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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 puddled around his ankles. Then, bare assed, he bent over and mooned Glenn, waving his bare ass back and forth.

And this is what you’re up against, dude! Sam said, slapping his own behind. How do you like that? Does it turn you on? Is that why you’re scared to spank it?

Glenn almost laughed out loud, admiring what balls Sam had, what a bro he was, even as he was on the precipice of his first spanking. Then figuring it was time to get down to business—that he had duly warned Sam what was in store for him, and Sam had responded by literally sticking his ass in Glenn’s face—Glenn grabbed Sam from behind and wrestled him over his knee.

Before Sam knew what hit him, he was pinned down over the knee of another dude, a guy who had almost six inches on him. As much of a fight as he might put up, it was clear he wasn’t going anywhere, which was a huge turn on. Still, it was jarring to be manhandled like that.

Dude, what—

Before Sam could complete the thought, Glenn cupped his hand and set about starting Sam’s butt aflame.


So this is what a spanking is like, Sam thought, as the sting began to register.

At least initially, Sam impressed himself with his ability to take the spanking. Sure, it hurt, maybe even more than he was expecting, but it was also hot. If Glenn hadn’t been so much of a stud, and if he hadn’t felt so turned on, the spanking might have been rough. But as Sam liked to say to his banker buddies, And if my aunt had balls, she’d be my uncle!


Dude, stop spanking like a girl, Sam said, peering up at Glenn from over his knee.

Glenn paused, smiled, and then turned up the spanking another notch, confident that, soon enough, Sam would live to regret those words.


Sam did have to give Glenn credit where credit was due—the dude had a hard hand. Glenn spanked at a brisk pace, but powered up between swats too. It was enough to keep Sam on edge, worrying about where the next blistering swat would land. As the spanking crossed the one minute mark, the lower part of Sam’s butt was starting to feel sore.

You were right, Glenn said. I’ve never spanked a guy with an ass this tough before.

Really? Sam replied, pleased, but surprised, that Glenn was willing to concede defeat so soon.

Fuck no! Glenn said. Don’t be a dummy—we’re just getting started.

Sam blushed, embarrassed that Glenn seemed to have his number. He thought about what he must look like, his patrician butt turned over Glenn’s knee, which was strangely arousing. He was also curious, by the time the spanking ended, where he’d rank in the pantheon of guys Glenn had spanked, hopefully somewhere near the top.

Before Sam could dwell too much on that, Glenn changed the rules on him, transitioning to a rapid-fire method of spanking that got Sam groaning and yelling.


Wow, so I guess spankings hurt straight butts too! Glenn said mockingly.

Don’t let him get to you—you can do this, Sam gave himself a pep talk. But as his butt got hotter and hotter, it dawned on him that there was no end in sight, causing his arrogance to give way to panic. Sam’s stoicism collapsed fully after another minute of uninterrupted butt slapping. His arousal no longer sufficed as a buffer for the pain of the spanking.

SPAAANK! Owww! SPAAANK! Owww! SPAAANK! Come on man! SPAAANK! Ouch SPAAANK! Fuck! SPAAANK! It hurts! SPAAANK! Ouch! SPAAANK! Oww! SPAAANK! Oww-owww! SPAAANK! Fuck off. I said that hurts!

Still think I spank like a girl? Glenn asked, taking a special pleasure in setting this dude’s ass on fire. Not only was Sam hot, but he also was a banker, and Glenn spent most of his working hours getting his balls busted by bankers struggling to do basic shit on their computers.


This wasn’t how it was supposed to go, Sam thought, kicking his legs in a futile attempt to get his butt out of the line of fire. It was nothing like his prior attempt at a self-spanking, which seemed more ridiculous with each passing minute over Glenn’s knee. His butt felt scalded and all he’d gotten so far was a simple hand spanking.

OK! OK! Sam yelled. I admit it!

SPAAANK! Yooooow! SPAAAAAANK! Yowww-owww-ouch!

You admit what? Glenn asked, letting those last couple spanks set in.

You were right! Sam cried. These burn like shit. Come on—give me a break...

That’s not how this works, Glenn said. When we’re done here, you can go back to being Master of the Universe. But until then, you’re just another boy learning how much it hurts to get his butt spanked!


