Free Stories Of Men Caught Crossdressing Stories

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"A Shemale Submission": A Lust Story

by silkstockingslover on Dec 23, 2019
Illustrated

"A Shemale Submission": A Lust Story Summary: Author Jasmine falls for a hot new teacher with a big cock. Note: Thanks to hfernandez1983 for the many pictures used in this story. He spent weeks getting these perfect for the many different scenes I requested. If you like the pictures in this story, please feel free to read the multi-chaptered series Cheerle...

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...

Michele and Buster: A Tranny Tale

by MicheleNylons on Sep 14, 2017
Illustrated

This is the continuation of my True Stories series, where I tell my readers about my real life adventures as a part time transvestite. In this instalment I will tell you about Buster, an admirer with whom I have I met up with a number of occasions. I warn you now that the story contains graphic sex, use of alcohol, mild bondage, use of recreational drugs and...

Daniel and Jamie's Romantic Night

by lockedinsteel on Nov 8, 2017
Group Sex

Jamie stepped out of the cold up to the hostess desk at the chic, trendy, new restaurant. It was the first time that she had been out with her husband, without the kids, in she couldn't remember how long. It was a weird feeling, she thought to herself. Not to have to worry about anyone making it inside or helping kids off with their jackets. It was liberat...

Isabella's Reversion Pt. 03

by silverbackteddy on Sep 16, 2017
Fetish

Note from the Author: This is a story about ABDL. The first word being Adult. All sexual encounters center around Adults, above the age of 18. This story also contains BDSM, plushophilia, watersports, and various other fetishes. For those that are grammar freaks, please don't comment on my improper grammar use. I could care less. At least it doesn't have...

Restitution Pt. 02

by MoniqueSinclair on Sep 15, 2017
BDSM

Carl wiped at his face and pulled himself away from Kelly's bosom. His head ducked and he hurriedly pulled his pants up from his ankles. His cock was still wet as he stuffed it into his briefs. He made no attempt to button his trousers but rather held them together with his hand and turned away from his wife. He paused as if he was about to say something, Ke...

Bed and Breakfast Hotwife

by donaldelliott11 on Mar 9, 2020
Loving Wives

[Note: The hotwife in this story is, well, a wife, right? That means she has a husband. When she gets hot, he becomes a cuckold. You following this, Annony? Get over it, or read a different story. Oh, yeah, one more thing -- BTB is a fetish and has no place in Loving Wives.] *** Tracy and Don Elliott, empty-nesters in their late 40s, supplement their incom...

A Gift in Disguise Ch. 14

by Talespin on Apr 2, 2018
Novels and Novellas

"Murph really likes you, Tom," Bethany said softly while we walked hand-in-hand to her car. "He seems like a very nice guy," I answered. "And he obviously thinks the world of you, too." "He's a good judge of character," Bethany said as we approached her car. "Humble much?" I chided her laughingly. "I meant yours!" she responded with a good-natured punch...

Chasing Mistress Steph

by PaxNurgle on Apr 11, 2018
BDSM

Disclaimer: Although this isn't a BDSM story in the strictest sense, it does include graphic depictions of such content, particularly female domination and fetish. If such content is disturbing to you, then you might not want to proceed. ***** -1- Alexandr Krivstov stared out from his balcony as the setting sun turned the sky a brilliant shade of orange....

My Metaphor

by hyperpress on Dec 24, 2018
Fetish

The audience drops into a continuing story written in first person POV (mostly). The following based on a true story. Given enough time, any question that occurs to the reader shall be answered, eventually. * I woke the next day, showered, put on a comfortable chemise, a microfiber and nylon blend thong and open toed sandals, made some coffee and sat down...