When she started working at the firm, she had worked in his division. Larry was a VP, she was in the occasional meeting with him. Never even spoke to him one on one. But her impression? He was an arrogant ass. Cocky. Obnoxious. Opinionated. Her coworkers mostly felt the same way.
A couple years later, she moved up into management, she heard different opinions about him and what kind of guy he was. Her best friend had known the guy for years.
"He is really a nice guy. But he is type A and always focused on the goal. He takes care of people, but he doesn't suffer fools well. He isn't afraid to make a decision or give his opinion. Sometimes, that comes across as unfeeling."
Eventually, she was assigned to some cross division projects and she had the opportunity to meet him in business situations. He was definitely opinionated and very confidant. But she found herself agreeing with those opinions.
Working for the firm meant lots of traveling. There were lots of dinners and sitting around in the bar at night. During these times, she began to see what he was really like. He loved to tell funny stories. He was the least politically correct person she had ever met. He had a wicked sense of humor and she discovered that he would make himself the butt of the joke more often than not. It only took a few of these encounters for her opinion to change.
She knew he was married, his wife had been at a few social functions. But he loved to flirt. He was hitting on every women in the bar from the youngest to the oldest. It was more of a compliment to them, making all those women feel special and noticed. But she never thought he was serious about it for a second.
One warm summer night in a bar somewhere in the Midwest, she remembered thinking "I was totally wrong about him. I like this guy. My old coworkers would be surprised."
She also noticed that he really paid attention to the performers. It didn't matter that they were younger or more experienced. He engaged them and asked questions and listened to their opinions. They could change his mind. He gave them credit in front of others and arranged from the junior people to work on higher visibility programs. It wasn't just a women, he supported a lot of the men too.
It was no surprise when these people started getting recognition within the firm and that included her. The annual corporate award conference - the President's club - was held at a very posh resort in Northern New York.
When she arrived to sign in to the sold out hotel, she got horrible news, her room had been cancelled. Her admin assistant was supposed to change it from a Thursday arrival to a Friday arrival; instead the resort had cancelled it completely. She was crushed and panicking. The nearest hotel, was a dumpy 1950's motel ten miles from the resort. She needed to be here to meet people, network, not be down the road in some dump. She was so upset she could cry.
Her face was flushed and her mind was racing, when he stepped up to the desk.
"Pardon me. I overheard your problem. If it is ok with you, you are welcome to the other bedroom in my suite. VPs get a two bedroom suite, with an adjoining living room. I only need one room. If your husband wouldn't object, you are both welcome to the other room."
Her husband hadn't accompanied her to the event. It was a sore subject. Very sore. She was still angry with him. Her 'cute award' wasn't worth him taking off the extra two days from work. She took her anger to Saks. She would make sure he regretted missing this event. She had gone out and spent even more money buying a dress that looked great on her. She wasn't a small girl, she had boobs and a butt and the curves in between them. The woman at Saks had helped her find a dress that made those curves look incredible. Long black and formal. But a long slit up the side and sheer enough at the top to draw your eyes to her cleavage. It came together in a high waist that made her feel so damn sexy.
"My husband won't be here this weekend and I wouldn't want to intrude on you and your wife."
He looked at her, and then turned the desk clerk. "That settles it. Please have the bellman take her bags up to my suite. This lovely lady is going to take me to that bar over yonder and buy me a drink in trade."
She just nodded in agreement and followed him to the bar. That was the thing about him. You just did what he said. He wouldn't let her buy the drink either. He was an cad and an old fashioned gentleman at the same time. Always a contradiction.
As they sat in the bar, he explained that his wife was on a board and they were meeting this weekend, so he was a bachelor too. For a moment, she consider texting her husband and asking if it was OK. No, screw him. He had a chance to be here. If it's not important enough for him to be here, she wasn't going to ask his permission. After they finished their second round of drinks, the bellman walked over to them and handed them their room keys.
"You're bags are taken care of sir." He tipped the Bellman generously and they headed up to their suite.
When they go to the suite, she was very impressed. Two bedrooms and a living he had said. It was bigger than her first house. The 'living room' was huge, a large screen tv, a full bar (with booze), sectional couch and dining room with a table filled half of it.
They each walked towards separate rooms, not sure who's luggage was in which. She opened the door to what she thought of as her room. A king size bed, private bath with a shower and a whirpool tub. A makeup table even her own small couch and chairs. She opened the closet and found it empty.
Then there was a knock at the door. "I think the Bellman misunderstood our relationship. It appears that your clothes have joined mine over here."
She laughed. Then followed him over to his room.
