July 25, 2012

I am a hetero female, but one of my biggest fantasies is for a guy to dress up in women’s underwear. Not full-blown drag, just a teddy, fishnets, and some heels. He doesn’t even have to act like a woman. I just want him to parade around a bit, and just for me. I’ve had the ovaries to bring this up only twice to men I’ve been with. My first boyfriend was game, but I was so insecure with my sexuality at the time that I let it go. My second boyfriend found it degrading and wouldn’t do it. I think there are two things holding me back: 1) I’ve never even heard of this fantasy, and that makes me feel like a creep. Is there a name for it? 2) I know the first time, I will giggle with joy, and I’m afraid that will be a big buzzkill if my hypothetical future boyfriend thinks I’m laughing at him.
Lingerie Without A Man

1. There isn’t a name for this fantasy, LWAM, so let’s come up with one. How about “Frank-N-Furter-Ing,” for Dr. Frank-N-Furter, a noted research scientist who also enjoyed dressing straight boys up in fishnets, teddies, and heels? Your fantasy probably lacks a name because it isn’t that odd, or a whole lot to ask. And this fantasy makes you more sexually and romantically marketable than you seem to realize, LWAM. The world is full of men who aren’t gay, aren’t into drag, and aren’t into full-blown crossdressing, but are turned on by the idea of wearing the girlfriend’s panties and/or a little lingerie. A lot of these men are with women who barely tolerate their kinks. The single ones, on the other hand, are out there looking for a girlfriend who is turned on by the thought of a guy in panties, teddies, fishnets, and heels. Post a few explicit personal ads on online dating sites—kinkster and normster—and I promise you’ll be flooded with responses from guys who want to put on a show for you.

2. It is permissible to giggle during sex. If you’re worried that your partner might think you’re laughing at him, qualify your giggles in advance. Explain that you’re prone to joyous laughter when you’re turned on, and you might get a little giddy during his performance. Emphasize that your giggles are evidence of arousal, not disgust or contempt. Then prove it by fucking the shit out of him.

3. Have you checked out xdress.com? Think of it as your own personal porn stash before you find a boyfriend, and your favorite online shopping destination after.

He is completely resistant. It is ironic that the pill protects me from pregnancy if I have sex, but we’re having less sex due to the weight gain, bloating, bleeding, no sex drive, and other side effects. My doctor does not think other options for birth control (e.g., an intrauterine device) will be a good fit for me. Should I continue on the pill, or tell my husband that if he wants sex, he has to share responsibility in avoiding pregnancy?
Tired Of Pills

Shared responsibility.

And you can keep having sex without pills, condoms, or pregnancies. There’s oral (his-and-hers), anal (ditto), and mutual masturbation (underrated). But if it’s vaginal intercourse he wants, then he’ll have to get used to condoms. Some women can’t take hormonal birth control, and your husband is married to one.

It was safe for the bottom—provided that overtaxed condom didn’t burst (here’s hoping they were using a more spacious, more durable female condom)—but it wasn’t safe for the tops. Jamming two dicks into a single condom could result in dick-to-dick transmission of a number of sexually transmitted infections—herpes, HPV, chlamydia, syphilis, gonorrhea, etc.

My anger comes from his timing. If he had told me this before we had sex, Dan, I would have been able to have a constructive conversation about this. The problem now, if I’m being completely honest with myself, is that I really like him and I don’t want to stop seeing him.

A couple of questions: Do I reach out to him again? Did I overreact?
Left In The Lurch

I can understand why you were upset. You had already taken things to the “next level” in your heart—you were thinking of this guy as your boyfriend—you just hadn’t gotten around to informing him about the upgrade. And you assumed that, when you did get around to letting him know, he would be delighted. Because he was the one who wanted a relationship at the beginning, right?

Unfortunately, LITL, he took you at your word when you said you weren’t interested in a relationship. Keeping things “purely casual” with you meant he was free to pursue a relationship with someone else.

I can’t help but wonder what he was about to say when you told him to get out. He met someone else, which wasn’t a violation of your rules. Did that mean things were over between you two (which would make the timing of the last fuck an insult)? Or was he willing to pass on this other girl if you were ready for a relationship (which would make tossing him out before he could elaborate a mistake)? You probably should’ve heard him out.

Go ahead and reach out. Let him know that you were thinking about taking things to the next level—ughers to that phrase—before he told you about the other girl. You were starting to fall for him, you hoped he felt the same, and you were disappointed. But since he was only doing what you asked—keeping it casual—you can’t fault him for keeping his options open, looking around, dating other girls, etc. And you can’t fault him for failing to read your mind.

Close by telling him that you’d be open to dating—a real, non-casual relationship—if things don’t work out with this other girl.