My Pleasure, pt. 1 (Patreon)

*** This was another story idea that came about when I was setting up the randomizer, with the topics being "sugar daddy" and "panties." Enjoy! ***

“Hey!  I’m glad you decided to come out, man.”

Ryan tried his best not to gawk at Wyatt’s bare, brawny frame, but it was a difficult task.  For starters, the dark-haired hulk filled the doorway.  At 6’4'' and nearly 300 pounds of shredded, bodybuilder bulk, the grinning giant took up space wherever he went.  With his imposing physique and sharp, handsome features, it was hard not to look at him under the best of circumstances.  Coupled with the fact that all his tanned, strapping frame wore at the moment was a pair of purple lace panties, it became an impossibility.  After an awkward silence the blushing brunette finally averted his eyes and shrugged, trying to make light of the fact that he’d just been staring at the other man’s girthy package.  “I mean…you make a hell of an argument,” he laughed.

Wyatt looked down at himself and mirrored the shrug.  “You honestly stop thinking about it at all after a while.  But we can talk about that…come in, come in!”

Ryan felt positively tiny as he was ushered past the towering hunk.  It wasn’t just that the other man stood at least six inches taller than himself, but because of what he stepped into.  From the outside, the house had already looked like a massive work of art with its sharp angles butting up against curved walls, and the interior was even more stunning.  Nestled into the foothills outside of town it was an Art Deco iceberg, spilling down the cliffside for several stories before terminating in a sprawling patio that overlooked the city off in the distance.  Where most houses entered on the ground level, Ryan found himself entering onto the top floor, his view through the wall of windows on the far side entirely unobscured by the open, sprawling space.

“Wow.  You, uh…you kind of undersold it,” he laughed, feeling almost dizzy as he took in the designer chairs and sofas.  The whole level was set up like a posh lounge, undoubtedly to take advantage of the impressive view while entertaining guests.  For someone currently living in an efficiency apartment the size of a walk-in closet, it was overwhelming.

Wyatt sauntered into the room and spread his arms wide, doing a slow turn to gesture at the opulent surroundings.  “A bit hard to describe though, right?”

Ryan’s eyes darted back and forth between Wyatt’s exposed, mammoth cheeks and the rest of the room.  The chiseled statue of a man appeared as confident and comfortable in his skimpy garb as when they’d talked in the locker room the day before.  It was a similar pair of conspicuous underwear that had caught Ryan’s attention in the first place.  When he’d seen him at his gym for the first time the previous week, he’d immediately noticed the newcomer’s shirtless, sculpted physique.  From an athletic perspective, the bigger man’s body was a work of art.  He bulged with precision-crafted muscle, his perfectly tanned, smooth skin stretched taut over equally perfect, proportional mass.  As someone who’d been lifting ever since he’d hit puberty a decade prior, Ryan had been captivated from the start, but the hook was truly set when he’d watched Wyatt on the squat rack.  The handsome giant dropped low, causing his tiny shorts to do the same, and that’s when he saw it: Burgundy lace.

At first Ryan wasn’t sure he’d actually seen what he’d thought, and he’d felt awkward as he’d kept stealing glances, but his suspicions were confirmed a short while later when they ran into each other in the locker room.  He’d stripped down to his own sweat-soaked boxer briefs and was about to peel out of them and head for the showers when he’d turned to see Wyatt standing in all his panty-clad glory.  He’d done a reflexive double-take, shocked that the mountain of a man would be so casually wearing women’s underwear in public, but a longer view of the stranger’s impressively hefty package made it clear that, while styled in a very feminine vein, the lace bottoms were actually cut for a man.  Wyatt had caught him staring, but all he’d done was smile and nod, the same thing that he did for the many confused looks aimed in his direction.

