1. How does one find the clitoris?
I’m told the clitoris is not hard to find — go north, young man — but if one tries to find it and one fails, one should pull over (or pull out) and ask for directions.
2. If someone tells you to “do whatever you want,” should you?
Someone who says that and means it is eventually going to say it to the wrong person and get hurt; they’re a danger to themselves. Someone who hears that and takes it as license to do whatever they want is a danger to others. So, a decent person — by definition — wouldn’t do whatever they wanted to someone who told them to do whatever they wanted. And seeing as you’re a reader of mine, I’m hoping you’re a decent person.
P.S. People who say “do whatever you want” don’t mean it. What they mean is this: “I’m too embarrassed to ask for what I want, so I want you to guess.” Never guess.
3. I've been with my partner for eight months now. I'm a quite small woman and seem to be even smaller down there, which means there's much I can do in the bedroom without getting hurting. We have tried different positions but more than half cause me to bleed or be so that we’re left with maybe three positions that work. I can see he gets frustrated with being limited. Is there any way to make myself slightly bigger to give him more room to have fun?
Most straight couples experiment with different positions before landing on a few that work for them — positions and angles of penetration that work best for their bodies during PIV — and those positions become their go-to/default positions. There are lots of ways two people can enjoy each other prior to having PIV in a position that is pleasurable for both partners; two people can also enjoy each other (and get each other off) without having penetrative sex.
If your boyfriend is pushing you to have PIV sex in positions that are painful for you, he’s a selfish asshole and you should DTMFA.
4. Should a woman “prep” every time before doing anything anal — even just a plug?
A woman who can’t tolerate even a chance of mess should “prep” (read: douche) before anal; if someone is into anal but squeamish about mess, he should ask his female partner to prep and show his gratitude for the effort with something other than his dick. As for butt plugs: since they don’t go in and out during sex, they don’t require prep. If you’re concerned about what a plug might look like when it comes out, head to the bathroom once the fun is over and remove it on your own.
5. How do I keep my boyfriend satisfied when he is more experienced than me? I have only had sex with him. He said the sex was so bad at sex at first that he almost ended things with me because I’m so inexperienced. It's hard to act sexy because I don't feel sexy. What do I do?
I think you should take your boyfriend at his word — you’d be better in bed if you were more experienced — and go fuck some nicer guys, some hotter guys, some guys who wanna build you up (and get you off) instead of tearing you down.
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