Transsexuelle & Crossdresser Stories

809 results
Orientation
Length
Source
Infinite Scroll

Marion's Story Ch. 03

by Cagivagurl on Jul 6, 2020
Transgender & Crossdressers

Credit here to my friend and fellow author EM Kay (Marina Kelly) who helped with the story and kept me on the straight and narrow and of course did all the editing so thanks Marina.... A few days later I picked up my new guitar and it was perfect. Walking home you couldn't wipe the smile off my face. I locked myself in my room and spend the rest of the nigh...

The Robertson's Sissy Ch. 12

by Clite69 on Nov 4, 2019
Transgender & Crossdressers

**A quick note. The chapters of this story can fall into multiple categories, group sex, reluctance/nonconsent and transgender/crossdresser. If any of these are not your taste than this story may not be for you.** *** Lela lead her three slaves away as the two men followed. We were the envy of every other person at the party as Lela took all the attention...

Prom Queen

by komrad1156 on Sep 23, 2019
Transgender & Crossdressers

*Author's Note: I shared my own very unique love story in Serendipity. I got into crossdressing late in life compared to most guys who start somewhere between 5-15. I was married, and had been on active duty for four years and was totally into weightlifting since my sophomore year of high school. When I first tried wearing women's clothes, I was in my early...

Afro Stress Relief Ch. 10

by llts1970 on Mar 30, 2020
Transgender & Crossdressers

I woke up on the Saturday, not believing what I'd got up to in the Beer Bust and not sure what to do, now everybody knew what I was, a little white sissy bitch that worshipped black dick! How would everyone treat me on Monday at work, Elizabeth had said not to worry as 'what happens at the Beer Bust stays at the Beer Bust', however how could I tell my black...

You Can't Do That! Ch. 01

by qhml1 on Sep 26, 2017
Loving Wives

There's usually a kernel of truth in everything I write. In our thirty one years together "You can't do that" is one of my wife's favorite sayings. She knows that it irritates me and I have to prove I can. It took me about five years[I'm a man, we're dumb as rocks, ask any woman]to figure out she sometimes told me that just to get me do something she wanted....

Being Sarah

by Alex_Lockheed on Sep 25, 2017
Transsexuals & Crossdressers

Please note, this is a story about a male-to-female crossdresser. It includes themes of bisexuality, dominance/submission, embarrassing erections, anal play, cunnilingus and cum-eating. If you like that, awesome. If you don't maybe it's time to check another post. You can't say I haven't warned you ;) **** There are many difficult decisions I've had to ma...

Five Into Three Does Not Go

by scribbledehobble on Sep 14, 2017
Transsexuals & Crossdressers

Note to reader – This story has both transgendered and lesbian themes. It arose from an extraordinary story I once heard that quite illustrated the difference between smut and erotica. There are two groups of lovers, one group makes love, the other has wild sex. Not for the faint hearted! Note – The story is told from the perspective of five people – Jim...

The Robertson's Sissy Ch. 11

by Clite69 on Oct 22, 2019
Transgender & Crossdressers

**A quick note. The chapters of this story can fall into multiple categories, group sex, reluctance/nonconsent and transgender/crossdresser. If any of these are not your taste than this story may not be for you.** *** I woke from my early morning nap to the smell of Lela cooking in the kitchen. I rolled over and decided to sleep a few more minutes before g...

This to Keep Me Quiet Ch. 01

by MicheleNylons on Oct 5, 2020
Transgender & Crossdressers

Chapter One - It's Not Right Uncle John, For All Sorts of Reasons Author's Note: This is a little two-part tale similar to my early stories. It has all the trappings of a Michelle Nylons story: a little incest, a little blackmail, a lot of sex and a surprising ending. I hope you like it. Crystal Palace sat at the bar watching Melanie Starr singing The Cryi...

Dressed So Ch. 05: Tess' Friend

by MadQuill on Sep 25, 2017
Transsexuals & Crossdressers

The following is the Fifth chapter. This is the continuing story about Tess and her friends. Please consider reading the earlier submissions to understand the development of these special Ladies. ***** What was I doing! I had selected the file including my image and pressed send. I hadn't considered the possibility that Charles would react negatively to my...