My boyfriend is very willing to explore sexually with me, and loves me for the fact that I am so liberated and willing to try new things. However, there is one thing he is very shy about: his ass. Ever since he went down on mine, and took my anal virginity, I have been dying to give him that same pleasure. However, he is one of those men that, to a certain extent, equates anal penetration with homosexuality in men. I have told him I want to go down on his ass, and he is willing to let me, although I haven't done so yet. He knows I would like to try pegging, but I think he is a little afraid of it. Any ideas on how to gently ease him into ass play?
This is really one of those questions whose answer will be different for everyone. Rye has always been so excited and so pleased by any foray into anal play, that his answer would likely be, "Gentle? For what?" His enthusiasm is such a large part of why we all love him so much.
For me, though, a gentle introduction was definitely required. Not because of any prudism on my part (obviously), but because prior to Rye, I had really been mostly on the giving end of anal pleasure and rarely the receiving.
To get this out of the way, as there is really no other way to say it: wanting someone to do things to your ass that feel amazing does not make you gay. Wanting to have sex with men makes you gay. Or at least bi. That's all.
Now, as to a gentle ease-in, there really is no better starting position than a rim job. He's already said he's willing to do this! What are you waiting for? Your tongue is one of the softest and gentlest ways to help him realize that anal play is a really great idea. To set him at ease, make sure you've both just showered and are clean as whistles. That will remove a lot of the stress and trepidation that sometimes comes along with this stuff. While you start teasing him with your tongue, don't forget about his cock. Sometimes, a gentle stroke while you lick his ass will help distract him from feeling self-conscious about what you're doing back there.
Once you've convinced him with your tongue (and you will), move ahead with fingers. Any protest on his part will absolutely be quieted by you being calm, determined and not making it seem like a bigfuckingdeal. And lube. Lots and lots of lube. Our asses don't self-lubricate, so this is a serious must. We like this one.
Think of massaging his prostate the way you massage your g-spot. It's kind of a gentle "come hither" motion. As always, check in with him on how it feels, whether he wants it faster or slower, more fingers or less fingers, etc. Once you've given him one solid prostate massage while riding his cock, (in my experience) his appetite will be whetted and he will be the one asking you to put things in there. As you venture into toys meant for anal play, get him something relatively small with a powerful vibrating motor. Don't rush straight to pegging, there is lots of fun to be had on the way there, but, like I said, once he discovers how good all this feels, his worries about this will be significantly relaxed.
Best of luck, and enjoy! You are about to give your partner a kind of pleasure he's never experienced before, and that is a really, really special thing.