Sissy Cheerleader Stories

12,762 results
Orientation
Length
Source
Infinite Scroll

Jesse's Journey Down a Rabbit Hole Ch. 20

by sadkins116 on Sep 25, 2017
Illustrated

Janice slowly walked towards her car. Today was the worst day of her life. It started out having to serve the construction workers modifying her house. They had already been there for two days. The first day was bad enough, but the second day was worse. Now that they knew she was the house slut, they took advantage of her constantly. Janice hated the big man...

Trapped and Trained Ch. 18

by SissyIndy on Sep 25, 2017
Transsexuals & Crossdressers

I don't remember much to how I got here from the previous night, mostly just flashes. I remember the limo pulling into the parking garage and seeing the redness behind my eyelids as we passed under the various lights before it crept to a stop in front of the elevator. Mitch climbed out, then Vivian stirred me awake and led me out, still wearing just my red l...

My Exhibitionist Instructor

by sandlotkid on Sep 13, 2017
Loving Wives

I was excited to hear the news that my manager was sending me to a weeklong training session. Currently I don't travel often for business, so I always enjoy the few trips that come my way. I've already realized that frequently, the city one visits on a business trip doesn't really matter too much - often there's not enough free time to get out of the hotel a...

College Girls Take On Developers

by msgrant67 on Sep 12, 2017
BDSM

Chapter 1: Introduction During Spring Break of our senior year at Florida State, my friend Chelsea convinced another friend, Samantha, as well as myself to come home with her to Rome, Georgia, to relax a bit. This was out of character for us, as wild, beach vacations were more the norm, but we had gotten into a bit of trouble the year before in Daytona duri...

Alice’s Addiction

by JordonLynn on Sep 13, 2017
Interracial Love

Alice had a problem. Actually, it was more of an addiction; as much of a monkey on her back as any heroin junkie carried around with them. The first inkling that this "problem" would be with her for the rest of her life came at an early age and it all began innocently enough with a Popsicle. Alice had been sucking on it, sliding it in and out of her mouth,...

For the Love of Peggy

by IraBumblefield on Sep 14, 2017
Loving Wives

For the Love of Peggy - He loved her, but she loved another. A story of how unrequited young love changed with time. It takes place in the late sixties and early 1970s, a time when the flower children of the baby boomers were leaving their teens, a time before the internet, before DNA testing, before birth control pills were readily available for single wom...

Sexual Discovery

by ainu2 on Sep 14, 2017
Erotic Couplings

I'm six feet five inches tall, weigh 218 pounds. I played football and am now on the track team, so I work out regularly and am in extra good shape. I just turned eighteen and in another two months I'll graduate from high school. I plan on going to the local community college to study nursing. I know, nursing is mostly a female profession but my Mom is a nur...

Nikki

by markchamberlain on Sep 14, 2017
Exhibitionist & Voyeur

"Can I come in?" "Of course, Nikki, what's wrong...?" I was concerned as I opened the screen door and let Nikki in. I didn't know my neighbor very well - we had had a number of casual conversations in the front yard in the year since she and her husband moved next door. So I was somewhat surprised to find her at my doorstep, with tears in her eyes. "Oh it'...

Recycling

by Onagerian Surmise on Sep 14, 2017
Loving Wives

Recycling Prologue One of my fond childhood memories was going to the dump with my dad. In those days, "the dump" was a big hole or pit dug in the ground, big as half a football field. Most of the dirt from the hole was trucked out and used as landfill somewhere else. People paid a few bucks at the entrance, drove to the edge of the pit, and threw stuff...

I've Got a New Girl Now

by eroticognitive on Sep 16, 2017
Letters & Transcripts

A story inspired, in its own way, by the Honeymoon Suite song, "New Girl Now." I got a new girl now And she's a lot like you ***** Dear Mandy, I'm sorry it's taken me so long to return these last few things to you. Some of these things we shared I couldn't bear to let go of until now. Like that fuzzy pink teddy bear I won for you at that county fair we...