To the Last Knuckle

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This is my first story published on Literotica. It might not fit neatly into one category over another. The narrative focuses on a guy’s introduction to the unexpected joys of buttplay. There are BDSM elements to it, but I feel like, in the end, it’s an Anal adventure 🙂

I want to sincerely and wholeheartedly thank LAHomedog, for your help and guidance in editing and reshaping this story. Your insights were so key to making this what it is.

So, I hope you enjoy reading this as much as I enjoyed writing it!

***

“Go for it, man,” my buddy said. “If you don’t, I will.”

The Falconer was packed on a Friday night. It was the standard post-work set, pressed shoulder-to-shoulder and ready to do some damage. Men in half-removed suits soaked through with spilled beer and sweat. Women in conservative office attire, their hair mussed and smoky.

“Seriously, dude, she’s been eye-fucking you since we got here.”

As the night wore on, the lights turned lower. But there was no way I could miss her. That red mane of hair, that flawless ivory skin, those cognac brown eyes locked on me. Her full, crimson-painted lips, kissing the rim of an oversized wine glass. And that was just above the neck.

“This is why we came out, isn’t it?”

My friends were nudging me. They meant well, but my feet were frozen solid.

Our stated reason for a night on the town was to get me laid. My first weekend as a single man in eight years. The Falconer was a Midtown sports-and-brews watering hole, but it attracted a young, moneyed clientele on Fridays. Were the ladies stacked deep enough for me to find a willing partner?

That was the rub.

My longtime girlfriend had moved out Monday, the day after I asked her to marry me. It would be generous to call that a kick in the nuts. It felt a little more like emasculation.

Was I only proposing to keep her from walking out? That was possible. Anyway, she said no. I asked if she could see herself changing her mind. And again, she said no. I asked her if I could do something to make her love me again. Her answer leveled me:

You’d have to stop being you.

We didn’t talk after that. I went to bed, heartsick and thoroughly unmanned, and she started packing. When I got home from work on Monday, she was gone.

So, yeah – having my first casual sex in nearly a decade would have been peachy. But at the time I felt like I deserved credit for just getting out of bed in the morning.

I deserved a gold fucking star for dressing up nice for a night out: tailored shirt, slim-cut designer jeans, and a decent pair of Italian suede loafers. I even dusted off the big-face Breitling Navitimer watch. It cost about the same as a month’s rent on my luxury one-bedroom on the Upper West Side. The point was, I was suited up for success, but my confidence was in tatters.

Mickey, my oldest friend in the city, took me aside.

“Listen, Clay,” he said, fairly steady considering he was four beers in, “you do what you gotta do tonight. I get it. That bitch fucking shanked you. But my considered advice is that getting your dick wet is never bad for a broken heart.”

I thanked him and stole a glance at my admirer. She sat primly, her spine arched like a French back chair. That gossamer skin and those fiery locks were set off perfectly by her form-fitting black shirred dress. The dress strained tantalizingly to contain a firm-yet-succulent ass and round C-cup breasts.

“Besides,” Mickey whispered, “you’re not gonna do better than that any time soon.”

I sucked down the last of my Manhattan and stepped forward.

What’s the worst that can happen. She takes a drink from you and gives you the cold shoulder. You’ve had worse. You can just go home and jerk off thinking about those melon tits.

“Hi,” I shouted hoarsely over the surrounding din.

“Hello,” she replied.

“I, um, I noticed you … watching me.”

“I was watching you. So kind of you to notice. I saw you watching me, too.”

“Really?” She nodded. “Is that okay?”

“Very okay. I was hoping you’d come over.”

Okay, cleared the first hurdle. This was proceeding passably.

“Are you almost done with that wine?” I asked. “I’d love to buy you another.”

“I’m good.”

Ouch.

Then she added: “Looks like you’re to one with an empty glass. Let me buy you a drink.”

A little unorthodox, but who was I to refuse?

“I’ve been drinking whiskey? How about a Willett Rye, neat.”

“Check you out, GQ!” she teased. “Maybe I should ask him for a couple drops of spring water in it.”

She flagged the bartender and ordered for me. Almost immediately – despite the throngs of drinkers – he poured my whiskey and refilled her wine.

“Friend of yours?” I asked. “I’ve never waited less than twenty minutes for a drink here.”

