When is the right time to start wearing lingerie for a new beau?

When you marry him.

The night you do some special celebration of some kind of anniversary, like when you go away for a special weekend.

“Umm…when is the timing right…”

Umm… when he’s finished wearing them?

After you’re married would be better. Other than that, I’d say it comes down to preference.

I’m afraid if I do this all too soon there’s nothing left for fun. Dude, there’s like an entire world of possible lingerie options. Do you ever look at a dress/pair of pants/skirt/kickass combat boots/sweater/adorable headband/tie belt/jacket and think “I dunno, if I wear this too soon, there’ll be nothing left to wear eventually”? No. Because there is no such thing. Variety is the spice of life, and I promise you, there is way too much variety out there for you to use up in one lifetime.

Do it for a special dinner at home or something.

Believe me, if you’re just starting out again, everything and anything you wear is sexy. Bring out the heavy guns only on special occasions. That keeps them special.

In my experience (and this is granting that I am only 26 and my relationships are nowhere near that level of life for either partner)... girls I’m with are usually wearing some kind of flashy underwear even the first time we get intimate… not straight up lingerie, but you know, the like “black-bra, cute panties” thing.

Lingerie usually comes after a few months, if at all. To be honest I’ve often found cute regular underwear to be far more attractive than “sexy” lingerie (though that’s not a constant).

I also wouldn’t worry about necessarily leaving no room for fun. I can’t really speak for guys of your beau’s age, but sex doesn’t really get boring, and there are always different outfits and different fun things you can try.

It has to be something special. You’ll know.

I’m a guy and I’ll be honest with you here. Unless it is dirty or totally missing, I do not notice the wrapping paper on a present. I only care about what is inside the box.

Clean, standard, 100% cotton, bikini, high leg underwear is the sexist lingerie imaginable when I’m with a passionate, willing partner. I do not need silk, or lace, or rubber, or…
I just need you to be loving, comfortable, and relaxed. You are already the best present.

@worriedguy What is your spouse on this site or something? lol

@tedd Lol.

Not every woman likes to wear lingerie. Neither my wife nor any girlfriend I had before her liked to wear it. I never had a problem finding my wife sexy.

If you want to wear lingerie, do it when you feel like it. Vamp it up. Show it off. Lingerie is not how you keep your bf’s interest. It’s what you do with it. It’s how you project yourself that matters. You could have all the lingerie in the world and still be as sexy as a tax return. You could have none, and be so awesome your guy can’t take his hands off you.

You are what sells the lingerie. Not the other way around.

@tedd No, she’s not. It’s the truth. She doesn’t come here at all. I was thinking of other lovers over the years and what they wore. Seriously, 95%? 98%? of the joy and pleasure of the experience has nothing to do with the clothing. Maybe I am fortunate that I do not have trouble getting excited and don’t need that extra stimulation. It’s the woman that counts.

@wundayatta That’s exactly how I look at it, only you said it better. Thanks.

Wait! What’s that sound outside my door? It sounds like the “klip – klop” of horses hooves. I see a couple of women in high heels outside…. Oh no! It’s the Victoria’s Secret Agents at the door! They’ve just declared PINK Jihad on me. If you don’t hear from me it means I have been silenced. Don’t worry I’ll be sure to record the whole thing. That video will be worth a fortune on some porn site.

If you enjoy wearing it then make it part of your regular clothes, little by little so there’s always something you feel is special, some days less and some days more. Sooner or later he’ll give you some feedback as to what he thinks is to the point of special.

Sometimes, lingerie isn’t because you’re trying to turn your partner on more, but because you’re trying to help get yourself in the mood and it helps be a bit of a boost so that you can focus on the mood and moment, and not on how you hope they aren’t looking too closely at that “imperfection”, or how you feel more bloated than sexy, or how you really should pay more attention to that giant pile of laundry, or omg so much work that needs to get done… Most of the time, when I’m wearing lingerie, it’s because it helps put me in the mood, not help get them in the mood (also true for costumes/role playing).

When you two go somewhere for the weekend.

@worriedguy haha, don’t worry, I’m just giving you a hard time :)