Pool Boy Chronicles

It seems that word gets around quickly in small wealthy neighborhoods dotted with expansive mansions and well-manicured landscapes. A few weeks after I had helped Naomi and her college classmate Susan set up a reunion party on Mountain View Pass, I got a text message from a woman named Anna. She said that she knew Naomi and had been seeking references from her regarding pool maintenance services. Naomi had given her my number, and as I would find out later, also told her about my rather unique working arrangements. I texted back and told Anna that I would be happy to meet with her.

Two days later, I approached a large mansion in a rather private section of the neighborhood on Overlook Trail. Given the immense size of the home, I half expected to see a butler or maid answer the door when I rang. To my surprise, a very attractive woman in her 30's opened the door.

"Chris?" the woman said. "I'm Anna. I'm so glad you were able to come today."

"I was pleased to get your message," I responded. "I am always looking for new clients."

"I've known Naomi for years. We ran into each other at the farmer's market last week, and I mentioned that I was looking for a new pool maintenance person. She immediately gave me your name and a very strong personal recommendation as well. I hope you don't mind that she shared your number."

"Not at all," I answered. "It is nice to hear that I am getting good comments from my other clients. Do you want to show me the pool?"

Anna invited me in and we walked through a luxurious living room and family room area to get to the sliding door at the back of the house. I thought that the other properties where I had worked were large, but Anna's estate was incredible. As I looked across the wide green lawn to the pool, gardens, and private sitting areas, I was reminded of photos I had seen of the ornate landscapes of European castles from a different era.

"I've never seen a private yard as big and as beautiful as this one," I said. "It looks more like a public botanic garden."

"It has been a labor of love for many years," Anna replied. "My husband comes from a wealthy family, and he has given me his blessing to create my dream garden landscape in my own back yard. In the summer, I spend most of my time working or relaxing out here."

"I see you have two pools back here. The large one looks big enough to swim laps. I'm guessing the smaller one is designed to be a conversation pool?"

"Very perceptive," Anna said. "There are underwater benches that are perfect for sitting and talking with our guests, and my husband insisted we have an excellent sound system for times when we have large parties back here."

For the next half hour, Anna showed me around the pool area, pointed out the pumps and heaters that serviced the two pools and an in-ground hot tub, and explained the maintenance schedule that she hoped would fit my schedule. It all sounded great to me and once we had agreed on a day that would fit our calendars, I thanked her and began to head to my car.

"There is one more thing," Anna said as I was about to leave. "Naomi explained the rather unusual dress code that she has included in her contract with you, and I am curious to know if you have the same agreement with other clients."

"She is the only one," I replied sheepishly, surprised that Naomi had shared that information. "I felt a bit strange when she first proposed it, but now I really feel comfortable working au naturel as they say in France."

"They say that here, too," Anna said with a big smile. "Might I be so bold to ask if you would be willing to do the same thing here? I would double my usual payment, of course, just as Naomi said that she does with you."

"I take it that this detail is one of the main reasons you asked me to meet with you?" I asked. "You or your husband would not be offended by a nude pool boy working in your backyard? Other friends or guests who may be back here?"

"Silly boy!" Anna exclaimed. "We are very open minded, unlike many of our neighbors, I suspect. Our yard is completely private, and I can't remember the last time that either of us bothered with swimsuits in our pool. Many of our friends are equally comfortable swimming that way."

"I'm cool with it then," I said. "Besides, the extra money really helps with college expenses. I'll see you next Tuesday."

"One more thing and I will let you go," Anna said. "If I am going to pay double, I would like to see what I am getting for my money."

"I just figured that Naomi would have filled you in on all of those details as well."

"She did, of course," Anna answered. "But what she described seemed almost too good to be true. She does have a way of exaggerating, so I decided that I better see for myself."

"You're asking me to strip down right here so that you can check me out before you officially hire me?"

