Gay Anal Sex: How To Bottom Without Pain Or Stains 2017-07-31T22:33:29+00:00

How To Have Gay Sex

What Stops You From Bottoming?



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Is This You?

You tried. It hurt. You stopped. You struggled to get it in but it hurt too much. At first there was a kind of an unbearable burning sensation mixed with a terrible pressure and then you stopped because of the pain. You tried to relax but you just couldn’t.

Or maybe you relaxed enough to get it all in but it felt weird, like you were going to take a dump on yourself.

There was little or no pleasure, a lot of pain and no sense of why so many guys like to bottom. So, you feel cheated. Everyone else seems to experience sexual ecstasy when they bottom but all you experience is pain and weirdness.

And the guys who want to top you (boyfriends, dates, or one nighters) aren’t helping. They kind of just say, “relax,” and try to shove it in. Or maybe they’re endlessly patient, but nothing works—it’s too painful or it doesn’t feel right.

Smells & Stains. Gross!

You might also be struggling with the “ick factor.” A lot of guys are grossed out by anal sex. If you don’t know how to get clean down there, the smell and the potential to leave tire tracks behind you can put you off completely.

It could be that you’ve never even tried to bottom.Maybe you really, really want to do it but you’ve avoided it because you don’t know what to do or how to do it.

Well, you’re not alone. I’ve been writing gay sex advice columns for the last ten years and the most common questions I get are, “How do I bottom without pain?” “How can I get myself clean enough?” and “Why does gay sex hurt so much?”

The rectum is not a straight tube. The pubo-rectal sling pulls the rectum in an “S” curve. The more pronounced the “S” curve the more pain you’ll experience with anal intercourse.

It may be that your “S” curve is more pronounced than say, your friend, the gay bottom who can swallow living room sectionals. If you knew which angle to insert your partner’s penis and how to insert it you’d avoid most of the pain.

And that’s exactly what my gay anal sex instant download guide shows you how to do. But before we get to that, there’s another thing you need to know:

Your sphincter has two muscle rings. The first is voluntary (you can squeeze it at will—it’s what stops you from taking a dump in the middle of a cocktail party even though you have to go badly). The second is involuntary (you can’t consciously control it—it’s why you’ll eventually take that dump in view of the host if you don’t get to a bathroom quickly).

It’s that second ring, the involuntary muscle (less than a quarter inch from the outer voluntary one) that causes most of the pain in male anal sex. If you can relax it you’re in for a great ride. If you can’t, you’ll punch your partner into the next room.



What If You Could Bottom

Like A Porn Star?

You’d experience another dimension in pleasure. You’d have volcanic orgasms. You’d shoot up to your chest and there’d be a lot more of it. You’d be a better top (because you’d know what it’s like to bottom). You’d become totally versatile. You’d be a better lover.

You’d Be Able to Bottom Without Pain

I put a team together made up of a gay sex columnist (me!) , a colon rectal specialist and a urologist to find the best solutions for you. We interviewed some of the biggest names in the gay porn industry – – performers, directors and producers. We took everything they said, combined it with our own knowledge and came up with the ultimate guide to gay anal sex: How To Bottom Like A Porn Star. It’s in the form a PDF file so it’ll download instantly to your pc, mac or mobile device.

…Without Smells or Worse

We start with the Sexhalation Method. It completely eliminates pain through systematic desensitization, progressive muscle relaxation, pattern breathing and sexual imagery.

Pain occurs when a large object tries to enter a clenched opening. Relax the opening and the pain disappears. But you have to relax BOTH of your sphincter muscles and that’s where The Sexhalation Method comes in.

What You’ll Learn In My Gay Sex Guide:

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You’ll Also Learn How To…


• Take Bigger Guys. You can do it without ending up in diapers IF you follow my careful plan, developed by a board-certified colo-rectal specialist.

• Overcome Emotional Blocks That Stop You From Bottoming. Does bottoming threaten your masculinity? Learn how to resolve the emotional blocks that stop you from trying or enjoying anal sex.

• Find Angles & Positions Best For You. Missionary? Doggie-style? Straight in? Angled up? I’ll show you which ones avoid pain and maximize pleasure.

• A Behind-The-Scenes Look At How Porn Stars Prepare For Anal. A spread-eagled view of the industry—how they avoid pain and keep themselves clean. Not for the faint–of-heart!

