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Anal advice
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In my experience if you put in enough time in the relationship and build a solid level of trust it can eventually be accomplished,and during that time you need to be building trust and having frank discussions about sex, what she likes, what you like, etc., introduce her to other new sexual concepts like mutual masturbation, food play, etc., to get her to start thinking out of the box.
The best time to initiate that discussion is in the heat of passion on the second or third time you have sex, be direct about it, tell, don't ask, most women respond well to a man who is confident and takes charge in bed.
As far as enjoyment, go slow , never rush and please use lots of lube, give her a drink or two beforehand to relax, spend plenty of time warming her up in front first with your fingers and tongue
The best time to initiate that discussion is in the heat of passion on the second or third time you have sex, be direct about it, tell, don't ask, most women respond well to a man who is confident and takes charge in bed.
As far as enjoyment, go slow , never rush and please use lots of lube, give her a drink or two beforehand to relax, spend plenty of time warming her up in front first with your fingers and tongue