Lost Bet Girlfriend Stories

201,764 results
Orientation
Length
Source
Infinite Scroll

Sun Hee's Cruel Tease Ch. 02

by metalimbic on Sep 25, 2017
Fetish

Feeling blue balled to hell and desperate to put Sun Hee's sexy little body out of my mind even for a moment, I spent Tuesday evening at the local pub playing billiards with some of my friends. Rick's Bar & Grill a few blocks from the university campus was one of those places that serves shitty food and even cheaper beer, a regular dive for rundown locals ex...

Neighbourhood Terror to Sissy Pt. 12

by Fibaro on Sep 9, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** Chapter 14 On Monday morning Mark got woken up rather roughly. It was only 7:30 am, but his phone was going off loudly. Confused he picked it up to see who would call at this ungodly hour. Nerves instantly struck him when he saw his girlfriend's caller ID pop up. What ha...

Big Mouth Strikes Again

by fantasticfic on Jul 13, 2020
Erotic Couplings

"I spoke to my sister last night. She wants us to come up to stay next week," said Cat as we lay in bed on a lazy Sunday morning. "Our parents are away." "Oh?" I said. I was aiming for studied nonchalance and I might have got away with it if Cat hadn't been stroking my dick. We both felt it twitch. "Yeah," she said with a smile. "She asked after you." "Oh...

A Friendly Game of Strip Poker

by mghbc on Sep 12, 2017
Group Sex

"Are you sure you want to do this?" Leila asked everyone around the bed. "I doubt Mark does" Maria laughed. "He loses at this almost every time." Everyone seemed to breath a sigh of relief, knowing someone else was probably worse at cards than they were. "Yeah, you just wait and see" Mark proclaimed confidently. "Now that there's more on the line, my skil...

Pool Room Slut

by Sara T on Sep 17, 2017
BDSM

(Ok boys and girls, this is my first stab at fiction. Although it has been a fantasy of mine for a long time, I'm not sure I could be that degraded. Maybe some day I'll find out, but until then here is the fantasy. Please let me know if you like the story through feedback and I promise to answer all email.) The sound of the belt got her attention as she cou...

A Job Too Far

by JamesMiehoff on Jun 5, 2019
Sci-Fi & Fantasy

Copyright (c) 2019 James Miehoff, All Rights Reserved. This work may not be published whether for fee or free without this copyright. ------------------ This was supposed to be an entry into the 2019 Geek Fest Event. Real life intervened and, well, here we are. I hope you enjoy it as much as I enjoyed writing it. The protagonist in this story is a member...

Freddie Becomes a Cross-Dresser Ch. 04

by BOSTONFICTIONWRITER on Sep 16, 2017
Reviews & Essays

Now, that I bought everything that I needed to transform myself from a handsome and modest man to a beautiful and sexy woman, I realized that I had completed the easy part in buying the clothes, the makeup, and the perfume. The difficult part, of course, would be dressing up like a woman without having a woman there to help me. I certainly did not want to as...

The Prize

by damonX on Sep 25, 2017
Anal

I held my breath and closed one eye as I slowly drew my arm back, feeling the smooth wood gliding easily over my hand. Keeping my vision intently locked, the pool cue shot forward, striking the white ball sending it rolling across the table. "Come on!" I muttered to myself as the cue ball just nicked the 8-ball sending it rolling towards the corner pocket....

Indecent Betting

by P4U on Sep 13, 2017
Loving Wives

Rakesh and Rukmini were a happy couple till Kevin moved in next door. Within days Kevin had struck friendship with Rakesh and they would often sit for hours talking. For Rakesh, Kevin was a rich but nice enough guy in most ways, but a blowhard, always bragging about his sexual exploits. Then one day he went too far when he said, "I can have any woman. There...

One Pump Chump

by Gaius8666 on Sep 12, 2017
BDSM

Desiree was stunningly beautiful. The several strip clubs she owned, and occasionally performed in, were wildly successful and major generators of cash to her ever growing bank accounts. Owning such a profitable venture, and running it with the efficiency of the sharpest mind on wall street had made her incredibly comfortable very early in life. Having gro...