars where working the same dick a few times was great. Knowing what a guy likes and being able to take my time getting there was empowering in a way that I hadn't expected bottoming to be. I like being submissive when I'm being fucked but being in control during a blowjob and having a guy beg me to blow a load in my mouth is a sexual high like nothing else.

About a year ago I'd found a local regular to do just that to. After half a dozen mind bending blow jobs at his place, he nervously progressed to giving me a handjob, then quickly moved on to sucking me off and fucking me with his beautiful cock. That unexpectedly progressed to sucking off one of his straight buddies and soon enough we were having threesomes where they would take turns filling my throat and ass with their cocks and cum that was some of the best sex we'd all ever had. In that we were all married, it was a bit difficult to get together, but mind blowing when we did.

To fill in the between times, I had occasionally turned to encounters on the road, where it all started for me. I travel a lot for work and upgrading an anonymous blow and go to something deeper, more involved and more intense had gotten pretty hot too. Earlier this summer I was in Seattle for work and stayed over for a day to play some golf and unwind. I didn't have any specific plans for a hookup, but after a shower and cleaning up in a nicer waterfront hotel, I ended up at a nearby wine bar. It was a pretty quiet Sunday night and I was sitting at the bar enjoying some small plates and a glass of wine and chatting with the bartender. After about 15 minutes, a good looking guy sat down 2 seats over and struck up a conversation about the wine and food. Like me he was dressed business casual and I correctly guessed that he traveled for work as well.

"I'm Rick, by the way," he introduced himself.

"I'm Jay," I said and we shook hands. He had larger hands and he seemed to hold my gaze for a moment and a little jolt of excitement shot through me. I couldn't believe my good luck but allowed myself to get interested and hopeful.

We hit it off and decided to share a bottle of wine and ordered some more food. The bartender opened the bottle and excused herself to start closing up, and Rick moved over to the bar seat next to me in what was now a nearly empty bar.

"I don't want to get too close, it'll just be easier to enjoy this," he said with a hint of playfulness.

"Get as close as you like, I don't mind," and gave him a wink.

That definitely caught his attention, and I knew we were onto to something. We started talking about Washington wine, travel and all the usual things. More innuendo was being thrown around, and eventually we finished up the wine and I asked the bartender for the check. Rick and I had the usual brief argument over the check, but I won out and threw done a credit card.

Rick thanked me and then said "This was really enjoyable, how can I repay you?"

"I can think of a few ways," and gave him a wicked look as I signed the check.

Rick said "Tell me more," and quietly reached under the bar and squeezed my upper thigh and lightly brushed my balls and fast hardening cock with his hand.

"Follow me," and we quickly walked out into the night. I told him that I was in a nearby hotel and that I would love for him to come join me for the night. He agreed that was a great idea and quietly asked what I like. I told him I love sucking cock and would bottom for him if he was up for. We were in a darker spot on the street and he stopped and said he was a top and would be down for all of that and more. I reached out and felt his growing bulge. He pulled me close and kissed my neck and grabbed my crotch. I whimpered with anticipation but quickly broke our embrace so we wouldn't be seen and we turned the corner into my hotel.

We both had noticeable hard ons as we walked through the lobby, but we tried to move slowly and not be too obvious that we were soon going to be naked and going at it in my room. We made it to the elevator alone and as soon as the door closed we were all over each other, with Rick kissing and tonguing me up against the wall. Walking down the hall and keying into my room, we could barely contain our excitement.

As soon as we were in my room, we started kissing again and feeling each other up and peeled off our shirts as we backed towards the bed. There were no lights on in the room, but the curtains were open to the waterfront and the lights of the city erotically lit the room. As Rick was kissing my neck, I had a firm hold on his now fully erect cock through his pants but I needed more. I undid his pants and they fell to the floor and I followed to my knees, coming face to cock with his underwear covered bulge. It looked and felt big and I slowly rubbed and stroked it while looking up at him. Wicked pleasure was in his eyes and he said "Go slow, this is going to be good."

"Yes, this is," I hissed and pulled down his boxers to expose what was a massive purple cock head. I caught my breath and leaned in to flick my tongue around it, and Rick got weak in the knees. I squeezed his still covered balls, and could feel the size and weight of them that seemed to match his dick. He moaned and I took the opportunity to whip his boxers off. He stepped out of his clothing, now fully nude and sat down on the edge of the bed and spread his legs for me. His cock had to be at least 8 inches long and thick. I scooted in and started licking and sucking on those massive balls, and Rick took the opportunity to slowly stroke his cock and rub it all over my face whenever I came up for air.

