Ladyboy Stories

221 results
Orientation
Length
Source
Infinite Scroll

Swiping Right for Susan

by aussie_101 on Sep 12, 2017
Transsexuals & Crossdressers

I very nearly swept left. I mean, she was gorgeous. Better than gorgeous, quite honestly. She had the body: curves and boobs, legs and rump. She had a very pretty face, and a beautiful smile - a real light-up-the-room beamer, a genuine smile. I was drawn to her, and I don't mind admitting it. And that's exactly what I was looking for: a connection, an attra...

A Very Different, "Three's Company" Ch. 03

by walterio on Sep 24, 2019
Novels and Novellas

Jack, Chrissie and Janet had been roommates for months. Chrissie and Janet loved staying at Jack's house with the private swimming pool, jacuzzi and sauna. Most of the time they spent in the backyard they were naked. The three of them were tan from head to foot. They often had sex when outside and sometimes in the pool and jacuzzi. Chrissie liked to ride J...

Once Upon a Laundry Ch. 02

by thekestrelkid on Aug 7, 2018
Transsexuals & Crossdressers

At 7 sharp I knocked on Jessy's door nervous and anxious still not entirely sure what I was doing. I couldn't believe how hot a time I had down in the laundry room with her making me finger my own ass like a "pussy" and jerk off for her. The thought of taking it to the next level was exciting. Jessy answered the door dressed only in an over sized t-shirt a...

Getting the GED

by turo69 on Sep 16, 2017
BDSM

Part One Well how did I get here? Bob Tucker, newly retired at 55, not buff but not quite squishy, fairly comfortable, never married and still a certifiable horn dog. An athlete through college and still pretty active, but with an overactive sex drive. My investments and real estate holdings together with a 20 year pension courtesy of our local school distr...

Me & My Wife Are Sisters Now Ch. 02

by gayindia1980 on Sep 16, 2017
Transsexuals & Crossdressers

This story is in continuation of my last story Me & My Wife Are Sisters Now Ch. 01 ***** Next morning, we both slept quite late then our usual time, I don't know about Shivika but I was still feeling cum inside my ass. Last night my wife, Shivika was fucked by 2 sexy men in a 3some and then one of them fucked me really hard. Shivika woke up around 9:30 an...

Sex with Shonda

by rawpump on Sep 16, 2017
Transsexuals & Crossdressers

I'm a workaholic by nature. I love my job but that's not why I work so much. I work long hours simply because when I get home I don't quite have anything productive to do. I just sit down in front of the television or I chat over the internet. Life at home is dull so the best solution seems to be engaged in work. Often on Friday, after work, I head to the...

My Visit with a Filipina Friend

by esclaro on May 6, 2019
Transgender & Crossdressers

This is the story of my week long visit with a Filipina ladyboy in Hong Kong. She is a 31 year old nurse who has worked all over the world but now helps her mother run a supermarket in her home town. Since she is from a bad area of Mindanao, I arranged to meet her in Hong Kong. We had been chatting daily so I was eager to see her and see how we got along in...

My Experience So Far

by PeterBenjamin on Sep 16, 2017
Transsexuals & Crossdressers

I don't know where it first began but I remember working at home depot in 2007, watching a gay man in a purple rainbow tshirt walk around the store, and thinking, "you know what... I should suck his dick." The thrill of just thinking that sent a wave of weakening chills through my body. I have never been the same. At that time AOL still had its gay chat and...

Satan's Sissy

by nancyvasquez on Oct 15, 2017
Transsexuals & Crossdressers

Oh you stupid little faggot! You just had to go and get married to a woman! Why?? Why fuck up some poor girl's life like that? Was it because you crave humiliation, and subconsciously you knew it would be just a matter of time before you got caught, and you would be outed publicly? Outed as a pole smoking homosexual who was more at home in frilly skirts and...

Delectable Debbie

by Pussrider on Sep 16, 2017
Transsexuals & Crossdressers

I can't explain why it was that I fancied having sex with a transsexual. I mean I'm a perfectly normal happily married man, couple of kids, mid-40s, a stone or so overweight but reasonable looking, my own hair and teeth and everything. I must admit, I've been with one or two...escorts, hookers, whatever term you prefer, over the years, but always very womanl...