The life of the teenage crossdresser

I just discovered the blog “Being a teenage crossdresser,” which is about:

The pleasure & difficulty of being a teenage crossdresser and more. I ain’t just a crossdresser, i have a life aswell. This blog just keeps my diary of all events, not just crossdress related ones.

It’s written by Alice, an 18-year-old student, who can read more about here.

Photo via Flickr

Here’s a sampling:

When I cycled in for my lecture later, I decided to bring some cash so that I could waste time (and money) in the city while I wait for my presentation. The lecture was interesting but I knew most of it. I walked to town through a beautiful and ancient path designed for the students for my very purpose. I had nothing that I wanted to buy; I only wished to peruse what was on sale. I walked around the market for a while and then went clothes shopping. The thrill of walking in the women’s section of a store is something that only crossdressers know. The excitement of the forbidden and the lure of the pretty things.

I feel extra special, for I have a deep belief that it shouldn’t be forbidden. For me, the act is a rebellious one. I am saying ‘yes I am a man, and yes I like women’s clothes’. We should be able to buy what we want, not what is prescribed for us by sex, fashion or anything.

My mini rebellion went unnoticed and I started the walk back to university to give my presentation. The pre-stage jitters were starting in my stomach. I was hurled back to my GCSE Drama where I was frequently forced to perform. I used to love this feeling. It is anticipation mixed with dread, mixed with the glory of completing it later. I was in a musical or two in my last school but I was on anti-depressants and as such, I didn’t feel too many emotions.

Now I feel it more than ever. It was almost erotic how I was paralysed by fear and excited at the same time. Angela Carter in her infinite wisdom wrote about the stage in her novel Wise Children. Among a multitude of quotations I could use, the way she describes the wait for the curtain coming up is the most powerful for me. ‘We were wet for it!’ Simple and beautifully true. All erotic symbolism of the theatre aside, it was exactly what I was feeling about giving a presentation to my discussion group (a slightly less romantic setting).

Alice also has a link to a fabulous page of information called Speaking of Crossdressing, which answers questions such as Why do people crossdress? and How do you supplement your bust line? Here’s a snippet:

Are you trying to pass as a female? “Passing” is a big deal in the crossdressing community and it shouldn’t be. Many CDs sustain a fantasy about passing, I suspect it’s because they imagine they won’t be noticed and thereby held accountable for their actions. The makeup becomes a mask, providing anonymity. So they wear short skirts, fishnet hose, and 6″ spike heels at the mall! Go figure. Those who have a brain in their heads will dress with a certain degree of age-appropriate style and panache, always looking nice; so even if they are “clocked” others will respect them for maintaining an aura of decorum. I want to project as nice an image as I can, so I go the extra mile with hair, makeup, figure enhancements, etc. Many people still see me as a man in a dress, but at least they see a stylish, fashionable man in a dress. In reality, most folks are just too self-absorbed in their own worlds to notice or care much at all about the people around them.

As far as I’m concerned, it’s not passing I’m after – it’s acceptance or, at least, tolerance. That puts the onus on others; if I get clocked and the observers still treat me with respect, they pass!

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4 Responses to “The life of the teenage crossdresser”

  1. Alice Says:


  2. Alice Says:

    i have just realised that i bought your book about a month ago…

  3. Donna Queen Says:

    Which means you haven’t read it yet…. Wonderful blog, honey!

  4. Donna Queen Says:

    Alice’s blog is terrific, and I applaud her work without reservation. The link to Lacey Leigh’s informational page, however, merits closer scrutiny. Ms. Leigh is closely associated with Tri-Ess, which describes itself as “[a]n international social and support group for heterosexual crossdressers, their partners, the spouses of married crossdressers and their families.” On its website, Tri-Ess proclaims, without a shred of supporting evidence, that “the vast majority of crossdressers are ordinary heterosexual men…” Ms. Leigh makes the same bald assertion on her site. From its inception, Tri-Ess has promoted a divisive, homophobic agenda designed to soothe the anxieties of its deeply conflicted membership and keep them from experiencing full-blown homosexual panic. Transgender writer and educator Lynn Conway has this to say about the pernicious character of Tri-Ess:

    Tri-Ess’s founder, Virginia Prince, was a frequent speaker about “sex and gender” at the early medical conferences on transsexualism in the 1960’s and 70’s. Prince portrayed transvestism as a “love of the feminine” by normal heterosexual males, to differentiate them not only from “ordinary” homosexuals but also from transsexuals, who were thought by most behaviorist psychologists of the time to be an extreme form of homosexual…

    Prince’s talks implicitly exploited transsexualism as a foil to elevate the image of transvestism by characterizing it as having higher, purer, more intellectual motivations. Since those talks echoed and reinforced the old paradigm that transsexualism was “about sex” (and in particular “gay sex”), Prince’s views were taken quite seriously by many male psychiatrists of the time.

    As a side-effect of that activity, Prince embedded an intense homophobia and transphobia into Tri-Ess culture where those phobias still linger today. One senses that the internal feelings of shame and embarrassment felt by many Tri-Ess crossdressers have long been eased by proclaiming “I may wear dresses, but at least I’m not a faggot or a sex change”. In addition, the Tri-Ess exclusion of TG/TS members may also be designed to calm fears of members’ wives and girlfriends that their men may be tempted into “homosexuality” or even into transitioning if any TG/TS women managed to get into Tri-Ess.

    Exclusion from many CD clubs presents a problem for young TG and TS girls who try to enter the crossdressing scene early in their transitions, thinking of that as a way to “try out their wings” at gender crossing. Some even initially think that they are just CD’s, and only later sense their deeper gender issues. Occasionally a young TG/TS girl just coming out to herself may try to join Tri-Ess, thinking that she might find help there. This can lead to awful rejection, and can damage a young TG/TS woman’s feelings at a most critical time in her life. Therefore, young folks who think there is any chance they might have transgender or transsexual feelings are strongly advised to NOT join Tri-Ess, but to seek other more inclusive CD clubs that openly welcome TG/TS people. Of course, transvestic men who want to join a CD club that only includes other “normal heterosexual men” will feel very much at home in Tri-Ess.

    Read more at:

    I hope Alice and other young TGs heed Ms. Conway’s warning and approach organizations like Tri-Ess with extreme caution.

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