My vagina is very elastic, I think lengthwise as well as widthwise. Stretching it has never hurt, during sex or any other time. I think this is because it has been fairly well introduced to stretchery. I did not put things in it when I first started masturbating, but worked up to a couple fingers and whatnot. Also I've always used internal menstrual products.
The degree to which it can stretch is explained under size.
Stretching my vagina does not wear it out, or make it less elastic for later. It always bounces closed again. It is made of muscles, and meant to be stretchy (for babies to fit through). A fair number of people seem concerned about the possibility of vaginas being stretched out of shape and becoming loose or saggy. To my knowledge, this does not happen, although the extreme stretching while giving birth can resize the vagina a bit. Exercising the vaginal muscles can help keep the vagina toned and strong.
Being stretched does not make my vagina sore, but it can contribute to extra rubbing (big things rub more than small things), which can end up hurting some. Thus, it helps to be extra slippery if something particularly large is going to be in my vagina. A penis is not particularly large; something like a hand or a lot of fingers is.
I can feel my vagina being stretched much more than anything else that is done to it. It is generally a good feeling.
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