“I guess I have a pleasant disposition,”

There was something almost professorial in her demeanor, like every word she spoke was the beginning of a seminar. Which was quite alluring. afyon escort I’d been an accountant for five years. More specifically. I was an Accounting VP at a prominent, extremely successful property developer. It was perfectly lucrative, but honestly, it was also boring as all fuck. In another life, I’d have loved to be a philosopher or a poet. I guess I was stuck on having a high-end apartment, nice clothes, and good whiskey.

Still, this girl took me back to those humanities courses I had to take in college. Those serious chicks, full of ideas and barely-constrained passions, mouths parted as they listened to a lecture on DH Lawrence.

“I’m Clay,” I said.

“Gretta,” she replied. “Are you here with the Wrecking Crew?”

She gestured to my compatriots. Two were already half-unconscious at the bar. Mickey was in an argumentative mode, all but shouting at the dude next to him about something.

“Yep,” I admitted, “I don’t normally hit the town with them, but …”

“But what?”

“I guess this is the first night in a long time where going out with the guys is my best option.”

“Hmm,” she replied, smirking, “but you still snuck away, didn’t you?”

“Like I said: I couldn’t help noticing you.”

That seemed to please her. She took a satisfied sip of her wine and fluttered those smoky eyelashes. I glanced down to catch sight of her picture-perfect cleavage, two heaving breasts pressed together just so in her dress. No strain from a constrictive bra. This was pure gravity-defying talent.

Eyes up, champ.

“Unfortunately,” she said, scooting that fine ass off her seat, “I am here with coworkers. Like you, I needed to escape.”

“I see, and they are …”

“In the back.”

“I’m sure they can survive without you.”

“I’m not sure they can. I’m the admin assistant for this group, which should make me the bottom of the food chain. But since I’m in charge of planning these extracurricular team outings, I have to make sure they don’t freak out when the sliders are depleted.”

I could commiserate to a certain extent. I was useless at the office without my assistant holding my hand.

“Well,” I mumbled, “um, it was great to meet you, Gretta.”

She gave me a little, insanely cute wink.

“You too, Clay. I hope we run into each other again before the night’s end.”

Gretta spun around and sashayed away before I could speak. My eyes locked on that beautiful round ass, popping back and forth with each confident step. Gretta had mastered whatever exercise regimen kept her fit and tight, but still bouncing in all the right places.

It had been so long since a woman had looked me up and down and appraised me. For years, I moved through my day in a foggy state of good-enough-ness. Stay with someone long enough, and you both just sort of overlook the assets along with the flaws. You fail to notice when the other wanders naked through the room after a shower. You have the same good-enough sex at the same time of the day. Even your kinks become rote.

So to have a person actually think you’re hot … to have someone look you over – that was fucking thrilling.

So why had she walked away?

You’re a good-looking dude, right? Not be a bodybuilder, exactly, but you keep it trim. A decent head of hair, which you even know how to style. You spring for the decent soap and aftershave and cologne. And in these jeans, you’re sporting one hell of a down-the-thigh bulge.

“Swing and miss?” Mickey asked, sidling up.

“Hard to say…”

“That sounds like a miss. What’s that?” he asked of my drink.

“Willett. She bought it.”

“She bought you a drink? Shit, man. You have been out of the game for a while.”

I drained the last of the rye. Mickey said he had the next round.

***

An hour later, I was galloping down the stairs to the Falconer’s subterranean toilets. A little bleary, a little cock-eyed. Worse, I was fiddling with my phone, seriously considering texting the ex.

Maybe she’s missing you too, that shitty voice in my head whispered. Only one way to find out.

“Hello, again.”

My eyes darted up, and there was Gretta, emerging from one of the unisex toilets. Her big brown eyes were a bit glazed too. I stowed the phone and puffed out my chest.

“Erm … hello to you. Glad to see you. How’s the office crew?”

“Gone. I was going to have one nightcap and be on my way. How’s the frat pack?”

“Oh good. We’re about to do a keg stand, followed by some homoerotic wrestling.”

We both laughed. When she said she hoped they’d connect again, it felt like a kiss-off. But she stuck around. I was surprised, honestly.

“So,” she said, “off to … tap your keg … as it were?”

I assumed that meant take a piss, so I shrugged my shoulders and nodded.

“Well, you’re in luck. I just finished here, and I am militant about proper bathroom etiquette. So, I can confirm it’s in good working order.”

She held open the door. afyon escort bayan A standard midtown watering hole bathroom – cinder-block walls papered over with band and booze stickers, which in turn were scrawled over with filthy graffiti messages. But true to her word, the facilities were clean and looked perfectly functional. I thanked her and stepped in.

