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CrossDressing Stories

Displaying stories 101 through 110 of 383

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101 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: 7110 Votes: 57 | Score: 6.96
Size: 197KB | 35,957 words | Posted: Concluded:

102 Adventures in Lifeguarding: Brian's Adventure by TMax

A Adventures in Lifeguarding Story
Brian comes "out of the closet"/"off pool deck" and it changes his life.
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Sex Contents: Minimal Sex | Genre: Coming of Age
Tags: Ma/Ma, Consensual, Gay, CrossDressing, Fiction, Oral Sex
Downloads: 1302 Votes: 39 | Score: 6.96
Size: 11KB | 2,276 words | Posted:

103 Undercover Angel by Michele Nylons

When Mike Harris stole two point seven million dollars in cash from his gangster boss, he knew that his life had changed forever. He has to get away and hide; his best disguise was to dress as a woman, but this had some implications that he hadn't though of. Dressed as the transvestite Michele he was sexy & attractive and men wanted to take advantage of her
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Sex Contents: Much Sex | Genre: Erotica
Tags: NonConsensual, Reluctant, Rape, Coercion, Blackmail, TransGender, CrossDressing, Fiction, DomSub, MaleDom, Light Bond, Humiliation, Gang Bang, Oral Sex, Anal Sex, Masturbation, Foot Fetish, Leg Fetish, Transformation
Downloads: 4781 Votes: 40 | Score: 6.94
Size: 126KB | 23,413 words | Posted: Concluded:

104 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: 15212 Votes: 45 | Score: 6.94
Size: 276KB | 53,177 words | Posted: Concluded:

105 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: 6834 Votes: 216 | Score: 6.94
Size: 26KB | 5,318 words | Posted:

106 Mister Henry Webster - 1875 by Techman1952

Ben and his sister are running from the law after robbing a bank in Pittsburgh, Pennsylvania. They go west by train to Kansas City, Kansas where their money runs out. They start walking, sleeping under bridges as they travel slowly toward Wichita. A fancy carriage stops next to them and the man driving asked them if they would drive for him. They end up taking the man’s name and pretend to be man and wife. Ben now Henry, becomes a well to do lawyer in Lawrence, Kansas. Read to find out how!
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Sex Contents: Much Sex | Genre: Western
Tags: Ma/Fa, Ma/ft, mt/Fa, Fa/Fa, ft/ft, Fa/ft, Consensual, Rape, Lesbian, BiSexual, Heterosexual, CrossDressing, Fiction, Crime, Historical, Western, Workplace, Incest, Mother, Son, Brother, Sister, Daughter, Torture, Group Sex, Interracial, Black Female, White Male, White Female, Oriental Female, Anal Sex, Analingus, Cream Pie, Exhibitionism, First, Fisting, Small Breasts, 2nd POV
Downloads: 3484 Votes: 78 | Score: 6.92
Size: 200KB | 38,848 words | Posted:

107 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: 2112 Votes: 49 | Score: 6.91
Size: 47KB | 8,758 words | Posted:

108 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: 2303 Votes: 67 | Score: 6.91
Size: 17KB | 3,506 words | Posted:

109 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: 749 Votes: 19 | Score: 6.89
Size: 9KB | 1,874 words | Posted:

110 Making Mum My Bitch by StJohnGeneral

My mother, who abandoned my father and me, returns. This is how I broke her into being my pussy slave.
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Sex Contents: Much Sex | Genre: Incest
Tags: Ma/Fa, mt/ft, Ma/ft, Fa/Fa, Fa/ft, Coercion, Reluctant, Gay, Lesbian, BiSexual, Heterosexual, CrossDressing, Shemale, TransGender, Fiction, True Story, Cheating, Slut Wife, Wimp Husband, Incest, Mother, Father, Daughter, BDSM, DomSub, FemaleDom, Humiliation, Rough, Spanking, Group Sex, Anal Sex, Analingus, Cream Pie, Double Penetration, Facial, Oral Sex, Squirting
Downloads: 4377 Votes: 40 | Score: 6.89
Size: 142KB | 27,805 words | Posted:
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