Gay Anal Gaping Stories

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On a Run Ch. 03

by yeaimbored on Sep 16, 2017
Gay Male

I lay with my back on the bed, holding my legs spread apart, feet next to my head. I had on my usual uniform for when Will fucked me: a bra, a thong (pulled off to the side), a short skirt, and heels. Will took a bottle of lube, put it up against my ass, and squeezed, almost giving me a lube enema. Once he was satisfied that my ass was slippery enough, he pu...

Becoming Jessie's Bitch

by HerLittlePiggy on Sep 14, 2017
Gay Male

I awoke slowly as bright light streamed through the open window beside the bed. My wife was away on business for the week but I was not alone. My cock was hard and ready despite the vigorous activity from the night before. I turned onto my back and it jutted skyward tenting the covers as I reached beside me and touched my companion's warm flesh. My right h...

Learning a Lesson

by tommyrj on Aug 18, 2017
Gay Male

When I was around eighteen years old I worked for a newsagent, sorting and delivering papers. One day, as I got back a bit later than usual. I went round to the back and picked up my bike. I noticed a newly arrived stock of porno magazines, and to my surprise, there were some gay ones. I was Curious, and not sure what I liked at this point. Girls were fun, b...

A New Flame

by Robert_Furlong on Aug 18, 2017
Gay Male

=== Warning: contains raunch. === It was after yet another failed attempt at lovemaking that things really changed between my girlfriend Debbie and me. Until then, Debbie's interest in the lower half of my body had been lacklustre to say the least. She complained that I needed sex too often, that I came to bed too sweaty or that the head of my cock stunk l...

Both Ways

by Robert_Furlong on Aug 31, 2017
Gay Male

Part of the 'Butt Monkey' series of stories by Robert Furlong === At first I was convinced my ex-wife was in the bed with me. It was Sunday morning and I was in that half-dreaming half-dozing state I sometimes end up in when I've slept too long and I really should get up. I'd opened an eye to check the alarm clock a couple of times and, even though it wa...

Doubling Up Pt. 03

by Robert_Furlong on Aug 30, 2017
Gay Male

It felt odd for my son and me to be squatting naked together, his back rubbing against mine, but I was sure it must feel even stranger for his best mate Marcus who was lying out on our front room carpet, facing upwards at our two splayed bums and pressing the twinned heads of a double-ended dildo against each of our arseholes. It wasn't the most typical Sat...

Would I Have Liked It Ch. 02

by trubrit on Aug 18, 2017
Gay Male

Continuing the search to find an answer to my curiosity about bisexuality, and myself! After I left the Navy all thoughts about my bi romp in New York were pushed to the back of my mind. I married a lovely girl; we had two adorable children and settled into a life of married bliss. Some years later I was working in London's Soho district when I saw a guy wh...

Doing the Dirty Pt. 02

by Robert_Furlong on Aug 30, 2017
Gay Male

It's odd but strangely compelling to watch your own son masturbating right there in front of you. I was fascinated to see how different his technique was from my own - his hand seemed so much more frantic and his fingers more agile - while marvelling at so many physical similarities between us. His cock was ever so slightly bigger than mine, but other than...

Surprise First Anal Experience

by BottomBoyUK on Jul 9, 2019
Gay Male

I was 21 and had just finished at university. I knew I was into cock and had sucked one before but had been too nervous to take one in the ass. To me it felt like crossing a threshold into being gay that I wasn't sure about. I had been chatting to a man called David online, who lived in my town for months by this point, and he made me feel comfortable enoug...

First Gay Experience

by rickyjonesbottom on Aug 8, 2018
Gay Male

Leaving high school and going to university, I believed I was completely straight. I came from a sheltered middle upper class upbringing, but was raised to be cheap. I dressed poorly, and was starting to become overweight. My first year of university, I gained weight. I started noticing less girls smiling at me and eventually started working out and going...