Just as I turned to shut the door, I saw she’d stepped in behind me and snapped the bolt.

“Hey now,” I stammered. Then she stopped my mouth with hers.

The location wasn’t particularly romantic, but it was titillating. Public, forbidden, sudden – Gretta’s tongue snaked between my parted lips and probed my mouth greedily. We made out like soused college students. She raked her fingernails under my hair and across my scalp. I took hold of her waist and pulled her to me, our bodies tight and writhing together.

“You taste good, Clay,” she moaned.

“You are … amazing!”

She reached down, removing my right hand from her waist and pressing it under her dress. Her nipple was erect and tight. I was more than a little surprised to feel a curved metal barbell speared through it. Turned out my studious young professional had a pierced nip.

I massaged her heaving orb as we kissed again. She was wearing this gloss that reminded me of a sorority girl: strawberry cream. It was so fucking innocent, totally at odds with the squeals of delight she made between kisses.

“Goddamn,” she cooed, “your hands feel so fucking nice on me.”

I groaned in agreement. My cock was getting harder by the second, pressing desperately against my jeans. Her hand drifted down my washboard stomach to feel around my package. She broke the kiss once she had a hold on me.

“Oh my,” she marveled, “that’s very impressive.”

“Thank you.”

Then, out of nowhere, she stepped back with a puckish smirk.

“You still gotta pee, big boy?”

I blinked a couple of times in confusion.

“It won’t be too uncomfortable, will it?” she asked, “Pissing with that hard dick?”

I hadn’t thought about my bladder since seeing her at the bottom of the stairs. She was right, though. I did have to piss … but I was also currently locked in a public bathroom with the hottest piece of ass in Manhattan.

“What are you saying, Gretta?” I asked nervously.

“Take it out,” she commanded, “I want to watch you piss.”

“I don’t get it.”

“It’s not rocket science, Clay. I only ever get to see cocks when I’m fucking them, sucking them, or jerking them off. That’s great and all, but we’re here and I want to see a hot guy peeing.”

“I’m not totally comfortable-“

Suddenly her hands were unbuttoning my fly.

“It’s not supposed to make you comfortable,” she said. “It’s supposed to turn me on.”

With one fierce movement, she pulled my jeans and underwear down to my thighs. I was completely exposed to her from the waist down.

“Holy shit,” she moaned, appraising my equipment. “That’s a mighty fine cock on you. I could have some fun with that. Now get over to that toilet.”

Flattery will get you anywhere, it seemed. I was done protesting. As I stepped over to the toilet, Gretta turned on the faucet.

“A little inspiration.”

I stood there a minute, feeling ridiculous. For all the drinks I’d downed in the last couple of hours, nothing was flowing. It didn’t help that my cock was at half-mast already and the way Gretta was eying only stiffened it more.

“Stagefright?” she sang in my ear.

“I’ve never been on this exact stage before is all.”

“Maybe I can help.”

She reached over and took a gentle hold of my meat. Her warm, dainty fingertips teased the ridge of my shaft.

“I’ll aim for you, sexy. You just shut your eyes and let that pee flow.”

I did as she said, squeezing my eyelids closed and focusing on the sound of running water. Exposed, vulnerable, trying to muster piss for this strange seductress, I clammed up. My balls pulled in, and my sphincter clenched tight as a drum. I thought of a water balloon with a pinprick leak, slowly deflating as a thin stream of water pours out.

Then came a trickle. I exhaled, and the stream intensified. I felt the pressure on my bladder flare, then slowly relieve. Over the sound of my fire-hose piss hitting the bowl, I heard Gretta’s ragged breath.

My eyes opened to one hell of a show. She was holding my pissing cock with one hand. The other was buried down the front of her lace panties. She’d hiked up that dress and was flicking her clit frantically to the sight of me pissing.

“Fuck, that’s hot,” she groaned.

“You like me peeing for you, baby?” I heard myself asking.

Her hand curled around my half-erect cock and stroked more piss out of me. We kept this up until my well ran dry.

“Fuck yeah! Thanks, sexy,” she whispered hotly against my ear while giving my dick a little shake. “That was great.”

I reached around her waist, but she wriggled away.

“Unfortunately,” escort afyon she said, pulling her dress back down, “I gotta go.”

She’s unbolted the door and slipped out, blowing me a kiss as she disappeared.

Holy fucking shit! What was that? Was she just fucking with you?

