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Transvestite sex stories.

Let the Team Erotica community drive you wild with our collection of scintillating Transvestite stories.

My introduction to sex and sissyhood

A true story on how I got into crossdressing and serving older men at a young age I'm very inexperienced with writing stories which is why I chose a true account to go off of but I apologise for my probably terrible style

FirstTimeSissy

Walking home in South Dakota - Ch 1

My introduction to sex, girls, guys, and cross-dressing in my early years. While it started out forced it soon became a distinct pleasure as I found out about both sexes.

dpga4625

Pantyhose CD Lexi Gets Dominated

Lexi is a CD with a pantyhose fetish and sexually versatile but prefers being a dominant top. This time she gets dominated and loves it!

Lexi Phose

Craigslist Tranny, First Time

I had thought about being with a transsexual and decided to contact them through Craigslist. I got many responses back wanting to meeting, but I couldn’t get the guts to pursue it, until I came across a post that simply said, "Satisfaction Guaranteed.”

markerss

Growing Up Chapter 7

Being a big brother/ house boy/ sex toy for a Sorority is pretty much the greatest job ever.

GoatRavisher

Neighbors Pt. 1

The Lesbian Neighbors help a femboy blossom out of his shell.

Phoenix Cinders

Jessy

A middle aged man discovers the young man next door likes to dress in his moms things.

travelguy51

Auntie’s home tuition (pt3)

Auntie wasn’t the only one that wanted me because while she was in hospital my uncle Robert let his friends use me for their pleasure, but once auntie Silvia was home me being used as an abused whore stopped.

Dave.Trudy2

Cock Pictures 6

Another story unfolding. A former member of the cock pictures site has a change of situation and comes back on the site.

MySemen

Summer's One night stand Suprise

A story about a slut that goes to nightclubs and always comes home sexually satisfied but this time meets somebody that opens her eyes to a new way of having sex and gets a huge surprise along the way.

Captain Boner

The Auction_(0)

Femboy gets tricked into being auctioned off as a slave

Phoenix Cinders

Danny becomes Danni. Part 4

First day at the boutilque Danni met Madelyn...which had lit the fire of lust between them...and after measuring...led Danni and Madelyn to have some incredibly erotic sex.

Danni8585

Danny becomes Danni. Part 3

Danni after having a night to remember...after admitting her crossdressing...in a vivid and slutty way...is going to enjoy the next day...

Danni8585

Danny becomes Danni. Part 2

Lynn and Jodi find Danni enjoying Kristin's cock, which leads to some confessions and even more steamy action...

Danni8585

Danny becomes Danni

A young man become a crossdresser...astory..and learns about his female side finding out his aunt is a lesbian and finding her lesbian friend's kids his age are there to Danny through his experimentation. .Part 1

Danni8585

Mama's Girl

In order to survive in the projects, white boy had to become an ebony woman's sissy bitch and take her big black dick.

Phoenix Cinders

Joey's First Detention

Joey Stevens, Superslut Part 2! Joey shows up for his first detention with Mr. Brennan.

MightBeRealz

Deal with a Demon pt. 1

The wealthy Draco Kostova just so happens to find a sexy femboy to his liking, walking alongside the road. His intentions for the boy aren't as pure as the boy's intentions. Draco wants to make a deal with the boy, will he accept? Or will he find out Draco's secret and run!

Wolf Hunt

Becoming Cara's Sissy_(1)

Here is a story about my ex and her husband, and myself. The first part is true. Where her husband enters the picture is fantasy. Names changed for anonymity of course.

jonialabaster

Joey Fucks Teach

A senior gets more than he bargained for when he tries to seduce the shop teacher.

MightBeRealz

Bitch in Heat_(3)

A young man finds out what it is to be dominated, spanked, and used as a young woman.

Randal Satyr

Hot Chocolate

Casey's twin sister Joanna has a hot new girlfriend that she's desperate to keep, the only issue is she's desperate for a blowjob, something Joanna is unwilling to provide. Fortunately for her, her brother with the right outfit and makeup looks just like her...

XtinaSmith

Working 'Girl'_(0)

A teen boy works the park late at night to make money in the best way he knows how.

mrseven

Working 'Girl'_(1)

A teen boy works the park late at night to make money in the best way he knows how.

mrseven

New identity

A man goes out in drag for the first time to see how people react.

luv 2 wear cotton panties

Pleasing Bill: A Crossdressing Story #3

]I woke up early the morning after my first day of being Bill’s live in slut. I got up to listen and hear my dad and siblings leaving for work around 7. I was going to wait for all of them to leave before I dress and go back to Bill’s at 12.

JessRider

Room Serviced

First time real gay sex for a man who has been fantasizing about it.

dlcalguy

Becoming Jane

The story of a young man giving into his desires.

maverick1989

Pleasing Bill: A Crossdressing Story #2

“Hello?” Bill said answering his phone “Hi Bill, it's me.” I said hoping he would recognize my voice sounding more girly then it was. “I was wondering how long it would be before you caved in and call me. So you ready to be a part time sissy bitch? “Yes, I wa

JessRider