Playing with dildos, as with other more manual ways of pleasuring the anus, can lead to a lot of insecurity. Sure, one is similarly passive while being given a blow-job, but that’s manageable, because – well, getting a blow-job is universally, laddishly applauded as fine and dandy. Conversely, the anus is the stuff of long-winded Freudian analysis: babies play with their ca-ca; real men don’t. It’s taboo. (Though it feels so good!) Fine if he’s sufficiently lost in genital sensation that you figure the pleasure and general gung-ho abandon is different but mutual. Not so fine if he’s watching you.
Which he probably is. Let us at least hope he is. If he’s a sensitive lover he’ll be looking at how you respond while he works with the dildo inside you. He’ll see every tiny wince, each grimace, each moment of wordless joy, each sigh. And, assuming he isn’t on some sort of power trip (in which case, show him the door), he’ll be concerned for and vicariously sharing your pleasure.
You need to trust him, to know you can show him where you go when he’s making love to you, even though he’s (relatively) in control. You are letting him see something so very intimate. You need to know that he’s happy to see this, and more that he loves you for letting him see it, letting him get so close, that he respects you for showing yourself being so vulnerable. Talk to him. Tell him your hopes and fears. Make sure that it is what you both want.
If you’re using the dildo on him, be careful. Be the most careful with him that you’ve ever been. It’s a nice thing to do. You have more control: it’s his pleasure you’re focused on; you’re not distracted by yours.
Accept every response he makes. Don’t try to make him feel something he doesn’t. Don’t, for heaven’s sake, make him act for you. Keep it real. Your role is to be completely supportive – and, beyond this, to learn from what you are seeing about how his desire and sexuality work. If you can remember him as he is now while you’re having anal sex you’ll be a better lover.
When we agree to use toys we risk splitting sex from love and personal desire. They can seem so impersonal. Used well, with great sensitivity and honesty, they can enhance our sex life.