Alexander Cheves is the author of the bestselling My Love Is a Beast: Confessions and runs the popular queer sex advice blog Love, Beastly where this post originally appeared. Please visit LoveBeastly.com to submit your question.
Hey,
I just wanted to thank you so much for the article "17 Tips for Being a Better Top." I'm 47, have just rejoined the gay scene after an 18-year marriage to a woman (I'm bi) and I'm dating an incredible young guy. We talked about how I wanted to be inside him and he's bottomed before. The problem is I'm on the large side down there (7 up and 6 around). I'm also new to full gay sex. In fact, this young guy was my first. He's using what he calls "bum tablets" to clean house and we've bought some plugs. We've managed it twice but I'm really struggling for a third appearance. Every time I ask to try during a hot and heavy session I get the push back, and one time I was so stressed, he was ready, and I lost my erection. THAT was a pain in my ass, I can tell you!
Anyway, my question (assuming you're still reading) is... what advice can you give to this new top?
Thanks again for the advice in the article.
Hi Top,
Congrats on having a nice dick. You really just need practice.
You're a beginner to a fun -- albeit challenging -- sport. Like all sports, gay sex requires time, patience (with yourself and your sex partners), and practice to develop your confidence and skill. There's no fast track to mastery in any area of life and sex is no exception.
I think it's best for beginners to have sex with many different people for a few years. More information -- more data, more partners, more diversity -- means faster learning (think of it like taking on a heavier course load, Advanced Gay Sex 101). But if you're in a monogamous relationship this might not be an option.
At your age, you -- like most penis-wielders your age -- will have erections with minds of their own. Most men over 30 have a hard time staying hard for extended periods. Some men are lucky, but most of us appreciate some help. I certainly do. Boner pills like Viagra and Cialis are great if you are cleared by a doctor to use them.
When you say your guy takes "bum tablets," I assume you mean fiber pills. There is not enough space here to write everything I would tell him to encourage him sexually -- that's what I did in this post, this post, this post, and several other posts on my blog (questions about bottoming are the most common ones I receive). Most bottoms struggle with things like cleanliness, shame, performance anxiety, tightness, and much else, yet most bottoms love getting f*cked when it happens. The struggles of bottoming are worth the work we put into it. Bottoming is great. "Total tops" go versatile after one successful bottoming experience. Bottoming is transformationally good. So here's my personal message to him: don't give up, and take a look through my blog.
He needs practice, too -- ideally with many different partners. I always advocate for non-monogamy and encourage couples to explore it. You both would benefit from more play with more people. If that's not on the table, you will still grow as a top -- and he will still grow as a bottom -- but you'll grow as a top for one kind of bottom: him. And he'll only learn how to bottom well for you, which might not prepare him for a world of dick that will be even more accessible to him whenever things sour between you two. (Sorry to say that in such blunt terms, but no relationship lasts forever.)
Let's talk more about the benefits of non-monogamy in the short term -- in your immediate sexual future. Let's say, for example, that he's a submissive bottom. Think about how much you'd learn how to please him if you were simultaneously f*cking a power bottom, a power vers, a toy pig, and other guys who enjoy anal pleasure. Your skills would become varied and diverse. You would discover new things to try out with him. What I'm about to say will rile monogamous people, but strictly, serially monogamous folks are rarely very fun or adventurous in bed. Sluts learn more ways to f*ck by having sex with more people. This is why we're so much fun to bang.
As far as topping goes: start gentle, go slow, and build up your speed. You'll feel him gradually relax, though some high-quality silicone lube will help. Vary your speed and rhythm -- don't just jackhammer until you cum. Try deep slow strokes followed by one hard, fast thrust. Build, release, build, release. Monotony kills sex.
Take breaks. Most importantly, you should ask him what he likes and what feels good to him. Don't pretend to know exactly what you're doing. Treat sex as something you are figuring out together with complicity and mutual curiosity. Listen to his input. Let him take over sometimes, then take back control. Great sex is a constant exchange of power, sometimes from moment to moment. Even very submissive bottoms constantly have to be wrangled -- they are constantly surrendering, then tightening back up, in and out, over and over in a lovely dance of power exchange. Let them resist, breathe, then relax back into getting f*cked. When they relax, let you in, and let you make them feel good, it is glorious. This is the best part of using someone's hole: the moment they let you do what feels good to you because it feels good for them, too.
Sex is a marathon, not a race. Don't allow thoughts about how long you're taking to creep into your head. If he rushes you or pressures you to do anything, he's not being a good playmate, and that's on him. There's no ticking clock, no average duration period, and no one tapping their foot for you to orgasm. Just as you should listen to his feedback, he should listen to yours. Tell him what feels good for you, too.
You'll know when he's ready for you to plow, but even when he's begging for it, wait. The most enjoyable elements of sex are the expectation, buildup, tension, and denial. You'll let him have it when you're ready to give it. But rough, hard sex is never mandatory and some bottoms simply don't enjoy it, so as with all things, listen and work together to make a fun time happen for both of you.
Love,
Beastly
How To Be the Best Top You Can Be
How To Be the Best Top You Can Be
Topping is an art form, and there's a lot that goes into it, explains advice columnist, author, and queer sex writer Alexander Cheves.