My Journey As a Cross-dresser: Masturbating In Sexy Women Boots

Fetishes are not quite as unique as fingerprints, in that everyone has a specific type; but they are very widely represented.  Some guys are attracted to panties, nylon stockings, bras, leather, latex, purses, lipstick, perhaps even urine, feces, saliva etc. etc. etc…..anything associated with the carnal desire to elevate themselves to “sexual nirvana”.  Little did I know about these things at 11 years old.  The only thing that I was certain of was that I was drawn like a moth to a flame to high heeled stiletto Boots.  And when I laid my head down at night the object of my desires was in the next bedroom closet where my sister kept her Boots.  The close proximity and the reality of my obsession made for some very anxious and cum filled underwear nights. 
In 1979, there was no internet; the encyclopedia Britannica did not cover such taboo topics and the mainstream talk shows and sitcoms only skirted the boundaries of paraphilia.  (In retrospect, I do believed that many producers knew that subtle interjections of fetish clothing and topics into an otherwise prime-time TV program had profound effects on ratings.  And MTV was founded on such carnal desires.  But that is another topic for another time.)  All I knew in 1979 was that I had a compelling desire to wear the shiny black stiletto Boots that were in a silver box in the bottom of my sister’s closet.  And I longed for the opportunity to have a minute alone with the object of my dreams – Boots!
Initially I did not question a thing.  I just knew that I liked my sister’s Boots and I looked forward to dressing in them and masturbating every chance I could get.  But as I began to apply some reason to the experience, questions that I had no resources to answer began to arise.  I could not ask my parents who were ultra-conservative and very religious; they believed that anything provocative or sexually explicit was decadent and sinful.  I was full of questions, but still committed entirely to the object of my desire – a pair of high heeled Boots. So, I did little thinking of the difficult questions, and simply followed my primal desires of Masturbating in those sexy women’s Boots. 
Can you relate to this?                                 

Mistress “CD” Jessica

Not the best quality, but I looove this pic! A good angle of my legs!

3 thoughts on “My Journey As a Cross-dresser: Masturbating In Sexy Women Boots

  1. Sort of the same story. Before the age of maaturbation exploration, I tried on a pair of boots. Became hard as I put them on, and climaxed as soon as I zipped them up.

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.