Gay Loser Stories

481 results
Orientation
Length
Source
Infinite Scroll

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...

Winners and Losers Ch. 12

by bawdybloke on Sep 15, 2017
Gay Male

If you have missed the previous installments the premise of the story is that after a football match, the losing team must provide sexual relief for the victorious players; the narrator has recently admitted his bisexuality to himself, his team and his fiancée. Previous chapters for Winners and Losers are on Literotica * * * * * My "coming out" to my team...

Technical Difficulties Episode 07

by LucyH on Sep 14, 2017
Gay Male

While Trisha poked around in the detritus on the lake shore, Ryan lay on their picnic blanket with his eyes closed and listened to the lapping waves and seagulls. He and Trisha had the beach almost all to themselves that afternoon in October. It was the first time since his father's visit that he'd felt really peaceful, and Ryan wanted to soak up as much of...

Becoming a Gal Friday Pt. 02

by Showoff888 on Sep 14, 2017
Gay Male

Here I am a normal twenty year who had everything, living with this thirty year old babe who loves to be fuck, working at her law office, living with her. An ideal gig and then wham! She dumps me for some rich guy her own age. So things were getting desperate for me and I had to find a new job and place to live. That's how I came to be getting drunk, sitti...

Just a Quickie

by Glenda100 on Aug 18, 2017
Gay Male

I was away from home. Work had suddenly sent me to Liverpool (I live in Surrey) so I hurried home, packed a bag and hopped on a plane. I arrived at my hotel, threw my bag in my room and went to the office. I fixed the most pressing problem then left for some dinner, saying I'd be back in a few hours. Back at the hotel I unpacked. I guess I should point out...

Breaking In Pt. 02

by Iamkrazy4 on Dec 24, 2019
Gay Male

After laying on the ground for a few more minutes, I got up, grabbed my phone and headed to my bedroom. I quickly unlocked my phone and watched the video of what had just transpired. My dick immediately got hard, but instead of taking care of it, I slipped two fingers into my still lubed ass and fingered myself hard for the duration of the video. I spent a...

Teachers Pets Ch. 02

by MelvinMhk on Aug 30, 2017
Gay Male

The next day I was late, as we both expected. But about four minutes after I arrived, Sara came walking into class. "Miss Thompson?" Professor Samuels asked. "Yes Professor." She replied. "Why are we late today?" "I sort of over slept." "No Sara, you did over sleep, not sort of." "Yes Sir." Sara took her seat. The bell rang after class and I sat there...

Office Confrontations Ch. 01

by fexcellent452 on Sep 14, 2017
Gay Male

[[Be forewarned, this is not a straight-to-smut story. I myself prefer plot-driven stories, so that's what I write. Any and all comments welcome ^_^ and yes I know the title sucks, my creativity dies when confronted with story names]] * "I hate that son of a bitch." Marshall ground out, glaring at the tall, dark-haired man two desks over. His back slumped...

Three Strikes Ch. 16

by Mrsgnomie on Dec 10, 2018
Gay Male

I set the bag of alcohol and mixers on the table, along with some beer for the heteros. It'd been a very long week, as far as work was concerned. I'd worked over sixty hours, thanks to others taking vacation time or calling in for this reason or that. I was exhausted, but there was no time for that. It was time to square up on our deal and I had all weekend...

The Loser Takes It … All!

by laurasfox on Mar 13, 2018
Gay Male

Author's note: This is a small fantasy I wrote for the Yuri on Ice!! Fandom, so a little introduction for all the characters involved may be in order. * Yuuri Katsuki -- the main protagonist of this gangbang story, he is a Japanese figure skater. He is a hard worker, but because he gains weight easily, he needs to make a lot of effort to stay in shape. He...