A boys first time with a man

I have always had a desire to have things in my ass. As a young teen I would lotion up and insert just about any phallic shaped object I could find in my ass. Yet I always desied to have a real cock in me. Problem being that I'm from a small town in western WI. If you were found out to be a "fag", the consequences were swift and brutal. Not that I was gay. I had been having sex with plenty of girls as a teen. But there was always that lingering and burning desire to be fucked. Then one day, after a series of unfortunate events, opportunity came knocking.
In the mid 90s a couple of friends and I went to Madison for a party. A long story and a series of unfortunate events later, I found myself stranded with no way home. I had a friend wire me a bus ticket that would get me alot closer, but still 45 miles from home. When I got to my final destination I made a few calls and finally found someone who would come after they got off work, which was in a few hours. So I set out to explore this city along the Mississippi.
That's when I came upon a seedy little shop that was only accessible through an alley. Best Buys. Not to be confused with the big box store chain. This place was dark, dirty, and had the oddest collection of porn I have ever seen. In the back they had video booths to watch porn on. So I stood in a booth, put my quarters in and began to flip through the channels. I looked around and noticed other men looking in my direction. Some were smiling, and some were outright masterbating. I only being 18 had no idea what the protocol was for such things. So I finished watching my videos and left. As I was standing outside fishing out a smoke a man walked out right behind me. He was a bit shorter than me, glasses, balding and could easily pass as my father. His name was John.
He asked me what I was doing in town, and I told him my tale of woe. He asked if he could buy me dinner since I still had a few hours to kill. I said sure and we got into his minivan. As we were heading to the north side he put his hand on my thigh, moved up towards my cock and asked me if I was interested in getting a room. With a trembling and nervous voice I said yes.
He checked us into a dumpy motel and we went upstairs to the room. As soon as the door closed he started to kiss me. I had never kissed a man before and I found his face stubble to be uncomfortable and off putting. He soon undid his pants and I quickly pulled his cock out. He was HARD! His cock was slightly longer and thicker than mine and it bent sharply upwards. He sat on the bed and I eagerly swallowed him. I had never sucked a cock before, but he seemed to be enjoying it. He was moaning loudly while grabbing my hair and guiding me back and forth on his cock. He eventually sat up, stripped the rest of his clothes and then stripped me. He layed me down on the bed and proceeded to suck my cock in return. Being 18 I had my share of blow jobs, but he was remarkable. I had to stop him before I came. He pulled a small bottle of lube from his pants beside the bed and quickly lubed up both of our cocks. He then laid on top of me and with our cocks sandwiched between us he began to hump me. It felt great. But there was still that burning desire in me that I needed fulfilled and this was the perfect time to do it. I was extremely turned on and was again close to cumming. I stopped him and told him I wanted him inside me. He asked if I have had sex with a man before. I said no but I always fantasized about it. He tried talking me out of it, saying it wasn't a good idea to jump right into anal. While he was still hovering over me, with both our torsos covered in lube, hard cocks slightly touching between pulses, I looked him in the eyes and said "Please".
He lowered himself and brought my legs up. He slowly rubbed my ass hole with the tip of his cock, occasionally pressing himself against it. I had both hands on his ass pulling him closer to me, trying to pull him into me. Then he was finally ready. He would push slowly, then stop, and then push some more. At first it was incredibly painful. He tried to pull out a couple of times but I told him to continue. After what seemed like hours, he was finally all the way in me. We laid there together, wrapped in an embrace until I was comfortable to continue. Slowly he started pumping in and out of me with very short strokes. Once I started moaning he went to full strokes. Then faster and then harder. This was everything I hoped it would be and more. It felt immeasurably better than the hairbrush handles I had been using. He started licking and sucking my nipples, another first for me. His hot breath on my neck, his tounge in my ear. It was ecstasy. Then I began to feel it. It felt like an orgasm, but different. It started building slowly, then it was roaring in me. Then it happened. I started to cum all over myself. I shot cum all over my stomach and some even made it up to my nipple. That's when he bent down and locked my cum off my nipple. Watching him do that made my orgasm even better. It clearly had an effect on him as well because as soon as he tasted my cum off my nipple, he started to cum. He slammed his cock all the way in me and held me tight. His body quivering and shaking as he unloaded his cum in me.
We stayed there, locked in our embrace. Slowly he lifted himself off me. His deflating cock flopping out of my ass. He helped me clean up and even wiped me after pushing his cum out of my ass. He even offered me a ride the 45 miles home afterwards. After driving a while we were 10 miles from my hometown, I reached over and started rubbing his cock. He quickly was hard again. He pulled over at a scenic overlook on top of the hills surrounding my town. I pulled his cock out and enthusiastically started sucking it. I wanted to know what cum tastes like. Needed to know. After some work, he finally shot his load in my mouth. It wasn't the great nectar I thought it would be. I found the consistency to be the worst part of it. Either way, in the passion of the moment I eagerly swallowed it all. He then reciprocated and left me dizzy weak legged. He brought me to my house, gave me his number, and drove away.
John and I got together 2-3 times a year after that time for almost 10 years. Sadly life moves on and we eventually lost touch. I used to occasionally go back to that dirty little porn shop Best Buys. Got a few blow jobs, gave a few blow jobs, but never met anyone like John again. Eventually Best Buys closed as well. Where it was now stands a big bus depot.
I realize now how lucky I was having someone like John for my first time. He was kind,gentle, patient and very sweet. I've heard so many horror stories of others first time. I think about him often and hope he is well. I am now married with kids of my own, and even named my one son John.
I hope you enjoyed my story as much as I did reminiscing about it.

Related Posts

More Related Posts