Boyfriends Who Look Like Girlfriends: Crossdressing, A Double Standard

person wearing pair of white girls rule text printed socks
Photo by CoWomen on

A couple years ago, I read a book called My Husband Betty, about Helen Boyd learning to cope with her husband’s cross dressing. Back then, I knew very little about cross dressing, but my knowledge repertoire rapidly expanded as I delved headfirst into this page turner. Betty quickly became a favorite guilty pleasure the day I checked her out from my university’s library.

The book began with a description portraying the double standard** of how it’s considered sexy when a woman wears men’s clothes, but not vice versa. If a woman rolls around on a bed wearing nothing but her male lover’s button-down shirt, it sounds like the description of a perfume ad. We say she’s sexy, she’s sensual, and she’s acting out of love. In contrast, if a man did the same thing for the same reasons, wearing nothing but his female lover’s satin dress slip, it would be for grins. People would laugh at him, they’d ridicule him, and they might even threaten him with physical violence.

Gender is a social performance.

What’s between your legs is there by nature, but how you recognize and express your own femininity and masculinity is up to you. What it means to be “feminine” and “masculine” are both social constructions, and you probably learned them early in life.

selective focus photography of three disney princesses figurines on brown surface
Photo by Jennifer Murray on

I’ve always been a girly girl, yet I, myself, cross dress frequently. On weekends, I practically live in men’s undershirts; I have a few pairs of men’s jeans which I love to wear cuffed on spring and fall afternoons; and I even wear men’s boxer briefs, both as yoga shorts and occasionally as underwear. For me, cross dressing is very much about comfort in the garments themselves, but there is also a thrill in exploring my own sense of masculinity, as well as in owning garments which I’ve come to associate with my favorite parts of past lovers’ bodies.

Cross dressing has a bad reputation in the American media because of the gender dichotomy we strictly enforce on one another each and every day. We chide women for acting “masculine”, but more often than not, it’s men who behave in ways we call “feminine” who face much greater social stigma and physical and emotional threats. It is unsurprising that some women would strive for greater, more masculine social power, yet it threatens the patriarchy when a man is caught forfeiting — even temporarily — any of his “natural” masculinity. But, we all need escapes from social pressures sometimes, and cross dressing is one way many men find a sense of release.

I would love to date a cross dresser.

I think it would be thrilling to get dressed up together, as a new set of experiences to share with someone I adore. I don’t doubt that I will likely encounter a number of the same trials and tribulations as Ms. Boyd (particularly the annoyance of how expressing one’s inner femaleness is so often in the male mind equated with preadolescent fantasies of stereotyped promiscuity), but I am intrigued nonetheless. The trust, the intimacy, the gender bending…!

Being completely honest, I think it might be a little awkward to see a significant other wearing any of my lingerie — at first. It’s something I’ve never experienced before, so I could see myself having a knee-jerk reaction initially. But, with that said, I would also love to share such a special experience with an intimate partner. I can’t help but feel like there’s something inherently sexy about the juxtaposition of a man’s strong body being enveloped by the same silk and lace I admire on my own feminine form. There’s a certain thrill to deviation, after all. Why not have a little fun with it?


**The full introduction (or, at least the first few pages which describe the double standard I’m borrowing) can be read here on Amazon. Just click the “Look Inside” option by the book’s picture in the upper left corner.

In case you’re on the fence about checking it out, I highly recommend this book! Buy it, borrow it from a library, whatever… It’s an informative, well-researched, eloquent, empathy-envoking read for anyone who has ever been curious about the ins, outs, history, psychology, and much more about average, everyday cross dressing.

10 thoughts on “Boyfriends Who Look Like Girlfriends: Crossdressing, A Double Standard

  1. This was a completely alien viewpoint to me, which is why I think you’re so awesome. I am very accepting of cross-dressers of all stripes, although I have never done it myself, but I never really thought about the double standard. I find it very sexy when a woman wears a football jersey or a hoodie that’s way too big, so I totally understand why a woman would find a guy wearing some satin lingerie sexy. Too cool.