• Get Answers To Common Questions. Should you use poppers? What about Anal-eze? Why does your penis sometimes go soft when you bottom? How can you stop your partner from losing his hard-on when he’s about to enter you? Does bottoming cause hemorrhoids? All your questions answered.


It’s An Instant PDF Download.




    The Sexhalation Technique,© developed with a board-certified colo-rectal specialist virtually guarantees bottoming without any pain.

    Smells? Stains? GONE with the techniques in this guide. Bonus! Discover the little-known device that gets you as clean as douching but without the danger.


    By using our techniques, positions, and angles of penetration you’ll excite your prostate so much that you’ll cum more and harder than you ever have in your life.


This book normally sells for $19.99.

Hey! Can’t afford the full price of my books? You can today because I’m experimenting with the “Pay What You Think Is Fair” concept (with a small minimum). I will honor my 30 Day Money Back Guarantee no matter what you pay, so take advantage of me.  Er, I mean it.  Well, actually…  Are you on Tinder?  Seriously, ENJOY the #1 best selling gay sex book at whatever price you think is fair!    
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The author on the set with Greg Behrendt and Tyra Banks.

Istarted my career by syndicating a sex and relationships column all over the country and I sort of became known as the “East Coast Dan Savage.” I then went on to write my first gay sex book, Men Are Pigs But We Love Bacon (Kensington). Next thing I knew I was auditioning for a co-hosting role in a heterosexual sex makeover series called The Sex Inspectors.

With the screen test cameras rolling, I remember the production chief asking me what I thought of women faking their orgasms. “That’s nothing,” I sniffed. “Men fake whole relationships.”
I got the job.

The show went on to be an international hit, airing in 12 countries, including the U.S. on HBO. It led to my biggest book yet, Sex Inspectors Master Class: How To Have An Amazing Sex Life (Penguin).

I love giving advice to people. I love to see barriers crack and humanity come to the surface. I hope I’m able to do that with How To Bottom Like A Porn Star and hope you enjoy reading it as much as I did writing it.

how to have better gay sexRead More About How To Be A Better Bottom.



Want to take a sneak peek at some of the chapters in my book? Just click the tabs on the left and you’ll see excerpts from each chapter so you can get a sense of the content and style. I like to bootleg a lot of facts and insights into funny narratives. My goal is to teach you something while making you laugh. And if I fail, well, that’s what the 30 day money back guarantee is for!

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Does Gay Sex Hurt?

“Bottoming Makes You A Woman.”
This is the single biggest emotional stumbling block gay men have about bottoming—being labeled less than a man. For many of us, bottoming isn’t an opportunity to enjoy a pleasurable sexual experience but an act that threatens our sense of masculinity and the respect that goes with it. Many gay men believe that if they bottom they will become “a bottom.” They fear that bottoming will create a new unwanted identity for them; that they’ll become, ahem, the butt of everyone’s jokes.

It just may be that you haven’t been able to bottom (or been able to enjoy it) because you have so many emotional issues around the act. If you can get away from the falsehood of bottoming as an identity and see it for what it is—an erotic activity–the more relaxed and receptive you will be.

It might be helpful to understand how so many of us came to associate bottoming with effeminacy. The answer can be found in one of the most important gay books you’ll ever read–historian Byrne Fone’s, Homophobia: A History. He makes well-documented assertions that sex between men in Ancient Greece was “normal” and idealized, but that there were strict rules regarding its conduct. There were Homo Do’s and Homo Don’ts. And the biggest Don’t was to enjoy penetration.

Being the penetrator was synonymous with being a man. Anything that subverted the concept of masculinity was punished with social ostracism and ridicule. And nothing mocked masculinity more than getting penetrated.

Greeks and Romans didn’t really care whom you had sex with (women, men, boys, slaves) as long as you were the penetrator. The Romans even had a word for it: Vir.

It was an exalted term, symbolizing the ideal man: He who penetrates other men but is himself not penetrated.

Today we still live out those vestiges of antiquity. We label men “tops” or “bottoms” in part because we’re living out antiquity’s fear of the feminine. In heterosexual thinking, the penetrator (man) is more valuable than the penetrated (women). We’ve adapted that consciousness in our own community, where the penetrator (top) is more valuable than the penetrated (bottom).

Clearly, labels like “top” and “bottom” can be useful shorthand for sexual likes and dislikes. But instead of stating what we prefer– “I like to bottom”– we turned that preference into an identity—“I’m a bottom.”

