Crossdressers Chastity Stories

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Forced To Get Dumped

by footcucknerd on Sep 16, 2017
Transsexuals & Crossdressers

James looked at himself in the mirror and shuddered, wiping another tear from his eye. He had to refrain from crying today, it would only make everything worse. Crying would ruin his make up and earn him a stern punishment before bed. Not to mention, his Mother would probably make good on her threats if he didn't perform perfectly today, and there was no way...

My Friday Night

by honey28 on Sep 26, 2017
Transsexuals & Crossdressers

A true story, though the names have been changed to protect the not-so-innocent... *** "Why don't you get dressed?" I suggest, knowing that he had been waiting for me to tell him to change. Wanting it. Earlier, as we settled into our room, he had stripped down to his shorts so he could put on the chastity device, and gave me the key. We lay on the bed f...

Life and Time of Lady Vargos Ch. 11

by rik581 on May 7, 2019
Transgender & Crossdressers

Martin reflected on the previous nights event. He hugged his pillow tightly to himself as he mentally relived the humiliation that naturally came with taking the Vow publicly, even for women. It had lived up to it's reputation. It was the most degrading and demeaning act of so called love a human being could experience. It would soon be time to get out of...

Lulu Exposed

by lulu_dools on Apr 25, 2018
Transsexuals & Crossdressers

My name is Louis and i'm 35 years old. I am just a normal guy with an average build and really long brown curly hair. I like a beer on the weekends when i am watching the footy, used to smoke weed but have grown out of that except for the odd occasion. Every once in a while i also like to have a line of speed and this is where my problem started. You see, w...

My Wedding & Living as a Wife

by TammyPanty on Jan 7, 2018
Transsexuals & Crossdressers

My wedding and ultimate goal of being a wife Over the next eight weeks Norm and I dated at least nine more times and enjoyed full penetration sexual intercourse at least on five of those occasions. During our post coital hugging and kissing on our ninth date Norm politely asked me in a calm and soothing voice if I would consider moving in with him and livi...

The Roommate Pt. 07 - Miranda

by ValoryG on Sep 16, 2017
Transsexuals & Crossdressers

The next day, when Josh returned home from teaching college students (who were only around six years younger than him), Miranda met him at the door. She seemed in a fine exuberant mood and gave him a smile. Sometimes he didn't know which personality he'd find - the friendly, mother-like woman who helped him become Lori, or the controlling figure who could...

A Trip to Remember Ch. 01

by marykay9 on Sep 16, 2017
Transsexuals & Crossdressers

I live in Los Angeles and don't get much of a chance to practice my hobby of cross dressing. Once per year however, my company sends me to an industrial convention and I take full advantage of the opportunity. This year I was to travel to San Antonio, Texas, to attend a conference at a large hotel located on the River Walk. I packed two bags, one with my b...

Ms. Alexandria - Interview No. 02 Pt. 01

by gasissynora on Nov 4, 2019
Transgender & Crossdressers

This is the second part of the Ms. Alexandria series. I believe it will stand alone, but will make more sense if you read the first part of the story, "Ms. Alexandria: The Interview." * Ms. Alexandria: The Second Interview -- A day out. Part 1 I get home from the interview, feeling that it went very well. I am also extremely horny so I strip down to my li...

Sissy Maid to Be... Ch. 01

by missjennymaid on Sep 5, 2018
Transsexuals & Crossdressers

Prolog I have always had the desire to dress like a girl. It started at a young age when my mother used to have me try on dresses to "see if they would fit my cousin." As I got older I still had the desire and it got strong enough that I started going out in public in college. I was lucky enough to meet and marry a woman who was accepting of my "hobby". Liz...

A Week End with Mistress Pt. 01

by gasissynora on Oct 16, 2018
Transgender & Crossdressers

Dear readers this is my first story and I hope you enjoy it. Your comments and suggests will be most helpful. I am planning on continuing the story if the feedback is positive. This story is based in part on facts and part on fiction. I will leave it to the reader to decide which is which. ***** We had just finished dinner and I was in the den getting rea...