Thursday
"I'm lucky to have such good friends, Mary." Tommy told Mary, after she asked who would be tending bar the next night at Nathan's cigar party, since his broken hand would prevent him from working the private side gig with her.
Tommy had just broken his hand an hour earlier, rendering him unable to bartend at the party his longtime friend and customer, Nathan, was throwing the next night. Nathan, a real estate lawyer was throwing the party to impress a big developer with whom he was seeking a lucrative contract. Tommy, Mary's lover, had invited Mary to work with him in greeting guests and serving drinks. They were to split the tips.
"My downstairs neighbor, Zach, will tend bar." Tommy said. "You met him two weeks ago over my place. I just got off the phone with him. He's a longtime bartender and he said he's really looking forward to working with you!"
"Really?" Mary answered, intrigued, yet horrified, that she would be working a three-hour shift with Zach, who a day earlier had rudely surprised her with a cum facial.
"So, here's my plan." Tommy started. "You take the train downtown to the gig. When you finish, at nine pm, Zach said he will be happy to drive you back here. Then we can still spend the night together!"
Mary was troubled, hearing that Tommy had talked to Zach about driving her back to his place, without talking to her about it first. Tommy's plan had her working closely with Zach to serve drinks and then riding back to Tommy's with him.
She was not happy that she would be spending all this time with Zach. But she did not want to tell Tommy that she had fooled around with Zach and could think of no compelling excuse or reason why she would not accept a ride from him.
"Okay." Mary said to Tommy. "Let's see how the night goes with Zach."
"What do you mean?" Tommy asked quizzically. "Zach is an experienced bartender and he said he thinks you'll be great in the hostess role."
"He said that?" Mary asked, disturbed with herself that she even cared what Zach thought after what had happened the day before.
"Absolutely!" Assured Tommy.
"Ok, Tommy. I will come back to your place with Zach. You'd better be home resting your broken hand when I get there!"
"That's great, Mary! You two will clean up in tips. I can't wait to hear all the details when you get back to my place!"
Friday
On Friday morning Mary was up by 8:00 am and sprang into action. She got into the shower, shaved her legs and all around her pussy. She had an appointment for a manicure and pedicure at 10:00 am and was having her hair done at 1:00 pm.
Mary did not get home from her hair appointment until 3:30 pm. She had to decide what to wear for that evening. She finally settled on a short, black, low cut cocktail dress with spaghetti straps. She picked out a pair of black open toed sandals with 4-inch heels to go with it.
She drove to the local train station and caught the 4:59 pm train to Center City. While on the train, Mary used her phone to read Nathan's bio on his business website. She studied his picture and still could not remember him, despite Tommy's assurance that they knew one another from many years ago. She reached Nathan's town house with time to spare.
When Nathan, age 59, bald, slightly overweight, with a beer belly, answered the door, his eyes lit up. It had been years since he last saw Mary. She looked as hot as ever in her sexy, short, black cocktail dress that showed a lot of skin.
"Nathan!" Mary said, giving him a warm hug, before stepping back to look at him. "It has been too long. You look great! You must work out! It really shows!"
Nathan blushed. He was so happy that Mary remembered him and thrilled that Mary would be greeting guests and serving drinks to a group of men he wanted to impress.
"Mary, you are too kind. It is good to see you again after all these years!"
"I agree! It's terrible that Tommy broke his hand." Mary said. "He was really looking forward to this."
"I know. I was really looking forward to having him here. So, you and Tommy stay in close touch don't you, Mary?" Nathan said, his eyes now drawn to Mary's wedding ring.
"Oh, you know exactly what it's like to be a friend of Tommy's, don't you Nathan." Mary responded to Nathan's forward question by dodging and bonding with him over Tommy. Mary knew Tommy was beloved by his regulars. "It's a lifelong commitment, isn't it!"
"Ha-Ha. yes, it is Mary. It really is too bad for him that he broke his hand like that. But Zach seems like he'll be a solid back up for our good friend, Tommy."
"He's here?" Mary asked. "Point me in his direction. I know you are still getting ready, Nathan."
"Of course."
Nathan walked Mary through the foyer into his spacious living room, with the bar set up on the far end, near the kitchen. He pointed toward the bar and Zach, who was busy preparing for the arrival of guests.
"I will be back downstairs shortly after six pm." Nathan said. "A young woman from the cigar store, Brandi, should be here just before six. She'll be serving my guests their choice of the finest Dominican and Latin American cigars from a portable humidor she will wheel around throughout the party."
