How to talk to your partner about crossdressing. Part 5

Part 1 can be found HERE.

Remembering that this is all about timing, we’re going to move a conversation into the area of fantasies. This should not seem forced, so pick you time carefully. Don’t just say “The weather’s nice for the time of year, and by the way, what do you fantasise about?”

Wait for your moment. Approach the subject with sensitivity, and be gentle. Tell her you would love to know what she fantasises about, because you want to make her happier and to serve her sexually as well as you can.

In surveys about what women fantasize about, as many as 30% of women fantasize about being the man during sex. The number is much higher when the question was ‘have you ever fantasized about being with a woman sexually’.

The number of women who fantasize about a dominant role, forcing a man to do things to either pleasure her, or humiliate him are higher still.

When you start talking about fantasies it’s not to a great stretch to steer the conversation toward, “have you ever fantasized about being a man?” You’ll be surprised how many women have. They may not admit it, but the fact remains, this is an intriguing possibility for many women.

So, as you talk about fantasies, draw out your partner and eventually you’re going to use the phrase, “I think it’s probably easier for me to pass as a woman than for you to pass as a man.”

Just let that hang out there for a moment. See what she says, but here’s where you really pull the trigger…

“I bet you can’t pass as a man for 30 minutes.” We’re looking for a scenario such as a restaurant, or shopping, or in a café, or even at the cinema. So, you lay down the challenge.

Here’s where the fun starts. In about eight out of ten cases she’s going to say, “If I do that, you have to dress as a woman and try to pass for the same amount of time.”

“You haven’t got a chance… But if you win, I’ll give it a try.”

Now this, or some close variation of it, starts to be fun. It could be that you suggest the bet is that she get dressed up and you do a photo of her as a man, and if she does it – well, you have to as well. Anyway, you see the general idea. One way or another, she’s likely to be asking you to dress up.

The great thing about this method is that it can be so exciting, that you end the bet in bed. As long as you tell her how wonderful and exciting it all was, the chances are you’re going to be doing this regularly.

So, that is how you get her to ask you to crossdress. I always love to hear how you get on with these little exercises, so be sure to leave some comments in the section below. And don’t forget, we’ve always got new material coming out for you on Http://

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2 Replies to “How to talk to your partner about crossdressing. Part 5”

  1. Totally love, love the technique & patience aspect. Letting her “show” you or
    “Do it to” you, not only shows your interest, but you learned something quickly, that probably takes women years to master. Plucking eyebrows……I mean c’mon!!!!! Sounds easy, until the tweaser are in hand stand in front of a mirror. Buying cosmetics……..then saying it’s “ours”, idk about. From my experience, ladies are super picky & detailed when it comes to “their” makeup.
    Thank you…..for the 4 part advice or technique post, Very informative & helpful mindsets from the women point if view. Keep up the amazing stuff, I look forward to each & every update day!!!!!
    Jessica Nicole

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