Author Archives: Mistress Ayn

What is the difference between a crossdresser and a sissy?

Gender play raises a lot of questions and people often get stuck on the labels.  In general, crossdressing is more of a positive transformation from male to female, experiencing all the wonderful female energy that goes with being pretty and pursued.  Sissy play is more about humiliation; stripping away the male ego and replacing it with a caricature of a woman or a girl.  This humiliation can be extreme and harsh or more benevolent and nurturing, like dealing with a child.

Both scenarios can be emotionally complex.  This underscores the importance in choosing the right Mistress or partner to help you with the exploration.

Does desiring to be feminized mean that I am gay or bi-sexual? 

Absolutely not!  Some men get fully dressed for the first time and declare themselves lesbians.  Others crave to suck cock, but I don’t think it’s done anything more than bring to the surface what has been swirling around underneath.

What happens in a feminization session?

There is no “typical” session when it comes to gender play.  Sessions that involve feminization are as wide and varied as you can possibly imagine.  They may involve forced feminization where the man is made to dress and behave like a slut and involve humiliation or it may be the opposite where a man wants to embrace his feminine side and feel the empowerment that comes from being a woman.  The spectrum between these extremes is where we normally play.

Here are some possible activities:

• Dressing – from sissy to slutty to elegant.
• Makeup – trans makeup to full drag queen and anything between.
• Manicure/Pedicure – out at a salon or in the privacy of the feminization area
• Esthetician services:  waxing, eyebrow threading, shaving, facial, etc.
• Full transformations that include makeup, wig, outfits, heels, etc.
• Sissy training – teaching you to act like a proper sissy, learning to curtsy, talk, walk, etc.
• Sissy maid training – learning to serve dominant females in various ways.
• Slut training – learning to suck a strap on, strap on training, etc.
• Medical scenes – enemas (getting your period), pussy/anal training, mock castrations/gender reassignment, etc.
• Public outings – this can include salon visits, dance clubs, dinner outings, shopping, etc.

As you can see, the options and combination of activities are almost endless and are defined by your imagination.

Here are links to reviews of sessions that involved gender play, crossdressing and sissy play.

Crossdressing help and feminization session

Pressing “Candy” into service at FemDom Mansion

Training sissy slut “Martina”

Transforming “Dianna”

Panty Slut Pamela’s overnight in the Dungeon

“Vanessa’s” gender reassignment

I also suggest read this interview at Simply Sxy about How to Explore and Enjoy Gender Play.

To set up your feminization session, visit MistressAyn.com, read through the and complete the experience/fetish form when you are ready to book. I also offer phone consultations and distance training for crossdresser and sissies.