Chris was sitting in the hotel bar. He was in Chicago because his boss had sent him to meet with a client and as his boss put it, 'unfuck the situation'. Apparently a salesperson had over promised what the company could deliver in the time needed to actually build out the custom software they had purchased. So Chris had to board a plane, take an Uber, and basically get berated for two hours by the client while trying to salvage the deal.
After making promises to add additional features for no cost shortly after the main product was released, Chris had calmed the client and his company was allowed the additional 3 weeks it would take to complete the original product. He grabbed his bags from the lobby and caught another Uber to his hotel.
He phoned his boss as he was settling into his room and told her about the deal that was made. She wasn't happy that Chris had to agree to give up so much, but also knew giving up $20000 in free upgrades to save the half a million dollar project was worth it. "What time do you fly out?" she asked him. "Earliest flight I could get was at 10 tomorrow morning out of O'hare," Chris replied as he was setting his toiletries next to the bathroom sink. "Ok. As soon as you're on the ground, call me. I am going to get the head of sales in my office with you and set that sonofabitch straight. We can't keep bailing his people out when they fuck up like this. This is coming out of somebody's commission!" The call ended and Chris decided he needed a drink.
So here he was sipping his second whiskey and just thinking about how it looked like the rest of his week was going to be arguing with the sales team. Suddenly a woman's voice caught his attention. "Is this seat taken?" Chris had been lost in his thoughts and turned to see a woman in business attire standing next to the empty barstool to his right.
Chris saw the woman's bright eyes and welcoming smile. She looked to be in her late 30s or early 40s. She had shoulder length brunette hair and a slim build. "Uh, no. It's yours if you need it," he replied. Earlier he had noticed a group of people huddled up at the end of the bar who were also in business attire so he assumed she was going to take the chair and join them. He was surprised when she sat down next to him. "Thank you. I've been on my feet all day and could really use a break and a drink," she said as she settled into the tall chair.
Chris offered a knowing smile. She offered her right hand, "I'm Liz." Chris shook her hand and told her his name. The bartender asked Liz for her order and Chris smirked approvingly when he heard her order a whiskey neat. "What, women don't drink whiskey where you're from?" Liz chuckled as she saw Chris's reaction. Chris explained that typically when he sees women on business trips order a drink at the hotel bar it's usually a glass of wine or a mixed drink. Liz laughed at his comment, telling him that it sounded like he was stereotyping her.
Chris and Liz chatted while they sipped their drinks. Liz was in marketing for a pharmaceutical company and was in town meeting with a vendor that produces digital signage for her company. She had been working with them to develop a new marketing campaign for one of her company's products. Chris explained to her why he was in town. Liz excused herself to go to the ladies room and came back to see Chris still in his seat.
Soon their drinks were empty and Chris was reaching into his pocket to remove his credit card to pay his tab. He planned on heading up to his room to order room service, shower, and get some sleep before checking out in the morning when he got an idea. "If this is too forward, please let me know. I hate dining alone and was wondering if you would be interested in joining me for dinner. I wouldn't want to do anything that would offend you or get you in trouble with your husband," he said as he laid his credit card on the bar waiting for the bartender to come take it.
Liz smiled at him, "Well it is forward, but not too forward. I would love to. I agree dining alone sucks. And you don't have to worry about offending my husband, haven't had to worry about that for some time now." The comment was courteous with just a touch of flirtatious tone that Chris felt relieved that he wouldn't be looking like a complete ass for asking a complete stranger to dinner.
Once their bills were paid Chris and Liz moved to the hotel's restaurant and got a table. They chatted more about themselves as they ate. Liz let Chris know she had two children, one was just finishing their junior year of college and the other was married and had just moved to the Kansas City area to take a new job. "I know it is never OK to ask a woman's age, but I would never assume you were old enough to have children that old," Chris said. Liz blushed a little and replied, "Thank you. That is sweet, but I am probably older than you think. My son and his wife are expecting their first child in a couple of months which will make me a grandma."