I needed to slow this down, so I stood up and took my pants off. Rick was still slowly jacking his cock and watching me, so I made a strip show out of rubbing my covered cock and wiggling my ass for him before I dropped my underwear too and stood before him naked. We both jacked our cocks for a minute and made eye contact and I stepped back in and kissed him. He reached for my cock as we kissed and he lightly stroked my erection. I dropped back down to my knees to find he was already leaking pre cum. I took hold of his cock and squeezed a few more drops of cum out and then gently licked it off his dick head. He moaned and fell back onto the bed as I played with his balls again without losing hold of his beautiful erection. I gave him a minute to settle down, then without warning I swallowed him almost whole and held his cock deep in my mouth, sucking and swirling my tongue where I could.

"Oh my God!" he just about yelled. I slowly started working my mouth up and down his erection, lapping up his increasing pre cum and working the head of his dick, building up saliva before I eventually took that massive cockhead in my throat. I held him there and just pumped his cock just slightly in and out with my mouth and throat as I took breaths when I could. My saliva was pouring down his dick now and onto to his balls. When I released his cock from my mouth for a moment and started massaging his balls, he slid up fully onto the bed and I followed onto all fours, still in position over his cock.

I took hold of his dick again and just started slowly stroking it and enjoying the feel of the skin moving up and down against his hardness. "This is fucking amazing," Rick said in almost a whisper.

I felt totally in control and I replied, "We're just getting started, my friend." He quietly moaned and rolled his head to the side, and I went in for my first prize of the night and while holding the base of his cock, went back down on his glistening hard on. I would slowly take his dick all the way into my mouth and gently squeeze his balls and then work my tongue all over and around his pole on the way back up before giving his head some action. He was leaking a pre cum river now and I knew he was close, so I started bobbing up and down on his cock with increasing speed and pressure. I could feel his cock start to swell and when I went to squeeze his balls on a downstroke, I felt them contract, he went still and he exploded with a massive, grunting orgasm into the back of my throat with 4 or 5 huge blasts. I could barely contain it all and his cum quickly leaked out the corners of my mouth and back down onto his cock and balls.

I held him in my mouth as he came down and I continued to slowly, gently suck and lick him. As he started to go soft, I kissed and sucked up the cum that had escaped and polished his balls. I crawled up next to him, satisfied with how this was going, and he just said, "Fuck me, that was something else."

I just laughed and said, "Actually, something else is that you're going to fuck me!"

Rick laughed too and said "Deal! I'll need a few minutes, what can I do for you in the meantime?" as he reached down and started fondling my cock and balls.

"That's a good start," I said and he leaned in and kissed me again. He grabbed hold of me and started stroking my cock and he kissed my neck and worked his way down to my nipples. He lightly kissed and flicked and bit my nipples and my cock seemed to get bigger and harder in his hand. I started leaking my own pre cum and he used that to get me slick. I was getting excited and he noticed and slowed things down by squeezing my balls and working a finger lower into my crack. He would swirl a finger around my opening but not finger me and that had me writhing and moaning on the bed.

"You like that?" he said.

I bit my lip and shook my head yes.

"Let's go with that then," and he hopped off the bed and pulled me to the edge. He kneeled down and pushed my legs up so my asshole was fully exposed to him. I shave everywhere, so when he spread my ass cheeks and saw my bud pulsing with excitement for him, he took the opportunity to start licking and rimming all over. That was driving me nuts and I could barely stay still. He grabbed hold of my cock by way of keeping me in place and started plunging his tongue into me and wiggling it around. I was doing everything I could to get him to stroke me as I needed to come, but my pre cum just kept leaking out onto his hand firmly on my cock as he continued rimming my ass. Finally he stood up and started working a finger around my opening again, leaned in and licked up my pre cum on his hand, and when he went to swirl his tongue around my cockhead, he plunged his middle finger into me and swallowed my cock whole and I exploded hard into his mouth. I cried out in ecstasy as he slurped down everything I gave him as he continued slowly working his middle finger in and out of my asshole.

"Wow!" was all I could get out. He kept gently fingering me and leaned down and licked my nipples.

"This is going to be so good," he added and started working a second finger into my asshole.

