That night, I got dressed up for the first time since the breakup. I carefully selected my outfit--the required shirt that served as our uniform (tight-fitting black shirt with a logo on the left breast, and white laces down the front that looked like the laces on hockey skates), a black skater-style mini-skirt that, when I spun around, floated up to give a peek of my ass, and black thigh-highs edged with red lace to caress my legs. I did my makeup--black eyeliner, dark shadow to make my light brown eyes pop, and red lipstick the same shade as the lace on the thigh-highs--and put my dark hair up in two ponytails. I looked like a sexy schoolgirl, which was my go-to at work. The guys loved it. Plus, it was Saturday so I knew Dru would be there.
Dru was my favourite customer. He and I had been flirting at work for months, nearing a year, and in exchange for the tips he always left for me, I would always make sure to mark a bottle or two of MGD as "chipped" and slide them over the bar to him. One night nearly eight months before, when he was absolutely smashed out of his mind, he tried to kiss me. I dodged it, and reminded him that I had a boyfriend and he lived with his girlfriend, and although he did try for a bit to convince me, he respected that. Plus, he was at least 45, over 20 years older than me. The oldest guy I had ever been with was just one year older than me, and I wasn't sure how I felt about hooking up with a guy old enough to be my father.
Dru had broken up with his girlfriend just a month or so before, and now that I was newly single, I relished the idea of being able to let loose a bit with him. Nothing too scandalous, but I hadn't been kissed by someone new in years and the sexual tension I had with Dru made him a good candidate. Plus, he was old enough that it would be a scandalous story to share with my friends. He was nearly my dad's age, after all. He wouldn't try to date me, wouldn't get emotionally invested, and I could get it out of my system and jump-start the whole "moving on" business.
Sure enough, Dru was there. His team didn't play until 8:10, and it was only 7, so I knew he'd have a bit of time to spend upstairs before heading to the rink. He was there with just one friend, Curtis, though the rest of the guys would join them slowly, I was sure.
Curtis intimidated me. I was smart, and I knew it. But something about the cold way he always spoke to me and observed me made me feel like I was being constantly judged. I cowed when he talked to me, and my attempts at humour always unraveled and made me seem like a blathering idiot. He was hot, so that was probably another factor. Tall, with a lean body and sharp jawline.
That night was busy. I was only on bar for a bit before getting asked to serve, so I ran around the restaurant like a madwoman, taking orders and chatting here and there. Despite the size of the place--we could seat about 75 people when it was busy--there were usually only two girls working the floor, then one behind the bar. Tonight was no exception. I worked in a flurry, and my constant running around made for quite a show with my short skirt, which I usually only wore for bar shifts where I wouldn't be on the floor. Oh well, I was single now and the attention, for once, had no weight of guilt with it. Jordan never said anything about my outfits at work, but his friends would sometimes comment on it and he always made sure to let me know that his friends thought I was too risque. Now I could wear what I wanted, and no one could judge me just because I had a boyfriend.
Just before their game started and they had to leave, Dru called me over and ordered another drink. It was his third beer, which meant he would order at least seven more before the night was over. It had been so busy that I hadn't had a moment to pause at their table other than to drop off their drinks, but two teams had just cleared out so there was a bit of a lull.
"What's the occasion?" Dru asked, with that ever-present smirk on his face. He gestured at me, indicating my outfit, makeup and hair. I always took care to look good at work, but tonight I had dressed almost glamorous, with my dark makeup and fake lashes.
The weird thing about my "flirtationship" with Dru was that I knew he wasn't conventionally attractive. He wasn't very tall, had a bit of a dad bod, and his face was all sharp angles. It must have been that confident air, verging on cockiness, that allowed him to hook up with pretty much any girl he wanted. Before getting in a relationship, I knew that he had slept with a few girls who worked at the Tipsy Penguin, girls in their twenties all the way up to our manager who had to be in her fifties. There was a weird charm to that man that left my panties soaked after our conversations, which often just skirted the line of inappropriate. While nice and polite, he also had a dominant vibe that made my submissive self simper when he turned his attention to me.
"Oh, just felt like dressing up," I replied lightly, striking a pose--popping a leg out in a way that I knew made my skirt lift enough to show off the tops of my lace-trimmed stockings.
"You always dress up, but there's something different..." Dru paused, his eyes skimming my body appreciatively. I was well aware of Curtis observing me at the same time, but I didn't mind. "I know," Dru continued. "No necklace."
For the past years, I had been wearing a cheap resin pendant Jordan had bought me when we first started dating. I never took it off before, and now my neck felt bare. Dru had noticed the necklace when I first got hired, and I had explained it to him. Figures he would be the first to notice its absence.
"Oh, yeah." I tried to keep my tone light, but despite my best efforts I could hear the emotion behind the next words. "Uh, actually Jordan and I broke up. So yeah, no more necklace." I did a fake pout, trying to play it off. "Just means I can dress however I want at work, with no one to get jealous!" I said brightly. I did a twirl. "Isn't this skirt cute?"
I knew exactly what I was doing, and I think Dru knew that. He took the bait and left the breakup topic alone. "Well, his loss is our gain. Especially since you know just how to dress up...or dress down."
Despite myself, I felt my cheeks flush.
"Are you working tomorrow?" Curtis asked. The quick topic change was appreciated--I wasn't quite sure how to respond to Dru in a setting like this. In a more private conversation, I would normally push it a bit further, but I never went quite as far in a group conversation.
