Phil's Annual Pride Pool Party

Jack's in a thong. De'on's in charge. Timmy's making a mess of the drinks. The old gays are admiring the hot young gays. Everything is unfolding as it should at Phil's.

It was when Jack dropped his jeans and was standing there in nothing but a thong that Phil did his third double-take in half an hour. 

First Phil saw Jack drinking an umbrella drink, then holding hands with his boyfriend De'on. No reason at all that Jack shouldn't be doing either thing. And Jack certainly looked happy, and seemed to be having fun. It was just that Phil had never seen Jack do either of these very ordinary things before.

As for the thong, Phil had seen Jack's prize-winning ass many times before. He might have even joked about seeing it naked as much as clothed. But Jack's standard underwear was a jockstrap, and Phil would have bet money that Jack didn't even own a thong, much less that he would wear one in public.

Now if a man wanted to get his cheeks out, Phil's annual Pride pool party was a great place to do it. Lots of guys had done that over the years, although it was usually the ones you kinda wish wouldn't.  Jack on the other hand not only could carry it off, but you wouldn’t be surprised if someone had begged him to do it. Jack's ass could stop traffic. But still the number one question in Phil’s mind was, why was he wearing a thong?  

Was it that the usual showing of ‘Jack in a Jock’ had become such a tried and true, expected thing that he felt the need to switch it up? 

Phil would discover soon enough that Jack was wearing the thong at the party simply because his boyfriend De’on had told him to. Not asked him to. Told him to.  And that would surprise Phil even more than the thong itself.

Thongs are very different things than jockstraps, but a guy probably won’t realize the depth of that until he goes to wear one of them and then the other.  Jockstraps are a hypermasculinized, but ridiculously sexualized symbol associated with some sports.  Jock is of course an abbreviation for jockstrap but also a very masculine athlete.  Footballers are jocks, as are hockey players, but no one calls a badminton player a jock.

And yet it’s impossible to picture an athlete in a jock without seeing it as inherently sexual.  The original intent of a jockstrap was protection of the genitals while holding them in place for “bicycle jockeys” in the 1870s, but the fact that design left the ass open meant it was always going to provide the casual viewer with thoughts of easy access to the butthole. Popularity with gay men was never going to be far behind.

A thong, on the other hand, conjures up a whole different reaction. It suggests ballet dancers and effeminate men (despite ballet dancers being every bit as fit and strong as athletes) and now the anus is covered.  Gone is the implied invitation for easy penetration. But so too, ironically, is the association with masculinity and sports.  

If two men stand side by side at an underwear party, one in a thong and the other in a jock, Thong Guy is going to be stereotyped as a bottom, and likely as submissive, whereas Jock Guy will be seen as more masculine, but, well, okay, also as a bottom.

Jack wore jocks not just because they looked really good on him, but also because they reflected the way he wanted other men to view him. And he didn’t own a thong for exactly the same reason, because up until this point he hadn't wanted to be stereotyped as that kind of bottom. Which is what made the very act of Jack wearing the thong so interesting. De’on had instructed Jack to go out and buy a thong swimsuit, and wear it to the pool party, because he wanted to draw Jack out of his comfort zone.  He wanted to see if Jack could enjoy being seen that way in public, and rightly guessed that he would never do it of his own accord. The last part of the gamble was to see if Jack would thank De’on for bringing him to this point, standing in Phil’s back yard, stopping conversation, and turning heads. He did.

It must also be said that De’on wasn’t doing this only for Jack’s benefit.  De'on definitely had some selfish reasons of his own.  He wanted every man at that party to see his boyfriend’s ass, and be reminded that he owned it, and no one else was getting it.  Jack’s ass was Dee’s to fuck, and Dee’s alone.  He wanted everyone to understand that, but also to be jealous.  He could have demonstrated ownership in other ways that didn’t sexualize Jack so overtly, so it was deliberate to display Jack’s ass this way.  He knew that displaying Jack in his usual jockstrap wouldn’t get much attention.  Everyone at that party would have seen that before.  But Jack in a thong was a beautiful new thing that was also provocative and titillating.  

When Jack and De’on got to the bar they discovered that Phil had hired Timmy and his boyfriend Thom as bartenders and dressed them in bow ties, speedos and not much else. Jack wasn’t thrilled to see one of Dee’s previous fucktoys there, but to his credit De’on didn't flirt with Timmy in the slightest and just asked him for two mojitos. 

