Crossdressing Success Stories are real stories from crossdressers who have overcome fear and self-doubt to let their feminine beauty emerge. Their story of success may be one of triumph over adversity, or the blossoming of a special relationship of openness with those they love. Perhaps the crossdresser’s wife played an even more integral part of their success story.

Share Your Crossdressing Success Story

Please share your crossdressing success story, it only takes a moment and your crossdressing victory will encourage a sister who is just exploring her transgendered nature. I’ll post your story on Crossdresser Heaven within a few weeks.

Meet Mandy

I’m a 31 year old white male, heterosexual, and live in the Seattle area.  I’ve had the desire to crossdress for about as long as I can remember.

Mandy’s Crossdressing Success Story

I think it started when I was maybe 5 or 6?  My best friend, a girl, lived across the street from me.  She was really big into dance, and as such, had lots of different costumes.  I remember she had me try on one of her pink tutu’s one day (don’t know why…. she probably thought it’d be funny.)  I remember once I put it on, the embarassment went away and I felt oddly comfortable, and even satisfied.  For awhile, every time I went over to her house, I wanted to try on the tutu.  The humor in it wore off eventually, and I started to experiment on my own.  I remember taking naps in the afternoon when home, and while mom was at the other end of the house watching her soaps, I’d sneak into her room and steal a few things from her drawers.

Taking mom’s stuff, or stuff from female friends and cousins, was all I did up until I moved out and lived on my own.  Thank God for the JCPenney catalog, and the internet.  I ordered myself a decent amount of underwear (that actually FIT!), then sort of lost interest in it all for awhile.  Don’t know why.  A good few years went by where I still had the free time to do it, just never really did.  When the opportunity came to move across the country for a job, I took that as the chance to pitch everything (purge…  I know, “don’t do it!!!”)  as I thought I was done with all of it.  It wasn’t until I told my wife about it a few years later that I got back into it, through her encouragement.

I’m now married, have an amazing wife who loves and accepts everything about me, and is willing (sometimes pushing) me to explore the depths of my interest in it all.  I’ve learned a lot this last year, and am loving it more than ever!  Hopefully, with the wife’s help, I’ll work up to a night out or something fully dressed  🙂

Visit Transgender Heaven

It warms my heart to hear stories where the crossdressers wife plays such a positive and affirming role. I know that many crossdressers agonize over their wife’s acceptance, often keeping their secret for many years beyond what they should bear. If you are struggling to tell your wife, please read how to tell your wife you crossdress. If you’ve told your wife with great success, please comment and share your advice with others.

Hugs and blessings,

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10 years ago

wow what a lovely store, so please your wife is with you on your girly road
sadly mine not, go girl

love & hugs Tammy

Johnny G
9 years ago

I am a “former” Cross-dresser.  By that, I am stating for the record that I do not/can not dress anymore.  Let me explain…For most of my life I have been interested in “dressing-up”.  My mother  and my sister (older by two yrs.) knew of my interests, and on Halloween went so far as to dress me in female clothes.  One year when I was in 6th. grade, I was dressed by my mother as a lady of the times. (about early 60’s.)  She sent me to a costume party like that.   By practical use of cosmetics ( I LOVED the deep… Read more »

Trinity Castro
9 years ago

I’ve been a crossdresser for years. I’ve had to hide the fact from family & friends, but within the last couple of years I’ve “come out” and told a few select people that I know I can trust. My fiance is a very supportive woman who not only accepts the fact that I’m a CD, but she helps me with the outfits that I select when I do go out en femme. There has even been a night when she went out with me to a club and we had a wonderful time. I’m more comfortable now than I ever… Read more »

7 years ago

I am also acrossdresser I started from very my childhood ihad not left any of my friend sister whose bra I had not tasted ihave not left my sister in laws dresses I use to dressup when ever I get chan ce I use to show my grand mother she use to say I look realy like girl l like to thank one of my friend sister who has allowd me to use her dresses and her family encurgedme of cource my famil y and my kids knew aboutmy crossdressing but I do not dare to go in front of… Read more »

kendra wilson
5 years ago

hello I to was in viet nam 1968-69 usmc I to started dressing when I was 4 or 5 just panties and loved it got to wear a dress when I was about 10. I got married when I got back from nam thinking I would stop dressing but i did not I let my wife know about my dressing and did not go to good but we worked on it and she is still with me I wear panties and a bra all the time and get to fully dress 1 or 2 times a week. she is still… Read more »

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