I've never been a player, really. Once I'm with a girl I don't go behind her back. Not out of any moral rectitude on my part, or because I don't find other women attractive. In fact the opposite is true: I find all sorts of women attractive, and I'm not shy about checking out women even in front of a date or girlfriend. But I guess in the end I'm satisfied with one girl at a time. I've always been kinda lazy about putting in the time to get a girl in bed, so I can't really imagine having a regular girlfriend and making the effort to hook up with someone else. But one time, things lined up just so and everything got...interesting.
When I was 24 years old I started bartending at a restaurant. I noticed pretty soon that there were a lot of cute waitresses on staff. Best of all, they were all really cool and down to earth. We all became friends and hung out a lot, and we went out for drinks a lot after work.
There was one girl, though, who was a little more shy. Her name was Rebecca. Not only was she shy, she was really focused on finishing college. So she didn't really come out for drinks with us a lot, and some of the other staff kinda looked down on her for it and said she was a stuck-up nerd. Besides, you know how catty women are. But personally, I really liked her. It might have just been the fact that we always worked together, but I got to know her pretty well and it turned out we had a lot of the same interests. I'd finished college a couple of years before, so I think she liked that she could talk to me about school. And even though she didn't dress very flashy, I could tell she had a nice curvy figure. And hiding behind her glasses was a pretty face, with big brown eyes that made me wild. Most important of all: she was smart, and I've always found intelligence sexy.
Problem was, she didn't have time for any kind of romance. She came from a poor background. She had to work her ass off just to pay the portion of her tuition that he scholarships didn't cover. All her free time was given over to studying, and there was no way she was gonna put her grades at risk. I could tell she liked me too, but she was disciplined. I respected that about her, but in the mean time I was cruising through life on Easy Mode, with zero responsibilities, and enjoying my twenties. So even though we flirted openly at work, it wasn't in the cards for us to start going out
So one night when I went out drinking with the gang after work and a hot little blonde waitress named Kelly sat on my lap, I didn't complain. I found Kelly attractive but we didn't really have much in common, and to be honest she'd never expressed any interest in me. So even though I'd spent plenty of time checking her out, I was surprised when she plopped her gorgeous behind on my lap. At first I chalked it up to her being tipsy and wasn't really planning to make a thing out of it.
Kelly had great legs and didn't mind showing them off, and that night she was wearing a white flared skirt, almost like a tennis outfit. She had a tennis player's build, too, tall and skinny and well-tanned. So when I noticed my hand was near her ankle I got bold and started caressing her leg. She gave no reaction, so I let my hand move further and further up her leg. I had too many drinks in me to be shy, but I let my fingers glide over her smooth skin without much pressure, unsure how far she was willing to let it go. She didn't complain at all, in fact as I put my hand on her thigh just below the hem of her skirt she nuzzled her ass right onto my hardening cock, so I knew it was on.
Once the bar closed and everyone went to their cars, I didn't even say a word, I just took Kelly's hand and led her to my car's passenger seat. She was grinning at me, so I decided to push my luck a little. I made like I was gonna kiss her, but instead I reached behind her and opened the door, playfully pushed her onto the seat, and shut the door. Then I just walked around and got in the driver's seat. When I got in the car she was still grinning but avoiding eye contact. I knew I'd made the right move.