By developing identities out of these labels we cut ourselves off of any unlabeled possibilities. In our world, tops can only date or hook up with bottoms and bottoms can only do the same with tops. That’s a whole lot of blindness in a sighted community.

I Call Bullshit.

Read More…

Gay Male Anal Sex

Relaxing your sphincter during anal sex will go a long way to eliminating pain, but it only gets you so far into the promised land. There are two other points of pain to watch out for. In order to prevent them from doing the devil’s work you have to understand a bit of butt anatomy. Let’s start with something that might surprise you.

You Have Two Sphincters.
You may only have one anus but two connecting sphincters surround it. They are distinct but overlapping bands of muscle tissue. And while they serve the exact same function (regulating grand openings and final close-outs) they go about it in different ways. You are most familiar with the external sphincter because you can order it to tighten and release. Here, try it. Squinch your starfish by using the muscles to stop yourself from peeing. Got it? Tighten, release, tighten, release. Now, this time with feeling! Tighten, release. Now do five fast tightens. Get it? You can boss that part of your butt around. Feel like taking a crap but there’s no bathroom around? No problem. You can will your external sphincter not to open. At least for a while.

But the internal sphincter? You can’t tell it to do shit. And I mean that in every sense of the word. You are not its boss. Like your blood pressure and heartbeat, you cannot directly control it.

Do this: Put your hands in front of you as if you’re praying. Now intertwine your fingers down to the webbing and press your palms together as tight as you can. Now keep everything connected and completely relax both hands. Notice the small opening between the side of your thumb and your index finger? This is the opening to your anus. If somebody tried to poke their finger through that opening it would feel snug but it’d go in pretty easy.

Now tighten both hands as hard as you can. The left hand is the internal sphincter you cannot directly control. The right hand is the external sphincter you can. Keeping the left hand tight as a drum, completely relax your right hand. Your right hand (external sphincter) is relaxed so a slight opening was created. But your left hand (internal sphincter) is so tight that it won’t let a poking finger through very easily.

Welcome to bottoming’s first dilemma: The left hand doesn’t know what the right hand is doing. Or more accurately, the left hand doesn’t care what the right hand is doing. The internal and external sphincter can and often do work independently of each other. In order to make penetration smooth and effortless both sphincters have to get on the same page. In the next chapter, you’re going to learn how to do that, but first, let’s talk about another pain in the ass. Did you know that…

Read More…

The Joy Of Gay Sex

The Sexhalation Method is actually quite simple but it requires you to understand a few things about your body. Let’s start by examining why so much of your butt tension is (seemingly) beyond your ability to control it. Do this: Tighten your sphincter as hard as you can right now for a count of five seconds. Notice how clamped down it feels. Now relax. Feels like you controlled your sphincter, no?

That’s a trick question, because as you already know, you have two sphincter muscles, not one. The whole time you were clamping down on your external sphincter your internal sphincter was chillin’ on the couch, sipping a cosmo, blithely unaware that its twin brother was being throttled. The external sphincter does not respond to your commands because like your heart beat, it’s governed by the autonomic nervous system.

You can’t make your heart beat faster by telling it to hurry up, but you can do things that result in a faster heartbeat (like pushups). We’re going to use this same concept with your internal sphincter, as well as that other involuntary pain point—the puborectal sling. You can’t will them to relax but you can do things that will result in relaxation. The first step in that direction is…

A Sexercise Plan For Your Sphincter.
The best way to consciously relax your external sphincter is, oddly enough, to tighten it. That’s because the first step to relaxation is awareness of its opposite–tension. This is a key concept to bottoming without pain: Your sphincter will relax more if you make an effort to tense it first.

Read More…

Gay Male Sex

We cannot have a conversation about keeping yourself clean without a full understanding of a delicate subject: How you eliminate waste from your body. The fear of leaving muddy tire tracks on the sheets or your partner’s penis is based on a misconception that feces are stored in the rectum. In fact, they are not. Feces are stored in the sigmoid colon, which sits above the rectum. The only time your rectum fills with stool is when the sigmoid colon fills up and needs to release it. Through a combination of anatomical structure, neural switches and reflex triggers it is impossible for stool to remain in your rectum. Now, often there is residue, for sure, and we’ll talk about that later in the chapter. But for now, know that your rectum, the place that will lovingly hold and pet the penis when you’re bottoming, is a pipeline, not a storage device. It is the Panama Canal between the sigmoid colon and your sphincter. Ships can only pass through; they cannot anchor.

