Dudefile #97 – I Just Found Out My Dude Wears Women’s Lingerie

Dear Dude,

Recently my boyfriend and I moved in together.  We’ve been dating for nearly two years and I couldn’t be happier to be with him.  We have always had a lively sex life and I think it is one of the things that keeps our relationship strong (ie, we WANT each other).  

So here’s my problem: I recently found out that my boyfriend likes to wear women’s lingerie sometimes.  When we were in the process of moving I stumbled upon an overnight bag, and when I looked inside I found some women’s panties and other clothes, like skirts and stuff.  I confronted him about it because I assumed they must have belonged to his ex-girlfriend and I was pretty pissed thinking he had kept some of her stuff!  But since I was clearly getting worked up, he confessed that they were his.  He was really embarrassed and I felt terrible for pushing him about it.  I told him I love him unconditionally and he can do whatever pleases him.

BUT I am a terrible snoop (I feel pretty ashamed actually), and when he wasn’t home I looked through the bag.  In addition to ladies’ underwear etc, I found some papers and a notebook filled with his writing, in which he had scrawled pages and pages of really filthy sexual fantasies.  Most of which describe gay sex.  Now, I really don’t mind much about the dressing up thing.  But what seems to bother me the most is the possibility that he might have some strong hidden desires to be with a man, which means that I cannot fulfill him.  I’m  by no means a prude, but I also am upset by these pages and pages of fantasies that he’s written out because some of them are kind of violent and shocking (to me at least), and he seems to have some obsessive drive in writing this stuff down.

I think I can deal with some occasional cross dressing, even though I don’t understand it, as long as I feel assured that he is truly committed to me and desires ME (which I do).  I am NOT suggesting that I think he is a closeted homosexual, but he definitely does have some desires that defy gender norms.  And some of those desires include sucking another guy’s dick while wearing women’s lingerie.

I feel kind of guilty for writing to you about this, I know my bf is really embarrassed and ashamed I found out, but as far as he knows I only know that he wears women’s clothes sometimes.  I feel really torn up about this.  I would appreciate anything you have to say, because I don’t feel like there is anybody I can talk to about this.


Worried Girlfriend


Hi WG,

See, this is where snooping gets you. One day you move in with your super perfect boyfriend, the next you have a bed covered in extra, extra large panties and a head full of scandalous tales stuffed with images you can’t unsee. 

Anyway, look. The DW is with you about the ladies garments. Whatevs. So, now sometimes when you enjoy the sweet pleasures of lovemaking you’re both wearing thigh high hose and frilly thongs. Best case, it ends up turning you on just as much as him. Worst case, you’ve made your dude wildly happy and earned the right to have him act out that Comic-Con nerd fantasy you’ve been thinking of where he dresses up like Wolverine and has his way with you right on Charles Xavier’s desk. Or pees on you. Or whatever your thing is. 

Most dudes have some sort of fantasy about pushing boundaries. The DW suspects most women are all too familiar with everyday versions of this where a dude is forever trying to put something in your butt or talk you into blowing him on video or asking you to say something naughty like you mean it or “accidentally” spraying his goo somewhere you’d rather not have it.

But all sorts of dudes, like yours, have other fantasies that are a little more specific, adventurous, unexpected, filthy, shocking, pick your word. Some dudes will hop on in and say, “Here’s the deal. I likes me some fuckin’ in full body panda suits with just a little area around the balls cut out. That’s who I am, get used to it.” Others, for a variety of reasons, will take their crusty, matted panda costumes secretly to the grave. 

And normally this is where the DW would end the letter with a joke about balls and tell you to relax, be glad you brought this out into the open, and move on. Big whoop. Who cares. Just feel lucky your dude isn’t into poop. Enjoy sharing outfits!

But in this case, the DW is going to suggest you do cop to your snooping and talk to your dude about how he feels about cock. Two reasons.

One, you know the things he has written and you are troubled by them and your brain is going to keep turning that shit over and over until you reach some conclusions that may or may not be accurate and could potentially put a real strain on your conscience and the relationship.

Two, while you might be surprised how many dudes would have a go at sucking a dildo, there are approximately zero straight dudes who want an actual human cock anywhere near their face. It would be helpful for you to know if your dude gets off on the thrill of tiptoeing right up to the line of mansex or if sex with men is something he wants, in reality. 

Because here’s the thing. If tiptoeing up to the line is his deal, you two can have a fucking field day with some toys and some lubes and some imagination. But if real world dude on dude action is part of what he desires, that’s a bigger conversation. 

Is your dude gonna be pissed? You betcha. Snooping sucks. And sounds like he’ll probably be ashamed all over again, which isn’t any fun, either. Just do your best at looking non-shocked and ask him to help you understand where he’s coming from with his fantasies.

Best of luck,

The DW

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5 Responses to Dudefile #97 – I Just Found Out My Dude Wears Women’s Lingerie

  1. Wow DW, this one’s a doozy. Good advice, though. She definitely needs to talk to him about the fantasies. I don’t know any straight guys that are into man-on-man action, either. I’ve had one friend and one acquaintance who chose to ignore “signs” of their man’s sexuality. One wound up divorced after two kids and the other is in the process of a divorce. Oh, and can we talk about Author Terry McMillan and her divorce fiasco?

    Honey, do yourself a favor and get to the bottom of it. Find out what’s really going on and then decide what you can and can’t tolerate. Do it now! Before you get your life and your heart any more entangled with him.

  2. nir says:

    Or he could be bisexual.

    • Definitely. That’s one of the things WG’s conversation needs to be about. Bi might mean they need to rethink their relationship, or bi could just be another thing she knows about him and they keep on movin’ on as they were before. All depends what shakes out.

  3. MJ says:

    That IS a doozy….but the DW handled it with his usual good sense and flair. But leaves me with the burning question–if I don’t have anything to hold over my boyfriend, how do I get him to dress up like Wolverine and have his way with me?? That sounds pretty hot.

  4. I wanted to dress my husband up as a shirtless firefighter and play “Save the Baby from the Brownie & Roses Fire,” but he didn’t go for it.

    Solid advice as always, with just the right amount of dick jokes.

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