Sissification Relapse Caption Story Stories

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Sissification 101: Ch. 01

by silkstockingslover on May 4, 2020
Fetish

Summary: Straight guy is caught watching sissy porn and...Note 1: Thanks to Eric who requested and helped plot this lengthy story. Note 2: Thanks to Tex Beethoven and Robert for editing. Note 3: All characters are at least 18 years old. Sissification 101: Ch. 01 1. MY SISSY CURIOSITY I've always liked nylons. I grew up when they were still popular and...

Sissification 101: Ch. 02

by silkstockingslover on May 18, 2020
Toys & Masturbation

Summary: Both Eric(a) and Joan discover the joys of toys. Thanks to the real Eric who requested and helped plot this lengthy story. Thanks to Tex Beethoven and Robert for editing this story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught in pantyhose wat...

Sissification 101: Ch. 05

by silkstockingslover on Aug 31, 2020
Interracial Love

Sissification 101 Ch 05 Summary: Erica practices taking BBC in both of her sissy holes. Thanks to Eric who requested and helped plot this lengthy story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught by a very supportive girlfriend in pantyho...

Sissification 101: Ch. 06

by silkstockingslover on Sep 28, 2020
Interracial Love

Sissification 101 Ch 06 Summary: Eric gets fucked by BBC for the first time; Joan gets black pussy. Thanks to Eric who requested and helped plot this lengthy story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught in pantyhose watching hypno-sissy porn by...

Soft Sissification

by Lying_Smitten on Feb 21, 2019
Fetish

Welcome to the softest sissy story around, but first you need to choose your character. Would you like to play as the Sissy themself, Mike, soon to be known as Mia, a 5'8 man with dark brown skin and black hair, with equally dark brown eyes, and a slightly soft build? Or would you like to play as the Sissy's sweetheart, Kate? A woman of the height of 5'6, wi...

My Sissification Ch. 03

by sissy171 on Aug 31, 2020
BDSM

Spring weather coaxed skimpy Summer attire. Melissa was 2" taller than me, so when we ventured out, I easily passed as female. I had learned all the subtleties and intricacies of face make-up, and my nails were always polished. I was "checked-out" by men everywhere. My legs and ass were muscular, shapely, and sexy; few women could compete from the waist dow...

My Sissification Ch. 02

by sissy171 on Aug 31, 2020
BDSM

I had always planned to go to college, but I was already fairly secure in my business, so I entered college with no scholastic trepidation. My way bigger fear was that I was still sporting a bikini tan, which kept me conflicted; fearful of being discovered, constantly on a sexual edge, and woefully missing Beth. The bikini bra outline was her "brand" upon...

The Sissification of a Hero

by Clutterspunk on Apr 22, 2025

Izuku Midoriya loved being a hero. He loved saving people with a smile and giving strength to the weak. He loved the feeling of doing something great and the happiness that followed from the people around him. Something he did not love however was paperwork. Sadly however, with great responsibility comes a great amount of paper-work. Especially if you're the...

Tricked into Sissification

by AnalOnlySissy on Aug 4, 2020
BDSM

Rene: How do I get her to go out with me? Brittani: You dont! Hahaha. She is way too pretty for you. Rene: I know. It's just I really like her. Isn't there anything I can do? Brittani: I can put in a good word for you, but you have to do something for me. Rene: Oh that would be so great. I'll do anything please. Brittani: Hahaha you are such a pathetic loser...

Forgotten Hero

by Lustful Majesty on Dec 31, 2020
Cheating Spouses

The world outside of this dungeon no longer exists to you. Your life out there has become foreign from the indeterminate number of weeks that you’ve been down here struggling to keep your wits. Deviant monsters who want nothing more than to abuse your prone body lurk down every hall, and there is a constant test of faithfulness to your wife who awaits your r...