Chastity Tranny Stories

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The Advice Columnist

by colonellunchmeat on Sep 16, 2017
Fetish

Dear Debbie: What is your opinion on your submissive's RIGHT to occasionally kiss your boobs? My husband is totally hot for my full, pink 36D melons, but since he became my slave,I gradually weaned him off of them. Part of the problem is, I'm not as attracted to Joel as I used to be, he's kind of chubby now, and having his hands groping me when he brushes...

Letter from Tanglewood Springs

by justincbenedict on Jan 1, 2019
BDSM

Dear Shoeblossom, How can I start this? I was raised to be a spoiled brat, and I always seemed to get what I wanted when I had tantrums, even into adulthood. My parents always let me win when we played games, and I learned how to cheat in school and subtly sabotage other players in athletics, such as kneeing in basketball, to make me a star academically a...

Sissy's Decline into a Slut Pt. 06

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Eight: Moving Along with my Sissy Maid Life and lots of Sissy Slutty Sex too. [Beep, beep, beep] My alarm clock goes off and a struggle to wake up. It is 7:00am and I come around to realize I'm in my sissy bedroom in my Master's house. I get up quickly now, in my white satin bra and panty with white satin full slip, this is my sleeping lingerie. I t...

The Sexy Domme Next Door Ch. 03

by rickiee_2002 on Sep 19, 2017
BDSM

Ch. 3 Carissa takes the initiative "Mr. Lewis, you're niece is here to see you" announced my secretary. I started thinking ... my niece ... my niece never visited me here before. I thought it was kind of odd. "Send her in" I replied As I looked up upon hearing the door knob turning, I saw Miss Carissa enter my office with a smirk on her face. "Hi Uncle...

Isaac Moves in New Circles

by justincbenedict on Oct 22, 2019
BDSM

Pleziewska "Plum" Kronislaw watched with fascination as her cousin Isaac kind of danced naked, his legs apart as his uh, paramour, Mesquite DiMarco used Isaac's Zippo lighter- ...The flame hovering just under Isaac's engorged testicles to distract him as he masturbated. "I hope this doesn't make you feel terribly uncomfortable, Plummy" Mesquite said, smili...

The Librarian Ch. 03

by MicheleNylons on Sep 13, 2017
Transsexuals & Crossdressers

Part Three - Return of the Ice Princess They stayed two days in the motel while Sarah got well. In between her bouts of nausea they developed a strategy. Randy fed her Chinese food and Coke; two staples that she seemed to be able to keep down. "We need a back story. Tina isn't going to believe that I just turned up out of the blue and want to work in the p...

Transforming Brent Pt. 02

by sissymissyct on Jul 10, 2019
Loving Wives

Kept in Loving Wives to annoy the tiny dicked anonymous reviewers that love to trash everything they read (after they wank to it). *** I woke up Sunday morning with a painful erection in my chastity and the pumps still attached to my breasts. I reached down trying to find a way to ease the pain in my penis. Nothing seemed to help. Maybe Wendy will be up so...

Sleeping Beauties Ch. 07

by MicheleNylons on Dec 16, 2019
Transgender & Crossdressers

Chapter Seven -- Heads or Tales Penelope, Silvia and Bradley arrived at Ellen Wright's house to find the scene of crime team and medical examiner in attendance. They put on the Tyvek over-boots, hair coverings and latex gloves and entered the house being careful to tread only on the matting laid down by the CSI techs. Bob Tanner met them at the door to the...

Been Caught Cheating Ch. 02

by rebeldoll on Sep 15, 2017
Transsexuals & Crossdressers

I awoke in the morning to voices. It was Angela and her sister Heather! I could here them in the next room talking, but couldn't make out the words. Everything was still dark though. And I was still bound to the bed, and gagged. I had stayed like that all nightlong. Trying to move, I also found that at some point, my ankles were also bounds together. And the...

Smoking Blues

by sissymissyct on Mar 26, 2019
BDSM

"Hey Bren," called my assistant Sarah. The home office called while you were out smoking. You Better call Mr. C back. He didn't sound happy!" "Okay, thanks dear. I will call him back straight away," I replied as I headed to my office. As I was opening my door Sarah continued. "You know, you really have been taking a lot of smoke breaks lately. We are all co...