One Lucky Man

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."

She caught me off guard with that statement and was at a loss for words for a few seconds and then she added "Oh come on Bob, we've both been wanting this for the better part of a decade, we gotta do it at least once while we're both single."

I regained my composure enough to nod my head and say "I absolutely agree, you left me speechless there. I was expecting to have to work for it but hey, I'm in!"

She winked at me before saying "How about you come over to mine at six o'clock and I'll have dinner ready. We'll work things out from there."

"Works for me, are you still in that apartment on Toughy?"

"No, I'm actually in the process of buying my Uncles house not far from there on Hamlin, he's giving me a deal. I moved in about three months ago. I'll shoot you the address."

She started typing on her phone and just then my sister burst through the door looking like a million bucks. I've always thought my sister was hot, long brown hair with a smile that lit up the room and showed her cute dimples. I knew she worked out regularly and had a nice firm ass. It's been a number of years since I lived at home and raided her laundry hamper but back then her tits were thirty four B and they look perfect on her five foot seven inch slender frame. I also used to snag her panties for some lees than brotherly purposes and wondered what she was wearing under that nice pair of jeans and a top that looked like a corset with a light jacket. I've secretly wished she wasn't my sister for a long time.

She took a quick look around the bar and spotted Sarah and me and came right over. Sarah scooted over to let her sit on her side of the booth. Set sat down and smiled at me and said "I don't remember you being invited to girls' night."

"I wasn't and I won't stick around Lisa, I was keeping Sarah company while you were busy being late."

"Bob save me from having to shoot down the guy with the backwards sunglasses over there." Lisa looked over and cringed and said "Oh he's so not your type."

"Right? So as a reward I'm making him dinner tomorrow night." I looked at my sister and smiled a fake smile with as many teeth as I could show. This cracked them both up, when the laughter died down Lisa looked at her friend and shook her head.

"You're finally going to fuck him aren't you?"

"As long as doesn't fart at the dinner table then yeah." That brought on more laughter and I thought to myself this could be a fun night if they didn't already have plans. My sister and I have always gotten along well, the usual sibling arguing growing up but we always had each other's back. We could always talk about anything and talked to each other at least once a week. I was very protective of her until she went off to college and since then she has matured into a wonderful woman and is kicking ass in her downtown job in finance.

Lisa said "I'm happy for you guys, I know you've both wanted this for a long time. But you're mine tonight Sarah!"

"Oh really? That would be a sight to see...can I watch?" That earned me a swat on the arm as Lisa reached across the booth to playfully slap me.

Sarah chimed in with "No, you may not watch me eat your sisters' pussy." I looked at her to see if she was joking and saw her cheeks were bright red.

"Sarah! Don't say that shit in front of my brother!" She was red in the face also and laughing.

I pressed on with "So you two have done that before?"

"We were really drunk and it was only once" Sarah said. "And she passed out in the middle of the fun so it doesn't count."

I replied "Well give me a call later if you need somebody to keep you awake. I would do that you know, as a public service. I'll also bring drinks and snacks if needed because I'm a full service kind of guy."

They both burst out laughing and I took our empties up to Cindy and got us another round. By the time I got back the laughter had died down and they were talking low so I couldn't hear much, but I did hear my sister say "No, not tonight" and they both turned to face me.

"So where are you guys going tonight?" I asked.

Sarah answered "Well, we're going to have a couple here then Uber to a bar I know. We haven't been out in a long time and I feel like dancing."

"Sarah wants to know if you want to come with and I told her no, you have plans." My sister said, "You do have plans don't you?" She was giving me a look like she didn't want me there tonight. I knew that look, almost pleading with her head cocked to the side. It was a look she used when she wanted something done, or wanted to get her way. I got the hint.

"Yeah, you know...I don't feel like going dancing tonight. I have to be up early to get errands done so I can be on time for dinner with some hottie." I looked right at Sarah who looked disappointed and flattered at the same time.

Lisa said "Well it's settled then; we'll have a couple and head out."

"Be careful out there, ok. Got your spray?" I asked.

Sarah dug around in her purse for a couple seconds and came up with a little canister of pepper spray. Lisa shook her head yes indicating she had hers too. While Sarah was putting it back in her purse Lisa caught my eye and mouthed a silent "Thank you." I gave her a look of confusion and she gave me a silent "Call you tomorrow." I nodded my head. After another drink it was time for me to leave them to it so I stood and said my goodbyes. Sarah nudged my sister and said "Let me out."

She came over to me and gave me a big hug and whispered in my ear "I can't wait for tomorrow, we're gonna have so much fun!"

I hugged her tight and said "I've been looking forward to this for years, can I bring anything?

"If you don't want to drink wine bring your own libations, other than that I got it covered."

I said "Ok, see you at six." I gave her a quick peck on the lips and moved to hug my sister. We hugged briefly the way family members do, more of a formality than anything. We've hugged that way all of our lives and it came easily. I glanced at Sarah who was looking the other way and said to Lisa, "You cock blocked me?"

