The Boardroom

Tie Lessons

I was adjusting to being fully single again. I hadn't wasted time dropping hunky Wall Street-bro Kyle a message, and Kyle hadn't wasted any time hitting me back. 

Our first hookup was almost as hot as the Boardroom gang bang when we'd first met. We were barely in the hallway of my condo when we started making out passionately, gripping each other's bodies through our work suits. Kyle was a little tipsy from his happy hour, I was a lot horned up from a long, tough work day. I think I even let out a "fuck yes," as the 26-year-old's strong hand reached down and started undoing my zipper. 

"Fuck, I remember this cock, all right..." he hissed. "Fucked me three times at that party."

My mouth met his and our tongues dueled. I reached back to grip his strong gym-built asscheeks through his suit trousers. Kyle's suit was standard Brooks Brothers, and his shirt/tie combination was pretty boring. But the clothes wasn't this banker guy's big appeal. No, it was the way Kyle embodied every bit of hotness you see in guys around the Financial District. Ex-frat, probably ex-private school, ex-jock... he was the real deal.

Only his love of dick separated him from the stereotype. He playfully reached in his inner jacket pocket and pulled out a packet of lube. "Fuck me right here," he growled.

"Yeah?" I asked, getting very excited for just that. Normally with a guy I like to take my time and just enjoy the suit. But this was a different vibe we had. I took the packet and tore it open with my teeth as I watched Kyle get a big grin on his cute blond face and reach down to undo his belt and trousers.

He gave me a quick peck before turning around to face the wall. The trousers and briefs pushed down and I saw a prize winning ass. Actually, Kyle gave Ethan a run for his money there. 

I did a two-minute sprint on his tail and unloaded in his tight ass, just a few seconds before he started his cum.

He cleaned up afterwards and I did my best to compose myself, but it was clear this was a quickie and that Kyle was heading out to join his friends for dinner. Like so many professional New Yorkers that age, the dude loved to burn the candle at both ends.

It was the two weeks before I had a chance to meet up with Kyle again. I'd maybe pestered him a little to see if we could meet. I just couldn't stop thinking about his ass. After a few texts on my part, he'd offered to meet up for happy hour and suggested a downtown bar that's one of those long-running New York pubs that mostly served as a watering hole for bankers after work. 

Kyle was in business casual that day. Even if his suits weren't the most interesting, I missed seeing him all Brooks Brothers-ed up. But he did look plenty fine in his polo shirt and trousers. Like a lot of guys his age, Kyle Howard spent a lot of time at the gym. It paid off, with thick muscle, a trim midsection, and lots of definition. 

He knew it too. As he ordered us a round, I watched as he flirted with the girls who were gathered near one of the high tops. He was practically strutting as he brought our beers back to where I was sitting.

"I almost thought you were gonna pick up one of those women," I said, playfully.

He smiled. "I would, man. Only I got a date tonight."

I laughed. "Is that right? What do we got planned?" Being single could suck sometimes, but I did love this part of it. The flirtation, the hunt.

At least I thought I did. Kyle got a serious expression. "Dude, I'm not talking about us. I have a real date, with a woman."

"Oh," I said, caught off guard. "I guess I shouldn't be making assumptions." I racked my brain to figure out how and when I'd misread the signals. He'd been the one to give me his number, and, I mean, the guy was a cock whore that first party I'd met him. I was reconciling that Kyle with this one.

He shrugged. "I guess I could have been clearer. But, yeah, I don't date guys."

"That's cool," I lied. I had no real reason to be upset at Kyle, not really. But something about his personality - cocky, a little douchy - now rubbed me the wrong way. 

He took a sip of beer and looked at me steadily. "And don't take this the wrong way, but if I did go with a guy, you're kind of old for me."

"You weren't saying that when I was nailing you the other week," I shot back in a deep whisper.

He grinned. "Touché." He added, "Look, man, I wasn't hoping for any fucking drama. I just enjoy sex. I thought you gay dudes got that."

"OK, no drama, no hard feelings," I said. 

"You leaving?" he asked.

"Not until I finish my beer," I said. I had thought of walking out, but I didn't want to give Kyle any satisfaction.

We actually managed to have a decent, civil conversation. But I had nothing in common with this guy and held a lingering anger at his attitude. Maybe we could hook up in the future, though at that point I didn't want even that. 

Kyle finished his beer first and set down his glass. "I'm gonna go, all right?" Not apologetic in tone, but a little friendlier then he had been.

"Yep, sure," I said. 

