By Jenn der Bentson

Crossdressing can be a tough topic. It can be tough to understand and that is no different for me, especially when I try to understand why I do it.

There are times that I like to dress as a woman. Yeah, it’s called crossdressing. I get turned on by it sometimes, so I guess there is a “fetish” factor in it sometimes, but it is also an escape. It is an alter ego that I slide in to and there are even times when it helps me work better, from home in my case, no one other than my wife knows about my alter ego.

But as we all, those of us who periodically dress as women even though we were born men, many times wonder, I wonder at the logic of why. What are the underlying reasons?

Of course, there are many. No psychologist worth their salt would tell us there is just one reason. And there may even be some just basic human nature that puts on varying points along sexaulity spectrums. There are no doubt benefits and detriments to this, and the goal is to leverage the benefits more than focus on the detriments, but I can’t help but wonder at one of them.

Do I dress sexy sometimes because my wife doesn’t?

My wife is an independent woman who works hard, although in job that by no means requires her to “dress up” for work. She doesn’t wear what a more traditional work stereotype from 50 years ago might bring to mind the image of a “working woman in her tight work skirt and blouse” even.

Interestingly, it is more common that I might decide to transition from my normal male self to my alter “Jenn” ego and dress in a stereotypical working woman attire than my wife! Under that I am more likely to wear 

Now, I am not saying my wife is unattractive or can’t be sexy, just that she doesn’t make an effort to dress in what might be a stereotypically thought of “sexy working woman” attire. It is more about function and daily reality for her. While in contrast, for me when I dress as Jenn, it is more about meeting that stereotype, or trying to my best ability to meet that image of what might be

I have an image of what “sexy” might be.

I have more negliges than my wife. I have more matching sets of panties and bras. Not that I have more bras and panties, but I make sure mine match. Hers are about function. Mine are about fulfilling an image, an expectation in my mind. There is certainly a difference.

For me, part of the effort is to be sexy, or at least what I think I can pull off as sexy.

It’s a sensual thing.

But how is this different for my wife?

For my wife, it’s everyday. Actually, it’s mundane, and avoidable at best.

For women, many times dressing up sexy is something they do for their significant others, to give them a treat. Not for themselves.

Most of us who have wives who tolerate or even embrace our crossdressing have had the conversation that they can’t wait to get home to take their bra off while we might say we can’t wait to get home so we can put one on!

To me, and many like me, its exciting to get dressed up and feel sensual. We feel different fabrics and cloths and year to have that “sexy” feeling.

Just being in “girl-mode” is enough to be sexy too. Its more than what we feel as guys.

Matter of fact, there is little about being a guy that EVER feels “sexy”. It just isn’t part of being a guy for most of us. So, we get that feeling by embracing an alter-ego.

Sometimes, I can’t help but think I yearn for this more because my wife doesn’t really dress in a manner that I consider sexy. I even feel bad about feeling that way sometimes. But should I?

I don’t know, but let’s come back to that.

Is there something in a guy, especially a heterosexual crossdressing guy, that yearns for sexiness in a woman enough that they even are willing to seek it out by becoming one to the best of their ability?

Many heterosexual males who crossdress would easily say if they were to ever become a woman permanently they would be a lesbian. That they love women. They think they are sexy, beautiful, sensual, and are attracted to them. Even when they are dressed as one or if they were one. This wouldn’t change for them.

Yeah. I get it. That’s me. 

I love attractive women. I love my wife. And some of the most turned on I ever get is when I am in my Jenn alter-ego and intimate with my wife. It’s almost a simulated lesbian experience.

I feel sexier in this lovemaking that I do when we have more traditional lovemaking sessions, even though I still love both methods and prefer one or the other version of myself at different times and for different moods.

But I come to the question. Would I crossdress as much if my wife dressed more sexy more often?

Would my wife dressing sexy fulfill my need for a sexy female presence in my life?

Tough questions.

But I honestly think the answer is that it wouldn’t help. I can’t blame her for a yearning I feel. It isn’t that she is failing to deliver some social expectation, its that I have a personal yearing to have that feeling of sexy that I think a woman might feel in a way that most men will never feel.

It’s a different feeling. It’s a different image. And it seems like it is something from deep in the brain, or maybe even heart. It is a hole that needs to be filled.

I don’t know that there is ever a way I can fully describe the difference in feeling I have between dressed in a sexy pair of panties and bra, stockings, a tight skirt and top, and having my wife come up behind me, press herself against me and run her hands up and down my hips as she presses herself close behind me. Even more differentiating is when she runs her hands from there up to my breast form clad chest and gives my tits a squeeze. That feeling is completely different than when I am not dressed up and do the same to her from behind, completely changing the roles. I feel sexy; something I don’t feel as a guy really.

Any man who hasn’t tried dressing up and reversing that role, embracing it and feeling it, has no idea what they are missing. To many of us, life would not be complete without that opportunity at least periodically. Unfortunately, with social pressures being what they are and social stigmas as major barriers to this experience, too many men who might yearn for this never get to experience this opportunity. I feel very lucky I get to.

But it puts it into a perspective for me. My desire to dress isn’t my wife’s fault. It isn’t because she is or isn’t doing something that leaves me with a hole in my life. It is a part of my life that happens as a natural course of who I am. And life wouldn’t be complete for me without it.

I can’t say that I dress sexy because my wife doesn’t, but I can say that I like to crossdress to feel sexy sometimes. It let’s me feel something that I don’t feel when I am in “guy mode”. I honestly, and this is a personal thing, wouldn’t give up being a guy, but I also wouldn’t give up being a “girl” sometimes either. In some respects, if my wife was dressed up sexy, while it would turn me on and want to be with her, it would also make me want to try to match her sexiness and dress up myself.

Thanks for listening to this audio post discussing cross-dressing topics. Hopefully the discussion helps others consider their own motivations or desires.