I Finally Found My Way

Story Info
Ann finds love and makes a mess of it.
13k words
4.29
31.8k
39
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Bh76
Bh76
2,760 Followers

John Clayton and Jack Reilly were sitting in their golf cart, in line, waiting to tee off on the 18th hole of Medinah #3. Medinah is a private course with invitation only membership and Jack sponsored John's membership. They were playing John's first round as a full member.

John was, at the time, a 25 year old investment banking whiz kid. He met Jack 3 years before at a Whisky tasting event and convinced him to give him a shot to earn Jack's portfolio. Jack took a liking to the young John and gave him a shot. In the three years they've known each other, John had increased Jack's already substantial wealth by 20%. They became regular golf buddies and friends in that short amount of time.

"John, you should come to the house today for lunch. Alice is whipping up her famous potato salad and we can throw some burgers on the grill. I have a bottle of Macallan 25 year Sherry Oak I'm dying to open and need an excuse."

John laughed and said, " You had me at Alice's potato salad, but the Scotch is a deal maker. I'm not sure we'll make it in time for dinner, let alone lunch, with this back up holding us down though."

Jack smiled and said, "Yeah, but look around son. There's no finer place to be stuck waiting. This course is beautiful and now that you're a member, you can enjoy it anytime."

"You bet, and I can't thank you enough for pulling strings for me. I know they weren't excited by a 25 year old, punk kid applying."

Jack laughed and said, "C'mon, I could make a strong case that you take life and business more seriously than I do and certainly more so than when I was you're age. I certainly didn't have your net worth at your age."

"I suppose, but I've always been a bit above the fray. I'm just too goal oriented and I have every intention of not wasting my 20's partying. I'd rather retire earlier and live well than work longer. Don't get me wrong, I'm not a workaholic; I have made myself quite a life already, picking stocks like I do, and I fully intend to enjoy the finer things. In fact my next goal is to find a good wife and start a family. I just worry about gold diggers."

"Well, you can avoid gold diggers by keeping your finances close to the vest. You live in a nice but modest house and drive a nice car, but you're certainly not showy. You can keep your money secret until you know you've found the right one. Hell, even then you can keep your money hidden. I could show you some tricks if you'd like."

"Thanks Jack. I'll take you up on that. Come on, we're next on the tee."

**********

Jack's wife Alice and their daughter Ann were chopping veggies and preparing the side dishes for lunch. Alice is in her late 40's and could pull of being Ann's older sister rather than her mother. Ann is 22 and fresh out of college.

"Mother, I don't mind helping out, but I'm going to go shopping. I have no desire to meet one of dad's stuffy friends. There's no reason for me to hang around with the old people."

"Old people! Watch it missy, I'm not even 50 yet. Your father wants you to have lunch with us and you will do so. You came home only three times after you left for school and now have been back for a week and he's hardly seen you. Besides, I know John and you'll be pleasantly surprised. He's under 30 and gorgeous."

"Oh! I get it now. You're setting me up. Well, I have no desire to date anyone so you're wasting your time. I am young and have no desire to be tied down just yet," Ann replied tersely.

"Well you better not think you can come home and continue to act like you did at school," Alice said.

"What are you talking about, Mother?"

"What? You thought we didn't know about your partying and the trouble you got into at school? Your father and I kept tabs on you and even wrote a check or two to keep you from serious trouble. You think the school didn't let us know you were about to be expelled for that hazing incident? You think we didn't know that you spent half your time there hungover and the other half drunk? We argued about it, but decided to let you get it out of your system and now is the time to settle down and join the real world. Get a job. Find a husband. Give me grandbabies."

"You're unbelievable, Mother. I will settle down when I am ready to, and not one moment sooner. You'll need to wait a long time for YOUR grandbabies."

"Enough now, Ann. They'll be here soon. We'll discuss your future later."

*******

John stopped to pick up some flowers for Alice and an expensive bottle of Pinot Grigio to have with lunch. As he pulled in the drive he could smell the coals burning, so he walked around to the back of the huge house.

Jack and Alice have a huge back deck area with three levels, a concrete patio surrounding a large in-ground pool and hot tub, a perfectly manicured landscape design and garden, and a four seasons room that has it's own climate control. His grill is nothing short of amazing. It is both gas and coal/wood burning with a cooking surface as large as John's ever seen. Jack loves to cook and he loves to have backyard barbecues at least once a month.

