Sissy Cheerleader Stories

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Orientation
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Little Panties for a Little Cock

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

It was Saturday morning and I decided to get my laundry done before going out for lunch. I took my stuff down stairs to the basement laundry room, loaded a washer and started the cycle. I was about to go back up to my place when I noticed a basket of laundry on the table. I went over and found a mix of girls and guys stuff, I guessed they belonged to the you...

The New Neighbors (Black Femdom)

by Dunn81 on Aug 12, 2019
BDSM

Hi my name is Julia i'm 42 years old and i'm with my daughter Sofia who's 20. I'm a pretty fit girl who are vegan. I Lost my husband 5 years ago and since that i never dated anyone. I'm a 5'2 brunette with medium size boobs and a medium sized ass too. I weighted around 130 pounds. My Daughter is 5'5 big boobs and small ass. She trained at the gym a lot since...

Keith's Caught in a Costume

by gaildaniels84 on Dec 24, 2019
Transgender & Crossdressers

It was the giggling that began to pull Keith out of his head. Sitting in English class, halfway through the fall of his senior year of high school at St. Michael's Catholic, Keith couldn't find the energy or heart to care about Hester Prynne or her scarlet letter. So, he'd let himself drift off into fantasy. This fantasy - like many of his since the beginnin...

X-Change

by Noah_Peal on May 15, 2015
Miscellaneous

Pills Pink pills change males to females. Blue pills change females to males. Purple pills (X-Trans) change males or females into transgenders, can be combined with pink or blue. X-Change (Formula subject to change) Acquired from unlicensed "street" vendors. Changed (defective/in testing) formula. Cheapest. High pregnancy risk. Can lead to mental a...

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Sarah had to Wear Little Panties

by SarahCD on Dec 25, 2018
Transgender & Crossdressers

I first published this story a few years ago. Since then, my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected some grammatical mistakes. ------------------------------------------------------- It was Saturday morning and I decided to get my laundry done before going ou...

Madame Jenoix

by Candour on Sep 26, 2017
Transsexuals & Crossdressers

Chapter 1 --------- A young looking and slight 18-year-old boy sits outside the Headmistress's room, obviously feeling anxious. His legs kick back and forth under the chair and he keeps looking up at the door. His uniform looks unkempt, like he has just thrown it on after Games. After some long, countless minutes elapse, he hears a loud, slow "Come!" from...

Halloween Crossing

by DrLuverotica on Sep 18, 2017
Transsexuals & Crossdressers

It all started off so innocently... My wife Jo, tall, slim, blonde, aged 40 with 34DD tits and the sexiest big ass imaginable, works as a doctor. Her hours are long and arduous. She often comes home completely worn out. Only during the holidays does she tend to recover her sparkle. She is gorgeous, but recently our sex life has become a bit humdrum and mund...

Fetish & Fantasy Pt. 01

by GavinIsaNuisance on Jul 13, 2020
Transgender & Crossdressers

This work is completely fictitious, any similarities to any persons living or dead is purely coincidental and entirely unintentional. All persons depicted in naked/sexual acts are 18 and up. Down and out aspiring model Taran Kilkenny becomes the hottest commodity in an escort service for trannies! But first he's gotta get trained by his new and domineering b...

Man to sissy

by fortifiedfortfightinfortnite on Jun 15, 2018
Fetish

I had asked out one of the cutest girls in school. Alex, being a cheerleader had no problem picking a quarterback, but to my luck I had worked up the courage to ask her and she excepted! When I had got to her house, I rung the doorbell, As she opened the door her aura enveloped me. When she invited me inside I didn’t hesitate. She then lead me and said, I co...

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Caught Out, Made Over

by TanyaCc on Oct 5, 2020
Transgender & Crossdressers

It had finally happened. To be honest, I shouldn't have been that surprised. But here I was, dressed in my favourite sissy school gurl outfit, heels on, lipstick, wig and chastity cage in place, bent over the kitchen bench, getting reamed to the hilt by an 11 inch dildo on the end of my own fucking machine. I had cum dripping down my thighs, moans and groans...