Losing Bet Stories

101,365 results
Orientation
Length
Source
Infinite Scroll

Love Is Blind Ch. 3

by AnonSky on Jul 15, 2020
Romance

Allison slipped quietly from the bed, being careful not to awaken Brad, and went into the living room. Galahad immediately came up to her. Picking up her watch, she opened the crystal cover and felt the numerals and hands. It was 7:35 a.m. "Are you ready to go out," she whispered. She went over and opened the sliding glass door to the small patio and the ju...

Kasey's Legs Ch. 05

by KaseyLegs on Sep 19, 2017
Transsexuals & Crossdressers

I ended up feeling good after my big day of showing up for work in short shorts. I didn't really know what to expect when I left for work that morning, but I just didn't want to hide any longer. Guys had teased me and made jokes about me, but after I caught them wagering on whether or not I was a cocksucker I blew the biggest jerk working in the warehouse....

Cindy Gets The Upper Hand

by EnCarta on Sep 12, 2017
Erotic Couplings

Jeff was having a hard time keeping his eyes off the voluptuous new temp who had been working for him for the last week. Cindy Ames was perhaps 10 years older than he was, but all the young guys in the office had their tongues hanging out whenever she was around. Cindy was a stunning woman with a breathtaking figure. She was a tall redhead who may have been...

A New York Tale Pt. 03

by neuromancerzero on Mar 27, 2019
Fetish

I wish I could tell you that I had woken up to a blowjob, but that's a thing of fiction. We didn't wake up cuddling, she was on the other side of the bed, the left side. I was on the right side, I normally slept on the left, so sleeping on the right caused me to wake when the sun shined into my eyes. My stomach growled and I quietly got out of bed. I grabbed...

March Madness Ch. 03

by jbirdman on Sep 13, 2017
Transsexuals & Crossdressers

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), teasing & denial, chastity training, mild bondage, creampies, cuckolding cross-dressing and a few other fantasies of mine. I hope you find it entertaining, but if you might be offe...

Last Friday Night Ch. 02

by bitexwriter on Sep 12, 2017
Group Sex

The week after our amazing night with Rick and Tonya was interesting. Margo and I fucked like crazy, but there was a slight tension to it. We tried not to talk what happened about too much, but it came up frequently. Margo was worried that she had let everything get out of hand since she started the festivities, and I was worried that she wasn't comfortable...

Teaching Assistants CH. 02

by Eli is Coming on Sep 12, 2017
BDSM

[Chapter one is located in the Transsexual/Crossdressers category.] ANNA The following afternoon as was custom Xander and Anna met for coffee before their Latin America class. Both were punctual to a virtue but this time she was early, giving her the pleasure to find him walking through the door. Well, walking was not the proper word for it, more like hobb...

A Honeymoon Affair

by Awful Arthur on Sep 19, 2017
Mature

"How'd you like to get hold of that?" Roger Goins asked as he stirred his fresh drink. Roger was one of those guys who always talked about strange pussy, but never seemed to make an attempt to get any. He was too pussy-whipped by his wife, Elaine, to take a chance. Me, I was on the look out all the time—but so was my wife, Shirley. It took about fi...

Virginities Lost Ch. 3

by Leo Davis on Sep 14, 2017
Group Sex

Pt. III: Taking Charge Carol and I had simultaneously lost our virginity three weeks before, and we had re-discovered the missionary position three separate times. I had also masturbated her to orgasm a couple of times, something she admitted she had never done for herself. As soon as I got off work the next day I called her, and got some really bad news....

Nina and Renee Return Ch. 05

by wet_special on Sep 14, 2017
Sci-Fi & Fantasy

The series continues. ((*Spoiler alert*)): If you like the tension going on between Kirsten keeping her dad sequestered in her room, and you wonder whether they're going to get frisky, well, here's what happens. If you would rather not know, just skip to the next paragraph below. I'm about to give it away now. Okay, here goes. No incest. Sorry! * The ship'...