Literotica Wearing A Butt Plug To School Stories

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Caroline the Teenage Bum Slut

by lordodie on Sep 25, 2017
Anal

Caroline the Teenage Bum Slut (Redux -- Chapter 1) Originally by: Jason Hitchcock Adapted by: LordOdie & FantasyWriter1 Disclaimer: The following is a work of pure sexual fantasy and is intended for adult audiences ONLY. If you are under the age of 18, please stop reading NOW and go tell your parent and/or guardian that you need stricter internet supe...

My Life as a Crossdresser Ch. 01

by asian_CD on Sep 16, 2017
Transsexuals & Crossdressers

Hi, This is my first ever attempt at writing a story so I would appreciate constructive feed back. Also, this is just mainly set up and background info with only a masturbation scene. Some of the following events are true and did happen to me. ********************************** It has been five months since I turned 18 and thankfully, high school was in...

Bought By a Rich Man

by humiliationexpert on Sep 13, 2017
Fetish

Stacey wondered how it had come to this. There she was standing in an airport waiting at the busy gate to board a plane to Ibiza with her shorts down around her ankles. She could feel her face getting redder and redder as the giggles from the other passengers got louder and more noticeable. She had been told to wait a full 3 seconds before picking up her sho...

School for Sluts Ch. 01

by dannzguy on Sep 19, 2017
Fetish

This is my first attempt at writing erotica. If you are looking for serious hardcore sex, then chapter one isn't for you. However, as the story progresses, things will get more raunchy. Please comment so that I can improve my writing. ***** The look on Robs face said it all, he was obviously worried. His colleague saw it, and recognised that this concern h...

Jaime-Lynne's Anal Reaming

by Abeja on Sep 26, 2017
Anal

I was lying on my stomach recovering from a massive orgasm with Seamus' huge fat cock buried up my snatch. I could feel his cock pulsing and throbbing. I had just finished being driven through my second orgasm. The first one was almost simultaneous – I had started coming first and was writhing and screaming when Seamus, riding me hard, fired his load up my s...

The Basketball Team's Bitch Ch. 01

by HawaiianShirts on Sep 13, 2017
Anal

Isabel, the basketball team's trainer—though really just a second-year kinesiology student in charge of player injuries and rehab—tells me to strip naked. We're in the athletics doctor's office, which belongs to Isabel during the basketball season, and I'm standing in front of her in my street clothes, a school t-shirt and black skinny jeans over white jock...

Hadley's Other Cherry Ch. 02

by TotalKnockout on Sep 18, 2017
Anal

This is part two of a three part story. To read part one, go to https://www.literotica.com/s/hadleys-other-cherry-ch-01 To read the first installment of Hadley and Jack's story, Hadley's Cherry, go to https://www.literotica.com/s/hadleys-cherry *************************** Harvey Henderson was padding upstairs with a glass of water when he saw lights shi...

Butt Jewelry

by Xarth on Jul 15, 2020
Anal

Author's Note: This story takes place in one of those high schools where everyone is eighteen or older. You know the ones. **** Riley waited for Jen by the front of the school. She smiled when she saw her friend approaching and turned to fall into step beside her. "Morning," Riley said cheerfully. "Morning," Jen greeted her in return. "Anything interesti...

Young Guy Goes To College Ch. 04

by pantysubsissy on Sep 26, 2017
Transsexuals & Crossdressers

Sorry this chapter took so long to post... As I stepped outside for the first time dressed completely in girl's clothes I started to think how I ended up in this situation. Everything I was wearing belonged to my sister Robin but I was dressed up by my new girlfriend Julie, one of Robin's roommates and occasional fuckbuddy. I was wearing my sister Robin's s...

Slave Immigrant Ch. 30

by OldGuy1026 on Sep 14, 2017
Sci-Fi & Fantasy

After receiving a cloned body I was immigrated 127 Light Years from Earth to Free Skyes. Unfortunately I had to work and pay for that cloned body and I had very few skills a high tech society could use. So it was either I become an Unskilled Labourer or a Sex Slave. In the end I guess Human Recourses had figured me out correctly. All those years in BDSM chat...