My boyfriend has a habit of trying to stick his finger in the "out hole." This does absolutely nothing for me. I have told him this, and added that I am willing to do whatever else he would like. How do I divert his attention from my ass-end?
A guy who keeps trying to finger-fuck your asshole when you've told him you don't like it is a jerk. But I am curious to know why you don't like it. The asshole has a lot of sensitive nerve endings. It's an orifice that a lot of people enjoy having filled or penetrated. So what is your issue? Would you enjoy his stroking your anus if he used a little lubricant on his finger? Would you like anal stimulation if it was external only? Would a finger be okay, but not his cock? Do you think it's dirty? If so, would you like anal play better if you could take a small enema beforehand to clean out the lower portion of your colon? Are you afraid it will hurt, and you don't trust him to take the time to relax you? Does it trigger memories of sex abuse?
I don't mean to imply that anybody who is hip and with it has anal sex. That's not true. Some people just don't enjoy the intersection of sex with the rectal passageway. Their physical or emotional feelings about anal sex are so strong and so negative that it's never going to be a good idea to try it. You definitely have a right to turn him down. He doesn't get to exploit or use your body for his own pleasure if it's not getting you off too.
I would suggest that you insist on talking about this in more detail. Instead of just saying, "No," get him to tell you why he wants to have anal sex. If he's had good experiences with it in the past and knows how to make it feel good, that might be nice for you to hear. If not, he needs to be told what your concerns are, and how far-reaching they are. If he hears in detail just exactly why you do not like the idea of anal sex and feel that you will never agree to do it, no matter how much he might have liked it in the past with other women, say so. If he persists after that, I think you have grounds for a breakup. No means no, and he has no excuse for not respecting a boundary that you've set with such clarity.
When you say you'll do "whatever else he would like," you are making a pretty big promise. From the letters I've received in the course of writing this column, I think it's safe to say there are probably a lot of things other than a finger in the rear that you wouldn't like. You'll do a better job of distracting him if you come up with a few suggestions that are explicit, so he knows what else is on offer. A blowjob with an ice cube in your mouth? A blindfold? A massage with a spicy-smelling oil? Sitting on his dick? You know his preferences better than I do, so I'm sure you can some up with something that will derail his dirty mind.