"I would like that very much," Anna replied with a sexy smile. "I love my husband and he provides very well, but he would never be confused with an Greek god if you catch my drift. Ever since I saw you at my front door, I started to imagine what you might look like without clothes. If you'd like, I can help get you started."

The offer and the opportunity were too good to pass up, and based on my other adventures this summer, I sensed that more good things might be in store for me. I kicked off my sandals and pulled my shirt over my head. I thought that might be enough to satisfy Anna's curiosity, but she just stood there with a look of anticipation in her eyes. It was clear that she wanted the full Monty, so I unsnapped my shorts and pulled them down. Anna's finger motion suggested that I was not quite finished, so I peeled off my underwear and stood before her completely naked.

"Oh dear," Anna said. "I owe Naomi an apology. You are indeed a big boy."

"That's exactly what Naomi and her daughter told me when they first got a look at me."

"So, Kayla has seen you naked too? Good for her, though it may be hard for her to find another guy on campus who measures up to you."

It turned out that Anna was interested in more than a visual inspection. She ran her soft hands over my back and lovingly squeezed my ass cheeks. She was even more attentive as she worked her fingers over my chest and down my torso. My cock was starting to react to her probing hands, and that brought a large smile to Anna's face. She knew I needed her to touch me where all guys beg their girls to touch them, and she did not disappoint. Her fingers felt so good as she stroked my shaft and gently massaged my balls. I was pointing up almost obscenely by this time and I wondered where this was leading.

Anna broke my reverie a few moments later when she said, "I'd better stop before this goes too far. It has been so long that I held a strong muscular young man like you. Please forgive me if I have been too intimate or too aggressive. You will do very nicely. Please pencil in a few hours on your calendar when you come next Tuesday."

I was not sure why Anna wanted me to set aside a few hours the following Tuesday since a typical pool maintenance regimen only takes about twenty to thirty minutes, but I did as I was asked and cleared my calendar before I arrived to start my assignment at her beautiful house. The pool area was deserted when I arrived, so I hauled my gear to the backyard and started my work. Anna came out a few minutes later wearing nothing but a rather sheer chemise and carrying a cup of coffee.

"You're right on time," Anna said, "but you seem to be a bit overdressed for the job."

"I didn't know anyone was home," I replied as I stripped off my shirt and swim trunks. "May I carry on with my duties?"

I was standing completely naked again in front of a married woman. As she had done the week before, she explored my body with her soft hands for a few moments. Eventually, Anna found a pool chair close to where I was working and watched me intently as I checked the chemical levels of the water and vacuumed the pool floor. A few minutes later, another woman opened the gate and walked over to Anna. The same thing happened shortly after that. Each woman was carrying a large portfolio, but their eyes were wide as they saw me. Now I had three women watching me as I did my pool duties in the buff.

"These are my friends Marisa and Emily," Anna announced as I worked. "We are members of the local Artist's League, and we get together every week to critique each other's work. We also do sketching sessions with models from the area to perfect our skills.

"He's gorgeous," Emily said quietly to Anna as she continued to watch me work. "I hope he will be our model for today."

I heard Anna tell her that she had not yet solidified that part of the arrangement, and then she walked over to talk to me. "You probably heard that. I kind of thought that you might be willing to be our model for the sketching session today, but that is totally up to you. I think you would make an outstanding life model, but you are free to say no and just pack up your equipment and leave."

"This is why you wanted me to block off a big chunk of time today?"

"The minute I saw you in the nude, I knew you would make a perfect model. You are an artist's dream, and I have been hoping that you would consider the possibility. I would pay you the same double hourly salary that I am paying you for the pool work."

"So, I just stand there as they do their sketches?" I asked.

"Pretty much. We will suggest a few different poses from time to time, but you basically hold some basic poses as we sketch."

"That sounds like easy money to me," I replied. "I can work on my all-over summer tan and get paid for doing it. I'll give it a try to see if I am any good at modeling."

Anna went back to tell her friends that I had agreed to model for them, and their smiles and applause let me know that they were happy with my decision. I finished my pool maintenance tasks while the ladies set up some chairs around a small wooden platform that had been leaning against the house. I set my equipment by the gate nearest the driveway and walked over to the group.

