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Never done actual penetration with her....
But she very much enjoys me playing with her clitoris during that time of the month. We usually wait until she's a couple of days in and she always wears a tampon, but she has come a long way in her comfort level.
The key is to just go slow and start small, show her that you are comfortable with it and that she has no reason to be embarassed.
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"The South is gonna boogie again"
- Disco Stu
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