Straight Chad, Ep. 01

Chad enjoyed a friendly banter with the gay guys that frequented the gayborhood grocery store where he worked. He enjoyed his customers and chatting with them was fun. And the slight flirting was good practice if he ever got a more lucrative job bartending in one of the neighborhood's gay bars, where flirting would lead to better tips. And it helped that Chad made a point of remembering his customers' names, which flashed on the screen when they paid with a debit card.

It's not like he was leading any of his customers on. They knew he had a girlfriend. He referenced her often enough in conversations to make it clear he wasn't gay. Occasionally after work, she would meet him for a quick cocktail at one of the local gay bars before they headed home.

Lawrence was one of the store's regulars, a distinguished guy in his late 50s or perhaps early 60s, usually in a collar shirt and freshly pressed jeans or khakis. Chad was processing Lawrence's purchase of fresh fruit and vodka when, while reaching up to adjust a sign, his jeans inched down enough to show the waistband of his navy-blue Fruit-of-the-Loom boxer briefs.

"Forgot my belt today!" Chad said, laughing. "My pants almost fell down."

Lawrence winked. "In this neighborhood, I don't think anyone would mind."

Chad laughed again. "My girlfriend keeps teasing me that I should go to underwear night at The Phoenix one of these days."

Most of the gay bars in the neighborhood played pop music and catered to a collegiate preppy crowd. The seedier gay bars were all on the South Side. The Phoenix was an exception, a denim/leather bar with an edgier vibe. On Mondays, they had an underwear night where patrons could get drink specials if they stripped down to their undies. On these nights, the bar hosted a "best bulge" contest at midnight.

"You should," Lawrence said. "I dare you!"

Chad just laughed and shrugged. "I dunno, maybe someday."

"Seriously, I bet you a hundred bucks if you do it. I'll even pay for your bar tab, and your girlfriend's."

Chad winked and finished bagging up Lawrence's groceries.

Lawrence was halfway down the block when he heard Chad calling his name.

"I took my break," Chad said as he ran up to Lawrence. "Were you serious about that bet?"

"What's your Venmo?" Lawrence asked. Chad told him. A second later, Chad's phone buzzed, and he saw that a hundred bucks had been sent to his account.

"Wait, I haven't even agreed to this yet," Chad stammered.

"That's just to think about it," Lawrence said. "I'll make it five hundred bucks plus your bar tab -- and your girlfriend's -- if we go and you strip down to just your underpants and sneakers. You have to check everything else."

Five hundred bucks!

Chad was getting by with his grocery job, and his girlfriend made decent money with her sales job -- decent money, but not great money. Five hundred dollars could really help with the bills.

"Okay, let me talk to my girlfriend," Chad said.

Over the next few days, they firmed up the deal, agreeing to meet up that Monday at 9:00 p.m. when underwear night officially began. Lawrence offered to throw in an extra $100 if Chad agreed to wear plain white bikini briefs that Lawrence would provide. Chad provided his underwear size but wouldn't commit to wearing the skimpy briefs.

Chad and his girlfriend Amy were already waiting in front of The Phoenix when Lawrence strolled up the following Monday night. Chad was nervously clenching Amy's hand, perhaps to calm himself down, perhaps to send a signal to the gay patrons that he wasn't available for friskiness.

"Let's grab drinks and then I'll take you to coat check," Lawrence said. He ordered a Corona for Chad, a vodka cranberry for Amy, and a vodka soda for himself before walking the group to the back where the coat check room was located.

"Ready?" Lawrence asked as he handed over the plastic garbage bag from coat check for Chad to stow his clothes.

Chad looked around. "Shouldn't we wait a little?" he asked. "No one else is in their undies yet."

A few older guys had stripped down: an older bearish guy in a dingy jockstrap, and a middle-aged guy in blue briefs who looked like he'd been drinking since noon. Most of the other guys mingled about in jeans or the occasional chaps, all apparently waiting for more guys to make the first move."

Lawrence nodded. "Yes, now," he said firmly. "Show them how it's done. Besides, it will be more fun if you're the only eye candy."

More fun for Lawrence, at least.

Chad slowly unzipped his hoody, folding it and carefully placing it in the bag. "Are you doing it?" he asked.

"Nope, just you. Not me, not Amy."

Chad pulled his t-shirt off and carefully folded it. Nice, smooth chest with just the faintest sprinkling of chest hair. After handing his cell phone to Amy, he kicked off his tennis shoes and slowly slid his jeans off, blushing furiously.