It was quickly apparent that Timmy's only previous experience with the role of bartender was sucking them off in return for free drinks. Apparently Phil wasn’t familiar with Timmy’s infamous, drunken summer in Provincetown when he never paid for a single drink while earning the unofficial title of Eastern Massachusetts’ Most Accomplished Cocksucker. Mind you, Phil probably still would have hired him anyway, just for the decor aspect. 

So De’on took charge of the clusterfuck unfolding with the drinks and gave Timmy a tutorial on how to muddle mint and make a mojito. Suddenly there was a line-up of thirsty gays wanting mojitos but right at that moment a new ‘Hot Young Gay’, Ken, walked onto the pool deck.  He was Phil’s latest “discovery”. 21 years old, new in town and therefore very new to this crowd, and wearing ass-less briefs and what might have been one of his dad’s business shirts, unbuttoned and hanging off his shoulders.

Perennial party guest Ralph turned to his long-suffering boyfriend Brent and asked if he thought Ken was perhaps supposed to be some sort of cross between Tom Cruise in Risky Business, and Julia Roberts in one of Richard Gere’s shirts, but Brent was too young to have any clue what Ralph was talking about.

Ken’s entrance gave Jack and De’on the perfect opportunity to slip away from the bar and have their cocktails by the pool.

Jack definitely didn't want to raise the topic of Dee’s history with Timmy, but his mind kept going back to just how many sex stories he had shared with De’on in the Uber ride over. 

“Do you mind that I can be a bit of a slut?” Jack asked.

“Mind? No. It's what attracted me to you,” said De'on with a laugh.  “Surely you haven’t forgotten how we met?”

“Oh trust me, I remember.  I still visit that bathroom stall every time I change planes in Denver.”

The lads had met close to a year ago. They locked eyes as they were walking towards each other in DEN and the mutual interest was instantaneous. Minutes later Jack was perched on a toilet seat with his pants pulled down and Dee’s tongue was deep in his hole. Dee rimmed him like nobody's business for 15 minutes, and kept on going right through a text to Jack from Phil reminding him that the guy he was on his way to meet in Baltimore was going to try to kiss his ass to get a better deal. “He's welcome to take a number” was Jack’s enigmatic reply.  De’on only stopped eating Jack’s ass when he got an alert on his phone that his departure gate had changed. They pissed together into the bowl, crossing swords, so to speak, before heading off to their separate flights.

It was a month before they managed a second hook-up, this time at a hotel in Chicago. They fucked so long and so hard for three days that they missed the show Dee had booked, and a dinner Jack's friends. At one point they sent the concierge up to North Halsted to buy Dee’s favourite lube. 

“I wanted your ass from the moment I saw it,” said Dee, “and dreamed I was fucking you every night.”

“But why wait for my ass, when you could have guys like Timmy any time you wanted?” Jack cringed slightly that he hadn't been able to stop himself from mentioning his nemesis. 

“I didn't know it for sure until Chicago, but it's just different with you.”

Jack flushed, and thought he felt some precum work its way towards the tip of his cock. 

“But trust me, I was making do with Timmy and others in the meantime,” De’on continued.  Not for the first time De’on explained that although he thoroughly enjoyed fucking Timmy, the connection with Jack was somehow just deeper.  

Jack had never once asked De’on to change how he was fucking. He never once refused him. Never once made it about himself. De’on could pick him up, toss him around and every time Jack just played the role of lover perfectly. And De’on could literally feel himself get calmer the moment Jack walked into the room, which was something he'd never experienced with anyone else before. 

De’on was really used to guys expecting him to take charge, but most guys would also expect him to do what they wanted him to do, by somehow reading their minds. Jack not only let De’on call the shots, he also made it really clear that he loved every decision De’on was making. It was like they were two separate men having one single sexual experience. 

They had finished their mojitos, and Jack's mind was wandering to thoughts of how much he could read Dee's feelings, and how the two of them were quickly becoming connected. But no sooner had that thought formed when De’on effortlessly scooped Jack up in his arms, walked over the pool, and dropped him in.  Almost casually, like he was discarding him.  And then, in a voice that was slightly louder than strictly necessary, said “Stay there until I come get you”, and threw him an inflatable unicorn.