Kyle left and I pulled out my phone. I'd been using the hookup apps more. I was still in my feeling things out phase, though. I hadn't had a lot of luck before, in part because guys on there didn't have the patience for the suit fetish. They'd be all into a suit and tie man, but would usually just want you to fuck them naked, not dress up themselves.  

But a guy caught my eye. 26, cute as fuck, smaller build but an amazing ass, best of all his pictures led me to believe he worked in the financial district. The fact he was currently logged in a block away confirmed that guess.

I messaged him. He messaged back. A few messages back and forth and he asked what I was doing.

"Just wrapping up happy hour with some workmates," I fibbed. I named the bar.

"Want me to join you?"

I did, and told him so. 

In person he was even cute, and his body was more of a normal body, the kind of 20-something body you get when you work long hours at a desk job but also fit time at the gym. I was into it, but especially his suit. Charcoal, off the rack, had an Ivy-preppy J. Press look to it. 

"I'm Neil," he greeted, shaking my hand as he walked in. 

"Bill," I said. "You had perfect timing. My workmates just left."

"Can't have you all on your lonesome, can we?" God, his personality was 180 degrees different than Kyle's. 

"Nope," I said. "Let me get you a drink. What'll you have?"

"Vodka soda," he said. "With lime."

I nodded and went to get a vodka soda and a G&T. We toasted each other and took a sip. 

"Not out with friends?" I asked. 

He shook his head. "Should I be?"

"Not necessarily," I replied. "But it's summer, nice weather, and most guys in their 20s are hanging out with their buddies."

"Sometimes I prefer older guys," he answered with a blush. 

"You won't get any argument from me," I said. I thought about what Kyle had said. Maybe guys like him and Neil were too young for me, or I was too old for them. I'd have to figure out what I really wanted, but that could wait. I had a cute Wall Street guy giving me heavy, flirty eye contact as we chatted.

"So..." Neil said. "Your profile says you're into suits."

"Very much so," I replied. "Is that your thing?"

"I'm still trying to figure out 'my thing,'" he said, honestly. "But guys in suits are hot... especially if they're older."

"It's more of a daddy thing for you," I observed. Neil wasn't the first young guy I'd met like that. Even a number of man my age, or close, loved for me to play daddy and the suit was part of that appeal for them.

"Totally," he said. "I was surprised when you messaged me, because you're kind of my perfect Daddy."

He was forward, maybe too forward, but after douchy Kyle I was into it. "What do you think of going back to my place?" I asked. "I could be as much a Daddy for you as you like." If the fish is biting, why not reel it in? 

"I'd definitely like that," he grinned. 

As we made our way back to my place, I was able to size him up even better in the full daylight. 6-foot-even, nice build, dark hair, dark complected. Amazing ass filling out his suit. Yeah, I'd happily play Daddy for this young dude.

I thought we might launch right into it but Neil stepped up and ran his fingers along my lapel. "What do you think of showing me?" he asked. 

"Showing you what?" I was getting hard anticipating fucking this guy. Or at least getting a nice blow job.

"The suit thing. You know, like you mentioned in the profile."

I smiled. "I can definitely do that," I said, happy he was open to this. "All right... First, you want to feel up a man's suit. Kind of like you're doing. Start at the suit coat. You can feel the construction right off in the lapel and just beyond that the canvassing."

He grinned, like he was kind of amused but he nodded and took in my words. His hands took the suggestion too, and started exploring the fabric, cut, and construction of my suit coat. It was simple but erotic as hell. At least for me, but Neil seemed to be getting into it.

"OK, now," I instructed, "run your hands beneath and feel my shirt."

"Wow, you're built," he smiled. "Kind of better than your pictures."

"I'll have to thank my personal trainer," I winked, getting off on Neil's fingers running along my obliques and up to my chest. "My shirts are tailored and you're enjoying the fit, the way the cotton molds to my body, but not too tightly." I was getting off on verbalizing for Neil. 

"Nice," he hissed. Yeah, maybe it was more my teaching him, but he was getting into it. 

"It's not some Clark Kent poured-on look, either. Just how a man's shirt should fit. It should accentuate his body but not be obscene."

He nodded. 

"Ready for the best part?" I asked.

"Your cock?" he teased.

"Well, second best part," I smiled, reaching up to run my hand along his tie. It was fine, a repp tie of medium quality. Probably Brooks Brothers. Neil had a good eye for colors that showed off well with his complexion. I carefully unknotted it and held the two loose ends in my hand. 

