When I first moved to Florida, I took a job as a bartender for several reasons. One, it was what I had done back home in Pittsburgh at a small college bar near Carnegie-Mellon University. Two, I have always been a night owl so staying out late was second nature to me. And third, I tend to be pretty social, always talking to people, telling stories, and flirting with the girls. The constant stream of college aged girls, sorority chicks, and young married women out on the town created a feeding frenzy that kept me chasing tail all year long back in the Iron City. Between the bar's cocktail waitresses and their married friends looking for some discreet action, I felt like I was getting my share.
But in Florida, things were different. When I arrived, I was twenty three, knew no one, and was in danger of yanking off my cock from pulling myself around the room out of lack of company. I fell back on the old adage that says "that you go with what you know" and decided that some of the girls I worked with might be prime candidates for dates. I already knew them, only had to go to work to see them, and several of them were in the age range that I usually went for at that time. Several of the girls that worked in the restaurant were pretty nice looking, but the problem was the crappy uniforms that they had to wear while waiting tables. These things looked like old curtains from a Denny's that was about to be torn down before somebody salvaged them and turned them into the shapeless blouses and skirts that these poor women had to wear. One of my favorite daydreams involved Angela, a tall thirty year old waitress. I desperately wanted to check her out, but that uniform stymied my attempts to ogle her figure.
As I became friendly with Angela, this unflattering outfit was the subject of several of our conversations. She would come to the bar, which had to double as the service bar for the restaurant when it wasn't busy during the day, and take the opportunity to visit with somebody who wasn't demanding anything from her. Her contention was that many waitresses "show off the goods" as a way to help earn more tips but that the blouse and skirt she'd been given did nothing to show off her boobs or legs, both features that she was apparently proud of. The skirt, which hung below her knees, hid her long legs. This coupled with the black athletic shoes that they wore while running busily through the morning rush, left her feeling frumpy and unattractive. As our friendship grew, this uniform and what it did to her self-image was a constant theme of our conversations. As she grew more comfortable with me, she began to ask my opinion of her look. I replied that I didn't know if it was proper for me to tell her what I thought, since that kind of talk is frowned upon in the work place.
"But, I'm asking you what you think. I don't care about suing the resort for the 'hostile working environment' created by the bartender telling me what he thinks about my looks."
"But Angela, it's not the resort's policies that I'm worried about. It's your reaction that concerns me." After she gave me a puzzled look, I continued, "I could say what I think about your appearance, but I don't want you to think that I think of you that way. I try to treat my friends with respect, and I'm afraid that all would end if the truth about how you look to me was put into words."
She leaned towards where I was standing at the bar and with a wry smile said, "Honey, if you were going to get slapped, I would have done it weeks ago. You've been watching me since you started here. I catch you every once in a while, but the other girls tell me all the time about the fascination you seem to have with watching me walk. Do you like my legs?" she asked teasingly.
I must have turned red, because she gave a little laugh, picked up the Bloody Mary that I'd made for some tourist's breakfast, and hustled off to deliver it. I thought that I detected a little extra sway to her hips as that magnificent ass walked away from me across the lobby towards the restaurant. As I started to drift into a daydream about what the tall German girl and I might do if given the chance, I caught a movement out of the corner of my eye. The young girl who worked the snack bar had caught the whole scene from behind the windows of her counter. "Now I know who's been telling her about my secret crush on her." I thought. That little brunette, Paula, seemed quiet and reserved, but apparently when I wasn't around she'd been doing her share of talking with Angela. I filed that away in case it ever came up again and went back to imagining what Angie must look like without the formless uniform that hid her beguiling curves.
Well, her visits to the bar were pretty regular. Even when the diners who ordered drinks with their breakfasts weren't in her section, the other waitresses would give Angela the ticket and let her come pick up the drink so she could spend time with me. Apparently they all were talking about my interest in her over there. I didn't mind because I enjoyed getting to know her.
She had come to America when she was only 15, and after fifteen years and two children, found herself single again and trying to raise the kids on her own with only her older sister's occasional help around the house. Olga had arrived here later and been in the country for less time so that even though she was older than Angela, her English was not as good. Where Angela was tall, slim, and sleek like a German Olympic runner, Olga was softer with more curves to her hips and breasts. But the gruff exterior that she presented always made me cringe when she was around. Her guttural language, unsmiling demeanor, and low tolerance of her sister's friends always made me wonder if it was possible to melt that Teutonic attitude. Olga rarely visited her sister at work and if she did and found Angela in the bar speaking with me, she always made a point to speak in German to her sister and would glance deridingly at me to make sure that I knew that I was being purposely excluded.
Later, when the oft-discussed topic of earning better tips came up again, Angela pressed me for the opinion that I had held back several weeks before. Trying to maintain a gentlemanly demeanor towards her, I again hesitated to describe what I thought of the great body she was hiding beneath that shapeless costume. "David," she said with that beautiful accent, "what do you think? Why won't you tell me what you think about me?"
"Angie, I could tell you, but it might not come out in a gentlemanly manner."
"You can tell me. I'm a big girl. Do you want to ask me out? Do you like my body?" As she said this, she made a little turn that caused her skirt to ride up above her knees. When she turned back toward me, she caught me checking out her legs. "Go on. Tell me that you like my legs...if you do. Don't you think I could earn some better tips if people could see them?"
I told her that certainly she could, but I didn't know if she was willing to wear heals all day while serving orange juice and toast. When she looked at me questioningly, I explained that her long legs would be wonderfully accentuated by a pair of black pumps rather than the cheap black athletic shoes with flat heels that she normally ran around in. If she was to look slightly sexier, she might make better tips from the men who paid their families' tabs in the café. It was like a light bulb going off above her head. She lit up and exclaimed, "That's it; I can do that. I like to wear heels when I'm not at work, but I never have a reason to wear them. I'm going to try it."
The next few days were probably hell on her legs and feet, but they were even harder on the trousers of my uniform. I worked to stay behind the bar to hide the constant hard on that those fantastic legs caused me to develop. Once, when the bar was slow, I considered going into the back store room to jack off. Watching the change in her attitude and the added length and definition of her slender legs had me so horny that if I wouldn't have been afraid of getting caught, I would have covered the back walls with semen.
I was so distracted by trying to catch glimpses of her across the lobby that I completely missed my boss walking in the other door to the bar. Since I was standing in profile to Amy, my hard on must have been very visible in my pants. When I heard the door shut automatically behind her, I was startled and turned toward the sound. There stood the tall food and beverage manager staring at me while trying to suppress a laugh. As she quickly looked away from my bulging crotch, I started to explain but realized that there was no explanation for standing in an empty bar staring at a hot blond with a raging erection. The awkward moment was ended when Angie walked into the bar and announced that she needed two Screwdrivers for one of her tables.
As I mixed the drinks, Angie watched Amy move about the bar as she checked to see that I had done all of my prep and side work. Angie seemed to be watching how our manager moved in her short skirt and high heels. Amy always dressed very professionally but did nothing to hide her awesome figure that she had earned by playing volleyball all through high school and later, on the beaches on her days off. It was fascinating to see how Angela took in everything about Amy's purposeful strut and the way that her hips moved beneath her skirt. I watched this all in the back bar's mirror while I poured the orange juice over the vodka. It wasn't that I thought Angela had bisexual tendencies, but that she was trying to learn by watching how the authority figure in the red high heels and skirt used what natural assets she'd been given. As I finished up, Amy walked closely by Angela and whispered something in passing to her. Angela's smile and downward glance hinted that it might be about me.
