CrossDressing Stories

Displaying stories 181 through 190 of 360

181 Eleanor's Descent by niteowluk99

The original story about how I met Eleanor, very little by way of sex.

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Sex Contents: Much Sex | Genre: BDSM
Tags: Ma/Fa, Fa/Fa, Mult, Consensual, Romantic, NonConsensual, Reluctant, Coercion, Mind Control, Slavery, BiSexual, Heterosexual, CrossDressing, True Story, BDSM, DomSub, MaleDom, Spanking, Humiliation, Sadistic, Group Sex, White Couple, First, Oral Sex, Anal Sex, Masturbation, Sex Toys, Water Sports, Enema
Downloads: 8115 | Votes: 58 | Score: 6.37
Size: 89KB | 17,281 words | Posted: Concluded:

182 King's Scepter Boy by ChrisCross

The fourteen-year-old Filipino towel boy at a New Orleans French Quarter male brothel, Mama Rosa's, gets initiated with the rubber hand-tipped scepter of a former Mardi Gras king.

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Sex Contents: Much Sex | Genre: Erotica
Tags: Ma/mt, Consensual, Rape, Gay, CrossDressing, Shemale, Fiction, Crime, Workplace, MaleDom, Light Bond, Rough, Spanking, Interracial, White Male, Oriental Male, Anal Sex, Analingus, First, Oral Sex, Safe Sex, Sex Toys, Size, Prostitution, Violent
Downloads: 1046 | Votes: * | Score: *
Size: 13KB | 2,695 words | Posted:

183 Raised by Strippers - A Trans Story by Shirley Wanton

A Raised By Strippers Series Story (1)
This is the story of the son of a stripper, raised in the dressing rooms of strip clubs and evolving into the Trans woman she was always meant to be.

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Sex Contents: Some Sex | Genre: Erotica
Tags: Consensual, BiSexual, CrossDressing, TransGender, Fiction, Anal Sex, Exhibitionism, Oral Sex
Downloads: 4216 | Votes: 81 | Score: 6.36
Size: 33KB | 6,763 words | Posted: Concluded:

184 Warm and Welcoming by yfnsp

After losing his job, a widower moves in with his stepson and offers to keep house for him until he can get back on his feet. But he finds that his new role, making a home warm and welcoming, is not only rewarding but also transformative.

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185 Mom's Concern by Chas

Two moms catch their sons masturbating together while wearing the moms' panties and bras. The moms are worried about sons being cross dressers or gay. The sons explain they had never seen a woman before and were fantasying. The moms decide to show them the real thing.

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Sex Contents: Stroke Story | Genre: Incest
Tags: mt/Fa, Fa/Fa, Consensual, Lesbian, Heterosexual, CrossDressing, Incest, Mother, Son, Oral Sex, Masturbation
Downloads: 5943 | Votes: 199 | Score: 6.35
Size: 7KB | 1,389 words | Posted:

186 World's Record by Tasty Little Pop Tart

Matthew has the weekend to himself, alone at the condo. He's under severe restrictions, however, imposed by his Mom. Matthew is 14 and not old enough to be home alone for the weekend. His sister Casey gives him something to keep him occupied while they're gone. Neither has any clue what's really going on, or the consequences.

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Sex Contents: Much Sex | Genre: Erotica
Tags: mt/Fa, Consensual, Reluctant, BiSexual, Heterosexual, CrossDressing, Fiction, Extra Sensory Perception, Incest, Brother, Sister, First, Anal Sex, Masturbation, Sex Toys, Exhibitionism
Downloads: 11523 | Votes: 109 | Score: 6.34
Size: 116KB | 21,612 words | Posted:

187 Troy by Its a skirt, not a kilt

A boy tries on his sisters wedding dress, only to be discovered by the groom to be...

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188 Say Hello to Georgette by sourdough

Carla's kiss came with a price.

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189 The Beauty and the King by Obsessive_Lesbian

Carol King was the lesbian who used to pass as a man. Big Bro procured call girls for her every week. One night, however, he demanded a raise in his commission for obtaining the call girls as her sexual partners. Carol reluctantly made the deal with him before taking Dee as her girlfriend for 72. The prolonged GFE session turned out to be a momentous opportunity for both the girls to accept each other as life partners.

Premier members only

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Sex Contents: Much Sex | Genre: Erotica
Tags: Fa/Fa, Consensual, Romantic, Lesbian, BiSexual, CrossDressing, Oral Sex, Petting, Sex Toys, Squirting, Size, Big Breasts, Slow, Prostitution
Downloads: 2142 | Votes: 26 | Score: 6.32
Size: 71KB | 12,712 words | Posted:

190 Addiction by Baron Darkside

Her addiction to sex, and lack of response from her husband, leads her to situations where she shouldn't be...

Premier members only

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Sex Contents: Much Sex | Genre: Incest
Tags: Ma/Fa, mt/Fa, Teenagers, Consensual, Blackmail, CrossDressing, Cheating, Incest, Mother, Son, First, Voyeurism
Downloads: 78772 | Votes: 169 | Score: 6.31
Size: 185KB | 34,175 words | Posted:

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CrossDressing Stories

Displaying stories 181 through 190 of 360

181 Eleanor's Descent by niteowluk99

182 King's Scepter Boy by ChrisCross

183 Raised by Strippers - A Trans Story by Shirley Wanton

184 Warm and Welcoming by yfnsp

185 Mom's Concern by Chas

186 World's Record by Tasty Little Pop Tart

187 Troy by Its a skirt, not a kilt

188 Say Hello to Georgette by sourdough

189 The Beauty and the King by Obsessive_Lesbian

190 Addiction by Baron Darkside

WARNING! ADULT CONTENT...