Fuck man, Sam said. As much as he hated showing weakness in front of another guy, a gay guy no less, his throbbing butt didn’t leave him very much choice.

I’ve spanked 18 year old twinks who could take it harder than you, Glenn mocked. I thought you were supposed to be some kind of alpha male?

Sam tried hard to get his swagger back—thinking of all the girls he’d screwed, his summer weekends in the Hamptons, his eye-popping bonus—but none of that did him any good in the moment. Fuck it, I’m a puss. Just stopping me hitting so hard!

SPAAAAAAANK! Please dude! SPAAAAANK! Please!

Do you think Cullen would stop spanking you, after you fucked up his presentation, just because your butt was starting to get a little warm? Glenn asked, recalling Sam’s earlier texts.

That taunt got Sam’s cock twitching. Glenn was proving to be every bit the disciplinarian the Cullen of Sam’s fantasy had been. Sam knew that later that night he was going to shoot a huge load, but there was still a lot of spanking left until then and he was already nearing his limit.

SPAAANK! Nooooo! SPAAAAAANK! No! He wouldn’t, but please! SPAAAANK! Please stop! SPAAAAAAANK! It’s too much!

It’s a spanking, guy—it’s supposed to hurt, it’s supposed to be too much, Glenn said. This is what you said you wanted. Next time, be careful what you wish for!


Too bad, so sad, Glenn said. I’m a man of my word. I promised you a real spanking and that’s exactly what you’re gonna get, whether you like it or not!

Glenn went to town on Sam’s sit spots, spanking twice in quick succession on exactly the same spot, before moving on to his next target, spreading the fire engulfing Sam’s behind.

SPAAANK! SPAAANK! Ouchhhhh! SPAAANK! SPAAANK! Ow-ow-ouch!!!! SPAAANK! SPAAANK! Not there! Please! SPAAANK! SPAAANK! Yow-oww-ouch! I’ll be good! Please! SPAAANK! SPAAANK! OWWWWWW! SPAAANK! SPAAANK! Nooooooo more! SPAAANK! SPAAANK! Owwww! SPAAANK! SPAAANK! Ouchie!

Now that you’re warmed up, it’s time to get serious, Glenn said, relishing every moment of this spanking. Go to the bathroom and bring me the hairbrush.

Sam almost burst into tears on the spot. Please—

If I have to tell you twice, I’ll make you spread your cheeks apart and then spank the inside of your crack with the brush! Glenn warned. Straight boy or not, there is no surer way to ruin a guy’s week than to spank his crack and asshole.

His briefs still around his ankles, Sam waddled over to Glenn’s bathroom, which was dated, but clean. There it was, waiting right next to the sink—a classic wooden hairbrush, the kind that a 1950s mother might use to comb her hair, and a 1950s father might use to spank his son. It was true to Sam’s fantasy, and it sent a shiver down his spine.

This time, Sam knew what he was in for, but it didn’t help at all. Glenn was going to break him, make him feel small and powerless, cause him to disgrace himself, and there was nothing he could do about it. In no time at all, Sam was back over Glenn’s knee for the grand finale. Despite the pain and fear, Sam’s dick was still rock hard, maybe harder than when he first started.

WHAAAACK! Ooooooooo! WHAAAACK! Oooooo man! WHAAAACK! Oooooooo god! WHAAAACK! Stop! WHAAAACK! Stop-ow-stop! WHAAAACK! Please dude! WHAAAACK! Please! WHAAAACK! Oh-oh-oh! WHAAAACK! Bwaaaa! WHAAAACK! Awwwww! WHAAAACK! Bwaaaa-aaaa-aaaaaaa!

Knowing that the spanking was getting serious, Glenn grabbed Sam’s hand and pinned it to the small of his back. Glenn wanted to teach Sam a lesson, but he also wanted Sam’s first spanking to be memorable. Sam was hot, maybe the hottest guy he’d spanked before, and while Sam was struggling now, he was still aroused. Glenn wanted to be sure that he fulfill Sam’s fantasy, even if Sam couldn’t appreciate that in the moment.

You knew how important the presentation was and you still fucked it up! Glenn yelled.

