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Well... the same risk from just one when it comes to diseases.. but you could stretch yourself to the point of a tear I am sure.
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Have you tried fisting?, it would be the same, so if you want to stretch your vigina that much, may be you should ask someone to fist you first, that way you would have more controle over the penetration, and may be let another woman do it first, she will be gentler, and her hand will probably be smaller, and if that goes alright, then you can try double penetration.
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There is no risk it done right. I just had double vaginal and double anal sex for the first time this past weekend, and it was marvelous. However, I had to use TONS of maxi glide, have a LOT of foreplay and breast stimulation to get me wet and relaxed, and both my guys were very patient. Let me back up---I do have to admit that I did feel a slight pinch and or tightness sensation in my vaginal/anal area, because I'd never had two penises inside my vagina or butt at once, and these were pretty big sized penises. It felt great, and although I KNOW I can't do it every night THIS early on, but I'm most definitely going to pace myself and keep it up, so I can continue stretching, and my guys WANT to stretch me too (lol)...
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