Diaper Pegging Stories

3,032 results
Orientation
Length
Source
Infinite Scroll

Ultimate Sissy Weekend Ch. 02

by SissyTwinkleToes on Dec 24, 2019
Transgender & Crossdressers

It had taken a good half an hour via taxi to get to this postbox, across the city from Sissy Susie's home. All so Sissy Susie could post five keys to herself, containing the keys that keep her and Sissy Tinkerbell locked in their ridiculous sissy dresses, locked in handcuffs to each other, and locked in the clitty cages that have kept them chaste for the las...

The Diaper Spa Pt. 10

by clazzjoud on Sep 10, 2018
Fetish

Angela wasn't exactly thrilled about the idea of seeing Ashley on Monday. Their encounter at Margaret's had been stressing her out all weekend. She kept thinking about what she should and shouldn't have said. Though Judith was around to provide happy distractions, it still weighed heavily. She approached the chart for the day with caution. Sure enough, she...

What Did You Expect?

by LaDonnicciola on Oct 15, 2017
Fetish

Sitting handcuffed to a chair wearing nothing but a thick, cute, pink princess diaper watching my wife of four years sucking a much thicker and longer cock than mine was not how I planned to spend last Wednesday night. And yet, that's exactly how it turned out. As soon as we finished dinner - which I, as always, cooked - Elaine told me she wanted to try some...

Denise Pt. 01

by rewriterewrite on Sep 26, 2017
Fetish

Denise tapped her foot nervously. Damn it! Why did she have to pee so badly? It hadn't been that long since she had gone, at the store twenty minutes ago, but now she was stuck in the middle of traffic. This did seem to be a problem of hers. It wouldn't be the first time she had made the mistake of drinking coffee on an empty stomach. It always went right...

Space Camp Ch. 04

by kcunningh on Sep 14, 2017
Fetish

Disclaimer: All persons in this story are above the age of 18. It should be assumed that all sexual experiences are between people above the age of 18. This story includes diaper wearing as a sexual fetish, diaper wetting and sex between consensual parties all above the age of 18. Back in Kylie's room, the rest of the campers weren't sure what to do ne...

The Training of Sissy Paula Ch. 5

by submissive~pet~ on Sep 14, 2017
Fetish

After the fuckings I had gotten from Max my asshole was so stretched, I had to wear diapers all the time. Mistress Carolyn used this to her advantage. She had a few men that liked sissy babies. The men would bring me all sorts of little sissy clothes. Dress me up and have me nurse their cocks as if they were bottles of milk. One day a new man showed up, he w...

Kinky Awakening Ch. 01

by rj1774 on Oct 13, 2017
Fetish

FYI, this story features CEI and pegging if you are uncomfortable with that click to next story. ***** My husband is a high powered attorney which allows me the luxury to stay home, volunteer, and keep up my hobbies. This made what I found even more concerning at first. He left in a hurry one morning and forgot to shut down his laptop. Not thinking anythin...

Saudi MILF & Black Scholar Ch. 10

by Samuelx on Sep 16, 2017
Interracial Love

Can a guy develop prostate issues as a result of too much strap-on sex? I'm afraid to ask my doctor this question. My name is Tyrone Ferguson, and I'm a young African-American man living in the City of Ottawa, Ontario. The reason why I've got this burning question on my mind is because my gorgeous, sinfully sexy Saudi Arabian girlfriend Amina Alzahrani has b...

Mommy Eve

by Subtext on Sep 16, 2017
Fetish

When Bobby arrived and knocked on the door of the well-kept house, his heart was pounding in his throat. He had searched a long time for the right caregiver and he was nervous that the whole thing was a huge mistake. But the woman's manner and voice on the phone had been so comforting that he had decided to brave the long drive and give her service a try....

Peek-a-Boo

by morningchica on Aug 18, 2017
Fetish

Veronica's breasts were beginning to let down their milk, and she was worried it would show through her t-shirt. She was completing the last leg of a jog in the park, and the thin bra she had worn allowed her breasts to bounce and move easily as she ran. The excess movement and their fullness made Veronica feel eager to express them. She imagined how good it...