Ladyboy Fuck Guy Stories

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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...

Wild Asian Adventure Ch. 05

by SubBiLover on Sep 14, 2017
Group Sex

It was time to go. I threw on a pair of shorts and a shirt and watched as Karin slipped a little sun dress over her naked body. See that I had a feeling our clothes wouldn't be on long where ever we were going. We walked out and found grabbed a quick bite to eat before getting into a cab and going to an address that Karin gave to the driver on a piece of p...

More Than a Lady

by danielblue on Sep 14, 2017
Transsexuals & Crossdressers

Doctor Carter surveyed the gathering of ladies before him. Something wasn't quite right, but he just couldn't put his finger on what it was. He had been invited to speak on Female Reproductive Health but the women before him were neither the charity-driven older matrons nor eager young housewives that he expected. They were gathered in the private function r...

The Neighborhood Ladyboy Ch. 02

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, cross-dressing, and bad language, so if this offends you please don't bother reading. * It's been a week since that nameless Mexican fucker used and abused my asshole. What? He's not going to hit me up? Am I not good enough for him?! These th...

Made to Obey Ch. 01

by madetoobey on Jun 18, 2019
Transgender & Crossdressers

Let's get this straight. I'm not gay, not a sissy or faggot, I'm a normal 30ish heterosexual guy okay! So why you might ask am I writing this dressed in a dark blue dress, black stockings with suspender belt, light blue panties with a white polka-dot pattern and bow, matching bra, 3-inch-high-heels, with my cock in a chastity-cage and with my hair, make-up,...

Cockatoo Pt. 16

by nikkiesilk on Sep 14, 2017
Transsexuals & Crossdressers

I live for feedback. ***** We decided to have a celebration dinner tonight downstairs and Alex disappeared to the restaurant to organise the dinner. Areeya had to go down to Cockatoo to sort out some issues they were having and so I was left to my own devices for a while. We agreed we would all get together at Cockatoo for a drink before dinner. The firs...

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...

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...

My Treasure

by Tetris07828 on Sep 19, 2017
Transsexuals & Crossdressers

I drive truck. Have all my life, ever since I was a kid. My dad took me to my driver's test in a jacked up Ford 150 pickup and had to explain to the examiner that this is what I practiced with. Since then I got my CDL license and have been driving the big rigs. Got to admit, I love the life. You have to love it or you're going to be one miserable bastard. Th...