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Knee high tube socks with a short skirt and heels? That's sexciting! Being hogtied, lightly, while wearing these clothes and being tickled and humiliated is great, too. I've done something similar a few times. You didn't mention what the woman would be wearing on top. I'd opt for a demi-bra providing support to the bottom of my breasts but leaving the top half, including my nipples, exposed. But forget about having a sock or anything else ducktaped in my mouth--that's dangerous and I don't think you should ever take that fantasy into the real world.
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