I want to play with his anus!
My boyfriend and I have been dating for over a year and are very happy together. We have a very active sex life with each other and are both very open to exploring. We've role played, done some bondage, played with sex toys, had anal sex, and many other things.
In one of his prior relationships he was with a transsexual person (male to female, non-operation) and she gave him anal. He enjoys playing with toys by himself anally. He was very embarrassed about this when we first started dating although I told him I was alright with it, that I thought it was hot, and that I felt lucky to have a man who is sexually open to trying things.
He's been slowly warming up to being open about his past relationship. He even recently sent me a picture of him with a dildo up his ass (I asked him to send me one a few days earlier). I want to try to take it to the next level by playing with his ass, but I don't want to pressure him either. I recently asked him if i could watch him while he plays with his ass sometime and all he said was, "Maybe".
My question is how can I bring these things up to him without ‘weirding him out’ or making him feel pressured? He is really shy and yet really open, but he is more open to doing things to me than me doing things to him. I don't want to make him feel really uncomfortable whenever I bring this up. Advice?
Also we recently started getting into more of a role-playing relationship where he is my Master and I'm his pet. Do you think I should wait to bring up the something like me playing with his cute butt until he is more used to being a Master?
Replies:
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.