Sissy Bikini Stories

40,840 results
Orientation
Length
Source
Infinite Scroll

Start of the Summer Ch. 03

by emelle78 on Sep 18, 2017
Transsexuals & Crossdressers

Part Time Helper Those first two days with the Walkers that I told you about in Part 2 were incredible. When they came home early and caught me wearing Mrs. Walker's lingerie and jerking off on their bed it changed my life. Mrs. Walker dressed me up in frilly, girly clothes, did my makeup, and then I had sex with both of them in every way imaginable. After...

Master's Degree in Crossdressing Ch. 02

by wifetoy on Sep 16, 2017
Transsexuals & Crossdressers

This confession is the second chapter of a follow up series to my earlier series "College Crossdressing Confessions." My wife forced me to make those confessions detailing my shameful addiction to wearing panties, pantyhose, and other girly intimates, and my panty pilfering ways in college. While I was making those confessions to the public for the first tim...

My Girlfriend's Sister is Nasty Too

by Dr_AWES0ME on Oct 6, 2020
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** Believe it or not this is actually based on a true story. The majority of this story is 100% true, some elements were slightly embellished, some were part of a vivid dream, and some parts (names for example) were completely fabricated. Although I have written for many years and ho...

Payson's Wedding Ch. 02

by fantaseeboy on Jul 16, 2019
Transgender & Crossdressers

The next morning, Becky and I walked into the jewelry store a few minutes after it had opened. The older man who owned the store looked at us with a funny expression on his face. We approached him hand-in-hand. Becky, with her Hispanic heritage, was wearing jeans, a white blouse that draped over her giant breasts in the most alluring manner, and white cross...

My Weekend Surprise Ch. 01

by pinkpanteez247 on Sep 19, 2017
Transsexuals & Crossdressers

This story is another fantasy of mine, of which I have many. My wife knows about my panty wearing and is OK with it but that's as far as she'll let me go, so I cross-dress when I get some alone time. I try to get into as much detail without making it a book to read. I like to read short stories that get to the point. I hope you have as much pleasure reading,...

Halloween Pool Party Pt. 04

by sissymissyct on Sep 14, 2017
Fetish

Monday morning I was awakened early by Miss Annie releasing the air from my plug and swiftly pulling it from my bottom. I cried out from being so crudely awakened from my slumber and that got me a quick but hard smack on my already bruised bottom. "Good morning Brenda, time to shower and get ready for a big day", she informed me. "Thank you Mistress" I answ...

A Friend Catches Me

by PinkPanties4me on Sep 16, 2017
Transsexuals & Crossdressers

Karen was all dressed for work. As she was heading out the door, she kissed me goodbye. "What do you have planned for today?" She asked. "I don't know a little of this and that," I said. Little did I know this day was going to be more exciting than that! I put on my mint green camisole and of course matching panties and went to work on cleaning the h...

Transforming Brent Pt. 05

by sissymissyct on Dec 2, 2019
Fetish

I awoke early, partially due to the pressure of morning wood in the chastity. Once I settled down, I showered and slipped on a robe and quietly made my way to the kitchen. I quickly familiarized myself with the layout and, finding what I needed, started cooking a nice breakfast for my mistresses and myself. Ham and cheese omelet, OJ, toast and sausage, along...

Sissy

by rogue01 on Sep 19, 2017
Fetish

Sissy It happened at last that he was caught. His wife came home mid-afternoon with her friend Miriam and found him upstairs in the bedroom wearing a pair of her panties. Her reaction shocked him. In the hot instant of his overriding shame he was aghast to discover in her a persona he had not yet known existed. Him, a faintly domineering man, like so many...

Smoking Blues

by sissymissyct on Mar 26, 2019
BDSM

"Hey Bren," called my assistant Sarah. The home office called while you were out smoking. You Better call Mr. C back. He didn't sound happy!" "Okay, thanks dear. I will call him back straight away," I replied as I headed to my office. As I was opening my door Sarah continued. "You know, you really have been taking a lot of smoke breaks lately. We are all co...