I'll Take The Man In The Dress

Reads: 185  | Likes: 0  | Shelves: 0  | Comments: 0

More Details
Status: Finished  |  Genre: Other  |  House: Booksie Classic
considering dating a cross dresser

Submitted: January 13, 2011

A A A | A A A

Submitted: January 13, 2011

A A A

A A A


I am so frustrated with this online dating thing. I'm getting nowhere with all these guys who want a woman to go hang-gliding, ice climbing, and traveling through the Himalayas with them. Or even just camping. Ugh! I'm a girly girl and I don't have anything in common with these guys. These guys like my friend \"D\" who complains that his wife buys too many shoes. Please! It's our God-given right as women to purchase shoes - are you going to deny us all pleasure in life? I'm so bored with the adventure guy I may have lost all perspective, but listen a moment to my new idea......

Granted it's a novel idea, literally novel because I got it from the novel This Charming Man by my favorite chic lit author Marian Keyes. But what if I were to date a straight male cross-dresser? It seems like we'd have plenty of things to do and talk about and he wouldn't even be gay. We would have so much fun together: shopping, watching reruns of Sex and the City, gossiping about fashion, make-up, and various celebrities, and of course having mad hot dirty sex. It's be like getting the best of both worlds - a 2 for 1. Now before you say \"ew\", let's try and get a little perspective.

Men look good in skirts - ie. the kilt - and I have yet to see a man out there with an unattractive pair of legs. Also we are all very used to the image of Tim Curry in The Rocky Horror Picture Show dancing and gyrating around in a corset and stockings. We are so used to it that he has become a cultural icon for goodness sake. Furthermore, straight women are allowed to dress up mannishly and not be considered gay so why shouldn't the reverse be true for men? And really, it's not that uncommon to come across a guy who likes to occasionally wear your panties as a form of foreplay. Finally, I think you'll find that the English, who are much more subversively kinky than us Americans, have been onto this straight-men-dressing-up-as-women-thing for ages. Taken in context it is truly not that shocking.

I surfed the net and did a little research and it turns out maybe my thinking was a little naive because it is actually a little more complicated than that. Case in point, dressing up is usually a sex thing for them. However straight male crossdressers are men who want a normal straight girlfriend who understands and supports them. They don't want to be women 100% of the time like transsexuals do, and they don't want to be with other men like gay men do. They are masculine in many aspects except that they have a real penchant for wearing women's clothing. This probably makes no sense to most people but it's not such a huge leap for me as I grew up around, and have always worked with, gender-benders. Granted a straight guy who desses in drag is a little more unusual but in their blogs these men all sounded like fairly normal, reasonably well-adjusted men who just had this little (alright, highly unusual) quirk. Could it truly be as simple as that or is there something darker at play that they are not telling us? And also hard to explain: if I am not gay or bi why am I so curious about men who dress as women?

Over all I am genuinely sympathetic and supportive however I will have to explore this whole thing a bit more and proceed with caution. There is definitely much I need to know because what if, God forbid, it turns out that straight male cross-dressers also prefer to fish, camp, and go hang gliding too - then they are not for me after all. And is it kinky? Sure! But I am feeling ready to get my kink on and it is time for something new.


© Copyright 2017 venusandmarz. All rights reserved.

Add Your Comments:

More Other Essays

Booksie 2017-2018 Short Story Contest

Booksie Popular Content

Other Content by venusandmarz

Popular Tags