Slut Tiffany Returns for More Torture.

Tiffany keeps coming back. This East Coast slut always visits me when she’s in town on business.

I met her at her hotel on Friday evening to dress her for our shopping trip. I had purchased little red pegging panties for her and I was very excited to see them on her. I had a remote controlled vibrating butt plug, a chastity cage, and a shopping list! 

Mistress J prepares Tiffany’s ass for shopping in San Jose!

After saying our hellos, I bent her over the bed and lubed her up, gave her a quick warm-up and slid in the butt plug. She said it was VERY full. I shoved her boy clit into the chastity cage, and we went back to the Hustler Store. For some reason, Tiffany was walking funny in the hallway. Was it because her junk was imprisoned and she had a large bulb in her butt? I don’t know. I do know, she opted to take the stairs rather than the elevator, so it must have felt good!

We shopped at Tiffany’s favorite store where she bought a few outfits and a hood to make videos. I intermittently turned the butt plug on and off, and she was enjoying our game.

I sent her home with some tasks to complete before our 10:30 am appointment Saturday morning.  The tasks were to record herself doing the following things:

1. Tiffany, you are instructed to give a lesson on anal training.

  • Make sure your red panties get some screen time.
  • Use white board to prepare an outline/and or diagrams or tips. Erase board when necessary.
  • Use rubbers on dildos
  • Grading will be on ability to convey an idea.

2. Demonstrate how you can ride a dildo  Play “Mustang Sally” as you gyrate on the dildo. Sing along during the chorus. Grading will be on vocal talent and riding ability.

3. At 11 pm, record yourself writing 50 times “I’m a big whore and like to choke on cocks.” Grading is on neatness, legibility, uniform writing and overall presentation. Provide a shot of the clock.

4. At midnight, record yourself inserting ice cubes in ass. Provide a shot of the clock. Extra points will be given if you can insert more than 10.

5. In the morning record yourself putting on your dainty things under your street clothes. Take a shower with provided feminine smelling soap. Use soap all weekend. Have breakfast downstairs or outside with lingerie on under clothes. 

6. Sleep in chastity. Arrive with butt plug in place.

7. Wear pegging panties under street clothes all weekend, and fly home in them.

Grading:

Anal stuff: Tiffany did a great job explaining the anal training and riding the dildo. I personally felt she didn’t sing loud enough during the chorus of Mustang Sally, so points were deducted. Also, she was a little off key…

Ice cubes: Major points were deducted because she was unable to insert ice cubes in her ass. She said the shape wasn’t conducive to sliding in, or some baloney like that. A backup activity of an oral sex demonstration on a dildo was provided, and I must say, she did a good job with that and provided interesting camera angles.

Mistress J makes sub give a BJ in San Jose, CA

Sloppy BJs are the best!

Sentences: Tiffany did a great job writing her 50 sentences. This time, a blank paper was provided so she did not have the benefit of the lines. I feel her penmanship is fantastic. I did not deduct for all capital letters, because her writing is so easy to read. I love how uniform each sentence is, and how they practically line up down the whole page. Points were deducted however. She complained a little by saying 50 sentences is a lot…  Wait until next time Tiff.

On Saturday, Tiffany arrived on time. We watched and critiqued her videos downstairs, then went up to the playroom for the fun.

Since she wrote about sucking cocks, I wanted to see her cock sucking/chocking skills in action. She complied readily. Her greedy mouth satisfied my two spring colored cocks and gave very sloppy and noisy blow jobs.

Mistress J humiliates male sub in San Jose, CA

Pretty in pink.

Spring is my favorite season and Easter had just passed. I used to love going to my neighborhood Easter Egg hunt as a kid. Tiffany made a cute bunny, don’t you think? She hopped around the playroom as I hummed the Bunny Hop Song. Her basket was filled with Tenga eggs and since she was a good girl, she got to take one home.

Tiffany is a bondage and anal slut. So, up went the legs! I have hooks all over my playroom, so her legs were pried open with a spreader bar and attached to the ceiling, while her arms were above her head. I teased her boy pussy and enjoyed using my ice roller on her delicate parts.  Cock slapping, vibrator torture, more cock sucking & toe sucking occurred. 

Chastity in San JoseFinally, the chastity device came off! Poor Tiffany’s boy clit was in shock after being caged up for a night and morning. Despite it’s shriveled appearance, I was able to edge her several times. 

Tiff had saved her cum for a week in anticipation of our meeting. Needless to say, she was VERY sensitive and called out “edge” very early during the game. I used both my hands and my feet to edge her.

Finally, Tiffany was allowed her release. But into a condom. And she had to suck her juice out. Poor girl. Such a humiliating morning. I felt sorry for her, for 10 seconds.

But Tiffany is a trooper. She went up to San Francisco that night for more play. What can I say, girls really do just want to have fun.

Humiliation and exposure are my specialties! Mistress J in San Jose, CA

Humiliation and exposure are my specialties!

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. What a humiliating and super hot time, really impressed with the creativity!
    The “I <3 Pegging" panties are perfect and love the bunny pic. Hopefully Tiffany will be able to practice with ice at home for next time.
    Thanks for sharing!

