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.






























  1. I can honestly say that I am amazed with how much “progress” I have made sense my first visit. It is impressive how well Mistress J has nudged me closer and closer toward a fully feminine submissive status and mindset… I never thought at the end of my first session I would be in full makeup, club style lingerie and on my knees sucking off a real cock.

    For anyone looking or interested in a transformation for you or a friend I absolutely recommend Mistress J as a teacher. She has fully transformed me into a true submissive slut – true to her master design and planning…. how cunning and smart she is to remold a male personality into a blossoming Sub Slut BDSM Slave (I am a finished sex slave ready to satisfy my master).

  2. Well this is impressive. For you to take a boy and slowly guide him / her into a slutty sex slave is amazing. This blog and effort deserves a round of applause!

    If I find a worthless man who is unable to satisfy my needs I will remember this story and think about a transformation for him.

    Great job – Girl Power is real 🙂

  3. This has been a very fascinating journey to follow. Mistress I have to say I am very impressed that you were able to guide your girl to become a true cock sucker.

    Can’t wait to here how her first night grade is.

  4. Kinky Kevin says:

    Great job mistress J. Tiffany’s journey has been a great read and reminds me slightly of how I got started. I hope you can keep developing her and I would encourage you both to explore more with house assignments and group play… chasity is a great way to help encourage the positive assignments. Also the HolyTrainer is the best low profile cage to pair with lingerie or dresses.

  5. This has been such an exciting journey to follow. I’ve been impressed with Mistress J’s creativity and Tiffany’s sissy growth.

    I really look forward to hearing about Tiffany’s next escapades.

    • Tiffany says:


      I would love to hear your wildest suggestions for the next round of homework for Mistress to assign me.


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