One Night Stand in the Windy City

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She was pretty much all alone in this city. No coworkers, no husband and no other acquaintance within the big city of Chicago. Her clients had been hospitable, but were suburban dwellers who took her out for a nice early dinner, and now were now on the train out to Naperville.

Sherry felt a freedom she hadn’t had in a long, long time. The freedom to not know anyone and be able to do anything she wanted without fear of being discovered. It felt like it was too good of an opportunity to pass up.

Sherry loved her husband, but they had been together a lot of years. Decades in fact. They had been pretty wild as a young married couple and did some things that most couples never did, but they had been monogamous since the first kid was born. There was just too much to lose at that point and too much responsibility.

But not tonight. Tonight was all hers. She needed a spark.

Nothing too risky and certainly nothing that would last more than an evening. Fun, flirtation. The idea of a random fuck was probably a fantasy she would never ever go through with, but the idea was there in her mind.

It was a Wednesday night in Chicago. Not the most active of nights but beggars cannot be choosers. It wasn’t even 8PM yet and she had the night to herself and a really beautiful hotel room downtown.

Although she had no plans to change clothes she popped up to the room after dinner. Her night had been all about Italian food and the garlic was on her breath big time. A brush of the teeth and a gargle for luck and she was ready to go.

She took a moment and asked herself “Am I really going to do this?” She surveyed herself in the mirror. Definitely not young anymore, but still had a good figure. Her clothing was business attire — all she had with her — but it was stylish, sophisticated and complimentary of her ample charms.

Although she would be walking in the city, she did lose her sensible flats that she had brought for walking for a less conservative set of heels. Before sliding them on she decided to lose the pantyhose and slid on a set of silk pants under her skirt.

That last change made all the difference. The simple gray pinstripe skirt and light blue blouse still made her look like she had just gotten off work at a local brokers or perhaps she looked like real estate agent or something. Under that all she felt like a sexy woman and that was what tonight was all about. Emerald colored underwear with a lace front and matching bra from Victoria’s. If things heated up it would certainly do.

It was April and although no longer winter the weather was chilly. There was cold wind coming off the lake. She left the formal jacket on the hanger in the closet but grabbed the long black overcoat she loved the cut of so much. And then she was on her way.

The bar not far from the hotel was promising. She had been there years back at a soiree held by a hand held electronics company she used to work for. On entering, it didn’t seem like it had changed much – all dark wood, green felt and polished brass. It had the feel of Chicago — at least to her.

She felt she recognized the barman and struck up a conversation, asking him if he had been there a while as she seemed to remember his special talents with her favorite drink. She found out it was just the case, and you could almost see the old man grown and inch or two with pride that he’d been remembered. It made her feel at home to know he was a fixture here.

The pour was deep and strong, and the barman’s attention was prompt and professional, but warm and done with pride.

She had remembered a small dance floor, but sadly the she was told the place had changed a bit after all. She was told that this part of the bar was now a banquet room. Even if it hadn’t been, Wednesday night would not have been big for dancing.

The idea of close dancing with a stranger had been high on her list of things to do, but easily enough she left it behind. You don’t always get what you want. She just hoped she would get what she needed.

Drinking with her new old friend behind the bar was oddly comforting. There was that lovely little tingle one gets when good liquor hits the back of your head. She finished, and he made her a second. He left her alone with her thoughts and fantasies.

There were men aplenty in the bar — just a few women sprinkled here and there. No identifiable couples bahis siteleri and only a few single men, none so attractive that they garnered her attention. This was an after the office drink crowd, and there didn’t seem like there would be an opportunity to split a single man from the herds.

By 10, she was through her third drink and out of small talk with the bartender. The buzz was comforting but the evening seemed a bust. She paid her tab with a generous tip and stumbled out into the night.

She was lost in minutes. It was downtown and not scary, but she was not in the mood to find her way alone. She dropped off into the lobby of a small hotel seeking directions. She saw that the front desk staff were busy checking in a van full of airline people into the hotel for their overnight layovers.Getting their attention would take a while and no concierge or bellman was in sight.

The bar accompanying the hotel seemed to be active so she thought she’d give it a try. The staff there could help.

On entering, she found it to be one of those busy hotel bars filled with men who travel for a living. It’s easy for a woman to be the center of attention in a place like that, and she could feel all eyes on her as soon as she entered. This was not always a welcome feeling, but tonight it was welcome and even revitalizing. Rather than ask the bartender for a directions, she decided to stay for a drink.

The group of well-dressed businessmen who were huddled beside her at the bar instantly included her in their conversation. The barman gave her the once over, deciding she was not an escort looking for business and took her drink order. It went onto the tab of a new friend who introduced himself as Ken.

