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By Christina Oehler Updated: If you've tried several tactics but nothing seems to work, it can't hurt to check in with your ob-gyn, she advises. Positions that keep your legs wide can also help, since that can elongate the vagina. It's also possible that just as some penises are on the small side, some vaginas might be, too. Try to get a dilator similar to the size of the man. But once you hit menopause, your body's estrogen output takes a dive. Store-bought lube is also a good idea.