Exploring crossdressing in drab

Crossdressing success stories are a look into the tribulations and elations shared by crossdressers who struggle with their dual identity. If you would like to share a story of a small joy you experienced while crossdressing, I encourage you to submit your own crossdressing success story.

If you are the wife or girlfriend of a crossdresser, your story of acceptance will be a comfort to many. Please share, you can do so anonymously if you’d like.

Our next lady has a story that shares a winding road through to self acceptance, and will be a comfort if you feel that you’re lost on your journey that has no destination.

Meet Serena

My name is Serena, and I’m a 37 year old, tall (6’4) crossdresser from Tucson. Like many of you, I began dressing when I was about 11 or 12, wearing my mom’s pantyhose.

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Serena’s Crossdressing Success Story

Since then, I took every opportunity to wear lingerie and hosiery, often sneaking into the drawers of various friends, family and girlfriends, and eventually buying them myself. It has always been very private. Several years ago, I decided to dress much more seriously. For the first time, I shaved my whole body, bought a wig, make-up, breast forms, etc. I shopped for clothing at crossdresser friendly thrift stores, and bought lingerie, hosiery, and shoes until my tranny heart was content. After about eight months, I stopped dressing out of concern that all of this was somehow impeding my ability to find a mate, get married, have a family, etc. Talk about a dilemma.

As invigorating as my exploration of Serena was, I have not attempted anything like it since (of course, I do still love to paint my toe nails and wear stockings – who doesn’t?). Not being blessed with the most feminine physical features (except for my nice long legs and butt – yes, I am vain), I decided that I would leave dressing to the girls who did it best. Instead, I chose to explore my attraction to transgendered women. At the time, this seemed like the perfect way to balance exploration of my gender identity/sexuality with my long term goal of settling down with a genetic woman. No longer would I have to worry about meeting the girl of my dreams and missing a golden opportunity because she might soon discover that I was smooth all over and my love patch was shaped like a heart! Talk about difficult to explain.

Unfortunately, this decision also entailed me purging all the wonderful clothes, shoes, lingerie, make-up, wigs, hosiery, etc. that I had accumulated up to that point. On the bright side, my time as Serena forced me to finally acknowledge and accept that I am a crossdresser, and not feel one ounce of shame for it.

After the purge, I had a couple of short relationships with girls that I met at a bar in Phoenix called Cruisin 7th. As foreign as that bar was to me at first, I definitely belonged there. On a Saturday night, one would see all manner of girls: full-time transsexual girls and part-time crossdressers, young and middle-aged, petite and full-sized, white and Hispanic, and the retinue of “heterosexual” admirers. While I am attracted to all transgendered girls, it was the full-time transsexual girls that seemed to be the most interested in me.

After about a year, I came to believe that my foray into the transsexual dating scene was as much a distraction from my goal of a long-term committed relationship with a woman as crossdressing. Looking back, I’m not sure that my decision to stop dressing was a particularly honest or realistic one. If I had kept dressing, it’s likely that I still would have ended up at Cruisin 7th…except I probably would have been wearing a little black dress and pumps. As fun as that sounds to me now, I can live with my choice to go there in drab… and leave with a girl in a little black dress and pumps! During that time I met some very sweet, cool, smart, fun people. My only regret is that I wasn’t able to meet and spend time with more part-time crossdressers.

After moving to Tucson a couple of years ago, I met a wonderful woman who I absolutely love and adore. One of the best things about my girlfriend is that she is fully supportive of both my crossdressing and my bi-sexuality. Not only that, she finds crossdressing to be very sexy, and has even encouraged me to start dressing again! Sharing this part of me with my girlfriend has brought us a lot closer and improved our intimacy. Although I haven’t started dressing again yet, it is very liberating to have shared this aspect of me with someone I love.


En Femme Style

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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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Sam Davey
Sam Davey
14 years ago

Congratulations Serena, you seem to have found a semblance of peace in a turbulent time.

All the very best wishes

Sam xx

14 years ago

Dear serena, welcome back. I would say to you, don’t be afraid to begin dressing again, just go for it. If you have the support of a loving woman, I can assure you it will greatly enrich your crossdressing experience. My wife has been an avid supporter of my need and desire to express the woman within and I can say without a doubt that I wouldn’t be near where I am as a whole person without her. The relief I felt when she said that she would be with me as I explored and perfected my female side and… Read more »

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