Transsexuals & Crossdressers Stories

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First Shemale

by mac053 on Apr 27, 2020
Transgender & Crossdressers

Lately I've been thinking about sleeping with a shemale. I'm in my late 60's, look 10 year's younger and, for some reason, I'm really attracted to shemales. There are a two LGBTQ bars in my area and I found one that I thought might work. I had no idea what I would do once I got in the bar, but this was an itch that I had to scratch so I went for it. When I p...

Edged in Public

by yorktvjane on Jul 15, 2020
Transgender & Crossdressers

So, my on/off BF is mad on my legs and feet, he likes to see me wear nice heels in public and loves me to tease him in public. Just lately things have taken a twist and he has a new thing he likes. It started about a year ago, we were walking by a quiet river side path just of the main Street (North Street) in York center, it was about 8pm at night and it h...

From Husband to Man's Sissy Wife Ch. 02

by Pantypansy on Jul 9, 2019
Transgender & Crossdressers

I had just finished changing into a black satin, frilly French maid's outfit - which Hamish had picked for me - when I heard voices downstairs. I pulled my silk panties up tight and put on a pair of black high heels and tottered down the stairs. Hamish had changed into jeans and a button-down shirt, and was chatting to my wife in the kitchen. Both were l...

A Girls Night with My Wife

by erinpiers on Jul 10, 2019
Transgender & Crossdressers

I'm never going to fool anyone when I dress up, at five foot seven inches, with a heavy muscular build, I'm definitely not what you call feminine. But no matter what I do I cannot help but feel incredibly sexy when ever I get ready to, as my wife and I call it "dress up for a girls night". I always take my time in the shower, shave and trim as closely and a...

Waiting for My Sexy CD Slave

by eljayb on Jul 3, 2019
Transgender & Crossdressers

Sitting here waiting for my sissy lover She is due in 90 minutes. She has just received two new dresses to wear plus assorted lingerie and I am to pretend be a photographer from a model agency who will gradually reduce her inhibitions about posing until I am lying on the floor shooting straight up her skirt. Then the real fun begins because I shall lead he...

Connor and Me Ch. 02

by Corjix on Jul 3, 2019
Transgender & Crossdressers

How can a man explain the feeling of his ejaculation? It's not difficult in the beginning. There is a general rush of tingling that quickly flows down the body, followed by a definite understanding that the storage tanks that hold his semen and fluids begin to open; and empty their contents into his stream. The tubes that carry the flow can be felt, as they...

Soma's Journey Ch. 01: First Time CD

by SomaSlave on Dec 3, 2019
Transgender & Crossdressers

I never thought my first encounter involving a CD would be with me as the CD, but strange are the ways of sensual exploration. I had answered an ad looking for a man who wanted to play in stockings and panties. After establishing my submissive nature (and torturing me with wonderful photographs of CDs in bondage), the man at the other end of the ad had persu...

At Home with Phyllis Pt. 03

by IcelandSpar on Nov 12, 2019
Transgender & Crossdressers

(Since one of you mentioned liking the "episodic" nature of this, I'm sharing 1000-word increments. Again, please do email me if you like something, I like to hear about what you liked or didn't like. A caveat for this story though: it turned out to be light on action and heavy on dialogue, apologies if that doesn't suit your mood, I'll probably balance that...

Nicki in Bangalore Ch. 02: Next Morning

by oldindianpervert on Dec 10, 2019
Transgender & Crossdressers

I woke up with a hangover. I waited for my eyes to adjust and squinted around. He was in my bed with his legs wide open his dick was covered in dried cum. I moved out of the bed slowly and quietly. I splashed some water on my face, I could see the red bite marks on nipples from previous night and i still felt them tingle. I applied mosturizer on them and sl...

Simply Submissive

by cdnoir02 on Dec 16, 2019
Transgender & Crossdressers

It was an ordinary night, apart from the fact that I had something extra special planned. I had been talking to a man (we'll call him 'J') online for a few days now, and after exchanging some pictures and contact information we had agreed to meet up. I had gotten home from class around 9:30pm, and immediately went into the washroom with a razor to make sure...