The sigmoid colon releases waste (stool) to the rectum when the body is ready for elimination and only when it is ready. There are several ways the body makes sure that things don’t ‘slip’ into the rectum accidentally. First, the juncture between the sigmoid colon and the rectum lies at ninety degrees. The sigmoid colon is horizontal where it meets the rectum, which lies on a more vertical plane. This sharp angle stops feces from entering the rectum on their own. “Security” is reinforced by a sphincter muscle between the sigmoid and the rectum (Christ, how many sphincters do we have in our bodies!). In its natural state this sphincter is constricted and thus acts as the gatekeeper. It remains tightly shut unless it receives a command from headquarters.

As fecal content grows in the sigmoid colon it exerts pressure on this sphincter muscle. This triggers one of many involuntary “defecation reflexes” and signals the sigmoid sphincter to open up and let the fecal content into the rectum. The entry of feces into the rectum distends the rectal wall. There, stretch receptors trigger signals to the descending and sigmoid colon to increase peristalsis (the involuntary constriction and relaxation of the muscles, creating wavelike movements that push the fecal contents forward). These “waves” of movement pass through all the way to the anus, causing the puborectal sling to loosen, straightening the S curve in your rectum, and causing the internal sphincter (remember him, the one who doesn’t obey your orders to relax?) to completely relax (the bastard!).

But defecation only happens once you release the external sphincter, which you have conscious control of. When you can’t find a bathroom (and you’d rather not relieve yourself on the carpet) you can clench your external sphincter to keep it from happening. You will also be aided by the sling, which acts as “continence muscle” that stops you from farting or taking a shit in the middle of a cocktail party. When you need to go but can’t, the sling responds to the pressure by contracting, which holds the feces back until you have the opportunity to find a bathroom.

Nice, huh?

Read more…

How To Be A Better Bottom

Medical experts agree: Enemas are harmful. Pushing water or a mixture of water and chemicals up your bum creates a powerful peristalsis (accompanied by bloating and cramping) that “evacuates” everything in your lower intestinal tract. Medically, enemas are most commonly used to bring on bowel evacuation as a way of cleaning you out for a colonoscopy (an examination of the bowels with a fiber-optic camera). You can buy these kinds of enemas at drug stores (Fleet is the most popular brand. I love the name. It’s like the manufacturer bought a fleet of vehicles that drive the stool through the Holland Tunnel).

Do enemas work? Yes, you’ll never be cleaner in there (or up there, as the case may be). Should you do it? Absolutely not. Never, ever put chemicals up your butt without medical supervision. Even “harmless” chemicals like mild hand soap, baking soda or sodium phosphate can irritate the colon, cause cramping, and draw electrolytes from the body. But these dangers are entirely beside the point. If your rectum is so dirty that you have to hose it out, the answer isn’t a fire hydrant connection; it’s a better diet.

Introducing The Best Way To Get Yourself Clean.
If enemas and douches pose too great a risk (and embarrassment) for frequent use, then how can you get yourself 100% clean? I’d like to introduce you to a device that will flush out fecal residue without the dangers of an enema or a douche:

Read More…

Gay Anal Sex Tips

Congratulations! You’re ready to bottom without pain or stains!

There’s just one thing. And that’s this notion you have that your partner should take charge. Most guys fantasize about bottoming with men who initiate, direct and control the encounter. They think their role is to simply respond, yield and surrender. There is nothing wrong with this notion—it’s hot, actually. It’s just not very realistic the first few times you experiment with bottoming. Here’s why: pain-free bottoming requires you to find the best position to straighten out your S curve, estimate the best angle of entry and control the pace of Sexhalation. How are you going to do that if you relinquish control?

In addition to not knowing a single thing about the way you’re built or how Sexhalation works, your partner is dealing with his own issues. Can he stay hard enough as he deals with a condom? (A must if you’re not in a monogamous relationship). Can he find your anal opening in the dark? (It’s harder than you think. Tip for tops: place a fingertip on it and use it as a guide). Will he feel pressured if he’s saddled with total responsibility for the success of your session? Are you going to judge him if he doesn’t know exactly what to do?

