Bartering For Bartending

This is my entry for the

On The Job Challenge 2025

. I would love a vote and a comment.

***

This may be based upon a very possibly true story.

***

"If you teach me to bartend, I'll show you my tits."

Unlike most quirky little workplace traditions, I know exactly when this one began.

"Can I be cut early tonight?" Jenny asked Jon, the assistant manager. "I have one table left. They have their check and I've done my sets."

"I dunno. What'll you give me?" Jon smiled as he shuffled through the night's receipts.

"Um. I... Aha!" Jenny reached into her apron pocket and pulled out a new pack of gum. "A stick of Big Red?"

Jon looked around the dining room, deader than usual for a Tuesday night. "Give me the whole pack and you can go now."

"Deal," she answered and slapped the bright red pack of cinnamon gum into his outstretched palm.

"Thanks, Jon!" she called as she clocked out and opened the back door of the restaurant.

From then on, the managers, especially Jon, were 'bribed' for favors.

"If I give you this gum, can I trade finishing my sets for filling the salt and pepper shakers?"

"Nope," Jon replied the next evening, "I still have three pieces left. What else ya got?"

Anne thought for a while and scribbled a quick sketch on a sticky note. "A hand-drawn picture of a tree."

"Looks more like a circle on a stick to me," he said. "Who's supposed to be doing the salt and pepper?"

"Brett and he's okay with it."

"All right. You two can switch."

It took off from there. Busboys traded "fries from table 6, practically untouched" for a trial shift as a dishwasher. The dishwasher offered up a "ride on my motorcycle when my mom finally lets me get one" for an extra night off. The head cook said he'd let the manager select the kitchen music for the evening -- the traditional perk of the back of the house staff -- for a comped meal for his pal and a date he wanted to impress.

"A coupon for a free beer at Ned's tomorrow night if I can skip my next table. I really need a chance to sit down," Emily said.

"Tomorrow's quarter beer night at Ned's. Not much incentive there," he said.

"Please." The word gained at least two syllables as Emily pleaded.

"Okay," the manager said, "no sense of overdoing it. Tell the hostess to pull you from rotation for a while."

No one was pressured into participating and everyone enjoyed playing the game. I hadn't played yet; but tonight there was something I wanted.

The evening was winding down. It had been particularly hectic tonight. A weekend night and a home game always meant a full house and a busy night. The dining room was finally clearing out; the waitstaff was on their way out the door and I'd just dropped the last check at my last remaining table. Jon was doing his nightly walkthrough when I murmured in his ear.

"If you teach me to bartend, I'll show you my tits," I said and kept walking back to the breakroom. I know he heard me because his step faltered for just a second before he continued with his routine.

I clocked out and waited in the breakroom as the hustle and bustle of the restaurant dwindled down and finally stopped completely as the manager collected the night's cash from the bartender on his way out and locked the door behind the dishwasher as he headed out to his car. Jon flicked lights off as he made his way back to his office across from the break room.

I watched as he stashed the money in the safe and spun the combination lock. He patted his pocket for his keys, grabbed his jacket and turned off the lights as he walked out the door. He stopped at the break room door and slid his hand down the wall, looking for the switch.

"Not yet," I said in a low tone.

"Julie?" His voice was startled. "What are you still doing here? I thought you'd left thirty minutes ago." He looked into the break room. It was a small room with a table, a couple of chairs and hooks on the wall laden with aprons and assorted items. The short counter along one wall held stacks of menus, napkins to be folded and cups filled with pens deemed not good enough to be claimed for personal use but too good to be thrown away.

"There's something I want." I shuffled the deck of cards I'd found and looked up at him. "I'm waiting for my answer."

"You were serious about that?" Jon said, "I thought you just said it to get a rise out of me."

"Did it work?" I asked, dealing another round of solitaire and glancing pointedly at the front of his pants. "Oh, I see it did."

"I'd love to see your tits."

"And you'll teach me to bartend?" I asked.

"Mmhm," Jon said.

I unbuttoned my blouse and shrugged it off my shoulders. My lacy white bra was quite sheer and did very little to conceal my nipples from Jon's admiring gaze.

"I have an offer of my own to make," he said, "but I'm going to need to see the actual tits to see if it's worth it," he countered.

"My tits are always worth it," I said as I pulled the cups down, exposing my breasts to him. I felt my nipples harden as they were exposed to the cool air in the room and his appreciative looks. "I'm always worth it," I added.

