Sissy Butt Plug Stories

100,438 results
Orientation
Length
Source
Infinite Scroll

Hanging Around

by anotherSDguy on Sep 17, 2017
BDSM

*Disclaimer: Since this is a fantasy, I'm going to ignore certain inconvenient things (like condoms) that are a requirement in real life. Seeing as this is a fantasy, I feel totally justified in doing that. Also, the house setting described in here is based on a place I used to live a few years ago.* It's your first time meeting me, and you're coming over...

The Perfect Day

by thesubgauge on Aug 18, 2017
Fetish

After waking up to perfect sunshine rays coming through the plantation shutters, my first thoughts were of the days monumental event. Today was going to be the day I met Goddess Alia in person. The water in the shower felt warmer, the breakfast tasted better and my clothes felt smoother. Nothing could go wrong. As I drove over to meet her at her hotel, I di...

Lunch Break

by celticlass on Aug 31, 2017
Erotic Couplings

This story is dedicated to one of my best friends, Jim. Thank you for some wonderful lunch hours, both now and to come. ~~~~~~~~~~~~~~~ We've been friends for ages. Well, it's seemed like ages, when in reality, it hasn't been but about two-and-a-half years. Weekly lunches, chats, emails, phone calls... Celebrating good times. Mourning over bad. Venting abo...

Broken Seals Ch. 05

by Classicist1789 on Jun 9, 2020
Toys & Masturbation

While gaining some much-wanted sexual experience from Matt and Ro, my relationship also resulted in a flood of new confidence. I felt connected to myself and my body; I wanted to wear clothes that showed off more of it and became more outgoing, slowly but surely learning that almost no one (certainly no man, even a gay one) was going to be miffed at a busty,...

A Christmas (Bondage) Story

by Ropesonme on Oct 6, 2020
BDSM

It's not every day you walk in the door to find an elf in your living room – especially a female elf. Slightly under five feet, she was taller than I expected. She had long blonde hair braided down her back, so that it was easy to see her slightly raised ear lobes that were not as tall as I expected. Her brilliant blue eyes were slightly larger than I expec...

Susan and John's Return Ch. 04

by dan57 on Sep 17, 2017
Erotic Couplings

John begins to enjoy his humiliation By Dan57 with characters from Jill York * When they returned home on the next Sunday evening, Susan immediately arranged for her husband John to move to his new bedroom. A cot and a cupboard would be his only furniture until the craftsmen had finished their job. John would have to live for a few days in the former lau...

For Marion's Pleasure Ch. 02

by MarionsPuppy on Nov 23, 2017
Fetish

"Babydoll, I really want to discuss something with you, something very important to you, to me, to us, and by us I mean me and my lover and our fabulous developing relationship, yes? And don't get too upset by that definition of "us" baby, because you and I are no longer an item are we? You stopped being my husband when I found that pic of a white hubby wi...

French Lessons

by lipsticked on Sep 13, 2017
Fetish

I first saw the ad on the internet. The website was a listing of Dominant Women on the West Coast. Since I live in Los Angeles, I was checking out the pictures and information on local dominants. The one that caught my attention was unique. Madame Darcy was based in Paris. Her ad stated that she traveled to Los Angeles frequently and had family here. She re...

Kasey's Confession Ch. 01

by KaseyLegs on Sep 14, 2017
Transsexuals & Crossdressers

My name is Kasey. This is the true story of my journey into a life of dressing as a woman, role-playing with men and eventually spending over a decade being sexually submissive to men and being passed around freely between them. My journey began nearly twenty years ago and started at a different place than most crossdressers. I was obsessed with women's leg...

Sparrows Caught and Caged

by nikisixx on Oct 6, 2020
Fetish

NOTE: This is a work of original fiction. All names, circumstances, or situations herein are purely fictional. They are not based upon either real people, governments, organizations, places, or real events. Should any parallels to real circumstances be drawn, historical or otherwise, they are purely coincidental. --------------------------------------------...