It was the spring of 1987. Kelly and I had visited some friends and, on a whim, took a backroads route home. It was dinner time on a Saturday. We spotted a bar in the middle of nowhere with a full parking lot and decided to pull in.
We had great service and a great meal. It was more than halfway through our meal when I noticed him. He was working the dining room from table to table and certainly seemed like he was the manager or owner.
I nudged Kelly. When she spotted him, her jaw hit the floor. At that moment I was willing to bet a paycheck that it was Gary.
We had met Gary a couple of years before this. He owned a small Northwoods bar. It’s a story that I’ve shared here previously. Super short version: I had sex with one of his servers out in our car while Kelly and Gary screwed all over the bar. It was a random, serendipity kind of a night and we had never seen any of those folks before or since.
Here we were, two years later and four hours away and seeing Gary. He stopped at our table to ask how we enjoyed our meal. Kelly’s head was down. She raised her head and looked him in the eyes and said, “It’s all been wonderful.”
I couldn’t help but enjoy seeing the look on his face as his brain worked overtime until, bingo! “Kelly?” Gary’s face first went white, then turned red. He pulled out a chair, without thinking to ask, and sat down with us.
Kelly replied, “Yep, it’s me! How have you been, Gary?” Well, that began a half-hour conversation of Gary telling us about his life since that wild night. Summary: He got divorced after sleeping with the help, had to sell the bar to settle up, found this place a year later, bought it, and moved. And now owned a bar less than a half-hour from where we lived.
Kelly couldn’t help herself and Gary was still Gary, which meant they were flirting mercilessly. Gary got up a few times to attend to work but kept stopping back at our table.
At some point, the topic of Kelly working at the bar came up. Kelly had been a server at a couple of places while in college but now had a “real” daytime job. She exactly wasn't warming up to the idea of late nights and early mornings.
Gary spent a lot of time sharing his story of the place. On Friday and Saturday nights they were a good restaurant, a family place, with a loyal following and a good business. They were closed on Sunday. Monday through Thursday they didn’t sell food and were a fairly rowdy bar. They had a completely different staff during the week from those who worked on the weekends.
Gary went into detail that this is what he got when he bought the place. During the week, they had barely dressed servers and bartenders that focused on selling shots, flirting, and flashing their boobs (more than just once in a while). Gary was describing to Kelly what the staff wore and he could tell she wasn’t really believing him.
Gary made a fast trip to the office and brought out a photo album of their celebrations. It seemed the celebrations were nearly weekly and any excuse would do. St. Patrick’s Day, sure, that made sense. Ever hear of National Tequila Sunrise Day? I was pretty sure Gary made up most of that stuff, but it all looked like fun!
Gary’s book was full of pictures of the girls in lingerie, bikinis, mini-skirts, you-name-it, all barely dressed and grouped around guys with smiles from ear-to-ear with a drink in their hand, mouth, or both. Think of Hooter’s dialed to eleven with fewer clothes. The only dress code was that they wore black, with no rules on how much.
I was working some long hours at work so I guess I wasn’t stunned when Kelly started agreeing that it sounded like it could be fun. Gary lost a girl last week and was trying to fill the position. They compromised and Kelly agreed to come in the following Tuesday and spend a few hours to see if she thought it would work.
We said our goodbyes, having been there for nearly three hours. Gary enjoyed a very long boob-smashing hug with two handfuls of Kelly’s little butt. As soon as we were in the car I could tell Kelly’s mind was racing a million miles an hour. She spoke very little on the drive home. I left her to her thoughts.
As soon as we got home she went straight to the bedroom, stripped naked, and started grabbing things to model for me.
Naked, Kelly was a goddess to behold. She stood about five-feet-two-inches tall with dishwater blonde hair that was so incredibly long it hung to the backs of her calves. At twenty-five years old, her 34F boobs jutted out firm and high, as Bob Seger sang to us. Her areolae were light pink. When aroused, her nipples would look like red peanut M&Ms.
They were giving her away that night. She was very turned on! Kelly had a short torso which made way for very long legs for a shorty. Her legs were topped by her cute bubble butt. Her pussy was neatly trimmed that day, but I knew that hair was probably short-lived.
Kelly came out into the living room showing me a variety of black panty and bra combinations. She also modeled her only black bikini and then a black denim mini-skirt that was kind of pleated and flouncy and very short. She settled on the mini skirt and a front hook half-lace bra.
Then she stripped both of them off and crawled onto my lap and we started making out like a couple of horny twenty-five-year-olds. Watching all of her outfit changes and knowing she would be wearing some or all of them in public at the bar had my cock stiff and dripping the whole time.
