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CrossDressing Stories

Displaying stories 51 through 60 of 378

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51 The Cheerleader by Michele Nylons

A crossdressed college cheerleader realizes that her femininity, good looks and sensuality are commodities that she can trade to improve her grades. With the help of her sister, she transforms from pretty boy to pretty girl and soon discovers that boys like her more than they should and she is more than willing to put out to get ahead.
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Sex Contents: Much Sex | Genre: Erotica
Tags: Teenagers, Coercion, Consensual, Reluctant, CrossDressing, Shemale, Fiction, High Fantasy, School, Anal Sex, Analingus, Cream Pie, First, Oral Sex, Petting, Voyeurism, Leg Fetish, Teacher/Student
Downloads: 1957 Votes: 19 | Score: 7.48
Size: 79KB | 14,689 words | Posted:

52 Ben Stokes' Swinging Household Part 5: Barry and Gloria by JohnMurray4173

A story in the Tranny Babysitter/Ben Stokes' Swinging Household Universe
The Stokes's household members, Barry and Gloria, get married. Their story before and after their wedding.
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Sex Contents: Much Sex | Genre: Erotica
Tags: Ma/Fa, Fa/Fa, Ma/Ma, Reluctant, Slavery, Gay, Lesbian, BiSexual, Heterosexual, CrossDressing, TransGender, Fiction, Cuckold, Sharing, Slut Wife, Wife Watching, BDSM, DomSub, MaleDom, FemaleDom, Humiliation, Rough, Sadistic, Spanking, Torture, Gang Bang, Group Sex, Orgy, Swinging, Black Male, White Male, White Female, Anal Sex, Analingus, Cream Pie, Double Penetration, Enema, Exhibitionism, Facial, Fisting, Oral Sex, Pegging, Sex Toys, Spitting, Squirting, Voyeurism, Water Sports, Big Breasts, Needles, Public Sex
Downloads: 2353 Votes: * | Score: *
Size: 235KB | 42,477 words | Posted:

53 Ghost at the Rave Party by VerbalAbuse

A man chases a naked woman at an extravagant party.
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Sex Contents: Minimal Sex | Genre: Erotica
Tags: Ma/Fa, CrossDressing, Shemale, TransGender
Downloads: 376 Votes: * | Score: *
Size: 19KB | 3,393 words | Posted:

54 The Teachers Pet Her by JDlit71

Dirty Dianna learns more in her quest for a finer education. Principals and Professors help her navigate through the lessons of life.
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Sex Contents: Much Sex | Genre: Erotica
Tags: Ma/Fa, Fa/Fa, Teenagers, Consensual, NonConsensual, Lesbian, BiSexual, Heterosexual, CrossDressing, School, Sister, BDSM, MaleDom, FemaleDom, Humiliation, Rough, Gang Bang, Interracial, Black Male, White Female, Anal Sex, Double Penetration, Oral Sex, Sex Toys, Teacher/Student
Downloads: 694 Votes: * | Score: *
Size: 28KB | 5,634 words | Posted: in progress

55 Woman In The Mirror by plaplen

A story told of the transition from a young boy to a grown woman.This is a fictional story about Gender Dysphoria and M2F transitioning. This story does become "fairly" technical in the aspects of transitioning, such as GRS and HRT.
Premier members only
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Sex Contents: Some Sex | Genre: Drama
Tags: Ma/Fa, Mult, Consensual, Romantic, BiSexual, Heterosexual, TransGender, CrossDressing, Hermaphrodite, Cheating, Slut Wife, Wimp Husband, Cuckold, FemaleDom, Humiliation, Swinging, Group Sex, Orgy, Masturbation, Body Modification, Slow
Downloads: 6981 Votes: 100 | Score: 7.45
Size: 157KB | 30,179 words | Posted:

56 Stockings by Bondi Beach

Charlie and her brother like to dress up. Things change between the two of them and with their parents during a summer vacation at the lake, when their favorite game becomes more than a game and they discover love reveals itself in many forms. This story is about love and boners, inspired by the art of J. B. Hopkings. NOTE: Check the codes. If you're not sure what "pegging" is, find out before you start. Also, be advised there is some mm and mM, oral, in this story.
[More Info]

Sex Contents: Much Sex | Genre: Erotica
Tags: Ma/Fa, mt/ft, Ma/ft, mt/Fa, ft/ft, Fa/ft, mt/mt, Mult, Consensual, CrossDressing, Fiction, Incest, Pegging
Downloads: 11911 Votes: 136 | Score: 7.45
Size: 119KB | 24,171 words | Posted:

57 Kathleen by Ghetta Grippe

Kathleen is a Big Beautiful Woman who's appetite for uninhibited lust is as large as her magnificent body.
Premier members only
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Sex Contents: Some Sex | Genre: Incest
Tags: Ma/Fa, mt/ft, Ma/ft, mt/Fa, Fa/Fa, Ma/Ma, Mult, Consensual, Drunk/Drugged, BiSexual, TransGender, CrossDressing, Incest, Brother, Sister, Swinging, Group Sex, Orgy, Interracial, Oral Sex, Anal Sex, Cream Pie, BBW, Slow
Downloads: 14461 Votes: 26 | Score: 7.45
Size: 160KB | 30,192 words | Posted: Concluded:

58 Gift Horse by Maxicue

A demented thriller about a guy a gal and a bar. Don't look a gift in the mouth, it might just bite.
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Sex Contents: Some Sex | Genre: Erotica
Tags: Ma/Fa, Fa/Fa, Consensual, Romantic, Drunk/Drugged, Lesbian, Heterosexual, CrossDressing, Humor, Interracial, Voyeurism, Slow, Caution, Violent
Downloads: 3677 Votes: 28 | Score: 7.43
Size: 151KB | 28,435 words | Posted:

59 Attacked by Silk Gloves by RH Music

While searching for "real magic", Paul locates a crotchety old woman named Rosemary, who can perform a special "glove trick". This trick involves a long glove that comes to life and leaps over the hand and arm of an unsuspecting spectator. Soon Paul discovers that living gloves are just the beginning...
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Sex Contents: Much Sex | Genre: Erotica
Tags: Ma/Fa, NonConsensual, Reluctant, Coercion, Magic, TransGender, CrossDressing, BDSM, DomSub, FemaleDom, Masturbation, Transformation
Downloads: 7374 Votes: 123 | Score: 7.43
Size: 87KB | 16,025 words | Posted:

60 High Fashion Queen Redux by Melanieatplay

The evening of "High Fashion Queen" is retold from Jesse's perspective.
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Sex Contents: Much Sex | Genre: Erotica
Tags: Ma/Ma, Consensual, CrossDressing, TransGender, Fiction, White Male, Oriental Male, Anal Sex, Cream Pie
Downloads: 1149 Votes: 25 | Score: 7.43
Size: 64KB | 12,901 words | Posted:
* Not enough votes to show score yet
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