I want to have anal sex with my boyfriend. I read that you can wear a butt plug beforehand to prepare. True?
Good grief. What do you think people did before the advent of the novelty marital-aide industry? Sit on pinecones? You don't need weeks of prep to achieve what may be in some senses an "unnatural act" (the rectum being far better at pushing things out than it is at taking things in) but is nevertheless performed regularly and pleasurably by normal people everywhere. I'd certainly suggest you try a smoothly manicured finger first to see if you even like this sort of thing. Use a bottle of lube. It may take time, but by time I mean minutes or hours, not weeks.
My boyfriend and I are planning to start having sex. I feel kind of silly saying this, but I am really scared! I'm afraid he won't fit! Should I try stretching first with something? Or is that just ridiculous?
First off, please stop using words like "silly" and "ridiculous" to describe yourself and/or your perfectly reasonable concerns. And second, yes, it would be pretty ridiculous to resort to something like vaginal sounds or graduated dildos to do what your very own vagina so cleverly evolved to do for itself. That said, it is far more likely to be successful when you are hot and bothered and ready to go. It will not, however, take weeks of preparatory homework and a specially-fitted case full of precision instruments.
I am just starting to date a new woman. I find her very attractive but frankly, she is BIG. Do I have to figure out some new positions or angles?
You might, but I'm guessing she may know something about this herself. You may want to consult her when and if it comes to that. I enjoyed this summation of how not a problem your problem is likely to be, from the "Fat Sex" page of Dimensions Magazine's website: "Those authorities who have taken the trouble to investigate the matter report that obesity is rarely, if ever, a barrier to intercourse." ... Or, as Marvin Grosswirth put it in "Fat Pride": "To put it bluntly and squarely, no woman is so fat that her vagina is inaccessible."
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