"We like to start with a pose that is similar to Michelangelo's famous statue of David. It has all of the characteristics of a classic nude pose, and it is a pretty ease pose to hold for a few minutes. Let your right arm fall to your side and flex your left arm as though you are holding a sling. Now shift your weight slightly to your right leg and turn your head as though you are sizing up your opponent."

With that set of instructions, I stepped up on the platform and became David for the next twenty minutes or so. I wasn't sure how I would feel standing naked in front of women I had just met, but within minutes, I felt totally at ease up on the posing platform. After the three were satisfied with my first pose, Anna guided me through several others using photos of classic Greek and Roman sculptures. At times, she perfected my poses by putting her hands on my body to show me how she wanted me positioned.

When I could, I tried to make eye contact with the artists to see if they were satisfied with my poses and also to see where their eyes were focusing on my body. Marisa appeared to be a young Hispanic woman, and she did her sketches very quickly. She was not content to use the vantage point that her chair afforded her, so she would get up and walk slowly around the platform as she sketched furiously. Emily, on the other hand, seemed to always have her eyes riveted on my groin area, and I could only imagine what her sketches would look like.

"It's like having Michelangelo's model standing right here in the flesh," Marisa gushed. "Our own living David posing for us."

"But fortunately for us, Chris here is far better endowed than the great artist's model," Emily smirked. "Anna has found us a fine-looking stud for us to study this week."

I had seen ads posted in the student union on campus seeking models for the life study classes in the Art Department, and I admit that I had given it some thought at the time. I had always wondered what it would be like to be the only one naked in a room full of male and female students, but as I stood there on the platform, I began to see why modeling had such strong appeal for some people.

Eventually, Anna called out that the sketching session was over. I asked if I could see the work that the women had done, and when Anna nodded her consent, I walked over to Marisa. As I guessed, her sketchbook was filled with dozens of quick figure studies, though none resembled a completed drawing. She explained that it was her way of taking visual notes and that she filled in the shading and other details later. Anna's work was more precise. I could see instantly that she was a talented artist, and I thought her sketches were both excellent and very flattering. I was most curious to see Emily's sketchbook since she always seemed to be focused on my groin as she worked. I was still surprised when I saw her work--each page featured a much larger than life representation of my cock and nothing else. Each sketch was so detailed that they might as well have been photos. She captured in sharp detail the shape of the tip of my penis, the veins and texture of the skin along the shaft, and the intricate folds of the scrotum surrounding my balls.

"It looks like someone has a special interest in one part of the male anatomy," I joked.

"Oh, don't mind Emily," Anna laughed. "We call her the 'prick chick' because that's all she ever sketches. We always joke that she is practicing for a job illustrating anatomy books for pre-med students."

"Don't lay it on me," Emily protested. "Chris is the one who was showing us his junk all afternoon. It's kind of hard to ignore such an impressive piece of manhood."

"Well, I hope I lived up to your expectations as a model," I said. "I should grab my clothes and equipment and head home."

"We were hoping you could stay a little longer," Anna said. "We usually kick back after our drawing sessions for some adult beverages and some pool time. We would love to have you stay."

"A cold drink would be great," I said.

As we sat and talked, I wondered if this art session was about to lead to something more risqué, and it was clear that Emily was badgering the others to turn this into a "hands on" situation. Anna threw cold water on that, however, when she announced that she had plans for the evening.

"Cool down ladies," she said. "I'm going to have to call this session to an end."

"Just a little longer?" Emily begged. "I want to get my hands on this big boy's beautiful bod."

"Nice alliteration," Anna quipped, "but it's going to have to wait until another time. Chris, you can tell you were a big hit today. Would you be interested in another session next week?"

"I'm cool with that," I replied. "This was easy!"