From the start, Ryan had been impressed by the handsome hulk’s unfazed demeanor.  He was the picture of confidence as he stripped down, showered, and donned a similarly slinky pair in turquoise, not putting anything else on until he’d gone through his entire grooming routine.  On the second day, after another exchange of silent glances, Wyatt had made a joke of it, putting Ryan immediately at ease with his easy-going attitude.  On the third day they’d spotted each other, and by the fourth they were hanging out on the floor like old friends.  Wyatt’s charm was magnetic, and Ryan was beginning to understand why people didn’t give him more of a hard time for his choice of attire.  It wasn’t just because he was the biggest, most hung guy in the locker room; it was because you didn’t actually want to.  His friendly, confident aura deescalated conflicts before they arose, his willingness to acknowledge the unusual nature of his appearance quickly taking the shock out of it.

By the fifth day, Ryan was unloading his worries on his new friend, opening up about his strapped finances and how he wasn’t going to be able to make rent this month.  All the well-paying jobs in the city were in the tech sector, and as a high school graduate with no further schooling or training, the most he’d been able to land were jobs waiting tables.  Ryan already had three of them, but with the cost of living getting higher by the day, he’d reached the point where it just wasn’t working.  He wouldn’t be able to afford the gym anymore either, and it was looking like he’d have to do what any 23 year old dreaded and move back home with his parents.

So when Wyatt offered up the possibility of an alternative, even one as embarrassing to contemplate as it was, Ryan didn’t immediately shoot it down.  His initial reaction was that he’d never be able to go through with it, but, after thinking about it for a couple days, and with the end of the month in sight, he told himself he had to at least look into it.

Wyatt, it turned out, had a sugar daddy.  The bigger man, who was himself only a few years older than Ryan, was able to maintain his impressive body because it was his only real job.  His wealthy patron threw money at him, provided anything he wanted, including a room in his luxurious estate and the six-figure car the handsome hulk drove, and all he had to do in return was wear the tantalizing underwear.  At home that was all he wore, but he could cover it up with more traditional clothing in public, unless they agreed otherwise.  Ryan appreciated that Wyatt was quick to point out that he and his sugar daddy did plenty of other things with each other, but that it hadn’t been the expectation at first.  After spending time together for a while Wyatt had wanted things to progress, and if Ryan decided to join them it would be with the same understanding.  Outside of a few basic rules, the athletic brunette wouldn’t be forced to do anything he didn’t want to.

Ryan thought he’d be able to go through with it.  He’d gassed himself up for the past few days by reminding himself that his own gym-built physique was superior to most, and that his charming, boy-next-face could hold its own.  He’d always been the hot jock, a pouty-lipped pretty-boy who could bat his brown eyes and get anyone to drop their pants.  But now that he was standing in a stranger’s house with a nearly naked man he’d only known for a week, with himself being the one about to drop his pants, he wasn’t sure.  “So do I get to meet your mystery man,” he asked.

Wyatt nodded and motioned for Ryan to follow him down the wide, spiral stairs.  “In a bit.  Leo’s got a work call right now, but he should be done within the hour.  He told me to give you the tour and get you situated while we wait.”

“Feels like we’ll need more than an hour for that.  This place is huge,” Ryan said as he stepped onto the lower floor.  “What does Leo do to pay for all this?”

“Honestly?  I don’t know all the details,” Wyatt shrugged.  “Something with technology and pharmaceuticals…he doesn’t like to talk about it a lot.  But it pays for all this,” he said, waving a muscled arm.  The stairs came to a broad, central landing peppered by a few chairs and a coffee table, with short hallways shooting off on either side.  Ryan didn’t know what to say as he took in the bedrooms, each of them legitimately bigger than his current apartment.  Leo’s suite was especially well-appointed, the attached bathroom in particular making the dazed brunette quiver with envy.  He had a dirty shower shared by three other apartments on his floor, which is why he primarily used the ones at the gym, so to see what was essentially a spa was almost more than he could imagine.

