Crossdressing Neighbour Stories

5,093 results
Orientation
Length
Source
Infinite Scroll

Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...

The Agreement

by komrad1156 on Sep 18, 2017
Transsexuals & Crossdressers

Author's note: I prefer to write in the third person as it gives the writer so much more flexibility. However, I've written this story in the first person for one reason—it is my own personal story with love, marriage, crossdressing, and the ups and downs it invariably brings to a relationship. My name is David Calvin Peterson. My friends call me Cal. A smal...

Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

Ugly Duckling to Sissy Princess

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

All names have been changed to protect the guilty. ***** Being a very short guy (5'3") with a small frame has been a major handicap in my quest for female companionship. Having a micro penis was the nail in my coffin. Throughout my youth, I was ignored or rejected by girls. I had my first girlfriend in college, Caroline Fletcher. She was smart, beautiful,...

Outing Ch. 02

by grgy56 on Sep 15, 2017
Transsexuals & Crossdressers

Unbelievably, my girlfriend Lora found out about my crossdressing activities when I was polishing her shoes (and my knob). She had me dress up in some new lingerie and fucked my ass. My face was splashed with my cum which Lora made me "clean up" and swallow. Then after changing for dinner, she made me answer the door where Megan the pizza delivery girl saw m...

Recruiting of a Sissy Maid Ch. 01

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

[Welcome to my next story. This story has become a little different in how I planned to write it as compared to my previous stories. It has been fully written up already, as of this first uploaded chapter. Doing it this way allows me to better proof read and adjust for future chapters before uploading each. I will submit uploads on a regular basis for my rea...

The Transition Ch. 01

by Quantarx on Jun 8, 2020
Transgender & Crossdressers

Greetings and thank you so much for choosing to read my story. This is intended to be a multi part series so bare with me as I try to develop the characters and lay down the backstories. As always, Your feedback is always essential in the development of the story going forward. Please leave a comment down below * I Had been Married for about eight years w...

Ugly Duckling to Sissy Princess Ch. 02

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

(Continued from Part 1) My girlfriend, Carol, and I made love to each other about 2 times per week. She was also getting fucked on a regular basis by her jock fuck buddies. I never asked how many guys she was hooking up with on the side, but, I guessed it was at least five, because there were five jocks that she tutored on a daily basis. She put on skimpy c...

Several Stories from Somewhere Else

by Freyasbearn on Mar 11, 2018
Fantasy

This is the landing page that will take you to the several stories re-archiving here. I am also using this section for new stories with the same themes as my other stories. That way I don't have twenty different stories all over the place that cover the same stuff. You can get it here. If you want to add on, or take a story a different way-- please, please d...

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Fulfilling all My Fantasies Ch. 01

by classmate1119 on Apr 23, 2019
Transgender & Crossdressers

"Last chance to change your mind, Cristi," Jalen said. "It's probably the most outrageous one so far! Not that I'm worried, of course, but you never know what else might happen... " I reapplied my lipstick in the reflection of the club's glass entrance. "Hey, we spent too much time preparing for this. Don't back out on me now, Jalen!" I threw him a coy smi...