"Mike handed in his two week notice tonight. How about a game," he indicated the cards on the table, "to decide if you get to train under him before he leaves?"

"What kind of game?" I asked, gathering up the cards and shuffling them a few times before stacking them neatly on the table.

"Poker," Jon said. "Five card draw."

"Okay," I said and motioned to the chair across from me as I straightened my bra, concealing my breasts once more and buttoning my blouse.

"You didn't need to do that," he said.

"Yes, I did," I said, "because we are playing Strip Poker tonight. If I win, Mike's going to train me and I get to be the on-call bartender sometimes."

"And if I win?" Jon smiled confidently.

"You get to see me naked," I replied with a grin.

"Seems a bit skewed in your favor," he said. "We may have to do a bit more negotiating later."

He sat down on the chair and we agreed on the rules; jewelry didn't count; each item of clothing had to be completely removed, etc. We inventoried each other's clothing and decided we were evenly matched. We cut for the deal and the game began.

I straightened the cards in my hand. Hm. Three sevens. Could be worse.

"Two," I requested and dropped the two on the table. The two he gave me joined the others in my hand.

"I'll take one," Jon said and tossed his unwanted card on top of mine. He drew one from the top of the deck, looked at it and tucked it in with the other four.

I looked at him. "Ready?"

"Yep. Let's see what you've got."

"Three of a kind. Sevens," I said, spreading my cards on the table.

"Not bad," Jon said, "but it doesn't beat my three of a kind. Tens." He fanned his cards out in front of me.

I bent down, untied one shoe and tossed it into the corner.

He smiled and handed me the deck. "Your deal," he said.

He lost the next two hands. His shoes joined mine in the corner.

After three more hands, I was barefoot, my socks discarded as well.

We exchanged winning and stripping until I was down to my panties and bra, my skirt and blouse added to the stack in the corner. Jon fared a little better. He was still wearing his pants.

I peeked at the cards in my hand. It was a mishmash of odds and ends. I had at least one card of each of the four suits and my highest card was a nine. I contemplated what article of clothing I'd be removing next. Not much choice, I thought. Panties or bra?

"How many can I discard at one time?" I asked.

"Ouch. That bad, hmm?" Jon said.

"Oh, it's a great hand. I was just asking for future reference," I lied and bosomed my cards, holding them closer to my chest.

"You don't exactly have the best poker face," he said, "and to answer your question, three."

I chose three at random, keeping that nine, and put them on the discard pile. Jon counted out three cards and slid them across the table to me. He dropped a couple of cards and added two replacements to his own hand.

I reached for my new cards but he put his cards facedown on the table and said, "Before you pick those up, how about a drink? It was a long night and I could use a little something."

"Diet Coke?" I asked.

"I was thinking more along the lines of adult beverages," he replied.

"You must not have too much confidence in your poker face," I teased, "if you're trying to get me drunk."

"Not drunk exactly," Jon said, "but a little tipsy might be fun."

"Okay. That sounds good."

"Let's go," he said as he scooted his chair back from the table.

I joined him in the short walk to the bar, trying not to think about the probably as yet uncleaned floor under my feet. He flicked a switch and a couple of the neon lights illuminated the area behind the bar in a warm glow.

"What's your pleasure?" he asked.

"Long walks on the beach, moonlit nights and kissing in the dark," I answered, using my best sincere beauty contestant voice, echoing the cliched response of every Playboy centerfold's interview.

"Good to know," he laughed, "but I was talking about your drink."

After a moment's thought I said, "something light and fruity. A girly drink with lots of ice."

"Come on behind the bar, and I'll give you your first unofficial lesson in bartending."

I stood beside him and watched as he pointed to a rack of tall glasses.

"Grab a glass and fill it with ice. Always start with the ice."

I took a glass and reached into the ice.

"Use the scoop. You do not want to have to empty all the ice, clean up all the pieces of broken glass and have to refill it on a busy Saturday night."

I did as he instructed and waited for the next step.

"Tequila sunrise."

"Good song," I said.

"A classic," Jon agreed, "and a good drink for your first lesson."

"Tequila next?" I asked.

"Yep," he said, and pointed to the bottle in the well. "It's the one with the yellow pour spout."

He reached around me and put a shot glass on the bar. "You'll learn to count later on but right now, let's measure."

