13 Reasons Why/Tape 3: When An Experiment Fails

When I’m with a man . . . when I’m inside a man . . . I’ll often tell him he’s beautiful. I don’t have to praise anyone’s looks to flatter my way into his pants. With a single photograph, usually the size and proportions of my dick do all that work for me. I don’t tell a sex partner he’s handsome to fluff his ego. In fact, I won’t tell him he’s good looking if he’s not.

No, when I tell a man he’s beautiful, it’s solely because he deserves the praise. It’s because he’s opened up for me—legs, hole, and soul—and put himself into a vulnerable position. When men are at their most vulnerable, they’ll believe truths about themselves they might not otherwise.

But this story is not so much about fucking, as it is about a friendship. Hamilton, welcome to your tape.

A long time ago I had sex with a man in a Manhattan hotel room.

Okay. I know, given the number of men I’ve fucked in Manhattan hotel rooms, that my opening sentence doesn’t exactly narrow anything down. But this guy was different. We had—I thought, for a while—a connection.

His name was Hamilton, and his photos were deceptive. I don’t mean those words in their shadiest sense. That is, he didn’t post photos of an Adonis and show up looking like a slightly less comely Wallace Shawn. The pictures he unlocked for me on Manhunt were sexy as hell, admittedly, featuring a lightly muscled, narrow-waisted body decked in a leather harness, and an impressive and rigid cock jutting out with menace from a pair of slick black chaps. All the photos had been taken, it looked like, lit solely by the red glow from a police car light. The effect was devilish.

He listed himself as a top, but he wanted an experienced man like myself to show him the pleasures of his hole. I was only too glad to oblige.

When I met him for our afternoon together, I was greeted at the hotel door not by the sex demon I expected, but by a perfectly respectable man dressed in a natty tweed suit and tie, beaming from ear to ear finally to see me. He was a good-looking guy, absolutely, but for a short time that afternoon, the dissonance between the sexy little clean-cut man who looked like the host of an HGTV decorating show, and the raging Prince of Lust from the Manhunt profile, was difficult to reconcile.

Until I got his clothes off, that is, and buried my dick deep into his tight, hairy hole. That’s when the spark ignited in his eyes, and the flames between us flickered white hot. I banged him three times on the mattress of that four-star hotel, holding him down while I talked about how pretty he was, and how hot his hole felt, what a pleasure it was to fuck a hot boy like him, and how I was going to paint his guts with my seed.

A bucket of sweat and cum later, he surprised me by climbing on top of me, flipping me over, and spitting in his hand and spreading it over his dick. “You want my cock, faggot?” he growled in my ear.

Yes, sir. Yes, I did.

That fuck was primal. I melted, looking into that handsome face as he drove into me again and again. That’s when I realized those Manhunt photos weren’t deceptive at all. Hamilton might’ve dressed in a particularly dapper way when I met him, but behind closed doors, he unleashed a beast that got what it wanted. Anything it wanted.

Afterward, we lay on top of the bed, still and quiet, covered with rivulets and exhausted, seemingly worn out. “You are a hell of a good bottom,” he wheezed, trying to catch his breath.

Maybe it had been true in that moment. Maybe, after torturing myself for years over my inability to enjoy taking dick in my ass, it was a truth I needed to hear after I’d opened my hole and exposed my vulnerable underbelly. Either way, it made my dick stir into hardness once again.

“No, no, I think I’m worn out,” he protested with a laugh when I positioned myself over him on the bed, one palm flat against the mattress to either side of his shoulders. He chuckled weakly when first one knee, then the other, pried apart his legs. Then, when my rigid dick probed his dripping pussy, he moaned a little, and allowed me to slide inside.

I looked in the face of Hamilton, that satyr, that man of many facets, and parted his hole with my dick until it hit the base. My own seed squished around my rod in its slippery home. “You are fucking beautiful,” I told him. He shook his head, nay-saying the compliment. “You don’t know how attractive and sexy you are, do you?”

At his shy non-response, I shook my own head and began picking up the pace with my thrusts. His body responded as it had before, with hunger. He might have thought he was done, but his hole now told him differently.

“You are incredibly good to look at, Hamilton,” I whispered to him. “You truly are beautiful.”

His lips parted with a small sigh of contentment. Happiness, even. “You make me feel beautiful.”

“Because you are.”

“But you make me feel it,” he said, smiling.

