The Itch

This entry will take more courage to write than most.

I’ve always been open about the fact that I was pretty much exclusively a bottom boy when I first started having sex with men. I stayed that way until the day I was twenty-one or twenty-two and I hooked up with a florist who took me in the back room of his workplace, stripped down to his skin, hopped up on one of the metal worktables, lubed up my dick, and guided me into him. The feeling of his ass around my cock was so electric, and my orgasm was so fast and amazingly strong, that I was hooked on topping after that, and rarely looked back.

I attribute my years as a bottom to making me a better top. Once in a while, though, the old itch returns. The following is difficult for me to admit for a number of reasons, but I fantasize about bottoming more than I really care to admit. The last time I was successfully topped, though, was about six or seven years ago. It’s been a while.

Last May the itch got too much for me to handle. I wanted it scratched, and badly. After mustering up the courage (which took a few days), I wrote a Craiglist ad that read:

Let me be blunt. I've been pretty much exclusively top since my early twenties. Since then I've bottomed for three, maybe four guys, and liked it only with one. I'm looking for a versatile man or another top who's willing to take his time and be real gentle about opening me up and helping me want it. I'm nervous as hell even asking for some butt play.

The stats: I'm forty-five, taller than average, more hung than average, 160#, bearded, good looking. I'm open to all ages and races. Only responses with photos will get mine.

I got only three responses. One was from a guy I knew socially and disliked, and who did not impress me by sending a photo that was ten years and a hundred pounds out of date. Another was from a former playmate that I didn’t want to see again. The third, however, really caught my eye.

I'm discreet, 48, 5'11", 160, 34w, 42c, br/blu, trim bearded, in great shape - swim & work out daily, well hung with 8"ct, shaved, clean, DDF, I'd would love to be the man to flip you.  I have the understanding, patience and experience.  The appeal of flipping a top is really growing on me as an exciting first experience. I can't send pictures through CL, but will send face pic for yours when you reply. 

We swapped photos. The guy was handsome. I mean, really handsome. He seemed to appreciate all the same foreplay I enjoyed. His lean good looks were really appealing. What hooked me, though, is that when I asked about a quirk in his email address, he responded with a thoughtful multi-paragraph reply about Native American tribal totems and their importance to him. It was that mixture of smarts and piggishness that appealed to me the most.

I told him upfront in my email my sad limitations—that although I enjoy anal attention, I honestly have extreme difficulties asking for it when I’m with another guy. He’d know that I was enjoying it when it happened, certainly. Would he ever. But I told him I was essentially asking him in advance, while I could still do it comfortably, to take charge, set the pace, and get me to the point where he could fuck me. He was fine with that.

It was only two days after I placed the ad that we met. Neither of us had any surprises from outdated photos. I found him astonishingly attractive, and he seemed very into me as he maneuvered me into the bedroom and onto the mattress. He knew how to take charge nicely, I had to admit. He loosened me up with a lot of passionate making out interspersed with talk about how attractive he found me. Piece by piece he removed my clothing, refusing to let me help.

When we were both naked, he turned me over and raked his beard over my neck and back while he breathed warm air on my skin, all to make me gasp and shiver. My butt quivered when he gave more of the same treatment to it—and then he used his hands to separate my cheeks and bury his face between them. I was in absolute bliss for the half-hour or more he rimmed away. The guy was spoiling me, to be honest; I wanted it to last forever.

When I was wet and wanting, he used lube and spit and eased his thumb up my hole. I gasped and clutched the pillows, but it felt good. I needed it. The prostate massage he began to give me had me quaking. “Do you like it?” I remember him asking me.

The question unloosed my lips. “Oh god, oh god, oh god,” I remember saying over and over again. I couldn’t stop. For several long moments while he eased in and out, just playing with my chute with his fingers, I repeated the two words over and over, almost as if I was praying. Just as I always do, however, when I’m enjoying anal play, I started to feel guilty about it. I know it makes no sense, and I know it’s something I need to stop doing. I’m aware of my issues; I just have a problem overcoming them in the heat of the moment. My “oh gods” changed and became a soft and whispered stream of, “I’m sorry, I’m sorry. I’m sorry.” I’m not even sure I was aware of it.

“What’s the matter?” he asked, noticing the change after a moment or two. He left his thumb in my hole, but moved up so that his mouth was closer to my ear. I could feel his cock rigid against my back. “Am I hurting you?”

“No,” I said, breathless. “You’re not hurting me.”

For a minute I thought he didn’t believe me, because he stayed so still. Then he said, “You were raped.” The way he phrased the words wasn’t really as a question, so I didn’t really feel the requirement to answer. “As an adult?” That was a question. I raised my head once, then lowered it in as close to a nod as I cared to get. “Fuck,” he said. “I’m so sorry, baby.”

“Please don’t be,” I managed to say. It was really too complex a topic to address right then, with both of us hard and naked and his left thumb jabbed up my hole. There are parts of my history I’ve made peace with, and that’s one of them. It’s just unfortunate that one of the lasting side effects has been a certain muteness and a lot of apprehension, in the heat of the moment. But afterward he changed. I don’t know if I was damaged goods to him (I certainly don’t think of myself that way), or the unicorn in a glass menagerie (I’m not), or whether he worried about what his drooling dick wanted to do reflected badly on himself (it shouldn’t have).

He played with my ass a little more, and we made out and enjoyed each other, but then we ended up doing what’s happened every other goddamned time I’ve gotten up the nerve to bottom and sought out a top to do it—he talked about what a big dick I had, sucked it, and talked me into fucking him. Twice.

Which, you know. Doesn’t take a lot of talking, admittedly.

When he left, I wanted to kick myself for putting my ass in the air for a hell of a nice guy who was hot to top me, but astute and attuned enough to be insightful. I should’ve stuck with a dumb brute who just wanted to fuck, though intellectually I know that would’ve had me yelping and diving beneath the bedsheets faster than a virgin facing a boatload of pillaging Vikings.

I have my issues. We all do. I try to be honest about mine when I can. Most of all, I try to be tender to this particular issue. Sometimes I poke fun of it, because if it takes itself too seriously, lord knows where that will lead. Mostly I acknowledge it, and honor it as a part of me.

But on those rare occasions I get the itch, I’ll be damned if I don’t want it scratched.