Dear Ty

Dear Di,

I am a 26-year-old healthy gay man, but I have a problem with topping.  Now don’t get me wrong, I very much enjoy the art of anal intercourse, but I just can’t seem to get it right.

When I’m intimate with someone, I still get aroused and get an erection. But when it’s time to do the deed I get flaccid quickly, and when I finally do get it in all it takes is two strokes and I’m done.

This had caused me to be the bottom in most of my relationships and other encounters. But I don’t only want to be a bottom forever. I want to top too.

What would be your advice to help me become a better top?

-Can’t top it off

Dear CTO,

It can be frustrating going flaccid right before penetration, but as long as you and your partner remain patient with one another, there are plenty of things you can do to become a master of being on top.

Some of this may just boil down to performance anxiety, since topping is not your go-to position. If you have a stable partner, I would recommend trying to be the topper for a month. Even if you go flaccid a few times, take a break and return to kissing and caressing until you get hard. Then try again, but don’t forget to be patient with yourself.

Cock rings can be a great boost to your performance as well. You can try incorporating them into your sexual play and see if they make a difference when you’re on top. However, I would stay away from drugs like Viagra to assist, as they do have side effects and should only be used if there is a physical problem with erection.

It might be beneficial to consider the psychological reasons that may make you go flaccid. Does being on top make you feel more vulnerable? Pay attention to what thoughts enter your head as you’re about to penetrate your partner, and reflect on them later on.

It also goes without saying that communicating openly with your partner about your desire to be on top is important, since you need to work together to make it happen.

At the end of the day, with a little patience and perseverance you’ll be the top dog in no time.

Love,

Di


Dear Di,

I’ve always wanted to try pegging with my boyfriend. I think it would be a great experience for the both of us. How could I bring it up without scaring him off?

-The art of pegging

Dear TAP,

Pegging—for those of you who don’t know—is when a woman takes the driver’s seat during anal sex and penetrates their male partner with a strap-on penis.

While it might sound super scary to the uninitiated, you should remind your boyfriend (if he’s open to the idea) that pegging can actually be a great way to walk a mile in your partner’s shoes and gain deeper empathy for one another.

For men, sex is usually something that happens outside the body, so when the roles are reversed it can be an enlightening experience of how moods, emotions, and sexual arousal can be affected when you’re being penetrated.

On the other side, women can use this practice to communicate with their partner in a different way.

So be open in your communication, and explain how pegging can really help the both of you grow in compassion, intimacy, and understanding. If you don’t want to directly admit you’d like to peg, you can just bring up the topic in a casual setting and gauge your partner’s thoughts or reaction.

You can always say that the idea came to you after browsing for strap-ons at a sex shop. Or you could always claim that you read about it in the Fulcrum.

It wouldn’t be the first time someone’s used Dear Di as a catalyst for some kinky sex.

Love,

Di


Five tips to help you prepare for anal sex

1. Make sure it’s something you actually want to do, and not just something you’re doing to please your partner.

2. Lube, lube, and more lube! Your anus isn’t self-lubricating, so to ensure everything goes smoothly use lots of lubricant.

3. Prepare your space. Some people are more comfortable laying down a towel, since it prevents the lube you’ll be using from getting all over your sheets.

4. Relax. Your sphincter needs to be very relaxed in order to let anything in—otherwise, the sex can be quite painful. Having an orgasm before doing anal can also help you relax!

5. Start slow. There’s no rush, and you don’t want your muscles to tense up as this will cause some real pain.