Chastity Girlfriend Stories

61,196 results
Orientation
Length
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Infinite Scroll

Kate's Heavenly Hell Ch. 05

by Duke567 on Sep 16, 2017
Fetish

Finally Thursday came. Kate would soon be home with the key! Thank God! I don't know how much more I could take without going crazy! When Kate came in the door, she was wearing the key around her neck on a gold chain. As I started stripping my clothes off for my long awaited relies Kate whispered "I asked Alexa to come over tomorrow." "What? What are yo...

Black MILF Femdom For Black Guys

by Samuelx on Aug 18, 2017
Fetish

Salutations, my name is Ginette Ambrose, and I'm a fifty-two-year-old African-American woman living in the City of Brockton, Massachusetts. One of the most diverse towns in all of New England, I swear. I'm five-foot-nine, chubby but still lovely in a wholesome kind of way, with dark brown skin and long Black hair. Thick Black mama with big tits and a big rou...

The Pump House

by AlinaX on May 11, 2020
Fetish

Inspired by an idea by enigma3 in the Forum. * They say size doesn't matter, but when you are - whether by length or girth - within the smallest five percent of the population, it's difficult not to feel self-conscious about it. It's difficult to talk to women without imagining their horror, their amusement, their mockery, their contempt. Easier to avoid r...

The Contest

by justincbenedict on Sep 13, 2017
BDSM

Benny Price looked a bit discomfited as he entered the Marathon room. There were four guys, kneeling on pillows... Yes, naked as the day they were born, jerking their dicks VEERY slowly. They looked exhausted, and Benny looked at Nora, his beautiful fiancée, and wondered what the hell he was doing here. "You were so busy with work, you've missed the la...

Letter from Newark

by justincbenedict on Jan 8, 2019
BDSM

Dear Shoeblossom, I am just an ex-cocktail waitress who married a troubled but worthwhile guy. Mom always told me to find someone classy like a dentist or a Buick dealer. "Mariah, it's as easy to fall in love with a rich guy as a broke guy." But I fell for Raymond Withers, Jr. hard, and I married him right before he went to Vietnam. Still, as in all marria...

Pathetic

by Fappy_McFap_Fap on Mar 28, 2019
Cheating Spouses

There was no easy way to say it, I thought, peering down into my boxers. My cock was small. It had always been small. When I was growing up, I'd always assumed that it would grow and reflect the man I believed I was inside. But puberty came and went, I grew taller, my twin sister, Ruby's tits grew larger, my friends' voices deepened and yet, I remained with...

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A Sissy is Born Ch. 02

by gtanya on Oct 13, 2020
Transgender & Crossdressers

Author's note: This story is the second chapter of "A sissy is born" series. Please note that it is a very slow build up and if you are looking for some hardcore sex right away, it is not for you. Please leave your comments to help me improve. It was a fairly uncomfortable couple of hours of the train ride with the constant staring of Mr. King. His gaze som...

Online Cuckold Looking for Love Ch. 02

by subboy129 on Aug 31, 2017
Fetish

The next morning I woke up and found Goddess was out of bed. I was happy that she let me sleep after a night of fun. I pulled the sheets off me and noticed my cock cage was back on me. I was fine with it as I love being in chastity. I came out into the living room and noticed Goddess was sitting on the couch watching TV. I went over and said hello and gave h...

Dirty Weekend with Cuckoldress

by footslave85 on Mar 6, 2018
Loving Wives

I had been with my beautiful girlfriend for about a year and we had a very interesting relationship. Of course I worshiped her as the gorgeous, dominant woman she was and we did lots of things together as a couple. But, I was her cuckold, giving her the freedom to have sex with other men. One night stands, regular lovers and sometimes, old flings. This par...

My Sissy Cuckold Life

by SissyCuckMike on Jan 2, 2021
Fetish

Hello everyone, my name is Mike and i am now a sissy cuckold. If you don't know what a sissy or a cuckold is i will explain, a sissy is like a cross-dresser but usually dresses up in pink frilly women's clothing and cuckolding is similar to a hotwifing where she goes out on dates and fucks other men without her husband/boyfriend around but with cuckolding it...

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