Liz looked across the table expecting Chris to shut down hearing that the woman that had been flirting with him was in her early 50s and not as young as he thought. She knew she kept herself in shape and worked hard to maintain her appearance. She was actually surprised that the man she assumed was in his early 30s found her attractive enough to offer her dinner. While she saw surprise on his face, Chris didn't seem fazed by her response.
Liz decided to test the waters and see if this man was just looking for a dinner companion or if he was looking for more. "So Chris, you make it a habit of picking up old ladies in hotel bars, " She said with a chuckle. He picked up on the sarcastic comment and responded with a devilish grin, "Actually you would be the first woman I have ever picked up in a hotel bar, but if all women your age look like you, I might start exploring it more often."
Liz laughed and smiled at him across the table. "So where do you see this evening going after dinner is over?" She suddenly started to picture this younger man ravishing her body and was hoping he was feeling the same way. "Well, I don't fly out until 10, so it's not like I have a curfew tonight," Chris said. That devilish smile growing bigger across his face.
Chris got the bill and paid it. He asked Liz if she would like to join him for a drink in his room. Liz knew where this was going and just smiled, "I was hoping you would ask that." They left the restaurant and headed to the elevators in the lobby.
They stepped into the first elevator available and as soon as the doors started to shut, Chris turned to Liz. He leaned into her and pulled her body to his. They began kissing. It was not slow and passionate like some cheap romance novel. It was hungry and lustful. Liz broke the kiss and asked which floor he was on before hitting the button to activate the elevator.
Once the elevator began moving they were once again locked in a deep kiss. They nearly missed the elevator doors opening due to their focus being on one another. Once inside Chris's room they locked lips again. Chris began to kiss down Liz's neck when she broke away. "Let me set my purse and phone down," she panted.
She set her belongings down and turned some music on from her phone. With that done she stepped to Chris and began to run her hands over his chest towards his waist. She untucked his shirt from his pants, pulled it over his head and let it drop to the floor. She began to kiss along his collarbone and down his chest and stomach. As she kissed lower she sank to her knees in front of him. She smiled up as she started to unbuckle the belt in front of her eyes.
Chris was in awe. Just two hours ago he was sitting in a hotel bar trying to forget this day. Now this sexy assumingly older woman was on her knees in front of him in his hotel room. He reached down and gripped her head in his hands and looked down at her smiling face as she expertly removed his pants.
She pulled at his waistband and his pants and boxers fell to the floor. His 7" cock sprang free and bobbed just above her face. Chris watched as Liz's tongue darted out of her mouth and traced the underside of his shaft from his balls to the head. He shuddered at the warm tongue that was pleasuring him.
Liz was happy to see that Chris was sporting a decent sized tool. She wanted to taste it. She wrapped her lips around the head and slowly sucked her way down. Soon the head was perched at the entrance to her throat. She slid her mouth back upwards, pausing just as the tip came to rest between her lips. She inhaled deeply through her nose and plunged down, this time letting the head slide into her throat.
Chris moaned as Liz deepthroated his dick. This woman's mouth was amazing and she was giving him one of the best blowjobs he had ever had in his life. But he needed more; he wanted to bury his dick as deep inside of her as he could. He disengaged from her mouth and gently pulled her to her feet.
Liz let out a whimper as the delicious treat she was tasting was abruptly pulled from her mouth. She was pulled to her feet and spun around. Her hips were yanked backward and she could feel Chris's hands roaming over her blouse as he kissed the back of her neck. The buttons on her blouse were being released one by one.
Chris removed Liz's blouse and ran his hands all over the bare skin of her torso. Cupping her ample breasts through her lacy bra when he reached them. He felt around looking for the clasp. Once he located it in the front he undid it and let the sexy cups fall to the sides, exposing the C cup tits that had been encased in it. His hands went to them and he supported them in his palms as his fingers began to roll the pink hardened nipples that topped those exquisite globes between them.
