CrossDressing Stories

Displaying stories 101 through 110 of 351

101 Chosen by Chance by Vasantrutu

This story follows a young man who spent 19 years immersed in fantasy novels, always wondering what would happen if advanced technology were introduced into a magical world. On his nineteenth birthday, he tragically dies in an accident—only to be reincarnated into a realm filled with magic, dungeons, and beasts. Join him on his journey as he carves his own path, overcomes challenges, and shapes his destiny in this extraordinary new world. Stay tuned for his adventures and triumphs!

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Sex Contents: Some Sex | Genre: Fantasy
Tags: Consensual, Rape, Slavery, Lesbian, CrossDressing, Hermaphrodite, Shemale, TransGender, Farming, Futanari, High Fantasy, Military, Restart, War, Magic, BDSM, DomSub, MaleDom, FemaleDom, Humiliation, Light Bond, Rough, Sadistic, Spanking, Torture, PonyGirl, Harem, Lactation, Public Sex, Nudism, Royalty, Transformation, Violence
Downloads: 4927 | Votes: 117 | Score: 6.93
Size: 440KB | 78,664 words | Posted: in progress Updated:

102 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: 6396 | Votes: 54 | Score: 6.93
Size: 197KB | 35,957 words | Posted: Concluded:

103 Carl or Carla by Mystic47

A sister helps her brother dress up like a woman for a costume party.

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104 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: 914 | Votes: 20 | Score: 6.92
Size: 9KB | 1,758 words | Posted: in progress

105 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: 14126 | Votes: 44 | Score: 6.91
Size: 276KB | 53,177 words | Posted: Concluded:

106 Big John by Urtles53

The story of my first gay sex as a mature man with a mature man.

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107 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: 6865 | Votes: 107 | Score: 6.89
Size: 60KB | 11,464 words | Posted:

108 False Imprisonment by Bunts

A visit to a mornings magistrates court and the speed at which they dealt with girls of the night, gave me the idea for this story. Tony a transvestite gets convicted of being a prostitute and is sent to women's prison. The consequences are almost predicatable.

Premier members only

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109 The Awakening by Michele Nylons

A man awakes from a coma only to find he has selective amnesia. He doesn't know that he has a secret life. He is a closet transvestite. At first repulsed by the idea, he can't help exploring his secret life. What is it like to dress as a woman? What is it like to feel feminine? What is it like to suck a man's cock!

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Sex Contents: Much Sex | Genre: Erotica
Tags: Ma/Fa, Ma/Ma, Mult, Consensual, Romantic, NonConsensual, Reluctant, Coercion, Blackmail, Heterosexual, TransGender, CrossDressing, Shemale, Fiction, Cheating, Spanking, Rough, Gang Bang, Group Sex, Orgy, Oral Sex, Anal Sex, Masturbation, Petting, Analingus, Foot Fetish, Leg Fetish, Transformation
Downloads: 6559 | Votes: 83 | Score: 6.87
Size: 100KB | 19,283 words | Posted: Concluded:

110 Do It Yourself True Transvestite Story by Michele Nylons

I am a transvestite and it has taken me years to become adept transforming into a woman. It amazes me when I read so-called autobiographical stories about some guy who suddenly decides to and suddenly transforms from hairy man into a sexy stunning woman. I have written this story as a tongue in cheek dig at these stories. To read the story, just select any of the options a, through d, to put together your very own autobiographical "Grab Bag" story.

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Sex Contents: Minimal Sex | Genre: Humor
Tags: Ma/Ma, Coercion, TransGender, CrossDressing, Fiction, Sister, Uncle, Rough, First, Oral Sex, Anal Sex, Masturbation, Food, Flatulence, Exhibitionism, Voyeurism, Size, Transformation
Downloads: 1660 | Votes: * | Score: *
Size: 10KB | 1,951 words | Posted:

* Not enough votes to show score yet

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CrossDressing Stories

Displaying stories 101 through 110 of 351

101 Chosen by Chance by Vasantrutu

102 The Collector by Michele Nylons

103 Carl or Carla by Mystic47

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

105 Unconventional by Severusmax

106 Big John by Urtles53

107 The Lucky Gardener at the Girls School by Shani 34

108 False Imprisonment by Bunts

109 The Awakening by Michele Nylons

110 Do It Yourself True Transvestite Story by Michele Nylons

WARNING! ADULT CONTENT...