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Older Man's Boyfriend

A painful first experieince...

I had been curious about male to male sex since I was pretty young, and I regularly masturbated thinking about how another guy's cock would feel in my hand, or how mine would feel in his.

Not quite sure how I found out, but when I was about 16 I learned the location of a popular meeting place for gay and bi men. It was basically a few parking lots downtown, that were otherwise empty late at night. Men would cruise the area, meet, park and engage in activities that at that time I could only imagine.

My curiosity (and a hard cock) got the best of me, and late one Saturday night I ventured out to check things out. It was hot, so I was wearing shorts and a t-shirt. I was a slim, 5'7", 16 year old, so I guess it wasn't surprising that I was approached immediately upon arriving.

A fiftyish gentleman pulled along side of me and asked if I would like to join him in his car. I was totally nervous, but opened the door and slid into the passenger seat. He drove to a more secluded lane, and asked me about my experience and what I would like to try. He started rubbing my inner thigh as he spoke, and I got very hard very quickly. Garry was very nice. He lived in an apartment nearby, and I didn't hesitate to say yes when he asked if I would like to go there with him.

As we entered his building, I realized how big he was. Well over six feet tall, and quite heavily built. After he closed the door to his apartment behind us, he held me tight to him; I could feel his hard cock pressed against me. His hands were fondling my behind, and before I knew it, were groping inside of my shorts. Feeling his warm hand on my cock was as wonderful as I had ever imagined. After a few moments he led me to the living room and asked if I would like a drink. I said I would, and he brought me a very stiff rum and coke.

We chatted and drank for a bit, and then he began fondling my cock under my shorts once again. He slipped my shorts and underwear off, and kneeled down to take my cock in his mouth. It was unbelievable was afraid I would cum instantly and asked him to stop. He got up and unbuttoned his shirt revealing a well built, hairy upper body. He then slipped out of his pants and underwear. As he stood in front of me his hard and very large looking cock was bobbing directly in front of my face.

I reached out to take it in my hand. Instinctively I started gliding my hand up and down his shaft. I could feel it pulsing in my hand and couldn't take my eyes (or my hands) off of it. "Would you like to suck it?" he asked. I placed my lips around the head and started gently sucking. I could feel his hands on my head, gradually applying more pressure to take more in my mouth. After a few minutes he pulled away, took me by the hand, and led me to his bedroom.

Now fully naked, we embraced at the foot of his bed. I could feel his hard cock pressing against me. He placed his hands on my shoulders, and gently applied pressure, forcing me to my knees. I took his cock in my mouth, and he held my head tightly as he worked it in and out. I started to gag, but wasn't able to pull away. I could feel him tense up as he held my head tight to him, with his cock fully inside me. My mouth was filling up; I could feel something warm in my throat and my mouth...and realized he was cumming. I suddenly became aware of my own hard cock and could feel myself cumming uncontrollably.

After a few moments he released his grip on me. I gasped for air. I took several big gulps, swallowing whatever cum was in my mouth in the process. I was conscious of what a mess I was as I got to my feet. I had his cum running down my chin, and my own all over my legs.

Garry slipped into the bathroom and turned on the shower. Returning, he grasped me by the hand and led me in with him. I felt dirty, and guilty about what I had just done, but the warm water felt good. He took a soapy cloth and ran it all over me. I quickly forgot my guilt and just enjoyed the experience. He turned me around and gently began massaging my back side. He ran his fingers up and down between the cheeks of my ass, then gently probed my asshole with his finger. I was soapy and slippery, and his fingered entered quite easily.

After a few moments of working his finger inside me, he pulled it out. It had gone in and out so easily that I was not at all uncomfortable, and actually though it felt quite nice.

Things changed quite quickly after that. Using his size and weight Garry pressed me forward into the wall of the shower. I could feel his large cock pressing against my asshole. I realized what I was in for and asked him to stop. He just slowly applied more pressure until I could feel his head enter inside me. By now I was terrified, crying and begging him to stop.

He plunged his cock deep inside me. The pain was excruciating. My knees buckled, but he held me up. Pressed against the shower wall, I could feel his hot breath on my neck as he mercilessly pounded his cock into me. It was such a relief when I felt his breathes shorten, his muscles tense, and his cock explode inside me. His warm cum made any resistance my tight asshole offered disappear. After several more deep, hard strokes he was finished. When he finally let me go, I collapsed and sat whimpering in the shower. 

After a short time, Garry helped me up, dried me off and helped me dress. He told me that I should learn to enjoy that kind of treatment, and that I would  make a very nice boyfriend for some lucky man.

At home that night, I though about my first experience. I was a bit shocked when I found myself getting quite hard thinking about how Garry had treated me. The pain was gone, only the memories of the pleasurable moments remained. As I came in my hand, I thought about my next visit to Garry's place.

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