If her room was large, this one was huge. A giant bed. There was a step that went across the room, two steps down, there was another large sectional looking across a set of windows and French door that opened out on to the balcony and the golf course beyond.
He took the hangars with her suits and dresses and took them over to her room. She emptied the drawer into her suitcase. After another trip, her stuff was all in her drawers in her room. They agreed to freshen up and then head to the reception in about 30 minutes.
Thirty minutes later, she had touched up her makeup and pulled her long red hair into her 'corporate look' bun. He knocked at the door quietly.
"I think we missed one drawer. These were in the drawer next to my bed." He handed her a small pile of her panties and bras. She blushed. How embarrassing.
These were her sexiest undies, she had packed them hoping her husband would change his mind and still come on the trip. She turned back towards her room and then she noticed the weight. Oh fuck. She knew it was there, without even looking. The shape was easy to recognize in between the layers of lace. Her butterfly vibrator. Damn it! Why had they unpacked her luggage? It was in an inside zippered pocket! Any other hotel she ever stayed at had just dropped the bags on the bed. Shit. He knew it was there. Clearly he had been nice enough to hide it in the middle of her intimates, without drawing any attention to it. He was probably just as embarrassed to find it. Her freckled skin was flushed from embarrassment. She could just crawl into bed now and die. After a few minutes, she walked out to the main room and met him to go downstairs.
She had known him for years. But as they stood waiting, she really stopped to look at him closely for the first time. He was older than her, by at least twenty five years. Salt and pepper hair, kept very short. Tall and in decent good shape. Clean shave. He had mesmerizing deep brown eyes. Yes mesmerizing was the word. When he was speaking to you, it was like he was looking right into your soul. It was those eyes that she had noticed long ago when she changed her mind about him. They had a little twinkle when he laughed. Oh and the dimples. He had dimples that were there when he smiled.
The door opened and they got on the elevator with some others from the firm. She turned to talk to a manager she had shared many late nights working with. They started talking and walked out of the elevator together. He turned right and that was the last time she saw him that night.
The next morning she heard him leave early, then return about an hour later. That was followed by the shower running. She got up and took her own shower. Today was golfing and local tours. Two of her friends were also here and they had decided to try the wine tour. Upstate New York had some great little wineries and they would be visiting a few of them.
When she walked out of the room, he was sitting at the table eating a room service breakfast. He asked if the room was OK, then they discussed the awards dinner that evening. She would be back by 4:00 to have time to do her hair and get dressed. Dinner started at 6:00.
It was simply a beautiful day; the bus driver took them to all the nice wineries. They drank a lot of sample, had some cheese and crackers along the way. By the time she was back to the room, she had an excellent buzz going on.
She went into her room and began getting dressed. First she took a long hot shower. She shaved her legs and her pussy. Her husband liked it when she left a little strip up the middle, but she decided that she liked the smooth look tonight. After her shower, she dried off and covered herself with her favorite Bath and Bodyworks lotion. Then she put her hair up. She had long naturally red and curly hair. It was a pain sometimes, but she loved it. She braided the front and left it down in the back.
The room had a full size mirror. Before she got dressed, she took a look at herself. She was in pretty good shape. The running and working out had helped her stay in shape. She had all the typical redhead features, blue eyes, freckles everywhere the sun touched, and a few places it rarely touched. Her skin was pale, until it burned. Then it got red, then pale about a week later. Her butt wasn't too bad. The squats and running were still paying off. Her boobs were here best asset. The girls were big round and still staying up pretty good. She had been measured for custom bras a couple years ago, 42 E, complete with the sensitive pink nipples. The wine buzz was still there and gently stroked her nipples. Damn that felt so good. She stopped because she knew she wouldn't be able to get dressed in time, if she kept going.
She took the dress from the plastic bag and laid it on the bed. She went to the drawer, pulled out her favorite black lacy thong and slid it on. For a brief second, she had considered going commando. But she thought better of it. There would be no bra under this dress that was sexy enough - going without panties, would drive her insane with lust. She pulled the dress on. It was snug, right up into her lady bits. The black shoes were stilettos with an open toe. So she wouldn't be wearing hose tonight.
Then the dress. She was feeling so confident and sexy. This dress was amazing. She pulled it over her head slid it down. She moved her boobs into place inside the satin lining. She reached behind to zip the dress up. Oh shit.
She couldn't reach the back and zip it up. She was going to need some help. She texted her friend, Jen. No response. She called her, nothing. It was already late and dinner would be start shortly. So she took a deep breath and walked out to the common room.
"I have a problem. Could you help?"
