Last week fixing a young gay couples heating system, I had to do more work than I first thought. It took me an extra day, but the guys said they'd sort me out. Finishing the job I was given the money they owed me, but then older of the two asked me if I'd like to double my earnings. Thinking it was another job, I said yes. Escorting me into their bedroom, I came across the sight of his younger lover knelt up on the bed naked, and his arsehole was covered in lube. Looking around to the older man, he smiled at me and said "Jake would love you fuck him, so would I. Double your money?". He left his comment hanging as a question, but and this is the strange bit to me, I was already erect.
With his older lover still watching, I dropped my trousers and underpants, shuffled over to the lad and took the condom he offered me. Putting it on not only thinking of the money, but actually getting my rocks off up a guys arsehole. Holding his hip with one hand I guided my cock into his hole and just went for it. In my mind I figured who would ever know and I'd have twice as much money, just for fucking a young mans arsehole.
Shagging him as hard as I could, the older man left us for a short while then returned and began to encourage me to fuck Jake harder. He even put his hands on my arsehole pushing me into his lover. Unfortunately as I was enjoying myself so much, I didn't last too long, maybe ten minutes or so before my cock erupted filling the condom deep up his hole. Pulling out I slipped the condom off and was about to toss it into a small bin. The older guy took it from me and gave it to the young guy I'd just fucked. At the same time he dropped his shorts and slid his already hard cock up his lovers arsehole. Turning to me as I watched the younger lad suck out my cum from the condom, he told me the second envelope with the money was on the side by the front door, and I could let myself out.
Sat in my van outside, there was indeed exactly double the money in the second envelope they'd given me and little note. It reads "Thank you for your services. Jake and I are more than happy with the work. If you've got this envelope then you've just fucked Jake x We both hope to see you again soon". I already had their mobile numbers, so the last bit made sense "Text us if you'd like to visit again, no work required x".
I haven't text them so far, but my wife told me I had a message left on our home's answer phone. It was from the boys once again thanking me for a job well done. I knew what they were getting at, but obviously all I said to my wife was I'd done the extra work.
I've not put myself down on here as bisexual as it was a one off. But I guess and I'm seriously thinking about it, if I do revisit them, I suppose that would mean I'm most definitely bisexual. Jakes arsehole was after all a much better fuck than my older wife's grey haired loose pussy.

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Anonymous

by Anonymous on Oct 20, 2017 at 9:32 AM

I fucked a guys ass for the first time last year. I'm 52. It was much much tighter than my wife's pussy. After having three kids I can say my wife's pussy isn't the same. It feels looser and she has a full natural bush that pretty much hides her pussy. Don't get me wrong I love sex with my wife but when the opportunity presented itself for me to fuck a 28 year old in the ass on a work trip I did.

He's a coworker, he came to my room one night on a work trip. I was in just my underwear as it was night time and he came knocking on my door. I put the hotel robe on and opened the door. He needed some help with a assignment from the training class. I helped and he said he repay me for it. I was like how, he stripped down to some cute American eagle boxer briefs and said I'd like you to fuck me. He asked what I had under my robe and I said I'm 51, just some white briefs, I don't wear fancy underpants like you young guys. Well he got naked, got on the bed and presented his asshole. It was hairless and tight! He said are you gonna do it. I took the rob off, kicked my underwear off to the side and my hair uncut cock was already hard. I'm 7.5" and he said dang your big.

We had no lube so he said grab the conditioner out of the shower, that will work. Put some on his ass and went to town. I last only like 5 minutes before cumming in his ass. Haven't been with a guy since but I'm craving it.

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Anonymous

by Anonymous on Nov 9, 2017 at 8:04 AM

I was a painter/paperhanger in my twenties, married also. The large company I worked for had a contract with a large hotel. I never thought of myself as gay, maybe a little bi due to some youthful indescretions.

I knew that I had a nice ass, my wife said so and a lot of the gays that frequented the hotel loved to watch me work, getting excited then run to their rooms and suck and fuck each other. I know because I was told that by an older gay couple that frequented the hotel saying; "every one of their friends has heard about the sweet ass on the teenage painter at the Hilton and they can't wait to hear all about who gets in his cute little boypanties.

"Wow!" I thought, they think I'm in my teens and have a hot ass. Sure I knew that I was a tease in a way. I'd wear white string bikini underpants under my white painter pants, and I knew they'd show a little, white under white. It got me excited and my wife got a real kick out of it thinking about all these older gay guys wanting to get in my pants.

Well curiosity won out and I got first verbally seduced by an older couple, friends of the couple that revealed the lust for my ass. I went to a get together for their friends up in their suite at the beginning of my night shift, nobody's gonna know. I'd been invited the night before and I was squeaky clean and fresh in new whites, both underpants and Bibbs.

It was sureal, the whole party ended up in their underwear, an assortment of manpanties, from see-throughs to metallics. I was the only one in white cotton. My firm twink's bubble but was proudly coveted by all there. I was seduced by all hands on deck, as the joke was my ass was the deck. I first visited the bedroom in the two bedroom suite with the tight guy in the black and gold metallic bikinis. His size was modest and he just looks looked so good. I was his and he knew it. He gently fuckd my inexperienced firm tight fleshy cheeks my manpanties around one ankles. I panted, wiggled and squealed in excitement, my first mancock. I lay weak-kneed and my lover took my string bikinis, told me he'd be right back and I could hear the cheers as he walked around the room showing all. I wasn't virgin, but nobody knew that, I'd only been with other boys, I wanted to be with a man but was too shy.

Back in the modesty of my freshly fucked white cotton underpants I gushed and blushed at the pats on the ass and propositions I received back at the party. Yes, I did visit the bedroom three more times that night. Alcohol stripped my inhibitions and my finish was a BBC that I suckd and rode like a good little boy bitch. I went home to my wife my once fresh ass numb with cumm wearing another guy's manpanties, pink with lots of lace.

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Anonymous

by Anonymous on Nov 14, 2017 at 8:06 AM

I worked as a handyman when I was in Art school. I'd developed quite the clientele of middle-aged gay men, some married that either were or wanted to fuck me. Once it happened it became easier.

The first time it was a couple who'd I'd been teasing with no intention of letting either one of them have sex with me. My girlfriend got a kick out of how many gay guys were always hitting on me. She encouraged the teasing I did to get tip's for the simple odd jobs I'd do.

An athletic shirt,short tight cutoffs and these old gay dudes would get all excited. After having a few drinks after I'd finished a small job and was paid triple and tipped to boot, something I wasn't used to, drinking. I ended bottom up tighty-whities around my ankles having my twink's cherry ass busted for my hard, painful first. They both rode my drunk unsuspecting twink's cheeks that night and I went home with my tighty-whities dripping cum.

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