Caught Dressed As A Girl Stories

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Infinite Scroll

Capri an Isle of Love Ch. 03

by walterio on Sep 16, 2017
Group Sex

INTRODUCTION This story is a sequel to a Marine's experience on the Isle of Capri. In this chapter Walt continues his adventures with his Italian friend Paolo and has other erotic experiences. These experiences take place in the Naples, Italy area (Napoli, Amalfi and Capri). If you didn't read the previous chapters just note that this took place in 1960 – 1...

The Performance

by HStoner on Sep 12, 2017
Exhibitionist & Voyeur

My characters and their names are entirely fictitious. Any similarity to any real person is unintended and coincidental. Thank you for reading. ***** Jim, Helen, and I had gone to college together, many years ago it now seemed. Jim and Helen were already a couple when I met them. Like me, Jim and Helen were both history majors. While Helen and I focused on...

Fight! Fight!

by JimBob44 on Sep 17, 2017
BDSM

**Author's Note: Any and all persons engaging in sex in the following story are at least eighteen years of age. Apalachee Cloud squared off against Emily St. Martin, ready for this fight. It had been brewing for a few months now, ever since Christmas break ended. Emily had been teasing and taunting the overweight girl nonstop and Apalachee had decided to...

Crystal Clear Ch. 17

by Romantic1 on Sep 15, 2017
Group Sex

This story is part of a continuation of my Road Trip series (see the end of 'Road Trip -- California' for a list of the chapters of that series, in the order to be read). You need not read that series to enjoy this series. Although real places and celebrity names are used for realism, this story is fiction. Please 'read, enjoy, vote, and comment.' Synopsis...

Pretty Little Summer Dresses Ch. 07

by Mylipstoyours on Oct 30, 2018
Group Sex

It was the day of the reading of Aunt Marjorie's will. When I arrived at the solicitor's office I was shown through to the office of Nigel Pevensey who, I was informed, was the executor. I was shocked to see my ex, Naomi, sitting there with her new fella. She nodded to me and I nodded back, thinking "What the hell is she doing here?" Apparently, it was just...

Germany Confidential Pt. 01

by The Avenger on Sep 16, 2017
Interracial Love

Dez was happy with all the pussy and ass he was getting, but he missed a girl of his own. Deep down, he longed to have a woman by his side, an intelligent, but cool woman to make his wife, that he could share his life with. He had Trish, Angela and a lot of girls. But they didn't belong to him completely and they had an independent streak. He also did not wa...

Cheryl's Passion Ch. 17

by Schlank on Apr 20, 2020
BDSM

Doctor Booth wasn't the first woman to put me over her knee, far from it. I'd been spanked by several women, however, when Doctor Booth ordered me across her lap, my heart sped up and I felt both mortified and sexually aroused at the prospect of being spanked by her. I embraced my helplessness as I slid my naked body across Doctor Booth's thighs. The fabric...

Tricked with a Pill 2.5

by FCat_X on Aug 7, 2018
Transsexuals & Crossdressers

This story was inspired by characters and situations created by Jackie_Em. I thoroughly enjoyed the two "Tricked with a pill" stories, and just wanted to flush out what went into Andi's decision to remain a woman. This story begins the morning after Andi learns that Bill has procured the blue pill. ----------------------------------------------------------...

The DReAMers Pt. 02

by Ian56 on Feb 6, 2018
Romance

The girl stood on the shore with her long rustic hair blowing in the onshore breeze as she spread her arm's wide and closed her eyes with the sea lapping around her bare feet. She smiled and breathed deeply of the brisk fresh air as she listened to the sounds of the waves crashing on the rocks in the distance. Behind her, on the beach, the people were enjoy...

A Fishing Trip, But I'm The Bait Ch. 03

by stickygirl on Sep 12, 2017
Transsexuals & Crossdressers

In the first two chapters Paul offered me the chance to be his girl and becoming Jane seemed the most natural thing in the world to me, but I didn't realise how bumpy the road to love, and lust, could be. Paul left my head was spinning: I was upset that my stupidity denied him the chance to fuck me, but I felt so overwhelmed by his attention that I was fu...