"Hey Jack, you back here?"

"Yeah John, come on up. Oh, you'd better take those flowers into Alice. She's gonna love 'em. I'll introduce you to Ann too. She's home from college all graduated up."

"Sounds good. It's funny that I haven't met her yet. I always thought you were hiding her away. You've never really talked much about her."

"Well, she didn't come home much from school, but she's back now so come on, I'll introduce you."

"John," shouted Alice. "How are you? Oh are those for me? Ann grab a vase and come in here."

"Hi, Alice," John said, handing her the flowers and kissing her cheek. "Thanks for having me over, I'm looking forward to some of your famous potato salad."

"You're in for a treat then. Ann and I made a big batch and I'm sending some home with you."

At that moment Ann walked in and caught John's eye. He was immediately stricken by her. She was stunning with long brown hair in a pony tail, tall in flat sandals, decently endowed breasts, long legs showcased by tastefully short shorts, and a narrow waist. Her lips were full and her eyes were a sharp blue. She wore no make up and didn't need it. Her high cheek bones and perfectly proportioned nose made her look as if she could have stepped off a runway in Paris.

She took notice of John as well. Tall and well built, with brown hair that was a bit long but still fashionable. She couldn't help but notice the size of his hands when they were introduced and wondered if he packed a good sized sword in his khaki shorts.

"You must be John. I'm Ann, welcome to the Reilly family set up."

John laughed and said, "Nice to finally meet you. I wasn't aware you were home until five minutes ago so, I assure you, I'm not in on it."

Ann shrugged and walked away to put her mother's flowers in water.

Jack said, "Hey, come on out and help with the grill, John. Alice, can you and Ann set up the sides and table setting? It won't take that long to cook up the meats."

John and Jack cracked beers and stood in front of the grill enjoying the sun. Jack never let anyone cook at his house, but enjoyed having company while he fiddled with the burgers and veggie skewers.

"What do you think, John? She's a looker huh?"

"She's lovely, and I guess she's right. This is a set up hmm?

"Oh, don't be like that. Think of it as nothing more than an introduction. The rest is up to you kids."

Ann had come out with table ware and John couldn't take his eyes off of her. Alice opened the sliding door with some side dishes and noticed right away. She smiled inwardly and thought everything was going according to plan on John's end, now Ann needs to get with the program. Certainly someone as steady as John would be the perfect one to settle Ann down. She could certainly do worse than the handsome and rich upstart. Alice herself harbored a little crush on the young friend of Jack's and Jack always got a little bit of extra spice in bed on days John came around.

Ann looked up and noticed John watching her. She smiled flirtatiously and said, "Hey sport, take a picture..."

"It'll last longer," finished John. "I just might ya know."

Ann gave a bit of extra wiggle as she went back into the house. Alice followed her in and asked, "What do you think of John?"

Ann sighed and said, "He's cute."

"Cute?" Alice shrieked. "I have to change my panties twice every time he comes over and smiles at me."

"Mother! God..."

"Oh stop it. I may be older but I'm not dead."

"Ugh!" Ann gasped and took the wine glasses out to the table.

*********

"These burgers are amazing Jack. I have to get your spice recipe. What do you use?" John asked.

"Nuh uh, bud. That's a family secret." Jack said with a smile.

"You'll have to adopt me then. I must know."

Alice laughed and said, "Adoption isn't the only way into the family you know."

"Oh for Christ's sake, Mother," Ann sighed and left the table carrying some plates in.

Alice grinned innocently and said, "What?"

John rose and started grabbing things to help clear the table.

"No way, buddy. We've got Whisky to open and I have some more of those Bolivars I know you like." Jack said. "C'mon and let's hit my study."

John complied, but carried some dishes in with him anyway.

In the study, Jack handed the cut Cuban cigar to John and said, "I have a box of these for you. My brother sent some back for me and I know they're your favorite."

"Thanks. Yeah, I love 'em. I guess I owe that to you, don't I? You gave me my first cigar when I passed your test."

"Ha. I figured that hundred grand was gone when I gave it to you to play with. Imagine, a barely out of school kid, telling me that he could steal me away from my long time portfolio managers. You had balls kid, but were never arrogant or cocky. You reminded me of myself and now look at you. You've built a client base that is the envy of 20 year industry veterans."

