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CrossDressing Stories

Displaying stories 141 through 150 of 350

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141 High Fashion Queen & High Fashion Queen Redux by Melanieatplay

In a highly sexually charged tale, Jesse, a diminutive Asian teenager who is discovering his sexuality, gets help from his BFF from middle school, Sara, to dress as a woman. As Jesse's true calling emerges, a spontaneous blowjob sets the stage for him to become the woman of his dreams. As more characters weave their way into the story, they both have a night they will never forget.
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Sex Contents: Some Sex | Genre: Erotica
Tags: Ma/Fa, Romantic, Lesbian, Heterosexual, CrossDressing, Fiction, School, Oral Sex
Downloads: 4827 | Votes: 40 | Score: 6.54
Size: 117KB | 23,267 words | Posted: Concluded:

142 Won't Get Fooled Again by Mushroom

A guy and gal meet each other at a club, and sparks fly between the two of them. But each of them has a secret they are keeping from the other.
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Sex Contents: Much Sex | Genre: Erotica
Tags: Ma/Fa, Heterosexual, CrossDressing, Anal Sex, Cream Pie, Oral Sex
Downloads: 2858 | Votes: 99 | Score: 6.52
Size: 22KB | 4,650 words | Posted:

143 Craig by Its a skirt, not a kilt

Desperate to own a wedding dress, Craig decides to buy one second hand from the local classifieds. Things don't quite go as he envisioned they would.
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Sex Contents: Some Sex | Genre: Fiction
Tags: Ma/Ma, Reluctant, CrossDressing, Fiction, Anal Sex
Downloads: 1110 | Votes: 44 | Score: 6.50
Size: 15KB | 2,894 words | Posted:

144 Entrapment by Couture

A mixup at the costume shop results in a sexy Halloween
Premier members only
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Sex Contents: Much Sex | Genre: Erotica
Tags: Ma/Fa, Reluctant, CrossDressing, FemaleDom, Light Bond, Halloween
Downloads: 3982 | Votes: 24 | Score: 6.50
Size: 28KB | 5,515 words | Posted:

145 Hotel Rendezvous by tiffany58

I was inspired by the opening premise of Oliver Twist’s excellent “My double life as a whore,” where a surprise meeting in a hotel bar leads to many other things, to recount my own true story of my recent hotel bar adventure.
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Sex Contents: Much Sex | Genre: Erotica
Tags: Ma/Ma, Consensual, Romantic, Gay, CrossDressing, True Story, Anal Sex, Analingus, Enema, Exhibitionism, Oral Sex, Public Sex
Downloads: 697 | Votes: 24 | Score: 6.50
Size: 24KB | 4,847 words | Posted:

146 James Bondage Quickies by James Bondage

An anthology of Femdom / Futa on male short stories. Inspired by some of my favorite works of hentai art. Note: The setting, kinks and themes differ from story to story. Not all tags apply to each tale.
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Sex Contents: Stroke Story | Genre: BDSM
Tags: Ma/Fa, Mult, Coercion, Consensual, NonConsensual, Reluctant, Slavery, Heterosexual, CrossDressing, Shemale, Fiction, Fan Fiction, Futanari, High Fantasy, Vignettes, Science Fiction, Paranormal, Magic, Demons, Cheating, Sharing, Incest, Mother, Son, BDSM, DomSub, FemaleDom, Humiliation, Rough, Spanking, Gang Bang, Group Sex, Interracial, Anal Sex, Analingus, Double Penetration, First, Masturbation, Oral Sex, Pegging, Sex Toys, Spitting, BBW, Big Breasts, Body Modification, Public Sex, Size, Prostitution, Revenge, Transformation
Downloads: 14321 | Votes: 58 | Score: 6.49
Size: 477KB | 88,080 words | Posted: in progress Updated:

147 Al by ChrisM

Cross-dressing comes in all varieties.
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Sex Contents: Some Sex | Genre: Erotica
Tags: Fa/Fa, Lesbian, CrossDressing, Fiction, Oral Sex
Downloads: 764 | Votes: 26 | Score: 6.49
Size: 16KB | 3,190 words | Posted:

148 The Highwayman's Daughter by harry lime

Young Meg is certain she has found the ideal way for both she and her father to pay their way in the world. Unfortunately, it involves robbery on the King's highway and that is a "Hanging" offense.
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Sex Contents: Much Sex | Genre: Erotica
Tags: Ma/Fa, Consensual, BiSexual, CrossDressing, Fiction, Historical, Spanking, Group Sex, Oral Sex, Anal Sex, Cream Pie, Exhibitionism
Downloads: 6850 | Votes: 151 | Score: 6.49
Size: 59KB | 11,018 words | Posted: Concluded:

149 Diary of a Prostitute by Michele Nylons

Bored with their sex life and seeking to supplement their income a husband and wife decide to enter the world of prostitution. This is a vignette in the day of a life of a high-class prostitute and explains how a married couple can live happily together while they each have sex with strangers for money.
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Sex Contents: Much Sex | Genre: Erotica
Tags: Ma/Fa, Ma/Ma, Consensual, BiSexual, CrossDressing, Shemale, TransGender, Fiction, Vignettes, Sharing, Black Male, Anal Sex, Analingus, Cream Pie, Facial, Masturbation, Oral Sex, Petting, Foot Fetish, Leg Fetish, Prostitution
Downloads: 1183 | Votes: 35 | Score: 6.48
Size: 45KB | 8,313 words | Posted:

150 Bottoms Up by Mark Gander

A Yankee from Jersey moves to Georgia after leaving his frigid wife and meets a submissive Southern family with the intriguing name of Bottom and a long family tradition of serving outsiders. The women are sweet Georgia Peaches and the men are, well...pretty boys who bring out the latent bisexuality in this emerging Dom.
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Sex Contents: Much Sex | Genre: BDSM
Tags: Ma/Fa, mt/ft, Ma/ft, mt/Fa, Fa/Fa, ft/ft, Fa/ft, Ma/Ma, Ma/mt, mt/mt, Mult, Teenagers, Blackmail, Consensual, NonConsensual, Gay, Lesbian, BiSexual, Heterosexual, CrossDressing, TransGender, Workplace, Incest, BDSM, Interracial, Anal Sex, Analingus, Oral Sex
Downloads: 97753 | Votes: 352 | Score: 6.47
Size: 642KB | 124,281 words | Posted: Concluded:
* Not enough votes to show score yet
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