School Sissy Stories

109,522 results
Orientation
Length
Source
Infinite Scroll

More than Friends Ch. 01

by WillyShakes on Mar 26, 2019
Erotic Couplings

All characters are over 18. ***** When the "Fasten Seatbelts" indicator turned off, I jumped up immediately and pulled me backpack out of the overhead bin. The cute redhead I'd been seated next to looked up at me, the corners of her mouth curving up. "You look like you're in a hurry." I smiled back. "I haven't been home in a year. I can't wait to see e...

This Is Our Story Ch. 03

by Svalbarding on Feb 26, 2019
Novels and Novellas

"You fucked Hefty Hailey?!" "Did I say I had sex with her? No! I said we... messed around some." "Well I must say I'm certainly glad to see you seem to have retained your same basic shape," said Owen. When Conner looked at him quizzically, he explained. "You know. Because of smushing." "I got it. Shut up." "How much, would you say? Deuce, deuce and a hal...

Angel From Montgomery Pt. 01

by jack_straw on Sep 12, 2017
Erotic Couplings

Author's note: This is an entry in the fourth semi-annual Jake Rivers "invitational." The initial one was based on the Statler Brother's song, "This Bed of Rose's." The second used the Marty Robbins El Paso trilogy: "El Paso," "El Paso City," and "Faleena." The third had stories based on the various versions of, "Maggie May," or "Maggie Mae." The current i...

Nothing is Ever What It Seems Ch. 02

by Ascii on Sep 16, 2017
Romance

Hi there, Sorry for delay, my laptop broke last week so I had a busy week trying to get it fixed. I will finally be getting it back on Thursday, so I can start on the next chapter. Anyhow Jen, I hope you have a speedy recovery, thanks again for the edit -- any mistakes found are my fault. CVC thanks for the insight, again you've made it a better read! Than...

New City, Old Friends

by javalover5050 on Sep 12, 2017
Loving Wives

Sitting here totally satiated for the first time in my life...I guess...physically satisfied and very sore...waiting on my husband to arrive home from his business trip ...guess I better start at the beginning. Last year we moved to Greenville, SC for Ron's work. Ron is my husband of 12 years now. My name is Tracy. We met in college, fell in love and the re...

Julia

by Christie052780 on Sep 16, 2017
Mature

Disclaimer: the author does not condone or promote the activities in this story. It is just a story. * * * When my parents broke up my mom and I moved out to California and I started high school with a bunch of kids I didn't know. The first year was pretty awful and I longed to move back home to North Carolina with my dad. My mom had been awarded full cust...

Wild Cat

by Katiecat on Sep 12, 2017
BDSM

Cat squirmed on the hard wooden chair and watched the seconds tick by on the clock. 4:55 on Friday afternoon. Five minutes until doomsday. She worried at an almost non-existent hangnail, nibbling it smooth. Was she a glutton for punishment? Had a death wish, perhaps? She smiled ruefully to herself. Why, oh why, was it so hard to get kicked out of school? T...

Summer Job: Clothes Shopping

by EriAliSaa on Aug 30, 2017
Exhibitionist & Voyeur

Another summer had come and I was back home again. My room was pretty much as I had left it. The stuffed animals, that just a few years before I didn't think I could live without, littered the bed and formed small communities about the room. I was much more a woman of the world (or so I thought), the life in the dorms, and then later with roommates off campu...

High School Reunion

by phoenixcinders on Sep 18, 2018
Transsexuals & Crossdressers

All characters are over the age of 18. *** Finally walking off the plane from my first class seat on a Thursday evening. It feels good to be home. I'm back in town for my 10-year high school reunion. This time I'm going to be the one everyone's jealous of. I've got the perfect job, making more money than I know what to do with. Well... being an accountant...

The Elephant in the Room Ch. 02

by MicheleNylons on Apr 17, 2018
Transsexuals & Crossdressers

Chapter Two: Elizabeth Elizabeth's first memories were of being poor; that is to say her mother was poor and alone having been abandoned by her husband, Elizabeth's father. Her mom cursed her ex-husband and men in general but she schemed and connived and using her good looks, her intelligence and her considerable sex appeal she landed another man, a better...