By Jenn der Bentson

“I just feel sexier when I am dressed as a woman,” I expressed to her “Guys just aren’t sexy, and when we have sex, I feel like I want to be sexy sometimes.” It was kind of a way of expressing what I feel about why I like to crossdress sometimes.

If I am honest with myself, crossdressing is actually part fetish for me, because it turns me on, but it is also part relaxation, diversion from my normal personal, and expression of another part of me also. I like crossdressing as a break from my normal role as a man, it lets me express a part of me I normally don’t express, and it hasn’t gone away throughout all of my life. It isn’t just  a passing curiosity or fancy.

As a guy, and as a part of societal expectations, I express myself in a manly way. As a guy, I don’t get to dress in interesting, fun, or sexy clothes. And I certainly don’t get to have boobs.

Dressing as a woman lets me express my tastes in shopping, wigs, makeup and shoes. It is something that isn’t a “guy thing”. For me, it’s just an “at home thing”, but that’s enough for me. And I would be lying if I said the feeling of breast forms on my chest in a bra or glued on, having boobs, wasn’t awesome. That is probably the most “guy thing” I have about crossdressing. That is more of the fetish side of crossdressing for me and I hazard a guess there are others out there like me.

I know not all are, but I am a heterosexual crossdresser. I have no desire to transition. For me, crossdressing is a periodic expression of a part of myself. As such, it likely explains part of my love for the feeling of boobs on my chest. It is part of the feminine image for me and part of feeling of sexy that comes with dressing that is missing as a guy.

Guys don’t get to feel “sexy” and I think that is something missing for many, even if they don’t know it. They are expected to be “manly” or “buff”.

Those thoughts come with the challenge of wanting to express myself and dress in femme form at times. And the feeling of sexiness that it generates when I do comes with the mixing of expression of my feminine side, and sexual arousal that it generates, for my male side as a result also. Those things intertwine into a frequent desire to satisfy sexual urges when dressed. It’s a weird thing to try and untwist, but those things get mixed up together.

Ok, this is confusing, I get it.

I am not saying dressing up makes me get turned on at myself and I want to have sex with myself, I am saying that feeling sexy, something that doesn’t really happen the same way as a guy, is an arousing feeling. In my case, it doesn’t change the fact that I am heterosexual, and as I feel sexy, I feel a friskiness for my wife, who even I am dressed as a girl at the time, is who turns me on.

Fortunately, she is accepting of my female dressing activities an gets a kick out of it too, and the obvious benefits of my friskiness at times for her as a result. But this is surely a confusing moment that is generated for anyone in this situation. 

It puts gender roles in flux, it may put a wife or girlfriend in the position of seeing their significant other dressed enfemme and not being as attracted to “a girl” as they are naturally to the “man” in which they are in a relationship with, and that same sexy feeling and friskiness may not work for them as much as it does for the guy who is dressed enfemme at the moment.

There is a reality there that must be discussed and worked through in a healthy relationship. Sometimes, it isn’t something that is going to work for both parties.

But that also doesn’t mean that it can be tamped down and erased from the desires of a guy, like me, who has that feeling of need to dress in female form sometimes. Without doing so, I honestly feel like something is missing in my life.

There are lots of reasons a guy may want to dress enfemme periodically, or even more frequently, but for me one of these includes the feeling of sexiness it can generate. It isn’t a natural male feeling, it isn’t manly, and it isn’t what society typically expects of a guy. But that doesn’t mean it isn’t a desirable feeling or one a guy should withhold from their life experience.

Women are generally considered more sexy in most cultures around the world. Their expression of femininity, how they carry themselves, how they dress, and how they look is synonymous with it. Experiencing that for them, is natural more than it is for a guy. But a guy who takes the time to dress and works to express femininity can experience a little slice of that and the feelings that can come with it may even be a little bit of a rush.

To some degree that sexiness when dressed enfemme for a guy is taboo, and taboo things come with a little adrenaline rush. I am sure that feeling helps the desire to want to do it again become stronger also. Endorphins and adrenaline form some natural high that humans seek when it’s safe to do so. It becomes a desire circle to experience it again.

Sexiness can be intoxicating. I know it is for me, and it is certainly one of the factors that drives my crossdressing.

If it does yours too, know you aren’t the only one.