Sissy Neighbor Stories

22,255 results
Orientation
Length
Source
Infinite Scroll

Sissy Maid Son Pt. 03

by Robyn228 on Oct 21, 2019
Transgender & Crossdressers

Note: This story is entirely a work of fiction, and should only be viewed as a fantasy. Any similarities to actual events or people are entirely coincidental. All characters are over 18. ***** Peter stood there looking at the black stilettos, with so many questions on his mind. He wondered why his brother would ever own stilettos, much less why their mothe...

Ultimate Sissy Weekend Ch. 05

by SissyTwinkleToes on Jan 21, 2020
Transgender & Crossdressers

Susie can feel her diaper getting warm as she fills it with more pansy pee. 24 hours ago, she posted an envelope containing five keys, and still has another 48 hours until they arrive at her house. Those keys are for the lock that keeps her in her dress, the handcuffs that keep her right hand locked to this sissy on her left, and the tiny pinching chastity c...

Brian Becomes Brittney Ch. 01

by BrittneyCummz528 on Sep 14, 2017
Transsexuals & Crossdressers

My name Is Brian or at least it was the first 18 years of my life. Brittney is my new name.... All of this started when I was just out of high school. It was the beginning of the summer and I was feeling great. During the summer I was planning to do a study abroad program for a year before college. The program was something my neighbor told me about. My n...

Brianna Finds a Father Figure

by Sissy_Sammi_ on Dec 31, 2017
Transsexuals & Crossdressers

Brian was an eighteen year old nobody with short blonde hair, pale white skin, and soft blue eyes. He stood at five feet eight inches and lived with his mother. He liked his old school, but when his mother got a transfer he was forced away from his home town. They moved into a small town in Colorado, into a small two bedroom home in a nice suburb. Brian was...

Caught In Lingerie

by hicutlover on Sep 26, 2017
Transsexuals & Crossdressers

I was driving home from work and all day I had been extremely horny. I had unbuttoned my pants and was stroking my cock in my purple nylon thong. I loved this thong. I could see the outline of my cock and the shape of my cock head in these panties. It was making me harder. All day I had been fantasizing about taking a cock in my boypussy and couldn't wait to...

Forced Femme

by Mrfriskay on Aug 11, 2018
BDSM

You've always been kind of a nancy boy. A little afraid of women, and awkward. The attraction has always been strong though, especially to dominant women. It was always obvious that you were a little different, but things changed when you met her. She wasn't typical in any sense of the word, and you find out the hard way.What's next? Annabel Lee, 6'1&q...

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My Neighbor Husband is a Jerk Pt. 04

by justme6996 on Dec 24, 2019
Fetish

The following story contains forced bi, face sitting, creampie eating and sissyfication, if those are not your things please find another story. And as always I love reading your comments and suggestions. ------------------------ The next morning I was surprised to receive a text message from her, "Wear your panties and bra and get up here now!, do not kn...

Older Man Watching Ch. 2

by Misieyes on Aug 30, 2017
Exhibitionist & Voyeur

Ken woke up the next morning at 5 A. M. and thought about what he saw the real estate sales man and Sissy doing. His cock started to swell. He wondered if she was up and maybe taking a shower. He grabbed his binoculars and looked through her open window. There she was asleep, naked and with nothing over her. How lovely she was laying there, her breasts so...

Caught In Lingerie Ch. 02

by hicutlover on Mar 5, 2018
Transsexuals & Crossdressers

As I awoke, I found myself on my side, with Tim's arm wrapped around me. He too was sleeping. I looked at the clock and figured I was out for 30 minutes or so. My bed sheet was covering the two of us and all I had on was my bra and thigh highs. Tim was still naked. My sissy clitty was hard; my horniness woke me up and I wanted more cock in my boypussy, right...

In a Neighborly Way Ch. 03 Act 01

by KristyT on Sep 16, 2017
Transsexuals & Crossdressers

(Summary: A couple sexually befriends a beautiful woman neighbor. In Chapter 1, they get together for the first time, as couple invites her over for an evening BBQ. Wife serendipitously sexually engages neighbor, and neighbor eventually seduces them both that evening. But, neighbor lady never takes her pants off the entire evening! Couple decides to each kee...