As I drove home, I kept thinking that something was bubbling just below the surface during my posing session. Maybe it was the facial expressions of the three women as they stared at me while they sketched. Maybe it was Emily's more overt announcement that she was expecting the session to get physical. Whatever it was, I was already fantasizing that the session next week was going to turn into something sexual. Little did I know what I was getting into.

I arrived at Anna's house earlier than usual the next week. Anna was there to greet me and remind me of the dress code we had agreed upon. She watched with anticipation as I stripped off my board shorts and T-shirt, and she gave me a big hug once I was naked. As I did my pool maintenance duties, I noticed that she was laying out a large sheet of plastic where the posing platform had stood a week ago. When the other women arrived, they helped her set out plastic pails and brushes in a variety of sizes. I was surprised to see a fourth woman enter the backyard.

"Chris!" Anna yelled over to me. "I want you to meet Hannah. She has been a member of our art group for many years, but she was not able to be here last week."

"Glad to meet you," I said as I walked over to the group. "I'm Chris."

"Oh my!" Hannah said with wide eyes. "I think he will be perfect for today's special activities."

"About that," I said. "What's with the plastic sheet and the paint buckets?"

"I was hoping to talk about this before the others arrived," Anna answered, "but they all got here too soon. We have been looking for an opportunity to try body painting as an alternative to sketching, and we all agree that you would be the perfect person to be our 'human canvas'. In case you are wondering, we will only use water-based paints. They are safe and easy to wash off when we are finished. Are you willing? I'm offering the same posing rate as last week."

"So, you want me to just stand here while you slather paint all over my body?"

"Body painting has become a very popular artform," Marisa said. "I did it once for a photo shoot and it was an amazing experience. It actually feels good to feel the paint on the skin, and the final product is so colorful."

The money for these art sessions was good and the women had already seen me in the nude, so it was not too big a leap for me to agree to the proposal. I watched as Anna and the others filled several plastic pails with paint in a variety of colors. I stood in the middle of the plastic sheet as the four women moved closer with paintbrushes. Anna and Marisa started on my back while Hannah started with a wide brush on my neck and torso. I was not surprised to see Emily pick a small brush and go to work on my penis. I think she had been dreaming of this since the last session.

"Look, everyone. Our handsome model has a heart on!"

I looked down and noticed that Emily had painted a bright red heart covering the tip of my penis. I was semi-flaccid at this point, but I knew that would not last long. She continued to paint the shaft with her brush, and with each stroke, I felt myself getting harder and harder. I had never been brought to full erection with a brush filled with paint, but I will admit it felt amazing. It was not long until I was rock hard, giving Emily an even bigger canvas with which to work. I stood patiently for several minutes as the four women turned my body into an artistic creation.

"Hannah. Come around back to see what we have done," Anna said.

"Amazing," Hannah said. "It looks like a living Peter Max poster. I love the bright colors."

"Precisely my inspiration," Marisa said. "Notice that we painted a flaming orange peace symbol using his ass cheeks to fill out the circular shape with the yellow symbol itself running down his ass crack to fan out at the bottom of the cheeks. It made me feel like a hippie from the 60's while I was painting it. The 'Summer of Love'."

"Of course, we added a lot of colorful rainbows and hearts and stars and guitars to create the Peter Max psychedelic look," Anna added.

"I love it," Hannah said. "I decided to go for a Keith Haring look on his chest and legs. Lots of colorful and playful figures interspersed with geometric designs. But you really have to get a look at what Emily has created."

All three women moved in close to watch Emily as she finished her creation. She had painted my scrotum a deep blue color and had added white speckles to each ball sac. She was in the process of painting alternate red and white stripes the full length of my erect cock so that the complete project looked like a stylized American flag. Anna grabbed her phone and was snapping photos of me from all angles so that I could see the body art.

"Beautiful work," I said as I scrolled through the photos, "but when do I get my turn? I have a little artistic talent myself."

I figured I would just get some sarcastic grins and protests from the women, but to my surprise, Emily slipped off the sun dress she was wearing. It turned out she was wearing nothing underneath.