This is not a good dynamic for your first few bottoming sessions. You signed up for pleasure, not pain. The only way you’re going to avoid pain and experience pleasure is to control the way your partner’s penis goes in and out of you. And in and out. And did I mention in and out? I know that taking control might seem a bit of an irony—isn’t bottoming about surrendering yourself to another man? How can you surrender when you’re in control? Isn’t that an oxymoron, like “jumbo shrimp” or “pretty ugly?” Not to get all Zen up on your grill, but “controlling your surrender” is one of those contradictions that defy explanation. It cannot be explained but it can be experienced, as you’re about to find out.

Read more…

Tips For Gay Sex

Adam and Steve have been dating a few months. Adam likes bottoming for Steve but he also wants to top him. They tried a couple of times but Steve was just so tight down there that they couldn’t complete the act. It wasn’t that Steve didn’t want to bottom for Adam, it’s just that the pain was so sharp he simply stopped trying. Finally they bought this book and decided to give it a try. Steve was determined not to repeat the painful experiences he had with bottoming in the past. He knew he couldn’t just jump into bed and hope for the best, so he took note of the first part of this book: Prepare. Here’s how he started:

Two Weeks Before Steve’s First Attempt At Bottoming.

He mentally signs his “No Pain” contract. No pain, no way, no how, at no time. This is an enormous burden off his shoulders (and his rectum!). He can now go from someone paralyzed with “anticipatory pain” to somebody who looked forward to “anticipatory pleasure.”

Read More…

How To Be A Bottom

Should I use poppers? What about Anal-eze or other pain-masking substances? Will I end up wearing diapers if I bottom for hung guys? Does bottoming cause hemorrhoids? Why can’t he cum when I bottom for him?

These and dozens of other questions are answered in full detail. Stay tuned!

Read More…


What Are Guys Saying?


how to be a bottom

Simply the most informative, insightful, and funniest sex book I have ever read. This book taught me more in one day about gay sex then my 55 years on this planet has taught me. Doesn’t matter if you are just a top only kind of guy, you learn a lot from about self image, drugs, and sex by reading this book. Does gay sex hurt? Not if you read this. I highly recommend this book.

Sam, 43

The book is written with knowledge, clearness and in a very funny but responsible and up to date way, including techniques that every man willing to bottom (and even those who prefer to top) should know. If you want to learn how to be a great bottom this is your ticket.

David, 28

Loved the book! It was an easy but informative read. I learnt a lot , and can now approach the subject of being a bottom with pride, knowing what to do, and when, and filling in the gaps. I feel eager to get out there and practice, and with the new hints and techniques look forward to being a better lover. At first, the title put me off cuz I’m more into romantic gay sex, but it was perfect.

Eric, 32

Oh, the joy of gay sex. Woody is not afraid to step on toes and I love that. The Real Truth! I truly appreciated it! And yes, this works! I used to have so much pain when I bottom and now, NOTHING. Saved my sex life!

Mike, 48

This book has given much insight on why I always have a tough time having gay anal sex. With his methods and new understanding of how the body works I am now having painless and stainless sex!

Robert, 25

The author made learning about bottoming FUN. The description of the S curve (talk about gay sex terms!) and how to get past it were the best I have read. He is spot on about fiber. A thorough and practical guide.

Caleb, 52

I learned things which I had no clue about, and after giving that new information a try I was simply amazed to be honest as it took play to a whole new level, and I have found this is the best book on gay male anal play I’ve ever read.

Nick, 43

An excellent guide for gay men who want to learn to bottom the right way. If you’re new to bottoming and/or you have fears or even if you’re experienced I totally endorse this book. I read it in a few hours. I didn’t want to put it down!

Manny, 22

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Bottom Like A Porn Star

Expand your sexual vistas by being more versatile. This book will show you how to bottom without pain or stains. There’s a reason it’s been the #1 selling gay sex book for the last two years. It’s a step-by-step guide to bottoming–complete with a major section on how to get yourself spotlessly clean. Also gives you keen insight into the porn industry–how they do the deed and how you can too!

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TOP Like A Stud

Learn how to be the guy everybody wants to get under! From discovering your inner top to learning how to completely relax your partner’s sphincter for a pain-free experience, this is the only gay sex guide strictly devoted to tops! It answers all the gay sex questions from a top’s perspective. Find out the which thrusting patterns and techniques will double your pleasure. And his.

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Whether you’re alone or with a partner there’s something really impressive about shooting your load rather than having it dribble out. That’s why I teamed up with a urologist to bring you a master class in not only how to cum more but how to cum further. Ejaculate up to 1-2 feet further and increase your semen volume up to 25%. Add excitement and impress your sexual partners.


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