Essay: More Fun for More Crossdressers

I’d like to offer my opinions that might help my CD buddies to find what they are looking for whether it is a mistress or their next play friend.  My remarks are with male cross dressers, not female, in mind.

Anecdotally, we understand that the majority of dommes are not interested in gender bending in their s-type person or in diluting their male’s masculine presentation.  I make that statement from my own experiences with both dommes and with CDs.  More than a few CDs have shared their experiences with me.  But that being said, the pond is still broad for the guy in size thirteen stilettos because

  1. there is still a significant number of dommes who dearly love CDs and
  2. there are plenty more dominant females—not dommes—who love CDs and
  3. some CDs might choose to sometimes lead with a different kink and make cross dressing secondary, thus, broadening who is available to them.

What do cross dressing males want more than new shoes, a perfect form fitting retro-style dress, and little white gloves?  Acceptance.  Not so different than what the rest of us want, right?  He wants a female who is tickled to see him in his new pumps.  The female in his fantasies loves to go there with him as she zips up the dress that’s just the right color for his complexion.  They both move emotionally and psychologically into the feminine as only they together can formulate that concept.  He’s attempting to use himself as an altar to the feminine/Feminine.  She accepts and encourages his gift.  How crazy intimate is that?  What’s perfect is finding all those females who are in on worshiping the feminine/Feminine by partnering in a cross dressing sort of way.

It’s important to know what dominant females need relative to masculine and feminine energy:

  1. Some need to draw the masculine toward them, not the feminine.  They need masculine energy to balance their own representation of the feminine.  They have no use for the energy of cross dressing—a male in drag?  It makes no sense to them.  A handful of these dommes are unfriendly even hostile toward CDs who dare to approach them.  Other dommes express disinterest.  The fem end of the masculine range is unattractive to this group.  What’s at issue, more importantly, for this group is power and control.  By approaching this group as a male in female clothing then the domme is already offended because dressing himself is an act out of her control.  She did not tell you to dress or dress in this fem way or dress in a manner that is not going to be to her liking.  A secondary offense might be his apparent assumption that she was going to be pleased with a male in female clothing.
  2. The second group is very different. They are motivated to join the CD in his pursuit of the feminine represented as the top of the heap (female superiority, goddess worship, and other similar formulations).  Some dominants humiliate the CD or make fun of him in a playful way.  Some CDs love this kind of deliberate consensual tension in the relationship.  It’s fun for both.  These dommes vary in their direct involvement with his make up and dress.  They might shop together.  She might choose his clothing to wear for a scene or for daily wear (like the maid’s costume).

2b. Other pairs take a softer approach that has nothing to do with humiliation games.  The dominant encourages the CD’s fem dress and strikes an attitude that is similar to that of a pet owner.  She feels protective of him.  These dommes may be very hands on and help their CD male to dress. They may go shopping together. Both domme and sub CD benefit from together holding a delicious intimate secret of feminization.

  1. There is a third group that makes cross dressing a secondary item in the relationship, that is, it isnota contributing factor in the power dynamic.  The domme has accepted her sub or slave partner for other reasons such as they both love spanking or bondage or both as their main kink.  But he feels most like himself when he is in fem dress.  She is fine with him dressing up but it doesn’t do anything for her specifically.  It may be true that cross dressing enhances sub mind for him but the domme just isn’t interested in playing to that fact as part of their dynamic.  Cross dressing does nothing for her sense of dominance.

Understand that cross dressing is a phenomenon driven by the gender bending person as opposed to what we call “the feminization of males.”  That latter phrase refers to the female driving the action.  She is entertained by feminizing her male.  She puts him in female underwear and high heels by her own hand or simply orders him to dress for her.  Feminization does, indeed, play into her dominance while cross dressing may or may not.

It’s a good idea to re-examine how to approach a dominant female.  We, all, struggle at analyzing an online profile.  Should we or shouldn’t we send this person a message?  Based on the what she wrote do I stand a reasonable chance at receiving a positive response or any response at all?  If there is no indication in her profile that she is interested in cross dressing or feminization of the male then usually the best thing to do is to steer clear.  Why go to the door of someone who is not in the same hemisphere you are in?  However, the CD male can take a chance on anyone by politely asking if Mistress/Madam/Lady takes an interest in cross dressing or in feminizing the male or includes such in her play.  Hopefully, the CD applicant will receive a polite response back.  If the answer is no then move on without an ill thought.

The CD male can also keep in mind yet another option.  He can sometimes not lead with fem for the purpose of gaining more play partners, dommes and not-dommes.  Examine someone’s profile for the interests expressed there that he shares.  She loves electrostimulation.  He likes it, too.  The more shared interests the better.  The CD male could then approach the Lady as a prospective electro play partner or whatever the interest is.  “Oh, and, in addition to our many shared interests you might be interested to know that I am a cross dresser.”  If you share this information only in your profile plus during the interview that’s fair, too.  If she isn’t into cross dressing you were already prepared to play in the other ways that please her.  The prospective dominant might go for it.  Dropping or downplaying the fem-self on a part time basis will only be comfortable for some CDs and definitely not for others.

My friends, broaden the field in which you operate.  Don’t play a zero sum game based on the false notion that every domme or every female is going to be delighted by and desirous of your dress and heels and makeup.  By being flexible about giving the prospective dominant what she wants you are likely to have a fun series of play sessions ahead of you and more likely to discover your one true domme or true romance along the way.  I hope that you will make a more targeted reaching out to the lady who already loves you.  She’s out there.   ******

©  2015 Selenite Press.  You may quote from my essays and you may use the entire essay elsewhere but only with full credit to the author, Sky Gates.  Thank you.

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