Hitchhiking Hookup

It was the early 1970's and I was back in Boston to begin the school year. I was hitchhiking along Commonwealth Avenue at around 9:00 PM on a Friday after visiting some friends. I was thinking about giving up on a ride and taking the MBTA when a classic red Mustang convertible stopped and the passenger door opened. The driver was a well-dressed man of about 40-45. He was good looking, dark brown hair, deep green eyes and a welcoming smile. His name was Frank and he was a lawyer.

We chatted a bit and he told me he had gone through a bad week a needed a good stiff drink and invited me to accompany him. Since I was only 18 and looked 15, I didn't think any bar would serve me - I had certainly tried it often enough during my freshman year. "No problem", he said, "I live quite close and have plenty of liquor. Do you like Scotch?"

I had developed a real taste for scotch my freshman year so I quickly agreed to accompany him. It took very little time to arrive at his apartment, a modern (for the time) place on the twelfth floor with a nice view of the city. Frank poured us each a healthy measure of scotch and said he wanted to change out of his business suit into something more comfortable. I sipped my drink and admired the view from his living room window for a few minutes before he reappeared wearing gym shorts and a tee shirt. The shorts were close fitting and I could see the outline of his apparently large cock.

I tried not to stare but he caught me looking and smiled. Frank walked over to me and asked "Like what you see?" Then he pulled down the shorts revealing a semi-hard cock around 6 inches and thick. I could not tear my eyes from it as it swelled to around 8 inches as I stared dumbfounded at it. He took my right hand and placed it on his cock which was now rock hard. "Have you ever played with a man's cock before?" he asked. I silently shook my head no. "Would you like to?" With that he lifted my shirt over my head and began to unbuckle my pants and pull them down. By this time I had a raging hard-on. "You really do like what you see", he said. He knelt in front of me, pulled my feet out of shoes and pants and took my cock in his mouth. He licked and sucked for a few minutes before getting up and saying "I've had a rough day, I need a shower and I think you do too."

Frank took me by the hand and led me into the bathroom. His shower stall was large enough to accommodate both of us. The warm water felt very nice and the closeness of a naked man was exciting. He rubbed soap all over my body paying particular attention to my cock and balls. He even stuck a soapy finger in my ass. I was experiencing sensations I never knew existed. To tell the truth, I had occasionally thought about being with a man but I had always pushed these thoughts away. Somehow, Frank had overcome all my hesitation.

We dried off and went into the bedroom. He had me lie face down on the bed and began to massage me. Frank ran his fingers all over my back and my ass. He massaged my buttocks and ran his fingers through my ass crack. I tingled all over and my cock was harder than I could ever remember. Then he turned me over and stood in front of my face and began to gently slap his cock against my cheeks. "Open up," he said. I then tasted my first cock. Hesitantly, I licked the head running my tongue around his piss slit. Little by little my lips worked their way down his shaft. Soon I was tasting his precum and I swirled my tongue around his cock head rubbing the precum all over it. I could not believe I was sucking a man's cock and enjoying it.

Frank pulled his cock out of my mouth and turned me over face down. I felt something slightly cold and sticky being spread around my ass crack. Then he inserted a finger and began to push it in and twist it around. Then it was two fingers as he methodically loosened my ass. I knew what he was doing and I was scared but powerless to resist. After several minutes of exploring my nether regions with his fingers, I felt something bigger push against my hole. He was slowly sticking his thick cock in my tight ass. It hurt badly and I felt my ass was being torn apart. Relax", he said, "The pain will recede". Frank very slowly pushed his cock in a little deeper, letting it rest for a bit so my ass could adjust. Bit by bit he penetrated me deeper and deeper until his shaft was buried in my ass. He kissed my back and neck telling me I was a good little boy and he would make me his slut. I had never been more excited in my life.

Several minutes went by with his cock deep in my ass before he started to slowly fuck me. The pain had receded to the background and I felt a fullness I had never known. "My god," I thought, "I am being fucked by a man and I love it". Soon he began to pick up the pace and fuck me harder. I moaned as he went faster and faster, slapping my ass as he fucked me.

I loved the feeling of his huge dick filling my ass. When he came, I could feel a warmth flood my insides. Frank kept his dick inside me and kissed my neck telling me what a good fuck I was. He turned me over and his mouth engulfed my cock, which was oozing precum. He was good, he brought me to the edge and then let me down a bit. This went on for a while before I begged him to let me cum. When I did, I pumped what felt like a gallon down his throat. After sucking every drop of my seed, he took me in his arms and kissed me. I could taste my cum on his tongue and I loved the feel of his strong arms around me. I was ready to let him have me anytime, anywhere.

I noticed that his cock was still hard and I started to stroke it. "Suck it", he commanded, and I obeyed. I took more and more of his cock into my mouth - so much that I triggered my gag reflex. "Relax", he said, and he gently pushed his cock so deep in my throat that it tickled my tonsils. I quickly got the hang of taking him deep into my throat and then slowly moving my lips up to his cock head. I would swirl my tongue around the tip of his cock and then work my way down his shaft. I loved the feeling of his cock on my lips and tongue. After several minutes of orally worshiping his big cock, he shot a steam of hot cum down my throat. I managed to swallow all of it.

Frank smiled at me and told me I was a fast learner. He returned the favor and it took me hardly any time at all to release a second huge load of cum into his mouth. I spent the night with him and we made love several more times that night and again in the morning. We would get together several times over the next few months but those tales are for another time.