My Boyfriend Will Not Take " No!" For an Answer Regarding Anal Sex!?
I am female, 47, divorced twice, 4 kids.  My steady boyfriend of 1 year is 50, divorced 1 1/2 years after 20 years of marriage.  Shortly after we began our sexual relationship, he shared with me that his ex-wife LOVED anal sex.  He tried then to perform sodomy on me.  I told him I was not at all interested.  He has tried a couple times since, and about 2 weeks ago, in a very loving way when we were not involved in sex, I explained to him that the idea of anal sex was very repulsive to me, and that I would never consent or want to pursue that area.  I asked him very nicely not to even think about trying it again.  So, this weekend, he started massaging my anus and sticking his finger in during sex, 69 position.  I stopped him and told him please don't do that, it hurts and I don't like it.  His comment was a pleading, " but it's so tight" .  He tells me he has no problem with traditional sex with me, and that vaginal sex is a snug fit.  I practice Kegel exercise regularly.  I'm afraid that if he tries anal play again, I'll get angry and blow up in a temper tantrum.   I don't know how else to reinforce to him my distaste for this.  Any advice?
Dear Tight Ass,
We know exactly what you should do. Once again, explain to him that taking anything up your bum is not only unpleasurable, but extremely annoying. Then the next time he tries it, simply stop, get dressed and go do whatever you normally do. It's punishment. You won't even have to explain to him why you stopped. He'll know damn well and there is no need to debate it. Keep him cut off for twenty four hours and then approach intimacy with him as you always have.
Realize that we never suggest withholding sex in a relationship as a means of control and we aren't here. This is a matter of him knowingly doing something you find " repulsive" during the act of lovemaking which should result in any person getting up and walking away. It's not a means of control or manipulation, but rather a strict way of defining sexual boundaries. It's the same thing as your lover continually trying to involve the dog in your sex acts. You'd freak and cease action. You need to do the same thing here.