Full question:

Dear Ibby, All I want to do is wear my girlfriend's clothes while we fuck. I'm straight, but ever since I was a kid, I've always had this intense fascination with women's clothing. Now, I finally feel ready to take that fascination into the bedroom. I love my girlfriend and I trust her enough to share this with her, but how do I bring it up in a not-weird way? Also, assuming she'd ever be down for this kind of fantasy (that, I'm unsure of) how would we go about pulling it off?

First of all, let me praise you.


Why? Because you didn't come at me all like, "What's wrong with me? Am I normal? Please validate me?"

Nope. Instead, you came up in here as shamelessly as you should, and asked not whether you were damaged, but how you could, in essence, be more yourself.

Love you.


In terms of bringing it up, you could always just leave a wanton pair of panties in an obvious place for her to find, and when she asks you "WHAT THE FUCK ARE THESE," you can blush, bat your eyelashes daintly and whisper "Mine."

Or, here's how I like to bring up my fantasies: during a moment of intimacy where you're both happy and comfortable, ask her what her sexual fantasies are.

If you already know what they are, ask her to elaborate on some of them for you, what she pictures in her head when she thinks of them, and how you could maybe make one of them into a reality. This does two things.

First, it gets you talking on the subject of fantasies and eroticism. Second, it shows that you're invested in her pleasure and her fantasies, which gives her an incentive to reciprocate that for you. Provided she's not a butt warlock, of course.

After you're done talking about her, she'll hopefully ask about you. If she doesn't, no worries, just begin with something like "I've actually had a fantasy I've been meaning to share with you too …" then … go for it my child. Spread your wings and mouth-hole and fly/communicate orally!

Explain to her what exactly it is that turns you on about women's clothing. Specify the scope of your interest and where you think it came from (if you don't know, that's okay too). Let her ask questions. 

Affirm that you're still as into her as ever, that your sexuality is unaffected by you interest in women's clothing, and that you're choosing to share this private information with her because you trust her and appreciate the emotionally intimate relationship you have.

Gauge her reaction.

Obviously, some basic chicks will take this badly. If she's misinformed, she'll shut you down or accuse you of "being gay" (false) or the killer in Silence of the Lambs (also false). If this is the case, she might just need an education. You might need to show her some films or TV shows about cross-dressing men (To Wong Foo, Transparent, Mrs. Doubtfire, fucking Mulan, and my personal favorite, David Duchovny in Twin Peaks) send her some articles (like this one), listen to some music by famous cross-dressing men (Bowie, Iggy Pop, Kurt Cobain, Young Thug) and generally try to expose her to what cross-dressing is and who does it. Hopefully, once she sees how normal it can be and how there's nothing fucked up or weird about it, she'll evolve from a lowly, ignorant caterpillar to beautiful, blossoming butterfly. If she's not getting it, dump her for her closed mind and outdated outerwear.

Other chicks will be okay with it, but will need some time to process it. You might have to just let it simmer, and be okay with that. Respectfully bring it up again when the time is right.

But, luckily for you, there are plenty of women who would positively squirt an entire ocean at the idea of this; who understand that there is something so alluring about a man tapping into his feminine side and being unafraid to truly express himself. Hopefully, your girlfriend belongs to this category of women. I really think more women should at least be open to things like this; that is, men coming out and asking for non gender-traditional sex acts. There's really nothing sexier than seeing your partner flex the full force of his sexuality and feel comfortable enough around you to do it.

However, keep in mind that even if she's into it, there are different levels of being into something. There's "That turns me on when we talk about it but I don't want to actually do it," and there's "Put on the dress I wore to Colin's wedding and lube your dick up." … And then everything in between.

Prepare yourself for these possible iterations, knowing that actualizing this fantasy with her might not look identical to how you envisioned it in your head. And that's perfectly okay. Fantasy, and the actualization of it, is a flexible negotiation between two people, not an all-or-nothing script that has to be followed or someone gets dropped in the shark tank.

Now, as for to how to actually pull this off? My guess is that if your girlfriend's into it, you could have a lot of fun.

First, and foremost decide what you want out of the fantasy. Knowing exactly what you want will make it a lot easier to explain to your girlfriend, and she'll be left with much less questions.

Some other miscellaneous tips:

1. Let her dress you the first time or two.

This'll make her feel like she's involved in your fantasy; like she's a contributing member of society.

Having the slight bit of control she has over you and the situation (in terms of wardrobe choice) might help her ease into it a bit, too. She's dressing you up; she's making you look how she wants you to. Therefore, you're not just thrusting this onto her and subjecting her to something she's inexperienced with — she's holding the reins.

Also, her clothes might not fit you. If she's got control over which ones you wear, she might feel more relaxed knowing your giant, pulsating biceps aren't going to burst the seams on her little sweater thing.

… Wait, are you thinking what I'm thinking? Let's say it together: Romantic! Shopping! Spree! 

I don't know how big or small you guys are. If she's tiny and you have to get on your hands and knees to kiss her and you're a hulking mega-man, I'd say yes. A romantic shopping spree is in order.

If she decides this is something she's down with, transition into you picking your own outfits in the future. Because bitch I know you're sick of her Sunday Casual look. Barf.

2. Let her decide if she wants to incorporate sex into the mix right off the bat.

Not all cross-dressing men find the practice sexual.

Some do, but only under certain conditions.

Some, like you, are raring to go. They find it intensely erotic, and want to fuck the crotch out of their panty house.

That's a beautiful image — trust me, I'm sobbing — but if she's feeling any hesitation about all this, leave sex out of it the first time you play dress up. Just let her dress you to her liking, maybe throw on a little mascara to make your eyes pop, do each other's nails, order a pizza with a bunch of sausage on it, and just … hang out.

It might be frustrating to you to get so close to a fantasy without actualizing it, but at least you'll get some good jack-off material, right?

Sex is something you have to work up to regardless of whether what you're doing is vanilla, kinky, or a full-on Urban Outfitters Women's New Arrivals fashion show (which is what I imagine your girlfriend's closet is like), so take things slow and know that the more you respect her boundaries and comfort level, the better the sex will be if it actually happens.

3. Figure out how far you want to go with the gender roleplay before you start.

If your girlfriend is new at this, she's going to have one question: who's the girl?

Of course, this question flies far below the elevated conversation of how arbitrary traditional gender roles are, and how neither party has to be the "girl" or the "guy" for sex to be awesome.

But, nevertheless, she'll probably want to know how to approach you and what you want her to do. Is she the guy now? Are you both the girl? Is one of you gender neutral? Where the fuck is my cell phone charger?

Figure these things out beforehand. Ask yourself how far you want to go with the gender roleplay. Do you, the typical penetrator, want to get penetrated for a change? Does the scope of your gender play transcend physical appearance and dive straight into sexual functioning? Or, do you just want to fuck her the same as you always do, just while wearing her clothes?

Something in between, maybe?

Also, about your dick. Will you be tucking your dick? Or letting it frolic loosely into the ether? Should she focus on it in the same way she would if you were donning your regular "man" presentation, or should she touch you like a lady should be touched?

These are the questions we ask ourselves.

Make these distinctions beforehand and work with her to find out what part about you cross dressing she likes, or finds sexy, and come a meeting point where you're both comfortable playing your respective "roles."

4. Return the favor.

She stuck her neck out for you and embraced you as your most authentic self, now you stick your neck (and dick) out for her.

Alright, well, now that I've written my first novel, I just want to tell you that you're killing it, I hope your girlfriend fucks the shit out of you while you're both in her heels, and if she doesn't, I have a really satin-y dress that would look great with your aura.