not to take away from Ashley's thread... i'm also putting this in here to attract some mature responses. but my girl can't fit me, anal or vaginal. not that we've really tried anal... we've been going out (read: sexually active) for about 2 years, and have sex regularly, but its never stopped hurting her. its not AS bad as it was at first, but its very very rare that we have sex and she doesn't feel pain. for example, if we were to have sex 15 times in a month, 14 of those times it would hurt her. obviously this makes me feel like an asshole, but theres nothing i've tried that helps on the odd occasion that it doesn't hurt her, its great and she enjoys it thoroughly, but it seems to be completely random. not the same time of month, not the same position, not the same amount of foreplay... totally at random. everything else is fine, she loves oral sex (at least GETTING oral sex ) toys work, we use one of those "rabbit" devices, a vibrator with a stimulator attached and it makes her squirt every time but the dildo portion of it hurts her. it's a little smaller than me, length and girth-wise. has this happened to anyone else? i know its not me, it's never been an issue with anyone else i've slept with. anything people can suggest?