So you think you can cross-dress? A straight guy’s guide to getting into her panties

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.

--Tiger

*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.

When True Blood meets the Sex Pouf

Rhonda Perky goes under the covers to discover a miracle cure for Married Sex

As tends to happen in long term relationships, intimate encounters become less frequent, less spontaneous, less imaginative, and before you know it you're having Married Sex* (when you have sex at all).

Some couples go to great lengths to spice things up, frequenting the nearest Boganburbia Sexyland to purchase 'marital aides,' or just popping into Club X with a tissue or two. Others resort to sharing porn, but this can venture into uncomfortable territory... he wants to watch the one where the lesbians cop facials, she wants the one with the well-endowed pool cleaner.

Let me assure you, things need not end in awkward compromise or virtual abstinence.

Take the example of my good friends, Mr and Mrs McBallsdeep, who recently discovered TV’s vampire craze, True Blood. Free-to-air, not explicitly masturbatory (thus avoiding the eyebrow-raising selection of Asian Angels who love Anal), it provides a whole new realm of improbable scenarios for hours of role-play, for example, jumping out of graves or hanging from the ceiling.

Anyone who has encountered the deadly drudgery of bedroom-only sex (or worse, bed-only marital sex) will tell you that new stimulus is only half the battle. You are now in the right mindset, but as soon as you hit the staid floral duvet gifted to you from your mother-in-law, you realise it will take some sort of prop to stir things up again.

Enter the Sex Pouf.**

Not quite as risqué as dogging (public sex), and perhaps not as thrilling as hanging from the ceiling, I'm assured the pouf is very versatile, providing hours of exploratory fun as you discover new and interesting angles that simply can’t be achieved in your run-of-the-mill boudoir. Plus there's no need to secret away your brown-bag purchases as you hurry to your illegally-parked car in the middle of Boganburbia. A full range of socially-acceptable poufs can be purchased at your local Ikea or Freedom store.

So if one day you wake up and realise the washing machine is only ever used for doing the laundry and the kitchen bench for preparing chops and three veg, it might be time to invest in some serious couch-time with Bill Compton (Steven Moyer), Jason ‘I’ll shag anything’ Stackhouse (Ryan Kwanten), and his little sister Sookie (Anna Paquin).

-RP

*Note: it is not necessary to be married in order to have Married Sex. My ex-husband and I were having Married Sex long before he put that diamond crusted shackle on my finger. Conversely, not all married couples have Married Sex.

**Or ottoman.