A Personal Journey Into Gender-Bending Fashion

A Personal Journey Into Gender-Bending Fashion

I would say that I am a pretty open-minded individual when it comes to fashion and lifestyle, but until recently had no experience of trying on clothing that would normally be labeled "feminine".  I am a young, somewhat introverted guy, so I rarely go out to big social venues, but I still enjoy having parties with a few good friends at my place to have fun, that kind of thing. If you were to ask me three years ago how I felt about cross-dressing, or even wearing something similar to women’s clothing or underwear. I would have flat-out said “No!”  Even though, underneath you could usually find me wearing an extra-small pair of Calvin Klein briefs. Just like several others growing up, I started out wearing loose boxers, never briefs, and never boxer-briefs (I could never stand wearing Hanes or Fruit of The Loom.)


During High School, I grew tired of boxers in search of something new, something sexier, something that I could buy and emulate as expensive, and that was a Costco pair of Calvin Klein briefs. I know what you’re thinking, but I had thought that I was the most attractive person in the world, and that everyone would want to have sex with me once they saw the words “Calvin Klein” going across the waistband of my underwear. I know I did every time I saw myself in the mirror. Over the years, I had transitioned into bolder colors and shorter cuts with my underwear, more briefs, some thongs, and a few bikinis. One year, I had even bought a pair of bikini string briefs. I would wear them to school or elsewhere, pulling up the strings, and bringing them up past my thighs to hear them snap was always a hot feeling for me.



All the while, I still had no interest in trying anything that couldn’t be considered masculine in some way. It’s not that I didn’t like anything with a feminine vibe, I was actually always fascinated by the variety in girl's panties, and maybe somewhat jealous of women's clothing options, since the accepted options for men were the drab choices of black, grey, or white, boxers or briefs. While jealousy was at play, I still wanted to accentuate my masculine features. Even though when I was younger I would wear boxers. I always felt more comfortable in something smaller and tighter, despite growing up with a mother who always bought my clothing in sizes that were three sizes too big. I’m a small guy, well sort-of. I’m 5’11 and about 130 pounds, but I’ve always been skinny compared to other people. So having small, yet tight clothing has always felt right for me.


It was Christmas of last year that someone special had gifted me a set of lingerie from XDress. At first, I was somewhat confused about the gift, since I had never worn such feminine pieces. However, my friend, who actually has a small underwear fetish, had given them to me thinking that they would look sexy and fitting on me. The first in the set was an extra-small, red lacy thong. I felt a little flustered pulling it out of the box. The next in the set was a black stretchy bodysuit, which I really liked because I had wanted a leotard or bodysuit of some kind for so long.



As soon as I tried it on, it accentuated my body and had lifted my small (but promising) butt. One of the more special things about the bodysuit is when you’re fully erect; it shows the silhouette of your goods just right. Lastly, in my Christmas gift was a pair of laser cut, floral, blue boy shorts. My friend had actually bought them a size too big for me, so now I just wear them around the house casually; it’s a good feeling for wanting to be stripped down but not being naked. This Christmas gift had shifted my entire spectrum for underwear, from beginnings as a boxer-wearing baby all the way to gender-bending eroticism.


 After all of those gifts, trying them on, taking them off. I was really using them to create a new personality for myself. Like I said before, even as a modern and open individual, I was never really interested in wearing feminine pieces. However, once I slipped them on, I noticed how good my body looked.  It gave me that extra little lift that I've been looking for, and seeing that foreign color really made my eyes pop. All of the reservations that I had went away. Now I’m beginning to see underwear and even clothing differently. At the “late” age of twenty-one. Inviting more genderless pieces into my wardrobe, accepting pieces that I don’t label at all - I just wear them. Sometimes you have to do just that, and not give yourself a self-acceptance speech, but simply put it on. For me, it’s not even really about what the piece is saying. It’s more about my gut feeling, really wanting to try something out-of-the-box and actually doing it without completely stepping out of my comfort zone.



Ultimately, it’s about taking the next step, embracing some different styles, trying on that pair of panties (Or even boxers, If that’s what you’re feeling), they might look good on you. I think a lot of us can agree that we’re seeing more and more transitions into feminine fashion; the rules are beginning to fade, even though some of us may never have even thought of it to begin with. Either way, its fun, its flirty, its one hundred percent OK, and this is coming from someone who once thought Wal-Mart bikinis were sexy and high fashion.

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Love this article! Very insightful. The exploration from men’s underwear, which is far too boring, to panties is a journey all of us have gone through and all at different times. But, be thankful we made the transition! Men’s underwear, while still a small part of my repertoire, is just so boring although some improvement has been made in the last 20 years. XDress still offers a better selection of panties and the styles are very sexy and offer more style! The way they accentuate your body is probably the best part! I also agree that women’s clothing is so much more appealing than men’s. The materials are more flowy and stylish but I must admit that the woman’s body is just so much more sexy than the male’s. I like that as a society we are progressing forward and more accepting of individual choices. Be daring! Be flashy and wear what you want, when you want!


I have always wore lingerie for 2 reasons. 1 to feel sexy and comfortable and 2 to enhance lovemaking. Although wearing sexy lingerie when involved with a woman is exciting and pleasurable; it wasn’t until I experienced sex with a man who loved his partners in lingerie that the fascination of lingerie burst in to life. Perhaps only a man, whatever his sexual persuasion, can appreciate the attraction of lingerie in lovemaking. In my case he was a doctor who I met in a pub. Back at his place our first encounter was rough and ready but there was enough of a spark for us to continue seeing each other. After a few trysts, he revealed that men in lingerie hugely turned him on and asked me how I felt about that. I saw it as an opportunity to enhance an already enjoyable sex life. It did! He first bought me some very feminine nightdresses but we quickly moved on to more intimate apparel. The effect my wearing thongs and stockings had on me let alone him was amazing. Needless to say I knew my place underneath (Although that wasn’t our favourite position) and thoroughly enjoyed our steamy relationship. Long since married I still occasionally stray on to the “dark side” when the occasion arises. The thrill of a man doing to me what is done to a woman is made all the more exciting by the lingerie I’m wearing at the time.


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