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CrossDressing Stories

Displaying stories 121 through 130 of 356

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

A Summer Vacation Story (2)
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.
[More Info]

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: 42723 | Votes: 111 | Score: 6.80
Size: 1226KB | 246,740 words | Posted: Concluded:

122 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: 6432 | Votes: 48 | Score: 6.77
Size: 88KB | 17,049 words | Posted:

123 Truth or Dare Friends: Phoebe's Amulet by Fan Fiction Man

At a farewell party for Joey, the six friends and their many exes and lovers become much more intimate together with help from a special amulet owned by Phoebe. Their lives will never be the same.
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Sex Contents: Stroke Story | Genre: Fan Fiction
Tags: Ma/Fa, Fa/Fa, Mult, Consensual, Magic, Mind Control, Gay, Lesbian, BiSexual, Heterosexual, CrossDressing, Celebrity, Fan Fiction, Paranormal, Sharing, Slut Wife, Wife Watching, Incest, Mother, Son, Brother, Sister, Father, Daughter, Cousins, InLaws, MaleDom, FemaleDom, Humiliation, Rough, Gang Bang, Group Sex, Harem, Orgy, Polygamy/Polyamory, Swinging, Interracial, Black Female, White Male, White Female, Anal Sex, Analingus, Double Penetration, Oral Sex, Pegging, Pregnancy, Squirting, Water Sports
Downloads: 11826 | Votes: 50 | Score: 6.75
Size: 60KB | 11,637 words | Posted: Concluded:

124 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: 4467 | Votes: 28 | Score: 6.74
Size: 235KB | 44,277 words | Posted: Concluded:

125 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: 1757 | Votes: 21 | Score: 6.72
Size: 25KB | 5,032 words | Posted:

126 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: 4734 | Votes: 34 | Score: 6.70
Size: 210KB | 38,459 words | Posted: Concluded:

127 Susan by Aurora

A The Engineer Story (7)
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: 2355 | Votes: 82 | Score: 6.70
Size: 108KB | 21,036 words | Posted:

128 Adventures Into Bisexuality by JohnMurray4173

A coming of age story where a young man in introduced to bisexual sex by a pair of precocious teenage girls and a dominant high school senior.
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Sex Contents: Much Sex | Genre: Coming of Age
Tags: Ma/Fa, mt/ft, mt/Fa, ft/ft, Ma/mt, mt/mt, Coercion, Consensual, Reluctant, BiSexual, Heterosexual, CrossDressing, Fiction, Sharing, BDSM, DomSub, MaleDom, Rough, Anal Sex, Cream Pie, Double Penetration, First, Oral Sex, Pegging
Downloads: 7121 | Votes: 99 | Score: 6.68
Size: 69KB | 13,402 words | Posted: Concluded:

129 Just Do What the Nice Man Says Honey by Michele Nylons

Alex lives with his mother Julie and refuses to get a job or to help Julie pay the rent and household bills. When Julie sees pictures of Alex dressed as a girl she sees that Alex has potential for meaningful employment, even though Alex might not want the job.
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Sex Contents: Much Sex | Genre: Coming of Age
Tags: mt/Fa, Blackmail, Coercion, NonConsensual, Reluctant, CrossDressing, TransGender, Fiction, Incest, Mother, Son, FemaleDom, Rough, Anal Sex, Masturbation, Oral Sex, BBW, Leg Fetish, Prostitution
Downloads: 3126 | Votes: 80 | Score: 6.68
Size: 75KB | 14,205 words | Posted:

130 Deal With the Devil by Xanzibar

A story in the City of Caldwell Universe
A professional working mother tired of seeing her son bullied, goes into the ghetto to confront bully. She ends up accepting a deal that will send her down a debauched, degrading rabbit hole.
[More Info]

Sex Contents: Much Sex | Genre: Erotica
Tags: Ma/Fa, Fa/Fa, Mult, Teenagers, Coercion, Consensual, Reluctant, Slavery, BiSexual, Heterosexual, CrossDressing, TransGender, Fiction, Crime, Workplace, Cuckold, Mother, BDSM, DomSub, MaleDom, Humiliation, Rough, Spanking, Gang Bang, Group Sex, Orgy, Interracial, Black Male, Black Female, White Female, Hispanic Male, Cream Pie, Exhibitionism, Facial, Oral Sex, Foot Fetish, Leg Fetish, ENF, Prostitution, Transformation
Downloads: 5396 | Votes: 52 | Score: 6.68
Size: 89KB | 16,931 words | Posted: in progress Updated:
* Not enough votes to show score yet
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