“You need to give yourself permission to feel it more often,” I suggested. Then, with my hands cupped around his sweet face, I pounded another load into him.

We met again a couple of months later when he was again in the city. For the first part of the excursion, we spent several hours in bookstores, talking and catching up. In the interim we’d established a friendship via email. We’d talk about the holes we’d fucked—you know, the way we do in the rarified enclosure of The Tops’ Lounge—and reminisce about the afternoon we’d shared. We exchanged dozens of emails about reading and art, and about writing and our own feelings of being oddballs in the sexual culture.

I’d even come out to him about my blog, and asked permission to write about our encounter together. He’d granted it—and when my post about him came out, he was furiously shy about his appreciation.

When it comes to afternoons out, I can’t think of one that was more delightful. Even now, when I think about it, it’s cast in a rosy glow—giving each other books to look at, laughing about topics dear to my heart in which none of my other friends have any interest, discussing the difficulties of writing. Several times during the afternoon, I noticed other men cruising Hamilton as we walked toward them. I’d nudge him. “That guy is totally into you,” I’d say.

“No,” he’d laugh. “Absolutely not. He’s out of my league.”

“Bullshit! He’s checking you out! Look!”

Hamilton would at last raise his eyes and briefly meet those of the man giving him the once-over. Then he’d blush like a schoolgirl. “Well, fuck,” he’d mumble.

“It’s because you’re totally hot,” I told him.

“I’m not. Seriously. I’m the scrawny little ninety-eight-pound weakling who the hot guys hate. They’re only looking because—well. . . .”

“You’ve got this notion of yourself in your head that’s totally at odds with the reality of you,” I said.
“You’re getting all this feedback from the real world that should be telling you I’m hot! I’m hot! But you keep repeating to yourself, I’m not, I’m not.”

“I’m not hot,” he mumbled. Then, as concession, “But you make me feel like I am.” It was an echo of the afternoon we’d shared.

I also echoed back to that afternoon. “Give yourself permission to feel it more often.”

We returned to his hotel shortly thereafter, stripped down, and repeated our first session—although I did all the topping. The entire time I kept telling him, you are beautiful, you are beautiful. I fucked like I was trying to pound the message home—or at least silence that inner critic who kept telling him otherwise.

It was afterward, when we were panting and sweaty once more, that he looked me in the eyes and said, “I never think of myself as attractive. But you make me feel like an entirely different person.”

“So why don’t you allow yourself to be?” I asked him quietly. “Let yourself be an entirely different person. Do it as an experiment. Just for a day. Try it on and see how you like it.”

He nodded, and I let the subject drop.

I’ve written about this incident before. I received a letter from him not long after in which he confessed that the question I’d asked—so why don’t you allow yourself to be?—resonated with him so much that the very next day he gave himself the assignment of getting through the day, assuming he was sexy, and hot, and handsome, and attractive.

So he looked at himself in the mirror, and liked what he saw there. He went out into the streets, and for the first time noticed men and women admiring him. He flirted with a barista and got a cookie. He kept repeating the experiment, day after day, and found his confidence growing.

It was one of the few times in my blogging career, honestly, that I felt I’d made a concrete difference. Oh, I have readers write to me and tell me I’ve changed their lives, and it makes me so happy to hear those words. It genuinely does. But I don’t personally, in the flesh, know any of the fine men who make these assurances.

I knew Hamilton. We were friends. He was one of my rare friends who didn’t make a big deal about my blog, or treat me any differently because of it. Knowing I’d helped him a little, as a friend . . . well, it was everything to me at the time.

The problem was, subsequently, that as Hamilton’s confidence grew, the less he seemed to need me as a confidante. We continued to exchange emails for a time, but while mine were full of chat about books and sex and theater and sex, his grew more and more terse. Just got your email!, he’d reply to me. I’ll send one back after I finish this lecture I’m preparing. When I didn’t get anything, I waited a week or two, then sent another. I owe you an email!, he responded. I’ll be doing it this weekend!

After the third reply in which he told me he would write back to me as soon as possible, I conceded defeat. I got the message. I stopped writing. I commented only rarely on his many Facebook posts, knowing that my contributions there were being drowned out in the flood of chatter from his thousands (yes, thousands) of social media followers.

Hamilton would come to town. I’d hope for another invitation to meet him—if not in his hotel room, at least at a bookstore, or for lunch or coffee. The invitations never came. Again, I got the message.

