It's great that you and your boyfriend can trust each other enough to be frank about your innermost desires. All too often, couples' sex lives stagnate because they're too embarrassed to voice what they really want to try in bed, or because they're unwilling to explore activities that are considered to be a little “off the beaten track.” It takes open communication, a non-judgmental attitude and, at times, a good sense of humor to be able to successfully pull off such a relationship.
It's apparent that your man really appreciates your encouragement, though it sounds like he has a hard time believing that anyone could be as open and understanding about his liberated sexual past as you. It seems like he's not used to receiving such positive support about such an intimate part of his sexual history, probably for fear of being judged or rejected, but it's clear he is taking baby steps to let go of any uncertainty he might be experiencing.
With that said, it's important that the two of you continue to have fun discovering what sex has to offer, but keep in mind that your boyfriend will only go as fast as he's comfortable with. You're doing a good job reining in your enthusiasm, but it's clear that the fascination you have about Anal Play is making it hard for you to think about anything else. It sounds like you aren't pressing him too hard – yet - but be careful that your curiosity for bum play doesn't turn into a fixation that will send him into a shell.
Based on your boyfriend's reaction to how cool you are about his past, he still might be coming to terms with his own sexuality and his preferred Sexual Orientation. That doesn't mean he won't be open to stuff like fetish, bondage, or Role-play - but he may feel more confident being in the driver's seat rather than being unprepared for what's to come. Alternatively, he may simply enjoy being in control as part of his role in the Master-Pet scenario, so he could easily be stringing you along to elevate your sexual appetite.
As to your second question, the same thing goes; don't fixate so much on just one aspect of sex. You've made it very clear that you'd enjoy playing with his anus, but it is truly up to him to come around when he's ready. The only way you'll continue to enjoy such an open, exploratory sex life is by respecting each other’s' boundaries and keeping the playing field, so to speak, positive and not pressured.
Posted: 17 Aug 05:20