Sissy Lingerie Stories

30,229 results
Orientation
Length
Source
Infinite Scroll

Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...

A Day Alone with My Inner Sissy

by Abitinsecure on Jan 21, 2020
Transgender & Crossdressers

It started off like any other of the rare days I have the house to myself. I woke up early at sunrise and slipped out of bed and headed for the shower to cleanse myself for the fun I was preparing myself for, something I always make sure to do as my mind starts flooding with my sissy fantasies and curiosity. I would consider myself a straight guy, work a la...

Neighbourhood Terror to Sissy Pt. 18

by Fibaro on Mar 10, 2020
Transgender & Crossdressers

Chapter 20 Marcy had a wonderful night's sleep while she didn't realise it, the only reason she had a quiet night was because Lisa had demanded it. What he also didn't realise was that while he was sleeping peacefully John was setting up a website, turning him into a real pornstar. Once it was online John hoped he would make a good amount of money off his s...

Being a Sissy for Viv Ch. 03

by Caron on Sep 25, 2017
Transsexuals & Crossdressers

I awoke slowly, enjoying the warmth and comfort of the bed and thick quilt. My mind was slowly trying to separate half remembered dreams from reality. Pink panties. A lacy bra. Viv's breasts. Excitement. Embarrassment. Suddenly my eyes were open as the catalogue of disjointed dream images slotted into the reality of the previous evening. Even as the memori...

A New Way Of Life

by blackdog27 on Sep 14, 2017
Transsexuals & Crossdressers

This story begins as many do. I stared to dress at an early age in my mom's things. Then I started to buy my own things as I got older; panties, bras and high heels. I was always small for my age taking after my mom, she was a small woman with a nice figure and so was I. I was only 5'4 and 110lb, blue eyes and jaw length blond hair. They loved me in high sch...

Bukakke Sissy/Angel

by hyperpress on Sep 14, 2017
Fetish

He's wearing his favorite outfit. A nylon/spandex blended thong that encased his fullness, shaved and smooth in a delightful caress. A bustier girdle with four straps (he wanted six but the cost was exponentially increased for those two extra straps), and wolford thigh high stockings, his legs and bottom were completely shaved...he was delighted with how fem...

Set Up Ch. 01

by Sissy_Ashlee on Sep 15, 2017
Transsexuals & Crossdressers

This is my first attempt into writing an erotica story. This tale will contain themes of female domination, crossdressing, and eventually MM sex. If any of this is not you thing, please scroll on. Otherwise, please let me know how I did. ***** Since I was a teenager, I had been bicurious. Not really interested in men, but what is between their legs. My obs...

The Ex That Kept Me Pt. 01

by sissythongluv on Sep 14, 2017
Transsexuals & Crossdressers

She knew I loved to wear panties. She didn't know who long I had been wearing them, but she knew I did, and she had no problem with it. My ex-girlfriend, Kate, who had cheated on my numerous times, always with bigger cocks (which wasn't very difficult considering my tiny size), wanted to meet me at the mall. We had broken up, and she was dating some guy sh...

Helping Jess Pt. 03

by mski on Sep 18, 2017
BDSM

Sometime in the morning I woke up with Jess on top of me giving me a good morning kiss. 'Wakey wakey sleepy head!' she said with a huge smile. I grinned back, it was a nice way to be woken and she looked as gorgeous as ever in her red silk chemise. I started to get aroused but my penis was always going to lose the fight against the chastity belt. I grimac...

Ian's New Job

by SatinSlip on Nov 26, 2018
Fetish

Authors note- this story includes non-consensual, rough, and coerced sex. As well as straight and bi-sexual sex. ************ Wendy moaned as her husband slowly licked around her pussy. She grabbed the sheets in her ecstasy. An orgasm rising excruciatingly slowly in her. Ian was great at cunnilingus. He practiced often on his wife. Delighting in the way...