Kelly was rubbing my cock through my jeans. I was fingering her cunt and sucking her nipples. Kelly stood and helped me strip naked. She hopped onto the couch and lowered herself onto my cock.
We started talking about the bar. She knew it would be a challenge juggling two jobs. She also didn’t think she would do it for too very long. But the whole thing just sounded so sexy to her that she couldn’t imagine saying “no” without at least trying it out.
Kelly started asking what I thought the men might do to her. I told her what she needed to hear. My answers were filthy. They would touch, probe, and fondle every inch of her body. They would suck everything that she would offer them from her toes to her ears. They would fuck her as hard as they could wherever she would take them: on a table, in their car, in the bathroom, on the floor.
Kelly was moaning and groaning through all of it. I couldn’t hold out much longer and I started to buck her cunt up and down on my lap. I was telling her that was how the men would fuck her. Kelly screamed, "Oh Fuck!" and buried her face in my shoulder. I could feel her squirt a river all over my groin.
A few strokes later, as she was still cumming, I pumped her full of the load I had been building for a few days. Kelly was shaking hard from orgasm aftershocks. She was slowly coming down from the mountain. Eventually, she was back in control.
She had neglected to catch my load. When she slowly stood, a massive amount of my cum was added to my lap, already wet from her own. I headed to the shower. Kelly headed to bed.
Luckily, the next day was Sunday. We woke up and fucked, fucked again later, went shopping for a while, came home, and fucked some more. I was thinking that Kelly working at the bar could be a great thing for us!
Kelly had gotten me to commit to driving her to the bar for her trial run on Tuesday. We arrived a bit before seven and Kelly was supposed to be there until eleven. I grabbed a table in the corner and ordered a beer.
Kelly was wearing her mini-skirt and a front-hook half-lace bra under a half-buttoned black blouse and cowboy boots. I didn’t know it at the time, but she had forgotten her panties. She had to control her hair somehow, so she had it in two side ponytails.
Gary greeted her immediately and started to introduce her, first to the crew and then to some customers. Tina was the bartender. Her mom had owned the bar before Gary and she was the literal wild child.
Tina was about five-and-a-half-feet tall, probably 36DD boobs popping out of a 36C bra. The tops of her tits rolled like the ocean’s waves when she moved. She was wearing black panties that covered about half of her very shapely butt. They were also a size too small.
She was a bit of a loudmouth and a little rough but seemed like a shit-ton of fun. If I had to guess, I would peg Tina at maybe thirty to thirty-five? Tina had shoulder-length brunette hair and she was wearing a cowboy hat and boots.
Becky was teeny-tiny. She was about a hundred pounds of little, except for her boobs. She was probably a 30C. Her ass was almost non-existent. She was wearing a black bikini that was perhaps a size zero. Nice cleavage though. She had black hair that was fairly short in a bob. Becky was wearing black sneakers that were maybe a size five.
Becky had a fairly high voice and it wasn’t hard to tell where she was. Even though you could barely see her, every time someone grabbed a boob or her butt she squealed and giggled. Becky squealed quite a lot.
Gary took Kelly back to his office and covered some new-hire stuff. He let her know that staff was limited to three drinks per night and they had to be paid for. If she paid for her own, she wasn’t working it very well. It was okay for boobs to come out for a minute or so but she couldn’t work topless.
Guys liked to order slippery nipples and get more than just a shot. He also explained the phone booth. There was a real-life phone booth in the corner near the bar. The glass was tinted. It was tight in there but she could take a customer in there for a couple of minutes if she wanted. Just touchy-feely stuff as long as she was getting tipped.
Fifteen minutes later Kelly came out with her blouse off and started working, to a cheer from the bar regulars. I could see she had hiked her boobs in her bra so her nipples were visible and poking through the lace.
By the end of her shift pretty much every guy in the place had rubbed her legs from boots to butt. A couple of good-looking lucky guys each got a finger wet under her skirt. She had opened her bra to a half-dozen guys that bought the $10 shots and got to lick them from her nipples. One guy tipped her $20 to visit the phone booth and he sucked on her huge tits for a couple of minutes.
At the end of the shift Kelly told Gary she had a lot of fun and she agreed to work two nights per week. In the car on the way home, Kelly counted her tips that she had been stuffing into her boots all evening. She had made a hundred bucks in four hours! As soon as she was done counting her money she leaned over to my crotch, unzipped me, and sucked my cock until I nearly wrecked the car.
As soon as we walked in the door at home it was a race to the bedroom. Kelly jumped on the bed, lay on her back, and hiked her boots into the air. I stripped as fast as I could and discovered she was without panties and had shaved bare. I fucked the hell out of that little pussy until we both exploded.