"A tie is what makes a man," I said, "Let me get you a better one." I gave a gentle tug at his tie to pull the young guy toward me. "Come, follow me."

He seemed to enjoy the playful spirit I was indulging and followed me to my walk in closet.

"Whoa," he said as I turned on the light and he saw the neatly lined suits, the pressed dress shirts, the folded sweaters and the shelves of shoes. In the grand scheme of things it wasn't an outrageously large closet, but by New York standards, it must have seemed imperial. 

I was hard. Turned on to show this younger guy the pleasure I got out of my clothing and happy to see it reflected back to me. I picked a tie out and offered it to him. He immediately started tying a four in hand.

"Nope," I interjected, taking the tie ends from his hands. "Didn't your Daddy tell you how to tie a tie? An up and coming man like you needs a half windsor. A man's knot."

I could practically hear him gulp in excitement as I walked behind him, looking over his shoulder at his reflection in the full-length mirror. I tied a perfect knot for him, and was immediately rewarded to see how much it upgraded the standard issue suit. 

I patted his suit jacket shoulder, which had a nice roll to it, not too much padding or construction. "See? You look hot as fuck now."

"Yeah, Daddy, it's wild," he admitted. He smiled, seemingly a little embarrassed for getting into his reflection. 

I pulled out a pocket square. Neil wasn't wearing one before. He was now, a nice paisley one that set off his tie color and his brown eyes. I patted his suit front to straight out the way it lay on his trim but built body. 

"Just enjoy this, son," I said and crouched down in front of him. I could have easily had this young dude service me, and service me without recip. But I wanted to give him the pleasure of cumming in his suit. Of getting into the scene. 

I took my time massaging his erection through his trousers. Neil was excited as he alternated looking down at me and back up at his reflection, which showed me, an older more accomplished man, kneeling at his crotch. 

I unzipped him and reached in. His dick was nice and hard, like a 26 year old's cock often is. I got the feeling he could go a couple of times in a go, but even if we weren't going to do that, I was going to enjoy the firmness and the readiness of a young cock in my mouth. 

He hissed as I took him in my mouth. I didn't hold back. As soon as I got worked up to the length in my throat I bobbed up and down steadily, going for a full on blowjob. 

"Fuck yes, suck me Daddy," Neil grunted as his hands reached down to touch and grip my suited shoulders. I didn't have to look up to know he was watching the scene in the mirror reflection. Enjoying getting head from a well-dressed businessman, maybe the kind of finance guy he'd fantasized about before. 

He didn't have to fantasize now. I was practically sucking the cum out of his horny balls. Neil held on tighter for balance and growled in choked cries that mirrored the spasmodic spurts of his semen down my throat. 

I nursed the last bit out and gave one last kiss to his dick before standing up, unzipping as I did.

I didn't have to ask pretty please. Neil was now crouching in front of me, ready to return the favor. Sometimes guys like Neil - young, eager, impetuous - aren't good at giving head, but I was surprised at how good his mouth felt. Not Ethan skills but respectable. I put my hands in my pockets and looked down on him. With my tie and pocket square and his J. Press charcoal suit. 

I came. 

Neil swallowed my seed and took even more time and care nursing my dribbles. I finally pulled out of his mouth and made a show of tucking back into my suit and zipping up.

"I didn't expect I was going to get such a treat on a Tuesday," I said as I helped him up. 

"Me either," Neil said with a sheepish smile as we met in a soft kiss. "Thanks." As he undid my tie and removed the pocket square, he gave me another aw-shucks look before adding. "I should get going actually."

This was going to be a one-off thing. Fine with me. Thought a part of me hoped I'd shown Neil the excitement of suit play. 

He used the restroom, then I showed him out. 

Afterwards, I was in a good mood. Happy but somewhat contemplative. What was I doing chasing younger guys? I knew I wasn't ready for anything serious at the moment, but as I watched a recent movie on TV, I made a few resolutions: I'd cut back on the hookup apps for a while. Not for good, but I wanted to spend more time getting my act together. I felt like I had to figure out how important the suits were to my sex life, or if I could have something normal with a guy who didn't share my fetish. Not that I felt ashamed of my desires, but it made the numbers game of finding Mr. Right that much harder.

I wanted to focus on my fitness, for health and for my appearance. Maybe my suits were keeping me from having the body I wanted for myself. I'd have to be more careful with my diet and more dedicated at the gym. 

I don't know if it was Neil inspiring me, or Kyle shaming me. Or feeling not great with how it all played out with Ethan. But I didn't want to coast along like I had the last couple of years.

