Gay Unexpected Stories

1,772 results
Orientation
Length
Source
Infinite Scroll

Unexpected Pleasure

by tomguy12345 on Dec 10, 2019
Gay Male

I had been working in financial services and banking for about 25 years. It was good. It put food on the table and kept my wife and kids happy with the things we could afford. I lost my job in the financial crash and we really struggled to make ends meet while I looked for new work. It made me appreciate how quickly it could all come to an end. Finally I f...

The Lady's Gift

by apmoraez on Jan 21, 2020
Gay Male

NOT FOR THE first time in the last hour, the thought that maybe — just maybe — leaving his house to take a look at the festivities hadn't been such a great idea crossed Luke's mind. He gave himself a reprieve from the colourful fanfare and closed his eyes. The deep breath helped him get a grip on the pain radiating from his left leg after exerting it more t...

Brotherly Love

by DaFreak on Aug 31, 2017
Gay Male

I never considered myself to be gay, but I do remember a point in my latter teen years when I found that I was attracted to the male body. I don't know if it was my fascination with my own developing body or what but I was always curious. I vividly recall my first "gay" experience, which happened when I was 18. This happened with my brother who was a year ol...

An Unexpected Encounter

by gastonbunn on Aug 18, 2017
Gay Male

Hi Naughty Readers! I am Gaston B., a single man in the mid-fifties. By the way sorry for the 'naughty' but am a very naughty guy as far as sex is concerned; may it be with guys or women. However, it was not always the same with men. In fact, I was born is a very conservative town, in a very conservative family. For my part I didn't mind gay people as long...

Daddy-Boy Love

by Shale on Nov 20, 2018
Gay Male

October 28, 2018 It was a bright sunny day with a pleasant sea breeze at our Clothing Optional Beach in SoFlo in July 2002. I was taking in the sun and talking to a few friends when this really cute young man approached me and said he found older men like me so attractive that he just had to meet me. Well, what can I say to such a forward and cute young m...

Beach, Bed and Beyond Ch. 02

by paul81219 on Oct 6, 2020
Gay Male

I heard my name being called from the end of a long, dark corridor...or was I at the bottom of a deep well? "Paul. Paul." The voice got louder and the light brightened as I emerged from the deepest, soundest sleep I had ever experienced. "Wake up baby, I have to go and so do you. You've got half an hour." The voice was Daniel's, my 35-year-old lover who...

Short-Term in Chicago

by markindy on Sep 14, 2017
Gay Male

I was thirty-five, my girlfriend of five years dumped me for some loser that worked at a grocery store, and my job wanted me to take an assignment in the windy and cold Midwest to evaluate some key suppliers. Leaving California for Chicago wasn't my dream scenario, but it was only for three or four months, and right now I felt I could use an adventure and a...

The Meat of Our Relations

by farless on Aug 17, 2017
Gay Male

I have a birthmark on my ass which my boyfriend liked to comment on frequently, and sometimes in public places. Matt, my boyfriend, also liked to wrap his arm around my slim waist and hip check me up in the air. I think he did it just to remind me that I was smaller than him. Other than that, it's what I expected from a college relationship. That is to say,...

My first Bumming

by Peter Vincent on Aug 18, 2017
Gay Male

My name is Peter, and last year I was at my lowest, I had split up with my wife after being together for 5 years, and my kids had been taken away from me. I was a single, 33 year old male leaving in a small estate in the North East of England. I thought things couldn't get any worse, but then things took an unexpected, but pleasant, twist on the night I me...

Should Have Known Better

by knowsbetter on Sep 14, 2017
Gay Male

A beautiful spring day, one of those early warm ones where suddenly there's a lot of unexpected skin everywhere, and you can't not look, and I'm stuck at the library studying. Girls are lying out in the sun untying their bikini tops and I cannot focus. The buzzing of too much coffee and not enough sleep and oh god those shorts she's wearing are so small. J...