    Liked by 1 person

  2. I love this. As a maker of bespoke undies, I hear all kinds of stories and get all kinds of requests, but I love the gender bending requests most. There is just something so liberating about them. But sometimes too, they also feel shrouded in shame. It’s such an honor that folks would trust me with such an intimate part of their lives. And I look forward to a day when the boxes we’re all forced to live in get a little less boxy.


    1. Amen, and I love your attitude! As soon as I started scrolling through your awesome, hand-made undies for sale on, the thought crossed my mind of the variety of requests you must receive. I wholeheartedly agree that gender norms are much too restrictive in this society, and I’m thrilled that so many people have created opportunities to make the most out of breaking those norms.


      1. Yes! Pushing a boundary a little bit here, a conversation there, and on and on and that’s how the world changes. It’s thrilling to both play an active role and to create a space where others feel safe breaking down gender norms! Here’s to being a member of such a great club 🙂


  3. I’ve never had a desire to wear women’s clothing, but have often wondered why men’s fashion choices are really so limited. We have business suits, casual suits, sweatshirts, t shirts, blue jeans, khakis and knee length shorts. Our underwear is thighty whiteys or boxers, all of it very uninspiring and certainly not sexy. I get why some guys wear women’s underwear. The colours, material and cuts are fantastic. Depending on the underwear a women wears she can emit a powerful sexual message. You can often tell if a women is wearing sexy underwear, her strut is different, she moves along exuding sexuality. When it comes to the bedroom, the women removes her clothing but gets into bed with her underwear. The underwear and it’s removal becomes a part of the love making ritual. The guys simply drop their clothing and get into be naked. It seemed to me unfair that men did not wear fantastic underwear and get that sexy feeling from the clothing. Over the recent years I have begun to buy and wear sexy underwear for men. I love wild colours, fantastic materials such as satin and lace, and cuts like thongs and G strings. I stand in front of the mirror when I put them on, and I like what I see. There is such a huge difference between boxers and a lovely lace thong cut for a guy so all the parts fit properly. When I go to the grocery store, I feel great and sexy, and no one knows why, but I stand up straighter and move with more grace and I think the ladies notice cause there are more smiles and more niceties expressed. I think that being sexy starts with feeling sexy and that goes for both men and women.


    1. I absolutely agree, and good for you! Sexiness exudes from the inside out, and it’s important to take time to find ways for each of us to appreciate ourselves and our sexual beinghoods. Like you, I find some of that inspiration from underwear. It’s exciting to be able to try different fabrics on those oh-so-sensitive body parts than what is worn elsewhere on your body, and because these garments are hidden, it’s like your own little secret. I believe that society as a whole would be more pleasant if handsome underthings which make people feel great about themselves were not limited exclusively to cis-gendered women. I wish men’s clothing came is softer fabrics and more color options in general, but I would especially love to see more men enjoying fun underwear that they picked for themselves, rather what their mothers and significant others have bought them over the years.

      (For any guys looking specifically for men’s bikini and/or lace underwear made to fit male curves, check out A roommate and I stumbled on it last year and spent hours admiring the garments in the “thrill” section. The pieces are mesmerizing…)


      1. Amazing, that’s exactly were I get my underwear from! They have great service, and I have not been disappointed. As I began to explore all the varieties of fabrics, cuts and colours I was really surprised at the level of pleasure I got from actually buying sexy things for myself, it’s something that most guys don’t do. I suppose that men get that thrill from cars or bikes etc, but it is quite different when you buy something that really enhances (shows off) your sexuality. It is very different, I still feel a bit of excited shame about wearing nice things. Men too have had their sexuality really repressed but society in general. It is odd.


        1. Glad to hear that Freshpair’s quality and service are all they’re cracked up to be. I’ve never ordered anything from them for myself, but now I know where I can buy sexy undies for my next beau 🙂

          I’m not sure if men’s sexualities have been repressed, per se, but I would certainly agree that they have been severely constricted. Sadly, the “man box” doesn’t allow for much wiggle room to be a real person.


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