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Wall Street Banker's First Spanking

by M.P.

Copyright on this story text belongs at all times to the original author only, whether stated explicitly in the text or not. The original date of posting to the MMSA was: 17 Feb 2018


Sam’s butt was itchin’ for a spankin’

You’d never suspect it if you saw him in his suit and tie walking to the investment bank where he worked in Lower Manhattan. At 24, he still looked like a college bro dressed in his big-boy clothes in town for a job interview on Wall Street, even though he was an analyst up for promotion to associate in only a matter of months. He had combed-back light brown hair and piercing hazel eyes, with a plump butt filling out the back of his charcoal gray suit pants.

Here’s the strangest part—Sam wanted to be spanked by another dude. As he’d be the first to tell you, he wasn’t gay or anything. Far from it, he loved nothing more than to grab a girl by the titties, and then fuck her right in the pussy. With his good looks and money, finding a girl to fuck was never much of a problem, even at only 5′9′’. He was never into sex with guys. He and his buddy Chad often spent lunch trading war stories about their sexual conquests.

Remember that chick, Mia, I told you about from Tinder, Sam said. Turns out that she’s a world-champ cocksucker.

Do tell, Chad replied with a smile, his Piaget watch glistening in the light streaming through the floor-to-ceiling windows at Bulls Cafe, where they met most days for lunch, sometimes with other analysts in their group, located in the 10th floor sky lobby of their building.

Her tits bounced like a porn star’s, while she was bobbing up and down sucking me off, Sam explained. The best part is she was dirty too—she sucked my nuts and even licked my taint.

Dude, you totally should have gotten her to eat your ass, Chad said.

Ew—that’s nasty, Sam replied, looking down at his monogrammed, SAB, cufflinks.

I’m telling you, those fags are onto something, Chad said. I was at a bachelor party in Vegas last month. Long story short, we ended up at a whorehouse. This MILF started licking my ass totally out of the blue, and when I came, I shot like a firehose!

Call me lame, Sam replied, but an old-fashioned blowjob is good enough for me.

Before Chad could respond, the waitress arrived with their burgers.

Though he’d never admit it to Chad, Sam had something kinkier in mind for his butt.

The spanking fantasy had emerged only recently, coming out of left field. It hit him hard late one night when he was still at work, high up on the 38th floor of his office building, as he passed one of the secluded conference rooms. He started to fantasize about one of the MDs, mostly 30-something year old straight dudes who looked like slightly older versions of himself, grabbing him, forcing him into the conference room, yanking down his suit pants, and then spanking him until he was crying and begging for it to stop. Instantly, Sam got rock hard.

It didn’t make sense. He never got spanked growing up and didn’t even know anyone who did. A coach on his college baseball team might have patted him on the butt once or twice after a good play, but that was far from the kind of pants-down, butt-burning spanking that he now coveted. Plus he was straight. Even if he accepted the whole spanking thing, which was weird enough already, he had no interest in getting spanked by a chick, only a dude, which made the fantasy all the more confusing. Nor did it fit his personality. With his Ivy League pedigree and six-figure salary, Sam was used to being in control. Still, Sam wasn’t one to say no to his dick and if it was into dudes spanking dudes, then so be it—this was something he’d just have to explore.

***

One night in early August, Sam returned home from work at almost 1 AM, to a contemporary, high-rise building in Battery Park City, facing the Hudson River, with a gym, pool, and 24-hour doorman. Earlier that night, Cullen, one of the VPs in his group, chewed him out over an error in a valuation, a DCF analysis, for a presentation to an important biotech client. As much of a Big Swinging Dick as Sam normally was, by the time Cullen was done with him, Sam was on the verge of tears. When the lecture ended, Sam wondered what it would feel like to get put over Cullen’s knee for a legit spanking until his butt was on fire as punishment for his fuck-up.

Mr. Bradley, I have a package for you, the night doorman said, as Sam walked by the front desk, holding his leather briefcase and folded-up suit jacket.

Having more pressing things on his mind, Sam totally ignored the man.

As soon as he got to his apartment, a darkly-colored, masculine-looking one bedroom with a solarium dining room that seemed to jut out into the river, Sam headed into his bedroom and stripped off his clothes, feeling an almost overpowering urge for a spanking after the day’s events. That left him wearing only a pair of blue boxer briefs, barely big enough to cover his butt. Then turning back towards his bedroom mirror, Sam cupped his hand and started spanking himself with as much force as he could muster, pretending it was Cullen doing the spanking.

You’re lucky the deck didn’t go out yet, Cullen said in Sam’s fantasy. Otherwise, I’d be using the hairbrush.