Ken was obviously the alpha male of the trio of men who she shared a bar stool line with. They were there to visit a retail chain about their sportswear line, and though she might have taken a moment to tell them that her husband was also in the apparel business, she held her tongue so as not to kill the mood.

The conversation continued and the drinks were consumed. The men were attentive and polite, though after a short while it was obvious that her blouse and its contents were the center of attention.

A quick scan counted three wedding rings including her own, the odd man out being 30-something Ken. He wasn’t bad looking, tall and well built with his blue jacket and tan shirt with the amusing necktie design of very small polar bears walking nose to tail. If looks alone could make Sherry happy, this might have been a match.

Ben did most of the talking, while the two other men mostly sat and drank and stole quick glances as their new female compatriot. The other two men were Randy and Larry. Both were younger, quieter and less confident than the boisterous leader of their group, but they still made polite conversation and opened up a bit as the drinks flowed.

The more Ken talked, the less interesting she found the man. She was quite thankful when he excused himself to go the men’s room. She had heard all about his golf game, the condo association at his place in El Segundo and about more Ken in general than she had really cared to hear, and said something to that effect once he was out of earshot.

Both of the other men laughed knowledgeably and in appreciation for her being able say what they hadn’t dared. Randy apologized and explained Ken had been drinking for several hours. Larry just blushed and giggled,telling her perhaps he was in the tank too.

They shared a few more barbs targeted at boss man Ken including a few about the fact that his absence indicated he was either lost or would be coming back to the bar several pounds lighter — possibly his head would be caved in if that was the case. It was a crudity that had us all laughing. Larry got a phone call and stepped away, and Randy and Sherry sat and discussed small nothings, each saying just enough to keep the conversation going.

He told me a bit about how he got into sportswear (He majored in “college jock with a minor in communications.”) He told her he had a boat, which she loved as boats are one of my favorite things in life. He had plans and goals and a boat payment to make and lots to learn from his mentors. His was a life at the starting line in many ways and she found that attractive.

Randy and his team were staying in the hotel attached to the canlı bahis siteleri bar and asked if she was as well. He was amused when she told them she was only there because she was lost. She said it looked like a nice place to spend the night — a small attempt at flirtation. He didn’t get it.

Instead he asked what the name of her hotel was as he might know the way, and laughed when she told him as the hotel was just around the corner. Before she could say anything, Ken returned with Larry in tow.

Ken was looking like a man who had spent a serious amount of time in front of a mirror. He was boisterous about the need to buy us all another drink. The twinkle in his eye told her that she was in his sights, and frankly she could not have been less interested.

Explaining she had an early flight, she made her apologies, and tossed a $20 on the counter. Not enough to pay her tab, but a clear indication that she saw no obligation to Ken.

Then, in a move she would never understand later, she locked arms with Randy and announced how pleased she was that he had offered to walk her back to her hotel.

Four sets of eyebrows instantly raised – her own included. (Sometimes she just didn’t know how it was that things come out of her mouth like this.) Before anyone could say more and before Ken could grab his AMEX and attempt to settle the tab, Sherry had dragged Randy by the arm out of the bar and they were practically running as they left the hotel lobby.

They didn’t stop until they were in the lobby of her own hotel. She turned, apologizing for kidnapping him, but explained the he appeared to need an escape from Larry and Ken as much as she. He especially laughed at her use of the word “windbag.”

She kept his arm locked with hers as she moved through the lobby. She asked him if he wanted a nightcap, and he noted that the sad little bar in this hotel was closed. It did not matter. Shortly, Sherry and Randy boarded the elevator together.

Her room was on the 34rd floor with a good view of the river though sadly no balcony. It was just a bedroom but had two nice armchairs that were easily turned toward the floor to ceiling window view, and a small side table to hold the small bottles of rum and orange juice she had taken from the mini-bar.

Randy volunteered that he was married. It was an odd stumbling statement offered in a tone that suggested a question mark at the end.

“Me too” was her reply. She asked if he needed to leave and he said he should, but he made no attempt to. In the silence that followed much was said.

She had taken off her overcoat upon entering the room. She got up and picked it off of the bed, taking a moment to hang it in the closet.

He was watching her, and she got a good look at him in the small light of the bedside lamp. Perhaps as much as 10 years younger than she. Good looking in his way, but his face showed concern and uncertainty about what was to come next.

She had done the extra marital dance before. He clearly had not.

She was not often the aggressor but seeing the late time felt like perhaps it might be best. After removing her heels and putting them on the high shelf in the closet, she unbuttoned the cuffs of her blouse, and then the blouse itself.

