Ladyboy Stories

221 results
Orientation
Length
Source
Infinite Scroll

Another Day, Different Office

by chelseabi on Sep 16, 2017
Transsexuals & Crossdressers

It's been a couple of months since my first all guy encounter and my life has changed somewhat. There have been numerous liaisons, with couples and single guys and I know that I'm now treading a fine line between my marriage, work and the sex I now crave. As for my marriage things are normal, we have been together for years and as so often happens we have...

Dark Angel Ch. 01: The Meeting

by ReiverToo on Sep 12, 2017
Transsexuals & Crossdressers

It was after 10:30 pm when my Japanese business associates had finally had enough sake and karaoke to call it a night. Maybe they were just off to see if they could score some company for the rest of the evening. Who knew? They were all on huge expense accounts, so buying a girl (or boy) for the night was not a financial problem. Some had even offered to inc...

My First Ladyboy

by TheSevenSeas on Apr 20, 2020
Transgender & Crossdressers

She was my first. Before I tell you more about her and how I ended up in bed with this gorgeous creature, I should probably make a couple of things clear. First, I am a straight, alpha male. Ex-military, been through a few wars, worked in Africa for a while, have been married and never even looked at another male in a sexual way. Still don't, as there is no...

Naughty Thai Student Gets Extra

by StarfireMayo on Sep 12, 2017
Fetish

This is the third instalment from my Thai Journals. They recount the sexy autobiographical adventures of an expat working in Thailand. * When I held out the tub of Vaseline to the middle-aged Thai woman at the counter of Boots Chemist in Chiang Mai, she gave me a brief knowing but brief smile. "Another horny ex-pat "fareng" walking around with a sore di...

The Reunion Ch. 02: Thai Massage

by Valtikka on Jul 15, 2020
Anal

"Krissy! Long time no see! It's so good to see you. You look great girl!" As soon as I get out of the Uber, Micky comes walking to me with wide open arms and gives me a big hug. "Come let me help you with your bags. You're the first one to arrive so you have first pick on the rooms. The rest of the gang will arrive tomorrow." Instead of the overalls I'm use...

Sex therapist

by qaz on Sep 1, 2016
Miscellaneous

Who do we follow?What's next? A boy A girl What's next? A boy A girl...

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My First Ladyboy

by hornyrider on Sep 16, 2017
Transsexuals & Crossdressers

At 27 I reckoned I had the best job in the world. Twelve months ago I'd been appointed by the London-based international group I'd joined some five years before, to monitor the performance of our agents throughout the Far East from South Korea down to Indonesia and across to Thailand. No doubt one of the deciding factors in my appointment was that I was unat...

The World of Futadom

by Ammadillen on Jan 16, 2019
Transgender & Crossdressers

Futriarchal kingdoms empires and clans Futadom Empire Futa Shogunate Mandate of Futa*(part of the Chinese Empire) Futa Jallon tribes Golden Horde Indigenous Futa Futa Bongo islands Futa Jarldoms(part of the Futadom Empire) Patriarchal kingdoms, empires and clans The Federation of the free states The Papacy The Papacy colonial states African Defe...

Agnes Dourville Ch. 12

by ValoryG on Sep 16, 2017
Transsexuals & Crossdressers

When the massive shovel at the bottom of the open-pit mine drops its load into my oversized dump truck, I shudder along with the entire vehicle. In fact, the earth itself shudders. I'm being loaded with taconite by one of the largest hydraulic earth-shovels in the world. Wearing panties while doing so gives me such a perverse pleasure.... I gun the diesel e...

His Female Client is Really a Man

by walterio on Sep 16, 2017
Transsexuals & Crossdressers

Tim had just finished cutting the lawn and it was time to collect from Michelle Andrews. He always loved collecting from her as she always gave him the most incredible blow jobs. She didn't just suck his cock she made love to it. Sometimes she would make him last for 30 minutes before he unleashed a volcanic like ejaculation and sprayed his seed all over her...