This story is a figment of my overactive imagination, specifically of what might have been if I had met a crush of mine back when we were younger. It's a longer story, it kind of just got away from me and I had fun writing out my dreams and fantasies. Anyone participating in sex is over eighteen. This story contains incest, light pee play, panties and scents and more than a little beer. I hope you enjoy it, I'm relatively new at this so please feel free to comment and vote.
Somewhere in suburban Chicago
I was sitting by myself at my favorite watering hole, it's a bit of a dive really but that's why I liked it. There was nothing fancy or kitschy about it; it was a place where the working class meets up to get a drink at a fair price. If you live in a city there's one in every neighborhood.
It was Friday night and it was a fucking bitch of a week so I was in the mood to tie one on. I walked the two blocks from my house and as soon as I walked in I was greeted by name and asked what I wanted.
"Bottle of Bud and a shot of Jack" I replied. I made my way over to the corner of the bar and sat at my favorite stool where I could see the door and most of the bar. Cindy showed up with my drinks, took my money and by the time she got back with my change I had downed the shot and settled in with the beer for a night of nothing but chasing a buzz. My girlfriend was now my ex-girlfriend and I had no plans but to see what a Friday night could bring.
I was halfway through my third beer and getting ready to order another shot when she walked in. I had lusted after Sarah for years but we never seemed to be single at the same time. She was a beauty with long brown hair, or did I see a coppery hue this time. It was hard to tell in the dim light of the bar. Dressed in a nice shirt and pair of slacks that showed off her ass very nicely she looked well put together and comfortable in her own skin. With her blue eyes and a figure that was curvy in all the right places she looked to me like she was built to fuck. If only I had a shot at doing that I thought to myself.
She didn't notice me sitting at the other end of the bar as she ordered herself a glass of red wine. I watched as she took a seat at one of the booths that ran along the side wall of the bar. I watched her take a sip and then take a quick look at her phone. As she slid it back into her purse I figured she was checking the time. She was obviously meeting someone, dashing my hopes that I would finally get a chance at asking her out.
We've flirted over the years, little comments and compliments and she knew I wanted to get something going with her, and I always thought the feeling was mutual but our paths never seemed to cross at the right time. I didn't see her as often as I liked now that we were well into our twenties with jobs and responsibilities. When we did run across each other our conversations were wonderful and filled with stories as we caught up on each other's lives.
I'll never forget the day my sister brought home her new friend from school. I was two years older than their eighteen. They were both seniors and about to graduate. They knew each other all through school but didn't hang out until they found out they were going to the same college and instantly became best friends. I had opted for trade school and was just finishing a degree in machine technology. I had a good job lined up and was eager to get out of the house and on with my life.
I was smitten immediately. Sarah occupied my thoughts and fueled my late night sessions I had with my hand. She was all I could think about. I asked her out but she politely declined, saying that she already had a boyfriend and she was leaving for school in a few months. She gave me a kiss that melted my heart and said we'll see what happens next summer. I heard from my sister that she broke up with the guy just before starting school that fall.
The next summer she was seeing somebody, the summer after that I was, and that's how it went, year after year with neither of us single at the same time. My feelings have never changed though, she was beautiful and smart and doing well in her chosen career. So here we are with me twenty nine and her twenty seven and I was thinking I have to at least say hi before she meets up with her date.
My thoughts were interrupted by the door opening and four guys bursting in laughing and good naturedly ribbing each other. They were dressed in khakis and polo shirts, to me they looked like they were heading to the golf course rather that a night on the town. Even though the sun was going down I noticed one of them was still wearing his straight armed sunglasses backwards on his head. They all got their drinks and wandered back to the pool tables and dart boards.
The place was starting to fill up as it was just past eight o'clock on this sweltering summer night. A lot of people liked to start the night here so they could have a few drinks at a decent price before heading downtown to pay the cover charges and stupidly high prices for drinks. The place would thin out by ten and there would be just the neighborhood regulars and we'd have a blast tying one on.
I looked back over at Sarah who was now on her phone typing madly with her thumbs. She stared at the screen and I watched her roll her eyes and toss the phone back into her purse. She didn't look happy. Just then backwards sunglasses bro decided it was a good time to walk over and hit on her. I jumped into action and grabbed my beer and money off the bar and wasted no time getting over there.
"There you are!" I said in a loud voice. She looked around the bro and her face lit up.
"Bob! It's about time you got here." I slid into the booth opposite her and looked up at sunglasses dude with raised eyebrows. He just sighed and walked back to his buddies who were trying their best to keep from laughing.
When he was out of earshot she looked at me and said "Thanks, when did you get here?"
"Oh, about an hour ago. I saw that you were obviously meeting someone so I kept my distance. Who's the lucky guy?"
She laughed and said "The lucky guy is your sister you goof, were having a girls night but she's late, as usual."
"How late is she running?" I asked.
"She won't be here until eight thirty, she said something about having to work late."
"Good, I have you to myself for a bit" I said and smiled my best smile for her. "So...does this mean you're single?"
"Well, yeah but I just got out of relationship and I'm not ready to jump into another one." She smiled and added "But...if you want to keep it casual I'd love to go see a movie or something with you...wait, are you and Clarissa not a thing anymore?"
"Nope. And it was a four year thing so like you I'm not ready to jump into anything but I'd love to go out with you. You know how I feel about you." She nodded her head and lifted her glass and finished her wine. I finished the beer I had and stood to go get us another. I caught Cindy's attention and she got us each another drink and when she set them in front of me she asked "Getting lucky tonight?" and wiggled her eyebrows up and down a couple times.
"Maybe not tonight but I have a date with her in the future." I knew Cindy was bi and I laughed out loud when she came back with "Lucky dog! Who do I gotta blow to get a nice piece of ass like that?"
"You can start with me" I shot back at her while giving her a grin and saying "Then I'll put in a good word for you!"
"In your dreams Bob, besides you know I don't date people from the bar."
"I know, I know" I chuckled as I went back to the booth.
I set our drinks down and said "Ok then, when can I get in your pants I mean take you out?"
She burst out laughing and came right back with "You can get in my pants tomorrow night if you play your cards right."
