Sydney's anal training

Sydney walked into the room where her anal class would be held with a nervous smile. She was greeted by a brunette in a black leather corset and matching boots. A look of confusion came to the submissive teen's face when she looked around and saw no one else.

"Am I early?" she asked.

"No, you're on time. This class is usually used as a form of punishment and you are my one and only student today."

"Oh, I figured there would be a few others."

"Not today i'm afraid now please strip and go face down and ass up on the bondage table."

"Yes Ma'am," Sydney said before quickly stripping and getting on to the table.

"Before we move on I am Mistress Andrea and..." the brunette began before pausing once she saw Sydney's red and bruised ass.

"Looks like this class is part of your punishment," Andrea said as she ran her hand over Sydney's ass causing Sydney to wince in pain.

"No Mistress Andrea. I was spanked for not telling my master I struggle with anal when I want to be a no limit ****."

"I see," Andrea said as she began to lube up the smallest anal plug that she had retrieved along with a strap-on and some lube. "This class works by starting with the smallest plug and working our way up to the largest. After the largest is removed, I fuck you with a strap-on."

"Okay," Sydney said with a slight gasp as she felt cold lube run down the crack of her ass. Soon after she groaned slightly as Andrea pressed the smallest of the plugs against Sydney's tight puckered hole and the plug slid into place. After half an hour the plug was pulled out, and replaced with the next biggest plug.

Two hours later, Andrea removed the current plug and set it aside. "You've done well so far but this is the largest plug are you ready?"

"Yes Mistress Andrea," Sydney answered nervously.

"Okay, here it comes," Andrea said as she began to press it against Sydney's asshole. "Relax," she added as she placed her hand on the small of Sydney's back when the plug met with resistance and Sydney groaned loudly and began to kick her legs wildly. Sydney continued to groan as Andrea slowly and gently worked the plug into her ass until she felt the base of the plug rest against her ass cheeks. "Good girl Sydney," Andrea praised.

"God my ass feels so full," she thought to herself she took deep breaths trying to get use the the feeling of her ass stretching out to accommodate the plug in her ass. After nearly half an hour Andrea slowly pulled the plug from Sydney's ass.

"Time for your ass fucking, this strap-on is smaller than the last plug and since you've been such a good girl, I'm going to use a vibrator on your pussy."

"Thank you Mistress Andrea," Sydney said as she felt the strap-on press against her hole.

"Remember to tell me when you're going to cum."

"Yes Mistress Andrea," Sydney half moaned and half whined as Andrea began pushing her hips forward, sliding the dildo into her ass slowly until her hips rested against Sydney's ass. Once the strap-on was completely in the young brunette she began to rock her hips back and forth at a slow steady pace keeping a grip on her left hip with one hand and gently pressing a vibrator set on medium power against the girl's pussy.

"That's a good girl," Andrea said proudly when she felt all resistance in Sydney's ass end and she began to moan loudly in pleasure. Slowly over the next few minutes Andrea increased the pace of her fucking,

"Mistress, I'm going to cum!"

Without warning Andrea pulled the vibrator away and began to fuck Sydney at a blistering pace. "Come on, cum for me!"

"Oh God my ass! Oh fuck Mistress I'm cumming!"

Carson sat in his suite with the twins and Ellie discussing the upcoming **** auction. The twins had decided to be auctioned together and wear pink collars, marking them as available for women. The two felt that it was inappropriate for them to be with another man while in a relationship with Carson. Ellie on the other hand had chosen to wear a blue collar as she didn't feel comfortable being with another woman unless it was one of her sisters or Sydney.

Carson smiled when he heard a knock at the door. He made his way over and when he opened it he was greeted by a tall blonde maid in one hand she carried a sealed envelope. Draped over her other arm were four garment bags.

"The report on your submissive and your tux and gowns for the evening," the maid said.

"Thank you," Carson said taking the maid's load from her. "That will be all."

"Yes sir, have a pleasant day," the maid said as she curtsied and went on her way.

Carson sat on the bed and opened the envelope.

Mister Henning,

In keeping with Paradise Club policy, this letter is to inform you of your submissive Sydney's performance in Anal class. While she struggles occasionally to relax and allow easy access, she does want to improve and does not complain about her ass being stretched.

I recommend having her participate in tonight's auction, and placing a red X on her pussy making it off limits to potential buyers.

Sincerely,

Mistress Andrea Watson

"That sounds like a wonderful idea," Carson said with a smile.

Next up the **** auction. Will we see the ball leading up to the auction, or go right to the viewing and bidding? Answer in comments.

A) The ball

B) Straight to the auction