A Walk On The Wildside

The past few years have shown a marked increase in my letting go with gay desires and urges. It used to be after my divorce I would occasionally give in and have a sexual encounter with a man in an ABS,park or bathhouse. I lived in a big city until 2 years ago and these places to have anonymous sex were east to find. Mostly I sucked cocks and received oral usually with older men which is my preference. I recall one day walking down the street just before I moved from the big city and a homeless man bummed a cigarette off me. He had scraggly hair,a similar beard and a scrawny physique. He had to be in his late 50's but looked older. As we smoked and talked I noticed him eying my crotch. No matter his looks and way if life I got horny from his attention. He saw my erection and he offered me a blowjob. I looked around as it was evening and there were lots of folks about. He told me there was a place nearby behind a building near a dumpster where he could suck me and no one would see. I felt pangs of forbidden lust and agreed to go with him. I took one final deep drag on my cigarette and off we went. We got to the spot and he took my pants down. My cock was incredibly hard as it felt nasty and erotic to let a homeless guy blow me like this. He got on his knees and deepthroated my cock. It felt crazy good and after he sucked me hard for a few minutes he ate my big load. He took down his pants and showed me his cock which was a good size and semi hard. I knew I had to suck him dry. His cock tasted salty but I loved it. I sucked him hungrily until he spurted his cum. Took every drop. After we were done we shared a cigarette and he told me he hoped to see me again. He let me know where to find him as he lived in a downtown shelter and often hung around outside there.

I moved to a smaller city a few months later but had not forgotten this wild and crazy experience. I masturbated frequently thinking about it and about hooking up with this homeless guy again. Nobody in my life knew these secret desires and I just acted normally at work and in my life.

After a few months in my new condo and city the desire to relive this experience took over in my mind. Rather than drive I took a train back to the big city and went to the shelter where he lived. It was the morning and sure enough he was outside smoking. He was surprised to see me I told him I had a plan for us. I would rent a motel room for the weekend for him and me. We would get take out and have sex in the room. He was thrilled and I flagged down a taxi. We got to a small motel and I got the room. We got naked right away. I sucked his cock dry then he did the same to me. We showered together and as he relaxed in the room I went out and got us some pizza. After eating pizza and watching some porn we both got horny again. Thus time he begged me to fuck his scrawny little ass and I obliged mounting him from behind and blowing my seed deep into his ass. I felt so into it when fucking him it was a feeling I never quite had before with a man.I scared myself as I realized I could fall in love with this homeless guy. The more I tried to repress this feeling the stronger it got. That night in bed with him I got that feeling again and got a hard on. I got on top of him and fucked him missionary as we kissed sloppily. I had the most intense orgasm of the day this time as the love feeling took me over. We spent another day at the motel and I bought him some new clothes. I told him I wanted to come down every weekend,rent this room and have sex with him. He lived the idea and we started spending every weekend like this. Loving each other just took over. After almost 2 years some weekends I just drive to the big city and pick him up and being him back to my condo to make love here. I no longer care who knows I have him as my lover.

Comments

Anonymous

by Anonymous on Aug 31, 2025 at 7:35 AM

Your story has produced a raging hard on in my pants. The nasty forbidden nature of it combined with your now ongoing sex and loving with a homeless man is activating my deepest desires.

A few months ago I had a similar experience and am now feeling compelled to repeat it again and again. I have had sex with this homeless guy 6 times now and last night he shared my bed for the first time. He is still sleeping after we had sex last night.I am falling deeper and deeper into a forbidden love.

I am in my early 20's and never thought I would get into anything like this. I had seen this homeless guy for over a year asking for money on a street corner near my apartment building. I felt real sorry for him and gave him money regularly. He is older than your guy probably around 60 and quite a bit chubbier with grey hair in a ponytail.

One day he told ne it was his birthday and he felt sad no one was there to celebrate it with him. That touched me deeply so I rented him a motel room for the night got him some take out,even a birthday cake and some nice wine. I ended up staying in the room and one thing led to another and after kissing me he blew me in the bed. He sucked me several times in the night and in the shower together the next morning I sucked his cock and swallowed his load.

I couldn't stop thinking about him after this and now I am bringing him home to have sex in my bed. He now fucks me with his sexy cock and his spunk fills my ass. I am afraid others in my apartment building will find out we are lovers but now I am so into him I can't stop.

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