Sissy Schoolgirl Stories

13,642 results
Orientation
Length
Source
Infinite Scroll

Friend's Husband

by StoryTeller07 on Sep 12, 2017
Loving Wives

Wife and friend compete for the husband "Another?" Dorothy said. "Do you need to ask?" Elizabeth answered, holding out the wine glass. "It's been too long. We should have kept in touch." "You know how it is. A day goes nowhere. That's how I lost Harry, working too many hours." Dorothy looked at her friend feeling sorry for her. They had been best friend...

LilBostonBianca

by erikalilpryncess on Sep 14, 2017
Transsexuals & Crossdressers

In high school I had spent a lot of time on the internet, and even though I considered myself completely straight and had a serious girlfriend my entire senior year, I knew that deep down I found the images of transvestites wearing slutty clothing on the internet incredibly erotic and that I wanted to try it sometime. As a result I had finagled my way into...

Karen's Photo Shoot

by eroslit on Aug 31, 2017
Group Sex

"Oh, my God, Ashley. These are fabulous," Karen cooed. She clicked the mouse and another picture filled the monitor. Karen stared at it while her friend stood nervously behind her. Ashley dearly wanted Karen to like the pictures so she could talk her roommate into posing, too. "Your hair is perfect. He did a great job of getting the color," Karen said, swit...

Club Dragon's Fire: The New Bytch

by WickedOne on Sep 11, 2017
BDSM

"What do you mean I’m fired?" she scowls. "I told you, no more fights." "Fight? You mean last night when I punched the guy for grabbing all the twenties from Jamie's till?!" "It was still a fight." he says solemnly. "What the fuck!" she looks at Jamie, "Tell him this isn't right. You already said I saved your ass!" "Yes, you did save me, but Howard has...

Navy Wives-Erica Ch. 03

by HappyWife85 on Sep 13, 2017
Interracial Love

It was Saturday morning. Erica lay awake in bed. She heard activity downstairs. Robert had always been the early bird, even on his days off. The past week had been great for Erica and she was loving every bit of it. Sex with Tre had put her walking on clouds, and it showed. Two of her female co-workers had even commented about it, saying that she had a glow...

My Wife the Womanizer

by Couture on Sep 25, 2017
Transsexuals & Crossdressers

The doorbell rang and my heart galloped, as it always did whenever the bell rang. If I kept totally focused on what Mistress wanted, everything was usually okay. However, unforeseen events, like doorbells for instance, almost always spelled trouble. I hurried to find my Mistress and curtsied automatically as I entered her room. "Mistress, there is someone...

Meeting My Domme While Shopping Ch. 02

by TheDarkCloud on Sep 25, 2017
BDSM

Previously... While out shopping with my wife I came across the Pro Domme I used to secretly visit, Mistress Allison. She took the opportunity to humiliate me and force me back into visiting her and also began to take a not entirely healthy interest in my wife Christina. * COLIN'S NIGHT I reached for the gin bottle and with a slightly shaking hand poured...

The Neighbour Ch. 03

by jerrycross on Sep 18, 2017
Transsexuals & Crossdressers

I returned home after a full day of work and almost ran into the house. I was greeted by my wife, Helen at the door. Beside her was her bags of luggage all packed and ready to go. I carried on with her as normal and we said our goodbye's, she was heading out of town business. But as she walked out the door I felt as if she was hiding something. She almost se...

The Royal Cock Ch. 25

by sexgundam666 on Sep 19, 2017
Novels and Novellas

Author's Note: Thank you to all who stayed with this series over the weeks. Sorry for the overall slow lead into the sex, but I wanted to try something a bit different this time. Be sure to leave some feedback, as detailed as possible (if anyone is so inclined), so I know what to carry over for future stories and what I should work on. Again, thank you all....

Becoming Hers Ch. 07

by fpat97 on Nov 6, 2017
Fetish

After five days locked up, Alex wasn't sure how he was going to handle this. Last week, Karen had made him cum and eat it every night as punishment and this week his body was still expecting that treatment. Plus, he was supposed to edge himself every day in the shower! The first few days weren't so bad, but now getting back into his cage was a challenge. He...