"Oh my god, yes!" and I started working back against his penetration. I could see he was hard again and told him to get on the bed with me. He pulled his fingers out of me and laid down and grabbed his cock and started stroking it again. I started sucking on his nipples as he stroked himself. and I eventually worked my way down his abs and back to his dick. I swung my leg over his head and we were in the 69 position. I kissed and licked and sucked my way up and down his shaft and had his head shining with my saliva. Rick was licking my balls and rimming me again, getting me ready for the fucking that was to come, tugging on my growing hard on.

We were taking our time getting there and when I sat up I was essentially squatting my asshole over his superb tongue digging in and out of me as I whimpered with pleasure. I was stroking his cock and could feel he was ready. I ground my asshole down on his tongue and chin and asked, "Do you want this now?"

"Fuck yeah!" he growled.

I kneeled over and licked my way down his stomach and sucked and slathered his cock with my saliva and spit, and dragged my cock and balls across his as I made my way into the doggy position. I put my ass in the air and spread my cheeks to let him know I was ready for him. He kneeled behind me and went hard at licking up and down my crack one last time and stuck his middle finger in me again. He worked that deeper and deeper and kept adding spit as I loosened up and then he worked a second finger in me again. That felt amazing and full and I could feel my ass relax. I ground back against his fingers and grunted "Now! Now! Now!"

Rick pulled his fingers out and I felt him give one last long lick from the bottom of my balls, across, around and into my asshole, and then moved into position. I felt him put that big fat cockhead at my opening and push it around and probe me just a bit. I was moaning quietly and when he finally started pushing that beautiful cock in I gave out a long sigh and told him "Don't stop."

He grabbed my hips and kept gently pushing in and I could feel every inch filling me up as he entered my anal cavity. Once he was past my ring, the feeling of his beautiful thick cock had me lightheaded as he slowly slid all the way and bottomed out with his massive balls firmly against the bottom of mine. He let out a long satisfying groan as my ass swallowed his cock and he held still for a minute but reached underneath and fondled our balls together.

I was ready to be fucked and started working my ass against his cock. He slowly started pulling out but stayed deep in me and kept pushing back in. He was in control and I let him take over. He had a firm hold on my hips and would pull further out and spread my ass cheeks before plunging back in. Eventually he was coming almost all the way out before slowly sliding all the way down again. I was tingling with pleasure and moaning like a whore for him. He then laid down on my back and changed the angle of his cock going into me and new waves of pleasure hit me as he kissed and nibbled on my neck.

I mumbled "Soooo fucking good" and he would pick up the pace for a minute and slow down again. He pulled me up so I was on my knees and he reached around and stroked my hard on. I could feel my balls bouncing around with his erection buried deep in my ass and pointing straight up. It was amazing.

Rick pushed me back down and I buried my face in a pillow and pushed my ass high into his cock. It sounded like he was starting to lose control and he started plowing into me faster and faster. I thought for sure he was going to cum but he found the will power to slow down again and slowly pulled out of me. Without even speaking I knew what he wanted and I rolled over onto my back. He moved into the missionary position and we started kissing and tonguing each other again as he lined up his cock again at my now gaping asshole. I felt empty without him in me and I begged him "Fuck me hard."

He reached down and slid that cockhead into me and then pounded deep with all of it. I gasped and just about passed out as he hit bottom again. He pushed my legs up and started driving that 8 inch monster into me with abandon. I could feel those heavy balls slapping against my ass crack with each downstroke and I knew he was close. I was too but I could only concentrate on the sensation of Rick's cock drilling in and out of my ass. I was leaking pre cum again hard and Rick found the control to slow down once more and stroke my dick with it.

He quickly pulled out of me and slid me to the edge of the bed aggressively. This had been an amazing fucking but we were both there and needed to finish. I put my legs on his shoulders and pulled his hips in so he could get back to fucking me. Rick pushed that cock that felt like it was made for my ass, grabbed my hips and started pounding me. We were both moaning and grunting with every stroke and when I grabbed my own cock and started stroking, within seconds I started shooting cum all over us and seconds later I felt Rick's cock grow deep inside me and he erupted that had waves of ecstasy washing over my body as his cum filled me up. He kept slowly sliding in and out of me as he came down, I was quivering with the best orgasm I'd ever had.

He stayed inside me and pushed us back up onto the bed and quietly laid on top of me as we nibbled and nuzzled each other. I could feel his load leaking out of me and when he finally pulled out I could feel his juice running down my ass crack and soaking the sheets.

We just looked at each and laughed. He summed it up best by saying "That was the best bottle of wine I've ever had." I couldn't have agreed more.