First, what is a top? A top is the person doing the penetrating during anal sex. Despite what some perceive, the top isn't always the most dominant partner in the relationship. Giving or receiving anal is a personal pleasure preference.
How To Top
So, how do you top? There a certain level of finesse and a number of techniques beyond just sticking your penis into his anus that make one a good top. Topping takes strategy, a way to execute that plan, and a lot of patience. The strategy I'm referring to is the bottom's pleasure. A good top knows that focusing on their partner's desires can reap pleasurable rewards for both people.
Sounds like a lot of work? Well, it's not as difficult as it sounds or even necessary, but if you want your bottom to come back for more (again and again), lean into these techniques:
Good topping is more than just jumping on the first available opening. Keep your bottom wanting more by developing your style, or the way you prepare your bottom for anal. Your bottom should have already made preparations for cleanliness, but topping takes prep as well—prepping your bottom.
Most anuses aren't designed for entry and aren't relaxed and expanded in its natural state, so penetration can be quite painful for your bottom (and less enjoyable for you) if his sphincter muscles aren't relaxed. It's easier for him to relax his sphincter muscles if he is relaxed.
Relax Your Bottom Partner
To relax your bottom, start with foreplay and a mixture of firm and light touch and kisses. Read his body language and focus your attention on areas that help his entire body loosen. Listen to his breathing and verbal cues. Let him and his body guide you to the right areas.
Stay above the belt for some time with kisses and caresses, which can be difficult, especially when you're ready to go for the prize (remember the patience we talked about?). Next, undress him slowly and let him undress you as well. Relax your body on his and let him feel your heaviness. Press against his torso. Start rubbing around his waste and eventually below. Kiss, touch, and let him feel your readiness.
If he's into it, let him give you oral. Meanwhile, explore his waist, butt, and anus. Try rimming, massaging his perimneum or lightly penetrating him with a lubricated finger or toy.
Let Him Guide You, Then Take Control
Increase his eagerness but focusing on his relaxation. Let him guide you when he is ready, then take control. Remember that the anal cavity isn't an endless cavern. Start slow and ease penetration. Be patient and develop your rhythm before increasing your depth and speed. Again, listen to his body language and verbal cues. Does he tense up or relax certain speed and certain depths?
Hopefully, you'll both sync into a rhythm. Once this happens, maintain that pace and slowly increase depth and speed.