It all started by the pool at my apartment complex. During the summer, there were lots of girls that hung out at by the pool. Most of them just tanned on the deck chairs. Sometimes they brought a beer cooler. Occasionally they would swim laps or just stand in the pool and cool off. I'm not a perv, but I do notice hot girls. The trick is to just catch a glance but not to stop and stare. That would be so awkward if they caught you staring!
One girl in particular caught my attention at the start of this summer. She was a bit taller than average - maybe 5'7", thin and in great shape. She had cute little abs on a tanned tummy. She had sleek toned legs and a small perky ass. She had the prettiest oval face with long brown hair, long toned arms and perky little tits. Sometimes she wore a black bikini, but she usually wore a cute teal bikini. You could see half of her ass. You couldn't really see much of her boobs because there wasn't that much to see anyway but it was also kind of a tube top. I didn't mind that at all. Most of my girlfriends had been small on top and I liked the thin girls with perky boobies. Basically, she was exactly my type.
She was also out of my league. I'm pretty average looking, not quite 6' tall. I make a pretty good living working at an accounting firm, so I had that going for me. The first time I saw her, she was sitting on a deck chair, playing with her phone. She got up to leave the pool and I looked up at her as she walked past me. I was going to say "hi" but she kind of rolled her eyes at me and I decided not to.
The second time I saw her, it was kind of cold. She was laying on her tummy with her feet crossed and up in the air. I had a good view of her perky bikini covered butt. She had the cutest brown calves and, I'm not a foot guy, but she had long attractive toes and white bottoms of her feet except the balls and heels, which were a cute shade of pink. The contrast between the rest of her tan body was kind of sexy. Just to start a conversation, I asked from a few chairs away, "Is it too cold for this?"
She said, "I don't know." really dismissively so I decided not to say anything else.
The next time I saw her, she was obviously with a guy. He was one of those guys with huge muscles, tattoos and facial hair but no chest hair. Do these guys wax their chests? What is going on with these guys? Anyway, they were sitting on deck chairs talking. I laid down my head like I was sleeping. They got in the pool together. I was trying to steal some glances. It wasn't often I got a good look at her toned sexy abs. The full body view was nice. They probably made out for 5 minutes. Then they got out of the pool, hand in hand, gathered up their stuff quickly and left the pool area. I imagined they went up to her apartment to have sex. Lucky guy. That was the first time I actually cared enough to jack off to her later that night in my bedroom.
I thought about her while I was jerking off for the next two weeks, but then I went back to porn. Pool season was pretty much over so I didn't figure I'd see her for a while - and definitely not in a bikini. It didn't much matter anyway. She was out of my league, had a boyfriend and had shut me down twice before I could hardly even say anything. I hadn't thought about her much lately when I saw her again in late September. She was sitting on the stairs leading up to my apartment. I was walking in from the parking lot after work. She was looking at her phone and seemed frustrated. She had a duffle bag or something sitting by her.
I acted like I was going back to my car to buy time to think of something to say. Even if she has a boyfriend, I still want to make a good impression on a hot chick. Obviously, that was not enough time to think of something clever because I said to her, "Hey, the girl from the pool?"
"What?" she barely looked up. She was wearing white pants and a pink short-sleeved shirt.
"You were at the pool, like, alot this summer. Me too."
"Oh yeah?" She said, still not really paying me any attention.
"Yeah, almost every day. Gotta take advantage of the pool right? Are you going on a trip or something?" I said, pointing at her bag.
"No, um, no." was all she could say. Christ, that went nowhere. At least she half looked up. What else could I say?
"So what are you doing now that the pool's closed?" I asked.
"Nothing, just working." Then after a long pause, she looked up from her phone, gave me a big smile and said, "I'm Ashley, by the way. What's your name?"
"I'm Matt, so you live in this building?" There were 8 different buildings.
"What are you doing, right now, Matt?" Ashley crossed her arms and looked right at me.
"Nothing, just getting home from work. Maybe hit the gym." Hopefully that would impress her that I mentioned going to the gym.
"Do you want to go to dinner, Matt?" Ashley asked, leaning in with her warm smile and big brown eyes. I thought it was weird that she went from not even looking at me to wanting to go out to dinner with me in the space of 30 seconds, but this was my chance to make a good impression and win the girlfriend of my dreams.
"Yeah, sure, but I thought you had a boyfriend?" I blurted out.
Good thing Ashley took it in stride, "Oh, we broke up." she said nonchalantly. Then excitedly asked, "Where are we going to dinner?"
Minutes later, I had changed my clothes and we jumped into my almost new, black Ford Explorer. I imagined that it's a cool, impressive vehicle. She put her bag in the car. She claimed she didn't want to go all the way upstairs to put it away. OK, whatever works. We went to a sushi place. I swear she hung on my every word. Then she talked me into going out drinking. It was a Thursday, so that's not really what I had in mind. But I didn't want to disappoint her and I'm talkative and hopefully charming when I drink. We had a great conversation. She likes my favorite MLB team, my favorite NFL team and my favorite college basketball team. She liked all of the movies I mentioned and all my favorite bands! This was truly the perfect girl!
The bad part was she kept ordering shots. Shots kill me! She just kept taking them though. I wanted to keep up! I should have just let her win that contest. One minute we were in the booth making out. Then I blacked out and the next thing I remember, it was the middle of the night and I was hugging the toilet. I remember Ashley was there asking me if I was OK and asking if I needed anything. Then I remember waking up with a headache. I stumbled out of the bedroom and you'll never believe what I saw.
Ashley was there in black heals, a dark blue bra and panties with my "Kiss the Cook." apron on. She handed me a cup of coffee and said, "God morning roomie. I think you're going to need this." There was also pancakes ready to go and sausage links sizzling on the stove. She had the biggest smile on her face.
"Yeah, my head hurts. It's so nice of you to cook me breakfast. I think I blacked out. What happened last night?" I knew damn well I blacked out, by the way!
Ashley explained, "We went to Clancy's and you were taking down shots like a champ. Then we went to Cliff's and you had a couple Long Islands. I bet a guy 20 bucks that you could chug that last one, so thanks for winning me 20 bucks. After that you didn't look so good. One of my friends just happened to be at the bar and he drove us home."
"Oh my God, did anything happen when we got home? Did we have sex?" I asked. Wow, that was smooth.