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CrossDressing Stories

Displaying stories 101 through 110 of 355

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101 The Hitman Wore Heels by Michele Nylons

The Hitman is a professional assassin and master of disguise. To carry out his next hit he has to dress as a woman to get close to his mark who has a proclivity for transvestites. Feedback and comments are always welcome.
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Sex Contents: Much Sex | Genre: Erotica
Tags: Ma/Ma, Coercion, CrossDressing, Fiction, Oral Sex, Anal Sex, Masturbation, Exhibitionism, Voyeurism, Leg Fetish, Violent, Transformation
Downloads: 1971 | Votes: 48 | Score: 6.95
Size: 47KB | 8,758 words | Posted:

102 Where? by Everydayguy

Where does a guy go to find another guy interested in some "MAN" sex? A short discussion of where and how. Informative but no real sex. Just some instruction. (Not for homophobes)
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Sex Contents: No Sex | Genre: True Story
Tags: Ma/Ma, Gay, BiSexual, TransGender, CrossDressing, School
Downloads: 1385 | Votes: 36 | Score: 6.94
Size: 7KB | 1,466 words | Posted:

103 The Collector by Michele Nylons

The Collector collects girls and takes them to his estate where they become Novices, to be trained in the arts of sexually satisfying their Masters. When they graduate they become Acolytes, living a life of sexual servitude to the Order of the Circle who use them for their sexual gratification. We follow the indoctrination of Mary, a girl from a poor background and Charlotte, who comes from a rich family and who is the first transsexual girl to be indoctrinated in the Order.
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Sex Contents: Much Sex | Genre: Coming of Age
Tags: Fa/ft, Coercion, Mind Control, Heterosexual, CrossDressing, TransGender, Historical, School, Workplace, Father, Daughter, MaleDom, Gang Bang, Group Sex, Harem, Orgy, White Couple, Anal Sex, Cream Pie, Exhibitionism, First, Masturbation, Oral Sex, Sex Toys, Leg Fetish, Public Sex, Prostitution, Transformation
Downloads: 6495 | Votes: 55 | Score: 6.93
Size: 197KB | 35,957 words | Posted: Concluded:

104 The Girl in the Blue Denim Skirt by Michele Nylons

Dennis becomes infatuated with the girl in the blue denim skirt who sits on the low brick wall running along the path inside Aston Park. He knows that his infatuation with her is troublesome and that he should just ignore her but he just can't resist her allure.
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Sex Contents: Much Sex | Genre: Fiction
Tags: Ma/Fa, Consensual, CrossDressing, Shemale, TransGender, True Story, Workplace, Cheating, Wife Watching, Anal Sex, Cream Pie, Petting, Voyeurism, BBW, Foot Fetish, Leg Fetish, Public Sex, Smoking
Downloads: 1546 | Votes: 54 | Score: 6.93
Size: 47KB | 8,923 words | Posted:

105 My First Dressed Meeting by tiffany58

A T-girl has her first ever meeting with a man and it opens a whole new world for her. From a public carpark kiss to a full bedroom experience in one afternoon. A day of firsts
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Sex Contents: Much Sex | Genre: Erotica
Tags: Ma/Ma, Consensual, CrossDressing, True Story, DomSub, Spanking, Anal Sex, First, Facial, Oral Sex, Public Sex
Downloads: 1935 | Votes: 61 | Score: 6.93
Size: 17KB | 3,506 words | Posted:

106 I Became My Best Friend's Slut for Halloween by Impala05

Elijah dressed up like a slut for Halloween, and his best friend Bennett can’t help but notice him in a whole new way.
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Sex Contents: Much Sex | Genre: Erotica
Tags: Ma/Ma, Teenagers, Consensual, Gay, BiSexual, Heterosexual, CrossDressing, Fiction, Anal Sex, Cream Pie
Downloads: 937 | Votes: 20 | Score: 6.92
Size: 9KB | 1,758 words | Posted: in progress

107 Carl or Carla by Mystic47

A sister helps her brother dress up like a woman for a costume party.
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Sex Contents: Some Sex | Genre: Erotica
Tags: mt/ft, Consensual, Heterosexual, CrossDressing, Fiction, Brother, Sister
Downloads: 6390 | Votes: 210 | Score: 6.91
Size: 26KB | 5,318 words | Posted:

108 Unconventional by Severusmax

This is a story that just came to mind of late from an image in my head of a cosplay gang-bang, and it just mushroomed from there. Our hero is about to really go down a rabbit hole at a convention this week, but oh what fun it will be!
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Sex Contents: Stroke Story | Genre: Erotica
Tags: Ma/Fa, Mult, Consensual, Drunk/Drugged, Magic, Gay, BiSexual, Heterosexual, CrossDressing, Crime, Humor, Sharing, Slut Wife, Wife Watching, Incest, Brother, Sister, Father, Daughter, InLaws, BDSM, Rough, Spanking, Gang Bang, Group Sex, Harem, Orgy, Polygamy/Polyamory, Swinging, Interracial, Black Female, White Male, White Female, Oriental Female, Anal Sex, Analingus, Cream Pie, Double Penetration, First, Food, Oral Sex, Pregnancy, Squirting, Tit-Fucking, Water Sports, Body Modification, Doctor/Nurse, Geeks, Violent
Downloads: 14249 | Votes: 44 | Score: 6.91
Size: 276KB | 53,177 words | Posted: Concluded:

109 The Lucky Gardener at the Girls School by Shani 34

Arthur is the gardener at a girls school, and spies on the girls until he is caught by Sylvia, the delicious PE teacher. This story is about how Sylvia turns Arthur into Angela, and makes Angela wear girl clothing, sleep in the girls'dormitory, and pleasure all those needy girls. Sylvia uses a strap and a cane on her girls, and Angela experiences those also.
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Sex Contents: Much Sex | Genre: Erotica
Tags: Consensual, Heterosexual, CrossDressing, Fiction, Spanking, Humiliation, First, Oral Sex, Masturbation, School
Downloads: 6947 | Votes: 107 | Score: 6.89
Size: 60KB | 11,464 words | Posted:

110 Big John by Urtles53

The story of my first gay sex as a mature man with a mature man.
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Sex Contents: Some Sex | Genre: Erotica
Tags: Ma/Ma, Consensual, Romantic, Gay, CrossDressing, Fiction, True Story, Oral Sex
Downloads: 480 | Votes: * | Score: *
Size: 9KB | 1,874 words | Posted:
* Not enough votes to show score yet
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