It was a distinct possibility. For a moment, I considered just accepting it. If she was just trying to work me up and leave me hanging – so to speak – at least she did it in here where no one could see.

I considered grabbing my flagging rod, giving it a few solid jerks, and coating the bathroom with my jizz. But no, I zipped up instead. I had to at least try to follow her. If she flipped you off, who cared?

***

My buddies were pretty much falling down as I passed them at the bar.

“Dude,” one shouted, “we saw your redhead.”

“Where’d she go?”

“She’s outside. Told us to tell you you had two minutes.”

I waved and bolted out the door. Immediately outside the Falconer, a gaggle of smokers turned to look at me. I must have looked fucking crazy to them, jogging out of the bar and spinning around looking for Gretta.

I found her, though, seated in the back of a cab on the corner. The back door was open, and her back was pressed against the far window, so she could stare right at me. Her glassy-eyed grin said she was hoping I’d follow.

“You coming, sexy?” she called.

I didn’t hesitate. I sprinted the twenty yards to the corner, slid in beside her, and shut the door.

Our mouths collided. Gretta devoured me. She locked her lips around my tongue, sucking on it like it was my straining, hardening cock.

Then, she broke the embrace, pushed me back, and turned to the driver.

“Brighton Beach,” she ordered. “East 11th and Neptune.”

We started moving.

Her legs were open to me, revealing a delicate lace thong barely able to contain her engorged, saturated pussy-lips.

I processed what she’d just told the driver.

Brighton Beach? Even in light traffic, that was a forty-five-minute drive.

“I have place up on 81st,” I whispered, helpfully.

“Wow,” she whispered back, “I guess you’re going to be a long way from home.”

Gretta had spoken.

***

In the unlit hallway of her second-floor walk-up, I trod lightly on ancient plank floors, keeping one hand on the plaster wall, gummy and uneven from coat after coat of primer. I nearly tripped over a pile of sneakers and umbrellas by the radiator.

“Watch your step, slick” she laughed, opening her bedroom door. “Don’t want you injuring yourself when things are just getting interesting.”

Gretta’s bedroom was small, spartan. A queen bed, old cherrywood – probably bought secondhand – with a burgundy duvet and matching shams. The only other item of note was a pretty nice ash-gray dresser-vanity combo on the other side of the room, a big rectangular mirror reflecting ourselves back at us. I was taken aback at how mussed my hair was. I shouldn’t have been. The whole ride here, she was raking her hands through my hair as we made out like teenagers.

Gretta ceremoniously lowered the dimmer to half, then approached me and planted a deep, sensual smooch. I reached out to take her in my arms, but she backed away.

“Not just yet. Take off your clothes.”

I saw in that ravenous expression that she needed to see every inch of me. Quickly, I popped the buttons of his shirt and tossing it on the dresser. Next, I kicked off my shoes. I started unbuttoning my pants, but Gretta stopped me. She moved in close and ran her hands over my hairless chest. Her forefingers made little circles around my nipples, giving me a shiver. Then without warning, she grabbed one nipple between her thumb and fingers and squeezed hard. I let out a small gasp.

“A little pain can be nice, right?”

So, she likes to be a little rough.

Gretta ran her nails lightly down my torso. She lowered herself to the floor and peeled off my underwear. My stiff cock sprung up from its cotton casement and nodded excitedly at her, a filament of precum dangling from the end.

“Oh my god,” she remarked, letting her warm breath caress the rosy cockhead. “I’ve wanted to taste your cock all night.”

“Do it. I gotta feel your lips on me.”

I quaked with pleasure as Gretta flicked her tongue across that head, tasting my precum. She hummed in approval, then descended on me. Goddamn, she was good. Her tongue twirled around me. Her mouth flooded with warm saliva as she bobbed greedily on my shaft. It felt divine, sliding out whenever she reached the hilt, dripping down my balls.

Her hand was working overtime, too, squeezing and twisting my wet sack with increasing severity. Each pulse of pressure shocked me, a delirious mix of pleasure and pain. I moaned with each squeeze, which only encouraged her. Then the other hand joined in, batting my testicles while the first hand, wet with her spit, massaged my perineum.

All the while she sucked and nibbled around my twitching meat. She was a maestro, and it had been so long since I had a mouth around my cock. It dawned on me that I was listing closer and closer to a premature orgasm.

Keep it together, man. Hold back, whatever it takes. Think of sports, work, elderly relatives.

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