Dear Go-To Girl,
I am having trouble finding real advice as to how to stretch my vagina to make sex more comfortable. I have had a good deal of sex in my life, with all sizes and shapes of boys. However, the current sampling is rather well endowed, to the point that he has terrible difficulty entering me and if I come, it causes him great pain. Oddly enough, it just feels rather delightful for me, the fullness is quite delicious. I actually do think, upon further analysis and much masturbation, my vagina is smaller than it used to be. Could I have pulled something? Could it be as a result of 5 months of celibacy? The doctor said there was nothing physically wrong. I have been using toys like crazy, and it seems to make no difference. I have ordered a set of dilators- but I could use some more advice on this issue, if its out there.
This is the "This might sound douchey, but I really do find Magnums more comfortable" of girl questions. So your boyfriend is too big, you're too tight, and that causes him "pain"?
I don't think the problem is in your vagina--I think the problem is in your boyfriend's brain.
As far as I know, tight vaginas prized pretty much everywhere, and not just because they're usually attached to girls that are "young" or "barely legal." Or come in dozens. (Please join me in googling "tight pussy")
Tightness is prized because it feels good.
Vaginas are "too tight" when the woman who owns the vagina finds penetration with something--fingers, tampons, dilators, penises--painful in a way that doesn't go away after a few minutes of, um, practice. Unless you have vagina dentata, your vagina's contractions when you come shouldn't be causing pain to any nearby penises. Quite the contrary.
So, yeah, you can try dilators but they're designed for women who experience pain, not men. You might try putting a few fingers inside your vagina when you're coming so you can feel what your boyfriend claims to feel and see what it's like.
But really, no, your vagina isn't too tight. Your boyfriend is basically complaining that his new Porsche that he won on The Price is Right doesn't have enough legroom. Give me a fucking break.