A Tale of Two Sissies

Actually, it was one sissy, but she saw me twice.

Someone is happy to see me.

Tiffany was trapped inside of a young, Asian male’s body. She longed for freedom, but lacked a safe place for expression. Tiffany had never sucked cock, but wanted to. She had never been pounded up the ass, but desired it. Tiffany had never worn stockings, heels or lingerie and cried herself to sleep for longing

Then one day, while visiting San Jose, she called Mistress J Studios. Mistress J invited her over they had fun together. Tiffany tried on some lacy undies and a bra. She walked in heels for the first time, stumbling only once.

Tiffany went through a strict training regimen. First, she had to warm up her throat on a series of rubber dongs. I stick them on a mirror and it become my glory hole. The slut kneeled down and worked the cocks well. Each time she went a little deeper and after mastering one cock, she moved on to a bigger one.

After the cock sucking, it was time to work on the clit and pussy.I like to have my sluts wear open crotch panties. That way I have access to the goods and the lingerie can stay on. The sissy’s boy clit (cock) and boy pussy (ass) gets a good workout, and she remains feminine.

She leaned against the cross facing me first. I slapped her clitty and pinched her nipples. Other types of play occurred, and after a while, she was instructed to turn around and present her pussy to me. She complied, and enjoyed a series of swats, pinches and floggings on her butt and back.

Finally, it was time for anal/pussy training. Spread out and chained pussy up on the floor she eagerly awaited my gloved fingers. After getting her tight hole a little looser, she was begging for more.

I won’t go into any more sordid details, but Tiffany got the training she needed. She was filled to the brim and went home a satisfied lady.

But wait, there’s more!  

Business brought the slut back to the bay Area and she continued with her training. A full makeover took place and I decided

Three cheers for the red, white and blue!

to dress her up like a trashy girl. She was also treated like one.  It sure is fun watching these girls blossom and spread their, um, wings.

Tiffany showed her true colors, taking it like a champ. She is a patriotic princess and believes in the freedom to be a slut!

If you have a hidden sissy and are curious about my style of Feminine Domination, I invite you to contact me for a session in my San Jose studio.

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 bending are welcomed and encouraged here.

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

16 thoughts on “A Tale of Two Sissies

  1. Mistress J as this is where your first created Tiffany I wanted to say congratulations. Second I wanted to share a few fun anal training observations I have amassed over the last few years, nothing you have done has been out of place first of all.

    If she likes to take your love doggie style I would encourage you to workout the wand attachment with a short and wide dildo. The vibration sensation tends to be felt at the base of the rectum cavity so a shorter dildo typically works best to help one open her up and two drive her wild. Second I would like to hear your thoughts on ginger root pegging. While I have only done this game once the sub shock wildly when we would insert the fresh pealed root.

    The other add on I will leave with is to coat her ass cheeks with icy hot or hip-freeze. Try to avoid her crack and hole however warming up her bottom with this gel is a great way to have her feel your presence while you are focusing on other maters in the dungeon.

    Great series and I love to see her growth under your training.

  2. Can’t wait to hear about Tiffany’s performance in August. I trust Mistress will be able to coach her to show off her true slutty nature…

    For temp tattoo locations a tramp stamp is classic however ink on the hip or ribs also shows very well.

    Also if the space allows this it would be great to see some pictures with Tiffany on a leash tied off to a tree or guided by your hand.

  3. Miss J if you love those then I have to share this. The song is horrible, unfortunately, however the dance move the girls are doing is simply amazingly humiliating. Walking on all fours with a leg kick…
    If the park is quiet this is sure to please the crowd… especially if a camera or phone is rolling!

  4. Mistress It would be great to have Tiffany pay respect to this first post and visit when she comes back for her next visit.

    Dress her up in a similar set of lingerie and have her take a full face of makeup… a strip tease or GoGo dance on film would be a nice touch. I love the 80s workout but this would be a fun way theme to try to work in.

  5. What a journey for your girl Mistress. All I want to say of great job bringing her out of her shell and into a full woman that was strutting around the park, she is almost in full bloom.

    When my boys were in bloom I would love to also take them out and help introduce them to their new body: their first outfit typically was a nice skin tight pair of jeans with a pink set of panties underneath. I liked to have them wear a male polo shirt with a bralet and would have them wearing light lip gloss and perfume.

    You should also have her take a milk enema in her room to help prep her bottom for your dildos. If not milk I would give her a set amount of volume she is to hold for a few minutes.

  6. They are expensive however if you have a fucking machine strap her down and have her take 15 minutes of various speeds.

    Nothing better than to flick the switch and sit back and enjoy the show… if she behaves you can give her extra lube to help her out. When it is close to the end give her simple math problems to solve; you will be dying laughing at some of the answers after 15 minutes of impact 🙂

    Bonus Pt for her going A2M (ass to mouth) with the dildo 😉

    • When use a machine I love having the bottom count (up or down) to a number I pick. The best parts are when their voice gets too weak to hear or they say a number twice and have to start over again.

      Each session is part of a journey and you should get her to try new things each time.

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