The next step is once again a subtle progression in the direction you’re trying to go. When you’re out with your wife and she’s buying cosmetics take an interest. Ask why she likes one brand of make up over another. Be sure to have a sincere interest.
Ask if there’s a better one, probably more expensive. Offer to buy the more expensive one, ‘just so you can try it out’. You’re softening her up all the time. She’s possibly going to notice this change. If you are usually an inconsiderate pig, chances are she’ll notice a lot sooner than otherwise. You’re objective here is to be subtle.
Yes, I know, this might go against the grain. However you are setting up a very delicate thing. Many men literally go to their graves without even broaching the subject of crossdressing. If you’re going to do this, you need to do it right.
If you’re smart you’ll go out and learn a little more about makeup and cosmetics. It’s not hard to find write ups in women’s magazines. You’ll find there’s a while language around make up, talking about the creamy feel and vibrance of some brands. You might find yourself wanting to eat them, rather than wear them. Try to resist the urge, especially if you’re buying expensive brands. Good makeup pretty quickly gets expensive.
Keep in mind, if you buy her the more expensive creams you are changing the dynamic subtly. This is no longer ‘her’ face cream. It’s now something you have something of a claim on. It’s ‘our’ face cream now. This is a very small detail but a powerful one.
You may not act on that for a while, but at some stage she’s going to need some more. Now it’s ok for you to be the one who buys it. After all, she showed you the one, right?
What could be more natural?
If it’s her birthday, or Christmas, be sure you buy her the best cosmetics you can. Complement her eye makeup and ask ‘how do you do that? Your eyes always look so good.’ Encourage her to talk about it. ‘Where di you learn that?’
Most young girls spend hours playing with makeup. Get her to talk about how she learned. These are likely to be happy memories. Everyone loves to talk about happy times in the past, so it’s easy to encourage her. All the time you’re creating a comfortable space for her to talk and participate in. Keep in mind, she’s already going in the direction you want at this point.
From here it’s the easiest thing to say, ‘Can you show me?’ Whether she demonstrates on herself, or on you, just look surprised and go along with it.
Now, a word about language. What follows may sound a small thing, but it’s quite important. If you manage to get this right, it’s going to be plain sailing from here forward.
At some point she’s going to help you with cream, or eyebrows, or eye makeup. Let her, and as she does so say under your breath, as an afterthought, “I love it when you do this to me.”
That’s a very specific phrase. It’s not the same as “I love when you do this for me.” When you phrase it as something she is doing ‘to’ you, you’re giving her the control. This is both empowering and intimate. Now, you and I both know that you are allowing her to do this, but that’s not the point. Subconsciously she’s getting the message that she’s doing this ‘to’ you. She’s in control. She has the power.
You’ll find she probably like this, even if she doesn’t say anything. It will give her a little thrill. We’ll come back to this later.
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