Ask Slutever

Photo by Terry Richardson <3
Hi, I’ve been a huge fan of your blogs and you as a teenage boy growing up that has never been laid before (sadly, it’s true). I learn a lot from your videos and blog posts. Can you tell me more about how it feels like to have sex for the first time? Thank you! Ken

Strong question Ken. Having sex for the first time can feel a variety of a different ways, though it can usually be summarized as one of the following: painful, terrifying, anticlimactic, freeing, overwhelming, or just like nothing at all. For me, it felt like nothing at all. 

I lost my virginity in high school, and because my boyfriend at the time and I had decided a couple weeks in advance that we were going to have sex, we had some time to prepare. Part of the prep involved him fingering me a lot in order to stretch out my vaj, so that the “first time” wouldn’t hurt. In hindsight that sounds really clinical and un-sexy, but back then it just felt clever. Although to be honest we may have been a bit excessive with the stretching, because when he finally put his dick inside me I couldn’t even feel it. Although actually, that occasionally still happens to me during sex now. Maybe I just have a wide-set vagina? Unfortunately, I don’t know what it feels like for a boy to have sex for the first time. I imagine it feels like the inside of a plastic bag, inside of a warm, moist cave. And like becoming a man.

When you’re a virgin, your “first time” seems like the biggest deal ever, and the anticipation of it consumes your life. This is why I usually advise people to just lose their V-card at the soonest non-awful opportunity possible, this way they can move on with their lives and start worrying about something more important, like clothes or blogging or politics. 

I have been dating my boyfriend for just over a year. After 5 months of long distance, I recently moved across the world to live with him. However, since the move our pre-existing problems have intensified. I cheated on him twice in a week (only kissing), after which I knew I had to break up with him. He responded saying that I owed the relationship another chance, because I hadn’t communicated my problems to him prior to the break-up. I agreed, and we’re still together now, although I have moved out, and the relationship is actually better than ever. The problem is that I have all these thoughts about being desired by other men and having sex with other people, and when I get drunk these ideas become more powerful and less reasonable. I’m 23–aren’t these the years I’m supposed to be slutting around? I feel like I’m not fulfilling my slutty potential. On the other hand, I’m really enjoying being with my boyfriend right now. Advice please!

Jesus, I wish I had the answer to this. This has been a primary main problem in my life for the past decade: I want the romantic comfort of being in a relationship, but I also want to sleep with literally everyone. Thus is the slut’s dilemma. Unfortunately, we can’t have our cake and eat it too, as I recently discussed in an article for Vogue about open-relationships. I would suggest an open-relationship for you, but since you’ve been monogamous for so long that would most likely be a difficult step backward. Also, if there’s one thing being “open” has taught me, it’s that there is such a thing as having too much cake, and that maybe it’s actually better not to be able to eat your cake, rather than to eat too much cake, because cake is really fattening.

Anywayz… it’s normal that you want to fuck and be desired by other men. The fact that you just moved to a new city is probably not helping either, because you’re surrounded by a whole new crop of hotties/potential hook-ups. We all want to be desired–it makes us feel confident and powerful–but being desired and sleeping around are not one in the same. Restraint is extremely desirable. Knowing that someone wants you, but denying them sex, is probably more of an ego boost than a sloppy one-night-stand in the long run.

What I’m learning as I grow-up is how valuable and important it is to be in control. Having sex with lots of people is cool, so long as that’s what you want, and what makes you feel good. Having sex with lots of people while you have a boyfriend, feeling uneasy about it, doing things you regret, and hurting the people you care about in the process, however, is not so cool. See what I’m saying? Having control is not about being a prude, it’s about knowing what you want and how to get it.

So, my suggestion for you is to try to rein in the slut-works for a bit, and make an effort to save your relationship. You guys lasted five months of long distance, you moved across the world for this guy–those are big things! He must really mean a lot to you, and to throw that away because you’re having a moment of intense hornyness might be something you regret later on. Believe me, 23 is will not mark the end of your desirable ho years. 

My advice is to take a few weeks where you really focus on your relationship. Make an effort: go on dinner dates, have amazing sex, go out of your way to do nice things for your bf, and see how that makes you feel, and what you get out of it. But don’t do it half-hearted and make-out with other guys in the process, because that will contaminate the experiment and make the results all fucked-up and impure. Then, after a few weeks, see where you stand. If you still want to break-up, then do it and go crazy.



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