Hold on to the Bottoms’ waist for control, subtle direction, and stimulation. If you’re the Top holding a Bottom, hold his waist in doggy position allows you depth control. Instead of thinking about going deeper think about using it for shallow thrusts---only an inch or two---a light “touch” into him.
Hold his arms for domination and control of his body. If you’re taller than him use your body from behind rather than simply being on top of him face to face You can lay on top of him, spread him out and run your body along his, varying your bodies position in relationship to his so your penis actually turns and your pelvis directs it in at differing angles. Penetration is not about simply in and out, it’s about speed, girth, depth, shallowness, resting, his anus becoming accustomed to your penis, his body relaxing more and more until the sensation of removal of your penis, because his body has fully and gratefully come to accommodate it, is shocking and excruciating as the initial insertion.
Use the length and weight of your body to rub the back of his body.
No focus to his ass/anus---everywhere but (pun!)---spend more time touching the entirety of his body. Even if you have to time yourself (give yourself 10 minutes) to just use some of the previous tips to give you other ideas/areas to focus on.
Use your tongue as a suggestion of your penis of what your penis can do outside of his body, along his body and then that brings you to analingus (rimming).
Most Tops go for the gusto in penetration but instead take your time with your tongue, your fingers, the knuckles on your hand, the flat of your hand, your forearm, your thigh against his anus. Think about varying kinds of touch when doing this but make it a point not to use your penis for 10, 15, 20 minutes. Use other parts of your body to suggest your penis.
When you finally agree/decide penetration is going to happen with your penis you want to first have used your fingers, mouth, even breath to have relaxed the anal area. A “cold” penetration won’t be met with comfort. An anus is not a vagina; it requires a man to relax two sets of muscles and lubrication. Interior and Exterior Sphincter Muscles.
Lubricating your fingers and starting 1 finger, 2 fingers, 3 fingers, you can assist a partner by first inserting one finger and letting it rest in through the exterior and the interior sphincter until you’re definitely into the rectum. With that one finger you can then start a pressure to “widen” the interior muscle. Push to one side, push to another. (One of the best lubes out there is Gun Oil which you can buy at most CVS, Duane Reades…at least here in NYC, adult stores, online, etc. It’s a silicone based lube instead of water based so it lasts longer and creates more of a permanent slickness to a penis, fingers, sex toy.)
With two fingers inserted open them like you’re opening a pair of scissors. Men often try and drive fingers in and out but when you know that there’s very little feeling doing that you understand that fingering is also helpful for relaxing both muscle groups. In a way you’re trying to “open” him up.
Three fingers are about the width of the average penis so this is when you know a partner is ready. Some partners don’t find fingers comfortable but you can still use the heel of your hand, your knuckles, rubbing you fingertips.
The first penetration should be by the Bottoms direction, remembering you’re easing in first past one sphincter next and then the next.
Stop each sphincter set and hold, don’t thrust. Let his body become accustomed to your presence in his body. Count to 10 or 20 and then push in a little deeper. No thrusting yet.
To that end, think about applying lubrication into your partner first and mainly onto the shaft of your penis, along the sides of the condom, because that’s where the friction (pain) will come from the most.
First try micro thrusting. Check out the anatomy lesson of the rectum, the highest level of nerve clusters are by the front of the anus. Trying to go “deep” really is more of psychological pleasure for maybeboth. And again you have only a handful of inches in depth within the rectum. Anal sex pleasure comes from the pressure and friction to that nerve cluster and massaging of the prostate.
A Bottom’s pleasure in being penetrated is twofold---the nerve cluster and the psychological pleasure of being “filled”, a man in him, the pleasure of being enveloped by another man. The thrusting is a part of that but not the totality so you have to consider that the thrusting you might get pleasure from isn’t where he gets the totality of his pleasure from.
Vary speed and thrusting depth to satisfy you both. Shallow, micro thrusts will activate his nerve clusters. Deep thrusts will feel more pleasurable to you the Top because of the head and shaft of your penis being stimulated by the grasping sphincter and rectum.
Take breaks, remove your penis, do other touching and caressing, changing condoms for more oral sex, cleaning each other with wet towels. Then return to anal sex. Repeat. This is one of the ways that men example stamina, not by a penis that is hard for six hours but by finding a rhythm and penetrating when they’re at Heat again and again and doing other things when not.
I recommend 3 other Texts for this, I can’t show the graphic pics in my books here or that I generally project, sometimes as high as 20 feet in a classroom/workshop of male genitalia and all of the orifices and such but the below books will talk further about bodies, positioning (I’ll add another answer) and emotionality and intimacy to get to finding and negotiating with a Top for the best experience and for Tops to understand how to have a sensational time with other men. Enjoy!