My Sissy-in-Training Begins!

My new sissy-in-the-making, Marica, came over for a day-long talk and we laid out a plan for the following year. Things will shift and alter, as life does always, but here is the gist of what we decided would be accomplished.

Marica is Green Green Green

Marica has barely put on a pair of panties in her life, but has lived a life as a sissy online for a few years. She knows she is a sissy and wants to transform in real life as well. She and I have gotten along really well, but there can always be a few bumps in the road; that is normal and to be expected.

Marica cannot live full-time as a sissy, but neither can most sissies around the world. Therefore, I thought she would be a perfect fit, my having a separate life to work on as well. She will have assignments throughout the week and email with me about accomplishing them, then we will get together on Saturdays to talk about them and how she felt in the midst of the shift for the week.

Going Out en Femme

Near the end of the year, most likely Halloween, I will take Marica out for the first time in her full sissy ensemble. After that, at least 2 or 3 more times, I will take her out, first to a gay bar where sissies (and drag queens and transwomen) are known to congregate and then lastly, we will go on a sissy shopping trip so I can get her some lovely parting gifts to head off into her life as a sissy without my intense guidance. Of course, I am not just tossing her into the world! I will always be here for help, ideas and counseling, but she will, for the most part, be finished with her main sissification.

Topics We Will Cover

• Mindfulness
• Obedience and what being a submissive sissy means
• Shaving/Waxing/Lasering
• Feminine scents (and how to find them and why to use them)
• Make-up 101 to Marica putting on her own full face by the end of the year
• How to walk like a woman
• How to walk in heels
• How to find panties that feel good
• How to wear different pieces of lingerie
• How to wear stockings and pantyhose
• How to find and use breast forms
• How to find and wear hair
• How to discover what kind of sissy she is (sissy slut/little girl sissy/tailored sissy/sissy maid/etc.)
• How to choose clothes that fit online
• Beginning to Advanced Oral Dildo training
• Beginning to Advanced Pegging training
• Beginning to Advanced Oral Service to a Mistress training
• Playing with other sissies
• Chastity training
• Sexual acts for an audience
• Possible real live cock training (still negotiating this one)
• Finding a supportive sissy community in real life and online

Those are the main sissy topics over the year, most broken down into a 2-week or month-long lesson, but, of course, they build on each other and crisscross as time moves forward.

Marica’s Thoughts

I asked her today what her thoughts are as we embark on this journey together. She said she is very nervous, but excited. I asked if it made her clitty hard and she shyly said it did. That will be fun, embarrassing her that way! She is Latinx and not used to talking about sex out loud. She will get used to that! I asked what made her most nervous and, as I expected, sucking a cock. “I am not gay, Mistress!” I told her I was a lesbian and I loved sucking cock and I knew many straight girls and guys who sucked dick. Some serious desensitization is going to be called for when it comes to playing with dicks. I can do that!

Here we GO!

I am glad you are joining us for this adventure. Onward, ho!

The Sexy Sissy Saturday Radio Show Podcast that goes with this post can be heard HERE! Join us on Saturday Nights at 10pm ET HERE and also in the Chatroom HERE. I’d love to have you!