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CrossDressing Stories

Displaying stories 141 through 150 of 351

141 Neil by Its a skirt, not a kilt

When I woke up and eventually dragged myself out of bed on this New Year 's Day, I hadn't planned on writing a short story. But that's what happened, and here we are. A young man in his early twenty's, desperate for companionship, unexpectedly finds some company when he goes swimming. The meeting leads to the young man finding out more about himself and his desires.
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Sex Contents: Some Sex | Genre: Erotica
Tags: Ma/Ma, Consensual, Gay, CrossDressing, Anal Sex, Oral Sex
Downloads: 1005 | Votes: 24 | Score: 6.55
Size: 24KB | 4,702 words | Posted:

142 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: 4838 | Votes: 40 | Score: 6.54
Size: 117KB | 23,267 words | Posted: Concluded:

143 Alex is 17 by Serena Jones

A Davidson Fisheries and the McElroy Family Story (6)
Continues the life of Alex McElroy started in 'Alex and Peter'. Alex has learned that he is a submissive masochist by preference and bi-sexual to boot. Now that Peter has gone to college, however, he has to deal with it on his own. Picking his own girlfriends - heck even picking his own boyfriends! - Alex has to learn how to live like a slave when his Master is away!
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Sex Contents: Much Sex | Genre: Drama
Tags: mt/ft, mt/mt, Mult, Teenagers, Consensual, Reluctant, Coercion, Gay, BiSexual, Heterosexual, CrossDressing, Incest, Cousins, DomSub, Rough, Group Sex, Interracial, White Male, White Female, Oriental Male, First, Oral Sex, Anal Sex, Sex Toys, Voyeurism
Downloads: 4712 | Votes: 42 | Score: 6.52
Size: 116KB | 22,738 words | Posted:

144 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: 2867 | Votes: 99 | Score: 6.52
Size: 22KB | 4,650 words | Posted:

145 Meet My Family by OmegaPet-58

Connor anticipates having Kara, his amazing girlfriend, sleep over. Their nudist and highly affectionate parents are working to have everything ready for their "first time" together. After they all have dinner together, the young couple will have the house to themselves, jealous younger brother leaves also. Kara reminds nervous Connor to eat instead of staring at her, "You'll need your strength."
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Sex Contents: Much Sex | Genre: Coming of Age
Tags: Ma/Fa, mt/ft, Ma/ft, mt/Fa, Fa/ft, Consensual, Romantic, Lesbian, BiSexual, Heterosexual, CrossDressing, Fiction, Sharing, Incest, Mother, Son, Daughter, Swinging, Anal Sex, First, Masturbation, Oral Sex, Sex Toys, Squirting, Hairy, Size, Nudism, Slow, Illustrated
Downloads: 8772 | Votes: 64 | Score: 6.51
Size: 130KB | 25,132 words | Posted: Concluded:

146 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: 3996 | Votes: 24 | Score: 6.50
Size: 28KB | 5,515 words | Posted:

147 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: 1125 | Votes: 44 | Score: 6.50
Size: 15KB | 2,894 words | Posted:

148 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: 712 | Votes: 24 | Score: 6.50
Size: 24KB | 4,847 words | Posted:

149 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: 6859 | Votes: 151 | Score: 6.49
Size: 59KB | 11,018 words | Posted: Concluded:

150 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: 1226 | Votes: 35 | Score: 6.48
Size: 45KB | 8,313 words | Posted:
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