How To Bottom Like A Champ
A Guided Tour of A Gay Anal Sex Session
“Adam and Steve” first contacted me through social media. Would I be willing to coach them through a successful session of anal sex? After dating a few months, Steve wanted to bottom for Adam but they gave up after several painful attempts. Then they decided to use this book as their guide—and asked me to augment it with coaching.
They set a date for what Steve called their “Blastoff” (the day they’d attempt intercourse) and got to work. What follows is a description of their experience, with me adding background and comments.
Three Weeks Before Adam & Steve’s Blastoff
Action: Sign a “No Pain” contract.
Steve admitted he was paralyzed with “anticipatory pain” and understood he had to guarantee himself a pain-free experience. He signed a No Pain contract and adopted my motto: No Pain, No Way, No How.
“At first, I felt like an idiot signing the contract in the book. I just thought it was a cheesy attempt to make a point, but I have to admit I felt an enormous burden off my shoulders…and my ass! I came to see the signed contract as a promise to myself. Complying with the contractual terms was really about keeping my word and I felt at the very least I owed myself that.
Also, I was determined not to pay the author a dime for breaking the contract!”
Action: Take Fiber Supplements
Steve increased his fiber intake through diet, but it didn’t seem to help (his butt was dirtier than he felt comfortable with) so he decided to take supplements.
“It worked! After about a week I saw a significant improvement in my cleanliness down there. I’m about to be the champ of how to be a great bottom!”
Action: Do Kegel Exercises
Kegel exercises are not strictly necessary for painless bottoming but I told Steve strengthening the musculature of the entire puborectal region will significantly accelerate his progress.
“I did them religiously like twice a day. One thing I noticed after a couple of weeks is that I was cumming more and shooting farther so that was a great bonus.”
Action: Inserting Fingers Correctly
This is where Steve does all the exercises in Chapter Four. He learns how to relax his sphincter onto his finger (rather than inserting his finger into his anus).
“At first, I could barely draw in 1/8 of an inch of my finger, but I didn’t get frustrated because I knew this was a marathon not a sprint. At least the 1/8 of an inch went in without pain!
I was fascinated by the difference between a) inserting my finger into my ass and b) letting my sphincter relax onto it. It wasn’t long before I could get my whole finger in there with no problem.”
Two Weeks Before Adam & Steve’s Blastoff
Action: Continues Fiber Supplements
Action: Continues Kegels
Action: Insert A Butt Plug Correctly
What’s the secret to being a good bottom? Sex Toys! Steve replaces his finger with a sex toy. While most guys only need to buy a toy around five inches in length (the average size of a man’s penis), Steve’s partner, Adam, is bigger than average so he buys one closer to his size.
“I kept to the letter of my No Pain contract—I inserted the sex toy slowly and if I got even a hint of pain I backed off. Also, I’m cheap and I didn’t want to Venmo the author $9.99 every time I squealed like a schoolgirl. It was slow progress but painless progress.
Whenever I inserted the sex toy further I made a conscious distinction between pain and unfamiliarity. If the sensation was more like pain I backed off. If the sensation was just unfamiliar, I stayed where I was, waited for the unfamiliar to become familiar and moved on.
It took about 10 days of daily practice but I was able draw in the sex toy completely. I was flooded with hope because that toy was about the size of Adam’s dick and it didn’t hurt to have the whole thing in my butt. I was so ready for the real thing!”
One Week Before Adam & Steve’s Bottoming Blastoff
Action: The :60 Sphincter Release
This is where Steve squinches his sphincter as tight as he can for as long as he can until his internal and external sphincter muscles go into failure and he is helpless to prevent them from relaxing.
“Before Kegels, I could squeeze my sphincter for about 45 seconds before they gave out. But after a few weeks of doing them I could hold it for 75 seconds. That’s like an increase of two thirds!
I’m glad I practiced The :60 Sphincter Release before Adam and I had intercourse because you really do have to familiarize yourself with the process. I think it would have ruined the moment if I had first tried it when Adam tried to penetrate me. I had lots of questions and had to repeat it multiple times before I got the hang of it, especially with the sex toy.
Action: Test Angles Of Entry
Steve understood that Adam’s penis should enter him at about a 45-degree angle so he practiced it with the sex toy. The point was to familiarize himself with what 45 degrees means— in different positions —so he didn’t get confused when it was time for Adam to penetrate him.
