I was 24 years old living on my own in Boston. I worked downtown waterfront and loved to eat my lunch outside on the wharf. One day eating lunch a man who I found out later to be homeless came and bummed a cig from me. He was friendly enough and he sat down next to me and we enjoyed our smoke together. I went back to my office and I could not stop thinking about him. He told me his name Lee and he was 65 years old living at the pine St inn. He told me he was happy as long he has his cigs and a bottle of vodka. Over the next month or so I would meet on my lunch and have a hot dog and a smoke with him. Truth was I was very sexually attracted to him. I should say I have always been into older rough looking men. And Lee fit the bill. Faded tats up and down his arms. Very thick black hair on his legs. Calloused hands. Long black and gray hair.
One Friday I met him and told him I wanted to ask him something. I asked him if I gave him $100 dollars would he fuck me. I said I know you aren't gay but I if you have it in you there is nothing more I would like then his cock pounding my ass. I was shocked how fast he said yes. I left work and stopped at the ATM got his money and walked to my apt. When we got there he undressed and I fucking loved his body. Hairy with salt and pepper all over. Tats all over his torso. Dark brown nips the size of silver dollars. The smell coming from him got me so hard. I went over to him and he started kissing my neck. I started playing with his cock which was about 7 inches, uncut and loose balls that hung from him about 2 inches.
I took off my shirt and Lee sat me down on the sofa and straddled me and played my tits which felt so fucking good my cock was oozing precum like mad. I needed his cock in me so bad I couldn't wait anymore. I got up undressed and lay on floor with my legs lifted begging him to fuck me. He knelt down lifted my legs with one hand let his drool fall onto my hole and slipped in his cock so fast I let out a yell. For the next hour Lee fucked me hard in every way. I came twice jacking myself off as he fucked. Finally Lee let go and pulled his cock out of me and shot his load down my throat. We lay there a couple hours naked on the floor. I was getting horny again smelling the guy. We ended up having an awesome weekend getting drunk on vodka and fucking.
This went on about 5 months until I moved. I always try to track him down when I visit Boston.
Hope some guys like this. I am not a writer I just wanted to share this story.