Men Dressing As Women Stories Stories

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Summertime Cross Dresser Confession

by andtheend on Sep 14, 2017
Transsexuals & Crossdressers

After a long time coming, a lifetime of suffering, the first day of summer is when an aging cross dresser finally gives into the life he's always wanted to live. As if a new beginning, as if being born again, Donald looked to his transformation from man to woman, as his emergence from moth to butterfly. He couldn't wait to fly away to start his life anew. P...

Victoria's Secret

by M Crimm on Sep 13, 2017
Erotic Couplings

OK, I was bored. Really I don't have any excuses. Nor should I have any. I was reading erotic stories online again. Some interested me. A lot didn't. I guess I expected too much. Not that I'm in any position to complain, the stories I've tried to write but all of mine come out as half-assed and looking like a horny teen age boy wrote them. One story, I foun...

Jerome's Special Salad Dressing

by quadcox on Apr 24, 2018
Humor & Satire

This is a satire of some of the stories that appear in the loving wives section. Be warned this story contains a white wife having sex with multiple black men, with some cuckolding elements. If this offends you then, please read on and you may call me a closet homosexual in the comments after. I have tried to make the story as clichéd and outrageous as possi...

Brooke

by fntsymn on Sep 11, 2017
Exhibitionist & Voyeur

This is the first of what will be a series of short stories about Brooke, a Literotica reader who asked me to write some stories about her. She provides some of the facts of the story and the rest is my imagination let loose. I hope you enjoy the stories. And thank you Brooke, love you. Brooke felt the eyes of a man on her and turned her head around, and...

Real Lifestyle Story Ch. 05

by arizonajoe on Sep 17, 2017
Loving Wives

Keep adding me to your favorites list and vote and I will keep telling you real stories about our Lifestyle. This is a fictional story based on fact. Names and locations have been changed to protect my identity and my wife's identity. I have changed enough of the story so as not to incriminate our friends either. Everyone in my stories is over 21. The story...

World of Fashion

by Magna12 on Jan 15, 2019
Mature

I first met Mrs. Susan Noble on a volunteer committee for our neighborhood. She was the wife of a university professor, and I was just a student. Her grace and commitment to community betterment gained my respect, and she was quite a beauty for a woman past her prime. Mrs. Noble was probably in her late fifties. She was tall, shapely but not plump, and stil...

You Can Always Say No Ch. 01

by AngelCherysse on Sep 25, 2017
Fetish

I have always considered myself a liberated woman. Rising through the business ranks to become a Vice-President at a major media consulting agency was just one of many goals I set, then met. I don't see any conflict between that and being a 'girly-girl'. I'm not ashamed to admit; I have used my raven-haired beauty and generous natural charms to advance my ca...

Shopping for Bras and Flashing Tits

by SusanJillParker on Sep 25, 2017
Exhibitionist & Voyeur

Susan loves to expose her naked breasts to men so long as it appears accidental. The mall is Susan's favorite place to flash her body and being that there aren't very many women's dressing rooms left that have curtains instead of doors, Susan was a frequent shopper of Helen's Dress Shop. She wasn't the only one who knew that this dress shop had curtains ins...

Sandra and Stevie Ch. 36

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the thirty-sixth installment in a series entitled "Sandra and Stevie". If you have not read the previous thirty-five episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories, I st...

The Paul & Jenny Stories Pt. 15j

by PAUL C on Sep 12, 2017
Novels and Novellas

The Paul & Jenny Stories Pt. 15j: Another June Wedding Part 10 Copyright 2001 by Paul. All rights reserved. All events and characters are fictitious. * * * * * Spain 1937. Roland Wagstaffe. At the edge of the village we had the party cross some shrub land to the road leading up to the Villa. Miguel, Sister Hortencia and I crept towards the village centr...