"Just in the morning. They put me on the tournament mornings because moms love me," I said, with a dramatic shrug. It was true. The moms who brought their kids to tournaments were a tough crowd, since their husbands tagged along and ended up spending more time at the bar than watching their kids play. While most girls served the husbands and ignored the wives, I did the opposite. I upsold Screwdrivers and Caesars, chatted with the wives about their plans, and gave minimal attention to the men. I served them, but I didn't chat with them. This almost always netted me a bigger tip than if I were to focus on the husbands. Plus it was a nice switch, chatting with the women and relaxing a bit. I didn't have to be "on" with the wives as much.
"I find that hard to believe," Curtis said. "Especially if you dress like this."
"Hush now. I dress perfectly respectable on Sunday mornings. I could go to church right after, and no one would look twice."
"Now I know you're lying," Dru said. He sometimes showed up on Sunday mornings, subbing in on another team that played the earliest slot. "I've seen that ass in pants. You don't need to wear a tiny skirt to make people look."
Now my face was on fire. Apparently news of my breakup had emboldened Dru, who normally didn't speak quite so directly.
He surged on. "If you're only working in the morning, that means you have no excuse. I'm taking you out tomorrow, after your shift. What time are you done?"
Oh God, the way he stated that. I loved when men took control, even if a tiny part of my brain knew it was a bad idea to agree so soon after my breakup. I felt a tingle through my body, concentrated in the apex of my thighs. I found myself smiling at him, cheeks still flushed. "I work seven til noon."
I took a look around the room. Another team, who had just finished playing, had taken a seat in my section. "Don't lose your game, I don't go on dates with losers," I told Dru, as he and Curtis made to get up.
"Oh, I don't lose."
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I was still feeling all hot and bothered as I continued on with my shift. The night passed, and I started serving less beer and more shots. This was when the real tips rolled in. I pocketed them, sifting through the bills when I had a moment. It made the cashout easier if I counted throughout the night...plus I liked to see how much I could make. My goal was always to make more than the week before. Last weekend I had walked away with $750 in three days. This week, working only two days, I wanted to match that, and I was well on my way.
The best way to get tips was to be on the floor, so I wandered around making small talk with my tables. I knew a few of the regulars, so I joked and teased a bit. I never crossed my boundaries though--I would tease and joke with guys, but I never let them lay a hand on me. None of them tried, though some of the other girls had issues with them being handsy. I never let it get that far. Despite my bravado and my sexual drive, I had only been with a couple of guys and I didn't like going anywhere with someone if I wasn't invested in them emotionally to a degree.
Dru and his team rejoined the drinking crowd after their game (which they won), but by then I was back on bar. They were sitting one one of the high-tops in section one, so I still observed them, but I wasn't their server. Just pouring their drinks when the other girls punched them in.
A few times during the course of the night, Dru motioned for me to come over to their table when it was a bit quieter. It was common for the servers and bartender to hang out with their tables--God, I'd even gone to a strip club with a group of customers and coworkers--so I hung out with them when I could. I didn't sit, instead just leaning up on the table. I knew Dru and pretty much the entire team he played on were taking glances down my shirt, seated as they were on the hightop. At 5'3, it was a pretty solid vantage point, I'll give them that. Not that I minded.
I wasn't by any means vain, but I did like my tits. High and firm, my 32D breasts were creamy white topped with dusty pink nipples that were nearly always stiff, it seemed (Poor circulation, I'm always cold). Tonight, the push-up bra I was wearing nearly made my tits pop out of the lace up shirt, and it seemed that the men appreciated it. Despite the fact that I wasn't their server, a few of the guys ordered directly from me and paid cash, tipping anywhere from 20-50%. It helped that their server sucked, so the only way they were getting a timely drink was by ordering from me. The nice thing about working at the Tipsy Penguin was that the bar was on the floor when it came to their service standards, so with any amount of drive you'd be the best server on the floor--or behind the bar.
The crowd slowly began leaving as the clock turned to 1:30. We closed at 2. Finally it was just Curtis and Dru chatting, and I sat down at their table doing my cashout. This was not an unusual occurrence for me, though it wasn't technically allowed. I added together all of my debit and credit slips and cash, figured out what my tipout was, and dropped my cash in the safe in the back. By this time, the other girls had bussed the tables and swept the floors, and I was left to lock up.
"Time to head out, guys." I said as I locked the door to the kitchen.
"One more thing. We have a bet going on, and we need your help," Curtis said, a wolf-like gleam in his green eyes.
"Oh, what's that?"
"Well, I bet that you're wearing red panties to match those slutty thigh highs you have on. Dru thinks they're black."
I flushed and laughed in shock, the sound high-pitched. That took me off guard, especially with the "slutty" comment. I decided to leave that one alone.
"Like I'd tell you guys," I said, still flushed but laughing a bit.
"You don't have to tell us. Show us," Dru said, sliding a $100 across the table. "In fact, if you show us, you'll get all the money. We'll just have the satisfaction of winning."
I looked at the hundred dollar bill. Was it cheap to consider taking it? My tips that night were $334. It sure would be nice to increase that number to over $400, plus I had already taken some risque photos and shared them on my anonymous Twitter account. It really wasn't all that different, was it? Hundreds of strangers had already seen much more than my panties.
