Chastity Milking Stories

28,642 results
Orientation
Length
Source
Infinite Scroll

Julia Milks Her Colleague Ch. 02

by JohntheRapturist on Apr 23, 2018
Fetish

Julia pulled out her toolbox, grinning as it rattled across the floor. It was a huge, heavy thing, bound in faux black leather with satin nickel struts and latches. She fished out a small, heart-shaped key. The lock came open with a snicking sound. Julia was all legs and curves, a red headed and green-eyed vision of Amazonian paradise. Tommy, if he'd known...

Interracial In-Laws

by scatwoman on Sep 12, 2017
Interracial Love

My wife, Chastity, has a sister, Bella, several years her junior, who has always been on the wild side. My prim and proper wife was usually aghast at the latest information concerning her little sister's sexual exploits. It wasn't that she condemned her, she just didn't understand her. I, on the other hand was always fascinated, and frequently aroused by her...

Ms. Alexandria - Interview No. 02 Pt. 02

by gasissynora on Dec 3, 2019
Transgender & Crossdressers

This is the third part of the Ms. Alexandria series and part two of The Second Interview. I believe it will stand alone, but will make more sense if you read the earlier parts of the story, particularly Part 2a. This part starts with the last paragraph of the previous part. Ms. Alexandria: The Second Interview -- A day out. Part 2b Mistress walks up behind...

Tease Island

by justincbenedict on Sep 14, 2017
Fetish

The Early Season "The new boat comes today" M. Fulbright Penopskott commented to Dawn as he squirmed on the bed. Dawn nodded, and continued her trail of flicks against M.Fulbright's suffering shaft. Dawn leaned closer, staring intently under her platinum blonde bangs, as her pink nails painted to match her tube top poked and stroked M. Fulbright's purplis...

An Expensive Addiction Ch. 03

by NeverGuessWhatsNext on Sep 16, 2017
Transsexuals & Crossdressers

The Friday after my second encounter with English was just as eventful as I had thought it would be. My girlfriend got to town, and since we hadn't seen each other in weeks, she was hornier than hell. I picked her up from her parents house around 5 and we went straight back to my place to have sex before going to the party. A couple of months after we starte...

Thirty Seven Days

by Robert_Anthony on Sep 26, 2017
Loving Wives

The darkness was almost claustrophobic. Kneeling here for what seemed like forever had taken it's toll and I was aching to stand up, to stretch out and most of all, relax! But there was no relaxation on the cards for me tonight, that much I knew. Mistress had left me here all evening, my hands tied behind my back, my cock still locked in it's cage, just like...

Face (Sex, Power, Love) Ch. 07

by EricDumuzi on Sep 18, 2017
BDSM

My reverie slipped to the edge of sleep as I knelt patiently beside the bathtub where Gina silently reclined motionless in the steaming water. Finally, as serene as an elemental water nymph ascending with the morning mist, Gina arose. Her slim olive body glistened; her dark dense hair shimmered and rained soft droplets into the warm water. Gina didn't speak,...

Mamma Mia - En Femme

by ppeaks42 on Sep 16, 2017
Transsexuals & Crossdressers

"Ah chico, I think you already know the answer. It's making you into exactly the lover I want," Mia said as she brought a hand over to rub her cuddling stepson's chest. "It's making you into a woman like me." All the changes he'd experienced over the past weeks suddenly clicked in Tommy's head. The swelling and tenderness in his chest. The slight widening o...

Empire of Vampires 1.2.5 Brothel

by DarkMarvin_42 on Sep 28, 2020
BDSM

1.2.5 Brothel At the door Selene was received by two other women. Dressed as Dominas. Probably the mistresses running the brothel. They were also wearing tight latex clothing. But their faces were covered by masks. Mouth, nose and eyes free, but otherwise completely covered. They wore chastity belts just like Selene and in addition a steel choker. "So you...

Apocalypse Slaves Pt. 12

by AlexClayton on Feb 25, 2019
Sci-Fi & Fantasy

Part 12 - Katie * Author's Notes: Model Inspirations: Katie Thornton Nadine Jansen Pearl from the now defunct blog of "Hurting Pearl". Chapter numbering continues from previous stories just for continuity sake. * CHAPTER 114: Intake Procedures It was morning on the day after Katie's eighteenth birthday and she already knew what her future...