My Older Masseur

My craigslist post was short and simple. I wanted an older male to give me a massage and be open to exploring more. Well, to be completely honest, I wanted to do the exploring, the older man I fantasized would just need to be safe, patient, and willing to take control.

Needless to say, I received tons of responses. Something about a 38 year old seeing a top male for a massage garners lots of responses--go figure. Well, after combing through my inbox I settled on one guy in particular--Jonathan. Jonathan was 58, had his own massage table, and was completely into giving massages and seeing where they lead to. He had a good looking face, a bit of a belly, and from his pics, at least 7 inches of manhood when fully erect. I kept going back to his pics, and realizing that him being older and having a bit of a belly was a huge turn on--something staring from underneath his stomach, cock and balls got me super aroused.

After many emails back and forth, we agreed to meet up on a Friday night after my live in girlfriend was visiting her parents back in Ohio. Living in New York City, I felt fairly certain that hooking up with a guy and not seeing them ever again was a fairly good bet. We agreed that I'd meet him at his place on the upper west side. I picked up some beers in the bodega by his building with my heart beginning to creep into my throat. I rode the elevator up to his floor after he buzzed me in, floor number 18 of a 23 story building. I left the elevator, turned right and I heard a door being unlatched and before I could even compose myself Jonathan was opening the door standing in a bathrobe with his hair wait and freshly combed.

"Hi Josh, c'mon in."

He swung the door open wider and I walked into a very nicely decorated, dimly lit living room with a massage table in the middle.

"Wow. Nice space."

"Thanks! Let me take those beers from you. Would you like one now?"

"Definitely." He went to the kitchen, popped open two beers, and took one over to me.

"Cheers," he smiled at me.

"Cheers," I replied. "To trustworthy strangers," I added with a wink.

Jonathan invited me to sit down on a love seat across from him. We made some small talk about the city, and what we did for a living. I polished off my first beer and asked if it was okay if I helped myself. He said go ahead, make yourself at home. When I walked into the kitchen I realized that I was moments away from receiving the erotic massage I craved for as long as I could remember. With my second beer open, I felt like I floated into the living room with my knees weakened from my nerves.

I gathered up my will and sat right next to Jonathan, clearly sending him a sign I was ready.

"How are you feeling?" He asked, turning toward me.

"Dizzy, excited, and willing."

"Well, let's start our massage here. Why don't you sit on the floor between my legs so I can rub your neck and shoulders."

All I needed to hear was between my legs to get me fully erect and nearly ready to shoot my load into my jeans. I complied and got myself comfortable sitting on the floor.

He began by assessing where my knots were, digging in and turning me into jelly. My neck, my shoulder blades, my upper arms were all given a once over. He tapped me and told me to stand up and move to the massage table.

I was so relaxed, and so hard I could have cared less when he told me to get naked and lie down. I stripped, and I could tell that Jonathan liked my 6 inches of manhood as his bathrobe was tenting forward.

"Lie down on your stomach."

I complied, somewhat hopeful he would just tell me to lie on my back so I could see him and reach for him when they moment was right.

He started in again on my neck and back, only this time his cock was just inches from my face. He belt from his robe was draped over my head, caressing my hair and neck each time he reached down my back.

I heard him step back and suddenly a bottle popped open.

"Oil or lotion?" he asked.

"What's your preference?"

"Oil."

"Great." I said, feeling the precum leaking out of my cock.

He applied a very generous coating of oil, clear down my back and into my ass crack. I felt it drip down my crack down my taint and onto my balls.

He began to rub me with more of a purpose now, harder and going lower down my back. He was standing off to the side of me now and I could tell his cock was head high with my face, and his hands worked their magic to the top of my ass cheeks. He deeply rubbed my globes, occasionally parting my cheeks and glimpsing my rosebud.

In my fantasies all I wanted was a rub down that lead to me blowing him, ass play did not figure into my mind. Which is all the more reason I was surprised when I began to have the involuntary response of arching my hips to him, seemingly inviting entrance for him to probe my asshole.

He didn't need much prodding before I felt the occasional finger graze my rosebud, with me puckering and arching each time. He finally paused his index finger over my hole and said, "Is it okay to go deeper?"

At this point, I nearly thrusted my ass so high and so hard I could have engulfed a fist.

"Yes--please," was all I could muster and I let out a soft moan as he slowly slid his finger deep and gently inside of me. My entire body shuddered with his entrance and I turned my head to see his bulging robe.

I couldn't wait any more. I spread his robe, took his cock out and went to work, taking him as deep as I could muster. His pace quickened inside of me as did mine--slurping and sucking and jacking his cock into me as best I could. I wanted his come in my mouth and down my throat immediately. It took maybe three minutes of him thrusting in and out of me when he began to tense up and we both began to come, rope after rope--him blasting my mouth and me coming into the table.

Spent, and with him now draped over me, I cleaned his cock as he stroked my hair.

"You can come back anytime."

I removed his cock and kissed the head.

"Thanks," and I squeezed his cock to get one last drop.