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Personal Ad: Rick

I finally test the waters to fulfill one of my fantasies.
I’ve had some interest in cock since my days of teenage experimentation. I really never had the opportunity to find another guy to explore with until the internet made it very easy to meet like minded people without cruising bars, etcetera. I always fantasized what it would be like to jack another guy off again, or more.

While checking out the adult personals, I ran across a post that caught my eye. It was a 50-something guy looking for someone in my age range who didn’t have much experience. I set up an alternate email address and answered the ad.

This was how I met Rick. We exchanged emails talking about our own experiences, and what we were interested in or fantasized about. After we got comfortable with each other, we decided to meet in a public place to see where things go. I was the newbie, and he was the experienced mentor. I was looking forward to having someone take charge of me.

I walked into the local microbrewery and immediately recognized him across the room from the photos he sent over email. Rick was about ten or so years older than me, in his early-fifties. He was about my size physically, but a little more gray on top. He was clean-shaven and dressed “business casual,” probably coming straight from work as I did.

As I approached, he stood up and shook my hand. We exchanged pleasantries, and he waved the waitress over. “Would you like a drink?” Rick asked.

I just pointed to his glass and replied, “Whatever you’re having.” We both chuckled, and I joined him in the booth.

As we talked and sipped our beers, I really began to feel real comfortable talking to Rick. We mostly made small talk about regular things, like work and other interests we hadn’t previously talked about. Out of the blue, he asked me if I was interested in meeting somewhere else, which was the reason for our meeting in the first place. I was nervous, but eager for the experience. I nodded, Rick paid the tab, and we left.

Rick lived nearby, so I followed him home. A few minutes later, we were pulling into his driveway. He waved me in as I got out of my car, and I followed him into the house. He was turning lights on, and invited me into his living room area. It was a big room with a bar on one end. As I looked around, Rick walked over with two bottles of beer, and asked me if I wanted to get undressed.

I was really nervous, and he could obviously see that. Rick set his beer down and moved closer to me. He grabbed my shirt and pulled it up. I set my beer down and raised my hands to allow him to pull my shirt all the way off. He unbuckled my belt and soon my pants were around my ankles. I stepped out of my pants, and Rick gestured toward the couch. I sat down wearing just my briefs. He walked toward me unfastening his belt, letting his own pants fall to the floor.

He was not wearing underwear, and I watched his big cock swing back and forth as he moved across the room. He was shaved, and circumcized. He joined me on the couch and didn’t waste any time. His hands were all over me and he worked my underwear off. He squeezed and stroked my cock and ass. I could feel the swelling of my cock, and could see he was already half hard.

He leaned back, and told me to take care of his cock. He was stroking himself, and I moved closer to take over. I stroked his cock and it got even harder in my grasp. I could barely get my own hand around it. I leaned even closer and took him in my mouth. He let out a groan as my wet mouth slid down the shaft of his cock. I took it as deep as I could before hitting my gag reflex, and he seemed to like that.

As I licked and stroked Rick’s cock, I could taste the pre-cum he was leaking. I wasn’t sure I wanted him to cum in my mouth. I really enjoyed watching a cum shot, so I especially wanted to see the cum shot I was responsible for. Before long, Rick told me it was my turn, so I stopped and he laid me back on the couch.

There was a lot of pre-cum leaking from my own cock so Rick used it as a lube to get me hard again. He leaned in and started sucking my cock. My cock is just about six inches, but he was taking it all the way in his mouth. He could really suck a cock, and I wanted it to last all night.

Rick lifted my legs up and began to play with and tease my ass with his tongue. Before long, I felt Rick’s finger spreading something warm and wet on my ass. He slipped it in a couple times, and my cock jumped. I told him I never been fucked in the ass. He smiled and carefully worked his fingers in and out of my ass to the point I was pretty relaxed, and very lubricated.

By now, Rick was kneeling on the couch with his hands behind my knees holding my ass up. He reached down and guided his cock to my virgin hole. Rick pushed in slowly, and I felt him stretching me open. He pulled back slowly, and pushed back in. Little by little, Rick worked his cock deep into my ass. There was not as much discomfort as I thought, and it was starting to feel good.

Rick was very gentle as he continued to slowly pump his cock in and out of my ass while stroking my cock. The stimulation of Rick’s cock against my prostate brought me over the edge and I felt like I was about to cum. He felt my ass contract and grunted as he pulled out and started stroking his own cock.

The sensation of his withdrawal made me start shooting hot cum across my stomach and chest. Rick’s first blast hit me on the cheek, and I could taste his seed again as it dripped down my face onto my lips. The rest of our cum mixed together on my chest and abdomen.

Rick offered me a towel and walked out of the room. After we got somewhat cleaned up, he offered me the use of his shower which I accepted. I took a quick shower, and got dressed. Rick was wearing a sweat suit as I entered the living room area. He offered me a drink, but I had to get going. We agreed to talk about meeting again, and then I left.

On my way home, I wondered if I would really ever meet Rick again or if it was a one time thing.

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