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Why is it that his anus is safe from penetration while yours isn't? You both are into "adult" web sites that extoil the amazing virtues of anal sex/play, so why isn't he so eager to jump on the band wagon of getting deflowered anally by a strap on? What's fair game for your anus should certainly be considered fair game for his own beloved anus!!!
Ask yourself this question, "why does he get the benefit of respect of his boundaries and limits but you don't?" Do you feel somehow that you arn't entitled to have boundaries and that they be respected? If I were you, I'd give him a taste of his own medicine. Get a dildo of equal proportions to his penis and tell him that you've got this really burning desire to take his anal virginity. Weild this dildo around like a sword and every time you go down on him or play with his package, place the dildo against his anus in a threatening manner. I'd pressure, coerce, threaten, and bully him until he either consents to the violation or until he begs off for what ever reason. Then ask him why should his boundaries be respected while he isn't respecting yours!!!
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