The following short story is a one-off fantasy featuring Jacqui, an almost retired businesswoman from England. It is purely fiction, but is based on real characters and places.
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Jacqui took another sip of her champagne. The film had just ended and she was into the last hour of the flight. The business class seating was comfortable in the extreme and life was good. At almost 65, retirement was on the horizon and she reflected that this would likely be her first and last business trip. There was a trade show taking place in New York and her boss had asked her to go to look at and comment on some document control software that had taken his eye. He was already there and would meet her at the show the following day.
The flight was due to land at around 6PM local time and Jacqui had plans to spend the evening sightseeing. She knew she should get some sleep to avoid horrendous jet lag, but this opportunity didn't come along every week. In fact, once in a lifetime, so she wasn't about to waste it in slumber, besides, she could sleep the entire homeward journey if she needed to. She decided to try and doze for a while before landing.
Jacqui was one of the lucky few who didn't look her age. In fact, she could pass for someone 15 years younger with the right lighting and had managed to maintain a slim figure. At 5' 5" she wasn't the tallest supermodel on the block, but her figure was nicely shaped and her 36C breasts enhanced that shape nicely.
She was just drifting into a dream when the familiar bong sound came over the aircraft speakers and it was time to belt up and prepare for landing. A flush of excitement washed over her as she contemplated the days ahead and the fact that tonight's sightseeing would be supervised by a friend who she had met a few years before on a web forum discussing retirement. They had never met in person, but had corresponded by email numerous times and got to know each other quite well. His name was Jack and he was few years older than Jacqui, but possessed an honesty and intensity which were tempered by shyness and which made him quite endearing. He had offered to give her the grand tour and she had readily accepted.
The usual delays and frustrations with immigration and baggage reclaim followed after landing, but she was soon out of the airport and enjoying her first Yellow Taxi ride to her hotel on the edge of Central Park. She was shown to her room by a uniformed "Bell Hop" and remembered to tip him. The room was spacious, much bigger than London hotels, and featured two of the biggest beds she had ever seen. A glance at her watch told her she needed to hurry as she was meeting Jack in the lobby at 8PM. She quickly showered and changed into a long black dress and matching black lace underwear. She sat on the bed and began to pull on a pair of black tights, but changed her mind and, on impulse, got a pair of black holdups out of her bag and put those on instead.
She stood up and took a look in the mirror, the overall impression was good. Not too much makeup, the dress fitted perfectly and showed just enough cleavage to maintain a man's interest. Jacqui and Jack were not internet lovers, so she had not come for a night of passion in a far off hotel room, but Jack had often complimented her on her appearance and she didn't want to disappoint him. She had put the holdup stockings on to feel good in herself. She had standards to maintain and had no desire to have him recoil when he finally got to see her in person. She also wanted to feel attractive. She took a last glance in the mirror before setting off to the lobby to await his arrival.
It was only 7:55PM when the lift doors opened, but she immediately saw Jack was there. She saw the look of recognition on his face and began to descend down the few steps from the elevator. Jack walked briskly over to the steps and embraced her with a hug and gave her a chaste peck on the cheek. After exchanging pleasantries, they set off out into the embrace of the "Big Apple". Conversation flowed as they took various means of transport to quickly take in the major sights. Jack insisted on recording the whole thing for posterity on a tiny camera he had brought with him. Jacqui wasn't sure about photos of her buying gifts in a department store, but nobody around, not even the shop assistants seemed to bat an eyelid, so she let him continue.
They ate in a diner which was something Jacqui had always wanted to do. Traditional New York fayre and so much she had to leave a substantial amount. Jack worried that she didn't like it, but she assured him it was just a question of portion size. She refused to let him photograph her eating, but he did get a couple of shots at the table and the waitress took one of the pair of them. Jack, with his arm around Jacqui's shoulders, both smiling and radiating joy.
By the time they got back to Central Park, they were loaded with bags. Jack expressed a doubt that she would be able to get all this stuff home, but Jacqui was confident she could make it fit in her oversized suitcase. That said, it was a bit inconvenient for their planned stroll around the park. Jacqui suggested that they drop the shopping off in her room and go back out again. The night was still young and there was plenty of time.
Having lived in the US for all of his life, Jack wasn't as impressed as Jacqui had been when he saw the room. It was perfectly acceptable, but nothing out of the ordinary to him. He smiled at the way she marvelled at the size of the beds, the huge window, the mini bar, bathroom and every other aspect of it. He sat on the bed and watched her as she moved around, pointing out features and generally happy to be in New York.
He retrieved the camera from his pocket and snapped a couple of photographs of her. Her smile was permanently fixed and was currently lighting up the room. She came over and sat on the bed opposite him. He asked her to pose for another photo and told her how he wanted her sitting.
Jacqui realised that the pose he was describing, which sitting on the bed, leaning back with both arms was extended behind her and her legs crossed would expose the elasticated part of her hold up stockings to him. It would also make her chest stick out to quite good effect. She felt naughty in teasing Jack this way, but then again, it was harmless fun and her husband wouldn't find out because the images were on Jack's camera, she was not so equipped.
Jack was delighted with the photos and held the camera up for her to see. She checked the hemline of her dress, which was not as revealing as she had feared. What she did notice though, was that the top of her bra cups were visible above the neckline of her dress.