Ssbbw Squashing Stories

2,019 results
Orientation
Length
Source
Infinite Scroll

Good Girl's Punishment

by jays_angel on Sep 15, 2017
BDSM

I lick my lips in fear and apprehension, know I'm in trouble. Not only did I disobey a command, I also came without permission. This was unacceptable to you. Worse yet, I know you are disappointed in me. I sigh softly and lower my head, ashamed of disappointing you. Suddenly, you clamp a pair of nipple clamps on my nipples at the same time, and tightening...

Living the Dream

by Cocklockedboy on Mar 9, 2020
BDSM

This story is a fantasy, how I imagine a realistic ish lifestyle working when I meet the right woman. Sunday-Thursday The alarm goes off at 7am. Zoe gets out, wearing her short, form fitting nightie and lays out my clothes. Often, this is girly panties with Jeans and a t-shirt, but occasionally a bra, corset or silky girly slut wear is worn underneath. T...

Threesome on the Underground

by take the wife on Sep 17, 2017
Loving Wives

We were going home on the evening rush hour underground train from Leicester Square to Morden. It was hot, overcrowded with people pressed up tight barely able to move. I was penned against a glass partition by the door with Nirmala, my wife facing me. The train was slow and kept stopping, the lights flickering sometimes going off completely. Nirmala is 35...

Exquisite Torture Ch. 02

by jays_angel on Sep 13, 2017
BDSM

I lick my lips in fear and apprehension, knowing I'm in trouble. Not only did I disobey a command, but I also came without permission. This was unacceptable to you. Worse yet, I know you are disappointed in me. I sigh softly and lower my head, ashamed of disappointing you. Suddenly, you clamp a pair of nipple clamps on my nipples at the same time, and tighte...

A Stormy Night

by DreamWeaver on Sep 13, 2017
Erotic Couplings

I'll never forget the crazy look that came into my girlfriend's eyes Cathy, the night of the thunderstorm. It had been a bad one the lighting was forked all the time in the sky. The thunder boomed so fierce it made you want to cover your ears. A few times I felt that the whole world was coming to an end. Cathy and I had been playing games together on the...

My High School SSBBW Stoners Ch. 04

by completeexperience on Jun 15, 2020
Romance

As I hung up Debbie's phone, I set it on the nightstand, lay on my side on her left, and gazed at my extraordinary new girlfriend. Having lost both her cunt and ass virginity on the same day, while smoking weed heavily after having none for two months, she was exhausted and looked like she would be asleep for several hours. It was now 11:30 PM and she had sc...

The Incredible Shrinking Dude

by GratefulFred on Sep 1, 2017
Humor & Satire

(c) - GratefulFred I think it was 2 weeks ago when that funky Alien ray hit me and my life would never be the same. This is my story. I was an average sized 6' by 6" by 180 lb man, married with 2 kids and a dog. My wife had complemented me about the diet I was on, which seemed kind of strange at first, but here I was loosing weight on my fast food type die...

Certain

by WFEATHER on Sep 17, 2017
Mature

Slowly, I sank toward the floor, ultimately kneeling on the cool hard tile and feebly gripping the edge of the countertop. I could still feel my heart beating faster than normal, and even though he was no longer moving deep inside me, I could still "feel" him there, his girth forcing my body to accommodate him, his length brushing against my cervix. I could...

Bunny Licking

by Mediastar on Sep 17, 2017
BDSM

A sequel "Come into this room Boy. Just the two of us. I have a little treat for you." She said. She led him by his lead - that lovely thick controlling lead- into a small private room and closed the door behind them. She beckoned him over and he laid against Her chest, enveloping himself in her perfumed cleavage, burying his face in Her beautifully soft o...

My Girlfriend's Kinky Curse

by mr.z on Mar 3, 2021
Fetish

The nice little New England suburban area looks nice in the spring, all of the trees and bushes are getting back their leaves and the houses all match. That is except for the house coming up ahead which looks old and ratty. You remember how kids would joke about how the old lady who lives there was a real life witch. As your bike rides close to it, your fron...

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