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Savage Love

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I'm a guy who can't orgasm during oral sex. I can during vaginal. It's frustrating. I get close but don't quite reach the apex of that hill. I suspect it's a control issue. During vaginal, I have some level of control – during oral, I don't. Help.
Almost There

Maybe it's not a control issue, AT. Maybe it can't get you up and over them thar hills because … oral doesn't do it for you. If it were your girlfriend who had difficulty climaxing from oral alone – let's say she required a vibrator to get her over them thar hills – the standard-issue, sex-positive, lady-empowering advice would be to accept that it's just the way her pussy works.
Vaginal gets you all the way there, oral gets you almost all the way there – maybe that's just how your dick works. On the off chance there could be a psychological block, experiment with letting her get you almost all the way there and then stroke yourself to get the rest of the way there. Stroke to the point of no return, then put your dick back in her mouth and blow your load. With time, you may find the number of strokes you need to get up and over the hill diminishing. Or you may not – because this may be how your dick works.

My girlfriend and I are having sex on a not-so-every-day basis, but that doesn't matter anyways. The thing is, I've been lasting longer and longer every time we do have sex. However, she can't last as long as I can, and eventually we'll start having to use lube and then maybe 30 minutes later, it'll start to hurt more. As if I'm "tearing" her or something. I'm left "blue-balled" for fear of hurting her further, and she feels bad for not having me finish. What do I do? Fake it or just use copious amounts of lube?
Bluer And Bluer Balls

Who says you can't finish? If it's taking you forever, and your girlfriend's pussy is giving out, pull out and stroke yourself until you finish. You could also incorporate strategic stroke breaks into your fuck sessions to get you closer to the edge and give her pussy a rest. And you might find she's able to last longer if you engage in a little midplay – think foreplay, but halfway through – during those stroke breaks: Make out while you stroke yourself, eat her pussy, play with her clit. I bet your girlfriend will need less lube if she's less bored
and/or more turned on during those epic fuck sessions.
My new book – American Savage: Insights, Slights and Fights on Faith, Sex, Love and Politics – comes out in May. Order it now!

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