"I owe some of that to you as well my friend. You talking me up among your friends practically built me up by itself. There's no better way to get business than referrals from Jack Reilly. Now where's that Scotch?"

"Hey boys, when you're done stinking up the house, Ann has dessert ready." Alice said coming into the smoky room. "She whipped up a strawberry shortcake with fresh strawberries, not that jarred crap."

"Sounds good, hon, be right there." Jack said annoyed. "Let's have a quick belt and take the cigars out back, it's too nice too sit in here anyway."

John knew that Jack wanted him to be around Ann as much as possible, and Ann would certainly not join them in the smoky room they were chatting in. He smiled as he was glad Jack made the suggestion. He also wanted to be near Ann. It was like he was hit by a lightning bolt when he saw her.

After dessert on the deck was finished, Alice said, "Jack help me bring this all in. I also need to show you that issue with the bathroom, I told you about."

"Huh? Oh, right baby. No problem."

Ann laughed and said, "Subtlety was never your strong suit, Mother."

Alice stuck her tongue out and followed Jack into the house, leaving the young ones to themselves.

"Well?" Ann asked a befuddled John.

"Well what?"

"Your story. I want to hear how you befriended my old man and why my parents think so highly of you that they set all of this up. I mean, I haven't barely been home a week and they're pushing you on me."

"Oh, well I am your dad's investment broker. We met a few years ago and I convinced him I could make him more money than the guys he was using at the time. I have a knack for picking winners in the market."

"Gotcha, you're a money savant. You must be pretty loaded."

If her parents couldn't buy and sell him a hundred times over, his gold digger alarm would have gone off, but he knew about her trust and knew she had no need for his money.

"I've done pretty well, but I have a long way to go before I would call myself wealthy. Anyway, your dad and I hit it off right away. He's been sort of a mentor for me. My dad died when I was twelve so, I take advantage of any wisdom Jack is willing to spare my way.

As he started winding down his work life, he realized that he didn't have many hobbies. We started golfing together and have had a regular tee time for the last two years."

"So what do you do for fun, stock boy?" Ann said with a wry smile.

"I golf and that's pretty much it."

"No wife or girlfriend?"

"Nope."

"Work's you're wife huh?"

"No, I work hard, but it's not my life. What about you. You're freshly graduated, what are your plans now?"

"I don't know. I mean at some point I'll need to get a job and grow up, but I'm not rushing that."

"I see, daddy's princess wants to party a bit and live at home for a while."

Ann snapped at him for that, "Hey dick. Watch it. I just don't want to jump right into the 9-5 grind a week out of school."

"Easy killer, I was just kidding." John defended. "What did you degree in?"

"Art History. I wanted to work in a museum or showroom, somewhere I can leverage my love of Art as a career."

"Nice," John said thinking she has no intention of ever working, "You'll always be surrounded by beauty."

"See, you get it, but I'm in no rush. I'll settle down eventually, but I'm going free and easy until then."

John knew he should run from this girl who had no ambition, no goals other than live off of daddy's teat, but he was drawn to her beauty. She could be a worthy project, he thought. He could get her to settle down and if she was anything like Alice, would be great wife and mother material.

"Got plans for tonight, Ann?"

"You work fast, huh stock boy? No, I'm free."

"How about dinner? We could hit a club after? I'll pick you up at 7."

"Okay, 7 it is. No stuffy steakhouses or supper clubs. I want to go somewhere trendy."

John laughed and said, "Sure, I know just the place. If you'll excuse me, I need to head home and get ready. I'll see you soon."

He made his way into the house and saw Jack and Alice at the kitchen table, smiling at him expectantly.

John laughed and said, "I'm taking her to dinner tonight."

Alice high fived Jack and said, "I love it when a plan comes together."

"Whatever, you two. Thanks for lunch and I'll see you later."

********

John was excited for their date as he rang the doorbell, but he was not prepared for how beautiful Ann was when she made herself up. When she opened the door he was speechless. She had a sexy LBD on that went to mid thigh and hugged her curves. She wore black CFM heels matched with nude stockings. He couldn't tell if they were thigh highs or pantyhose, but he approved.

She was happy with how well he cleaned up also. He wore a black sportcoat and slacks with a crisp blue shirt. He smelled fantastic. She loved the clean smelling and understated cologne he was wearing. Nothing pretentious for him.

