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. This series combines porn industry secrets with innovative techniques from the latest gay male sex research.

Say goodbye to failed attempts at intercourse because your partner couldn’t take the pain.

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.

I’m also going to show you how to suck his dick while you fuck him.

Let’s start by helping him concentrate on desire, rather than fear of your hard dick.

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.

His body will swallow your dick.

Getting him to that level of desire is actually pretty easy if you know how to work it.

Working it doesn’t mean slamming it into him.

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.

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.

2. Being on top of him makes him feel safe and wanted.

3. Gently make him feel your heat, smell your essence, and feel your hardness

4. Put lube in his hands, place them underneath his ass and gently thrust your penis into them as if it were his anus.

He’ll feel how smoothly it glides through his hands. He’ll feel the strength and the firmness and imagine it going inside him.

The Tease

Next up is frottage AKA The Tease. [non-penetrative sex]

5. While you are on top of him, slowly part his thighs with your knee

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.

8. Slide it in and out, and back and forth in an undulating motion.

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.

10. Now is the time to put some lube on your fingers and explore his butt.

Lube is 35% off here.

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.

13. Insert your finger slowly. Did I say slowly? Because I meant S-L-O-W-L-Y

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.

Build Sphincter Trust

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.

Now is also a good time for a blow job

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.

17. When the sphincter involuntarily loosens, that’s when you penetrate him.

18. You can also insert a prostate massager while you suck him off like Rude Boy from AdamMale.com. 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.

If you found this helpful so far: check out the book where this advice came from: How to Top Like a Stud: A Penetrating Guide to Gay Sex

Do you see where I’m going with this?

The key is to keep his sphincter relaxed as you enter him with your dick.

19. Now you’re ready. Go ahead and eat him out for about 15 minutes. Or skip to the next step.

20. Next, you’re going to put the head of your erect penis comfortably, but snugly on the outside of his anus. There should be no space between the opening of the sphincter and the head of your penis.

21. Once your cock is snug against his anus, ask your partner to clinch his sphincter as tight as he can for as long as he can. He’ll be able to do that for about 20 to 30 seconds maximum.

The goal here is to have his ass swallow your cock. Yup, that’s what’s going to happen.

22. As you approach the 20-30 second mark you will be able to tell when it starts to relax involuntarily by the look on his face. Ask him to tell you anyway because you need to time this correctly.

23. As he begins to relax his sphincter start penetrating him with your dick. His body will beg for it.

24. You’ll notice how easy –and painless–it is to get it inside him.

25. Now, notice what just happened: You are entering him at the point that his sphincter is most relaxed. You’ve used physics and physiology to create an ideal time for penetration.

26. As an added bonus, suck his cock while you fuck him with the Autoblow2. It feels like the real thing and you can get $40 off with code GAILYGRIND.

27. Have him hold the Autoblow while you’re fucking him and the beaded rings will suck him off while you fuck him. You won’t be able to get him off you.

3 more tips for every top

First, check out the book, How to Top Like a Stud, where this advice came from. If you have a boner now, wait to you read this. You can start reading it right now because it’s a PDF that instantly downloads to your pc, Mac, phone or tablet.It includes even more techniques to keeping your partner’s sphincter completely relaxed, how to overcome hygiene worries and includes new speed, depth and thrusting techniques.

Second and third is the Rude Boy and the AutoBlow 2.

Rude Boy is 30% off with free shipping in the U.S. with code GRIND.

AutoBlow 2 is $40 off with code GAILY GRIND.

Rude Boy



As the old saying goes, every gentleman should have one good prostate massager. Rude Boy is good because it has the perfect angle for entry, and will simulate your finger with an added vibrating effect. Its rated five stars and feels really good.

“I bought this for a little experimentation. It is not too big, but it really does hit the right spots, and when you add the vibrations…amazing!” Olivier, NYC

AutoBlow 2





$40 OFF with code GAILY GRIND [Offer ends February 31, 2016]

Every bottom’s favorite toy. The AutoBlow2 is a lot of fun.

Think of it like a fleshlight on steroids. Just put it on your bottom’s cock while you’re fucking him and he’ll enjoy a hands-free solo blowjob at the same time. Oh, and the sleeve comes off for easy clean-up, which is always nice.

Bottom line: If you master toy play and the physics of the sphincter, you’ll be a much better top.

Get the full guide for How To Top Like a Stud below.





Did You Like This Wildly Clever Way Of Getting Your Partner To Relax His Sphincter?

Then you’re going to love the rest of the book where this advice came from.

You can start reading it right now because it’s a PDF that instantly downloads to your pc, Mac, phone or tablet. It includes even more techniques to keeping your partner’s sphincter completely relaxed, how to overcome hygiene worries and includes new speed, depth and thrusting techniques. You’ll also learn how to discover your inner top and how to get hard and stay hard, even with a condom. Click here for more details.

When the tops are away, the bottoms will play

Special gifts for that special bottom in your life



For kinky bottoms

The cheeky boy for more hardcore action.

[35% off and free shipping with code GRIND]

For experienced bottoms

The luxury edition for bottoms that expect more.

[35% off and free shipping with code GRIND]

Continue Reading: How to Bottom Like a Porn Star: Best Position and Pain-Free Angle of Entry

A blog we love: Mindful Eating.

Disclosure: This post is brought to you by Gaily Grind Best Picks Team. We mention products and services you might find interesting, and if you purchase them, we may get a small share from the sale. Affiliate links used. Have something you think we should know about? Contact us here.