Sissy Neighbor Stories

22,255 results
Orientation
Length
Source
Infinite Scroll

Sarah's Sister-in-law

by SarahCD on Jun 11, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** I first published this experience a few years ago. I prefer to call them 'experiences' since the term 'story' implies fiction to me. My experiences are based upon my real life. Since I started posting my experiences my writing skills have improved a little. While, I cannot change...

Neighborly Relations Pt. 04

by grizzley123 on Mar 25, 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...

Wife Cheating with the Neighbor Ch. 02

by mm32217 on Nov 20, 2018
Erotic Couplings

In the previous chapter, my lovely, sexy wife had, after a few drinks, confessed to the affair with Steven, our neighbor. I would have flipped out at her confessions had it not been for the fact that I had been aware of the tryst for a while and over time, started accepting it. The relationship with my wife, Maureen had continued to be good and I felt that w...

Sissy Awakening Ch. 03

by Torbjornson on Oct 19, 2020
Transgender & Crossdressers

- Sissy Meets Sarah's Bull - Standing at the living room window with the windex and paper towels, I teetered on the ridiculously tall Mary Janes. It were as though I were standing on the balls of my feet and toes only. There was no relief. My other pumps felt like heaven compared to these! She said to wash inside and out, and not to miss a spot. That meant...

My Metaphor

by hyperpress on Dec 24, 2018
Fetish

The audience drops into a continuing story written in first person POV (mostly). The following based on a true story. Given enough time, any question that occurs to the reader shall be answered, eventually. * I woke the next day, showered, put on a comfortable chemise, a microfiber and nylon blend thong and open toed sandals, made some coffee and sat down...

Jackie Meets Her Sister

by Sissy_Sammi_ on Mar 7, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** *All characters are 18+ So this is the 3rd part to this story, and yes it's been a bit of a break since I wrote the last one. Where the story has gone so far has made some people upset, but personally I think I like it the way it is. Though I am open to making an alternative vers...

Kasey's Confession Ch. 02

by KaseyLegs on Sep 14, 2017
Transsexuals & Crossdressers

After Mike left, I stood in front of my big mirror and stared at myself. I kept thinking of all the excuses I had given myself, and other people, about why I shaved my legs and liked wearing short shorts, skirts, high heels and stockings. All that had changed in a single afternoon, although the writing had been on the wall for a long time. Even before I had...

A Freshman's Summer Class Ch. 07

by CapnSteelBoy on Jun 1, 2020
Transgender & Crossdressers

A Freshman's Summer Class **All characters are of legal age for adult content.** We Continue from where we left off with our brave hero, as his adventure continues during his summer of higher education learning! This is a continuing series I'll be releasing as my busy editor(s) help me clean up my keystrokes of mess.. Much thanks goes out to them, as th...

Transforming Brent Pt. 03

by sissymissyct on Oct 8, 2019
Fetish

Over the next few days I removed most of my male clothing from the house and donated it to Goodwill. I met Wendy as she got out of work each day and we went shopping. The first time was for regular clothing. Skirts, dresses and blouses, leggings and shoes and regular lady's sportswear. Thursday it was lingerie night. I ended up with multiple bras and camiso...

The Perfect Age Ch. 07

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

It wasn't long after I became his lover that he had me seeing other men. The first time was at a party he took me to several months after I started seeing him. He had me go down on a friend of his while he watched. Assured me all was okay, it would be 'safe'. 'Just do it, you'll do that for me, baby, right?'...I did. I actually enjoyed it. I found out early...