Tiffany Goes Back to School. Part 2

Tiffany’s tales of debauchery continue to delight readers around the globe! At long last, here is the final installment of Tiffany’s Back to School Special. She is very close to graduating.

Tiffany first enrolled in Mistress J’s School of Sissy Deportment at the end of 2017. Learning to suck cock, ass play, dressing nice and completing homework assignments are all steps to her submissive sissy graduation.

Her final exam is to have a date with a human man, and have him take her boy pussy virginity. This blog post describes her next to last step in her transformation and some juicy details. 

Dumping her load Friday night.

Friday night, after her homework assignments were completed, Tiffany was instructed to film herself dumping her load, saving it, and locking herself into chastity.

Tiffany likes to masturbate. She also enjoys filming herself, so this was a win-win situation. Tiffany was instructed to add the cum to her hot oatmeal the next day for flavor. YUM!

Tiffany was a little unsettled by our adventure outdoors, so I made sure she enjoyed a little more of that. She had to go downstairs to breakfast wearing her kitty t-shirt and perfume. Then, during the PE portion of her school day, she had to run a few laps in the hallway in her tight gym clothes. For hydration purposes, she enjoyed a cup filled with her own piss to sip on throughout the day.

Tiffany’s pussy

When I came Saturday night by to do her makeup, Tiffany was still in her schoolgirl outfit. She proudly showed me her homework and I asked her to show me her pussy before our friend came over. She enthusiastically did as she was told.

We all know Tiffany enjoys dancing and shaking her ass. She was excited to change into a slutty club outfit and dance with her new friend Raj.

Raj was very punctual, he was excited to meet Tiffany, who he had read so much about. We played a a came of high card wins (loser got a spanking by me) and enjoyed a glass of wine. 

Tiffany had created a playlist from songs Raj emailed earlier, let me tell you, this girl had fire in her drawers! She started dancing and before you knew it, the three of us were dancing in the room! 

There was some serious heat between those two. Raj was all over Tiffany, exploring her body and nibbling her neck. I suggested she give him a lap dance and she was happy to oblige!

Tiffany got Raj nice and horny by shaking her tush in his face. I insisted that Raj strip, and he was rock hard and dripping.

I ordered Tiffany down on her knees and she began pleasuring Raj. I have to say, I was quite impressed by her blowjob technique. (I even might have learned a few things.) Raj loved her technique as well and exploded like you wouldn’t believe.

Tiffany is so close to graduating. Her final assignment takes place next month, and will be a remote test with Raj giving the exam up her butt. I hope he gives her a passing grade… 

The complete set of the Tiffany Tales are here:

I can help you reach your sissy goals, or have you explore your non-sissy desires. 

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  I am in San Jose, California.  I look forward to hearing from you.





























Tiffany Goes Back to School. Part 1

New backpack.


The beautiful Tiffany was coming to town for one last trip before the year ended and she wanted to go all out!

Tiffany wanted to have a milestone in her education, as she feels she is getting ready to graduate into a real and true sissy slut. 

She wants to LEARN as much as possible, and who better to teach her than Mistress J?

The slut was very horny and wanted to taste real cock. I had the perfect friend in mind when she made this request, but more on that in Part 2.

Tiff was going to get a pussy wax at a local place and check into her regular hotel. She was going to have Friday late afternoon and evening and much of Saturday for homework assignments. I told her I’d come over to her hotel Saturday evening for grading and play.

I had a special gift for her, a personalized backpack, hot pink of course, and left it at the desk earlier that day. I wanted her to have it waiting for her upon her arrival. It was full of clothes and gadgets, as well as instructions for the weekend.

Tiffany had two pages of homework assignments. I won’t bore you by listing all of them, so only the highlights will be discussed. 

One of my favorite tasks, was Tiffany was allowed to only eat “kid food” that weekend. Juice boxes, mac and cheese, PB&J, oatmeal, and soups were her menu. Which she had to purchase herself.

The school subjects were:

Physical Education, Ceramics, Math, Photography, Film Making and Creative Writing.

Ceramics was one of my favorite subjects. I had high hopes for this one. I supplied her with a Play Dough kit with an assortment of colors and letter stamps. She was instructed to make pornographic images and naughty words. Grading would be on technique as well as creativity. This is what she came up with. Grade: C. Why a C? I was hoping for interesting color combinations and naughtier people.

Tiffany fared much better in the other subjects, which also translated to a fabulous grade in Film Making.

Math required Tiffany to do multiplication and addition exercises by grabbing a squishy pecker with her butt cheek, walk across the room and drop it on the chair. She really knows her numbers and has tight little cheeks.  She could cross the room without dropping a pecker! Grade: A.

Tiffany really shined in PE. She took this subject seriously. She was instructed to do arm curls with the heavy metal dildo with a butt plug in her butt. Look at this photo. What perfect form! The plug stayed in the whole time. Grade: A+.

She may have scored an A+ in Film Making, but this girl did NOT take a single still photo. I had to make still photos from the videos. Such a Bad Girl. Photography Grade: F.

Creative Writing was another area of expertise. She was instructed to write love letters to Mr D, Amber and Mike Tyson (Tiffany is a huge fan).

Below is the letter to Mike Tyson. I want to send Mr D and Amber their letters privately, then they can give a grade themselves. Please email me at mistressjstudios@gmail with your email and I’ll forward her letter.

A peek up the school girl’s skirt!

Mike’s letter:


Love your power and body and I can’t wait until I am woman enough to take your BBC.  I am working with my Mistress to become more mature and I can’t wait until a BBC is allowed to be put in front on my body…  My mouth and bottom would by a lovely welcoming home for you as I would take my time fully exploring your needs.
Please think of me and let me know what I can do to prove myself to you.”
What do you all think of this letter? Aside from the rather casual salutation, do you think it is worthy of a B+? 
I leave this post with a photo of Tiffany studying her Bible. Stay tuned for my next episode of Tiffany Goes Back to School. The school girl cuts loose and becomes a real slut. You don’t want to miss it.