"Ann you look amazing," John said after getting his breath back.

"You're not so bad yourself, stock boy."

He took her hand and led her to his car. "Very nice, John. A BMW M850? I approve."

John chuckled and said, "Good, I borrowed it. My old Ford Escort is in the shop."

She smiled at his little joke and got in. John noticed that they were thigh highs and smiled as he shut the door. He saw Alice and Jack looking out the front window and waved as he walked over to his side and got in.

"So what's the plan, Stan?" Ann asked.

"I figured downtown Chicago. Temporis for dinner and Joy District for dancing."

"Mmm, very nice. Spoiling me on the first date. Excellent idea."

*********

Sitting down to eat the trendy Indian food, they talked easily about everything and nothing. John impressed her by ordering wine for each course of the meal. "He's definitely not like the immature frat boys I've dated." she thought.

"John, you seem older than 25, more mature than I expected. How is it that no one's snatched you up?"

"I guess it's like I told your dad earlier. I'm really goal oriented and don't want to waste my 20's. I look at this time as prime earning years rather than party years. With that kind of outlook, I figure I can retire earlier and really enjoy life later. I've always thought that traveling the world and fine dining and drinking were a better deal than clubbing 4 nights a week. As for how I'm single? I guess the right girl just hasn't come along yet."

"You don't like night clubs, huh?" She asked trying to hide her disappointment.

"No, I didn't say that. We're going to my favorite club after dinner. I probably go there a couple of times a month, but my life isn't all partying. I figure there's a place and time for blowing off some steam, but that doesn't require forgotten weekends and binge drinking. I kinda like the axiom 'drink better, not more', ya know. I do dance a bit, so don't worry too much about me being a stick in the mud."

She felt better knowing he had a favorite dance club and it was one of the better ones in the city. She felt he was a bit stiff though, and hoped some drinks would loosen him up.

After dinner, he got them seats in the VIP section of the multi-level night club and ordered a bottle of Champagne. He went to that club regularly with his friend Ace in the recent past and if you didn't dance you had less of a shot with the ladies, so they danced. It was like shooting fish in a barrel for the handsome bachelors, especially when John threw his money around. They always found companionship for the night, but those days ended when Ace started dating his girlfriend Jenny.

"Wanna dance, stock boy?" Ann yelled over the loud, thumping music.

John nodded and to the floor they went. Ann was a very sexy dancer and had no problem grinding on John. He enjoyed her ministrations as was evidenced by his growing bulge. After about 20 minutes and having worked up a sweat on the crowded floor, she pulled him back to their table for a rest and drink.

"You surprised me stock boy. I was ready to peg you as a sit and drink type, but you can move."

"Thanks, I guess. I manage to get out a bit."

A man walked up to the table and asked Jenny to dance. John thought this was a good test for her and he shrugged when she looked at him for approval.

She said, "Sure Cowboy, let's go."

John frowned when she failed the test and watched her walk away. He was watching her dance very closely with the guy when his friends Ace and Jenny walked up and sat down in his booth.

"What's up Johnny boy?"

"Hey guys."

"Here on a date?" Jenny asked.

"Yep, black dress," John said pointing over to his date grinding her dance partner.

"Ouch, failed the test huh?" Ace asked while Jenny frowned.

"I told you before that's a silly game you play. You should just say no when they ask." Jenny said.

"You passed." Ace said.

"Yeah, but I loved you from go. I was special."

"Yes you are. We're on our way out John, if you want to meet up later, give me a call."

"Sure Ace, have fun."

As Ace and Jenny walked away, Ann came back to the table. "Ready to go?" John asked standing up.

"So soon? It's early yet."

"I'm feeling a bit tired. I've been up since 5."

"Okay," Ann said sadly.

The ride home was silent as John thought about Ann not only agreeing to dance with someone else, but the sexy way she danced with him. He thought that if she liked him or felt there was a potential for future dates with him, she wouldn't have danced with someone else on their first date and especially not that sexily.

John pulled into Ann's driveway and walked around to open her door for her. As they were walking to the door Ann said, "Wanna come in for a drink?"

John said, "No thanks, I'm gonna get to bed, I'm beat."

"Oh, okay," Ann said. As she walked up the steps to her front door, John stopped on the first step.

Bh76
Bh76
2,760 Followers