HAPPY HOUR

"You seeing anyone, Bill?" 

Tom Stephenson and I were having drinks before dinner at a Lower East Side restaurant-bar one January evening after work. We had became good friends and had a standing happy hour or dinner appointment every other Thursday. We had the suits in common, of course, as well as very similar jobs in finance. Of all the guys from the Boardroom, Tom and Ethan were the one I bonded with outside of the suitsex parties.

"Nah," I said. I had mostly kept to my pledge to stay off the hookup apps. I had caved one lonely night over Christmas holidays, and I first wondered if I was being silly, but an evening of hot sex ended up with a very awkward conversation when I asked the guy for a possible date. "Still a confirmed bachelor," I laughed. 

He smiled and had a sip from his martini. "Not to bring up a sore subject, but I kind of thought you and Ethan would become serious."

"Not in the cards," I said. "I still don't know if I made the right decision, but we're getting along better as friends."

Indeed, my ex-boyfriend and I had gotten along real well since breaking up. I'd upped my training sessions with him, and our extra time in the gym gave us plenty of time to bond. We hung out occasionally, too, as friends. 

"How's that working out?" Tom asked. "Having your ex be your personal trainer?"

"Good. We keep our boundaries," I said. Neither Ethan or I talked about our dating or sex lives, beyond general conversation about the Boardroom meetings. "We've kind of made a tacit agreement not to attend the same Boardroom meeting."

"Probably for the best," Tom said.

"How about you and Mike?" I asked. Tom had been dating Mike from the Boardroom parties, for several months now, and from what he described their dating was getting more serious. "You go to the same ones. Is that weird?"

He shook his head. "We got a very open arrangement, it works out." He took a sip from his drink and added jokingly. "Some months it feels like I only see him at the Boardroom. Don't date a doctor, Bill," he chuckled. Tom wasn't model-esque but had an ordinary WASP-y handsomeness that grew on you. "They got worse work schedules than us finance guys."

"Is everything going all right, though?" I asked.

Tom smiled. "Yeah, great. I'm just bitching." He paused, as if he wasn't sure he should share about what he was going to share. "The best part of dating a doctor is he's open to doing a doctor scene."

I wasn't sure what Tom was getting at. But then it occurred to me. "You mean....?"

My friend nodded. "White coat, stethoscope, annual physical, the whole works."

My cock chubbed a little. It was like the suit thing but in a different way, with more of a porn-y narrative to it. "Sounds pretty wild."

"Oh yeah it is. Mike's amazing at it, too. Stays in character, and of course is a real doctor."

I didn't even realize I had a big doctor fetish until that point, but I could imagine it. And the exciting part was that I didn't even know exactly how such a scene would play out. "I hope I'm not prying... but how often you guys do that?"

Tom leaned back, and I could tell he was firm in his suit trousers. "About once a month. Usually at home, but once I visit him at his office. That was incredible."

"Wow," I said. 

He gave me a careful look. "If you want, I could see if he'd do it for you. I know he finds you hot, Bill."

I had fucked Mike at one of our Boardroom parties. It wouldn't be the first time we'd had sex. But this felt different, like a friend sharing his boyfriend with me. 

"I wouldn't want to edge in on your guy," I said, but I had to admit the idea sounded real appealing. I'm sure Tom could read my interest in my eyes and in my voice.

He gave me a pat on the back. "Fer Christsake Bill, you're not going on a date with him. And it's not like we haven't sucked each other's cock, either."

"We probably will again, too, I'm sure," I said. "If we keep going to the Boardroom parties." I sometimes thought I should adopt some of Tom's more liberated spirit when it came to sex and dating, though I'm not sure I could be so open. But Tom Stephenson had a way of rubbing off on me. 

"Speaking of which..." he said with an impish look in his eyes. "Mike's busy, and I have no plans tonight.... seems a shame to put this suit to waste." He gestured down at the tailored navy suit he was wearing. 

I felt my cock grow hard. Tom was a friend and there was no sexual tension between us, but I'd not gotten laid nearly enough lately and a 69 or a BJ swap sounded pretty good right then. "Yes, it does," I grinned, reaching over to run my fingers along the soft wool fabric. Tom's body was neither super-fit nor average, but somewhere in between. Kind of what mine used to be before Ethan started whipping me in to shape. 

Tom chuckled, a little pleased to see me let my hair down some. 

***

Back at Tom's place we took it slow. Feeling up the fabric of our suits. It might be friend/fuck-buddy sex but the advantage was that Tom and I shared the fetish and knew how to explore it. Verbally, tactilely. We didn't even kiss, it was just about our mutual admiration for our clothing. 