"I'll explain tomorrow." She said. We said our goodbyes and I walked over to reclaim my favorite stool. It was thinning out now, half the bar had left for downtown where nothing really gets going until ten or eleven. Cindy caught my eye and asked if I wanted another. I said yes and another shot.

She brought me both and asked "Where are they going, and why aren't you going with them?"

"Lisa cock blocked me and said she'd explain tomorrow. As for where they are going, I forgot to ask. They'll probably go somewhere on Clark, it's not that far of an Uber. If I know my sister they'll end up in the West Loop."

"Ugh" Cindy said. "Thirty bucks for a glass of cardboardeaux? Not me."

"They'll only pay for the first one; guys will be swarming around them all night. You know how that is, being the hottest lady in the bar and all."

"Flattery will get you nowhere Bob, but thanks for the kind words."

"My loss" I said to her back as she scurried off to the other end of the bar. I loved to watch her walk away, she was in great shape.

I had a couple more and walked home at eleven thirty with a nice buzz. My mind was filled with happy thoughts of what would transpire the next day and I realized I was actually a little nervous. I've wanted this for so long and I didn't want to screw it up. Thanks to the alcohol I was able to get a good night's sleep and woke up with only the slightest of hangovers. Some coffee and a light breakfast took care of that and I was off to run errands.

I was leaving the grocery store when my phone rang. It was my sister so I hit the button on the steering wheel and said "Hey cock blocker!"

She laughed and said "I did not cock block you, you're getting it tonight. Believe me, it's all she talked about for an hour after we left you, I finally had to tell her to shut up about it."

"Ok, but what was that all about last night?" I said with amusement.

"Look, I'm really sorry about that but I already had a surprise planned for her. I invited two of our mutual friends to meet us at a bar on Clark and I wanted it to be a real girl's night. And it was because we had a fucking blast!"

"I'm glad you had fun. Were you able to fight off the guys hitting on you? You two were looking hot last night." It took her a few seconds to answer and I was about to ask if she was still there, then she said "Sarah and I pretended to be together. The other two were just ruthless, shooting them down with snarky remarks that made them walk away with their tails between their legs. We had so much fun... You really think I looked hot?"

"Of course I think you looked hot sis, I can say that can't I? It doesn't bother you does it? I can stop."

"No!" she almost yelled as she cut me off. She lowered her voice and said "I mean...I like that you think I'm hot...I...shit I don't know what I'm trying to say here."

This piqued my interest and I couldn't let it go. "Just say what's on your mind Lisa." I softly replied.

"I can't think right now, I'm so hungover all I want to do is eat something and go back to bed for a couple hours. What are you doing tomorrow, up for some company?"

"I'll be in the garage all afternoon, come over whenever."

"Ok I'll be over at one. We'll talk then, have fun tonight!"

"I hope to. See you tomorrow then."

We hung up about the time I was pulling into my driveway. I got the groceries put away and sat down on the sofa and thought about the cryptic conversation I just had with my sister. Harmless flirting and good natured innuendos are one thing but something in the way she said that, something in her tone had me wondering. Or was I reading too much into it. Hopefully I would find out tomorrow.

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I busied myself with laundry and housecleaning and soon enough it was time to get ready for my night with Sarah. I showered and put on a decent button down shirt and jeans then I grabbed a twelve pack out of the fridge along with the bouquet of flowers that I got at the grocery store. They were cheap but pretty and I hoped in this case it really was the thought that counts. Sarah lived about twenty minutes from me a couple suburbs over. I pulled up to her house with five minutes to spare, I set the beer down so I would only be holding the flowers when she first saw me and rang the bell.

She answered the door and broke into a huge smile when she saw the flowers. She looked fantastic dressed in a yellow sundress that showed lots of leg. Her hair hung loosely and she had minimal make up on, she was stunning and I told her so.

"Wow, you look amazing. You're so beautiful Sarah, you take my breath away." I was laying it on thick and she knew it.

She rolled her eyes but I noticed her cheeks were coloring up and she said "Thanks, and thanks for the flowers, let me get these in some water. Come on in." Make yourself at home."

I never know what to do when somebody says that so I just watched her ass in the dress as she disappeared around the corner into the kitchen. I took my shoes off and followed her with my beer and put them in the fridge while she finished with the flowers and put them on the counter. Then she spun around and walked over to me, threw her arms up around my neck and drew me in for a kiss.

At about five feet five she was a good match for my five eight and I pulled her close. Our lips met and we started to slowly make out. I tickled her lips with my tongue and she readily accepted it. We were making out with passion now and I slid my hands up and down her back, over her ass and back up. She broke the kiss and said "How hungry are you?"

"I could eat...you if you want." I looked into her eyes and saw the same eagerness as I was feeling.

She said "That sounds good. I'm gonna be blunt here Bob, I want to fuck. I've been waiting too long for this and I've been wet all afternoon, I had to change my panties once already."

"Ooh I would love to smell them, lead me to your hamper!" I joked.