Bottoms Up

I met Ray at a conference last year and he was the first guy I ever gave a blow job. Both of us married guys looking for something different in our sex lives. Neither of us looking for a life change. Ray and I started meeting at conferences or on business trips every couple of months. We would meet in his hotel room, have a few drinks, I would suck his cock, and then he would jerk me off. I enjoyed sucking cock more each time. I felt myself getting better at it and I could tell Ray's enjoyment increased as my prowess did.

When I got a text from Ray with the details of another meet up, I was super excited. All the way to the hotel that afternoon, all I could think about was the sensation of him cumming in my mouth. Our meeting started the same way as always. Ray was freshly showered and wearing only a towel around his waist. There were a few beers chilling in the ice bucket. But this time, as we made the usual small talk drinking beer, I got the feeling that something was different. I couldn't figure out what. Not bad, just different.

A few minutes later I was naked and on my knees in front of Ray. I ran my hands up his muscular athletic legs and leaned in. His 7-inch erect cock rubbed on my face and neck. I tilted my head and let his balls drag across my cheeks and nose before giving each ball a kiss and a lick tasting his manhood. I was trying to tease Ray but it backfired making me crazy to have him in my mouth. I gripped his rod at the base and licked all over the head before taking him in my mouth and sucking his perfect cock.

"Let's try something different," he said pulling away from me. He slid on top of the bed and motioned for me to join him. He lay on his side with his legs spread wide, his cock shining with my saliva. I climbed in next to him and started to suck his cock again. He kept adjusting his position on the bed and pulling me around into a different position with his strong hands. I got the message. He was trying to move into a 69 position. I was confused because Ray had never once tried to suck my cock. It was always the same. I'd blow him and he's jerk me off into a towel. It never took long for me to cum because sucking cock and swallowing cum was such a turn on for me.

Being in a sideways 69 position gave me a whole new approach to his cock. I was able to lick his balls more and he groaned in appreciation. I let my tongue explore down beyond his balls and the thought of rimming him popped into my head. I worked my mouth back up and resumed sucking his rock hard cock working on my deep throating skills from this angle.

Ray didn't make any move to suck my cock at all. He stroked my cock a few times but then he started using both hands to rub and stroke my ass. His finger tips lightly brushed over my smooth skin. Then his fingers would dig in, firmly kneading my butt. I have a smooth round bubble butt and I could tell he was getting into touching and exploring it. He even spread my cheeks wide open a few times. His hands felt great on me and I went to town on his cock slurping, sucking and gagging on his rod.

Ray shifted again sliding in behind me and reached around to stroke my cock. I felt his spit-slick cock head rub the small of my back. As Ray continued to jerk me off, he started to rub his cock all over my ass cheeks. I was surprised but it felt so good. I wanted his cock back in my mouth as soon as possible but I decided to let this play out a little. Ray seemed to enjoy it.

He held his cock in his hand and rubbed it all over me. He tapped it against my soft skin. The sound of him slapping his cock on me was almost a bigger turn on than the how good it felt. He kept stroking my cock with a slow steady rhythm. And then he moved his cock between my cheeks and started humping, his cock sliding up and down between my cheeks.

"Does that feel good?" he asked. I told him it felt amazing and I wiggled my butt a little as he moved against it. As we continued, I heard him fumbling with something in the night stand drawer. There was a crinkling sound and a snap of something plastic. "I'm going to fuck you now," he said. His voice was low and raspy.

My mind raced but my body was frozen. It's not like I'd never thought about it. Of course I have tried fingering my own ass when jerking off. I was just starting to get good at giving blow jobs. Bottoming wasn't even on my radar. A sudden realization of how big Ray's cock was made me panic. Before I could speak, I felt Ray's well lubed index finger push into my ass. I gasped at the unexpected sensation. Ray just started working his finger in and out. I could hear the slick sounds of it behind me and his raspy breathing by my ear. I heard the plastic click again and realized it must be the top to the bottle of lube. Reapplied, he pushed two fingers up my ass.

After a few really deep thrusts he let his fingers slowly slip out of me. He stopped stroking my cock and I felt him turning back toward the night stand again. My mind raced. Was I really going to let me fuck me? It wasn't that long ago that I had a cock in my mouth for the first time and now I was going to have a cock up my ass? The rush of thoughts came to an abrupt halt as I felt his lubed, condom sheathed cock sliding between my cheeks. He pressed the tip of his penis against my tight puckered star and rubbed around it with gentle pressure. "Oh god, yes," I blurted out as he rubbed his cock against my hole. It felt so amazing. I knew I wanted this.

"Pull your legs up toward your chest," he said into my ear. His hands guided me into a position on my side with my knees up. He re-positioned himself behind me and I felt his cock rubbing on my rosebud again. "I promise I'll go easy," he reassured. He pushed in. I felt the blunt pressure against my star and then his cock head popped in. He instantly had about a quarter of his cock in me. I winced and sucked in a sharp breath. He held himself still and reminded me to breathe. He talked me through a few deep breaths in and out. It hurt, but the sensation of fullness and pressure was delicious.

He started to move. Not in and out, just a small circular motion, his hips rotating slightly. I felt him push a little more in and then pull back. He kept that small push and pull going for a few minutes, ever so slowly pushing more of his perfect cock up my ass.I waited and timed his moves and I pushed my ass back as he pushed in. His cock plunged deep in my ass and I groaned loudly. After a few long full strokes in and out he pulled out. I felt my empty ass pulsing.

"Now I think you're ready." he said. He grabbed my hips and put me on the bed on all fours. He pushed my head and shoulders down on the bed and pushed my knees wider apart as he settled in behind me. I heard him adding more lube. He spread my cheeks with one hand and guided his cock to my hole with the other. He plunged fully inside me. I clutched at the blankets and buried my face in the bed. As he started a slow rhythm I readjusted to his big cock up my ass, the pain melting into that incredible feeling of being penetrated and full. Before long I felt his hands dig into my hips and he started to really fuck my ass. I was holding on for dear life as I felt his hips start to slap against my ass over and over. After awhile I was able to push back into him again and I heard him moan every time I did that.

He bucked into me faster and faster and I could tell he was going to cum. My own cock was waving back and forth under me leaking pre cum like mad. He rammed in deep and held himself there grinding against me. I could feel his cock pulse inside me as he came and my own cock exploded all over the bed. He collapsed on top of me holding his slacking cock inside me as long as he could. When my throbbing tunnel finally expelled his slack cock, he got up and went into the bathroom. When he came out I hopped up and ran into the bathroom myself.

When I came out, he had cleaned things up and he was wearing a T-shirt and sweat pants drinking a beer. He held out a beer to me as I approached. I got dressed quickly while taking a few long drinks for the beer. My ass throbbed. I realized that I really like the feeling of having a well fucked ass. I wondered how long the feeling would last. It was like that great feeling you get after a good run or workout. We made small talk as we finished our beers and I made an excuse for leaving. I rode the elevator down to the lobby thinking the whole thing over in my mind. I liked getting fucked way more than I ever thought I would. Still, I missed sucking him off to completion and feeling his cum in my mouth. I started thinking about how I could have both things another time in the future. The elevator bell dinged and the doors opened, wiping out my thoughts. It felt like I was almost waddling as I walked out the doors to the parking lot. I wondered if anyone noticed I was walking funny.