Crossdressing Bet Stories

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Infinite Scroll

Locker Room Fantasy - Sequel

by boyboygirllove on Mar 20, 2018
Group Sex

I try not to focus on the clock counting down my workout as my feet pound hard against the treadmill. Sweat rolls down my back and into my ass crack at a steady stream. Through the burn in my lungs and muscles my mind remains fixed on what went down in this very gym a month earlier. My first sort of mmf, an unexpected threesome with two men of questionable s...

Soccer Mom

by Sfbullrider on Apr 24, 2018
Loving Wives

I am a daughter, a granddaughter, a mother, a wife, and a soccer mom. For the last 18 years I have been a good wife, mother, daughter, granddaughter, and soccer mom. I love my husband and my family with all my heart. My husband Jim is the salt of the earth. My daughter Julie is the best child any parent could hope for. With that being said, I did something s...

Gap Year

by XtinaSmith2017 on Jun 19, 2018
Transsexuals & Crossdressers

With a low sigh, Charlie ran the back of his hand across his forehead, collecting the beads of sweat that the Brazillian heat had gifted to him before wiping his hand on his already quite sodden T-shirt, looking down at his open luggage on the rather meagre single bed with a serious lack of motivation. He should unpack, find his toiletries and find the sho...

Lost Bet on Vacation

by softly_spoken on May 1, 2018
Group Sex

This is my first submission. I welcome feedback. I hope you enjoy! ***** I had first gotten together with Rachel 10 years ago in college. I was a Biology nerd, fit from running cross country in high school. Rachel was a sci-fi geek with a bubbly personality, but somewhat conservative in dress. Rachel revealed that she had not enjoyed the attention her 32 D...

Shemale Shopping Spree

by tawnysuede on Sep 19, 2017
Transsexuals & Crossdressers

She-Male Shopping Spree featuring Chelsea and Victoria, two gorgeous chicks with dicks - and an attitude! by Mistress Tawny Suede "Oh god, I feel so incredibly horny!" said Victoria. "Well, sugar, if we hurry back to the apartment, I've got just the cure," said her best friend and roommate, Chelsea. Victoria looked the stunning black girl in the eye a...

Kiss of the Spider Woman Pt. 04

by voluptuary_manque on Sep 25, 2017
Sci-Fi & Fantasy

"Excuse me?" Kyle McAdams turned around in surprise at the sound of a familiar voice. There, leaning out of the window of a well-worn Prius was Lara. Surprisingly, there was no sign of Josh. "Hi, Lara. What brings you out here?" He waved expansively around the orchards on both sides of the gravel road. In the past year much had changed. The ground beneath...

The Servicemen's Club Ch. 02

by NeedYou on Sep 13, 2017
Mature

John told his beautiful wife he was going to take her to a place where they could eat and then dance. He knew she loved to dance and when he told her they were going to do it tonight she became all nice and warm to him while they dressed. John asked her to wear her short black dress he loved. It had a low cut top and was short 5 inches above her knees. "You...

Park Birthday Surprise

by LitEroCat on Sep 19, 2017
Exhibitionist & Voyeur

© Literocat 2007, 2016 [This tale spans exhibitionist, group, swinging, shared wife and more wrapped in a surprise.] Years before OGC and OFC (Our Groping / Fucking Club), while my Sue was still feigning modesty and propriety and before I figured it all out, I had the challenge of creating a near-surprise birthday party for her. I was never sure if she was...

New Order of the Ages

by SEVERUSMAX on Sep 26, 2017
BDSM

August 25, 2028, Tampa Bay, Florida Daniel "Dan" Orsini downed another pint of the best microbrew along the coast, as he saw it, anyway, as he saw his twin brother Bruno "Dale" Orsini enter the bar in a much better mood than before. He didn't know what was going on, exactly, but something told him that he was about to learn. Something was up, and he resiste...

Janie in Alaska Ch. 03

by divergirlxoxo on Aug 31, 2017
Erotic Couplings

My summer in Alaska was turning out to be quite an adventure. I caught a 126 lb. Pacific Halibut, went bear hunting, learned how to fly fish, and had amazing sex just about every night with either Mike or Neil (and sometimes both!). I had been hired as a fisheries technician at a remote salmon hatchery, and in the gender minority, found myself surrounded by...