WHAAAAACK! I’m sorry! WHAAAAACK! I’m sooo sorry! WHAAAAACK! Aaaaaaaa! WHAAAAACK! Aaaaa! No! WHAAAAACK! I’ll never do it again! WHAAAAACK! I’ll be more careful! WHAAAAACK! Please! WHAAAAACK! Bwaaaaaa! WHAAAAACK! Aaaaaaaa! WHAAAAACK! Aaaaaaaaa!

You almost lost a client, almost made Cullen lose a client, just because you’re a giant screw-up who can’t do the work of a first year analyst? Glenn lectured.

WHAAAAACK! No! No! WHAAAAACK! I’m sorry! WHAAAAACK! I’m sorry I screwed up! WHAAAAACK! I’ll do better! WHAAAAACK! I promise! WHAAAAACK! Please! WHAAAAACK! Aaaaaaaa! WHAAAAACK! Owwww!

What happens to bad boys who fuck up their work? Glenn asked.

WHAAAAACK! Aaaaaaaa! WHAAAAACK! Bwaaaaa! WHAAAAACK! They— WHAAAAACK! They get spanked! WHAAAAACK! Aaaaaa! WHAAAAACK! Ow!

And how do they get spanked? Glenn asked.

WHAAAAACK! Bwwaaaaa-aaaaaa! WHAAAAACK! Aaaa! WHAAAAACK! H-H— WHAAAAACK! H-Hard! WHAAAAACK! Aaaaaaaa! WHAAAAACK! On their bare butts! WHAAAAACK! On their bare butts! WHAAAAACK! On their bare butts!

Damn right, Glenn said.

After that, the spanking devolved into a whirlwind of yelling, begging, screaming, and crying.

WHAAAAAACK! Bwaaaaaa-aaaaaaaaaaah! WHAAAAAACK! Stooooooop! Noo! WHAAAAAACK! P-please stop! WHAAAAAACK! Aaaaaaaaaaaaaaa! WHAAAAAACK! No more spanks! WHAAAAAACK! No spanks! WHAAAAAACK! Boo-hooo! WHAAAAAACK! Aaa-aaaaa-aaaaaa! WHAAAAAACK! Can’t take it!

Beside himself, Sam made one final, desperate attempt to get out of the spanking.

WHAAAAAACK! Okkkkk! WHAAAAAACK! I’ll do it! WHAAAAAACK! Illdoit! WHAAAAAACK! Please! WHAAAAAACK! Aaaaah! Please! I’ll do it!

You’ll do what? Glenn asked, not understanding what Sam meant.

WHAAAAAACK! I’ll suck it! WHAAAAAACK! I’ll suck your dick! WHAAAAAACK! Please! WHAAAAAACK! Just stop spanking me! WHAAAAAACK! Please!!!!

Glenn had forgotten about the text. There was no surer sign, however, that a spanking was a success than hearing an arrogant straight banker begging to suck dick just to avoid more whacks with the hairbrush. Not wanting to overdo it, Glenn finished with ten final blows.

Once the spanking ended, and Sam had taken a moment or two to pull himself together, trying not to dwell on how badly he’d taken the spanking, how much he’d embarrassed himself, Sam climbed off Glenn’s knee, got down on his knees, and, wiping the tears away from his face and the snot away from his nose, looked up at Glenn with pleading eyes.

What are you doing there, bud? Glenn asked.

I, um— Sam struggled to say it out loud. I promised to give you, um, a blowjob.

Glenn snickered. Dude, I’m not gonna really make you do that. It was just a joke.

Really? Sam asked.

Of course, Glenn said. I’m not that kind of guy.

Relieved and almost a little touched, Sam put his head down on Glenn’s lap and started crying again. Glenn rubbed Sam on his back and comforted him through the worst of it.

What time is it? Sam asked, standing up and beginning to gather his stuff.

12:18, Glenn replied, noticing that Sam’s butt was purple in spots, no doubt because of the hairbrush.

Fuck me, Sam said, feeling physically and emotionally exhausted from the spanking, way too sore to sit through a taxi ride home. Dude—I hate to ask, but mind if I crash with you tonight?

No problem at all, Glenn replied, privately elated that this guy, who was basically a wet-dream come true, wanted to spend the night at his place.


About 15 minutes later, the boys were both in Glenn’s bed in the alcove of the apartment, positioned side by side. Glenn was still in his boxers and t-shirt; Sam was in a t-shirt, but no briefs, wanting to avoid putting unnecessary pressure on his behind.

