Sissy Cheerleader Stories

1,000 results
Orientation
Length
Category
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...

The Size Matter Society Pt. 00

by Ana Hanz on Apr 22, 2025

Chapter 00 - Prologue (How everything started) The transformation of our world from a capitalist society to a society where penis size determines social hierarchy was a long and tumultuous process, shaped by a multitude of factors and forces that worked together in complex and often unpredictable ways. Yet, at its core, this transformation can be traced back...

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...

Cheerleader Humiliation Ch. 01

by ButtPlugBitchBoy on Sep 17, 2017
BDSM

Shivering, cold, feeling weaker than ever before, I look up at them with my heart beating a million miles per hour. From my vantage point... the dim wet tile floor of the girls locker room at my high school, they seem to tower over me like strange Satanic titans. I'll capitalize the letters in titans that were most obvious; TITanS; TITS. I can see their pa...

A Sissy Saga Ch. 23

by Snurge on Sep 15, 2017
Novels and Novellas

Mrs Pardoe's heart pounded like steam-hammer as she made her way to her room. It had been such a long time since she'd had a young girl to herself, to take command of, to admire and to love, and she knew Mrs Amos's niece Lizzie was a real doll. On the way she passed the Joanna television-person ensconced with Gloria in the stair well of the third floor, bot...

A Sissy's Date Night

by nadia603000 on Oct 19, 2020
BDSM

Author's Note: Mistress Pepper and Sophie are "anonymized" versions of me and my slave-girl. The real me. All of my stories are (or should I say will be) my memories of a session with a sub. Thus, they are true stories. Only in this version details have been changed to protect the sub. I do live in Mobile about 10 months of the year (the remaining two I spe...

Sissification 101: Ch. 01

by silkstockingslover on May 4, 2020
Fetish

Summary: Straight guy is caught watching sissy porn and...Note 1: Thanks to Eric who requested and helped plot this lengthy story. Note 2: Thanks to Tex Beethoven and Robert for editing. Note 3: All characters are at least 18 years old. Sissification 101: Ch. 01 1. MY SISSY CURIOSITY I've always liked nylons. I grew up when they were still popular and...

Dede does Joseph

by Newkinkstories on Sep 14, 2017
Erotic Couplings

She stood five foot eight and one half inch. A former cheerleader, she now taught at the local Catholic school. Her blonde hair, green eyes and large 36DD breasts were the cause of many a wet dream for the teenage boys in her class, but Dede wasn't taking any chances with them. She and her best friend Jennifer worked together and always made sure they were...

HypnoSissy: Becoming a Cocksucker

by silkstockingslover on Sep 18, 2017
Fetish

Summary: Straight guy watches porn tapes that are not what they seem. Note 1: Thanks to hfernandez1983 for the story idea and the intriguing revelation that hypno sissy videos exist in the first place. Note 2: Of course, all participants are at least 18-years-old. Note 3: Thanks to goamz86, Robert, DomMasterJim and Wayne for editing. Category: This...

Teacher Wife Goes Black

by easyballs on Nov 25, 2017
First Time

This story is about a married wife who makes her small dick husband a sissy slave, and eventually finds some real cock to fill what she has been missing but it comes from an unexpected source. If this type of story offends you fuck off and read the beano or something negativity I get daily, so it won't be new to me. ***** As I sit here writing this I am na...