While attending college, I worked a regular job as a bartender at one of the large resorts near the local theme parks. This job not only allowed me to earn enough money to continue paying for school, but it also allowed me to spend my days at a "tiki hut" type bar watching tourist girls in bikinis all day, while pouring drinks. And even though I did hook up with my share of the girls who stayed at the resort, my most memorable times were with the women who worked with me.
I spent lots of time with several of the girls my age who worked in the food and beverage department as well as the occasional front desk girl. But one of my favorite times was when I took out one of my department's managers. Callie was eight years older than me, had two children that lived with their father, and would often smile strangely when the younger girls and I would flirt with each other. I thought that she was trying to pretend that she did not hear the comments coming from the mouths of her employees since, if she admitted to hearing the sexually charged exchanges, she would have to discipline us for inappropriate workplace conduct. I later learned that her wry smile was a reaction to the innocence of the youth around her who all thought that life was about when you were going to get laid next and not how you were going to pay for the kids braces or make the car payment.
She knew that I had taken out the snack bar girl, her roommate from the front desk, a hostess, and two of the waitresses, all of whom worked under Callie and three other F & B managers. None of these affairs had lasted more than a few weeks. She did her best not to let a horny bartender ruin the ability of half of the females in her charge to do their jobs, but I noticed that her visits to my pool bar became more frequent and I found myself looking forward to seeing her pretty face and smelling her sweet perfume. One time, the conversation turned from how sales were going to who I was dating, which I thought was strange since she usually kept things from getting personal with the people in the department. I can't say that I minded this since I was interested in her as well but was certain that she was way out of my league. Up until now, I had never seriously thought I would get a chance at her. She always dressed in very tasteful outfits, wearing skirts and heels which showed off her tanned legs and trim figure. This particular visit was a memorable one because she was wearing a low cut blue dress that stopped three inches above her knees, and patent leather blue high heels. I found it difficult to concentrate on what she was saying because I kept thinking about what she looked like beneath her clothing. For the first time ever, I found myself wishing she would leave so that I could watch that ass walk away from me with those great legs swinging beneath it.
When she asked if I was still dating Jennifer, it struck me as odd that she would know about it, let alone bring it up at work. Jennifer was the timid little thing that worked as the hostess in the restaurant and besides the fact that she was usually too shy to talk to anyone about her personal life, I couldn't believe that anyone knew that we had gone out. Jenn was still married and her husband was a strung out loser. The poor girl came off as downright mousy and she never talked or dressed like the little hottie she really was. Some of the girls in the restaurant knew how unhappy Jennie was and that her husband was nearly useless at home, but what I didn't know was that Jenn had opened up after our first couple of dates, becoming very outgoing and exuberant about her new found love of sex to her co-workers in the kitchen area. Apparently a lot of the girls on the wait staff had gotten to hear details about Jennifer's clandestine affair with the bartender. The word of mouth turned out to be good for my reputation and future love life.
Callie was direct and pointed out that one of the food and beverage managers "wanted a chance" with me. I tried to act nonplussed, but my youth probably gave away my surprise at her directness. She asked what I thought of having a secret admirer and I instantly thought of Amy, the tall lady who was in charge of the department. Amy had come to one of the after work get-togethers several weeks before and become slightly sloppy, inviting me to take her home after a few hours of drinking. I declined, not because I didn't want a chance at ravishing her tall, former volleyball player's body, but because I wanted it to be "fair" and consensual when and if it ever did happen. I always had a sense of pride about "earning" my time with girls that I slept with and didn't want anyone to regret it later because of alcohol. In my mind, Amy was trying to compensate for her fleeting youth by drinking and acting wilder as she approached her thirties, and it didn't seem sporting to take her up on her offer while she was in that condition. While I did eventually get my chance to date her for a short period, it was not Amy that Callie was talking about. I soon realized that Callie was talking about herself.
Callie talked about how much time she spent at work and how it was a good way to take her mind off of her stupid ex-husband and the fact that he had custody of the girls. It was the usual stuff that people use to lead up to a conversation that ends with them having sex. Then, she brought up the fact that all of the young girls were in a flutter because Jennifer couldn't stop bragging about her nights with me. When she asked how serious I thought it would get, I tried to think of a polite way to tell her that it was not a serious relationship and I didn't see a future. My embarrassment and inability to tell her anything about how I might have felt about Jenn confirmed that it was only a fling, so she continued.
