This is a fantasy, none of the events here actually happened.
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I was back in New Jersey for a week of meetings with the other members of my team and we were out to dinner together, or more precisely, having drinks after our dinner. The members of my team are all close friends, though we are a pretty diverse group in terms of age, professional and social backgrounds, and it was common for us to go back to the hotel for drinks after we finished a business dinner together.
I am in my early 50's and I was talking with Gretchen, who is a very pretty, dark haired young woman who, I would guess, is around 30 years old. So technically, I am old enough to be her father, though I was thinking anything but fatherly thoughts as we talked and joked with the rest of the group.
It was late January and we were talking about New Year's resolutions. It turned out that most of us had made a resolution to get more exercise, and Gretchen was telling us about getting back into working out with weights. It seemed like everybody had a similar goal. I, myself added push ups and sit ups to my running routine, because it was something I could do while travelling for business.
Gretchen admitted that she was still sore from lifting and using muscles that she hadn't used for a long time. I did a quick appraisal of her taught, sexy body and tried to picture it without clothes. She was curvy, with a larger than average bust and a great ass, but a very thin waist. I honestly didn't see much room for improvement.
As the group was breaking up, Gretchen and I found ourselves with a moment of relative privacy, and I said to her that she needed a massage to help with the muscle soreness.
"That would be great," she admitted, "I had a massage on my last business trip when I stayed at that resort hotel in Fort Lauderdale and really enjoyed it."
"Well, you're in luck," I replied. "I just happen to be a very good masseuse. I would be more than happy to help you out, if you like."
Gretchen looked at me skeptically, and asked. "For real?"
I figured that she saw through my offer as a desperate attempt to get my hands on her body, but I decided to play it out anyway.
"Sure, let me show you." and I moved behind her and began working on her neck and shoulders with my hands. In truth, I was winging it.
As I peered at her face for clues on how I was doing she sighed, "Mmmmm, that feels good." and closed her eyes.
One of the other guys on the team who was watching us quipped, "Get a room, you two!" and everyone laughed. I was embarrassed and took my hands off Gretchen, as she giggled and blushed at the comment. Shortly after that, the group broke up and we all headed off to our own rooms, alone.
I had not stopped thinking about how nice Gretchen's graceful shoulders felt, or the fact that she seemed to enjoy what I was doing. I played it out in my imagination after I got to my room, and started to get an erection. I decided to go for broke, and picked up my phone.
I texted Gretchen, "That massage offer still stands."
After a few seconds my phone beeped, indicating that she was responding. The message appeared, "Your hands did feel nice :)"
I did a celebratory fist pump. She was still interested!
"How do I know I can trust you?" she added in the next message.
I replied, "Come on, we work together. You know I am an angel 0;-P"
"LOL. OK, but only for a few minutes. I am in 326"
Holy crap, I thought. She was actually giving me the green light. I put on track pants and a tee shirt and slipped into some flip flops. I took a Viagra that I had in my shaving kit and headed to her room. She opened the door and glanced around to see if anyone was watching us before letting me in. I wasn't sure what to make of that. The hotel we were in was set up with suites, each containing a sitting room in front and the bedroom in the back, separated by the bathroom.
She was still in her work clothes, and she looked at me and said, "How about if I sit at the desk and you give me a chair massage?"
She seemed nervous and a bit embarrassed, so I said sure. She had on a pale blue cotton blouse and gray skirt that ended at mid-thigh, along with black hose and a set of black pumps with 4 inch heels. She sat down and I started to work on her neck and shoulders again. I kneaded her deltoids for a few minutes, moving to her arms and eventually her hands, and got her relaxed back to the state she was in when we were still in the bar. She sighed as I rubbed the tension out of her muscles and said, "That feels nice." She had her eyes closed again.
"You know," I said, "I am not going to be able to do much more in the chair. How about if we move to the sofa and you let me work on your feet and calves?"
She only hesitated a second, then stood up. I took her hand and led her to the sofa where I sat at one end and patted the cushion at the other end. She sat down and carefully swung her legs onto my lap, keeping her thighs together. I did my best to appear as though I was not paying any attention to her hemline during the maneuver. She still had on those killer heels, and they featured a deep cut-out in the vamp, or top part of the shoe that covers the toe. I could see toe cleavage, which is a big turn on for me.