The reactions from the men around the pool were fast but varied.  There were definitely a few who clutched their pearls.

“Did I just hear what I thought I heard,” said Ralph, with an undertone of faux horror.

“How come you don’t ever do that to me?” Korean Sam asked White Sam. 

“Dream on,” replied White Sam.

More than a few guys turned to their friends and said they needed a man who could lift them up so easily.

And at least three very different men, scattered in and around the pool, suddenly realized that they definitely wanted to be treated exactly like that, and especially publicly.

Jack climbed onto the inflatable and De'on wandered off in the direction of the bar.  A lot of different thoughts and emotions were suddenly swirling through Jack's brain. He hadn’t seen it coming, De’on dropping him in the pool. It had totally caught him by surprise. And yet he wasn't angry. He felt quite happy to float there in the pool, and wait for De’on to come back, because he felt completely confident that De’on was in fact going to do just that.  It wasn’t logical. It was entirely just a feeling of trust. Even Ralph could see that this was sort of like a contented dog, waiting patiently and calmly on the sidewalk, while its owner went into a store for 10 minutes.

While Jack was sorting all this out in his mind, he saw a curious sequence of events unfolding. From where he was floating in the pool he could see a garden shed, down at the back of the yard. He only noticed it because he saw Timmy going in, holding a crate of empty bottles, but then nothing for 10 minutes when it was someone else who came out. Jack thought it was Thom, but then realized this guy was a little younger, a little taller, and a little more muscular than Thom. A minute later Timmy came out, tying his swimsuit. 

Soon De'on was back, wading through the pool towards him, holding two new mojitos. Jack took a sip and commented that Timmy seemed to be getting the hang of mixing drinks. 

“Oh no,” said Dee, “Timmy’s disappeared. Thom made these.”

“Does Thom have a lookalike here at the party?”

“Do you mean Peter, his brother?”

“Ah! Man, that could make for a sexy threesome.”

“I'm pretty sure Peter's straight.”

“I wouldn't be so sure about that, “ said Jack.

As much fun as the party was, both Jack and De’on were horny and just by looking into each others eyes realized they wanted to go home and fuck. 

“Climb on board,” said De’on, and he dropped down a bit in the water.

Jack slid off the unicorn, wrapped his arms around Dee’s neck and hooked his legs around his waist and into Dee’s arms.

De’on started walking to the shallow end. Apparently it made sense to him to carry Jack out of the pool on his back as a sort of closure on throwing him into the pool, and Jack just went along for the ride. Literally.

They were almost out of the pool when they met Peter coming in.  He was even more handsome up close Jack thought, and was really packing a punch in his shorts.  The three of them stood waist deep in the pool and chatted for a minute.  The water lapped above and below Peter and Dee’s crotches in a way that just served to accentuate their bulges.  And likewise the fluctuating waterline rode up and down Jack’s crack for those men lucky enough to be watching from behind.

“What I would give to bury my face in those cheeks for half an hour,” said Ralph.

“You wouldn’t get within five feet,” observed Brent.  “And if somehow you did, De’on would hold you underwater with one foot on your neck, like a kangaroo drowning a dingo.”“Oddly specific,” said Ralph.

“Saw it in a documentary once,” said Brent.

Jack and De’on made the rounds of the usual suspects and of course thanked Phil profusely.  Jack made lunch plans with Phil for Wednesday, to debrief on all the tea, and then they headed out to the front yard.

Their Uber was a minute away when Peter came out of the front door, and asked about sharing a ride. 

“I was supposed to head home with Thom and Timmy, but they're having a bit of a fight, and Timmy is a little drunk,” said Peter. 

“We're heading north, if that helps,” said De’on. 

Jack sat in the middle of the back seat of the now too small Hyundai Elantra, wedged between the shoulders and thighs of these two muscular men. Neither of them needed to ask if he minded. 

And rather than ask about the actual address or neighborhood the Uber was taking them to, Peter instead asked Jack: “How's that thong feeling up the crack of your ass?”

Jack turned to De’on, and realized that he knew exactly what Dee was thinking. Feeling Dee’s feelings was back. He wasn’t going to be surprised at what happened next.

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