Ladyboy Stories

221 results
Orientation
Length
Source
Infinite Scroll

Cockatoo Pt. 25

by nikkiesilk on Sep 13, 2017
Transsexuals & Crossdressers

Shane stuck out an enormous hand and I instinctively shook it, hoping for the first time in my life that my handshake would be a little limp. 'G'day girls. What a coincidence,' he said. 'I thought it was you on the dock but I couldn't be sure. I know you said you were leaving today, but who would have guessed we would be on the same ferry. I didn't know mys...

Cockatoo Pt. 18

by nikkiesilk on Sep 16, 2017
Transsexuals & Crossdressers

We finished dinner in the restaurant, then walked upstairs to the flat and sat out on the terrace, drinking and talking about what our next steps should be in the plan to launch the new club. We threw around ideas for possible names, some better than others, and we provisionally settled on Cockatoo Cabaret as a tie in with the bar. I also mentioned that whe...

28-year-old Bisexual Stepfather Ch. 12

by walterio on Mar 20, 2018
Anal

AUTHOR'S NOTE: This story contains straight sex, bisexual sex, gay sex and incest. *** A MASSAGE AND MORE Following brunch Ronnie and Dustin returned to her home. He had promised to give her a massage and she was looking forward to it. She took him downstairs to the lower level and it was the first time he was there. There was a massage table and a small...

Life with Tamsin

by kewtieboy on Sep 16, 2017
Group Sex

With a name like Tamsin you would be right in thinking my partner was born with a sliver spoon in her mouth. I suppose Oliver sounds a bit upmarket too but we did originally meet at University, her having come from a rather upmarket private school in England and I from a Grammar School. In our first year together the relationship was developed in the few hou...

Never Make the Last Out at Third

by Penelope Street on Sep 14, 2017
Transsexuals & Crossdressers

WARNING: This story contains graphic sexual descriptions. If you donโ€™t like, or may be offended by, romantic stories augmented by explicit sex, read no farther. This story is intended for adults only. Minors should in no way read any of what follows. The following is entirely a work of fiction. The events and characters described are completely imaginary....

The Good Neighbour Ch. 01

by MicheleNylons on Aug 21, 2019
Transgender & Crossdressers

Chapter One -- Mary Reynolds Now... Steven Balfour stared down at Abigail Thompson through his aunt's bedroom window. Abigail was on her knees weeding her garden. She used a plastic kneeling pad so that her knees didn't get dirt and grass stains on them. This caused her shapely bottom to rear up, which in turn caused her skirt to ruck up around her thighs....

Made to Obey Ch. 08

by madetoobey on Jul 29, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). Ruth, as a part of my punishment, was setting me tasks until Esther (who'd taken my laptop and mobile phone) could verify I'd never visited such sites before. I'd been forced into a chastity cage and m...

Marion's Story Ch. 08

by Cagivagurl on Jul 27, 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.... When we went down to breakfast Cindy and Jas were staring up into each other's eyes with Mel shaking her head in bewilderment. Jas and Cindy were head over heels in lust or...

The Vicar's Wife Ch. 25

by sarahloveitt on Sep 25, 2017
Group Sex

ONE Sarah knew that life could never be the same again after the sexual revelations played out over Christmas. It had certainly rekindled her sex life with her husband, George. After their morning threesome with their manager Janet, Boxing day had been a round of duty visits to hospitals and children's wards. But Sarah's mind was never far away from the act...

Code Name Tequila Ch. 05

by Travel_by_day on Sep 15, 2017
Transsexuals & Crossdressers

CIA agents Chambers, Cho and Juarez were sitting in the meeting room waiting for Black Oak to join them. All of them had received pages early in the morning telling them to immediately come to CIA headquarters. Chambers looked across at Cho and Juarez. As they had for the past week and half, they were dressed as women. Living as women, really, as Black Oak...