I’m going to show you little-known techniques that will allow your partner to experience the ecstasy of bottoming without any of the pain he’s come to fear or associate with it.
First, you have to heat up his desire so much that his body aches for your hard dick to be inside of him. ACHES.
If he wants you in the worse way, 
his legs will begin to part and his sphincter will start to quiver with the right kind of anticipation-pleasure, not pain.
It means teasing him with your hard-on, letting him feel the heat of your hardness between his legs and on but not in his anus.
It means getting on top and kissing him passionately so that he can feel the excitement of being underneath your body.
This column is part one of a new weekly sex-ed series from Woody Miller, sex advice columnist, and author of the best-selling book, How to Bottom Like a Porn Star and How To Top Like A Stud: A Penetrating Guide to Gay Sex
1. First, get on top of him. The best way of bringing out somebody’s submissiveness is to let him experience the power of your body.
4. Put lube in his hands, place them underneath his ass and gently thrust your penis into them as if it were his anus.
This series combines porn industry secrets with innovative techniques from the latest gay male sex research
He’ll feel how smoothly it glides through his hands. He’ll feel the strength and the firmness and imagine it going inside him.
6. Take his hand and put it on your erection. Make him feel the strength and power of your manhood.
7. Now, slowly place your dick between his legs so that he can feel the heat and the hardness on and around his anus and perineum.
9. Play with different frottage angles and positions, making sure that you occasionally put his hand on your erection to heighten his desire. This will also make you want him even more.
11. It’s imperative that you start slowly and sensitively. And have some fun with it. This is going to feel really good.
12. Stroke the surface of the anus slowly, teasingly. Do not just jam your fingers in as if you’re going to finger fuck him.
14. When it comes to your ass, an inch can feel like a foot. Make sure you play with his penis so that he associates the insertion of your finger with pleasure. Again, do not finger fuck him by moving your finger in and out. In fact, once it’s in don’t move it and keep playing with his penis.
15. Once your finger is in there comfortably, playfully ask him to tighten his sphincter for as long as he can (he won’t be able to do this for longer than 20-30 seconds). Stay with me as there is a very specific reason why you’re doing this.
16. Keep your finger inside him while you suck his dick. Without realizing it, you’re training him how to relax his sphincter. You see, if you can get him to consciously tighten his sphincter right before you enter him, he can only hold it tight for about 30 seconds.
18. You can also insert a prostate massager while you suck him off like Rude Boy from AdamMale. It’s great because it’s perfectly shaped to locate and massage his prostate. Plus you get 30% off and free shipping with code GRIND. Always good to keep a good fuck buddy nearby to heat up the hole.
