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After college, I didn't have much going for me. I had worked out a deal with the local Y where I did fitness training in exchange for a free membership. I lived with my brother for free and picked up a few bucks being a waiter at a college bar on weekends.
I played a lot of squash, and that's where I met Tom. Occasionally he'd come to the Y looking for a game. We played and found it was good competition.
He owned a local stock brokerage and was a squash fanatic. We set up a weekly match, and as we got to know each other he took an interest in me.
He offered me a job with his firm. When I said I knew nothing about investments, he said if I was willing to start at the bottom, he would teach me. So, I became a glorified office boy. I did the mail, answered phones, did photocopying, went to pick up lunch, and did anything else the brokers wanted.
Tom's office was in an old grade school from the 1870's. He completely refurbished it into super-cool space. In the basement he made a small gym, complete with two locker/shower rooms for men and women. He converted an old attached garage into a squash court. There was a glass door from the workout area into the court.
Each day after the market closed, Tom and I would play squash for an hour, then shower and go to his office, have a light dinner, and he would talk to me about the market, why he was recommending certain stocks and how to deal with customers. I was really learning the business.
One night during our squash match I noticed Tom's sister, Carol, at the glass door. She runs a data management and computer consulting firm, supplying all the IT services to Tom's firm. After our match she and Tom started into an intense discussion about the need for a new computer network for the firm. She needed to get his Ok and had trouble getting time to talk to him all week. While they were talking, the three of us kept heading for the men's locker. Carol didn't even seem to notice and kept making her case to Tom. In the locker, he immediately started to strip, and I thought Carol would leave then. She didn't and Tom nodded to me to get undressed so we could get to our showers. Tom hated to wait to eat his supper.
I felt a little uncomfortable, but figured what the hell. So I turned my back to them, stripped, and wrapped a towel around me. I don't think Carol even looked in my direction. Tom just kept up the conversation while being completely nude.
The shower area is a tiled room with four shower heads against the far wall. There is no door, just an opening between the locker room and the shower. I took the shower farthest to the right. Just after I adjusted the water, in walks Tom and takes the space next to me.
Tom is talking, but not to me. He is still going back and forth with Carol, whom I now realize, is standing right in the doorway looking at both of us. I was already facing that way and didn't want to appear to be too freaked out, so I just started lathering up. I figured, maybe this is normal and I shouldn't be uptight. I was just getting my crotch all soaped up when Carol looks directly at me and says, "Well, what do you think?"
How am I supposed to have a normal conversation with the person who is my boss's sister, and a beautiful woman, while standing naked with my hands on my dick? Needless to say I didn't make much of a sensible reply. She shrugged and turned her attention back to Tom. Meanwhile, I finished and rinsed off.
I grabbed my towel and went back to the locker. Carol followed me and sat on the bench while I dried myself off. Her head was now close to eyelevel with my crotch. She said that Tom is frustrating at times and resistant to new technology. She was so intense that I think she did not realize she was practically talking right into my "microphone". After about a minute of me standing there getting dry and her going on a little rant, she seemed to snap out of it and looked directly at my dick. "Oh, I, uh, guess you probably want to get dressed. I should probably wait upstairs." She got up and left.
Tom came out and toweled himself. "Hey, don't let Carol bother you. She gets pretty wound up on some things and looses a lot of perspective. I hope she didn't offend you, but I think she was so singled minded that she didn't think it might be a problem that we were naked. She and I never had hang-ups about our bodies or being naked around each other. Sorry, if it offended you."
I laughed it off and said, "no problem."
I was a little apprehensive about coming into work the next day, and felt I might be embarrassed to see Carol. Thankfully, she wasn't there. It seems she and Maggie, her right-hand person, had gone off to Boston for a computer trade show and seminar.
It wasn't until almost a week later that Carol spoke to me. I was in the copy room running a bunch of reports when she came up to me. Instead of apologizing, she said that Tom indicated I could use some extra cash. I was barely surviving on the entry level pay and was always looking for ways to earn a few bucks. She said that with summer just about here, she had a lot of work at her house. If I could clean the pool, do some gardening and general odd jobs, she would hire me for Saturdays. I agreed and said I'd come this weekend.