He did not say a word – didn’t even change expressions — and didn’t move while she finished with her blouse and placed it on a hanger.

Their eyes were still locked as she began to unzip her skirt. She started talking, giving him an improvised set of rules.

This wasn’t going to be cheating – not all the way anyway. She couldn’t live with that. But it would be a lot of fun if he let it be. At the end she would feel like a woman instead of just a mom, and he would feel like a new man. Wasn’t that enough?

There would be no sex — not complete sex — but they could explore and enjoy mutual discovery. It would be like in the backs of cars or under the high school bleachers so many years ago.

There would be kissing and some groping certainly, maybe something more, but definitely not THAT. High school stuff really. Something that would make them feel young again.

She had dropped the skirt as she ended her monologue. Standing in her panties and bra emboldened her. She unhooked the bra and let it fall to the floor.

“Now dear,” she asked, “It’s very late. Do you want to do this or do you want to canlı bahis leave? It really is decision time. I do hope you will.”

He stood. He walked toward her and the door, pushing past here to that little hallway hotel rooms are known for – closet on one side, bathroom door on the other and exit to the hall straight ahead. Once again she felt her evening slipping away and she felt herself die a bit in side. She had needed this.

He was past her when he stopped, reached into the closet, and pulled out the heels she had been wearing. He showed them to her, and with a smirk he whispered, “If this is for fun, would you put these back on?”

How could she refuse?

When the shoes were in place and the straps behind her heels, he was on her. Lips on lips, body on body. Her nearly naked and he fully clothed. They kissed passionately for minutes, his hands on her breasts, their almost innocent act of ‘making out’ bringing back memories of earlier and more innocent times.

He moved his mouth to her breasts and suckled her nipples, then buried his face in her breasts. . His hands reached down to cup the cheeks of her ass as he pulled her to him almost violently. After a while, it was all she could to keep her panties from slipping to the floor. His hands busy exploring inside them. Her willpower slipping away. He moved to take them off as she sought to preserve that thin blue line of cloth. It was an old fashioned tug-of-war that was the right of passage in a simpler time when the difference between third base and home really meant something.

Still after all this time he hadn’t completely undressed, but his shirt was unbuttoned and his pants opened wide. He had grown large and hard, but there were still room enough in his boxers for her hand to move inside.

Finally the underwear slipped down below his manhood and she took control of him with her fist. He found the route to his prize by pushing aside the panel of cloth between her legs and buried his fingers in her warmth.

He was on her fully and could have easily taken her. She was ready he knew even as she sought to keep the panties up. Finally he slipped down and moved his mouth to her sex, first through the slippery cloth and then with it pulled aside. Finally, after a while, the panties were down. He pulled her legs wide apart in way that opened her most deeply. He was hungry for here, but attentive and giving.

He almost drowned when the time (and she)came. She cried for a moment in both fulfillment. The rooms next door surely had heard her, and she surely did not care.

He wanted — actually they both wanted – him to slide inside her then, but he realized and respected that her wishes. Breaking the rules now would change the nature of their act. Make it somehow unclean.

After a while, she pulled him on top of her, then rolled over and slid down so that she could wrap him with her large breasts. She had always enjoyed the nastiness of a good tit fucking – the feel of his need and the sticky reward. Realizing that she was not slick enough there despite his time between them, she briefly put him in her mouth — a wet and sloppy act — and then again slid him back between her breasts.

He did not last long. How could he? His cum was thick and very warm and very rewarding, and though he fell to his side as men are bound to do he quickly recovered. They spent the next minutes cuddling and kissing and during that time the fluids he’d released on her body wound up on his shirt, his skin and on the hotel bed linens.

It was perhaps 4:30 in the morning when Sherry rose from the bed to visit the bathroom, and on return stood naked in the window looking at the pre-dawn view. A beautiful sight indeed. He stirred when she left the bed, and feeling it was time to go gathered his things. He put them on though they were rumpled and wet. \

There was a brief attempt at the kind of awkward small talk that always comes as such times. Even the beginnings of a “can I call you” conversation which quickly fell apart as it was as dishonest as such conversations always tend to be. This was surely a one night stand. No need to soil it with lies.

She kissed him at the door, not caring that her nudity might be seen if anyone was in the hallway. (There wasn’t.) She stood and watched as he summoned the elevator and then disappeared forever from her life.

After a brief date with a wash towel and soap was off to bed. This time for sleep. In the morning it would be back to business. It had been an evening with no future and no expectations, but one she would remember and cherish for the rest of her life.

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