Hi James, this might be a weird ask but I would just like some advice. I’ve never been able to make myself cum and neither has my boyfriend. This tends to happen because I get to sensitive to continue because it hurts. Do you have any advice for me/us on how to push myself farther so I might be able to get over that edge?

Hi anon, well as I’ve just written about, an interesting twist might be deciding you don’t want to try, and stay a BNIB.

But, if getting oversensitive is what’s keeping you from cumming there’s a few options.

First is to explore penetrative stimulation – I’m going to assume the over-sensitivity is clitoral, which means you could focus on g-spot stimulation with fingers or a vibe inside you, and that’s going to be another route to cumming. If your over-sensitivity IS internal then the opposite applies, go for cumming from clitoral play, but it’s more like the former.

Your best best is mixing the two together, and then using g-spot play to take you over the edge. Keep your breathing steady but lungs quite full, work on building up the sexual ‘pressure’ and try to keep your mind clear of anything besides how good it feels and how sexy you are.

Another route, again assuming we’re talking about your clit getting overly sensitive, is for your boyfriend to become an oral zen master. Nothing combines stimulation along with gentleness quite as well as good cunnilingus, and compared to fingers or a vibe it can take you to and over into orgasm much more gently than anything else.

Luckily I’ve written Tumblr’s most popular guide* to how to do this like a pro:

http://edging.space/post/157590444398/how-to-give-cunnilingus-like-a-superstar

(*Based on no evidence at all)

Another route is to tackle this thing straight on. What you’re experiencing as ‘pain’ is possibly more complex than that, things get weird with pain and pleasure when you’re near orgasm, and it might just be that you haven’t quite pushed through to it feeling good enough that you don’t quite know how to process what’s going on.

So with safewords in place, I’d try tying you down, kissing and rubbing and fucking you until you’re really turned on and close, and then using a really powerful vibe like a magic wand to just see what happens if you don’t have the option of it being pulled away. I would suggest it’s likely (but not definite) that if you just get past what you feel as ‘pain’ you’re going to cum, really fucking hard, and your body and brain will have a kind of ‘Oh THAT is what was about to happen!’ revelation.

I would hope there will be a physical and emotional release (which might take a few tries to find) that’ll flip a bit of a switch. Worse case scenario is you’ll experienced a bit of what for most is ‘post orgasm torture’ and you’ll discover it’s a whole new kink for you (or decide NOT to try that again 😛 )

Try some of those out, see how you get on, and let us know!

James xx

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