The best part was that we didn't rush to pull out our dicks. We felt up the suited hardons, massaging each other's crotch and displaying our clothed erections for one another as we talked about our next suit purchase we wanted to make. 

"I have a work trip to London coming up," I said. "I'm thinking of getting a nice pinstripe, and some new shoes."

"I'm trying to picture you in pinstripe," he said. "I bet you look great."

"I have a Zegna navy pinstripe suit I bought when I was in my label whore phase. Kind of 90s in cut, and I rarely wear it but still looks all right."

"You should wear it to the Boardroom one time."

"Vintage night?" I smiled.

"Haven't had one of those in a while, but those are fun."

"Yes they are."

"Speaking of label whore..." Tom started. "I've been eyeing up this Brioni. Slate blue, fine as fuck," he growled, spreading his thighs to let me see his hard tool ride up in his trousers.

I copied his actions. "Fucking nice," I said. "You're really gonna drop that kind of money?" We were talking about a six-thousand dollar price tag.

He grinned and shook his head. "Well, maybe I'll have my tailor copy it. He's pretty good."

"I can tell," I said. "As good as Capollini. I don't know if I told you, but I took Ethan there to get a fitting and dude didn't even bat an eye. He probably thinks I hired Ethan as a kept boy."

Tom laughed. "No offense, Bill, but given Ethan's body, I'd probably come to that conclusion, too."

"Fair," I smirked. "But I've been working on myself lately. Kind of one of my goals."

Tom looked me up and down. Maybe it was my horny state or our laidback mood but my friend was real attractive at that moment. "You're definitely filling out your suits real fucking well these days."

"Thanks, buddy. You're looking great too."

Tom was getting off on this one-on-one play. "Think you might want to suck my cock, Bill?" he asked groping his suit. 

I nodded and crossed over to kneel in front of him. He started to unzip but I stopped him. "Let me have some fun first, OK?" I asked.

Tom grinned. "Oh yeah, have at it. Get me leaking in my suit trousers, bud."

I did. Using my hands and my face. Forehead, cheek, nose and chin rubbing up against the ridge of his finance-guy erection in a very nice charcoal glen-plaid suit. Eventually I was kissing and sucking at his bone, while his own hands ran along every inch of my mid-gray suit that he could touch. 

"Can't take any more," he grunted and unzipped to pull out his dick. I took him into my mouth. 

I was trying not to fall into my selfish-top ways with men. To focus more on the mutual give and take, and reciprocation. That didn't mean bottoming but for oral, I was enjoying trading, or 69-ing. Tom was the perfect guy to do it with. 

As soon as he was getting close to cumming, he nudged me off. "Your turn," he gasped. 

I stood up and pulled out my own erection. This was something that suit guys know. The power of seeing a hard cock jutting out from a man's suit. No belt or fastener undone, just a rigid spike of meat bared on an otherwise fully clothed man. It's an incredible aphrodisiac. 

It drove Tom wild. He licked lewdly at my prick then started swallowing it. At first it was just regular head - great, awesome but not going to bring my off imminently. But soon I felt the switch click and my pleasure start to build up. I gave him a soft warning. 

Tom pulled off with a look of wild lust in his eyes. "Mind getting your suit a little dirty?" he asked. 

"What do you have in mind?" I asked. 

"Rub our cocks together and cum that way."

It sounded worth trying. We lay on his couch and made out, feeling each other's suit and thrusting our dicks against one another. If we weren't leaking so much pre-cum it might not have worked, but soon our rigid spiked butted slickly against one another and got extra stimulation from the suit fabric. 

That's what did it for me. I started spurting my semen all over Tom's cock and the crotch of his suit. 

"Fuck yes," he hissed in my kiss and his own dick sprayed against me. 

We were giggling a little as we came down from our orgasms and uncoupled. 

"Damn, I'm pretty soaked," I said. 

"You're soaked?" Tom laughed, pointing down to his suit crotch, which was very wet and dotted with heavy splotches of my cum. "How long has it been since you've been laid, Bill?"

"Too long," I admitted. 

Tom went and got some wet clothes to wipe down the wool fabric as well as possible. We'd still have to take our suits to the cleaners, but at least the danger of major stains was less. 

"Your overcoat should cover that," he said. 

I got dressed again and ready to step back out into the cold. I paused as Tom showed me out. "Thanks Tom, I think I needed that."

"I had a fun time, Bill. Talk to you later?"

"Yep," I said.