Sissy Truth Or Dare Stories

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XChange Seminar, X-change, X Change Ch. 02

by Grabenork on Feb 6, 2018
Transsexuals & Crossdressers

"Good morning, everyone! I am Dr. Welcott, and I am very happy to welcome you to X-Change Technologies, Inc. You are all here because you attended one of our X-Change Seminars run by Dr. Brewer at the Comstock Institute. He reports that you all participated in the seminar enthusiastically and then signed a list to volunteer to become future demonstrators at...

The Darkness

by littlemissnaughtygal on Sep 12, 2017
BDSM

Kim was always the good girl, even when Darnell and Kim were into their Domination nights, Kim always submitted to Darnell, she had worked with him for so long little by little trying to pull his dominant side out in him, she knew it was there, she could see it in his eyes, and she had seen it in her dreams so many times. Each night they did this, he becam...

His Best Friend or His Worst Enemy

by Omega12 on Apr 3, 2019
Loving Wives

They had been friends all through college. Frank and Billie had shared a dorm room for all four years. Billie sometimes got annoyed with Frank because he was kind of a braggart and full of himself, but still he was kind of fun to be around. If there was one thing that annoyed Billie more than anything else was Frank always bragging about the girls he had lai...

Outed and Married Ch. 03

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

When I entered the room with their drinks on the tray I was carrying I thought I would be pleasing to my husband. I made sure that my skirt was properly adjusted the way he likes me to wear skirts in the house. He insists that my rear not be covered below my tight little hole, insists that he have instant access to it if he wants to use it for his pleasure....

I Learned My Lesson Well Ch. 03

by Angelscuck on Sep 2, 2017
Exhibitionist & Voyeur

Well the weekend had arrived. My Fiancé, Angel, had given me a complete makeover at the salon. I looked ridiculous in my maid's costume with full makeup, heels, stockings, garter belt and leach with collar. She looked amazing with her slutty makeup, hair worn up and completely naked under her trench coat. We were on our way to her gangbang. Her black maste...

Truth or Dare Ch. 03: Take Me Tom

by RebeccaCherie on Sep 16, 2017
Transsexuals & Crossdressers

Cupping his balls in my left hand I move position to take my man in my mouth. My Mother always told my older sister that it is a woman's role, her duty to please her man, to be there for him as needed, when needed. I wonder if my sister is as compliant, as obliging with her Husband of 6 months as I wish to be for Tom. I could be a very obliging young lady in...

Sissy Slut Ch. 02

by Scribler on Sep 13, 2017
Transsexuals & Crossdressers

At first I was a little pissed she just discarded me like that so easily, but I quickly got over it, as I was now free. Thankfully there were no other houses nearby that I had to worry about being seen in all my naked glory. It took me a few minutes before I was able to drive away, as I had to get dressed first. I kept looking back at the house, as I wanted...

Caretaker Joe

by CarrieQ on Dec 2, 2019
Transgender & Crossdressers

It was my first time living on my own. I was 18, and enrolled at a college to study art and photography, in a town far from home, in fact close to London. I took a room in a hostel, popular with students. It was halfway down an ill-lit corridor, and no one seemed to bother me, which suited me just fine; I liked the solitude. I was confused about my gender i...

Casey's Submissive Journey Pt. 02

by corduroysissy on Dec 14, 2017
BDSM

Debbie's eyes bulged when he looked up at Angelina, and his best friend smiled back at him. "This is my Angie, Debbie, he wanted to watch you cream his jeans." Looking through the make-up and wig he could barely make out the face of his young buddy. Casey was blown away by how good Jamie looked as a girl, he was pretty as all hell. The make-up looked perf...

The Lady Next Door

by stories55 on Mar 6, 2018
Mature

I moved into a new suburban neighborhood. I'm not the real social type so I didn't go out of my way to meet the neighbors. I'm in my mid 50's and I noticed that I did have a lady living next door that was probably about my age, but she could have been a little older. I saw the young children that visited the house during the holidays, so she could have been...