The 2010s were a chapter of unrestrained decadence and debauchery in my life. After a relationship that ended in spectacular fashion, I was single in New York City, a place that offers everything and asks only that you have the nerve to take what you want. I was decent-looking, well-mannered, gainfully employed, and just pervy enough to charm women way out of my league. For most of my 30s, I was lucky enough to sleep with more than my fair share of beautiful women who called the city home.

Mary was one of these women, a lifelong New Yorker in her mid 40s who gave me my first rimjob.

I responded to an ad on Craigslist, back when Craigslist was still a haven for deviants like me. It was the middle of the day, in the middle of a workweek, and I was smack in the middle of nothing. So, I pulled up Craigslist on my phone and started scrolling through the Casual Encounters section. After wading through countless hooker ads and spam posts, one caught my eye. It was something along the lines of: “W4M - I’ve been up all night and still couldn’t sleep. Want to keep the party going?”

Now, I’ve dabbled in illicit substances, sure, but they weren’t for me. Still, this was the city, and who am I to judge how someone else gets through their day? All I knew was that I was horny, bored, and this post had the unmistakable ring of authenticity, something that might just end with my dick inside a willing woman.

So, I shot my shot and replied. I don’t actually remember what I wrote, probably some attempt at being vulgar, masked as wit. It didn’t matter, though, because I got a reply and an invite. Sometimes, timing is everything.

And just like that, I slipped out of the office without anyone noticing, hopped on the subway, and rode the 9 stops to where she lived.

Mary lived in a part of the city where you either had to be rich or lucky enough to have a grandmother who added you to her lease before she passed. Mary was the latter. Her building was old—a post-war relic with outdated decor, doors that didn’t close properly, and an intercom system that was little more than muffled static.

I rang her apartment number, and after a brief pause, she buzzed me in.

When I reached her floor, the hallway was dark, the lights likely out due to poor maintenance. Her door was ajar, so I let myself in. I know, I know, walking into a stranger’s apartment could’ve ended in an ambush, with me waking up in a tub of ice, minus a kidney. But, as I said, this was a chapter of my life where I was reckless and led entirely by my dick. Luckily, I didn’t die. Instead, I walked into an experience I’d never forget.

Her apartment was big by New York standards. I made my way through the narrow hallway and into her living room, where I saw her: a dirty blonde, bent over, hovering in front of her iMac. The room was dim, the shades drawn tight, lit only by the soft glow of her computer screen and a dim floor lamp in the corner.

“Hi,” I said, just loud enough to announce myself.

She glanced back, acknowledging my presence, then returned to whatever she was doing.

Mary looked to be in her mid-40s, thin and a little rough around the edges. You could tell she’d been a hottie in her youth, and with some effort, she could still turn heads. She wore an oversized sweater that hid her body and a pair of leggings that stretched over her long, scrawny legs.

Standing next to her, I asked, “What are you looking at?”

She ignored my question, turning to ask, “Do you have any supplies?”

“No, I don’t.”

She didn’t seem disappointed or annoyed. Instead, she just shrugged, a smug little gesture that told me she didn’t care either way.

Since I’ve gone this far, I decided to push my luck. Worst case, she’d tell me to leave. I stood behind her and grabbed her ass, testing the waters.

She didn’t turn around, but she pushed her hips back into me, indicating to me that it’s ok to touch. Taking that as my cue, I let my hands roam free, fondling this woman I’d just met in her dimly lit apartment. My hands slipped under her oversized sweater, and I discovered she was wearing nothing underneath. I cupped her bare breasts—soft, with a slight sag—and found her nipples. As I pinched them lightly, I felt her body respond.

That was enough to snap her out of whatever it was she was doing on her computer. She turned around, pulling the giant sweater off in one smooth motion, revealing her bare breasts. For the first time, she looked directly at me.

Without a word, she nodded toward the couch—a silent command—and my pants were undone before I could think twice. Shoes, socks, jeans, boxers—gone in a messy shuffle. My ass hit the itchy fabric, the kind of couch that screamed bad decisions and questionable company. But none of that mattered, because then she dropped to her knees and took my cock in her mouth.

There wasn’t finesse, it was just chaos. Wet and loud, spit everywhere. A lot of movement, little precision. She wasn’t doing it for my pleasure; she was in her own world and I was just along for the ride. And yet, the whole scenario was incredibly sexy. It wasn’t the best I’d had, but it wasn’t about that. This was about being devoured like I was her favorite meal and she hadn’t eaten in days.

Then she shifted, licking my balls, and I was in heaven, since it was one of my favorite things. She took it further—further than I’d ever been. Her tongue wandered lower, her hands guiding me into some awkward, legs-splayed position I didn’t even know I was capable of. And then it happened, warm, wet, penetrating… her tongue was licking my asshole.

I didn’t know my body could feel like that. I didn’t know there was a button deep inside me that hadn’t been discovered. It was a sensation so intense it bordered on unbearable. Part of me wanted to push her away, to regain some composure, but the larger part, the curious part, begged to see what came next.

The sensation was like nothing I’d ever experienced before. Her tongue moved with this crazy kind of precision, like she was digging for gold. Every lick of her tongue was like a shock ran through my whole body. I was squirming, my legs shaking, my hands gripping the cushion like they’d keep me grounded. It felt too sensitive, way too vulnerable, but somehow, I couldn’t make myself stop her. It was terrifying and amazing all at once.

And then she found something deep inside me, this spot I didn’t even know existed, and I completely lost it. My back arched, my breath caught, and suddenly I wasn’t in control anymore. It felt like a dam bursting, like I couldn’t hold back even if I tried. It was chaotic. It was primal. It was everything I didn’t know I wanted. And before I could stop it—or even try to savor it—she pulled me over the edge. No one had ever made me cum that fast, and definitely not like this.

I’d love to tell you I erupted in some cinematic, porn-star way, all over her tits, her face, her eager, waiting mouth. But the truth was way less tidy. The first shot went straight over my head and onto that damn itchy couch. The rest landed on my stomach, and maybe a few drops got onto her hair.

It was over as quickly as it began. When it was over, I just lay there, trembling and trying to catch my breath, completely wrecked and wondering what the hell had just happened. She got up and handed me a few sheets of paper towels. I wiped off what I could, got dressed, muttered a half-hearted goodbye, and left her apartment.

Stepping back into reality, the sun seemed too bright and the air too sharp. I made my way back to the office as if I’d just returned from a long lunch. Yet something had changed, I was now a true believer in the male G-spot.