Transsexuals & Crossdressers Stories

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A Full Day for a CD Wife

by pushinme on Jul 14, 2020
Transgender & Crossdressers

One of the weirdest gurl days. My bf at the time loved me dressing. Whenever I was home, I was expected to be dressed. It was especially great for long weekends. He had been fucking me trying to knock me up for the past couple months. It was hot. I loved the attention, even though I was pretty sore most of the time. Playing housewife just made him very horn...

At Home with Phyllis Pt. 01

by IcelandSpar on Sep 24, 2019
Transgender & Crossdressers

Waiting for Phil to get his kids ready and out the door, I thought back to when we had first met, a work event some time ago. A conference, a shared hotel room, a brushing together -- bald, chubby, I would have never pegged him as "my type", and yet here we were. I had arrived some minutes back, and he had ushered me into the home office, telling his kids w...

Letter from East Hesburgh

by justincbenedict on Sep 24, 2019
Transgender & Crossdressers

Dear Shoeblossom Flash loves to tease my butt-hole, she runs her long nails in and out, and then, of course makes me lick off the crud. She will use her other hand to twist my cock head about, what do they call it, the glans? like she's trying to open a bottle of baby aspirin. I'm standing in front of Flash, who is resplendent in her little leather miniski...

The Wife Swap with the Witches

by marylatexrose on Mar 9, 2020
Transgender & Crossdressers

It was a typical dinner with the neighbours. My wife, Emily, and I had cooked up some lasagne and invited over the lesbian couple next door. We chatted and laughed over our stories and anecdotes. I enjoyed the conversation; I enjoyed looking at our gorgeous neighbours. It was a perfect evening. Soon the conversation veered to the topic of our sex lives. My...

Ultimate Sissy Weekend Ch. 05

by SissyTwinkleToes on Jan 21, 2020
Transgender & Crossdressers

Susie can feel her diaper getting warm as she fills it with more pansy pee. 24 hours ago, she posted an envelope containing five keys, and still has another 48 hours until they arrive at her house. Those keys are for the lock that keeps her in her dress, the handcuffs that keep her right hand locked to this sissy on her left, and the tiny pinching chastity c...

Lingerie shopping

by Geraldine21 on Jan 27, 2020
Transgender & Crossdressers

This is a story of a recent experience that I would like to share with you. Firstly a little about myself. My female name is Geraldine I am aged 33 and have always been fascinated with womens clothing. I spend many an evening in my flat trying on various outfits and making provocative poses in front of my full length mirror. I run quite a lot and do plenty...

From John to Jenny

by GaysonPerry on Apr 20, 2020
Transgender & Crossdressers

John put on the little black dress and became a she, her little clitty slipped out from beneath the red lace panties and she fondled the outside of the lacing. With this, she felt sexy: combined with the 'fuck me' pumps and a red bra she was about ready to be a sissy, except there was nobody around except her and her toys. All that ruined the illusion was...

Crossdressing Confessions Ch. 01-02

by EvelynWilde on May 11, 2020
Transgender & Crossdressers

A photograph of a flower hangs on the other side of the room, taunting me. The petals push softly into the lens, curling back on themselves on the tips. The black and white blossom rests on the dark, graceful contours of a wooden slab. I was never fond of photographs. For the longest time I suspected it was that the camera lied, that the light would never h...

Sub Lucy Takes Dominant Sex

by Intercontinental on Jul 30, 2019
Transgender & Crossdressers

It was not a simple wish. It was a need. A desire. Lucy had not been fucked for months, and she needed it. The preparation was an essential part of the ritual. A piping hot bath, the scrupulous washing and cleaning, the razored smooth armpits and legs, that tingling scented sensation on her naked body as she towelled down before returning to the bedroom to...

The Making of an Angel Pt. 03

by AngelLawrence on Jul 31, 2019
Transgender & Crossdressers

The making of an Angel part 3. All persons are over the age of 18. *** On the drive home a myriad of thoughts were tumbling through my mind. I'm not gay but I could smell the stranger's cum on my breath and feel my panties teasing my puckered tight little hole. I was aware of my suspender clasps digging into my thighs and the feeling of the sheer nylons o...