However, for the rest of you this is an awkward request. It’s the kind of question that likely makes you want to run away on the spot. Now, if she wants you in something slinky and uncomfortable and won’t take no for an answer, you’re well within your rights to stick to your guns and walk out. This sort of honesty from the woman you’re dating is an open door and you want to think carefully about how you can use that open door before you run away.
A Sign of Trust
The fact that she’s telling you this is actually a very good sign, since it means she trusts you. She’s willing to share something with you that you can bet she doesn’t tell most of the men she brings home. That means she has a certain amount invested in the relationship, and you can put that to good use.
First things first, you have to communicate with her after a conversation starter like that. Assure her you’re not going to run away, if you think you’re not going to do that. Let her know you appreciate her honesty, but if you’re worried you’ll say something daft, ask for time to think it over. She can’t hold a request like that against you, not when she’s already dumped the bombshell on your head.
Let Her Narrow It Down
Asking her what she wants, specifically, can make the conversation a lot more clear. She may tell you that she just likes the idea of you trying on her heels in bed or something similarly low-key. I know it sounds ridiculous, but just think how much she’ll have to put up with in return if you put those shoes on for a few minutes.
If she wants more than that, or if she wants you to go out in public at all, it’s time for some serious negotiation. Ask yourself what she can give you in return. Have you wanted to try anal but she wasn’t letting you in? Maybe there is some fetish of yours that you’ve been keeping secret, so now’s the time to break it out and put it on the table.
When You Have to Say No
Even if you decide there’s no price high enough to make you comfortable in a dress, you’re still in a strong position in the relationship. She’s made herself vulnerable to you by outing her cross-dressing fetish. She’s likely to put up with more from you because the idea of starting over with another guy is too exhausting. You can string her along with the promise that you might be up for it some day for a long time, and in the meantime, you know she’s the kind of kinky girl who will let you indulge in your own kinks.