"Socks, too," Lawrence said.

"Wait, what?"

"Yeah, the deal was everything except underpants and shoes. Put your socks in the bag.

Chad slowly peeled off his socks, standing barefoot on top of his shoes as he folded up his socks. Now he was just wearing somewhat baggy black boxer briefs.

Lawrence pulled the white bikini briefs out of his jacket pocket. "You brave enough to wear these?"

Chad shook his head. "Naw, I'm good. Not for a hundred bucks."

Lawrence looked up and down Chad's physique.

"Let's make it $250 for the briefs," Lawrence said, "but I get to watch you change into them."

Chad grabbed the briefs. "Okay, let's go to the bathroom," he said.

"Nope," Lawrence said. "Right here, out in the bar. Stand in the corner and Amy and I will shield you."

Chad stepped over to the corner, his bare feet padding on the sticky floor. With Lawrence and Amy trying to block prying eyes, he slid his boxers down and quickly stepped into the briefs -- but not before Lawrence got to see a glimpse his plump, cut dick and bushy, untrimmed pubes. What a wholesome, corn-fed, Midwestern boy! Chad quickly slipped his bare feet into his sneakers and tossed his boxers into the plastic bag. His bushy pubes were peeking out of the top of the briefs, and the sheer cotton fabric revealed the contours of his penis.

Chad's phone chirped in Amy's hand. He glanced at it and saw a notification that $750 had been deposited into his Venmo account.

Lawrence handed the bag with Chad's clothes over to coat check and gave the claim ticket to Amy.

For the next hour, Chad remained the only cute guy in his underwear. The back of the bar was dark enough that patrons seemed to be constantly "accidentally" brushing up against Chad's mostly bare body. The back patio had more elbow room, but Lawrence maneuvered them to stand under the bright lights so that his penis and pubes were barely concealed by the sheer fabric. Once, Lawrence had them stand in front of the bar on the sidewalk where the smokers congregated. For "fresh air," he said, but it was really so passersby -- including some of Chad's regulars at the grocery store -- could ogle his nearly-naked body.

By 11:00, quite a lot of other patrons had stripped down, too, including some closer to Chad's age. Most, however, wore solid-colored boxer briefs or boxers with fun prints. A few had tighty whiteys, but none as sheer as Chad's.

Amy was ready to head home. "But you should stay and enter the underwear contest," she joked.

Chad shook his head, but hesitated. He had a nice buzz going, he didn't have to work the next day, and he was enjoying the attention from the few girls there -- and even the attention from guys was flattering.

"Tell you what," Lawrence offered. "If you stick around until closing, or at least until I'm too pooped to party, I'll add another hundred bucks to the pot."

Chad had no idea what Lawrence did for a living, but Lawrence could have hired a high-end male escort spend the entire night for $850. He clearly wasn't struggling to pay the bills. "Okay, that's a deal," he said, signaling to the bartender for another bill. His phone chimed in Amy's hand as another hundred bucks hit his account.

Amy started to hand back the claim ticket for Chad's clothes, but Lawrence held up his hand.

"How gutsy are you feeling?" he asked. Chad hesitated. "I dare you to let Amy take the rest of your clothes home. I'll make sure you get home safe and sound in your skimpy undies."

The thought of being stranded in practically transparent underwear was frightening as hell. And his dick twitched in response. It was frightening...and exciting.

"I'll drive you home unless you'd prefer to walk," Lawrence said.

"You've been drinking," Chad responded.

"I'll get an Uber," he said. "Better yet, I'll get my friend Jim to drive us. He's a night owl, so I'm sure he'll be up. And he doesn't drink."

"How much?"

"Two-fifty?"

"Five hundred!"

"Deal!"

Shit. Chad didn't think Lawrence was going to go that high. Chad handed the ticket to the go-go boy staffing the coat check, and then handed the bag of clothes to Amy. His phone chimed as another $500 hit his account. He had made $1,350 already without putting out. Escorts got gang-banged for less.

Lawrence took Chad's phone from Amy and slid it into his chest pocket. "It's here whenever you want it," he said to Chad, "but if you tuck it into your briefs, they're going to slide down to the floor. Not that I'd object."

Chad's dick twitched again at the thought of his underwear "accidentally" falling down. He had never thought of himself as hot. The attention he was getting, albeit from guys, was intoxicating.

