Chastity Crossdressers Stories

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Sister is My First

by assslut on Sep 13, 2017
Transsexuals & Crossdressers

It was the first week of June and school was out for the summer, I was 18 and had just finished my senior year. One night while we were eating dinner, My Mom and step dad informed me that they were going away for two weeks. When they got married they did not go on a honeymoon, so they wanted to take one now. Jack, my stepdad, told me they were going to Jamai...

Christine and the Neighbor

by Lovetoshowoff on Sep 13, 2017
Transsexuals & Crossdressers

Hi. My name is Chris, though some know me as Christine. I am John Collin's "wife". We care deeply for each other. John "keeps" me, he supports me financially and in return it is my pleasure to keep his sex life exciting, as well as to entertain any of his gentleman friends who drop over. It all began innocently enough, I suppose, when I had just turned 18...

A Whole New Me Ch. 02

by libertinaXx on Sep 12, 2017
Transsexuals & Crossdressers

I had just finished cleaning up in the bathroom. A spontaneous encounter with my best friend whilst wearing my girlfriend's thong had left me a bit of a mess and as for the thong... well I guess I'd need to find something new. Fully cleaned up, I ran naked into our bedroom and started looking through Lisa's drawers for a new pair of panties. I wasn't sure h...

Up to Scratch

by spitzharder on Sep 14, 2017
Transsexuals & Crossdressers

Pushing away the coffee cup, the flash of my red painted nails caught my eye in a nearby mirror. Judging by the reflected sideways glances from men in the café my facial surgery had worked even better than I had thought. I was a 24 year old Shemale, with long dark hair and breast implants to die for. New in town due to a job transfer, I wondered what I shoul...

AlabamaNan: Bathroom Sex

by AlabamaNan on Sep 14, 2017
Transsexuals & Crossdressers

This story happened early on in my transformation from Nathan to Nancy. At this point in my life I would rarely venture out as Nancy in public, I had however replaced ALL my male underwear with women's bra/panties...and I HAD STARTED to wear ladies underwear on a daily basis under my regular clothes. I was out running errands and found myself on the seedy...

Forced Out

by KuroshioX on Sep 14, 2017
Transsexuals & Crossdressers

My head hurt like shit. That much was to be expected after a full night of heavy drinking, but it still didn't make the headache anymore welcome inside my skull, merely a casualty in the war of college drinking. I didn't even want to open my eyes; I knew I'd be visually assaulted by sunlight, even with my face under the sheet, and didn't have anywhere to be...

Sissy Hubby Ch. 02

by buttboi on Sep 19, 2017
Transsexuals & Crossdressers

I awoke the next morning feeling refreshed and better than I had in a very long time. Rolling over to find my wife Stacy had already left for work. After finishing graduate school two months ago, my wife accepted a position with a prestigious firm which much paid more than we had hoped. Upon returning home from the first day of her new career, she demanded...

A Year in the Life of... Ch. 03

by CharleyBear71 on Sep 15, 2017
Transsexuals & Crossdressers

He left Ibrahim smiling his shark grin and wandered into the bathroom trying not to let Ibrahim's obvious enjoyment get to him. The bathroom was huge with a high backed, claw foot bath set into the centre and a glass panelled shower unit which took up an entire corner of the room. He began to run water into the bath, taking the opportunity to have a mooch in...

Another Submissive Slut Ch. 05

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

By the time Mr. Lennie had arrived I was once more primped and preened. She laughed meanly as She put me through my paces while awaiting His arrival. Harping at me mercilessly that Mr. Lennie would make me suffer painfully for my inadequacies. The sudden sharp knock at the door made my heart flutter and my knees tremble with anticipation. My dickette bell ti...

Making Francesca Ch. 06

by Spango on Sep 12, 2017
Transsexuals & Crossdressers

The next morning Justin woke Frank up, "Rise and shine sleepy head. Mistress Celia has decided that you can bathe yourself now since you've been such a good girl. Now let's get cracking." With that Justin reached down and unlocked the chain from Frank's ankle that was attached to the wall. He then clipped the leash on to Frank's collar and led him into the...