"Classy!" Mary answered. "I'll be sure to let her in!
"You go upstairs Nathan and take your time getting ready. I will handle everything down here and get your party kicked off with a bang!"
"Ha. A bang, Mary?" An excited Nathan asked.
"Oops." Mary retorted, giving Nathan a flirty wink and a smile. "Just a figure of speech, you bear!"
Mary nervously walked toward Zach, still not sure what she wanted to say to him. She knew that first she needed to ensure they were on the same page as far as the night's business was concerned. She found that Zach had the bar well prepared and greeted her in a friendly, if business-like, manner. She greeted Zach similarly. With staff from the caterer busy setting up the hors d'oeuvres, and the carving table, there was no opportunity to address her uneasiness about their encounter two days earlier.
Soon, Brandi from the cigar store and her portable humidor arrived. Brandi, age 25, was an inch shorter than Mary at 5'3" and had shoulder length blond hair. Like Mary, she wore a black cocktail dress, but with a scoop neck that displayed her ample breasts. On her small feet she wore matching six-inch heels. Once settled in the middle of the living room, she bent over the humidor to display her fine cigars, catching the immediate attention of the early arrivers among the 18 male guests who had confirmed their attendance.
Mary greeted and chatted up each man who arrived and moved them on to the bar for their initial drinks. Though she had not worked in a role like this in many years, Mary felt it came to her naturally. Her self-confidence helped her overcome her initial anxiousness. She was ready to make the most of her opportunity, in serving drinks to these rich men.
Roger, a distinguished broad-shouldered man, age 70, gray haired, in a tailored suit, held court with a small group of guests. He was giving his views on the stock market when Mary came over.
"Mary, I put down my dirty martini, and don't remember where I left it. That bartender made my first one perfectly. Can you bring me another one?" He asked.
"Absolutely, Roger."
When she was returning with his drink, Roger had finished his conversation and gave Mary his full attention, eyeing her head to toe as she walked toward him carrying a tray with his drink atop.
"You are a stunning woman, Mary. I hope you don't mind me telling you that. But I don't mince words!"
"Oh, thank you Roger. That is nice of you to say." Mary said, smiling widely as she handed him his drink.
"We've never met," She continued, "but I remember watching TV a few years ago and I saw you on the news, giving a speech to City Council. You were so passionate, Roger. You said it was your lifelong dream to build the tallest skyscraper in Philadelphia. With a thundering voice, you said your project would be privately financed, and provide free childcare on the ground floor to the children of working people. Thousands of good paying, family sustaining jobs would be created. All you needed from Council was a tiny little zoning variance and tax credits."
"You have a strong recollection of the facts, Mary."
"Who could forget that speech Roger! The people responded! They rose up, embraced your dream, and soon Council passed the ordinance you needed. Our community depends upon imaginative entrepreneurs like you who create jobs and bring vitality to our region, while at the same time addressing pressing needs. I find that so admirable!"
Roger laughed. "I wish City Council were as appreciative of my good deeds as you seem to be, my pretty lady."
"Don't listen to the critics, Roger." Mary assured.
She then got up on her tippy toes, leaned into Roger, bringing her right hand up under his left arm, to his shoulder, pulling him closer. She rested her left hand on his chest over the lapel of his suit jacket, while bending her left knee forward and slightly inward so that it touched the inside of Roger's left knee. Mary whispered into his left ear.
"You are the one who had the vision and the power to erect your dream in the heart of the City. Your dream became a reality Roger. As anyone can plainly see, your erected edifice towers above the erection of any other man in the history of this town!"
Roger let out a loud laugh. Mary gave him a wink as she pulled away from him and moved on to chat with another guest.
Over the course of the next few hours, Mary owned the party. She chatted up flirty men, never letting things get out of hand. Whenever Nathan was in earshot, Mary was telling at least one of his guests a made-up story about Nathan being some kind of ladies' man back in the day, always surrounded by a cadre of pretty, young women.
Securing timely refills from a ruthlessly efficient Zach, she had the guests feeling good and tipping generously. At one point, Mary and Zach even congratulated each other on their impending haul.
At various times, Mary would glance over at Zach, and see Brandi talking to him, twirling her hair with her finger. From what Mary observed, Zach was not paying much attention to her.
Just after 8:00 pm, Mary spotted Roger and Nathan having what looked like a serious conversation. Nathan seemed to be trying to convince Roger of something. Mary asked Zach to prepare fresh drinks for them.