My jail bird story

One of my earliest jobs was delivering newspapers, I enjoyed doing it and always met people, especially when collecting for their subscription each week. I had a few houses which I enjoyed making stops at, but this story is about one particular stop that I would plan making on a Friday afternoon.

I met him for the first time through the door, just a voice that asked me to come back tomorrow. I always felt this was a usual ploy only to come back with no one home an avoidance for paying the subscription. This wasn't the case when I arrived back at 16 Cross St. ;e next day, when the door was answered buy a naked man. He opened the door enough that we could see each other and then asked me to step in and close the door while he got his wallet. As he walked away from me, I could check out his muscular ass and legs that were thick and beefy. I was thinking he would come back with his pants on and I wouldn't get a look at his front, but to my surprise he returned with his wallet and a nice cock swinging from side to side. I couldn't help but stare at a short soft fat cock with a very nice cut cock head. I figured that it would get to be 7" when hard. The name on the subscription invoice was Richard and I wanted his Dick. I looked up at Richard as he got closer and he could clearly see what I had been checking him out and he excused himself for no clothes. I didn't say anything as he went on making excuses how he had just gotten out of prison and didn't have the chance to hang out naked in a while. I smiled and told him the amount on the bill and he handed me a five and told me to keep the change so I thanked him and then asked what he was in prison for.

Richard, looked at me in surprise and said a story for another time, but my curiosity had the better of me and I said that you are my last stop and had some time. He smiled and told me to come sit down as he walked to his bedroom. He laid down on his bed and I could see his cock was starting to get erect as it laid across his thigh. Richard told me to sit on the bed as he began telling me about his friends, a party and his drinking that led to an automobile accident killing someone that had him incarcerated for 7 years. He was about 24-25, so it was clear he was a teen at the time. He was much older than I was, but he seemed gentle and friendly as he changed the subject and then asked if I wanted him to put pants on. I was excited by his naked presence and told him I didn't have a problem. It was hot out and I was wearing jean cut off shorts and a tee shirt and on hot days I didn't wear underwear, so I felt I was close to being naked. I could see Richard's cock becoming more erect when I asked him about being in jail with all guys. His story talked about the exercise yard, library and how sometimes having to be naked with lots of other men. I then noticed his cock lift up and a small drop of his nectar on his cock tip. He saw me staring and told me to touch it if I wanted. I was mesmerized and took his cock in my hand giving it a squeeze looking at more pre-cum ooze from his cock tip, so with my other hand I wiped the juice from his cock and put it to my lips.

His juice tasted salty and sweet and I squeezed his cock again trying to get more juice. Richard asked if I liked that and if I had other guy friends. I told him not many because they all thought I was a faggot. He smiled and asked if I was and asked then about any boyfriends. I told him no, but didn't have a lot of experience except for a few older men I knew and some experiences with them that may make me a faggot. I could feel his cock get harder as he was now getting more excited and I bent down taking his cock head into my mouth. I heard him moan as I licked off and sucked out his delicious pre-cum. I moved back on the bed towards where he laid and I felt him slide his hand up inside my shorts pant leg. He commented on me being commando and my smooth ass and I could feel my cock start to harden. I was licking his cock head and then slowly pushed my head down taking more of his cock into my mouth until I felt it push into my throat when I gagged. I could feel Richard's hand gently squeeze and massage my ass as he pushed a finger between my ass cheeks probing looking for my knot. Without taking his cock from my mouth, I reached back pulling my shirt over my head and unbuttoned and unzipped my shorts. I now felt Richard probing my ass circling a finger around my hole as I was now moaning and leaking pre-cum. I was bobbing my head up and down sucking Richard's cock best I knew how and felt him tug my shorts down over my ass and down to my knees. He said for a boy with not much experience I sure could suck cock. That made me feel good and I started working my tongue around his cock head and sucked him deeper into my throat.

Richard lifted my legs and pulled them across his chest and then pulled me back taking my hard cock into his throat. We were in a 69 position and me on top sucking his cock as Richard stopped and again started probing my ass. This time he had wet my ass and started to fuck my hole with his fingers. I had my hole played with before even rimmed a couple of times, but I had not yet been fucked by fingers, or a cock, but felt that was about to change. Richard pulled me back towards him and flipped me over. He began kissing me deeply and lifted me to position his cockhead at the entrance to my hole. Our kissing was deep and exciting as I slowly pushed down trying to take his cock into my hole. I reached under me and spread my ass open further as I pushed down taking his cock. It was a little painful, but I was slowly pushing down with an occasional pause until the pain stopped until I was sitting completely with his cock balls deep in my hole. We continued kissing and I squeezed his cock with my ass and then began to slowly raise up and then down again. I had to change my position so I could fuck more of this cock into my ass. It felt so good and Richard helped me get into a position that now allowed me to rock up and down as I rode his cock. I must have been doing it correctly because it felt so good in my ass and Richard was moaning. He started telling me about his first time in prison, that two older men cornered him in a cell and each took turns holding him down while the other fucked him. He said it got easier after that, but that he much preferred having his cock buried deep into a tight ass than one in his. I told him that this was my first and I think I would prefer it this way, he grabbed my ass and started lifting and lowering me down on his cock as we began our passionate kissing again. Richard lifted me so that my ass almost released his cock from my cunt and then lowered me, dropping me to allow gravity too work for us and then lifted me up over again and again as we both were locked in a deep tongue tag kiss, moaning at each deep penetration of his cock.

We had been fucking for about ten minutes and Richard told me he was going to get us more comfortable as he slowly pushed me back pushing my legs up over my chest. He never took his cock from my hole and now had me on my back with him holding my legs up with his cock balls deep. He slowly started to fuck me in this position and I could feel how deep his cock would go over and over as he was picking up speed. He told me that it would be my first time having my hole filled with cum and pushed his big dick in as deep as it could go exploding his cum deep into my ass. His cock didn't seem like it would ever stop and I could feel some of his cum running down my ass crack and he then lowered my legs and laid on top with his cock still in my hole and asked if I liked that. I responded that I did very much and that I would be back again next Friday to collect for his invoice again. He smiled and then pulled his cock out of my hole with a plop and moved up to straddle his cock over my mouth for a good cleaning telling me that I was a good faggot and was now his faggot every Friday.