Going Out Crossdressed

When I was about 7 I would dress in my mom's clothes and have a super time. If I felt that I had the time, I would put make-up on but of course my mom's clothes were just a tad to large, so there was no going out. LOL
As I grew up and got married, I thought that all of that was over, boy was I wrong. When I had some free time from my wife, I dressed and drove out around the neighborhood and town and even went onto the freeway and went to the rest area restrooms. I, of course being dressed as a girl  would go into the ladies room. One day while out feeling pretty confident, I went into a Penney's store and walked around looking at dresses. I LOVE it until a small girl came up and thinking I was "not right" started laughing at me. (Little girls always seem to see thru a CD'er.) This went on for quite a few years until my wife caught me coming home dressed....no way out of it. By the way, she thought that I had been going into her clothes for quite some time.
She wanted me to go see a therapist which I did WHICH MADE NO DIFFERENCE.
Now its a few years later and my first wife died from cancer and for some unknown reason, I got married again without telling my 2nd wife. Of all the stupid things, I should have told her but I didn't have the guts.  TELL YOUR WIFE, IF POSSIBL, BEFORE YOU ARE MARRIED.
Enough for now.
karen42 karen42
66-70, M
4 Responses Aug 1, 2011

My wife prefers me to be a sissy and her *****. It helps that she is my mistress and has made me a cuckold

Yes in perfect 20-20 hindsight telling our potential love interests about our dressing is proper but soo very very scary. I too hoped that marriage would "Cure" me...but we all know that doesn't happen.<br />
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I'm facing a crisis at this point where she hates that I dress and won't consider approving of me going out in public. Because it was so hidden back then, we mature gurls are suffering in ways that I hope the younger generations can avoid.

Lori, yes we did "marriage counseling" a few years back when she caught me ************ in the bathroom wearing her bra. I had to tell her about my dressing and she put her foot down about not using her clothes. She is very narrow minded about certain things and did not want to be educated about the TG condition at all. I began accumulating my own wardrobe and now have a huge stash of clothes, shoes, and lingerie. I also began feeling confident enough to go out. So, it remains a point of tension between us. Also, she entered menopause about the same time and we have not had sexual relations in over a decade, which used to be a big part of our affection for each other. THus we are at a little stalemate where she feels she has to stay due to financial reasons and I don't want to lose her since she is my best friend, yet i need time as Joellie.

One bright spot is that she is beginning to get a number of gay and lesbian acquaintances and is becoming a little less concerned about what other people think, so her tolerance for my kinky needs is growing, but just a little.

Cindy and Ohio Sissy .... you both are so right, a crossdresser should totally tell any woman BEFORE marriage that he is a C.D. This I believe totally NOW. <br />
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At the time I was scared that I would loose her because she is an old fashioned thinking woman.<br />
i still should have told her.

My wife knew from day one that I wear female attire!