Tiffany wearing items from Hustler’s BDSM line!

“So never judge a book by its cover”

Tiffany came back to town. She was all riled up and ready to play. Thoroughly excited to see me, the slut called and texted several times before our session. Because she was so frisky, I knew I had to get her in line. I planned an elaborate homework assignment.

We opted for a split session, with shopping at the San Jose’s Hustler Hollywood store on Thursday evening followed by a two hour session Friday morning. 

Before shopping, she took Uber to my place and I locked her in chastity and put her in pink panties. Then, we hopped in my car and went to the store. I wanted to look at anal toys, and she wanted slutty clothes. Both are available there. She came away with a few nice things. I came away with ideas…

After Hustler, I dropped her off at her hotel with a bag of items and a homework assignment. The bag contained a bottle of water and a bar of chocolate (for refreshment) anal trainer, lube, rubbers, paper and clothespins.

She was told to make good videos for me because she would be graded. Additional grades will come from the feedback of this blog, so please comment.

Her instructions:

1.  Insert condom-clad butt plug in butt.

2. Sit at the table with butt plug in and write 25 times “I am a slut, with a plug in my butt.”  Use properspelling and punctuation. Points will be deducted if not followed.

We settled in to watch the videos. I have to say, they made me blush a

Love put me wise to her love in disguise
She had the body of a Venus, Lord, imagine my surprise!

little, especially the one where she rode the anal trainer. This was a funny sensation since Mistress J sees men in the depths of depravity every day. But I liked it. Up to the playroom we went, and things got really dirty there…

I keep a small wardrobe for her here. She’s the only one who can wear such small clothes. I put her in her denim dress and was shocked that her chastity device created unsightly and unfeminine bulges.

I wanted to tease her as much as I could, so I flipped her on her back and played with her boy pussy. I opened her up nice and wide then got out my Liberator and Dick-on-a-stick. She rode that thing with her arms bound behind her back. That dirty whore! She was moaning and groaning and begging to let me out of her cage. Pre-cum dripped through the crevices of the chastity cage leaving a pool on the tip of her clit. Her pussy was soaking wet.

More bondage, more butt play, finally a release from the cage. She endured as much edging as she could, then begged to cum. I denied her request and the bitch was so horny, her cum slipped out and I quickly captured it in a Dixie cup and forced her to swallow. She’s good at that.