Cuck And Stockings And Heels Stories

359,800 results
Orientation
Length
Source
Infinite Scroll

Sissy Awakening Ch. 01

by Torbjornson on Oct 5, 2020
Transgender & Crossdressers

"Hey baby, when are you coming home?" the text message buzzed quietly. Pulling the phone discreetly from my pocket, I type out, "Same time as usual, just after 5, why... what's up?" It's my lover Sarah, my best friend, and woman I'd known for over 10 years. We were dating and quite a serious item within months of meeting. Everything just seemed to click wi...

All the Bells and Whistles Pt. 03

by luciddream81 on Jun 11, 2019
BDSM

Author's note:This is my first story and a relatively long one (60,000 words total), which probably isn't a good thing. I originally started posting chapter-by-chapter but realized it hurt the flow, so I've reduced it to approximately 8 "parts" or so. The "action" pics up in parts 4 and beyond, so if you're impatient feel free to jump ahead. But if the story...

Kendra's Way Pt. 05

by Bullwip on Sep 16, 2017
Interracial Love

Kendra and Amber sat across from each other at the kitchen table in the in the breakfast nook just off the kitchen. They were discussing the subtleties of manipulating men, in Amber's case, her boyfriend Jeremy into being more attentive and submissive to their women. "I can't stress enough Amber," said Kendra now looking out the large window into the evenin...

The Whore's Whore

by Couture on Sep 25, 2017
BDSM

"You know what we are?" asked Alexis, taking a drag on her cigarette and leaving red lipstick on the filter. "We're high class whores. That's all we are." "I don't think so," remarked Michelle. She hated these little meetings with the chairman's wife. Hated this conversation. She wanted to disagree, yet she didn't very well want to say anything that would o...

Rags to Reunions

by KennyWright on Sep 12, 2017
Romance

Author's note: This story is hard to categorize. Without giving away too much, it contains straight sex, group sex, voyeurism, a little bit of self-pleasure, a little bit of exhibition, humor, grudges, nostalgia, longtime crushes, memory lanes, and ten years of pent-up attraction between a boy-turned-man and our female protagonist. More than anything, though...

Jacki's Journey into Sissyhood

by jacki697 on Sep 18, 2017
Transsexuals & Crossdressers

I thought to myself could I really go through with it this time? I had to at least try it, didn't I? I took another swig of wine and then brushed the blonde strands of hair out of my face again as and I read through the message one more time. "Jacki, Id love to get together and treat you like the beautiful gurl that you are. Look over my pics and if you like...

Panty Boy Ch. 08

by vieuxbleu202 on Sep 12, 2017
Transsexuals & Crossdressers

I had to go out of town for a meeting; my ass was very sore from the night before. Those girls had really given it to me; my asshole was left a gaping hole. I could feel the "lips" of my asshole for over an hour last night, all big and puffy and open waiting for more. I felt like a total whore and I loved it. I took three huge cocks and was left begging for...

Chaste (A One Week Chronicles Story)

by Louise69 on Sep 16, 2017
Transsexuals & Crossdressers

This is probably the darkest of the One Week Chronicles story - Part 2 certainly is! - but I enjoy trying to find new ways to write and explore characters. I'll be very interested to know your thoughts on this one as it's probably the furthest from me, but was still huge fun to explore. As ever, it slots perfectly into the timeline and happens before the v...

My Job as a Tester Ch. 07

by dreamer_of_urges on Sep 14, 2020
Fetish

I walk over and look through the window into the training room. I see that Debbie has finished her session and now Sarah has Carol nursing on her. I turn up the volume so I can hear what Sarah is saying to her. "My little girl is wet. She needs to have her diaper changed, why didn't Momma Debbie do it before she left? Or maybe my little girl likes a wet dia...

Mature Prudish Woman Blackmailed Ch. 02

by fannyrat on Sep 14, 2017
Fetish

This story is part 2 of Mature Prudish Woman Blackmailed. It is advised that you read part one first. All comments welcomed. ***** Two years had passed since I had married and become pregnant by my young lover. In that time I had been incredibly fortunate to conceive and carry another perfectly normal child, before my periods had stopped altogether and I...