Crossdressing Aunt Stories

13,440 results
Orientation
Length
Source
Infinite Scroll

iPad Roommate

by Oddballs on Dec 31, 2020
Science Fiction

“Pffff, another sweater.” Aaron says as he holds up the red, green, and white Christmas garment is aunt sent him. “At least this one as an actual cool design on it.” Ian says as he smiles at his roommate. In a small house in a secluded neighborhood covered in snow, two men in their mid-20’s enjoy a simple holiday together. With the pandemic still at large, b...

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Futanari World

by styxmaster on Apr 16, 2016
Fetish

You wake up this morning to the sight of your younger sister Sarah pulling your covers off of you. "Get up Doug, you don't want to be late for school." You get dressed for school after Sarah leaves your room. you never mind school that much, you mostly get B's and A's in your classes but given the opportunity you would like to just stay home and wa...

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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...

Becoming Cassie Ch. 11

by TGJamie on Sep 25, 2017
Transsexuals & Crossdressers

On New Year's Day, I slept late, real late. I was still trying to process the month of December. It was clearly a month I would not forget. I did a lot of daydreaming that day and watched TV with the family. I was pretty zoned out. New Year's Day simply came and went. My cell phone rang early the next day and I was asked to price out 2 different painting j...

Julia, Ben and Lisa Ch. 08

by chloejacobs83 on Mar 2, 2020
Transgender & Crossdressers

Ch 08: Tuesday A few quick notes: 1. this is the eighth chapter of a longish story, a novel in many chapters 2. everyone is 18+ 3. there is no safe sex here - cause it's a fantasy, not an instruction manual 4. crossdressing and gender bending, not everyone's cuppa tea - be forewarned I'm sorry for sounding so stupid back there. For sounding like I'd never...

Return to "Weekend School" Ch. 14

by cynthiablaine7 on Oct 26, 2020
Transgender & Crossdressers

[This story involves bodily functions and sometimes severe disciplining, including caning and spanking, as well as crossdressing. If reading about those offends you, read no further. These stories may be read separately but do gain from being read in sequence.] Laura Franklin wasn't sure what kind of response she would receive when she sent out notices by m...

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...

Latex School Girl

by latexcd69 on Sep 25, 2017
Transsexuals & Crossdressers

Not many people knew about my crossdressing. My mind would fill with worries about what everyone would think. I did tell two of my friends, David and Nick. They were experimenting with bisexuality and very open minded. Somehow I knew they would be more understanding, and they were. The three of us lived in a small house for the price of an apartment. It see...