Ladyboy Stories

221 results
Orientation
Length
Source
Infinite Scroll

Seduced and Hoodwinked Ch. 06

by walterio on Jan 14, 2018
Transsexuals & Crossdressers

Darin woke up on Sunday morning alone in bed. It was early and the others were still sleeping. He took his morning piss and then crawled back in bed. As he had done the night before, he contemplated his current situation. He was very content with things at the moment but he would continually re-evaluate it again the coming days. He still had no interest in d...

A Teen Seduced and Hooked on Anal Ch. 08

by walterio on Aug 5, 2019
Group Sex

AUTHOR'S NOTE: For this episode I changed the category from Gale Male to Group Sex because there are threesomes and straight sex in the story. TUESDAY'S SHOOT Eric was up early and worked out at the fitness center since the filming was set for late morning. He had eggs for breakfast again after his workout. He was at the studio by 9:30 and the filming was...

The French Exchange Ch. 02: The Pain

by Praeparvus on Sep 1, 2017
Exhibitionist & Voyeur

The first three weeks of my six-week stint in France as a language exchange student had been the strangest of my life, chiefly due to my chronic bed-wetting habit and my distinctly unimpressive anatomy. The second three weeks would be even weirder, and would mark me both physically and psychologically for the rest of my life. I was staying with the family o...

Cockatoo Pt. 02

by nikkiesilk on Sep 14, 2017
Transsexuals & Crossdressers

I live for feedback. Part 2 Everyone had said that Alex was good looking back at Uni and many of the girls had even said he looked quite pretty. As she held her hair back I could see that it was Alex's face looking back at me. 'Oh my God,' I couldn't think of anything more original to say, 'It is you.' She smiled and stood up, took my hand and pulled me...

Oh Carole Ch. 03

by Croony on Apr 24, 2018
Mature

The phone rang one evening and Carole answered it. 'Carole? Hi darling it's Cynthia. I know you have a day off tomorrow but would you be a dear and meet me for lunch? My treat. Say The Ivy on West Street? It is very discreet. Shall we say one o'clock?' Cynthia was talking so fast all Carole could do was listen and say yes at the appropriate moments. The n...

The Advice Columnist

by colonellunchmeat on Sep 16, 2017
Fetish

Dear Debbie: What is your opinion on your submissive's RIGHT to occasionally kiss your boobs? My husband is totally hot for my full, pink 36D melons, but since he became my slave,I gradually weaned him off of them. Part of the problem is, I'm not as attracted to Joel as I used to be, he's kind of chubby now, and having his hands groping me when he brushes...

An Opening to Be Filled

by spitzharder on Sep 16, 2017
Transsexuals & Crossdressers

Aki was stroking me, her fingertips were lightly touching my small stiff member, hers too was stiff with lust for me. She had pushed my blouse up over my small breasts revealing their swollen nipples to the cool night air, her kisses upon them had left them stiff and turgid. I reciprocated with her bigger breasts, freeing them from restrictive clothes, sighi...

Barrack Room Betty Ch. 15

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Fifteen - Bettys Down Under Michele had an emotional last day with Ying. As well as lovers they had become good friends. Michele promised to write to Ying and vowed that one day she would return to Thailand and they would reunite. Their last night together was a sex charged boozy affair and Michele rose early the next morning and left Ying fast asle...

A Very Different, "Three's Company" Ch. 05

by walterio on Oct 21, 2019
Group Sex

Jack, Chrissie and Janet were sitting on the deck out back. It was a Sunday morning and they were reflecting on the weeks' vacation in the Caribbean. They had heard that things could get wild at the all-inclusive resort but they never expected what they experienced. Chrissie offered, "I wish that we had places like that here at home." "There are some sens...

Hi, Polly

by MawrGorshin on Sep 16, 2017
Interracial Love

In Pattaya Beach, Thailand, Polly, a short, pretty young Thai prostitute, was chatting with her ladyboy friend Anchali. They were sitting on the steps of the entrance to an eatery owned by Polly's older brother. As the two friends were chatting, Polly watched the white male tourists as they walked by; she smiled at the better-looking ones. Anchali frowned....