Butt Plug School Stories

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Orientation
Length
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Infinite Scroll

Party Turned Training Session

by rosesubslut on Sep 13, 2017
BDSM

It all began with Him telling me we were having a party for the Superbowl. To most that would seem like nothing out of the ordinary, but to me, it made my mind race. Maybe I should back up a bit and explain the relationship so you might understand. You see, He is my Dominant and I am his anal submissive slut. That means that He directs what i do daily and...

Cynthia's Submission Ch. 08

by GettingItDone on Sep 12, 2017
Anal

Small note, I have realized that the last name of the lead character has changed a few times throughout the chapters. To correct this error and to keep things consistent, Cynthia's last name from here on out will be what it was originally stated; Miss Watts. Also, I would like to apologize for the long delay for this part to the story; I just have not been a...

Sandra is Inquisitive

by EnjoyBoth on Mar 27, 2019
Group Sex

I pulled out of the parking lot at the office in the dark. It was getting dark quickly as December began to take hold. I made my way to the tavern. It was time for Happy Hour that cold Wednesday evening. My cell phone rang as I pulled into the tavern's parking lot. I hit the speaker on the phone without looking at the number and immediately, Jennifer asked,...

Kimmy the T-girl

by sissy_in_denial on Sep 16, 2017
Transsexuals & Crossdressers

Introduction: Hello. My girly name is Kim, but in my every day life, I am known as Ken. I am 5"5, 135 lbs. I'm eighteen years old, and this story begins on the last day of school before spring break. I have been a closet cross dresser for the past two years. I started off from stealing my sister's panties and bras and wearing them when I was home, alone, an...

Finding the Perfect Fit Pt. 10

by Joshana on Jan 6, 2020
Transgender & Crossdressers

Sunday Morning A text from Jamie Saturday night asked if we could go for breakfast the next morning and I agreed, stuck in the cooler at work fighting a tower of Dr. Pepper that was threatening to fall over any second. Of course it did and I had to mop the mess up, hoping a meteor was heading for whoever had fucked up such a simple job of stacking shit! I...

Dahska's Trial Ch. 06

by the giant peach on Sep 3, 2017
Fetish

Dahska laid sleeping, dreaming about her new life. When the sounds of fighting woke her. "Clank tink swish tink vermboom." "Fuck." "Ahg oh fuck." Dahska ran down the spiral staircase that led to the courtyard. She burst out of the door and into the battle joining Sam. "Need some help." She smiled at him. "Sorry we woke you. These raiders try to get our...

The Journey Pt. 03

by MissYellowPanties on Sep 14, 2017
Transsexuals & Crossdressers

Training It was an unusual feeling walking down the corridor, my sissyclit was hard with excitement and I had not yet adjusted to the feeling of the butt plug placed firmly in my boypussy. I still tried to move in a ladylike fashion, but the strange sensation was overwhelming and I stumbled suddenly out of time with Mistress Anna's gait. Mistress Anna...

A Proper Young Woman's Guide to Anal Etiquette Ch. 09

by lordodie on Sep 18, 2017
Anal

Disclaimer: The following is a work of pure sexual fantasy and is intended for adult audiences ONLY. If you are under the age of 18, please stop reading NOW and go tell your parent and/or guardian that you need stricter internet supervision. Any physical resemblance to a real person that any fictional character herein may bear is probably intentional and is...

Adventures with Lisa

by Storm62 on Sep 15, 2017
BDSM

"Can I come round? I've got a surprise for you." It was my sister's friend Lisa, recently turned eighteen, and now my girlfriend. She was slim, about medium height, with a gorgeous figure that had filled out in the past few months to something like 32-20-32. Her eyes were blue and her curly hair was that colour that wasn't blonde and wasn't brunette. I'd not...

Anal Punishment Ch. 01

by VictoriaCollins on Sep 12, 2017
BDSM

It is early on a Saturday morning, and I'm already showered and dressed for the day. My husband is still asleep, curled on his side. After all this time together the sight of him still makes my heart beat a little bit faster. I want to lean over and kiss his forehead. Instead I steel myself for the ordeal ahead of both of us. "GET UP!" I scream as I tear th...