She had heard me telling one of the other bartenders that my fraternity was having a party on the approaching Friday and hinted around that she'd like to come to it. Since I was one of the "older" guys in the fraternity, I figured that it wouldn't be seen as odd if this hot looking lady came as my date. She could easily pass for my age, not that this was a concern, but I was anxious that she might feel out of place around college aged kids. Taking a chance, I asked if she'd like to come to our party. I offered to pick her up and make a proper date of it, but she asked if her friend Rebecca could come also and if so, they would ride together. I figured that if two of them were coming, then she was making sure that her "chaperon" would make sure that it didn't progress past anything other than two co-workers hanging out at a party. I'd met Rebecca and was pretty sure that she didn't like me. I'm glad that was I wrong.
By Friday, I was nearly crazy with anticipation. Callie, after all, was hot. I've always been into ladies that are older than me, and her curvy frame, blue eyes, and blond hair drove me nuts. She was nearly exactly what I looked for physically in a lady, and the fact that she was easy to talk to helped a lot. I hoped that this quality was going to be evident in a social setting outside of work as well, but with Rebecca coming to the party with her, I couldn't be sure what to expect.
I walked around the party, trying to scan the crowd nonchalantly to see if they had arrived yet. Only a few of my trusted fraternity brothers knew that I was expecting Callie and they were waiting to see what she looked like. When the girls arrived, they instantly looked out of place. The eighteen year old girls around them looked like exactly what they were; insecure little girls who were trying to draw attention to themselves with their skimpy outfits and overdone hair. Callie walked in with an air of class and maturity that belied her age. It was obvious to anybody looking at them, that Callie was at least ten years older than even the oldest girl at the party. Rebecca, following in her wake, was slightly out of place too, but being my age, she clearly felt more at ease. I'd never paid much attention to her friend, because Rebecca usually looked at me with disdain. I didn't know the reason for her disapproval of me and frankly didn't care. But on this night, she looked almost as good as Callie and immediately attracted the attention of some of the seniors in the house. During the course of the night, she put a few of them in their places.
Once both girls had something to drink, they started dancing and having a good time. For my part, I watched and hoped that someday I would get a chance at Callie and wished that Rebecca would go away and leave us alone together. Some of the young girls at the party were making faces and whispering into their hands, clearly talking about the two "old broads" as I heard one of them describe them. Callie and Rebecca ignored them, but I could tell that Callie knew what was going on around her. Rebecca was drinking more than her friend and didn't seem to notice or care. I began to feel bad for inviting Callie to a party where she would be so out of place and figured that my hopes were going to go down in flames. After about an hour, Callie leaned in to talk to Rebecca and Rebecca nodded and smiled up at her taller friend. The girls were clearly loosening up from their work place personas.
Breaking off from the dance, Callie walked towards me, smiling all the way. When she finally had pushed her way through the crowd to where I was standing, she asked if I could show her where the restroom was located. We left the large multi-purpose room and headed up a back stairwell towards my room. When I took my key out, she said, "'Awfully presumptuous of you, isn't it?" Realizing that she didn't know that I had a suite with its own bathroom, I quickly explained that I was not making a move on her, but offering her a cleaner, more private restroom. She laughed and said, "Relax, I'm just busting your balls."
She entered my room ahead of me and headed toward the bathroom. I sat on the bed and put a CD on to pass the time, wondering if I would even get a chance at a second date with her after the embarrassment of having young girls making fun of her age. Lost in my scheming, I jumped when the bathroom door latch clicked and I started to stand up, preparing to head back downstairs to the party. Walking out of the bathroom in just her pink bra and thong, Callie looked confidently my way, waiting to see approval in my eyes. I could not have been more surprised at the sight. She was tan all over, her legs looked even longer than I'd imagined, and her toned stomach gave no hint as having carried two children. I was instantly hard. In just her underwear, she looked so vulnerable, where at work, I thought of her as an authority figure. I stood and walked towards her, but she met me in the middle of the room and started pushing me back towards the bed.
"How can you be so stupid?" she asked. "I feel like I've been throwing myself at you and you keep trying to be polite to me. Stop thinking of me as your boss or the older woman; start thinking of me as the nearly naked girl in your room."
The events of the next few minutes passed so quickly, I've never been sure if they actually happened. I was so amazed by what was happening that my mind's eye almost forgot to record the things it saw. I was pushed back into a sitting position on my bed and my shorts and underwear were unceremoniously pulled off of my legs. My hard cock stuck out in front of me and she looked at it for a second, looked down at me, sank to her knees, and grabbed it roughly in her hands.
