So it has been years since I have had any experiences sexually with homeless men. In college living in boston it was very easy to go out meet some homeless men hanging around and for a cheap night of some McDonalds, carton of Marlboros, and a liter of bottom shelf vodka I'd pretty much get what I needed. Now as a 30 something gay man living in the suburbs of Boston with my 55 year old partner of 14 years(who I love) I do miss that kind of raunchy sex I got from raunchy homeless men. So when my company put me up in a hotel in the city for some meetings I told my partner I may seek out some action. We have a somewhat open relationship and he knows my love for sex that way. He himself is a former homeless man in which the beginning of our "courtship" thats how we met. He on the street me looking for some homeless dick.
Sunday morning after the meetings had been said and done sat night I went about 6am to a shelter that lets out about that time. I know from the past if I just hang there they come up to you asking for some money. If the vibe is right and we get to talking I make a offer. Sure some times in my college days I'd be shot down or may have to get out of there but thats very few. Mostly they do what they need for what they want. Finally that day a man that caught my eye came up to me not asking for money but just wanting to chat. He was right on what turned me on. Most likely mid 60s, long gray stringy hair, long unruly gray beard, real skinny. He was missing a few teeth I know it's strange to some but that really gets me hard.
So after I assessed he was pretty with it I came out and told him what I wanted. For breakfast, carton of his choice of cigs, and a liter of booze he would let me blow him then get me off however we decided. He didn't hesitate for a second and agreed. He told me his name was Larry(real or not I don't care). We went back to my room at the hotel.
Yes walking in we got odd looks because it was a pretty nice hotel. We got to the room and I ordered a feast of food. When it came and the room service guy left I told him I want to watch him eat naked. He undressed and my cock sprung into heat. His ribs showing, cock uncut with gray unruly matted pubes, stringy armpit hair that peeked out. He sat on the bed while I sat nude on the chair playing with my cock and nipples. He stared at me while he wolfed down the food. His blood shot eyeslooking at me with his toothless shiteating grin.
When he was done he opened the vodka and took a swig. He wasted no time and got his cock in front of me and said it was time for mine. I peeled back his foreskin and went to heaven. The smell took over my nostrils and the sight of the smega got me so hard. I took his cock into my mouth and started to lick around the head. It tased so good what with the salty sweat that had been there. As I blew him he reached down and started touching my nipples. In under a minute he came down my throat and in my belly. He backed away and chugged some more booze. He asked me how I wanted to cum and I told him. I had him sit on my face smearing his ass on it while he played with my nipples and I jacked myself off. I told him to smother me with his asscrack. Oh god was I in heaven. Did not want to to end. I edge myself while he sat there wriggling on my face smoking and chugging vodka. When I came I shot up over my chest into his chest.
After laying there spent on the flloor I asked if this was hard for him to have sex like this with a guy. He identified to me as str8 but said anytime I needed more for what I gave him he would oblige. We actually spent the rest of the day in the room and yes I got wasted with him.. Being wasted we tried to both cum again but to no avail. Instead I just enjoyed the flavor of his balls, taint, pits, feet, ass!! He gave back by working my nipples and tickling my feet. Yes another fetish of mine! The next morning he told me his haunts and shelters and I gave him a hundred bucks.
I will be back. Looks like a new little homeless whore for me!! Shane