Sissy Lingerie Stories

30,229 results
Orientation
Length
Source
Infinite Scroll

The Office Ch. 04

by EasilyConfused on Jan 23, 2018
Transsexuals & Crossdressers

There were six screens in total, one for each of those being monitored. Their heart rate, blood pressure and neural receptors all key indicators. The technician made gentle adjustments to the controls in response to certain measurements that she noticed on each of the screens before her. Behind her a woman in a business suit watched on. Paula Hamilton was sk...

Neighbourhood Terror to Sissy Pt. 09

by Fibaro on May 27, 2019
Transgender & Crossdressers

While Mark was going through his night time ritual and sleeping Lisa was at CC's getting licked to orgasm after orgasm by Stephanie. The more she learned about sissies the more she knew it was what she had always wanted. She had never been with a such a pretty girly girl like Stephanie, and definitely never with anyone who was that good with a tongue. The th...

Discovering Mistress Sarah's World Pt. 03

by oneguy4fun on Sep 12, 2017
BDSM

Chapter 7: A Brief Digression Mistress Sarah sat naked, in a stiff padded chair in front of a large vanity. She waited patiently for her two sex pets to return. It was time for Joe to learn how to properly dress her for a night out and she wanted him in full sissy attire for the event. May had been charged with the task of getting him back into his dress....

Home Alone: Day 02

by sissy_boy_stu on Sep 16, 2017
Transsexuals & Crossdressers

Day 02, The Mistress It was 12 o'clock in the office, I couldn't wait 5 whole hours before I got home so I decided to take the rest of the week off. After racing home I ripped my clothes off and dived straight into my sisters panty drawer and took out a pink matching g-string and bra with hearts on. The feeling of them on sent my cock rock hard so that it s...

Caught in the Toilet

by Dennis_St_John on Sep 14, 2017
Transsexuals & Crossdressers

Kneeling on the floor beside the toilet, dressed in lingerie and wearing pink lipstick waiting for the door to open, my mind kept going around in circles to what led me here, wondering if I could have done anything different to prevent it. I remembered sitting on the toilet earlier today looking at my bright pink nylon and white lace panties, resisting the...

Exposed as a Sissy Cuckold

by lapitup65 on Sep 18, 2017
Loving Wives

Last Friday we had a date scheduled. We were going out to dinner to meet Jay and we had a room booked at a nice hotel. Mandy and I checked in early. We relaxed for a while, sipping a glass of wine before Mandy headed off to take a bath and start getting ready. Just as Mandy settled into the tub, Jay sent her a text. I didn't read the text, I just took her ph...

Katelyn's New Sissy Pt. 01

by bluesbirds on Dec 25, 2018
Transgender & Crossdressers

I remember she made me try the Sissy Peni-Pacifier in the store. It was a humiliating day outing, meant as "my" Christmas gift. Dressed up in a tiny bright red sexy elf costume with marabou trim around the edges that ended at my sissy clit, black fishnet stockings and 4" black heels, with a ridiculously large shiny red bow in my hair, surrounded by mirrors a...

Man Disciplines Sissy Ch. 01

by LanaBehave on Sep 14, 2017
Transsexuals & Crossdressers

I enjoy nice undies, sexy undies, soft and pretty lingerie, and delicate and dainty clothes whenever possible. I put on these things, and feel feminine and aroused, eroticized....the pretty dress, the wig, the nylons, panties and bra, heels... I also feel the misbehavior aspect. A boy/male like me, even if it looks sexy or feminine on me...dressing girly is...

FMDM Inc - Jerry's Story

by satinmarabana on Sep 13, 2017
Transsexuals & Crossdressers

"I just want him to get what he needs without destroying my family or our marriage," said Mrs. Farrett quietly. She was sitting in a corporate office speaking to Amber Giles, a woman half her age and twice her breast size. Approaching this mysterious FMDM, Inc. had been her last resort to saving her marriage. "I understand, Mrs. Farrett," said the FMDM repr...

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...

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