Crossdressing Stories

1,097 results
Orientation
Length
Source
Infinite Scroll

Obey Thy Neighbor Ch. 06

by jealouscuck on Nov 6, 2018
Transgender & Crossdressers

When Chelsea returned from her out of town assignment she was excited above all expectations. She kissed me hungrily and thanked me profusely for letting her experience sex with a well hung man. She questioned whether I had any regrets. I did not. When she heard this, she expressed to me that the only second thoughts she had about it was if it somehow began...

Cum and Dress for Me... Pt. 01

by Manndee on Mar 28, 2018
Transsexuals & Crossdressers

I saw the advert in my local paper - it just jumped out at me! Then I was surfing the internet, usual stuff, looking for something to get horny over... WHAM!! The same advert appeared within three days of seeing the advert in the paper. I'm not into that hocus pocus stuff, but it seemed weird that within three days I had seen the same advert. I felt compelle...

More Lessons with Kelli Ch. 01

by Lifeatlarge on Sep 19, 2017
Transsexuals & Crossdressers

Writers Note: I had written the first three chapters of our story a while ago but it took some time for me to convince Kelli, who is a very private person except to a few, to let me put it on here. I had planned on ending the story after the last chapter but there has been a lot of things happening in our lives over the last year and since Kelli has had a lo...

Brazilian Discovery Ch. 02

by dan57 on Sep 15, 2017
Transsexuals & Crossdressers

by Dan57 with characters from Jill York Chapter 02: First days in Brazil The tub was so large that it could have been a small swimming pool. Joan plunged into the water and started to lick Barbara's pussy underwater. When he rubbed the tip of his nose against Barbara's clit, she mightily climaxed several times in a row! Sometimes, instead of plunging deep...

Happy 21st Birthday

by lpacphantom on Sep 1, 2017
Group Sex

This is my first submission, the first time anyone but me has read my work. I would like constructive feedback. I hope you enjoy. The events are fictional, but the desires and characters are based in real life. This story contains male on male action and hint of crossdressing. If that offends you, don't read it. It all started before I even had my first...

When Finally We Meet

by oberon_52 on Sep 16, 2017
Transsexuals & Crossdressers

Dear John: This is the last e-mail you will receive from me before we meet. You had read my previous story, "Visit to an adult store," in which I had my first gay experience with a much older and stronger man and was forced to wear a sexy, off-the-shoulder, bare-midriff harem outfit while he ravished me. Over the last several months, you and I have gotte...

Sissy's Decline into a Slut Pt. 03

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Five: Oh, Oh, Things Look to Begin to Radically Change for Chantel. Well another week has passed by, it's Friday evening and tonight I have to go back to the rest area to hook up with Barry and Ralph as they instructed from last Friday after having me suck their cocks. They promised me that they will fuck me tonight and share me with even more men....

Sweet Treat Ch. 04

by SaucyMasquerade on Feb 25, 2019
Transgender & Crossdressers

"Ok, in here is the photographic studio, it may seem a little intimidating to start with, but unfortunately technology can be a little, how you say, unkempt." As I followed him though the white glossed six panel door, I was struck by the contrasting halves of the room. At the far end on the left wall was another door, but centre piece to the room was the la...

Lost in a Female's Pleasure Pt. 03

by LucysFox on Mar 11, 2019
Transgender & Crossdressers

Synopsis: Damien had been looking forward to a relaxing weekend free from his abusive father, but things quickly take a downward turn when he's kidnapped and wakes up in a confusingly elegant room and learns that his life is about to change forever. After a confusing few hours of fear and pleasure he collapsed, and after waking up he is dressed and led towa...

Barrack Room Betty Ch. 02

by MicheleNylons on Oct 8, 2019
Transgender & Crossdressers

Chapter Two – Wren Division Ho! The four Leading Recruits were hungover and hungry and in the grey dawn and cold bleak light of day they weren't sure that their prank was really worth it. They entered the cabin and found the four 'Wrens' stood at attention and immediately began to break down in laughter. "Of my fucking god you guys look stupid!" Jean Burge...