Dude Looks Like a Lady.

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:

Record this:

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.
 
3. Put on stockings and panties and clothes pins on nipples. Dance around to “Dude looks like a lady” by Aerosmith. Grading will be on sexiness of the dance and enthusiasm.
 
4. To the song “Hurts so good” by John Mellencamp, set dildo on the bathtub rim and slide up and down on it.
 
5. Unlock cage and edge yourself 10x. Grading will be on how close you can get to the edge without cumming. If you cum, you must eat it. You will receive a failing grade if you cum.
 
6. Lock yourself back up and sleep with key around neck.
 
Don’t record this:
 
7. Give yourself an enema before arriving at my house.
 
The next morning Tiff arrived bright eyed and bushy tailed, wearing a bejeweled butt plug, chastity device and her fancy lingerie under her unassuming tech worker clothes.
 
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…
 
She admitted the homework assignments got her even deeper in to submissive heads pace, and made her super horny. She admitted it was hard not to cum during the edging assignment, and I saw this struggle on her face in the video,
 
Tiffany has this to say about the homework: “The homework assignments were a great way to feel my Mistress’ control outside of her room”
 
Slut Tiffany has a nice, petite body. (She can wear my shoes.) I made her strut around the room flaunting her sexuality.
 
Tiffany was really horny. She hadn’t cum for a week and she kept begging to be let out of her cage. She was subsequently punished for being annoying.
 
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.
 
Tiffany has become quite the mouth and ass slut. She also enjoys bondage. I bound her arms behind her back and made her suck big cock. She gagged and drooled.
 
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.
 
 I stripped off her dress and gave her a sissy lip gag. This resulted in more drool. She sucked on her favorite Popsicle until tears came out of her eyes and snot dripped out her nose. Down on all fours, she got fucked with the very thing she just ate!  Nasty.
 
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. 
 
I know she will return, and I will have some homework ready!
 

Intrigued? Contact me.

Mistress J Studios is a sex positive studio that provides a safe place for personal expression. Nude male photography, male and female submission, cross dressing and gender exploration are welcomed and encouraged here.

My email is mistressjstudios@gmail.com.  I am in San Jose, California.  I look forward to hearing from you.

 
 
 
 
 
 

 

 

Comments

  1. Love it

    • Love the creativity!

      For Tiffany’s written homework the spelling and punctuation was correct, but it was in all caps.

      • Mistress J says:

        What an interesting comment. So, do you feel points should have been deducted for all caps, or do you recommend punishment?

        • I feel points should be deducted. Perhaps Tiffany’s next writing assignment could also require more feminine handwriting.

          • Mistress J says:

            Excellent comment! You see,as a female with very messy handwriting, I appreciated her engineer-like precise and deliberate printing. There is no way my sentences would look like that!That is why she got an A with me. I love the comments folks, let’s keep this discussion going!

  2. Loved this session. If any reader has any ideas on homework or outfits I should try on please post or write in.

  3. I think some going out in public while wearing the butt plug could be fun for both of you. Maybe next time when you go shopping she has one in already and wears it to the shop. You can give her some “love taps” on her behind while in public to remind her of what a dirty whore she truly is.

  4. Thank you for sharing. As a only an average student and I must admit I didn’t always take homework seriously and more than once didn’t have anything to turn in, but never had a teacher like Mistress J and am sure the consequences would be as much as I could handle and I can’t imagine disappointing Mistress J.

    Tiffany let me say Bravo! I have know Mistress J for a few years now and if your performance and enthusiasm made her blush all I can say is Bravo! You must be a very special dirty little slut.

    Some ideas for more homework
    It sound like you have a fair amount of time between visit, and with time there should have elements of improvement and increase difficulty to complete.

    Ass – aspiration select a larger Mistress cock than you normally take. Shoot a series of videos of your anal training for your special anal final exam taking the full length and girth of that large Mistress cock.

    Completely agree with previous suggestion remote control toys in public are deliciously dirty and can build quite the need for release. I would add a bit of a twist. Vibrating Butt-plug and shock collar snug around your balls. Watching Mistress as you see her hand disappearing into her bag not knowing if it will be a pleasurable buzzing in the ass or a jolting shock to you fully loaded balls. Hope she doesn’t confuse the remotes.

    Texas Tim

    • Mistress J says:

      You are one pervy guy! I’m curious, did you get an erection writing this?

      • You know me so well of course I did. I have thought about a fun-filled outing with one or more toys to keep me focused on you.

    • Tim I love the thought of mixing a little pain and pleasure with remote play. It is exciting to think about all of the silent commands the pulses could stand for sent by my Mistress.

Speak Your Mind

*