“It helped to visualize Adam’s dick–it’s shape, it’s angle when it completely hardens and how it hangs from his body. I pretended the sex toy was his dick and figured out the best angle for me, given the shape and angle of his dick.
Action: Practice Using A Butt Syringe To Clean Up
I do not recommend douching for all the reasons outlined in Chapter Ten, but Steve was insistent and used a butt syringe to clean himself out.
“The author’s words and illustrations make a powerful case against douching but I’m too OCD about butt sex not to. I will say, in my defense, that I was very careful not to squeeze the bulb too hard, lest the water get into my sigmoid colon and literally create the kind of shit storm I was trying to avoid in the first place.
My advice is that if you’re going to use a butt syringe do it the way I did—practice using it a few days before anal sex so you get the hang of it and see if unexpected things happen.”
The Day Of Adam & Steve’s Blastoff
Action: Eat Sensible Food
Steve understood that on the day he planned to bottom he shouldn’t eat what I call “McWhaaaats”—foods so dense with fat, protein and carbs they turn your insides into lava causing you to leave so many tire tracks your underwear could be NASCAR’s next logo.
“I stayed away from things I normally gravitate to—like a Triple-Decker Guacamole Bacon Thickburger and stuck to light meals like skinless chicken breast and vegetables that were easy on my stomach.”
“I didn’t want to interrupt a hot and heavy make-out session to stick an ear syringe up my ass, so I did it early in the evening, way before sex.”
Adam & Steve’s Blastoff
(Steve takes over from here without my commentary)
I Make Out With Adam
We kiss a lot, undress each other and head to the bedroom.
I Use The Author’s “Secret Sauce To Hot Sex”
As I go down on Adam, the author’s words ring in my ear: “Create anticipation, get in touch with why you want to bottom, ask yourself what it is about your partner’s dick that turns you on, etc.”
I pay careful attention to the things I’d previously taken for granted—the size, strength, and firmness of Adam’s cock and it fills me with desire for it. I tell him how I feel and I notice he got even harder!
While it’s in my mouth, I think “This beautiful cock is going to be inside me in just a few minutes. I want to be owned by it, I want to give myself up to it.”
As we kiss, I make sure Adam rolls on top and covers my entire body with his own—chest to chest, his hands and feet on my hands and feet. This gives me the feelings I crave so much—to be protected, feel secure, submit to his strength and power.
Adam picks up on this and he gently pins my hands over my head and uses his knees to separate my thighs. I get harder. He notices. “Look how hard you got!” he says. He slides his hard dick between my legs, rubbing the head of his penis softly, gently around the opening of my butt and perineum. NOTE: I made Adam read the chapter on how to create anticipation so he would know what to do. Was that cheating? Maybe, but who cares! I loved what he was doing to me.
I could feel the strength and heat of his big cock in between my legs and I could feel the anticipation building. I squeeze lube onto my hands, put them behind me in a cupped position as if they were an extension of my anus. Adam starts slowly, gently thrusting into my hands as if he were inside me.
At this point we are both in an erotic spell. First, I had Adam’s hard cock in my mouth and now I could feel its heat and its strength between my legs, thrusting into my hands. I could feel that delicious mix of smoothness and strength, velvety softness and unrelenting hardness. I was awed by its masculinity, its insistence, its aggressiveness and its desire to be inside of me.
I liked the idea of giving in to this masculine energy, to succumb to its power, to give up my boundaries, and let it take me.
I was ready.
Adam caresses my anus with lubed fingers but for some reason it actually lowered my desire. I remember the author saying I was in charge, so even though I knew Adam liked to play with my ass I asked him not to.
Actually, I didn’t ask him not to —I didn’t want to ruin the mood so I just gently moved his hand away.
I Get Ready To Be Penetrated
I decide I want to do it in the missionary position even though I know it will be easier on me if I squat over him. That’s because I want to submit to him and it just feels odd to take the power position (on top of him) to experience submissiveness. Just a personal choice.
Because I know I have to straighten my S-curve, I bring my knees as high to my chest as I can. It feels odd. Spreading my legs apart and drawing my knees in completely exposes my anus to Adam, leaving me feeling vulnerable and at risk for the possibility of real harm to occur.
My fear completely gave in to desire, however, as I realized that this feeling—of being vulnerable, of being at risk, is a hallmark of submissiveness. It’s me saying to Adam, “I’m dropping my guard, all of my defenses. I am yours. Own me. Do what you want.”