He kissed Amy goodbye and watched as she walked off with his clothes. Almost all. The only things between him and total nudity were a pair of shoes and a few square inches of sheer fabric.

Lawrence's friend Jim showed up not long after in response to Lawrence's text, ordering a club soda with a wedge of lime. Chad didn't object when Jim reached out and tweaked him nipple. He didn't even object when Jim's hand "accidentally" brushed against his briefs. If anything, he pushed his hardening cock up against Jim's hand. He wasn't into guys, but he always felt kind of average at best, and there was something validating about these guys' attention. A lot of the gay guys in their underwear had six- and eight-pack abs, yet Chad's shyness and vulnerability was clearly a draw.

And there was something exciting about feeling so vulnerable. It was like he was surrounded by wolves. Wolves that could tear his briefs off at any second and leave him naked and hard and fully exposed. Once at a fetish street fair, he had seen a college guy naked except for flip flips with his hands handcuffed behind his back while his girlfriend led him about on a leash. For weeks, Chad had secretly masturbated imagining Amy doing that to him. And now here he was, surrounded by guys he wasn't even attracted to, but the idea that they could overpower him was embarrassingly exciting.

Jim, who had been chatting with a leather daddy wearing only chaps, boots, and a leather harness, called Chad and Lawrence over.

"Chad, you interested in the underwear contest?" Jim asked.

"Oh, I don't know," Chad said. "I don't think my bulge is particularly impressive."

The leather daddy shrugged. "Prize is a hundred bucks for first place, fifty for second, and everyone who enters gets two top-shelf drink tickets."

"The tickets can be redeemed at any time," Lawrence said. "You're on my tab tonight, but you could always bring Amy back some other time."

"Also, it's not a 'best bulge' contest this week," the leather daddy said. "The first Monday of the month is a wet underwear contest."

Chad glanced down at the cotton briefs. They were already pretty damn sheer.

Lawrence whispered into Chad's ear, "An extra two hundred bucks if you enter, win or lose -- and of course you keep whatever prize you win."

Chad wordlessly took the clipboard from the leather daddy's hands and printed his first name on the appropriate line, with his signature and the date next to it.

At midnight, a spotlight hit a makeshift stage -- a piece of plywood laid across the top of the pool table, with some portable steps pushed up against it. The leather daddy, who was emceeing the contest, got on stage to announce the rules. Each contestant would strut about or dance on stage for a minute while volunteers in the audience squirted their underwear with water bottles. Once every contestant had shown their stuff, they would all be pulled on stage and dance together as audience applause narrowed it down to the final two. Then the final two would have a dance-off while applause determining which was the winner and which was in second place.

The first contestant was a trim 30-something guy with a hairy chest. He was wearing blue briefs but wasn't wearing anything else -- he had even kicked off his tennis shoes so they wouldn't get wet.

"Name, position, and are you single or taken," the leather daddy asked.

"Name is Brad," the guy said. "I'm vers, recently single, and very much looking to get laid tonight."

The crowd roared with approval.

The outline of Brad's semi-erect cock was visible when his briefs were sprayed with water, but if anything, the blue briefs got darker when they were wettened. He didn't show too much, but he was a good dancer and put on a fun show for the crowd.

The second contestant was a middle-aged bear wearing a dingy jockstrap and hiking boots that he kept on.

Chad was third. He kicked off his tennis shoes just before jumping barefoot onto the stage. Feeling the board beneath his bare feet really made him even more aware of how vulnerable and exposed he was.

"Name, sexual position, and single or taken?" the lather daddy asked.

"Umm...Chad. I'm...I don't know what you mean by position. Missionary? I'm taken. I have a girlfriend."

The audience shouted out their approval.

"Wait, you're straight?" the leather daddy asked. "Or...are you bi?"

"I'm straight," Chad said, nervously. Would the crowd turn on him? Would they think he was invading their space?

"But, you know, a hundred bucks is a hundred bucks," he added. "Gotta pay the bills!"

Fortunately, the crowd laughed. The leather daddy signaled for the music to play.

Chad wasn't much of a dancer, but he swayed back and forth as water hit his crotch. Warm water, fortunately. No shrinkage. If anything, his dick was getting increasingly close to being erect.

He glanced at a mirror that flanked the stage and was shocked to see that he could see his pink dick and dark pubes easily displayed by the all-but-transparent wet cotton briefs. He was essentially naked in front of gay guys. And a lot of them had their cell phones trained on his bare body.

