Crossdressing Phonesex Essays By Mistress Violet

Essay # 3

Why do men cross-dress?  Like many other topics in life, there is no simple, clear cut answer to that question.  If there were, you probably wouldn’t be reading this essay and the debates on this topic would be over.  In the case of most cross-dressers, the fascination with women’s clothing started when they were very young.  Most of them remember dressing up in mommy’s clothing, or being dressed up by their sisters.  Men have told me that when they were too old to play dress-up with their sisters, they felt lost.  And then, in their teens many found themselves nervously buying a pair of pantyhose from the grocery store and wearing them in secret in their bedroom.  It turned them on and they felt compelled to hide their activities.   

Eventually they grow up and still feel that need to wear women’s clothes.  It seems no one can quite explain precisely where that comes from.  The media often portrays cross-dressing as a sexual perversion.  They seem to see a person’s desire to cross-dress as purely sexual gratification.  There is one glaring problem with this theory though.  When most cross-dressers first felt the desire to cross-dress, they didn’t even know what sex was.  So we must look at other explanations.

I have asked many cross-dressers why they love it so much, and they inevitably describe the need as “feeling more comfortable wearing women’s clothing”.  This is sometimes coupled with their desire to be seen as a woman.  So they desire to not just dress like a woman, but behave like one as well.  A strong desire to wear make-up and otherwise pass as a woman. 

There are others who cross-dress for sexual excitement.  These men tend to focus solely on looks, not feeling that drive to become a woman.  It is something they only do during sex and once the passion is over, the desire to wear anything feminine is gone as well.  It is clear that the need to cross-dress is a spectrum. 

One theory is that cross-dressing is a way of challenging society’s preconceptions about gender.  It is true that some men cross-dress because they are unhappy at being men.  They feel they were literally “born in the wrong body”.  Others don’t mind being male, but do like to put on women’s clothing occasionally.  For some men cross-dressing is a fashion statement.  And then there are some who have deep emotional needs that can only be met by the comfort of wearing women’s clothing.  I enjoy assisting all types of cross-dressers.  Whether they are new, old hands, haven’t done it for 20 years or ready to go full-feminization.

Clearly, it is an intensely personal decision to become a cross-dresser.  Often the man becomes confused and guilt ridden.  He may be married or dating a woman and fear her response to his needs.  He needs someone to talk to…someone who will listen and not judge…someone who accepts him as he is.  That someone…is me.