I poured the tequila into the shot glass and looked over at Jon. "Pour it in?"

"Yes," he said, "and then put the bottle back in its place. You want to be able to grab it without spending time hunting around for it. The orange juice is in the fridge right there and grab the grenadine while you're there."

I found the bottle of orange juice and, after a bit of rummaging, the small bottle of grenadine syrup.

"Fill the glass with the juice and then drizzle the grenadine over the top," Jon instructed.

I filled the glass with orange juice and reached for the shot glass. "How much?"

"You don't need the shot glass. The grenadine's non-alcoholic. Pour until it looks pretty."

I did as I was told and put the bottles back in the cooler under the bar, making sure the latch caught.

"A straw and you're finished. We'll skip the cherry for tonight." He pointed to the dispenser of long plastic straws.

"Good because I still haven't mastered the art of tying a knot in a cherry stem with my tongue," I said, dropping the straw into the glass. I stirred gently and admired the colors as they blended.

Jon made a chuffing sound and choked out, "Good to know."

He grabbed a bottle of beer from the cooler and pointed at my drink. "How's yours?"

I took my first tentative sip and smiled. "It's perfect."

"Let's get back to our game. As I recall, you were getting ready to take something else off."

He grabbed a couple of cocktail napkins, handed me one and shut off the light as we left the bar.

I sat down at my place and put my drink, which really was perfect, cold and delicious, and picked up my cards. I almost did the classic spit take when I saw what I'd been given.

"Didn't help, huh?" Jon asked.

"I'll never tell," I said.

"I'll go first," he said, putting his cards down on the table one by one. "Full boat. Threes over fives."

He looked at me and said, "I'm hoping for your bra next. I want to see those pretty tits again." He reached out and almost touched one breast with an outstretched fingertip.

"A full house. Does that beat a pair of nines?" I asked, batting my eyelashes in an exaggerated coquettish manner, counting the pair of nines.

"No, sorry," he smiled. "Need some help with the hooks in the back?"

I mirrored his smile and continued. "How about two more nines?" I added the other two nines to my hand. "One. Two. Three. Four."

"You drew three nines!?!" Jon shook his head in wonder.

I twirled my hands in a "hurry up" motion. "Take off those pants. I've often wondered if you were a boxers or briefs kinda guy."

"All you had to do was ask and I'd've told you," he said as he stood up and unzipped his pants. "Of course, it could be commando."

"Nope, not tonight. You would have been more bothered."

He balanced on one leg as he removed his black jeans. He kicked off the jeans and stood for a second in a typical Sears catalog clothing pose, looking at an imaginary watch on his wrist.

"Boxers. Just what I thought, although I wasn't expecting the bright red and pink hearts."

"I didn't have time to do laundry this week." He sat down and handed me the deck of cards. "Shall we go on? I have a feeling the next few hands are going to be very interesting."

I lost the next hand and did my best imitation of a burlesque dancer as I unhooked my bra, clutching the lacy cups and sliding each strap off my shoulders. I tossed it across the table and watched as the white lace fell into his lap. He gulped and took a long swig of his beer.

"Last hand," I said, gathering up all the cards, idly shuffling them a few times. "Let's raise the stakes," I suggested.

"What did you have in mind?"

"If I win, I train with him like we agreed earlier and," I continued, "I take over Mike's regular schedule when he's gone."

"And if I win?" Jon asked.

"I train with Mike and take over his shifts-"

"That doesn't sound like much of a deal to me," Jon said.

"-- and you get a blow job," I finished.

"Deal!"

"High card deals this last hand." I suggested.

Jon cut the cards and showed me the jack of diamonds.

My cut yielded the queen of hearts which I took as a very good omen.

"My deal," I said and shuffled the cards and handed the deck to Jon to cut. I dealt out our last hands and took a deep breath before I picked up mine.

Jon must have noticed my hesitation because he said, "Julie, we don't have to do this. We can stop right now. I'll make room for you on the schedule, win or no win."

"No," I said, "I'm cool with all this. I was just enjoying the anticipation."

"You're sure?"

"Yep," I said because I was sure. This was my idea. Mine to win or lose.

Jon looked at the hand I'd dealt him, put a couple of cards on the discard pile and asked for two. After I gave him the requested pair, I looked at my hand. Hmm. A nice run of hearts, three, five, eight, a jack and a pesky seven of spades spoiling all the red. A pretty good chance for a flush so I discarded the spade and took one from the top of the deck.