Friendships wax and wane, I sadly know. I try not to take friends for granted, because I know that they’re just as likely to vanish without warning as they are to arrive unheralded. Friendships are meant to be enjoyed while they persist, and to be remembered with fondness later if they’d been cultivated well. Maybe, I told myself, Hamilton’s friendship was only supposed to last for as long as it took for me to deliver that one message from the universe: You are beautiful. Why don’t you allow yourself to be?

It was small solace, that thought. But it helped me let go. I clung to it for a while, as I seemed to become more and more invisible to my former friend.

What consolation I derived, however, was short-lived. Hamilton’s self-dislike began to creep back onto his social media postings. One day he’d post a screed about being the ugly guy being pushed around by the muscle gods of the gym. He’d follow it up a couple of weeks later about feeling freakish and ugly around groups of gay men. Last year, he wrote a couple of Facebook posts that revealed such depths of fury toward his self-image that for weeks after I had to let my eyes skip over anything he subsequently had to say.

That experiment I’d proposed had obviously failed.

Again, as I’d had to do with the friendship that Hamilton and I had once shared, I forced myself to concede defeat. Letting go for the second time, though, hurt. I thought I’d made a difference. I hadn’t. Not a lasting one, at least. If I couldn’t contribute lastingly to someone I’d once considered a close, dear friend, how the hell could anything I said, anything I wrote, make a difference with a total stranger? A blog reader?

This Faggot, from my previous entry, had claimed I’d changed him. It’s how he approached me. My words, he told me, had made a concrete difference in the day-to-day quality of his life. But in the end, was I able to change him enough to get his dick out of his hand long enough actually to meet me? Nope. Was my writing, my ethic, enough to convince him to act toward me with the same good faith to which I’d extended him? Not in the least. If that’s the kind of change I’m making in readers—no thanks.

At a low point in my life, I was forced to confront the fact that perhaps, despite what men told me, my words, my advice, the very things I believed about sex and love and life, meant absolutely nothing. Nothing I had ever done had felt so futile. Why write at all? Why create?

Self-image issues often run deep. They can’t be erased by a simple encomium or a quick platitude. Years of hearing how ugly one is from other people leads to even more years of one telling oneself the same falsehoods, until the pattern is so deeply engrained it feels impossible to fight against. I know all these things. I’ve struggled with them, myself. I still do. Daily. But sometimes I can get through a day in which I allow myself to be foxy as hell, to all and sundry. Sometimes I can make it two days. A week. I give myself that permission.

There’s nothing that I can say that will repair anyone. I know this, too. Every man gets to haul out the self-help toolbox and treat himself as a fixer-upper. It’s the individual’s responsibility to look in the mirror, daily, and say, Today’s the day I’m allowing myself to be all the good thing things I wish for.

Every time I climb into bed with a good-looking man and I tell him how beautiful he is, I’m going to wonder if he really hears the message I’m trying to tell him. Judging by my spotty track record, I’m going to guess not.

But I’m going to keep on saying the words, anyway. And I’m going to hope that some day, someone will listen, and believe me.

Afterword

During my hiatus, I’ve received from readers a lot of very sweet emails wishing me well. Most of them have recognized the amount of work I’ve poured into my blog and have expressed their thanks. I’m so grateful for those sentiments.

Many people who’ve written, however, have made the assumption that the reason I have decided to take a break is because of the so-called haters—that is, the men who leave nasty comments on my blog, and those who go out of their way to make sure I understand how contemptible I am to them.

I’ve had plenty of haters over the years. They wear me down, yes. But more than anyone, the men who have sucked the joy out of my writing (and to a certain extent, my life) are those who meant well. They’re men who claimed to admire me, who wanted to meet me—and many of them did—and who then, whether out of clumsiness or fear or whatever, failed to recognize they’d gone too far. A man can only withstand so many successive blows to the ego (even an ego as Jericho-sturdy as mine) before it begins to tumble.

What’s more, every single one of these men read my blog. They’re men who subscribed to my point of view, who enjoyed my writing. Or read my writing, at least. Some of them wanted to be written about. Others never intended me to know they were blog fans.

Maybe one of these men is you.

If it is you? Although there’s a small and petty part of me that wants to flip a finger in your direction, I’m not going to. I’m moving on as I write this series. A friend of mine shared with me something his grandmother used to say that I truly believe: People do the best they can. If they could do better, they would.

My advice, if you think you recognize yourself . . . or even if you don’t: do better.

All of us could stand to do better.