At the climax, Sam pulled down his boxer briefs, exposing his smooth butt, and finished the spanking, landing the hardest blows yet. Despite Sam’s best efforts, his butt was barely red.

Almost immediately, Sam felt embarrassed at his feeble attempt to recreate a spanking. What would Cullen—or for that matter, Chad—think if he could see me now? Sam worried, beginning to realize he was close to crossing a line. His six-inch dick, standing at full attention, had other ideas, though, forcing Sam to reconsider.

So what if this was what he liked? It’s not like he suddenly decided he wanted to screw or get screwed by guys. Besides, a dude like Cullen, with a salary approaching seven figures, had bigger things on his mind than the weird sexual proclivities of one of his junior analysts. Fuck ’em, Sam thought, his cockiness returning, they can kiss my red ass.

Harkening back to his frat days, Sam walked over to the solarium windows, bent over, and mooned the dark city 22 stories below him, pressing his ruddy cheeks up against the glass.

With that concern addressed, Sam returned to his bedroom and focused on what a revelation the spanking had been. The thrill of feeling a man’s hand slapping his bare behind, even if it was his own hand, had him ready to bust. It only took a few wanks of his throbbing dick for him to shoot a huge load onto his sheets, one of the most intense orgasms of his life.

Sam changed his sheets, put on his trusty Penn Baseball shirt and pajama pants, and, at a little after 1:30 AM, went to bed, a king-sized Restoration Hardware sleigh bed, for the evening.

How much hotter would the spanking be if it were another dude doing it for real next time? Sam asked himself, as he drifted off to sleep. He knew what he had to do.

***

It wasn’t easy for him to work up the nerve to join a site and begin the search for a dude to spank him. Being straight, Sam thought it wouldn’t matter what the guy looked like, but it turns out that it mattered a lot. What he wanted was a guy similar in background, but slightly older—an older brother type—to spank him with no expectation for sex. No daddies and no queers. That proved easier said than done. August was about to turn into September with no real leads.

While he was on the prowl, Sam became preoccupied with spanking. He stopped, maybe more like suspended, hooking up with girls while he pursued his spanking. He began bringing his iPad to work, so he could check his messages throughout the day. His jack-off fantasies began to revolve around the dudes in his office giving him the spanking he so desperately wanted. Most embarrassingly of all, Sam even fapped to the thought of his buddy Chad spanking him.

At a loss, Sam considered using some of his bonus money to hire a dude off one of those rent-a-boy sites to spank him. Isn’t that what other bankers would do in my shoes? Sam thought. Chad certainly would. But that seemed too risky. If he got caught, how the hell would he ever explain that? It would be the end of his career. The spanking wasn’t even likely to be very good—Sam wanted to get spanked by a dude who wanted to spank him.

Just as he was about to give up, Sam got a message from Glenn, a 6′2′’ dude with moppy brown hair and soft brown eyes. He worked in finance too, but on the tech side. Even though he was only 28, Glenn seemed to have lots of experience spanking guys. Plus he was ripped and had similar interests. The two traded messages, pics, and texts over the course of several days. Sam even shared with him his fantasies about getting spanked by his colleagues, especially Cullen.

But one text almost ended it all. Before Sam went to sleep on Friday night, he texted Glenn about how much he was into hairbrushes, his favorite spanking implement. He also mocked a couple of the flamboyantly gay guys who had been messaging him incessantly through the site. Glenn didn’t responded right away, causing Sam to worry that something might be wrong.

Dude, there’s something you should know, Glenn responded Saturday morning. I’m gay.

Sam considered whether this had been a giant waste of time. In all the messages they traded, Glenn’s sexual orientation hadn’t come up. Sam’s profile stressed his sexual orientation, but his gaydar hadn’t gone off with Glenn, so he just assumed that Glenn was straight too. To be fair, Glenn had never actually said as much. And he seemed like a normal dude, someone Sam could be buddies with. Be that as it may, could Sam really let a gay dude spank his straight ass? As hard as it was to accept that, it was even harder to believe there was a better option out there.

Fine—just no gay shit, Sam responded, before setting off on his usual Saturday morning routine. Stick to the spanking and we’ll be fine.

You don’t have to worry, Glenn wrote him back about a half hour later. It’s all about the spanking for me. But let me warn you—I spank hard. By the end, you might just be begging to suck my dick, if that’s what it takes to end the spanking.

That message might have, maybe should have, driven Sam away. Sam had no desire to suck a dude’s dick. But when he got Glenn’s message, on line grabbing coffee and a bagel at Zucker’s, he got rock hard in his shorts. Maybe it was the idea that he’d be in so much pain, so out of control, that he’d be willing to beg another guy to do something so repulsive that got Sam all worked up, but he decided right then and there that Glenn was his dude.

