CrossDressing Stories

Displaying stories 291 through 300 of 353

291 Guy & Margo by Lovelaced

A well-hung college boy returns home and seduces his attractive Mom! Margo is torn between her natural sexual urges and the need to remain a respectable mother. But Guy's hold on his Mother slides as she gradually takes control and wants Guy to be more like a girl in bed. Guy becomes Gill who looks great in a skirt and heels - that's the way Margo likes it ! They'll be out on the town before you know it!

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292 Maid in Enclosed City by Anonymous (Enclosed City)

A Story in the Enclosed City Universe
A boy wakes up from a drug-induced stupor in a strange-looking basement. He can't seem to remember who he is, and what's worse, he is now expected to dress like a maid and follow every order given to him. (This story contains gay rape and straight romance.)

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Sex Contents: Much Sex | Genre: BDSM
Tags: mt/ft, Ma/mt, Consensual, Reluctant, Slavery, Gay, Heterosexual, CrossDressing, Fiction, MaleDom, Humiliation, Gang Bang, First, Masturbation
Downloads: 2243 | Votes: * | Score: *
Size: 43KB | 8,227 words | Posted:

293 Naked on Summer Vacation: Sissy Summer School by Eddie Davidson

A Summer Vacation Story (1)
Part of the Davidson Family Stories universe
It was 1980-something and this mostly true story about summer with my Aunt contains spanking, humiliation, nudity etc as she treats me like my younger cousins on the beach. "Get those swimsuits off! You aren't getting in the car all wet and sandy!" **This is a prequel to Naked on Summer Vacation: Slut Summer School. It involves feminization and establishes a lot of the background.

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Sex Contents: Minimal Sex | Genre: Coming of Age
Tags: Teenagers, Reluctant, BiSexual, CrossDressing, Shemale, Cousins, Aunt, FemaleDom, Humiliation, Light Bond, Spanking, Masturbation, Voyeurism, Small Breasts, Nudism, Transformation
Downloads: 19978 | Votes: 145 | Score: 5.60
Size: 431KB | 86,869 words | Posted: Concluded:

294 Homosexual Husband by Keven-Jeanne Bardot

A closeted married homosexual has an affair with a handsome co-worker, and decides to embrace his homosexuality.

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Sex Contents: Stroke Story | Genre: Erotica
Tags: Ma/Fa, Consensual, Romantic, Gay, CrossDressing, True Story, Cheating, Anal Sex, Masturbation, Oral Sex, Porn Theatre
Downloads: 1381 | Votes: 25 | Score: 5.59
Size: 6KB | 1,285 words | Posted:

295 Miss Kevyn-jeanne Bardot by Keven-Jeanne Bardot

Cross dressing sissy boy Keven, encourages his sexy Filipina wife to date black men. Keven is such a feminine little sissy, who enjoys helping his wife do her hair and nails before she goes out on a date!

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Sex Contents: Stroke Story | Genre: Erotica
Tags: Ma/Fa, Consensual, Gay, CrossDressing, True Story, Cheating, Cuckold, Slut Wife, Wimp Husband, Humiliation, Polygamy/Polyamory, Interracial, Black Male, White Male, Oriental Female, Anal Sex, Analingus, Cream Pie, Exhibitionism, Oral Sex, Public Sex, Porn Theatre, Prostitution
Downloads: 1258 | Votes: 20 | Score: 5.58
Size: 17KB | 3,517 words | Posted:

296 Foster Home Girl by Diane Destry

Pearl was shunted from one home to another with a lot of disappointments along the way. She is already over eighteen but is on the books as only sixteen by mistake. She is an oral sex trainee, but is still a virgin below the belt. Now she wants to be skilled in all areas of the sexual spectrum including vaginal and anal penetration. She finds a likely candidate in Coach Reed, divorced and whose only female contact is with escort girls on Saturday nights. Now she has a date to remember.

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Sex Contents: Much Sex | Genre: Coming of Age
Tags: Ma/ft, Teenagers, Coercion, Consensual, NonConsensual, Lesbian, Heterosexual, CrossDressing, Fiction, Slut Wife, Wimp Husband, Incest, Brother, Sister, Humiliation, Rough, Spanking, Group Sex, Anal Sex, Cream Pie, Exhibitionism, First, Masturbation, Oral Sex, Safe Sex, Voyeurism, Size, Teacher/Student, Prostitution, Violent
Downloads: 5174 | Votes: 58 | Score: 5.57
Size: 22KB | 4,242 words | Posted: Concluded:

297 Absence of Choice by The Ghost In The Machine

This is the story about a young man , who is is blackmailed into submission by a black guy.

Premier members only

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Sex Contents: Much Sex | Genre: Erotica
Tags: Ma/Ma, Mult, NonConsensual, Rape, Blackmail, Drunk/Drugged, TransGender, CrossDressing, MaleDom, Gang Bang, Interracial, First, Anal Sex
Downloads: 21178 | Votes: 88 | Score: 5.57
Size: 45KB | 9,391 words | Posted:

298 Mom's iPhone by Shoeslayer

Mom's son Harold not only gets turned on by his mom's half-glasses but puts his pics on her iphone as well. Mom comes across the pics and loves them. Things hapen when she drops in one night to take pics

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299 A Visit to Matilda's by Freddie Clegg

When Andrew Meakin encourages his girlfriend to indulge his kinky tastes, she decides that Matilda's School for Male Maids is the best place for him to start learning what SHE expects.

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