Kelly wanted to enjoy the three-drink limit at work, and guys were in line to buy them, but she wasn’t comfortable driving afterward. So, as often as I was available, I would drive her to work, hang out at the bar, and drive her home. I always sat as far away from the action as I could, wanting to give Kelly all the playing room she needed.
She had been working there for maybe three weeks when she noticed one of the servers had gone missing. She asked Tina if she knew where she’d gone. Tina started up a conversation with Kelly about how she felt about working there, how she liked the customers, and on and on. Kelly realized later that Tina was protecting Gary and wanted to know Kelly was committed to the place before letting her in.
Kelly must have passed the test. Tina explained that Gary never hits on the staff, but he is human. The girls have taken it upon themselves to occasionally ask Gary if he needs some “stress relief”. If he does, they head to his office and Gary gets a blow job. Just then Becky reemerged through the kitchen door licking her lips with a devilish look in her eye.
The following week, on a night Kelly was working, it was the first really nice summer-like day of the year. The bar was dead and the girls were bored. Kelly was in back when Gary walked by. She stopped him and asked if he needed some “stress relief”. Gary just grinned and walked to his office. Kelly followed.
As Gary closed the door he said, “So, you’ve been talking to Tina?” Kelly was reaching for his belt and getting his jeans loose and pulled them to his knees. “I hope you didn’t share too much with her?”
Kelly said, “Don’t worry. No one knows how we met or that we’ve fucked before.” She could hear the sigh of relief come from Gary. “Here’s my friend!” she said as she grasped his limp cock. She sucked him into her mouth and used her tongue to work him up to a full-length six-inch fat hard-on.
Kelly had been deep-throating Gary for several minutes. He was hard as wood and softly moaning as she worked her magic on his cock. He tugged at her shoulders and Kelly stood. He unclasped her front-hook bra and released her boobs.
In between sucking and mauling her tits, he said, “Do you have any idea how many times I have replayed that night in my mind? And then to actually see you again? And then to have you working here? And now to feel your body again? It’s almost too much.”
Kelly pulled up her skirt and exposed her bare snatch to Gary. “Do you know how badly I want you to fuck me again?” she asked him. Gary reached for her cunt, slipping a couple of fingers into her sopping wet gash. Kelly had her first orgasm in seconds. Gary didn’t stop and she came again a couple of minutes later.
Kelly said, “I can’t take this.” She turned around, grabbed his cock between her legs, and held him tight as she dropped her gash onto him. Once fully coupled, Kelly sat still for a moment enjoying the heat and fullness of his cock. She barely moved, yet within a minute Kelly had a shuddering orgasm.
The sound, although very quiet, and the feel of Kelly coming on his cock was too much for Gary as well. Clearly, the tension had been building between the two of them. Two firm pumps and Gary blasted his load into her wet twat.
Immediately Gary felt a tinge of regret. “You know I just broke my rules.”
Kelly said, “I’m grandfathered in. We fucked before I started here. And you know I’ll never tell the girls.” Kelly had quickly wiped her cunt and reattached her bra. She kissed Gary on the cheek and said, “I need to get back to work, boss.” She slipped out of the office and went back to work.
Kelly kept things cool at work with Gary. She didn’t offer stress relief any more often than the other girls. Although Kelly couldn’t help herself and she fucked Gary each time she offered a blowjob. They were always quiet and quick and no one suspected anything.
One night they had just gone to the office for stress relief. Kelly had barely gotten his cock out and was on her knees sucking him as he sat in his office chair. There was a soft knock at the door. Gary looked confused. They both just assumed it was one of the other girls. “Do you mind?” Gary asked. Kelly shook her head no and Gary said, “Come in.”
Kelly is a born exhibitionist. It flashed through her mind that one of the girls, maybe Tina, would get to watch her cock-sucking skills. It was making her pussy even wetter. She was knocked out of that thought when she heard a man’s voice say, “Oh, shit! I’m sorry, Gary. Tina said it would be okay to come back here.”
Gary said, “Don’t worry, Tad, come on in.” Tad came in and sat in the chair next to the desk. Kelly now recognized him as one of their regular customers. She felt Gary’s cock start to shrink but she kept him fully engulfed in her mouth and put her tongue to work to get him back up.
Tad was trying to focus on why he was there, but suddenly he had a dry mouth and couldn’t speak. Kelly could feel his eyes staring at her. She unclasped her bra and removed it while she continued to suck Gary. Tad started to try to say something about a softball team.
Kelly stood up and stepped over to Tad and smashed her tits into his face. It wasn’t his first time seeing or feeling them and she knew he loved to suck on her nipples. As Tad was sucking away, Kelly loosened his belt and jeans and freed his cock.