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Wow, interesting question. What about working your way up to it? Try playing a game where you and your gf have to completely exchange clothes in two minutes. I guess it also depends on what it is you like. Show up for a date wearing a woman's clothes (something daring like a blouse and bra) if you just like to wear woman's clothing. If you like the idea of being undressed and then having a girl dress you in woman's clothes, try losing at strip Poker and once you are naked have the dares be each time you lose again you have to put on your gf's clothes. There is the straight forward way of just asking your gf to take off your clothes and put her clothes on you.
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∙ 14y ago
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