"It looks like you'll be getting your chance to tend bar," Jon said, and put his cards face-up in front of him. "The best I can do is a pair of sixes." He stood up and began to take off his boxers.

"Just a minute," I said as I called out each of my cards as I put them down on the table. "Three of hearts. Five of hearts. Eight of hearts. Jack of hearts. And..." I put the last card face down on the table, stood up and shimmied out of my last bit of clothing. "You win," I said, turning over the four of diamonds.

"Fuck," Jon said under his breath, less a curse and more an offering of gratitude. I moved my chair around until it was beside his and sat down.

"Not tonight -- just a blow job -- but maybe a fuck sometime later."

My hand stroked his hard cock through the thin cotton of those heart-spangled boxers, a feeling reminiscent of nights past spent parking although I was never nude, not completely, in those car seats.

I gently touched one erect nipple with my fingertip. "Okay?" I asked.

"It's more than okay."

I played my fingers over his chest, teasing each nipple until they were as hard as mine. I caressed his cock, dipping my hand into the elastic waistband and rubbing the drops of precum over the swollen head. I tugged the boxers down and his cock sprung out.

"Wait," Jon said and he reached behind him, stretching out his arm until he could grab the stack of linen napkins. He dropped them at his feet and said, "for your knees."

I knelt down in front of him and licked the head of his cock, enjoying the feel of him on the tip of my tongue as I swirled it around the top and then slowly licked my way down, tracing the veins as I went and then licked and kissed back up to the head once more.

I opened my lips and took him inside my mouth. I lowered my head ever so slowly, liking the feel of his cock as I sucked him, the feeling of power over him, knowing I was the one who was causing those audible inhalations of breath, those gasps, as I reached his balls and flicked the tip of my tongue over them.

I licked and sucked his cock as I raised my head and opened my mouth, releasing his cock with a little pop.

"How sturdy is this table?" I said as I played my fingers around and around his cock.

"Uh? What?" Jon asked. "Sturdy enough, I guess. Bob was standing on top of it this afternoon."

"Whatever for?"

"Emily saw a spider."

"That's what that screech was!"

"Yeah, Bob caught it and stuck it on the azalea bush outside. Why?"

"Because I want to do this," I said, and cleared the cards and our drinks from the table and put them on the counter. I perched on the table, lay down and moved around until my head was hanging off the edge. "Come here."

I licked my lips as he stepped in front of my face, his cock perfectly positioned so I could take in his entire length. He slowly slid into my open mouth, deeper and deeper until his cock filled my throat.

"Okay?" Jon asked.

"Mmmhmm," I murmured and smiled around his cock the best I could.

He eased out until just the tip of his cock remained in my mouth. He rocked back and forth in a slow and steady motion. "Can I play with your tits?" he asked and when I nodded, he reached down and touched each nipple, gently at first, gradually increasing the intensity of his touch. Flicking each nipple and then soothing them with a light caress. Rolling them between his thumb and fingers, all the while keeping up the rhythm of his hips.

I reached my hands around him, holding onto his ass and encouraging him to go deeper and harder. He paused at the top of his stroke and looked down at me. I pulled away until his cock barely rested on my lips and said, "Fuck my face." He did.

A few more thrusts and his balls tightened. "I'm going to cum all over those pretty tits," Jon said and he spurted white hot cum, a bit on my still open mouth, most of his load on my tits. "Oh, fuck. Oh, fuck. Oh."

"Whew," Jon said and collapsed on the chair. "Just a sec," he said and left the breakroom, coming back with a dampened napkin. He wiped his cum off my breasts and then cleaned himself off. "Your turn?"

"No, not tonight," I said. "Maybe another time."

"And maybe in a bed next time," Jon suggested.

"Sounds good," I agreed.

We dressed and tidied up the breakroom, took our glasses back to the bar, cleaned them and put them back on the drying rack. Jon made sure all the lights were off, the alarm was set and locked the door behind us. He walked me out to my car, parked a few spaces from his on the far side of the lot.

"Uh. Um. I have a confession to make," Jon said as I opened my car door.

"Oh?"

"I loved everything about tonight, but you really didn't have to do all that. I already decided you would be the perfect candidate to replace Mike at the bar."