Sissy Cheerleader Stories

12,762 results
Orientation
Length
Source
Infinite Scroll

Carol's Gifts

by Belongs2Beth on Sep 16, 2017
BDSM

Authors note: This is the third story featuring characters introduced in "Carol's Christmas." In this installment Carol give's Jack his Christmas gift one night late with the help of Irena, "Marcia" and several well hung younger men. The sex action in this story is unrestrained, and since the tags are at the bottom of the page, I will issue the following mil...

First time Sissy

by PR Sissy on Sep 29, 2019
Transsexual

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any s...

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Sissy Slut Boy

by SissyBoiToi1 on Jan 2, 2017
Fetish

You wake up in your bed, in your attic bedroom. You sigh, not wanting to get out of bed. But then, you realize 2 things--one, your alarm clock didn't go off, you overslept! You have 5 minutes to get to the bus! And two--your bed is soaked in warm, smelly liquid. Did you wet yourself? (Just a note: The "catch the bus" route leads to diaper-related c...

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Black Licorice

by EROTICbearscribe on Oct 19, 2020
Transgender & Crossdressers

My name is Jamie. I am 19 years old. This is the story of what happened to me Halloween one year ago. It was the last week of October and the leaves had turned brilliant shades of orange, red and yellow. The nights were getting cooler. Everything you could imagine was pumpkin flavored. Usually I get psyched for this time of year but things were different f...

Skins vs Boys

by Couture on Sep 14, 2017
Fetish

Please do not read if under 18 years of age, or offended by sexually explicit stories and situations. (TG, FM, femdom, anal) (c) 2001 Couture * * * * * The biggest football game of the year was almost over, and my husband sat next to me angry and blushing in humiliation, while I cheered. Call me a bitch, but I took extra pains to rub it in. "Wahooo! The Sk...

Trapped! Pt. 01

by TheEroticProspero on Jul 6, 2020
Transgender & Crossdressers

Trapped Part 1: A Trap Is Sprung As a teacher, I shouldn't admit this. But sometimes you have students you just hate. And for almost a year I had hated Jessica Dane. I was only 25, fresh out of university, straight into a job teaching English. For all my life I was poor, short, thin, and pale. My only saving grace appearance wise was my long, rocker...

OMG Mom!

by TheSecretlyUnlikelyDuck on Feb 5, 2019
Interracial

You pull into the driveway of 15 Preston Road at around 3pm on a friday afternoon. The light of the late spring sun pours over you as you come to a halt, parked behind the red BMW belonging to Mary Lange. She is a gorgeous blonde, who looks far younger than her actual age of 39, and is unarguably the head of the Lange household. You don't see her husband's c...

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Mistress Chantel, Tranny Dominatrix Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Prefix: Welcome to my next erotic story. This story will be written from the point of view of a Transvestite Dominatrix. It is a new twist in my mindset as I normally identify as submissive and as a sissy maid and slut to a dominant Master. It's my 'kink' but I have danced around in my mind a story from a position of Chantel being a true Transvestite Dominat...

The Cock Clock Ch. 04

by HarveyMarcus on Sep 26, 2017
Erotic Couplings

WARNING: The following story is for the entertainment of ADULTS ONLY, and contains descriptions of explicit sex. If you are not an adult, or reading sex stories upset you, or you are offended by subjects of a sexual nature - do not read any further! This story is for entertainment only. It contains adult oriented material. This is a work of fiction. The a...

Sarah was Made into a Sissy

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 and wait for my things when I noticed a basket of laundry on the table. I went over and found a mix of girls and guys stuff, I guessed t...