Diaper Sissy Stories

8,305 results
Orientation
Length
Source
Infinite Scroll

Special Girls

by chloevargas on Jul 15, 2020
Transgender & Crossdressers

We get together every Thursday at lunch. Our friend Emilio loves having us, tells us we add some glamour to the place. His little restaurant is popular enough that we're lucky to have a standing reservation for luncheon late in the week. Should one of us be absent, we buy her meal and wine anyway else Emilio glare at the empty seat. Ricki is our waitress, a...

Afro Stress Relief Ch. 07

by llts1970 on Sep 23, 2019
Transgender & Crossdressers

Author's Note: - there was a character in the previous chapter called Jane who was working in Tina's company, I realized this was too confusing because of the main character Dr Jane and so I've changed the name from Jane to Monica. I apologize for the delay in getting this chapter out and hope to have more chapters completed sooner. ***** Staci rang and sa...

Owned by my Mother-in-Law Ch. 16

by Sputnik57 on Sep 13, 2017
BDSM

As the morning of fourteenth day arrived, I cowered at Blanche's feet and kissed them again and again. In just two weeks the women had seized the element of my submissive nature and trained and broken my will completely. I was on the point of begging Blanche to allow me to see the noose again; I would rather have been despatched than go back to Cherie, her m...

A Natural Sissy Ch. 02

by harv069 on Sep 15, 2017
Transsexuals & Crossdressers

Author's note: This is a story about a woman who turns an older man into a compliant, sissified plaything. If that idea doesn't appeal to you, don't read the story. If you like the idea, read on, and don't forget to vote and leave a comment. You will need to read the previous chapter to see how we got where we are in this one. More will be added if comments...

May Ch. 01

by Jack1107 on Oct 31, 2018
Mature

Jack was in his last term at University before his finals at the end of May. Easter had been early this year. His mum, Jean, had asked her friend May if Jack could stay with her Monday to Friday for the last term as her Town House was a two-minute walk from the University. Jack had a fifty-minute drive to it then another fifty-minute drive home in the evenin...

Robin and Jimmy Olsen - Sissies Ch. 01

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

Note that this story stands separate from other stories I have posted. * "If you hunky men will excuse us for the moment, we girls have to go... powder our noses!" Robin said as she scootched around on the cushions of the private booth. Jamie rose and joined her. Their dates watched the two girls' rounded asses sway back and forth as the two sissies walked...

Dominating Sugar Daddy

by LittleDickSissy on Jul 3, 2018
Erotic Couplings

The sissy cuckold was at the ATM withdrawing cash for his Mistress. He needed cash for her nails, her new dinner attire, and makeup. As he made his withdrawal his little dick dripped precum in his purple lace panties. He always got turned on every time his Mistress provided strict instructions to him, and of course whenever she played without him. "Now tell...

A New Toy

by keptsissy on Sep 13, 2017
Fetish

I love this view. It never gets old. I watch the top of his head. I see his tasseled brown hair as his mouth moves back and forth on cock. I see the curve of his perfectly rounded baby smooth cheeks, ever so slightly spread by way he arches his back, his butt perched up on top of his heels, his toes dug into the carpet as he kneels in front of me. I hear him...

A Missy Affair

by Stillherer on Sep 16, 2017
Transsexuals & Crossdressers

I knew I was being careful. I thought I was being clever. But I never thought I could be caught in such incriminating circumstances by of all people my sister-in-laws husbands parents. I was playing the good brother-in-law by doing a bunch of minor home reno's for my wife's sister and her husband. To my delight they trusted me implicitly and left me alone in...

Doing Three Ch. 2

by Royal_Prince on Sep 12, 2017
Loving Wives

Chapter 2: Submission I had been lying on the couch most of the night wondering where the night had gone wrong. At first fantasy after fantasy was coming true. I was able to watch my lovely girlfriend make love to the beautiful sex goddess Mary and then watch her explode into an orgasmic frenzy on Mary’s husband’s 8-inch cock. Both Angel and I had fantasi...