Her house was in one of the nicer suburbs of Boston. It had a wall, a gate and a long curved driveway. The house was huge and all brick. I parked my old Civic next to the garage and rang at the front door. Carol answered and invited me in. She immediately addressed the house. "I know what you're thinking, but this house was our parents. When they died in an accident, Tom was married and had his own place, so I took over this house. It's huge, but they also left a nice trust fund that helps pay the costs."
She showed me around the downstairs and then led me out to the back. She was replanting the edges of the walkway that went from the house down to the pool area. She quickly showed me what she wanted done, and then left me to my work. I was at it about two hours, when Carol came out with a jug of ice water. I drank it and continued for another hour before I finished planting all the new flowers and filling in with bark mulch. For early June, it was extremely warm in Boston, and I was sweating. Carol came out and said I should clean the pool and then take a swim before lunch to cool off.
The pool area was all brick and flagstone. There was a tool shed and cabana on the far side. There was also a small platform that was the base for an outdoor shower. I was a swimmer in college and knew a lot about pools, so I didn't need instruction from Carol. I finished in 45 minutes. Carol came back down with a towel and said I should rinse off in the shower, take a dip and then she'd have lunch for me.
I told her I didn't bring a suit, and she said that after last week there were no surprises. She turned and went back to the house. I figured if she didn't mind, a cool swim would feel great. I stripped out of my t-shirt, jeans and boxers and took a quick rinse off in the shower. I dove in and started doing laps. I liked to do at least twenty-five three or four times a week to help keep in shape.
I stopped after twenty-five and rested on the pool's edge. The first thing I noticed was that my clothes were gone. There was a towel and a pair of flip-flops, but nothing else. Carol called out from behind me to come and get lunch. I turned and saw that she set some food on one of the poolside tables. I asked about my clothes and she said they were so grungy from the planting that she was washing them. She pointed out the towel she left for me. So, I pulled my self out of the pool, and, keeping my back to her, dried my self off and wrapped the towel around me.
I walked over to where Carol had set the lunch. There were sandwiches, chips and a bucket of beers. Carol had on a Speedo one-piece blue bathing suit. I always thought that she had a good figure, but she dressed so conservatively at work that I wasn't sure. She is tall, about 5'11", with long slender legs. She has shoulder length blond hair that is usually pulled back, but today hung loose in soft waves. Since the bathing suit tends to flatten out a figure, I couldn't really judge her breasts, but they looked to be round and firm. She had a towel wrapped around her bottom, so I couldn't get a look at her back. Her stomach was as flat as a board. We sat down and then she said she had forgotten the relish dish, and would I mind going up to the kitchen to get it.
I stood up to go, and Carol looked me in the eye and asked if I really needed the towel around me. I didn't know what to say, and she said, "Owen, really I've seen it all. Relax."
I undid the towel and dropped it on the chair. I walked up to the house, found the tray and brought it back. When I returned, I noticed that Carol had folded the towel and put it on the patio near her feet. I assumed this was a hint not to try to cover back up.
Carol and I talked about work, her passion for gardening and my life. When we were finished I offered to help clean up. We both carried dishes and leftovers back to the house. In the kitchen, I rinsed the dishes and she put them in the dishwasher. I was beginning to feel almost comfortable being nude in her presence.
Carol asked me if I would mind looking at a slow draining sink in her bathroom. We went upstairs and into her bedroom. The fact that I was naked with a clothed woman, in her bedroom, did start to get me a little excited. I know I began to swell, just a little. I looked at the sink in her bathroom, and figured I could unclog it with a plunger or by undoing the trap. She said she had tried plunging, but had no luck. I asked if she had any tools and she directed me to the garage. I found a wrench and a bucket on the shelf, and brought them back upstairs. When I went into her room Carol was standing with her back to me at her sink. She had taken off her towel, and was still in her one-piece. I got a good look at her ass, which was perfect pear shaped with tight looking buns. I immediately went to half mast.
I told her I could fix the drain, but had to get under the sink. She moved aside as I opened the vanity and began to move stuff out. I lay on my back and squirmed under the sink. I asked Carol for the wrench. She reached it into me while placing one hand on my bare thigh. I now went to having a good semi-erection. I loosened the drain plug on the trap and asked Carol for the bucket. Again she laid one hand on my thigh as she passed it to me. I became completely erect and totally embarrassed. I undid the plug and let the water drain. I poked around and pulled out a wad of rubber bands and hair that seemed to be causing the clog. I put the plug back in and squirmed back out.
I stood up with my member in its full and upright position, and said "Sorry."
