Shrinking Chastity Stories

14,443 results
Orientation
Length
Source
Infinite Scroll

A Cuckold is Seduced Ch. 02

by wants2bsub on Sep 25, 2017
Loving Wives

This is part two of a story involving cuckolding and male power exchange. Please read no further if this offends you. --------- I was on my knees, helping my wife Kelli attach her garter belt to her stockings. I leaned forward and planted on a kiss on her newly trimmed pussy. "Now, now," she said, "Let's save that for Ron." Based on the email that he sen...

Cyclists

by LC10 on Aug 19, 2017
Erotic Couplings

She liked to be in control and wanted to be able to see where they were going, or so she told him, so she was pleased when he let her ride on the front saddle. The front saddle was altogether nicer than the back one. It was a thin racing saddle with a smoothly pointed end canted slightly upwards which made pleasurable contact with her crotch which was furthe...

White Boi Learns his Place Ch. 03

by sissyashley4bbc on Jul 10, 2018
Transsexuals & Crossdressers

After the group decided we should go to our pool, Emily came up to me and told me she had a bathing suit I could borrow. Daddy told me to go get changed with her, and the guys would start making drinks and rolling joints to take outside. I guess he didn't need to change really, all he has on was athletic shorts that would dry quickly. I followed Emily upst...

Letter From Scranton

by justincbenedict on Sep 14, 2020
BDSM

Dear Shoeblossom I had a sister, Huxley, ("Hubert and Huxley, so cute") and we lived at home during our university years, as Pop was bursar at the local college, so we went for free. Huxley had a best friend, Tamsin, who was cute but chubby, and I teased her about it, and one day Tam pulled my pants down when no one was around, and gave me a spanking--me,...

For Her Amusement Ch. 01

by jsx730 on Sep 25, 2017
BDSM

Preface This story is loosely based around the life of my wife and I, along with a married couple that we are friends with. The characters are based on real people, but the events of the story are only fantasy. We're all around 30, give or take a few years. In the past, my wife and I have explored swinging, power exchange, and a long list of kinks. At the t...

Miles's Counseling

by justincbenedict on Sep 16, 2017
BDSM

My chastity tube hangs heavily between my legs. It resembles a water faucet, and looks a little odd. Gretchen used to have me in a plastic thing, but she felt that I was too disrespectful in having big erections... And the tube makes it quite cramped! Really, it is. When I get a hard on, it's quickly contained. Then I feel this unpleasant squeezing fro...

The Office Boy Ch. 09

by Aussie Worm on Sep 25, 2017
BDSM

The months and weeks passed quickly and Katrina and my wedding were only a few days away. Everything had been planned and organised weeks ago and I was told there were only a few last things to do and nothing that concerned me. Natasha, Jessica and their slaves had arrived early this morning and already had plans to go out and about to experience the city....

Always Read Before You Sign Ch. 06

by Reaver90 on Apr 21, 2020
Transgender & Crossdressers

A week had passed since Paula took Samantha's virginity. Since then Samantha had been phoning the council and telling them that she was moving out of her apartment. She had also gone to the bank to have Paula's name added to her bank account. Samantha even had begun the process of getting her name changed from Sam Watson to Samantha Watson. Samantha also ha...

Carol's Gifts

by Belongs2Beth on Sep 16, 2017
BDSM

Authors note: This is the third story featuring characters introduced in "Carol's Christmas." In this installment Carol give's Jack his Christmas gift one night late with the help of Irena, "Marcia" and several well hung younger men. The sex action in this story is unrestrained, and since the tags are at the bottom of the page, I will issue the following mil...

Daniel and Jamie's Romantic Night Ch. 02

by lockedinsteel on Apr 17, 2019
Group Sex

Daniel woke up and realized that someone warm was pressed into his back, their arm draped over his side, their face nuzzled into his neck. As he opened his eyes he saw the clock and realized that it was later than usual, almost 10am. The events of the previous night came flooding back as his mind shook off the tendrils of sleep. He remembered submitting to...