***

The two agreed to meet on Tuesday after Sam got off work. Sam preferred to meet at Glenn’s apartment. It wasn’t so much that he was worried about Glenn, as he was about the night doorman. All visitors to his building had to be announced. Given how late Sam worked, what would the doorman think seeing a guy dropping by to visit Sam at that hour only to leave a short time later? Sam didn’t want anyone in his building to get the wrong impression.

Monday night, Sam was so excited he could barely sleep. The fact that Glenn was a gay dude receded in importance. What mattered most was that Glenn was going to give him his very first spanking. By all appearances, Glenn would be a formidable spanker. Sam dreamed up a number of different scenarios, including his favorite—that he was a naughty employee and Glenn was his irate boss. In each scenario, the spanking ended with Sam in hysterical tears. Sam jerked himself raw until he finally fell asleep around 3 AM.

Tuesday morning, Sam paid extra attention to washing his butt in the shower, and picked out his new pair of Calvin Klein briefs, undies he bought specially for the occasion. Sam then put on a crisply pressed Hugo Boss suit and his lucky Hermes tie. Fully dressed, Sam gave himself a once over in the mirror and liked what he saw.

Next time you’re home, you’ll have a spanked butt, Sam thought.

At work, Sam found it difficult to concentrate on the deck he was supposed to be creating for a meeting later in the week, a pitch to a prospective client about potential strategic alternatives. It gave Sam a jolt to know that somewhere in the same city Glenn was out there, doing whatever it is that tech guys do, with a heavy right hand that was ready to spank Sam.

It was 11pm when Sam finally got out of work. It was a steamy August evening. At Glenn’s direction, Sam texted him as soon as he left the office. Glenn responded immediately with his address; he had been a little weird about giving it to Sam until he was absolutely sure that the meet-up was a go. Though Glenn’s place was only four subway stop away from his FiDi office, Sam hailed a taxi, lest he arrive at his spanking drenched in sweat.

14th and 6th, Sam said to the taxi driver.

The ride barely lasted 15 minutes. As absurd as it seemed, Sam was convinced the taxi driver knew exactly why Sam was heading there. As the taxi pulled up outside Glenn’s apartment, Sam started to feel butterflies in his stomach. This was different than meeting up with a girl for sex; this time his ass was literally on the line. As Sam swiped his platinum card, a new thought occurred to him. Would he be able to take a taxi home or would he be too sore to sit?

Sam got buzzed in and then took the elevator up to Glenn’s apartment. It was more modest than Sam’s, but looked like a normal dude’s apartment, an alcove studio, with a flat screen TV, PS4, and posters on the wall. The boys sat down on the couch in Glenn’s living room. Glenn was wearing just an undershirt and plaid boxer shorts. He looked exactly like he did in his pics. He could have been a dude in Sam’s frat or an analyst at his bank. And he was shredded.

After a bit of small talk, Sam started to feel hot, even though Glenn’s air conditioner was buzzing. Mind if I get out of the suit?

Of course not, Glenn grinned back at him, equally impressed with Sam’s good looks.

Wasting no time, Sam stripped down to his undershirt and briefs, folding his suit neatly on the nearby leather recliner. When Sam rejoined Glenn on the couch, the boys looked like two college friends shooting the shit in the dorm together.

So you want a spanking? Glenn asked with a smile.

That’s why I’m here, Sam replied.

No, you don’t—not really, Glenn responded. You only think you do.

I can speak for myself, bud, Sam said a little defensively, not sure where Glenn was going. I’ve been fantasizing about this moment since you first messaged me.

You’ve never been spanked before, right? Glenn asked.

No, but I doubt you’ve ever spanked a guy like me before, Sam replied smugly.

You’re not the first straight dude I’ve spanked, Glenn said. Let me tell you something—I know your type. What you really want me to do is slap you on the butt a few times, so you can go home and jerk off, before your girlfriend gets back. When the spanking gets serious, you’re gonna wanna tap out. You won’t be able to take it.

Sam grimaced. Glenn’s tough talk was turning him rock hard, leaving him throbbing in his tighty whities, but it was pissing him off too. Glenn was calling him out, questioning his ability to take the spanking. Don’t worry about me—you do your part and I’ll do mine.

Look, there’s nothing in the world I’d rather do right now than take you over my knee and spank you until your ass is on fire, until you are kicking and begging and crying and pleading with me to stop, Glenn elaborated. But you should know that’s what you’re up against. Once we start, I’m the one who decides when the spanking ends.

Who the hell does this guy think he’s talking to? Sam wondered.

Never one to back down from a challenge, Sam stood up and yanked down his briefs in a single gesture, until they were pudd