With renewed horniness, I guide the head of Adam’s penis so it’s angled about 45 degrees away from my navel. He also positions himself so that this is easier to do. With the head of Adam’s dick gently, but firmly against my anus, I tighten my sphincter as tight as I can, with the author’s words emblazoned on my mind: “Do not insert a penis into your anus, allow your anus to draw it in.”
Suddenly I realized that I hadn’t paid much attention to Adam during this whole process and I noticed something the author warned about—the possibility of a top getting softer because of the time and distractions of getting prepared.
In fact, Adam had lost some of his rigidity so I stopped The :60 Sphincter Release midway, put some lube in my hands and showed Adam’s dick (and his balls—never forget the balls!—some love). Once he got completely hard I restarted the release process.
Some advice: I found it was actually better to start the process of tightening my sphincter before I positioned Adam’s erection firmly against my anus. Sixty seconds is a lot of time for your partner to be on top of you simply waiting for a signal that you’re ready. It’s a recipe for him to get softer.
So what I found more effective is to play with Adam’s dick (and balls, never forget the balls!) until about :15 before I know my sphincter is going to involuntarily release.
As my sphincter completely and helplessly relaxed, I could feel my butt drawing in Adam’s dick! But it felt too slow and I was afraid it was going to pop out so I cheated and guided it in with my hands s-l-o-w-l-y.
I Get Penetrated
It worked! He was totally in and it didn’t hurt! Now, I do have to say that while it didn’t hurt it felt like the slightest move would bring on a LOT of pain. That’s when I remembered the author’s words—“Don’t proceed until unfamiliar and uncomfortable sensations become familiar and comfortable.”
So I asked Adam to stay still for a few moments. It wasn’t long before the sensations lessened. Later, I realized that my puborectal region was adapting itself to the presence of Adam’s dick.
Even when I gave Adam the signal to start moving inside me I made sure he went at the speed of a turtle. I remember the author saying that no matter how relaxed the sphincter, no matter how much you straighten the S-curve, the puborectal muscles naturally contract when an object is inserted into the rectum.
I Make Small Adjustments
I moved a little to the right and asked Adam to straighten up a little because I could sense things were going to hurt if I didn’t. If this book has taught me anything it’s that you have to be aware of what your body is saying to you and obey its limitations.
On My Own Erection
At this point, I realized my hard-on was gone! I was like, WTF! Later, when I emailed the author I found out a lot of guys lose their hard-ons (and then get it back later). Apparently, the “sensory overload” of being penetrated can divert attention from your own erection. It kind of makes sense, as I’ve often noticed that sometimes my boner goes soft when I’m blowing Adam even though I’m really turned on.
The author also wrote that it may even be a good idea not to stimulate myself in the beginning, as arousal can cause the sphincter muscles to tighten up a little and make penetration a tad more difficult.
On Feeling Like I Had To Take A Dump
Once Adam was fully inside me I had this weird feeling like I wanted to defecate. The feeling went away but it alarmed me for obvious reasons. In a later email, the author wrote, “Don’t get alarmed. The rectum has “stretch sensors” that activate the elimination reflex. The body senses the rectum is full so it thinks it has to relieve itself. But in actuality, there is no stool in the rectum and within just a few seconds, the feeling of wanting to go to the bathroom will recede.”
On Feeling Like I Had To Pee
I also had a vague urge to pee, which alarmed me to no end. But as the author emailed me, “Feeling like you have to pee is fairly common for the receptive partner when he’s on his back. That’s because the bladder rests directly on the rectum. As Adam’s penis pushed into you, the rectum prodded your bladder, making you think you needed to urinate. The feeling goes away once it’s reinterpreted correctly.”
On Being In Charge
I have to admit I hated the chapter on “being in charge.” It didn’t make sense that the bottom should be in control, but upon reflection, I think the author was absolutely right. There were so many times pleasure headed towards pain and if I weren’t in control I would have shattered my No Pain contract like a brick through a windshield.
Here’s a perfect example: I asked Adam to pump faster and I loved it…until I didn’t. But Adam had no idea the fast pumping was headed towards pain. How could I possibly expect him to know what was happening in my body?
I’m glad I stuck to the author’s advice: CONTROL EVERYTHING. After a while, I let Adam take over more and more because he understood what was likely to hurt me.
Couple More Thoughts
On My Orgasm
I was amazed at how far I shot and how much cum came out. The author’s email: “This isn’t unusual because the prostate is responsible for the production of ejaculate. The more stimulated the prostate gets, the more semen it will produce, and the more forcefully it will be expelled.”
