My Dinner with the Ladies

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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."

Carol reached over and gave me a peck on the cheek and said there's nothing to be sorry for.

I took the tools back to the garage, and during that time my hard-on went away. When I got back to the kitchen my clothes were on the table with an envelope. Inside was $80 for a half day's pay and a note from Carol thanking me and asking if I could come back next week.

The following week at work Carol acted perfectly normal and professional around me when she was in the office. On Thursday, I found a note in my mail box asking if I could come out again on Saturday to do more gardening, and other jobs.

I arrived around 8 on Saturday, Carol greeted me at the door and we went out to the back. She had drawn out a scheme for a flower garden, and asked if I could start to put it in. She said the plants were in the back of her SUV, parked in front, and that all the tools were in the garage.

I started to head toward the garage, when she called to me. "Owen, it's such a nice day, I don't think you need all those clothes. Besides, it will save me from washing them again."

I knew we had reached some sort of critical point. Depending on what I did, I would or would not be coming back. I really needed the cash, and $20 an hour made a big difference. Also, I remember how turned on I got last week and how I couldn't wait to get back to my apartment and jack off.

I smiled and pulled off my shirt. I kicked off my sneakers, then undid my jeans and slid them down. I reached over and pulled off my socks. All this time Carol just looked at me with a slight smile. With a shrug I tugged my boxers down and my dick bobbed up and down as I stepped out of them. Carol reached into the pocket of the jacket she was wearing and tossed me a bottle of SPF 45 lotion. "I wouldn't want some tender parts to get burned," she said.

Still facing her I lubed up my chest, arms and legs. I then worked the lotion on to my dick and balls and stroked my self. I was amazed I didn't pop an instant boner, but I could feel myself getting swollen. I turned and asked if Carol could do my back. She did my shoulders and places I couldn't reach, but said I could take care of the rest. I rubbed the lotion on to my white ass and turned back around. Carol had already started to make her way back to the house.

I pulled my sneakers back on and went to the garage and loaded a shovel, hoe, and rake into the wheelbarrow and pushed it back to the garden area. I then took the wheelbarrow back to the garage. Carol's SUV was in the driveway. I opened the overhead and realized I would have to go out in front to unload the flats of plants. Luckily there was a wall between the house and the street, but it was another turn-on to be there naked just a few feet from a steady stream of traffic.

I worked in the garden all morning with just one break for ice water. Carol joined me around 11 and we worked side by side. She was dressed in a t-shirt and cut-offs. We chatted and dug and planted, all the time with sweat running down my nude body. At 12:30 she said it was time for a swim and lunch. I followed her to the pool, she said I could take my shower first. I stood in front of her and washed the dirt and sweat off, giving a little extra time for my dick and balls. She then lifted the t-shirt over her head. I thought maybe I would get to see her naked, but she had on a top like beach volleyball players wear, and under her cutoffs, she had a matching bikini bottom. She rinsed and we both dove in.

Carol was a strong swimmer and we both fell into matching each other doing laps. After 25 laps, we both ended up in the shallow end. Carol asked if I would get the towels that were by the shower. I stood up and walked in front of her to climb out. I caught a glimpse of myself in the glass door of the cabana. I looked weird being totally nude. I then saw Carol's reflection behind me. She was looking at my reflection in the glass. She reached around to take the towel from me, and gently placed her other hand on my butt. It was almost an innocent touch, but it brought an immediate reaction from me as I got hard as a rock. She whispered thanks in my ear and then headed back to the table on the other side of the pool.

I dried off and joined her. She said there was a picnic basket in the kitchen with a cooler next to it, and directed me to bring them down. I went up and after entering the house went to find the bathroom to take a pee. It isn't easy peeing with a hard-on, but I managed. I gathered the basket, and cooler and headed back down.

Carol was not at the table, but I heard the toilet flush in the cabana and figured she had to take care of needs as well. I was laying out the lunch when I heard the cabana door slide open and closed. I was back to half-mast, but figured I'd have a little fun. It only took about three quick strokes before I was fully erect again. I placed a napkin over my wrist, like a waiter in a restaurant and turned with a flourish to announce that "lunch is served".

I was almost knocked over to see not only Carol, but also Maggie standing there.

Carol and Maggie actually giggled, then Maggie said, "What are we having? Something on a skewer I presume?"

I went into my best Adam pose and covered myself feeling like a complete idiot.

Maggie turned to Carol and asked, "Is he always this happy to see guests?"

That kind of broke the ice and we all laughed. I dropped my hands and said, "Obviously."

Carol chimed in that we should eat.

Over lunch I asked why Maggie had the same type of suit on as Carol. Maggie was surprised to learn that I didn't know that she and Carol met at Stanford, and they became both friends and the interscholastic beach volleyball champions for their Junior and Senior years. They even played on the pro circuit for a couple years while going to grad school. The suits were from those days.

Maggie was even taller than Carol, about 6'1". She had a mass of red curly hair, striking blue eyes, and tremendously long legs. She had a flat stomach like Carol, but seemed flatter in both the chest and butt. She was long and lean.

Maggie came over to help with the garden, explained Carol. After lunch, Carol asked if I would mind cleaning up and take the stuff back to the kitchen. I stood up and trying not to stick my dick in someone's ear, managed to pack up and haul the leftovers to the kitchen.

Maggie and Carol were back in the garden when I returned and we all began digging. After a while, I almost forgot I was naked. Carol asked me a couple times to go get some cold drinks or a tool from the garage. I began to enjoy serving her while being nude. Twice during the afternoon the girls made me rinse off the dirt and apply a new layer of lotion.

At about five o'clock, Carol announced we were through for the day. She said Maggie was staying for dinner and that I was welcome to join them. I half kiddingly asked what the dress was for dinner. Carol coolly replied I was fine the way I was.

They went to the house to clean up and I took another outdoor shower. I pulled up a chaise lounge and remaining naked lay down and took a nap.

I woke up with someone pulling on my toe. It was Maggie, and asked if we could talk. I said sure. She said we could do it as I helped her unload groceries and other stuff from her car. By now, I was almost used to walking around nude. Maggie led me through the garage and out to the driveway. She was dressed in Capri pants and a tube top. The top confirmed by suspicion that she was not well endowed in the chest department. She opened her car and started handing me bag after bag. With our arms full we made our way back to the kitchen. Carol was nowhere to be seen. As I was putting the supplies away, I commented that it looked like a lot of food for just one person.

Maggie said it was for a dinner party and that she wanted to talk to me about that. It seems there is a group of eight women who get together every month for dinner at one of their homes. This month it was Carol's turn. Maggie also explained that in addition to each lady trying to put out the most delicious meal, they also would have four male waiters, and the waiters would serve in the nude. The women would be all dressed, the men all nude. From greetings through cocktails, dinner and special desserts, the waiters would be totally bare-assed.

Maggie said that Carol hadn't ever hosted before. She was nervous about the dinner, especially since the hostess had to supply one waiter.

Maggie then explained more about the clothed female/nude male concept. She said all the women were educated, professional and classy, but they all got off on having a naked man serve them. I asked if that included her and Carol. Maggie replied that's why they're asking me to be their waiter. Each of the women formed a pair and brought their own waiters. In the past, Maggie's brother served as theirs, but when one other guy moved away, one of the other ladies made her brother a sweet deal and he took it. That left Carol and Maggie without a waiter.