Angela was a successful administrative assistant for a large firm. She had married Ben and had children who were now on their way to college. She and Ben had done well for themselves they had a nice house in an upscale neighborhood. Weekends in the summer were generally filled with BBQ, golf and relaxing in the hot tub at their house. Ben and Angela still had an active sex life that had gotten more adventuresome since the kids had left home. Life was good but had lost some excitement, Angela felt the urge to do something daring and exciting but didn’t want to upset the nice life her and Ben had made for themselves.
Angela was at work Monday morning everything was going the way a typical Monday morning goes until her boss Jack popped into her office. Jack was a little older with just a touch of grey starting in his dark hair. He was tall with broad shoulders and worked out at the office gym most nights before going home. Angela found him attractive but intimidating so she never allowed her thoughts to be anything but professional with him. Jack seemed even more intense this morning standing in her office. Angela couldn’t help but notice Jack’s eyes fixed on her she immediately felt a little self conscious about the low cut top she had worn this morning. She could almost feel the heat in her chest from his eyes fixed on her 36 CC breasts. Jack’s eyes moved up to make eye contact with her. He said that one of his clients had contacted him this weekend and needed his assistance right away in Florida. Angela knew how demanding some clients could be so she was not all that shocked that he had to fly down to help the client. What did shock her was Jack needed her to go with him to help with paperwork. Jack told her he had already got tickets and the flight would leave at 1pm and that she needed to go home right away and pack for the trip and meet him back at the office at noon. Angela asked how long she should pack for she was hoping just a quick overnight trip. Jack said “I don’t know maybe a day or two maybe a week” and left her office.
Angela texted Ben about the trip, she rarely went away for work just maybe once or twice before in her 15 years with the company. Ben was surprised and asked when she would be back. She gave the same reply that Jack had given her.
Angela rushed home to pack some clothes she knew it would be hot in Florida and was not quite sure how professional or casual she should pack. Also not knowing how many days to pack for made it more difficult. She thought to herself – sure it would be easy if I was a man. She felt herself get frustrated with Jack for dropping this on her on such short notice. She grabbed mainly skirts and varying tops to go with them thinking they would be cooler than pant suits that she typically wore to work. She gathered up her bras and panties most of which were somewhat sexy because that is what Ben liked to see her in. She wore a thong most every day so those she could take plenty of with out taking up any space. She rushed to her closet to grab a couple pairs of shoes, a pair of black high heels, a pair of comfortable flats, a pair of sneakers and a pair of sandals. She grabbed a light sweater out of the closet just in case and when she did a bikini that she had never worn fell out on the closet floor. She had bought it and then after getting home with it decided she was to old to wear something like that even though Ben told her how good she looked in it when she tried it on at home for him. The thought of wearing it did get her excited she was craving some excitement lately so she stuffed it in to her suitcase. Maybe she could wear it at the pool or beach since she wouldn’t know anyone in Florida anyways. She closed up her luggage drug it downstairs to the garage and tossed it in the car and headed back to the office.
When she got back to the office Jack was waiting in the parking lot and told her to put her bags in his car and ride with him to the airport. She put her bags in and sat down in the passenger seat of Jack’s car. He looked over at her with a half smile as he put his car in drive. With his dark sunglasses she could not tell but she was certain Jack was eyeing her cleavage again. For some odd reason this time it did not make her feel self conscious maybe it was because she wasn’t in her work place. She felt a little excitement and started looking forward to the trip.
Jack made some small talk on the way to the airport but mainly just filled her in on the client’s troubles. They arrived at the airport parked the car and jumped on a shuttle bus to the terminal. Jack was very nice and carried her suitcase for her while she carried the smaller carry on bag and her purse. They didn’t have to wait long before boarding the plane. Angela took the window seat and Jack the middle seat on the plane. The plane took off Jack took out his laptop and began working on some documents. Angela felt like she should be working since this was a work trip, she asked if Jack needed her help with anything, he said No just relax I am just taking another look at these so the are fresh in my mind. Angela laid the seat back and relaxed and before she knew it the plane was getting ready to land. She must of dozed off to sleep the fight went way to fast. She looked over at Jack who was still working on his laptop she looked down and noticed that her lace bra was showing in the low cut shirt she had on she must have moved around enough during her sleep to pull her shirt down and open more. There was no way Jack didn’t notice if he looked her way at all in the last couple hours. She straightened her top and put her seat back up. Jack asked her “how your nap” with a smirk on his face, Angela knew he had noticed her lacy bra. She replied “it was a good nap I didn’t know I was that tired”. The chatted briefly about the client then Jack closed his laptop they buckled their seat belts and the plane touched down in Florida.
Jack and Angela grabbed their bags and walked to the exit of the airport to a car their client had sent to pick them up. The air was hot and humid Angela was glad she had packed cooler clothes for the trip. The car took them to the client’s office which was a large building with large glass windows floor to ceiling. The driver told them to leave their bags in the car and he would take them to the hotel.
John the client of Jack’s met them at the entry shaking Angela’s hand then shaking Jack’s as they moved to the elevators. A quick ride to the 10th floor in the elevator they walked into a large conference room with 8 people already sitting at the table with file boxes and laptops working away. Angela stopped near the door and John and Jack continued through the room to an office in the back of the conference room. Angela felt a little uncomfortable not knowing really what to do since Jack had not given her any instructions yet. She found a chair near where she was standing and sat down waiting for Jack to come out of the office and give her some instructions. She pulled out her phone and text Ben to let him know that they had made it to Florida and the client’s office. Ben told her he missed her already and was horny at the thought of her traveling with her boss. Angela dismissed him as being a pervert she told him she would text him later when she got settled in to her hotel room. Ben suggested she send him pictures of the room and some of her self since she left him home all alone with a sad face emoji.
Jack came out of the small office he was in with John and walked up to where Angela was sitting and told her that he would be staying late to work with John but she should go back to the hotel since John had put together this group of people to handle the paper work part of the project he would call her later tonight or in the morning to let her know what the plan for the following day would be. He gave her a pat on the shoulder and said there would be a car down stairs waiting for her to take her to the hotel.
Angela went down to the car and asked the driver to take her to the hotel. She sat in the back seat of the car wondering why Jack had asked her to come along if John already had plenty of people to work on this project. The ride to the hotel was only a couple blocks the driver pulled up and opened the door for her. He handed her a room key and said room 410 it has a great view of the beach and overlooks the hotel pool. Angela took the key and headed up to her room. When she got there she opened the door to a large room with a couch, chair and huge TV on the wall marble looking flooring with large windows. The driver was right she had a great view of the beach and ocean. To the left was door leading to the bedroom it also had a large widow overlooking the pool and a king sized bed with a large TV on the wall. He bags were sitting on the bed. It wasn’t to late yet and she was hungry in the rush to leave she didn’t get a chance to eat lunch. She decided to order room service and change into something comfy for the evening and just relax. She looked at the menu and picked up the phone to order some food.
While waiting for food she changed in to some running shorts and a t shirt she brought for sleeping in. She decided to ditch the bra for the day and maybe give the room service waiter a little peak at her hard nipples poking out of the thing T-shirt. Young waiter brought her food on a cart and she instructed him to just place it on the coffee table in the living room area. He sat the dishes on the table and turned to face Angela he struggled to look her in the eye with most of his attention on her chest. Angela smiled and knew he noticed what she had hoped he would. After a moment of silence he finally stuttered out “Is there anything else I can get for you” Angela said “no and thank you” and gave the young man a smile and a tip.