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CrossDressing Stories

Displaying stories 121 through 130 of 376

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121 How to Expand Your Wife's Horizons by JohnMurray4173

A mildly exaggerated true story on how I moved my wife from repressed religious girl to a confident BDSM switch.
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Sex Contents: Some Sex | Genre: True Story
Tags: Ma/Fa, Fa/Fa, Ma/Ma, Consensual, Reluctant, Gay, Lesbian, BiSexual, Heterosexual, CrossDressing, TransGender, True Story, Cheating, Sharing, Slut Wife, Wife Watching, BDSM, DomSub, MaleDom, FemaleDom, Spanking, Group Sex, Swinging, Anal Sex, Double Penetration, Exhibitionism, Facial, Masturbation, Oral Sex, Pegging, Sex Toys
Downloads: 5716 Votes: 25 | Score: 6.82
Size: 197KB | 37,721 words | Posted:

122 Coffee Shop Girl by Michele Nylons

A young male college student notices that a coffee shop is only employing pretty young women. He disguises himself as a girl to get a job in the establishment but soon discovers that the girl he has become must surrender her virtue to remain employed.
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Sex Contents: Much Sex | Genre: Erotica
Tags: Ma/Fa, Teenagers, Coercion, NonConsensual, Reluctant, CrossDressing, TransGender, Fiction, School, Workplace, Anal Sex, Analingus, First, Facial, Masturbation, Oral Sex, Leg Fetish, Public Sex, Teacher/Student
Downloads: 2456 Votes: 37 | Score: 6.77
Size: 129KB | 24,288 words | Posted:

123 TNWS04 Sweet Sixteen by Murray Wilson

A story in the This Naked World Universe
Continuing on from the last story... Uncle Brady Goes to Night School... we have Jay Porter now turning sixteen and having some fun at home with his family then at school with his teacher then in the evening with his girlfriend.
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Sex Contents: Much Sex | Genre: Erotica
Tags: Mult, Teenagers, Consensual, Romantic, Gay, Lesbian, Heterosexual, CrossDressing, Shemale, TransGender, Fiction, School, Incest, Mother, Son, Brother, Sister, Father, Daughter, Uncle, Niece, Aunt, Nephew, Group Sex, Cream Pie, Exhibitionism, Masturbation, Oral Sex, Squirting, Voyeurism, Big Breasts, Hairy, Public Sex, Teacher/Student, Nudism
Downloads: 7021 Votes: 49 | Score: 6.76
Size: 88KB | 17,049 words | Posted:

124 Susan by Aurora

A The Engineer Story
This is the seventh story of the engineer series
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Sex Contents: Some Sex | Genre: Erotica
Tags: Fa/Fa, Consensual, Lesbian, BiSexual, CrossDressing, TransGender, Fiction, BDSM, Spanking, PonyGirl
Downloads: 2764 Votes: 84 | Score: 6.75
Size: 108KB | 21,036 words | Posted:

125 So You Want to Be a Nurse by Michele Nylons

In 1957 Michael Nyland is one of the few male nurses working at Chelmsford Memorial Hospital. Matron Amanda Holliday and Doctor Lovejoy have uncovered his secret fetish for lingerie. One day he wakes up in one of the private wards tied to the bed dressed in silky full-slip, satin cami-knickers, sheer hose, high-heels; and makeup professionally applied and hair coiffured. Nurse Nyland has no choice but to satisfy the Doctor but is totally unprepared for life as a transvestite prostitute.
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Sex Contents: Stroke Story | Genre: Erotica
Tags: Mult, Blackmail, Coercion, Drunk/Drugged, NonConsensual, Rape, Reluctant, CrossDressing, Shemale, TransGender, Fiction, Workplace, Revenge, Gang Bang, Group Sex, Orgy, White Male, White Female, Anal Sex, Masturbation, Oral Sex, Voyeurism, Foot Fetish, Leg Fetish, Public Sex, Teacher/Student, Prostitution, Transformation
Downloads: 5056 Votes: 36 | Score: 6.75
Size: 210KB | 38,459 words | Posted: Concluded:

126 The Mistress of Holt House- Part One by Midsummerman

Femdom in the Victorian era. A male in a male dominated society finds thar Women are really in charge.
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Sex Contents: Much Sex | Genre: BDSM
Tags: Ma/Fa, Mult, Consensual, Reluctant, Coercion, Slavery, Heterosexual, CrossDressing, Fiction, Historical, BDSM, DomSub, Spanking, Rough, Humiliation, Sadistic, Oral Sex, Anal Sex, Masturbation, Sex Toys, Exhibitionism, Transformation
Downloads: 4815 Votes: 29 | Score: 6.74
Size: 235KB | 44,277 words | Posted: Concluded:

127 Naked on Summer Vacation: Slut Summer School by Eddie Davidson

A Summer Vacation Story
Part of the Davidson Family Stories universe
It was 1984 in Sebastian Florida and my Cousin Blair had thrown one party too many. My Aunt found normal restriction and punishments just were not very effective. She put Blair and her friends through a re-education in Slut Summer School **Involves BDSM/Humiliation, there is a prequel Naked on Summer Vacation: Sissy Summer School that sets the scene but it is not required reading.
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Sex Contents: Much Sex | Genre: BDSM
Tags: Teenagers, Reluctant, Lesbian, Heterosexual, CrossDressing, Shemale, Slut Wife, Incest, Mother, Cousins, Aunt, BDSM, FemaleDom, Humiliation, Light Bond, Spanking, Group Sex, Anal Sex, Cream Pie, Enema, Exhibitionism, Fisting, Flatulence, Food, Masturbation, Oral Sex, Pegging, Sex Toys, Spitting, Tit-Fucking, Water Sports, Babysitter, Big Breasts, Public Sex, Cat-Fighting, Prostitution
Downloads: 46207 Votes: 114 | Score: 6.74
Size: 1226KB | 246,740 words | Posted: Concluded:

128 So Sue Me by Tarl Cabot

This is a direct continuation of Dave's Gay Experience. Dave returns to make amends with his Sister. Josh is jealous of their connection.
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Sex Contents: Some Sex | Genre: Incest
Tags: Ma/Fa, Ma/Ma, Consensual, Reluctant, Gay, BiSexual, Heterosexual, CrossDressing, Fiction, Incest, Mother, Son, Brother, Sister, Uncle, Nephew, Group Sex, White Male, White Female, Anal Sex, Cream Pie, Oral Sex, Pegging, Sex Toys
Downloads: 1761 Votes: 41 | Score: 6.74
Size: 64KB | 12,931 words | Posted: Concluded:

129 A Hot Evening With Miriam by elevated_subways

A virginal young guy is rebuffed during his first experiences with a girlfriend. Then he gets involved with an unusual older neighbor. This is set in 1981.
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Sex Contents: Some Sex | Genre: Erotica
Tags: Ma/Fa, Consensual, Romantic, CrossDressing, Shemale, TransGender, Fiction, Masturbation, Oral Sex, Petting
Downloads: 1392 Votes: 44 | Score: 6.73
Size: 41KB | 8,187 words | Posted:

130 Email Across the Pond by NiteWriter

A 14 year old girl writes to a friend who has emigrated to Canada telling her of some cross-dressing sexy fun she has had resulting in an unexpected lesbian romp.
Premier members only
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Sex Contents: Much Sex | Genre: Erotica
Tags: ft/ft, Teenagers, Consensual, Romantic, Lesbian, CrossDressing, True Story, First, Oral Sex, Masturbation, Sex Toys
Downloads: 1780 Votes: 21 | Score: 6.72
Size: 25KB | 5,032 words | Posted:
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