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Anonymous asked :
Hi Sir, After several years I finally got myself a date that I have an emotional connection with. We've been on a few dates but on this most recent one we slept with each other (fooling around, no actual penetration). It was an extremely hot situation and while he was able to finish, I was unable to (despite him being very determined to get me over the edge). I feel like my boot/glove kinks will help me finish if we do this again, I'm just not sure how to bring them up. I asked him about his kinks (I felt like if I knew his I wouldn’t feel so awkward talking about mine), but it doesn’t seem like he’s into anything non-vanilla. Do you have any tips that I could use to tell him what I’m into without him thinking I’m a freak? (I know that if a man is dismissive to my kinks then he’s probably not a good choice for me, but he’s so dreamy and I’ve been searching a long time for someone like him XD )”
Alexander Martin:
Thanks for the question (and the patience with me getting back to you)! Ok, I hear you that you’ve considered that he might not be a perfect fit and you want to give him a try despite that. That’s fair! I’ve done the same.
Statement: I was unable to [cum] (despite him being very determined to get me over the edge). I feel like my boot/glove kinks will help me finish if we do this again
Comment: Tops actually have this problem a fair bit although they are loathe to discuss it, both due to ego and due to a small stigma around it from bottoms. Did you know that some birds deposit sperm sacs in their partners within seconds only to fly away afterwards? There are a number of animals who out of necessity have evolved to have very short sexual intercourse. Humans? We’re not one of those species. I know that gay culture idolizes the stud who is always hard and ready to cum on a moment’s notice but that really doesn’t last.
I’d really recommend slowing down sex and making sure as much as possible to take pressure to cum for either of you out of the equation. Putting pressure on yourself is one of the surest ways to either massively delay or prevent ejaculation. To relieve pressure, make sure you don’t have any time commitments that day, make sure he knows that there shouldn’t be any pressure on you to cum, and lastly (if you’re a tense person) consider a little weed or light inebriation to help you unwind and relax. Once all that is out of the way, make sure that you’re teaching him how to touch you in the ways you most enjoy (he needs to know as your bf anyways). Take your time, I’d even recommend edging a bit if you can manage it. I’d also advise rounding all that out with an explicit understanding that if you DON’T cum it’s not an indicator that you didn’t have a good time. You might not cum that time, but you will be more likely to cum with him in the future once the pressure goes down.
Question: Do you have any tips that I could use to tell him what I’m into without him thinking I’m a freak?
Answer: You can write him an email. Be careful with your wording. Be sure to phrase the kink as a good thing he gets to indulge in. Along those lines, be sure to tell him what’s so hot about what you want him to do. The best way to entice a person to a new kink is to expose them to someone who LOVES the kink (that’s you) so they can see not only the effect but the sincerity you have in loving it.
Support: As for thinking you’re a freak? I hope that ends up being your mind telling you mean things and he doesn’t react like that. If he does act or react like that then there is likely nothing you could have done to present it. All my advice above is assuming he’s at least neutral or doesn’t know what to think. If he’s opposed then there’s nothing you could have ever done to convince him to give it a chance. Not to scare you, but when it comes to kink… Only some people are into it. We’re likely born that way. There are vanilla folks out there who’ve never tried it and never will. Seems odd to me personally but I’ve met them. Regardless, the only way for him to get into something is to be exposed to it. Also, not to judge at all, but the boot/glove fetish seems like a low bar to get over. Putting on boots and gloves just to get you worked up a bit for the main event seems pretty easy.
But hey, I’m happy for you. I wish you the best of luck on this. I hope it goes the way you’d like it to. Let me know how it turns out.
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