Sissy Neighbor Stories

22,255 results
Orientation
Length
Source
Infinite Scroll

The Tables Turned Pt. 02

by 9volt on Oct 15, 2018
Fetish

The party was wrapping up and Brandi invited Mike and Erica back to our house for a nightcap. The nightcap turned out to be tequila shots. She was singing "tequila makes her clothes fall off," and winking at me. Brandi suggested a game. I think it was called "Porn the game", and I was surprised at how eager Brandi and Erica were to play. Mike and I were the...

Caught Off Guard

by Alemuchomas on Sep 15, 2017
Transsexuals & Crossdressers

I was walking home with some friends when a long old white car passed by very slowly next to us and hinted at me to get close. When I realized he was hinting at me I got close to the car window while my friends just kept on walking. He was an older gentleman with white hair and fairly built body from just at a glance. He directly told me, "I saw you, I thi...

Sissy Slut Ch. 01

by Scribler on Sep 13, 2017
Transsexuals & Crossdressers

It had been quite some time since I had stopped in the club. Not that I didn't crave the pain I could infect on one of the sweet young things that came to the club. I craved it more now then I ever did a few years ago. But due to relocation of my job I had to leave the city and I couldn't find a club that catered to my needs. Now I was back and I was chompin...

Cross Dressing: A Hypothesis

by Da_Vida on Sep 16, 2017
Reviews & Essays

First as a young adult and then as a psychologist, I read extensively in an attempt to find an explanation for my cross dressing behavior. Several psychological hypotheses have been proposed in the literature but I did not find any of them to be compelling. While I don't think it is an explanation for cross-dressing, one hypothesis that resonated somewhat...

Winter Treat

by skriblur on Feb 6, 2018
Fetish

We're having a real cold snap. O.K., maybe up north nobody'd call it COLD, but for us down here it's about as cold as it gets. And we completely freak out about it too; stocking up on supplies as if a hurricane's coming, battening down hatches, taking plants off the balcony, running faucets on trickle overnight. Schools close, people leave work early. Nobod...

My Cuckold Story

by ohsubmale on Jul 15, 2020
Fetish

The story below is how I became a cuckold for the first time and probably for life. My wife and I had been married about 10 years and have been through as many Christmases. We have no kids, live in a nice home, both work, and in general have a great life. We slept together non-stop and were open and kinky; willing to try just about everything there was to...

Jesse's Journey Down a Rabbit Hole Ch. 08

by Rebeccasm on Sep 25, 2017
Illustrated

As I mentioned in the previous chapters, this story is a collaborative effort between me and Rebeccsm. She has provided the art, and a lot of the plot, god I love how her mind works, and me for the text. Please let us know how you feel about our efforts. Comments and votes are welcome. It is the only way we will know if you like our work. I would like to th...

Nikki Goes to College

by Latexsissy69 on Sep 25, 2017
Transsexuals & Crossdressers

When I was younger I used to be a complete bully. I used to make fun of the poor people that couldn't afford to buy new clothes every school year. There were also times that I would make fun of girls that didn't want to participate in gym class because they were wearing a dress. I used to agitate so many people that I would get into fights almost daily. One...

Jesse's Journey Down a Rabbit Hole Ch. 10

by Rebeccasm on Sep 19, 2017
Illustrated

As I mentioned in the previous chapters, this story is a collaborative effort between me and Rebeccasm. She has provided the art, and a lot of the plot, god I love how her mind works, and me for the text. Please let us know how you feel about our efforts. Comments and votes are welcome. It is the only way we will know if you like our work. I would like to t...

Roommate Dress-Up

by silkstockingslover on Oct 26, 2020
Transgender & Crossdressers

Summary: Straight guy is feminized by female beauty. Note 1: This story is dedicated to the real Mike who requested this story. Note 2: This is a 2020 Halloween Contest Story so please vote. Note 3: Thanks to Tex Beethoven and Robert for editing this story. Roommate Dress-Up "Shit," I sighed, as I saw my outfit for the wedding... I should have guessed s...