This month, Details magazine has a provocative article about "demanding" anal sex. Read it here.
Dear Go-To Girl,
I really want to try fingering my boyfriend's ass when I'm going down on him, but he won't let me. He obviously doesn't know how good it feels or he would let me; how can I convince him? I think he thinks only gay guys like having their asses touched, but I know that's not true.
Want to Let My Fingers Do the Walking
Tons of straight guys get skeezed out by the idea of having you stick a finger in their ass, but I don't know if it's as much a fear of getting in touch with their inner gayness as much as it's a fear of something they think might be painful. Or painfully gay.
Chances are, at some point in his life, a guy has put his own finger in his ass, even if it was when he was a kid. If it felt good then, he'd still be doing it. So it's your job to connect the dots for him.
I don't know how many guys refuse to allow their girlfriend to put something in their ass; unfortunately, we don't collect statistics on that sort of thing. But most guys I know, if pressed, will admit to having tried it. It might be something that changes with age; the more experienced you get with regular, vanilla sex the more curious you become about trying new things. So if your boyfriend is, like, 22, you might trade up to an older model if you want to get kinky.
If I were you, I'd have a bottle of lube handy, maybe under the pillow or in your pocket, when you're going down on him. Get him to spread his legs and, um, surprise him with a well-lubed finger. Hopefully he'll like it so much that he'll let you stay in.
The capacity to experience pleasure with anal play is the same for guys as girls; you have to create an association in the brain that it can be pleasurable to have your ass played with. That's what makes the blowjob crucial.
If he really won't let you, I'd say let it go. Surely there are people who just can't have a good time with something in their ass. It's up to you to decide whether or not you want to be with someone who won't let you in. Having someone put their finger in your ass doesn't make you gay more than going to "gay reparative therapy" makes you straight.