Will she love it, will she freak, or will she just hate that you have better legs?
As a straight guy, the idea of cross-dressing has always interested me. There’s something very tempting about the thought of sliding into some soft silky girly undies. In fact the thought of that flimsy material straining against my package and fishnets hugging my calves and thighs makes me positively shudder with delight and go weak at the knees…
(Ok, ok, putting my brain back online).
We now all know that I like it, maybe you like it too, but will she like it?
Perhaps if she’s a little dominant, the thought of you emasculated like that will be a turn on (maybe that’s why you like it). Maybe she’s vanilla and will freak out, running away, sobbing and screaming. Or maybe, just maybe, she’ll be jealous because you look much sexier in a garter belt than she does.
Putting all of those ifs aside, let’s assume you’re prepared to take the risk and give it a try, hoping against hope that she isn’t as vanilla as she seems (after all you can have vanilla all your life; why not sample some of the other flavours before you die?)
First you need to work out what to wear (decisions, decisions… I’m sure that cellulite wasn’t there this morning…) Do you secretly borrow some of her stuff and surprise her? (If so, avoid the expensive designer ones as you will most likely stretch them beyond repair.) Do you go to a lingerie shop in your local shopping centre and enjoy the speculative glances from the sales assistant when you ask for something for your girlfriend who’s about your size, and oh incidentally does this colour go with my eyes…? Or do you head to a sex shop, where (assuming you choose the right one) you will get lots of help, be able to try most things on, and find a range of absolutely delish corsets – uh, I mean, find some really great stuff.
Actually, let’s take a step back. Before you get to what to wear (the fun part) you might like to sound your partner out. The last thing you want is for the poor girl to walk in on you unexpectedly wearing her undies and makeup.* If it was me, I would talk to her on a quiet evening at home, perhaps after a glass or two of red to relax (her, not you – you need all your wits about you), share your fantasies, and find out what turns her on. I’d gently open with how hot you think her undies are and how you’ve always been curious about what they would look/feel like on. If she’s not vanilla she may suggest you try some on as a joke. This is the crucial point. If you agree and she doesn’t freak, you know it’s ok to start suggesting where to get stuff; if she does freak, you can always pass it off as a joke (preserving your poor bruised ego).
Say you do end up trying things on. Be honest and tell her how it makes you feel (sexy is a good adjective here). If she’s understanding, the fact that you so obviously enjoy it should make her much more open to the idea.
And it that goes well, you could even go shopping together.** And if it doesn’t… well, you live and you learn.
Above all, have fun exploring.
*Under no circumstances should you start giving her tips. Even the most reasonable and understanding girlfriend may lose her shit at that point.
**Make sure you both get something sexy; it’s no fun if she doesn’t get spoilt a little as well, and who knows, you might get matching colours.