Transgender & Crossdressers Stories

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My First Crossdresser

by Jay876 on Jul 31, 2019
Transgender & Crossdressers

Monday A year ago. I was sitting in my flat, as a university student just browsing the men on grindr. I was inexperienced at the time and I had only been with one man, and that was just for oral. So, I was intrigued when I saw someone on my page, just nine meters away. A crossdresser, stocky, but wearing a maid costume, with his ass bent towards the camera....

Farzana Khan of Ottawa

by Samuelx on Sep 16, 2017
Transsexuals & Crossdressers

"Nice ass, them Indian girls sure got nice bums on them nowadays," Geoffrey Kean said to himself as he spotted the tall, curvy, Sari-wearing young Indian woman getting off the 95 bus at Mackenzie King Bridge in downtown Ottawa. This particularly Indian cutie strode through the crowded hallways of the Rideau Shopping Center like she owned the place, sashaying...

Dubrovnic

by Sean943 on Dec 24, 2019
Transgender & Crossdressers

Although still in Southampton, I was between assignments. However, my friend Bjorn's Consortium client was looking for someone to attend a meeting on their behalf in Dubrovnik; this time for five days. Hanna or Suzi had arranged my hotel and travel from Gatwick, together with all the contract paperwork and authorisations. An early start but I arrived the...

Bisexual Men's Wives Ch. 06

by Samuelx on Jun 26, 2019
Transgender & Crossdressers

Consider Dr. Tyrone Sheridan, a Boston-born and McGill-trained therapist living and working in the City of Ottawa, Ontario. He's the author of In Defense Of Black Male Bisexuality, a controversial book which nevertheless spent eight weeks on the New York Times best-sellers list in 2018. The successful author, father of two and therapist has now turned his fo...

Sarah has Some Thanksgiving Fun

by SarahCD on Dec 3, 2018
Transgender & Crossdressers

I first published this story a few years ago. Since then my writing skills have improved a little. While I cannot change what actually happened to me, I have added some more details and corrected some grammatical mistakes. --------- I felt like going out as Sarah and being a naughty girl. So I advertised on Craigslist for a naughty play mate. I had a prom...

Sarah Asked to Work as a Hotel Maid

by SarahCD on Dec 17, 2018
Transgender & Crossdressers

A few weeks before the events described here, I had watched a transgender porn video. It was about a guy who dressed as a French Maid and worked in a hotel. I was so excited by what happened to him, I wanted to give it a try. I searched on-line for an LGBTQ friendly hotel and found a promising one close by. I emailed them and asked if I could tryout as a 'ma...

My Friend June

by wife2hotblk on Sep 16, 2017
Transsexuals & Crossdressers

I met June at the local support group for women with mental health issues. She is a transsexual woman in her late fifties. Of course, June was the type to stand out, so I had seen her around our neighborhood for some time. Like most people, I admit I was curious. But unlike others, who taunted and tormented her, I was too polite to inquire. But over the week...

The Longest Road Pt. 04

by Ilbfita on Sep 16, 2017
Transsexuals & Crossdressers

Fencing is a difficult and dangerous job. To be effective, fence posts need to be in straight lines and spaced evenly. If there is a five tonne rock or a one hundred year old gum tree where the fence post needed to go, then too bad, the fence needed to be straight. Barbed wire needs to be tight, and applying tension to it is risky. Fencing was normally done...

The Final War

by Dar_Jisbo on Feb 26, 2019
Transgender & Crossdressers

It wouldn't be much, I knew. But at least if I built it, I could survive the inevitable for a couple of weeks. And so could my girlfriend. So I quietly had the sealed-from the-outside-environment shelter built, stocked with enough caustic potash to absorb the carbon dioxide exhaled and some pure oxygen to resupply the air with. And enough food and water to...

CD Asst. Secy. Ch. 05: 1 yr. Later

by cdtycoon on Jun 2, 2020
Transgender & Crossdressers

On 9th December 2020; as now my daily routine, I woke up and went to the hospital, took the CEO's car, and brought Mam and secy. from their homes, then went to park the car and went to the CEO's office. Well, it was like any other day and was pretty normal even though it was raining outside as it was a winter monsoon season. But still, I notice that somethi...