ANSWERS: 2
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Make sure to use one of the softer and more flexible dildos rather than a very stiff one. LOTS of water-based lube. Make sure she knows that she needs for the insertion to go very slowly and gently, and the absolute requirement that your word is law: if you say stop, s/he stops. It may be a good idea to use sex toys with a smaller diameter at first, to see what you're comfortable with. Plenty of men and women find anal sex enjoyable, though!
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whoa well I would assume you have never had your butt cherry popped huh?? judging by your question Heres the thing its a natural exit yes its going to hurt unless you relax and have her massage it use plenty of lube and make sure you take a big shit and shower before you do this. otherwise poop will get everywhere. But it can be fun..might I suggest her giving you a blowjob and sticking a finger in your ass to start off the festivities
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