The thought that he could actually live in such a space was intoxicating, a sensation that only grew stronger as they continued their descent.  The third floor down was a more traditional living space, with a huge kitchen, fancy dining room, comfortable living room, and what Wyatt said was Leo’s office behind the closed door at the far end.  The bigger man explained that a staff of cooks and housekeepers came in every few days, which sent a stab of embarrassment through Ryan as he thought of himself lounging in the revealing underwear while they were around, but it was outweighed by the idea that he wouldn’t even have to cook or clean for himself.

The scales tipped back in humiliation’s favor when they reached the dance club that was the bottom level.  There was even a stage with a pole at one end, with a few raised platforms in between it and the bar at the opposite side of the room.  A cushioned bench the length of the space stretched along the back wall, below the mirrored upper half, with a few pub tables and stools scattered throughout.  But before Ryan could ask, he was led out to the sprawling patio with the huge, glistening pool, massive hot tub, and cabana the size of a small house.

“So what do you think,” Wyatt asked, pointing a thumb over his shoulder at the hazy skyline in the distance.  The view from the patio was just as impressive, overlooking the valley that grew increasingly populated as the ground leveled off.  “There’s a full gym and sauna in there too…nice than where we met, but I like to get out of the house every now and then.”

“It’s a lot to take in,” Ryan admitted. “I’m kind of spinning right now, man.  I mean, this place is wild.  I feel like I’m too poor to even be standing here.”

The tanned titan laughed and clapped the dazed jock on the shoulder.  “You look right at home to me,” he said before raising an eyebrow.  “Other than the outfit.  Come on…let’s get you set up.”  Ryan’s heart started racing as he followed Wyatt back up to the bedrooms.  He’d known this was coming, his new friend had told him it would be part of his “audition,” but this meant he’d officially reached the point where it all became real.

The nervous jock was just as impressed with Wyatt’s broad bedroom, complete with spacious King and amazing view, when they stepped inside, but his eyes immediately dropped to the small pile of pink satin resting at the foot of the bed.  “Oh boy,” Ryan laughed, helpless to keep his face from going crimson.  “Those are for me, huh?”

Wyatt grinned as he held up the revealing underwear.  The satin bottoms looked like little more than a scrap of fabric in his huge hand, the thin strings that tied at the sides mimicking the way Ryan felt inside as they dangled in the air.  “Leo picked them out himself.”

The blushing jock couldn’t help but appreciate the irony.  It was a style he loved on women, but not one that he’d ever imagined putting on.  He took a deep breath and plucked them from Wyatt’s hand, giving a short laugh when he turned towards the nearby bathroom.  “I almost went in there to change.  Kind of pointless though, isn’t it?”

“You’re more than welcome to if you want,” Wyatt nodded.  “But, uh, yeah.  It really is.”

“Might as well jump right into the deep end,” Ryan shrugged.  He tried to tell himself it was no different than the locker room as he peeled out of his tank top.  He and Wyatt had already seen each other naked several times in the brief period they’d known each other, and the smaller brunette had never been overly shy about his body.  With his broad shoulders, plump pecs, and tight, tapering washboard, he’d never had to be.  His skin was naturally smooth save for a light dusting in the expected spots, his arms were well-muscled and ready to flex at a moment’s notice, and his meaty thighs were big but not bulky, just like his perky, perfect cheeks.  And while his average cock wasn’t the imposing hose that Wyatt sported, the proportional equipment put a neat, fleshy bow on the impressive package that was Ryan’s athletic physique.

It also presented a rapidly growing problem.  When he’d shucked his shorts and reached his boxer-briefs, Ryan could already feel the eager organ threatening to twitch.  Between his overwhelmed brain, the novelty of the situation, and the proximity of Wyatt’s bare bulk, the flustered jock told himself it was a perfectly natural reaction.  Getting hard when stripping down in someone’s bedroom was normally exactly what he wanted to have happen, but now he did everything he could to keep a lid on his simmering arousal.  It was a tenuous seal at best as he stood naked and blushing beneath Wyatt’s steady gaze, and it was blown off entirely as soon as he slipped the smooth material between his hairy, muscled thighs.  His cock shot to attention the instant the pink satin made contact with his hefty balls, a sudden jolt shooting through him that made it impossible to tie the underwear in place.

