Not on the sly
But my wife does trust me and I have packed for her. I've done it on both planned and surprise (where she comes home, I have a bag packed and don't even allow her to grab a glass of water before we're back out the door to somewhere she knows nothing about) trips.
Now I do understand her comfort level and am careful not to go too far (otherwise it may be the last time she trusts me to pack her stuff). I will leave out bras (but of course, I can't address the one she may be wearing as we leave) or pack shelf bras as being a 34A, she feels without a bra, no one will thing she has boobs. She wears thongs 100% of the time anyway so the only logical step would be no panties. A pleasant look with a dress. On a trip several months ago to Vegas, I packed a garterbelt and stockings. She had a snug lycra dress with the belt and stocking. No bra or panties.
The one dress/blouse I'm having issues with are the type that has no buttons, but is open to the waist (or close to it). She's tried them on in stores and they look great (she's 5'2" & 108lbs), but I will get the "I can't wear this without a bra? (HUH ?) or "My boobs are too small for this." I'm keep flirting with the idea of going back to the store and buying one when she tries it on and makes excuses not to buy it, then packing it for a trip.
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