Sex Stories 69 Crossdressing Stories

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Exploring Sexuality: A Pegging

by silkstockingslover on Sep 25, 2017
Anal

Summary: Husband is pegged by sister-in-law with wife's permission Note 1: Thanks to Robert, goamz86 and Wayne for editing. Exploring Sexuality: A Pegging I was almost in the city when my cell rang. I glanced at it and saw it was my sister-in-law Sabrina. I sighed. I loved Sabrina, but since her divorce she had been as exciting as a Nicholas Sparks mov...

Twenty-One More Questions

by silkstockingslover on Jan 1, 2019
Reviews & Essays

Summary: Jasmine responds to the most frequent questions asked by readers. Thanks to: Tex Beethoven, Wayne, and Robert for editing this essay. This isn't really a sequel, although it's a second part, as it addresses questions I didn't answer in 2017's Twenty Questions. 21 More Questions After 2017's 20 Questions, I received many more questions. I have n...

Kinky Tales: I'm Pegged By My Wife

by silkstockingslover on Mar 27, 2019
Fetish

Summary: Note 1: This is a Halloween 2015 Contest Story. Note 2: This is one of two different versions of this story; you can read the wife's much longer version called Kinky Tales: I Pegged my Husband Note 3: This is dedicated to: The real Chris and Dani who this fantasy is written about. It is also dedicated to all married couples willing to listen...

Getting to Know Her Ch. 03

by britasveritas1 on Sep 16, 2017
Fetish

Ch. 03: Sweet Sex Forward: This is the third (of four) in this series. Certainly reading the first two parts of this series would help in understanding this part, although this one can stand on its own for a number of reasons. Some might find it useful to also read my first and second stories "Getting into her pants" and "Nobody knew" which provide some ad...

Mistress Viagra Pt. 01

by Njstraponlover on Sep 13, 2017
Fetish

This story is 100% pure fantasy. None of it ever happened. If you are offended by stories of a mature nature containing references to bondage and humiliation, please do not read. This is fiction!! ***** I had been chatting with a new online mistress for a number of months and during that time she had me buying all kinds of sexy woman's cloths, new sex toy...

Sissy/Cock Sucker Dictionary

by silkstockingslover on Jun 12, 2019
Reviews & Essays

Summary: A list of terms to aid in understanding the activities and nature of sissies and cock suckers. Note 1: The author's source material isn't Webster's Dictionary or anything similar, but is drawn from many years of interest in matters sexual and countless conversations, both spoken and online, with other perverts. Note 2: Thanks to Tex Beethoven and...

The Business Trip

by OOAA on May 11, 2020
Fetish

My wife and I had been married for about 3 years when I first developed an interest in enforced male chastity. I had always had a very kinky and active fantasy life to fuel my almost daily masturbation habit. I was a 22-year-old virgin when I met Irene and I was looking to resolve that problem. Irene seemed like an exciting 20-year-old girl and I thought tha...

Tawny Ch. 04

by JayLikestoRead on Sep 25, 2017
Erotic Couplings

"Patient's name: Hall, Tawny. Age: 19. Week: 20." Tawny's file indicated only the relevant medical information. It didn't mention her long black hair or the fact that her breasts had gone from tear-shaped C cups to a more convex D cup. She had gained fifteen pounds since the original confirmation of pregnancy. I told her, "In a few weeks we should be able t...

Bobby

by jakladd on Sep 13, 2017
Novels and Novellas

Boston with its many old neighborhoods is as varied as its people. In the older seedier parts of town many people live and carry on in a world much different from the clinically clean and proper suburbs. On some streets there are rows and rows of the monotonous dark brick two, three, five or six story apartment buildings many exactly like the one next to it...

Body and Mind

by ThighhighMellie on Sep 16, 2017
Romance

Disclaimer: This story touches on several sensitive subjects, such as transsexuality and sexual assault. Reader discretion is advised. All characters are eighteen or older. "To be yourself in a world that is constantly trying to make you something else is the greatest accomplishment." -Ralph Waldo Emerson Prologue Nearly everyone has something they disli...