High School Sissy Stories

209,604 results
Orientation
Length
Source
Infinite Scroll

The Streak

by Tara_Neale on Aug 19, 2017
Exhibitionist & Voyeur

I have been overweight for most of my life. I was teased, more like tormented, in elementary school for it. My parents did their best. My mom was at the school at least once a week trying to handle the situation and I really appreciate it, but it did not work. The more they protested, the worse the bullying got. Junior High was better because I was not the f...

Black Men are Gods Ch. 20

by Samuelx on Sep 12, 2017
Non-Erotic

My name is Byron Langston. A six-foot-one, lean and muscular Black man of Haitian and Native American descent living in the city of Brockton, Massachusetts. I recently graduated from the University of Massachusetts ( Boston campus ) with a bachelor's degree in business administration. Presently, I work for United Credit Union, a local business. It's okay, I...

Twins

by chas4455 on Mar 17, 2020
Non-Erotic

Catherine (Kizzy) and Carolyn (Kissy) are twins. Catherine came into the world first, at 3:15 am. Her sister Carolyn followed 8 minutes later. Kim Soo Park cried. She had 2 children already that she could not afford to feed. How would she ever be able to care for 2 more babies, born premature and facing severe medical expenses growing up? --- "Ladies and g...

The Neighbor Girl

by ainu2 on Sep 12, 2017
Mature

My wife and I met in high school and just clicked right from the start. I guess we were right because we were married for 38 years. We never had children. It wasn't for not trying, I can't imagine any two people being much more active sexually. At first we were happy to be "lucky". Later, by the time we started checking and discovered I was the problem, we j...

College Tutor

by passionatepdx00 on Feb 12, 2019
First Time

I always excelled in school, I watched others struggle just to make it to graduation but for me it was never difficult. In high school I was involved in a lot of extra circular activities such as student government, national honor society, and soccer. I graduated with a 4.0 GPA and got into a great private university, choosing to double major in Finance and...

The Homecoming

by captivate on Sep 13, 2017
Erotic Couplings

She never should have promised to come to this stupid game. Emma was not a person who honored tradition, so why was she here? She knew the answer. She had come to see her niece play Powder Puff football. It was the first event in a very jam-packed homecoming week, and Julia had begged Emma to come. Just driving into the stadium parking lot brought back horri...

Just a Bit of Red

by RedHairedandFriendly on Sep 16, 2017
Reviews & Essays

Many regular posters on Literotica's Bulletin Board know a lot about me, probably more than they should, seeing as 99.9% of the folks there I've never met and they say telling too much online is unsafe and that is probably true. One day it will most likely come back and bite me in the ass, but I'll cross that bridge when it is finished being built. This es...

EPOCH: The Story of Rockstars Ch. 02

by vechron on Sep 1, 2017
Erotic Couplings

2009. Cannes, France. Nikki and I are sitting in the sand below the break wall, the traffic behind us a low din. It's six o'clock at night and the sky is an orange hue, the sun still dipping below the horizon. "What ya thinkin' about sexy?" I look over at her and she looks back at me grinning, crossing her legs sexily. She's my wife; just over five feet...

From Syria With Love

by Samuelx on Sep 16, 2017
Interracial Love

As Salam Alaikum, dear reader. I thank the Most High for bringing you here. I have something important to share with you. The lives of Muslim women fascinate folks from the outside world, especially in the West. As the eldest daughter of a Libyan immigrant family, I have a complicated life, to say the least. My name is Salwa Zeidan-Harrison, and I am a young...

Sadistic Startup

by edrider73 on Oct 12, 2017
BDSM

For tremendous help with editing and improving this story, grateful thanks to author/editor hentaikitten, whose specialty is luscious, sensually saturated interracial matings -- not couples of different skin color but of different species, such as a male demon with a human virgin and an elf with an orc. "Don't you have an ounce of self-respect?" Frankie scr...