Ladyboy Stories

221 results
Orientation
Length
Source
Infinite Scroll

The Neighborhood Ladyboy Ch. 01

by Rstyusameg on Sep 16, 2017
Transsexuals & Crossdressers

All characters are fictional, except me, everyone in the story is over 21. My stories will involve, male/male sex, crossdressing, racism, bad language, and drug use. So if this offends you please don't bother reading. * Wearing my favorite low cut denim jeans, showing off the "tail" of the whale from my stringy pink thong, I walked into Albertsons. A loca...

Seduced and Hoodwinked Ch. 02

by walterio on Dec 31, 2017
Transsexuals & Crossdressers

ACCEPTING JASMINE Thursdays were working out wonderfully for Darin as a masseur at the Spa. He would massage the voluptuous Rita first and as always, she would leave him with a boner and ready for sex. Jasmine was his second and only client and they would spend hours together. He massaged her lovely petite body and he loved her tits and ass. She loved the w...

Encounter of the First Kind

by gendidi on Sep 16, 2017
Transsexuals & Crossdressers

I'm a married man in my mid forties. I have an older disabled wife. We don't have any children. We have been married for a decade. Ever since she was disabled, we stopped having sex. She gets depressed occasionally and has been taking happy pills for years. Maybe that's why she lost her sex drive and I don't blame her. We never discussed about sex. I assum...

My First Ladyboy Experience

by Junglist187 on May 11, 2020
Transgender & Crossdressers

I'm a typical man, big hairy and rough on the edges. For as long as I have had internet access I've always been drawn to watching shemale/ladyboy porn, just the sight of such magnificent female bodies always ignited a flame in my crotch area, I had masturbated to these clips thousands of times and I still do to this day. That was as far as that went. I r...

The unexpected housekeeper

by manhasso on Mar 30, 2020
Transgender & Crossdressers

After experiencing difficulties in his personal life, a lawyer discovers the benefits of having a live-in housemaid. 1.Prelude After almost 20 years of legal profession, I was now an accomplished lawyer: I had my own firm, several younger lawyers working for me, big and important clients, a sports car, and a house on the hills overlooking the city. But...

Business to Improve Sex Lives Ch. 05

by walterio on Oct 23, 2018
Novels and Novellas

MORE EROTIC TRAINING ON THE AGENDA Trace and Brittany woke up in a spoon position with his morning erection pressed into her curvy bottom. His hands encircled her upper body and fondled her lovely breasts. If they didn't have a client that day they would have made passionate love as they always enjoyed each other so much. "I really love your body and cares...

Face Down Ass Up

by Junglist187 on Jun 1, 2020
Transgender & Crossdressers

A few years ago whilst living in Manila in the Philippines I met and formed a very strong friendship with Leslie. Leslie was a very petite ladyboy I had met online on one of the dating apps, we had chatted for a few days and then we planned on meeting each other face to face. I had already told her that I'd only ever met one ladyboy before and had really...

Flavia's Secret

by TimT1972 on Sep 16, 2017
Transsexuals & Crossdressers

Filipe had always yearned to wear satin knickers. He loved the idea of wearing tight, little briefs made of sensuous silky material. He simply could not see why boys should not be able to wear silks or satins instead of plain cotton. But at home he had no opportunity to satisfy his desires. His mother would be sure to find any illicit underwear and then ther...

Makati Ch. 05

by massageaddict on Jul 15, 2020
Novels and Novellas

I sat at my favorite table smoking when Lilly showed up to ask if I needed anything. I asked for a bottle of Perrier and she smiled and said "Right away Mr. Bob." I sent off a few emails, sent some pictures of the new place to my wife and then scrolled through my WeChat deleting all the whores wanting to connect then checked my Whatspp. I had a message from...

My Thai Ladyboy

by TheSevenSeas on Apr 27, 2020
Transgender & Crossdressers

There is a saying that 'when one door closes, another opens.' That was certainly true for me. My relationship with Jen (see my previous story: My First Ladyboy) continued for some time, but we rarely managed to see each other. I was mostly working in Africa and just couldn't get over to the Philippines very often. Eventually we drifted apart. Yet I was truly...