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Well, here's what my boyfriend did the first time, and I think it worked out pretty well. While making out, just rub her in between her legs through her pants. If she seems to be enjoying that, maybe just start playing with the waist of her pants, like sticking your finger down the front of them and find her panties, and just rub the band of them. Assuming that things are still cool with her, just go into her panites and play with her clit a lil bit, then make your way to the hole I guess ^_^
(any questions, like if you don't really know what things are like "down there" you can send me a message through fun mail)
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My girlfriend
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I want to finger my girlfriend but I dont want to ask her I dont know what to do shold I try while makeing out??