Sissy Lingerie Stories

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Pimped Out Sissy Bitch

by Gemsissy on Jan 12, 2018
Fetish

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit. I glanced at the phone....

My Sex Pets

by HornyKat on Sep 13, 2017
Group Sex

On the third try I managed to get the key into the hole and unlock my apartment door. Amazing what half-a-dozen Malibu and Diet Cokes will do to a girl's head. I stepped inside with my two new pets hot on my tight little tail. I had decided that one cock just wasn't going to be enough for me tonight, so I brought home two. Earlier, at the club, I named them...

Mark & Lisa Pt. 01: Key-holder

by LockedSissySubmissive on Sep 25, 2017
Fetish

When the doorbell rang I honestly thought I was hearing things, I'd lived in my apartment for two years and I don't think anybody had ever rang it before. It's not that I don't have any friends although if I'm being honest I don't have many, it's just that I live in a secure block and any visitors would ring the bell at ground level and then I would either c...

Sissy's First Time

by Sonjas_pet on May 23, 2018
First Time

By the time my wife, S, and I had been married for fifteen years, there was not much that we didn't know about each other. If you're going to make it that long, you're going to have to learn to be honest with each other. This is what had led to me recently, cautiously, come out to her as being bi, turning at once tepid physical relationship into one of ongoi...

Mistress Emma's Revenge

by sissymissyct on Oct 15, 2017
Fetish

Hi I'm Ken. Well I was, now I'm called Brenda. Here's a bit of my story for you. I hope you don't make the same mistakes I did. Because until I got caught misbehaving by my mistress, life was pretty good. At 38, I had a great job as an office manager in charge of 25 or so employees, mostly women, a really good salary, a nice office and plenty of job securit...

My sissy boss.

by mally01 on Apr 22, 2025

Craig was in his office at Lingerie International watching the wall clock his left drifting under his shirt stroking his soft hairless skin. He was waiting for five thirty knock-off time to come. His secretary Charlotte came in and asked if he needed anything else, and he gruffly replied that she could leave for the day. After he had witnessed Chantelle get...

Becoming a Sissy Slave

by pantysissyslave on Sep 11, 2017
Fetish

since I started dating my wife she has always known that I love to wear panties and other items of lingerie, she did not really like it but let me do it as long as she did not have to see me in it. When she was at work or out with friends I would rush to get dressed in the sexiest things I owned and would prance around the house and eventually masturbate i...

Sissy Boy Secretary Ch. 09

by Hotenuf4u on Sep 19, 2017
Fetish

Elaine had enlisted the help of her neighbor's daughter, Tammy, to help in obtaining a big business edge for her company, now it was Tammy requesting her help. Tammy's mother was divorced from her husband after an unfortunate chain of events, some of which were Tammy's fault. It seems that Tammy's father was quite a jealous man when it came to her Mother, he...

Sorry Sissy You Lose Pt. 04

by LittleDickSissy on Apr 10, 2019
Fetish

Slave had been busy. Spending hours looking online for things for his Mistress. His little dick always swelling and throbbing as he went through pages of web sites, looking at heels, lingerie, hose, dresses, jewelry, etc. Mistress had tasked her slave. He was to purchase various outfits for her to wear on an upcoming trip. A work trip for his Mistress, but h...

Cyber Sissy Ch. 02

by missvicky53 on Sep 25, 2017
Fetish

I waited, watching the door as the sound of Megan's heels came closer and closer. I noticed a distinct stirring in my white lacy panties as the anticipation grew. I couldn't help it, I was about to live one of the fantasies I had spent so much time reading about on the net. Besides, since following the list of instructions Megan had left, I was in no positio...