Hint about underwear switcheroo first

Miss Lonelyhearts By: Miss Lonelyhearts Posted:

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Dear Miss Lonelyhearts: My wife and I have been married for a while, and I recently realized I want to try wearing women's underwear. Just putting them on for her and showing her before making love, not full cross-dressing or wearing them out in public. However, I don't think it would go over well if I suggested it, and I couldn't just surprise her by wearing some to the bedroom (she would likely be mortified).

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Opinion

Hey there, time traveller!
This article was published 19/04/2016 (3802 days ago), so information in it may no longer be current.

Dear Miss Lonelyhearts: My wife and I have been married for a while, and I recently realized I want to try wearing women’s underwear. Just putting them on for her and showing her before making love, not full cross-dressing or wearing them out in public. However, I don’t think it would go over well if I suggested it, and I couldn’t just surprise her by wearing some to the bedroom (she would likely be mortified).

It would be better if somehow she would suggest it, but that would almost certainly never happen. Do you have any ideas about what I can possibly do to help warm her up to the idea?

— Interested in Undies, Downtown

 

Dear Interested in Undies: This is your interest, and I’m guessing you’ve experimented alone and maybe for while. You might frame this as a story about someone you know who did this and told you about it, and he said his wife doesn’t know what to think. You could discuss it a bit with her, and get around to asking what she would think if you did that? She will probably be getting suspicious by then, so let the discussion go and let her mind will work on it.

If she says in a further discussion she probably wouldn’t mind, the worst thing you could do would be to get too excited and say, “Well, that someone is me — let’s try it right now!” Just say casually that you have also been thinking about it, too.

This needs to sift slowly through her brain, not be shoved at her, even if she says she thinks she wouldn’t mind. And it’s not a one-way road. In preparation, you need to ask her what some of her wildest fantasies are, and be willing to help her fulfill those. A kind of trade. If she’s just doing this thing for you, and nothing for her, it might be a turn off. She’s losing some of the fun of your male-female dynamic. But, if she’s really experimental, you might want to have a night of experimentation both ways, with dinner and a little bubbly to loosen your inhibitions.

 

Please send your questions and comments to lovecoach@hotmail.com or Miss Lonelyhearts c/o the Winnipeg Free Press, 1355 Mountain Ave., Winnipeg, MB, R2X 3B6

 

 

Miss Lonelyhearts

Miss Lonelyhearts
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Miss Lonelyhearts

Miss Lonelyhearts
Advice Columnist

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Our newsroom depends on a growing audience of readers to power our journalism. If you are not a paid reader, please consider becoming a subscriber.

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