On Post-Orgasm Activity
I wanted Adam to pull out immediately after I climaxed. That wasn’t addressed in the book so I was startled by the discomfort. The author’s take: “Men typically want all sexual activity to stop after they ejaculate and bottoming is no different. Sexual stimulation simply doesn’t feel good once the refractory period sets in.”
On Our New Sex Life
Adam and I are incredibly happy as we see new sexual horizons open up. Adam feels like he now has a fuller experience of me and I feel like I know Adam in a completely different way. We feel closer to each other than we’ve ever been, and I think it comes from trading vulnerabilities, being sensitive to each other’s needs, and honoring each other’s requests.
HAMMERING IN A FEW CONCLUSIONS
Do you know why Steve’s first bottoming experience was so successful? He took control. Your success will depend on your willingness to take charge and clearly communicate what you need. Only you know what you need and if you don’t, you’re the only one who can find out.
The experience of bottoming is different for everyone. Some guys literally come within thirty seconds of being penetrated. Others can’t get hard, even when they’re enjoying it.
Some guys love missionary because they like the body heat and the feeling of submission that comes from being on the bottom. Others find it suffocating and prefer less confining positions.
Some guys like slow, deep thrusts, others like shallow, jackhammer thrusts. Everybody is different. Find out what you like, not what you’re supposed to like.
It may take you longer to prepare yourself for bottoming than it took Steve. The tightness of your sphincter, the shape, and elasticity of your rectum, and the shape, location, and severity of your S-curve will determine how long it will take to train your puborectal region to accept a hard penis.
Do not despair if it takes you longer than you had anticipated. It doesn’t mean you’ve failed; it means your puborectal region is built in a way that requires more training. This isn’t a race. Don’t let impatience rob you of a lifetime of great bottoming experiences.
A Few Last Tips
Use A Pillow Or Two Under Your Butt
It’ll change the angle, ease the strain on your lower back and make you more comfortable.
Try To Avoid Doggie Style At First
This position allows the maximum insertion of the penis into the rectum, which may be uncomfortable the first few times you bottom.
Any time air gets pushed into a small, enclosed area, it’s highly likely to create an unwanted sound. Don’t worry about it. If it happens, the only appropriate response is laughter.
A Penultimate Thought
Anal intercourse stimulates three areas: The prostate (“the male g-spot”), the nerve endings in the opening of the anus (the rectum itself has few nerve endings. It primarily transmits sensations of pressure.), and the “penile bulb” located at the base of the penis, just below the surface of the perineum.
Guys have different reactions to having these areas stimulated. Some, like Steve, have astonishingly pleasurable reactions, while others shrug it off with an “is-that-all-there-is?” dismissiveness.
Still, others simply don’t like any of the sensations. Where you fall in the spectrum of reactions is strictly a personal preference that you should not judge. Don’t feel like there’s something wrong with you if you didn’t experience the earth move under your feet. Lots of guys try pain-free bottoming and don’t like it.
Still, I’d like you to consider a core philosophy I have about sex: Never try anything once. Try it three times. The first time you’ll get it wrong. The second time will be awkward. The third time you’ll fully experience it.
If you were underwhelmed with your first time bottoming, don’t worry about it. You’ve got two more times to go!
A Last Thought
Once during filming of The Sex Inspectors, a sex makeover show I co-hosted a few years back, I sat on the bed with a woman I was advising. Don’t worry, we were fully clothed. Not that anything would have happened. If you haven’t figured it out by now, I’m gayer than a box of birds. I know the difference between beige, ecru, cream, off-white, and eggshell.
The video cameras that we put throughout her house showed how cruelly she rejected her husband’s advances. I said, “Put your arm around me, I want to show you how you reject your husband.” I whacked her arm away like it was an unwanted fly and looked away from her. Indignantly, she said, “I do NOT do that!” I said, “Yes, you do.” She knew I was right. I could see her face softening. I leaned in. “Can I tell you a secret?” She nodded. I cupped my hand around her ear and whispered something. She started bawling.
The producer, director, and audio people went nuts because the microphone didn’t pick up what I said. The director stopped the filming to give the woman time to compose, took me aside, and said, “What the hell did you say to make her cry like that?
I said, “Men have feelings, too.”
I love giving advice to people. I love to see barriers crack and humanity come to the surface. I hope I’ve been able to do that for you. May your sex life be forever hot, wet, and sticky.