Sissy Neighbor Stories

22,255 results
Orientation
Length
Source
Infinite Scroll

Old Man Watching Ch. 3

by Misieyes on Sep 16, 2017
Reviews & Essays

Ken called Larry and said he had a surprise for him and told him to come over about 11 P.M. Larry wanted to know what the surprise was but all Ken would tell him was he would see when he got there. Larry said OK and that he would bring over some beer. Ken knew Larry would be more horny then ever after a few beers. He always bragged how hard he could still ge...

Powerless

by siscuc on Sep 16, 2017
Transsexuals & Crossdressers

I was alone in the house, Tina was at work. It was 4 in the afternoon and i was looking over some pictures when the phone rang. It was Tina, "Hi Sweetheart" i said. The tone of her voice was harsh "Start getting ready, tonight you will be my sissy, you can choose to wear any of my clothes except the ones in the top drawer, I'll be wearing them." That was all...

Sara's Amazing Night

by Sexy_SaraCD on Sep 16, 2017
Transsexuals & Crossdressers

I felt his entire weight, his entire body push me against the wall and the more I struggled the harder he pushed into me. My hands are firmly planted on the wall and my eyes are closed. At this moment, I feel panic. Panic of what may come soon. His leg, strong and thick, push my legs apart but my tight skirt stops them. He doesn't let that prevent him from...

A Natural Sissy Ch. 08

by harv069 on Sep 15, 2017
Transsexuals & Crossdressers

Author's note: This is a multi-part story about a young woman turning an older man into a compliant, sissified plaything. It is best understood if you read from the beginning. If that idea doesn't appeal to you, don't read the story. If you don't like this kind of story, but read it anyway, please don't bomb me. I warned you to go away. If you like the idea,...

Cumming of Age

by Ewriter111 on Jul 3, 2018
Interracial Love

At the end of my senior year of high school, I had just turned 18 and was looking to have some fun with all the upcoming parties. I had just quit my part time job after I paid off my car and had plenty of time to spare. Because I was young looking, it was not until my senior year that I got invited to parties. Even now I was told that I looked only 15 or 16....

Neighborly Relations Pt. 03

by grizzley123 on Feb 11, 2019
Fetish

Author's Note: As is true with all of my stories, this is a fantasy. The themes and ideas I find erotic might be different than yours, that's ok. Please leave comments, my ego will appreciate the positive ones, the writer in me will enjoy the constructive ones, and the submissive side of me will accept the berating ones. Enjoy! *********** It is best to re...

My Neighbor is My Daddy Pt. 01

by sissyrulez on Jun 9, 2020
Fetish

As my girlfriend left for work today, it had now been six months since the last time we had sex. I was so horny all the time I found myself masturbating just about every time she was out of the house. This morning was no different. There I was on the bed jerking off into a pair of her panties, when all of a sudden there was a knock at the door. I was so star...

Mrs C

by pantywriter on Sep 11, 2017
Mature

This is a lengthy story covering many different subjects. Be warned that some fetish concepts are explored. ***** When Mr. Caruso next door unexpectedly passed away, I attended the funeral along with my parents. I think that the entire neighborhood turned out. The Carusos were popular, friendly people and his sudden passing shook everyone. It happened in...

Mother Dear Pt. 01

by keptsissy on Sep 13, 2017
Fetish

"Let's say for instance that I had son that was a sissy boy. A son that not only was a sissy boy that did very dirty and naughty things while he still lived in my house, dirty things for our next door neighbor, but a naughty little boy that liked to dress up in his mother's underpants too. I think a boy like that would need guidance. Don't you? I remember wh...

Living Next Door to a Closet Sissy

by tarkustrooper on Sep 15, 2017
Text With Audio

I had waaaaay too much fun making this audio because this happens to be one of my favorite kinks ever. Be warned, though: this audio has a bit of a slow build here, and there could've been a time or two (or more) that I've gotten carried away here. So it seems that I have a peeping Tom neighbor that wants me to dress him up and fuck him like a girl? Well, t...