Chastity Girlfriend Stories

61,196 results
Orientation
Length
Source
Infinite Scroll

Girlfriend Trouble

by lovelymess212 on May 29, 2019
Fantasy

You've been dating Sam for a long time, even thinking of popping the question sometime soon. She's perfect in every way, and its near your second anniversary. You have your own apartment together, living with each other to count on. Maybe life is far from perfect, but you have each other. Of course, sometimes life throws you a curve ball. You wake up one mor...

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You are nothing

by Macaw on Oct 27, 2016
BDSM

((Use the customizable tab to the right for this story.)) Wow, that weekend just went like a blur. After spending the past weekend with your long-distance Girlfriend Sophie, you've been left satisfied and ready to go ahead with your usual week. London station is so boring especially on a Monday morning. You're having to wait every hour for this wretched trai...

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Cruel Master Zigfield

by justincbenedict on Aug 6, 2019
BDSM

I was once Reverend Zigfield Quinn, but then I had an awareness of my true role, and I decided to give it up to be a male Master. I have some interesting clients, that is to be sure. I keep telling Hollander that he can't stop being a natural submissive. Hollander is due to wed a sweet girl, a nice little creature with a flower shop or something, and he's t...

Ballbusting/cuntbusting competition

by Cathilope on Jun 21, 2019
BDSM

Your girlfriend, megan, finally convinced you to enter the competitions shes been watching on the internet. There are multiple types of games, almost all of them involving some form of ballbusting or cuntbusting. You remember watching a few with her where the girls and guys got turns kicking each other in the crotch, and the first one to fall down had to rec...

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Who took the keys?

by sortaf on Oct 13, 2019
Fetish

I'm currently standing inside my small bedroom examining myself in the mirror hanging on the wall. The bedroom is situated with a wardrobe, a small desk for my laptop, the mirror infront of me, aswell as my holy grail the queen-sized bed taking up much of the space inside the room. As I look at myself in the mirror I can't help but look at my most apparent f...

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The Millionaire

by DanLockered on Aug 18, 2017
Fetish

The Millionaire. He was a millionaire. He was used to getting everything he wanted. He had had many beautiful girlfriends. She was a beauty and she knew it. He had to have her. He tried everything to woo her. Everything that normally worked. He sent her flowers, bought her nice gifts, took her for dinner many times. He just could not get her into bed. One...

Business Trip - Day 01

by pantywriter on Dec 16, 2019
Transgender & Crossdressers

Day 1 At four-thirty in the morning, when you and your girlfriend are both up and screaming at each other to find this and that, because you both have flights leaving the airport within ten minutes of each other, and within ten minutes from six, sex is the very last thing on your mind. We woke on time and were generally getting along well but Emma was havin...

A Changing Dynamic

by DingoSphingo on Feb 4, 2020
BDSM

I was where I was supposed to be, kneeling by the bed, when I heard the lock being turned and laughter from the main door. A warm heat of embarrassment ran through me when I realised there were two voices, just as my girlfriend had said there would be. My legs shuffled restlessly as I forgot about the aching both from my knees and from my caged, moist cock b...

Sailing Away Ch. 03

by Jasmyn_White on Jan 21, 2020
Fetish

Chapter 3 - the interview Lacy started reading a book she'd wanted to explore for a while, and I wanted a little time topside, so she allowed me to get dressed (shorts, t-shirt, lace thong underwear - can't have everything 'normal'). I sat on the foredeck for a bit, just looking at the maritime traffic, the coast, and enjoying the sun. Having had time in...

Forced To Get Dumped

by footcucknerd on Sep 16, 2017
Transsexuals & Crossdressers

James looked at himself in the mirror and shuddered, wiping another tear from his eye. He had to refrain from crying today, it would only make everything worse. Crying would ruin his make up and earn him a stern punishment before bed. Not to mention, his Mother would probably make good on her threats if he didn't perform perfectly today, and there was no way...