Crossdressed Stories

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The Marriage of Martin Hastings Ch. 01

by rik581 on Sep 12, 2017
Transsexuals & Crossdressers

Dark Tales of Forced Feminization Volume One Written by: Rikki, Illustrated by: Annabelle B. "The Martin Hastings Saga" is a work of erotic fantasy/fiction in three distinct pieces and is not based on any beliefs/realities or are any of the characters based on person's alive or dead. This story contains elements of b/d, s/m, forced femininity, and some ex...

Cynthia's Joy

by sinisterout on Sep 13, 2017
Transsexuals & Crossdressers

Many thanks to CKQuail for editorial input and proofreading. ***** In the beginning I knew her by her screen name, Goddess4u2serve. Later I learned her name was Cynthia, but I usually called her 'My Goddess'. She knew I was a cuckold before we'd even met. She'd read the stories I'd posted here on Literotica where I explored my dark fantasies. I can't e...

The Real Kasey Ch. 01

by KaseyLegs on Sep 13, 2017
Transsexuals & Crossdressers

My story begins, for the most part, in the summer of 1996. I was just twenty-one years old at the time and I had managed to hook up with a beautiful older woman. It would not be much of a stretch to say she was a nymphomaniac, but she had a very high sex drive and a desire to explore and experience all sorts of kinks and fetishes. Being young, and this bein...

Five Into Three Does Not Go

by scribbledehobble on Sep 14, 2017
Transsexuals & Crossdressers

Note to reader – This story has both transgendered and lesbian themes. It arose from an extraordinary story I once heard that quite illustrated the difference between smut and erotica. There are two groups of lovers, one group makes love, the other has wild sex. Not for the faint hearted! Note – The story is told from the perspective of five people – Jim...

This to Keep Me Quiet Ch. 01

by MicheleNylons on Oct 5, 2020
Transgender & Crossdressers

Chapter One - It's Not Right Uncle John, For All Sorts of Reasons Author's Note: This is a little two-part tale similar to my early stories. It has all the trappings of a Michelle Nylons story: a little incest, a little blackmail, a lot of sex and a surprising ending. I hope you like it. Crystal Palace sat at the bar watching Melanie Starr singing The Cryi...

Reversals Ch. 13

by RachelClark on Nov 14, 2017
Fetish

Broken Morning came sooner than Eric cared for as he rolled around awkwardly in the makeshift bed on the floor of the bedroom. Above, sprawled across the queen sized bed, slept Julia, comfortable and peaceful without him. It was still early, the sun was slowly brightening against the closed window shades leaving the room cloaked in dim light and shadows as...

Traveling Has Its Rewards

by SummerDreams on Sep 18, 2017
Transsexuals & Crossdressers

It was probably one of my longest trips ever. Not in terms of just distance, but in terms of time. There were two connecting flights, but I'm used to that. But due to strong head winds, my westbound flight was delayed and I missed my scheduled connections. I never liked flying to Oregon, but now sitting around an airport for 4 extra hours in the middle of...

Lucy's Revenge Ch. 06

by Cynthia_D on Sep 18, 2017
Transsexuals & Crossdressers

Final Chapter It was Friday night after a very long week of being humiliated. I had a couple of cocktails to calm down after my latest forced outdoor adventure - being exposed to numerous people while crossdressed. The phone had rung and I made the mistake of answering it thinking it was my wife who was due home that weekend. But the caller wasn't my wife i...

A Strange Romance

by toniukcd on Sep 16, 2017
Transsexuals & Crossdressers

Although I was over qualified after I graduated and accepted a one as an Internet operations officer for one of the high street retailers. I was offered better jobs but I took the one with the retailers because it paid reasonably well and more importantly meant that I would have to relocate down to the East Midlands. Ever since my parents decided when I was...

Would You

by sydian on Sep 16, 2017
Transsexuals & Crossdressers

'Would you...?' 'Look the part to play the part....' 1 5' 4...dreaded, and to be dreaded....bookish, be-spectacled—damn near owlish....so much so that you might miss the way her tits spoke to you no matter how much she attempted to 'silence' them ....that you might miss the way her skirt gathered at the flatness of her tum, then fell away from her no-wais...