  2. What an adorable little slutty bunny! More fun that same evening???? Wow, she is a dirty little greedy whore.

  3. Tiffany says:

    What does the group think of the assignments given to me? Too hard or too soft? Always looking for improvements for next time

  4. Well done. I enjoy that she was required to stay up or wake up to record her homework. Next time it would be nice to have her get into different outfits and record a few sexy music videos.

    Another fun way to finish I use is to use the lube shooters to send their juices up into their bottom sometimes mixed with Vaseline lube to help fill them up.

    • Mistress J says:

      Tiffany had issues sucking her cum out of the condom. She said it wasn’t sliding up. I am considering the night before, having her release into a plastic bag and then having her freeze it in her refrigerator. She can enjoy her cumsicle the next day.

      • I like the pre release pop idea but from experience it is a great sight to watch a slut waddle home after filling up their bottom with a nice load of Vaseline – I hear as it sits inside it melts and gets nice and greasy almost to the point of leaking out… how embarrassing!

        I would also love to see a movie link her next time with slutty Tiff grinding on a dildo to some pop song with some glossy lips, eye shadow, fake tits and a sexy outfit.

    • I loved the time stamped chores from the last post. Maybe before she arrives have her insert one ice tube or banana half every 15 or 30 minutes… give her a target number to hit as a min and a goal for her max. This will both fill her up and keep her up late, depending on the number you set for her. Maybe in the down time you can have her read one of those how to books for your enjoyment later.

  5. Perfect.

    Next time if she is feeling adventurous challenge her with bananas and see how many she can push up inside her… if the Mistress is nice she will buy the green ones. Also ice balls could be a good solution for the anal challenge. Love the tests and yes absolutely get her to dress slutty with makeup and have her grind it for the camera!

    • Mistress J says:

      I am considering those ice cube molds for water bottles. They make ice tubes! 🙂

    • Tim great scene. It would be fun for a slut to try to push a soft banana up inside her bottom! That is a true showcase of how loose she is. Tiff can chase the fruit enema with some homemade ice cubes to help cool her down and work out the banana mash… I wonder if enema solution can freeze???

  6. Like the late night home work however as a guy I enjoy sluts that can handle some morning wood – give her a dildo that she can stick to the tube and work to some sexy pop song. I personally enjoy girls grinding to Britney or Christina. For face effect a mask with heavy lip gloss would be key while she squeezes into a latex corset and thigh high boots at 5:00am!!!

    Bonus points for some ass to mouth dildo action!

  7. Mistress J says:

    Thank you for all of the comments and ideas! Tiffany is getting horny again. She sent me a link to a nutrient syringe for the banana idea https://www.ebay.com/itm/100ML-Plastic-Large-Syringe-Measuring-Nutrient-Sterile-Reusable-Kitchen-Tool-BH/183687477716?epid=21016918653&hash=item2ac4a079d4:g:Ac8AAOSwKwBbFM6I. Nasty thing!

  8. Tiffany says:

    Does anyone have any recommendations for electronic shocking chastity cages?

  9. Mistress J says:

    Hello everyone,

    Tiffany returns on 5/24 for a daytime session. We will hit the mall, then return to the studio for filming and fun. As always, your suggestions are appreciated!

    • Sounds like Tiffany is willing to try anything her Mistress commands so I think you should have her right where you want her. Maybe have her take a few of the homemade ice tubes before she dances for the camera and I know some guys find it more humiliating and intense when they are forced to put on make up (eye shadow and lip gloss). I like the electric cage however a shocking plug could be just as fun

    • Anonymous says:

      Great rope scene uses an anal hook tied to a neck collar. I would also encourage to bind the arms and legs together. Have fun and put your feet in front of her for attention or sit on the floor in front of her head for some more personal attention… if you have time after the session a walk outside in a park or down the street with a little thong pantie set under pants is fun especially if you live up her ass with a big gob of Vaseline.

      • Mistress J says:

        Fun! Tiffany is always required to wear panties home.And, since she lives on the east coast, that means she flys home in them!!

  10. Mistress J says:

    Tiffany will be in San Jose Saturday 5/18 and again on 5/24.

    Let’s place our bets for the ice tube challenge. I predict she can take 3. What about you? Winner gets a prize.

    I’m not sure if the banana enema will take place Sat, but we will do if for sure on Thursday.

    • Curious says:

      My bet will be for Tiffany to take 4 ice tubes.

      This is fun, I’ve never been so excited to hear about another person’s session. Now I’m always wondering “what will Mistress J have slut Tiffany do next?”

    • Her is a link that I like for all of the various body positions a true bottom learns and loves. This could make for some productive late night reading.

      http://www.restrainedelegance.com/preview/lexicon1/icons/index.php

      Enjoy!

    • Follower says:

      Is the challenge for the whole night or just an hour? You should make her take 3 tubes at different hours of the night, 3 at 12, 3, 6. I am interested to know what number would cause her to have to expel during the night…

      You should also give her a different girly scented soap to bath in or lotion, something to have her smelling like a stripper!

      • Mistress J says:

        I have a small bottle of perfume I don’t like. I think it will smell fabulous on Tiffany!!!!

        Thanks for the tip.

    • Mistress Freya says:

      But sessions for me involve my bottom jerk off while I peg him and I set a time limit for him to cum. If he cums he likes up his mess and if he can’t then he goes home frustrated. No matter what I have him end the session with some body worship; mistress loves some rimming and oral sex!!!

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