Crossdressing Neighbour Stories

5,093 results
Orientation
Length
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Infinite Scroll

Neighbor to Lover Pt. 01

by sarahchica96 on Oct 2, 2018
Transsexuals & Crossdressers

Introduction It was the summer I (Alex) and my twin sister Gina graduated from Business school, ironically Gina and I joined our family real estate business. This was a way of our parents keeping us busy and stop our procrastination about searching for jobs elsewhere. It was also the time my crossdressing persona met our neighbour Mr Parker. Backstory......

TV Beginnings - Caught by Neighbour

by Nylontease on Sep 16, 2017
Transsexuals & Crossdressers

I started crossdressing at quite an early age, 'borrowing' items of my mum's underwear and furtively dressing in them when she was at work. As I was an only child, and mum and dad had separated, I had quite a lot of time to indulge my little hobby! I used to love wearing her tights, the sexy feel of them encasing my legs and cock, and the way they made me fe...

Stockings & Stalkings Pt. 01

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Giselle applied the clear topcoat to her ruby-red lipstick; she pursed her lips as she looked at her reflection in the mirror. "There; finally finished," she smiled to herself. It had taken Giselle nearly one hour to transform from 'Gary', her male alter-ego, into Giselle, the hot transvestite staring back at her from the mirror. She smiled to herself as s...

Grab Bag Transvestite Story

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

I am a part time transvestite, who, if I do say so myself, looks quite attractive when dressed as a woman. It has taken me years to become adept at makeup and being capable of selecting sexy clothing that is in my size and that suits me. I have also had a number of lovely encounters with other TVs and male admirers. You can read my True Stories on this site....

I Love My Breasts!

by grgy56 on Dec 17, 2018
Transgender & Crossdressers

I Love My Breasts! Yes, that's what I said. "I love my breasts! Boobs! Knocker! Honkers! Fun Bags! Tatas! Tits!" It all started many, many years ago. I loved stealing glances of my father's Penthouse and Playboy collection. I could barely wait for my parents to leave so I could sneak a copy back to my room, lay naked on my bed and beat one out. I had to ta...

The Gender Pill Pt. 01

by MadisonWillow on Sep 14, 2020
Transgender & Crossdressers

As I stood in front of this beige-ish-gray brick building, I thought I was going to kill that bitch. If this rundown neighbourhood wasn't a clue I was in the wrong place, the nearly derelict building had to be. I knew the gender pill was too good to be true. Take a pill and the next morning you would wake up as the opposite gender. But still, I had hoped. Sa...

Two Way Display

by seams_straight2me on Jun 9, 2020
Transgender & Crossdressers

Whilst writing this story I realised I am hoping to build and extend the worlds of the main characters. Suggestions and ideas would be very welcome. Zoe's view: Three weeks forced with my feet up due to a sporting injury, doctor's orders. No sport, no fun, no weight on it. And even worse, this unfortunately also put a stop to going out as a crossdresser. E...

Forced Crossdressing Stories

by Dayeandknight on Feb 1, 2018
Transsexual

All of these stories share a central theme of Crossdressing. Rather than add yet another story for one of my ideas, new ones will now go here. I'm making the call, out loud, for additional authors to add their own threads and work with me. I would love anyone interested in any of these stories or my previous ones to add their own threads. If writing isn't yo...

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From a Husband to a Dutiful Sissy Ch. 01

by Sissy_Chantel on Sep 25, 2017
Transsexuals & Crossdressers

Preface: Welcome to my next sissy story. This one is based around the exciting ideal of a married sissy, crossdresser. It will have many ideas based on my thoughts about how life could be for me as a married, crossdressing sissy maid. I hope you all enjoy it. ***** Chapter One: Sometimes one's most unique secrets do come out. My name is Phil and I've alwa...

My Neighbour's Party Pt. 01

by Manndee on May 8, 2018
Transsexuals & Crossdressers

Part 1 Sometimes in your life you meet someone and just know they are amazing. Annie is the most energetic, enthusiastic person I have ever known - she has none stop energy. When Annie came into my life, I had no idea just how much my life would change. According to Annie, everyone knew Greg was different. He was a really nice guy, from a nice family, very...