“Well…shit,” the crimson-faced stud finally stammered.

“Don’t sweat it, bro.  That’s to be expected.  I take it as a good sign, really,” he said with a sympathetic smile.  “Let me guess…you’re thinking about all the times you’ve normally held something like that in your hands, right?”

Ryan flushed a deeper shade.  He actually hadn’t been thinking about it, but now that Wyatt mentioned it, his head immediately flashed back to all the times he’d stripped a pair of panties off a feminine partner.  Now, thinking about himself wearing them, his addled thoughts pulled that thread even further, inserting him in the position of the person he normally stripped them from.  He’d only ever worn boxers, boxer-briefs, or a jockstrap, and the latter only when absolutely necessary for athletics.  Now that he was faced with something totally new, it appeared that his body knew something he didn’t.  He couldn’t remember the last time he’d been so turned on.  “This is going to make things difficult.  Did this happen to you at first?”

Wyatt nodded.  “Still does.  It’s all part of the fun, right?  You want me to help you out with that?”

Ryan froze, knowing full well that he had a deer-in-headlights expression on his face.  “Uh…what?”

The dark-haired hulk let out a deep laugh as his smaller friend squirmed.  “Maybe I read it wrong?  I kind of got the vibe that you’d messed around with guys before.”

The blushing brunette couldn’t believe what he was hearing.  He actually had fooled around with men in the past, but only rarely, and he’d never talked about it with anyone.  Nor did he think he gave off even a remotely “gay” aura, so how the bigger man knew he had no idea.  Then again, Ryan was also aware that he was standing naked and hard in Wyatt’s bedroom, so it could have been more obvious than he realized.  “I mean, yeah, but not a lot.  I’m not…there’ve just been a few guys at the gym over the years who wanted to blow me and I let ‘em.”

“Well, I’d be happy to continue that tradition,” Wyatt purred, dropping to his knees.  When Ryan didn’t pull away he leaned in and swallowed nearly all of the shorter jock’s aching organ, his large hands latching onto the other man’s solid rear.

“Oh…oh fuuuuck,” Ryan moaned, his eyes wide as he gazed down at Wyatt’s broad, flexing shoulders.  When guys had blown him in the past he’d always closed his eyes and thought about the last girl he’d hooked up with, but something about the sight of the beautifully built, panty-clad stud on his knees was more of a turn on than any memory.  It also didn’t hurt that Wyatt was very good at the task at hand, his soft lips and strong, nimble tongue bringing Ryan to the edge, then backing off, again and again.  He could see his friend’s thick log had gone hard and had escaped from its lace prison, and for the first time ever he gave serious thought to what it would be like if their roles were reversed.  He imagined himself on his knees, his face buried between Wyatt’s thick thighs, the other man’s fat cock filling his mouth.  He surprisingly didn’t hate the idea, enjoying the fantasy so much that it shoved him over the edge.  With Wyatt’s strong hands holding his ass in place, Ryan whimpered and spasmed, helpless to do anything other than launch load after load down the kneeling muscle man's throat.  “Holy shit, bro,” he finally panted with a dazed laugh when Wyatt pulled his head away.  “That was amazing.”

The bigger man looked smug as he climbed to his feet, his imposing log pointing in Ryan’s direction.  “More where that came from if you decide to stick around,” he said, following the other man’s eyes to his rigid member.  “See something you like?”

“I, uh, I’ve never really…” Ryan stammered, his heart racing at the thought of actually playing out the recent fantasy.  “I feel like it’s rude to leave you hanging.”

“Ha!”  Wyatt gave another booming laugh and tousled Ryan’s hair.  “Tell you what, bud…you stick around and I’ll walk you through whatever it is you’re wanting to try.  But right now we should go find Leo…he’s probably done with his call.  Don’t worry about me, I’ll be fine.”

