Caution...

Like all things which can be sexual, cross-dressing is great fun alone, but much more fun with a willing partner. This article is not aimed at the loner.

Take it slow

Sooo pretty....

Like anal sex, its probably not a good idea to rush this one. If you're a girl, you have a moderate chance of a favourable reaction from your partner if you suddenly appear in a masculine suit and tie. Our psycho-social conditioning is unfortunately stacked against the man who fancies the feel of frillies. From either sex's point of view, though, any change in direction to what it was they thought they saw in you, which is why they are with you after all, may come as an unwelcome surprise. The most gentle way to begin is with an indirect question; aimed at neither of you, just introducing the arena. Examples;

• Is it cold wearing a skirt?
• How often during the day do you have to refresh your lipstick?
• How did you learn to balance on those heels?

Just let the conversation drift on for a while, don't rush in to what you want to say. Let your partner suggest that you experience the issue for yourself and don't be too eager...
If you already know your partner is the adventurous sort, then you may be able to suggest a single token play item or simply pick up something to hand and note carefully how your partner reacts. This will be no fun for anyone if it turns them off!

Moving on

If you've made it this far, then your partner has got to this point in their life without being imprinted too strongly with society's stereotypes. Congratulations.

Now don't blow it.

Talk to him/her and tell them how it was. Tell them you came enjoyably - don't tell them it was better than anytime before! That just says to your partner "you're not as good as X" and no-one wants to hear that implied or not...
If it worked once, try it again, possibly in the opposite direction; "I wore your x so try on my y". Normality is what you're trying to adjust and that might take quite a while.

Cognizance

Once you've made it here it's probably time to come clean about your desires and from this point its make-or-break.
If your partner wants to play this game then I wish you all best, you've established a rapport that you can build on.
If your partner does not want to play then you can agree to dress in private, stop dressing up or split up. It's that simple - get over it.

Anyone who expected a treatise on choosing the best dress style and wig colour can sue me. This written from personal experience. Your mileage may vary.