And then it was done. Chad hopped off the stage and quickly downed a shot of whiskey that a go-go boy handed to him. Lawrence had his shoes, but he didn't bother to put them back on. Barefoot in a bar was weird and kind of gross but kind of exciting. As Lawrence handed him his beer, he felt Jim's hand brush against the wet fabric of his underwear. Chad grabbed Jim's hand and maneuvered it inside the back of his undies so that Jim's hand was cupping his bare ass.

Two guys went after Chad, but he was too amped up to focus on them. "I have to pee," he said to Lawrence.

The bathroom he chose only had urinals -- individual ones along one wall, and a big trough backed by a mirror along another. Feeling daring, he stood barefoot at the trough and peeled his sopping wet briefs down to his knees. Several people were coming and going, and they all got a good look at his pale, untanned ass and, when they looked at the mirror, his stiffening cock rising out of his untrimmed pubes.

He got back just as the leather daddy was getting ready to call all five contestants back on stage. The first guy turned his back to the audience and peeled down the backside of his underwear so his bare butt was on display. The second guy in the dingy jockstrap had already been showing his ass all night. Taking his cue from the first guy, Chad also bared his butt to the audience as the fourth and fifth contestants bounced around to make their dicks flop around in their briefs. Like the first contestant, the fourth and fifth were also wearing colored underwear that didn't reveal as much when wet as Chad's white briefs.

The leather daddy had the audience cheer for their favorites, and the top two were clearly the first guy and Chad. The leather daddy kept them on stage while dismissing the other guys.

"Okay, everyone, they're going to dance off again for a few minutes," the leather daddy said. "When they're done, I want you all to just cheer for one of them so we can pick a clear winner."

The music started again and the volunteers with squirt bottles began to spray them again. The first guy had peeled down the back of his briefs again and was bending over, spreading his cheeks to show hole. Chad also had his ass out, but he had to do more. The first guy had come with a bunch of friends, so Chad really had to win over everyone else if he wanted to win.

Gulping, his bare ass still bobbing up and down in front of the audience, he reached into the front of his briefs and cupped his cock to cover it, and then used his other hand to pull his briefs all the way down. He stepped one foot out of them and then spun around, using his other to kick his briefs towards Lawrence in the audience. Fortunately, his aim was good.

Now he was on stage in front of dozens of gay men, soaking wet, completely naked, with only his own hand covering his dick.

The crowd went wild and when it came time for the audience to vote by applause, Chad was the clear winner. Even some of the first guy's friends cheered for Chad.

"And we have a winner!" the leather daddy said, grabbing Chad's free arm and holding it up like a boxing referee would.

Drunk off of the audience's response, Chad raised his other fist and pumped it in the air, fully exposing his half-hard dick in the process. He quickly cupped his cock again, feigning embarrassment -- but his full exposure had been quite deliberate.

The leather daddy handed Chad a crisp hundred-dollar bill, and the straight lad hopped off the stage to grab his underwear from Lawrence. He took his time slipping his undies back on, pretending to lose his balance a few times so that his exposed dick would wag back and forth as he stopped himself from "accidentally" falling. Joe handed him his shoes, and he quickly slipped his bare feet into them.

At Lawrence's suggestion, he put the cash in his wallet and Venmo'd the amount to Chad so he wouldn't risk losing it. Later, when Chad saw his Venmo accounting, he realized that Lawrence had doubled it, adding a hundred percent gratuity to his winnings.

After finishing their round of drinks, Lawrence suggested it was time to go. It was just past one in the morning. The bar would have last call soon, and Chad would be out on the streets surrounded by the entire neighborhood's bar patrons while wearing only transparently wet underpants.

There were still plenty of people out on the street, even after midnight on a work night. Joe had left his car at the other end of the gayborhood, and Chad was forced to walk two blocks under the prying eyes of the neighborhood's night owls.

Back in the car, Chad sat in the front passenger seat while Lawrence hopped in the back. "It's up this street here, then a left at the crest," he said, directing Joe. "My apartment is near the top of the hill."

It was only half a dozen blocks from the bar, but up an obnoxiously steep hill. Easy enough to walk down to work, but a pain going home.

At the top of the hill, Chad directed Joe to pull over next to a small playground. At this hour, it was deserted, and the park was surrounded by too many trees for most residents to see, even if they were still awake.