As he tied the pink satin bottoms into place, Ryan knew the decision had already been made.  The thought of going back to his closet-sized apartment and struggling month after month seemed like a nightmare when he could instead lounge in luxury with incredible blowjobs on demand.  Even the embarrassing underwear wasn’t as bad as he thought it would be.  Now that he had it on, the shiny fabric expertly hugged his package and accentuated his muscled bubble.  And whether it was due to the lingering body buzz of his recent release or the completely new situation, Ryan felt unburdened and borderline giddy in a way he hadn’t felt in years.  Following behind the scantily clad demigod as they made their way down a level, he felt special, as if the fact that he’d been chosen was an accomplishment.

Though to be fair, he also knew he hadn’t actually been chosen.  Not yet.  His heart started racing again as they descended the spiral stairs, this time from an entirely different kind of nervousness.  He didn’t want to blow it.  Now that he actually wanted to stick around, he felt a pressure that he hadn’t before, a pressure that weighed all the more heavily when he finally got a look at his would-be benefactor.

Leo wasn’t at all like he’d expected.  He thought he’d be meeting someone old, or unattractive, or mousy and insecure, but the wealthy man was none of those things.  He was gorgeous.  Even from across the room, Ryan could feel the confident masculinity radiating off the other man in waves.  He had the kind of presence that filled a room, and the kind of body to back it up.  While Leo did appear older, he looked as if he was just cresting into middle-age, with a fit, athletic frame.  He split the difference between the younger men, standing a few inches taller than Ryan and a few inches shorter than Wyatt, with a muscular build that straddled the same line.  Broad shoulders and prominent pecs stood out against his linen shirt, while well-developed arms spilled from the short sleeves.  Unlike the younger pair’s smooth skin, the exposed top of Leo’s chest was dusted with a wiry, golden carpet that matched the wavy hair on his head, adding to his masculine aura, and Ryan already found himself wondering about the details that lurked in the older man’s tight chinos.

“There you two are!  Good timing,” Leo said, his tone warm and cheerful.  He gave Wyatt a quick slap on the rear and a peck on the cheek, cocking his head and raising an eyebrow as he looked Ryan up and down.  “I’m Leo.”

“Ryan,” the younger jock said, taking the extended hand.  He was already afraid that Wyatt’s earlier assistance was going to go to waste as his stomach fluttered under Leo’s sparkling blue eyes.  The differences between them were overwhelming.  The older man’s wealth, his self-assured attitude, his clothes; Ryan suddenly felt insecure and ridiculous to be standing in nothing but a pair of pink panties in front of such a specimen.  Why that sensation turned him on, he had no idea.

“I trust Wyatt gave you the full tour?  What do you think of the place,” Leo asked, motioning for them to follow to the kitchen.

Ryan tried his best to sound casual.  “It’s incredible.  I didn’t even know houses like this existed.”

“I know, right?  I had the place built, and even I’m continually surprised by it.  Just wait til you see the sunset over the city out there.  It’s magnificent.  Can I get you anything?  Coffee?  Water?”

Ryan was caught off guard by the question.  He’d expected a job interview, not to be treated like a guest.  He thought he’d be inspected like a piece of meat, but other than the initial once-over he’d received, Leo acted as if they were all old friends.  “I think I’m good, thanks,” he said, looking to Wyatt but getting no cues from the bigger man.

Leo just nodded and turned to busy himself with an expensive looking espresso machine, waiting until the roar of the coffee grinder had subsided before continuing.  “So did you give him the rundown,” he asked Wyatt.

“The basics, but I didn’t want to overwhelm him,” the brawny hunk said, giving Ryan an encouraging smirk.

“Well then let me ask…what are your thoughts so far?”  Leo leaned back against the counter, his sculpted arms flexing as he folded them across his torso.

