I Think Your Time is Up

I had had many "erotic" massages over the years, all from women. Some of which were memorable, most of which were not. There was the occasional blowjob or finger up the ass but by and large they consisted of a shitty massage and a perfunctory hand job.

One boring afternoon I typed Esalen into the search feature on Craig's List and the first hit was a dude. I skipped over it and looked at a few uninspired postings before coming back to his listing. On an impulse, I clicked it and found it quite intriguing. His name was Chris and he was a multi-modal masseur offering a "wide range" of services. Scrolling down, I was rewarded with a tasteful pic of a handsome nude man somewhere in his 30s who was in excellent shape. As I stared at the photo, I thought, "why not?" At worst I'll get a strong massage and I can always say no to the extras. So, I shot off an email and waited. A few days passed with no reply so I kind of figured it was a CL dead end. Then, one evening I got a reply saying that he had been traveling and was back now and taking appointments. We set something up for later in the week and I was on my way to trying something new.

The day arrived and I was awash in a mixture of arousal and fear. I wasn't sure what to expect and the mystery was intoxicating. I arrived at his place at our agreed upon time and Chris answered the door in a white t-shirt and some yoga pants. He had a kind face and an even tone to his voice that helped calm my racing pulse.

"Come in and make yourself comfortable" he said with an easy grin. "The bathroom is down that hall and the table is all ready for you. When you're ready, just give me a holler and we'll get started."

I began to think I had misjudged Chris and what he was offering. The place was immaculate and well lit and he was dressed like a masseur. There was no hint of sexuality to the experience so far. I cleaned up a bit in the bathroom and undressed before climbing on the table. I draped the towel across my ass and called to Chris. When he entered the room, he dimmed the lights and put on some nice jazz (thank God because I hate that New Age stuff most people play). I could hear him moving about but with my face in the cradle, I couldn't see a thing. Eventually, his hands touched my back and just rested there giving me time to warm to his touch. The massage was typically Esalen with long smooth oily stokes. Chris moved the towel to one side so half my ass was exposed and ran his strong hands from ankle to lower back in one continuous motion. I was in a state of total bliss and let myself go, relaxing into his work.

I was shaken out of my stupor when his cock brushed against my hip. I had not realized that Chris had disrobed (traditional for Esalen) and I jumped a bit at the contact.

"Are you ok?" he asked sounding a bit surprised himself.

I stammered, "Fine, I think I drifted off or something."

The towel was gone and my legs were slightly spread. His intensity picked up and his hands were now kneading my ass, pulling my cheeks apart and pushing me into the table. With each push, my cock ground against the sheet and began to stiffen. I new that any time now it would be apparent to Chris that I was really enjoying his treatment. Sure enough, when I felt a little precum ooze from the tip of my cock, he spread my legs further and climbed on the table.

The first thing to make contact was his muscular chest as it pressed against my buttocks. His weight sank onto me as he slid forward increasing the contact to his torso and eventually, his semi hard cock which came to rest between my ass cheeks. He ground into me and his cock pushed against my crack as it filled with blood and desire. With one down stroke, our cock heads touched and it caused me to sigh. I guess Chris took that as his cue because he slid back down and off the table.

"Turn over" was all he said.

Without hesitation, I rolled over and was filled with erotic warmth. The room was lit with scented candles that I hadn't noticed in the cradle and Chris' oiled body glowed in the soft light. His hands came to rest on my stomach and with my breath, moved in opposite directions. His left hand came to my chest and rubbed long circular strokes putting pressure on my nipple. His right hand moved to my lower abdomen and pushed in right at the base of my cock. It was an incredible sensation and I closed my eyes and breathed into it. The left hand then came to rest over my heart as he grabbed my cock and slowly stroked it's length. I pushed into his hand eager for release but to no avail. Chris kept his grip tight and his rhythm slow. At the top of each stroke, he swirled his fingers around the head and slowly plunged back down to the base which he would squeeze tightly.

Once again, I was lost in his attention and came around when his hand left my chest and his fingers ran through my hair. Then abruptly, he grabbed a handful of hair and with a tug, pulled my head back, which caused my eyes popped open. There, inches from my face was his cock. With his hand still full of my hair, he moved toward me and my mouth opened accepting him gladly. It was an interesting sensation to have something living and pulsing in my mouth. It was hard and soft at the same time and it felt amazing. As I sucked him he began to pump into my mouth instructing me to use my breath again. I felt I mixture of power and helplessness as his pace quickened and I relaxed into it. He also continued to work my cock over roughly now quickening his pace and bringing me to the edge of orgasm. Each time I thought I might cum, he stopped stroking and squeezed the base hard. On one such stroke, he pulled out of my mouth and again moved between my legs.

I did not look up but felt the table creak under his weight. Kneeling between my calves, he bent forward and took me into his mouth. There was no playing around now and Chris went to work hard on my leaky cock. It was without a doubt, the best blowjob I had ever had and in minutes, I was ready to blow.

"I'm gonna cum" was all I could get out.

He quickened his pace and sucked for all he was worth before I exploded into his mouth. When I started to cum, he pulled up so just the head was in his mouth and when I finished, he bent to my face and kissed me, swirling my own cum into my mouth. What an incredible sensation and taste. It was the first time I had ever tasted cum and mixed with his tongue and saliva, it convinced me that it would not be the last.

I wasn't sure what was going to happen next but Chris clearly had a plan. He kissed me again and his hand slipped under my knees, pulling them back and exposing my ass. He broke the kiss and looked me in the eye. He did not ask and I did not object so he moved his face down and began to rim and eat my ass like a man possessed. This was also a first for me and again I was sure it would not be the last. What a feeling! I was moaning now and calling on the higher powers, which Chris knew, was the green light. He knelt up and looked me in the eye while he stroked his cock. Then, leaning over to a nearby table, he grabbed lube and a condom. Without taking his eyes off me, he rolled the condom over his rock hard cock and slathered my pucker with lube, LOTS of lube.

Leaning into me, the tip of his cock contacted my asshole and he just pushed. Slowly and gently at first but with constant pressure. I didn't think it would go in and I started to say so but he stopped me.

"Use your breath" he said. "Look at me and breathe. Push out a little and you will let me inside you."

I did as instructed and was rewarded with a lightning bolt of pain as his head slipped past my virgin sphincter. I did not cry out but kept breathing as he remained still and in a moment, the pain passed. When the look of panic vanished, Chris started pushing once again and I felt myself slowly filling with him. It took some time, patience and a few strokes but soon enough, he was all the way in and I could feel his pelvis against my ass. I closed my eyes yet again and exhaled. Chris built slowly into a steady rhythmic pounding of my bowels. I could feel him rubbing against my prostate and my limp cock oozed a clear liquid. His cock swelled more and his pace turned rougher and more purposeful and I knew what was coming, no pun intended. As he came, he threw his head back and slammed into me as deeply as possible. I felt him twitch and spasm and heard his grunts of pleasure. When I opened my eyes again, he kissed me softly and said, "I think your time is up."

We both laughed and then lay there quietly for a moment until we caught our breath; then he cleaned me up and sent me home.