Sissification 101 Stories

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Infinite Scroll

Wishes for my Wife

by Sinburn on May 17, 2019
Erotic Couplings

Tom sat on the park bench and watched his wife queuing at the ice cream stall. They were both hitting 40 this year and he couldn't help ruminate on the nature of his relationship as they planted their feet firmly in middle age. He loved her, no doubt about that but did he desire her? Yes and no. They still had sex and whilst infrequent it was always good and...

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Runt of the Litter

by grimbous on Oct 9, 2017
Transsexual

(This story involves a lot of humiliation of the main character, futa on male action, incest, and other fringe fetishes. If these aren't your thing turn back now. I also wanted to give credit and thanks to the artist Mafen for the above picture which helped inspire this story.) The hall is quiet. You were pretty sure nobody was at home. You creep carefully d...

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Everything Has a Price Ch. 06

by MALIBUMAN666 on Sep 14, 2017
BDSM

Author's note: This story doesn't seem to be as popular as some of my others, I don't know why that is particularly... it's a lot more 'real', certainly more 'real' than 'Owned!' or 'Out of Your Hands' which are both quite far-fetched really... It doesn't bother me particularly I'm just interested to know people's opinion and so I really do welcome your feed...

A Picture Perfect Sissy

by meeah sue on Sep 16, 2017
Transsexuals & Crossdressers

"Holly, hold your breasts up. That's it honey. Squeeze the nipples between your fingers. Make them hard for me, sweetie." Jason lifted and pushed his soft breasts together, squeezed the small dark nipples, and hurriedly looked up to see if what he was doing was okay. He really wanted what he was doing to be okay. It was dreadfully important to be okay. Kare...

Journey into Feminization Ch. 01

by KneelingNancy on Jul 14, 2020
BDSM

***Chapter 01 - The Beginning Like so many of our beginnings, mine started to what some would call a normal life. I grew up in on the west coast and would consider my family upper class. Both my parents had successful careers and my brother and I had a lot of great experiences growing up (private sports clubs, investment in the arts, etc.). During my chil...

KINK 101

by qros on Mar 17, 2020
Fetish

The structure of this story will be a bit eclectic. The KINK department offers several classes, each addressing a different topic, and I'm planning to write up ~1 semester of each class. If you want a specific kink, you can skip to the class for that kink. If you want a narrative structure, you can follow the classes sequentially. There will be reoccurring s...

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Radio Radio

by TexRiffraff on Sep 12, 2017
Exhibitionist & Voyeur

Out of town seminar leads to an unexpected opportunity Author's notes: This is a work of fiction. In this fantasy, nobody is worried about STDs. In real life, all non-monogamous sex should be practiced using accepted safe-sex precautions. All persons involved in sexual activity are at least 18 years old. : : : : : Where'd everybody go? One minute, I wa...

Human Sexuality 101 Ch. 02 Pt. 1

by GirlofDirection on Sep 13, 2017
Group Sex

Trevor hungrily watched the students begin to file in with Nikki and Edward in the front of the room laying down on the bed kissing passionately ignoring everyone as they came into the room. Student after student looked towards the bed with curiosity and surprise as Trevor smiled at them and asked them to take a seat in the auditorium. Other students came in...

101 Ways to "Repel" Dicks

by kin1041 on Jul 8, 2018
Erotic Couplings

101 Ways to "Repel" Dicks, apparently a collect of stories about women dealing with sexist, douche-baggy men. Seems like an interesting read, if the contents may be a little... dirty. (This basically going to act as a hub for a recent idea I wanted to pursue on CHYOA but couldn't find much on the topic. This story will be a collection of misadventu...

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Naruto: What's it like to be in Konoha High?

by Ultimatesextool on Feb 19, 2010
Fan Fiction

Your name is John Doe. You are now eighteen years old and a senior attending the high school known as Konoha Jounin High (Konoha's middle school is called Konoha Chuunin Middle School and elementary being Konoha Genin Elementary school and so on) and this just so happens to be your graduating year. You pretty much are living a great life as a teen. You are a...

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