Ryan hesitated.  “Honestly?  It sounds great.  A little too great.  This is…new,” he laughed, looking down at his skimpy underwear.  “I’m not going to pretend like I’ve ever been in a situation even close to this before, but I’m a quick learner.  I’m just wondering what the catch is?”  He held his breath during the silence that followed, afraid he’d just blown his shot.

Leo’s impressed expression immediately put him at ease.  “Smart.  I can see why Wyatt likes you.  As far as a ‘catch’, I guess it all depends on how you look at it.  I wouldn’t call it that, but there are a few ground rules to follow.  First of all, and I’m sure Wyatt explained this part, this is all voluntary.  You don’t have to be here, and you don’t have to do anything you don’t want to do.  But,” he said, pausing for emphasis, “if you do choose to be here, then you’re choosing to follow the rules.  If you don’t, you’re out.  Understood?”  He waited for Ryan’s nod before continuing.  “Rule number one: you wear what I tell you to.  I’m sure you’ve picked up on what that usually looks like.  Around the house it’s as little as possible at all times, regardless of who’s here.  This place could be full of guests in tuxedos, but you two stay pretty much as you are now.  The same goes for when you leave the house.  I’m not sure what you’re used to wearing, but you put on what I tell you, and nothing more.  I can promise it won’t get you in trouble.  Beyond that…” he trailed off and smiled at Wyatt.  “I hear that’s how you two met in the first place?”

Ryan swallowed hard and nodded.  “Kind of hard for it not to catch my attention.”

“Hey, I’m glad it did,” Leo said, his tone warm and genuine.  “Rule number two: there’s no such thing as a closed door when it comes to me.  If I’m going to look after you, I think it’s only fair that I get to look AT you whenever I want.  Whether you’re taking a shower, taking a shit, or jerking off, if I want to be there, you’re going to have to be okay with that.”

Ryan said nothing, but nodded.  He felt a reflexive rush of embarrassment at the thought of the older man’s perpetual voyeurism, but then again, Leo was paying for the privilege.  And something about the way he’d said that he’d be “looking after” him filled Ryan with a strange warmth.  He’d always thought of himself as independent and had largely looked after himself ever since high school.  He’d never once stopped to think about what it would be like to let someone else take the reins, and while he’d expected to balk at any loss of control, he was excited by the thought instead.  Leo’s magnetic charm was as infectious as Wyatt’s, already making Ryan feel like he was in good hands though he’d only been around the other man for a few minutes.  The way he spoke, it was as if everything had already been decided, as if he knew better, and all Ryan needed to do was go along with it.

“Rule number three: your job is to basically do what you’ve been doing…hit the gym and keep yourself pretty,” Leo said, looking slightly bashful.  “And if I want you to focus on any specific areas, you’ll be expected to follow through. I know it might sound vain and shallow, but it’s essentially your one and only job, for which you’ll receive a healthy stipend each week.  If you find yourself wanting even more, there’s always the opportunity to do some…chores…” he grinned, winking at Wyatt.  “But again, that’s all entirely voluntary.”

Ryan felt his cock throb at the thought.  He knew exactly what kind of “chores” Leo had in mind, and while he’d never expected to find himself in the position of trading sex for money, it occurred to the young jock that it was far preferable to slaving away in filthy kitchens for hours on end.

“Rule number four: as far as your personal life goes, you’re still more than welcome to your own affairs, with a few boundaries.  You need to let me know when you leave and when you’re expected to be back.  Any overnight trips need to be approved in advance, and if they’re not, don’t bother coming back the next day.  Curfew is 10pm unless discussed otherwise.  I also ask that you give me a heads up if you’re going to bring friends over.  You’re more than welcome to have guests, as long as you’re comfortable following the rest of the rules while they’re here.  Lastly, in regards to sexual partners, unless we’ve talked about it, they’re standing in this room.  You’ve got yourself, Wyatt and me.  I think you’ll find the two of us more than up to the task, but if that’s not agreeable, I’m still happy to compensate you for your time today.  Four rules.  The rest is up to you.”