School Sissy Stories

109,522 results
Orientation
Length
Source
Infinite Scroll

For The Love Of Art

by Starlight on Sep 17, 2017
Mature

My name is Jenny Blithe. At the time of writing I am in my mid fifties. I have been married once, to Tom, who died in a skiing accident about five years after we got married. I have had two lovers since then, but neither of them worked out, the first turning out to be a lout, and the second a foul-mouthed pig. After that I gave up and contented myself with a...

Friends Ch. 01

by foobus on Sep 13, 2017
Non-Erotic

Ch. 1 Progressive Dinners Following is a story of fact and fiction. The initial progressive dinner took place exactly as presented. What happened afterward is pure fiction, but fiction couched in the context of the social network that grew as described and existed for several years. This chapter is almost completely background, developing the main character...

Unicorn Dreams Ch. 02

by Tara_Neale on Sep 15, 2017
Romance

I woke up the next morning in the most delicious way possible...a smiling cowboy holding a big cup of coffee. "I don't know how you like your coffee so I made it ranch style: hot, strong, black and sweet. I figure you can use the sugar rush and caffeine kick," he said with that sheepish little boy grin. I rolled over and smiled as I took the cup of coffee...

Claire and Sarah Ch. 01

by creamofsomeyoungguy on Aug 31, 2017
Group Sex

Claire and Sarah both looked up to me. Claire had just turned 18. Like me, she was just finishing her senior year in high school. Unlike me, she was extremely naïve and impressionable. Sarah was also 18 but had been so for several months. Despite being very intelligent and talented, Sarah lacked self-confidence. Both girls relished their time spent with me b...

The Snowball Effect Ch. 01

by Bigdenverman on Sep 17, 2017
Loving Wives

I paced nervously. My doorbell rang. Allison was here. Time to jump in with both feet and hope for the best. "Hey, come on in," I said, opening the door and welcoming her. She leaned up and gave me a peck on the cheek. I took her coat and hung it in the front closet. "Hi, Ryan. Wow, you cleaned up the place," she teased. "Nice…" "Thanks," I responded awkw...

Nursing Friend

by tool_time2005 on Aug 19, 2017
Erotic Couplings

Several years ago I made a trip back to my hometown to check on my elderly mother who was hospitalized. I had not lived in the town since my high school days and had lost track of most of my old acquaintances. On one of my first trips to the hospital I heard someone call out the nickname I had in grade school. I turned expecting to see a relative or old frie...

The New Year

by thehotness on Sep 12, 2017
Exhibitionist & Voyeur

My alarm clock buzzes, and I don't move to turn it off. I'm lying in my bed, sweating despite the air-conditioning and the fact that I'm naked. It's a cold sweat. I feel empty, and realize the seven-inch vibrator that I had fucked myself to sleep with had slipped out of me during the night, and was lying silent on my bed between my legs. I lie back, and reme...

Lena at School

by TrashyDreams on Apr 9, 2019
Toys & Masturbation

On a rainy Friday morning, Lena walked down the hall awkwardly trying to keep her legs as parted as possible without expelling it. It being the remote controlled egg Liam made her put in her this morning. He promised to randomly turn it in on, throughout the day, when he was bored in the office. She wasn't sure exactly what Liam had in mind when he first me...

No Strings Attached Ch. 08

by Tara Cox on Apr 13, 2020
Romance

Chris was already waiting at the chain coffee shop where they had arranged to meet. Jon was running a bit late today. He had woken on Alicia's couch; his daughter was staring down at him with a huge grin, dancing from foot to foot and exclaiming his name. Alicia was trying to get her ready for school, and Alison had already left for the diner. He had offer...

Orgasm Inc.

by Sottovoce on Sep 14, 2020
Exhibitionist & Voyeur

I was crashing over the lip of amazing orgasm and having my g-spot pounded mercilessly when my boss walked in on me... Wait, wait, I'm telling this in the wrong order. I probably shouldn't start with the climax (ha ha), but with the beginning. I'll come back to that orgasm... ++++++++++++++++++ My name is Abby and six weeks ago I was finishing my Bachelor...