Crossdresser stepping out for the first time

Dear Readers,

It has been a few weeks since I shared a crossdressing success story. With the festive season and rush of the “first week back at work” behind me, I’m back into the swing of things. This week’s story is from an avid reader of Crossdresser Heaven who contributes so much back to the community through her thoughtful and loving comments.

If you’ve got a story of crossdressing success, however small, take a moment to share your crossdressing story. Or once you’ve met Ragina, continue reading about Randi’s crossdressing adventure.

Meet Ragina

My femme name is Ragina, and I live in Georgia with my wife of 20 years. I have been crossdressing off and on since early childhood, but have been regularly dressing for about thirty years or so.

Crossdressing Success Story

My first recolection of crossdressing was many years ago when as a youngster I would have to accompany my mother to choir practice at church because my dad traveled a lot for his job at the time. During those years, women still wore gloves to church, and of course , someone would accidently leave a pair . They found thier way to the lost and found box, where they would sooner or later be claimed. I don’t know what attracted me to those pretty white gloves, but they called to me.

Nervously, I grabbed several pairs and hiding myself in a closet (ha,ha,), I tried them on. The feeling was like no other feeling I had ever had, and I pocketed a couple pairs to take home. This continued for a couple of years. Then I happened to find a pair of Mom’s stockings balled up in the trash and rescued them out of curiousity. I knew enough that they went on the legs, so , locking myself in my room, I tried them on and wow, what a feeling! So soft and smooth on my legs.

So that set in motion my pattern of crossdressing for a time. Of course I became more and more curious of the other things that women wore, bras,panties slips,and so on,and vowed somehow to get these garments for myself. By this time, I was in junior high school and all the girls were well developed. I was taking music lessons at the time and had to wait after school for my lesson. Somehow, I accidently wound up finding a girls clothes, and lo and behold were all the things that I’d desired.

I stuffed them all into my bookbag and took them home. This one act, along with trying those clothes on galvanized my love of all things feminine. I continued to crossdress in bits and pieces from then on, eventually being able to purchace clothes on my own. Of course, all this was done in secret, as Mom wouldn’ understand at all. Little did I know that she already knew.

Eventually I married and started a family, still dressing in secret. This first marriage didn’t last, not because of my crossdressing. I relocated here courtesy of the military, met and married my current wife, being careful to let her in on my secret hobby. At first, she had a very hard time understanding and accepting my feminine side, but as time went on,with tenderness and patience on my part, she grew to accept me as I am.

I now have the best of both worlds, a wife who loves the man that I am and a wonderful girlfriend to hang out with. Life doesn’t get much better than this. To all my sisters out there, be patient and loving, the person you are is wonderful and worth loving.


Ragina, thank you for your beautiful story – truly a crossdressing success! If any readers are struggling to find their own crossdressing success I highly recommend Peggy Rudd’s book, My Husband Wears My Clothes.

More Articles by The Author

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I’m passionate about creating a safe space for everyone in the transgender community to find laughter and friendship on their journey. I completed my physical transition in 2011 and through it I lost everything, and gained everything. I am blessed that I was forced to gaze inward and embark on the journey to discover and live my authentic self. My deepest wish is that all who wander here may find peace, happiness and freedom.
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