That was pretty bad, Sam said, tossing and turning, struggling to get comfortable. I mean, I made an ass out of myself during the spanking.

Don’t stress, Glenn responded, realizing he held the guy’s self-confidence in his hands. It was your first time. You should have seen how I reacted back in the day when my dad spanked me.

Really? Sam asked.

Yeah, Glenn responded. I carried on worse than you did. Basically all guys cry and beg when they’re getting a real spanking. Most guys wouldn’t have had the balls, though, to go through with it like you did. You shouldn’t sell yourself short.

It just hurt so much worse than I ever expected, Sam admitted. I mean, I buy and sell companies for a living and couldn’t even take a spanking.

But did you enjoy it? Glenn asked.

It sucked nuts in the moment, Sam said, pausing to choose his next words carefully. But my dick is still rock hard. You were right about one thing—the plan was to go home and rub one out as soon as we were done.

Look, totally your call, but it’s not like I’m gonna stop you, if that’s what you want to do, Glenn said.

Just a few hours earlier, it would have been inconceivable to Sam that he’d jerk off in front of a gay dude, but after all he’d been through with Glenn, it didn’t seem that weird. Glenn had seen Sam’s bare ass and junk already, likely his asshole as well, as he struggled through the worst of the hairbrush, and he’d seen Sam crying. So what if he saw Sam jerk off too?

Here, let me get you some lube, Glenn offered, reaching into his nightstand.

In the meantime, Sam gingerly turned over onto his back, tossing his undershirt aside. With the air conditioner next to the bed, the sheets felt pleasantly cool on his backside.

If it helps, you can pretend I’m some slutty sorority chick in bed with you, Glenn laughed, passing Sam the lube in the nearly dark apartment.

Sam greased up his hands and went to work, reliving all the details of the spanking, made all the more vivid by the pain of resting on his blistered ass.

Uh, yeah, fuck man, Sam moaned, loving the feeling of his fist wrapped around his dick.

Taking it all in, this hot straight banker that he’d just spanked, pounding his own cock just inches away from him, it was hard for Glenn to stay on the sidelines. Wanna helping hand, guy?

Sam didn’t say no, which Glenn knew meant yes.

Glenn drenched his hands in lube and started spanking Sam’s monkey. It was not the first time he’d given a guy a hand job after a spanking, but it was maybe the most memorable time.

Immediately, Sam could feel the difference getting a hand job from a guy versus a girl. Glenn’s hands were strong and he knew what he was doing, pumping Sam’s dick up and down with seemingly endless endurance, alternating long strokes, with the occasional rubbing and pulling on the head of Sam’s cock. No girl Sam had ever been with before had that degree of skill.

Oh yeah! Keeping doing that! Fuck man! Sam cried out.

As Glenn had him raising towards an enormous orgasm, Sam fixated what it would be like going to work the next day with a spanked butt, the feeling of sitting at his desk for upwards of 12 hours working on his presentation, seeing guys like Cullen around the office knowing that only a few layers of fabric separated Cullen from Sam’s red behind, and doing lunch with Chad at Bulls, trying to pretend that everything was normal, and he hadn’t, just the night before, had the craziest, sexiest, and wildest experience of his life.

I’m getting close! Sam warned.

Let’s see what you’ve learned, Glenn grinned mischievously. I’m gonna keep going, except you don’t have permission to come. If you bust I’m gonna spank you again!

Hey, no fair! Sam yelled out, trying to pull back just as he reached the point of no return.

The spanking threat proved too much. Sam exploded all over his bare chest, shooting long strings of jizz, as high up as his shoulder.

Oh my god! Uh uh uh! Yeah! Yeah Yeah!!!!!!!! Sam yelled.

Glenn kept pumping until he was sure he’d gotten all the come out of Sam. I knew you’d be a shooter.

You weren’t serious about another spanking, right? Sam asked cautiously, beginning to come down off his post-orgasm high and using his undershirt to clean-up a bit.

You’ll just have to come back and see, Glenn responded, figuring Sam needed him, just as much as he needed Sam.

Deciding to take another chance, Glenn spooned Sam, the first time Sam had ever been held like that by another guy. Spent, the two boys fell asleep together in each other’s arms.

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