Whistling Billy

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Whistling Billy

(I like a little background and a plausible set-up. Thanks for your patience. Everybody in this story is at least eighteen years old. Any resemblance to real people or places is purely coincidental)

My company is “Whistling Billy’s Pool Service”. My motto is “Your pool will be clean as a whistle!” (Of course, I don’t say when!) I’m only 29 which in this business is pretty young. The title Pool Boy seems pretty much of a myth. I know pool guys that are well into their 70’s. They’re a lot more common than hot strapping 20-year-olds.

In the five years I’ve been doing pools, I’ve learned a lot from those old guys about how to make a living at this. If I were filling out a loan application, my job title would be Swimming Pool Service Technician. There’s a lot more to it than skimming leaves. Keeping a pool system running involves a lot of equipment and skills and can actually be quite lucrative.

That being said, the day to day business is really quite pleasant. I’m a one-man shop. No employees and no boss! I bring my service equipment in and out through the gate to my customers’ back yards, do some cleaning, check some equipment things, test the water and add some chemicals and most of the time that’s about it.

A lot of customers I’ll see maybe once or twice a year. I take care of the pool and they send me checks. A perfectly satisfactory relationship!

Some customers, though, will come out to chat. This isn’t a bad thing. This can be a lonely job if house after house you don’t see anyone. Occasionally, I’ll go a whole day without any human contact. So, when somebody does come out to say hello, I’m usually happy to see them. As years go by, these casual visits turn into a casual relationship. They’ll ask me how my mom’s eye surgery came out. I’ll ask them how their kid’s soccer season is going. We get to know each other a little and it’s another nice perk of the job.

I’ve found there is another class of customer too: single women. Some are widows, some are divorced, some never married. Some have kids, some have a roommate or two, maybe they live with a sister, some live alone. Maybe they got the house in the divorce and need all the help they can get to keep the place up and running. The pool man can play a key part in that. So again, these casual relationships develop.

Once in a while, these women turn out to be not just alone and a little lonely but also horny! That’s where I tread very carefully. Just because they are nice people and horny doesn’t mean they are attractive.

I was a little shocked one time when this woman who was twice my age and overweight came on to me. She asked me to see if I could figure out why her kitchen garbage disposer wasn’t working. She was wearing a knee-length nightgown with a thin robe over it. I sensed some sizeable unrestrained boobs in there somewhere but the rest of the package was unappealing. I recall she had a strong whiff of perfume.

While I was down on the kitchen floor with my head under the sink, she was hovering around. She wasn’t really exposing anything (thank God) but she was offering me a peek if I chose to look. I chose not to. I pretended to be dumb as a stump and kept my eyes on the business at hand. I couldn’t get the thing to run and told her she would need a plumber. Maybe she had better luck with him.

Sometimes the single woman story goes a different way, though. Sometimes they are quite attractive and easily get my attention without any effort on their part. Maybe not blazing hot but still with a little personality thrown in, I’m interested. Of course, they are still customers that I prefer not to lose so I keep it very low key.

I do whistle. I’ve always liked to whistle a tune or whistle along with the radio. I don’t do it all the time but it’s sort of a practice of mine. I’m especially likely to whistle on my way into a backyard. I don’t want the customer to think I’m trying to sneak up on them. Now and then, I’ll come around the corner of the house to the pool area and the water is still sloshing and there are wet footprints leading to the back patio door. For whatever reason — nudity? — they didn’t want to see the pool man that day!

So, what am I supposed to think when I whistle and clatter into the back yard and one of these attractive younger women is just laying there on the lounge in a bikini working on her tan?

“Oh, Hi, Billy. I won’t be in your way will I?”

That was Pam. We had a casual acquaintance and I knew she was divorced and had two kids in grade school.

“Hi, Pam. No, you’re fine.” I’m not sure how she took that but I meant it in every way. “I want to thank you for putting away the pool toys. It’s a big help.”

“No problem, Billy. I’m getting the kids to do it.”

I always try to reinforce the behavior when a customer does the right thing. I said, “You are usually so busy. I don’t often see you just relaxing.”

“You got that right!,” she replied. “Wednesday is the only day that’s not programmed to the max with school things, Eryaman Escort soccer, PTA, and so on.”

“Are you still working?” I asked.

“Yup. That too. It’s only Tuesday and Friday mornings but I gotta fit it in.”

By now, she was laying comfortably on her back with one of those little eye cover thingies to keep from burning her eyelids. I understood this to mean she couldn’t see me. So, I ogled. She was fine. I’d guess 5′-7″, and just shy of plump. She was very curvy. I knew she worked at the gym but she wasn’t all stringy muscles with sharp corners. She was just fit and, well, delectable. Her boobs looked nice but not real large. I’d never seen her this undressed before but laying on her back, it was hard to get a full sense of her body. I liked the width of her hips but I couldn’t tell much about her butt. I kind of wished she’d get up and parade around a little.

She had a nice face, too. Cute but intelligent. And it seemed to me there was a little mischievous glint in her blue eyes. Her hair was reddish brown, auburn it’s probably called.

“At the gym, right?” I said. “Tell me again what you do there.”

“Pretty much just receptionist. Answer the phones, check people in and out, hand out brochures, stuff like that. The pay is ridiculously low but I get free access to the gym. That’s the real reason for doing it.”

I took a risk. “Well, looking at you, I’d say you’re getting your money’s worth out of that gym.”

At that moment, I was across the pool from her but she raised her head, took off her eye protectors, looked at me and smiled and said, “Why, Billy, it’s nice of you to notice.”

I smiled back but was too embarrassed to say anything.

She laid back down, covered her eyes again and said, “You look pretty fit too, Billy. Do you work out?”

“Nah, sloshing this pole around pools all day is a pretty good upper body workout. Also, I play soccer on an adult league once or twice a week. Good for the legs and cardio.”

I poured a half a gallon of chlorine in the pool and said, “Give it an hour and it’ll be ready for your lap-swim.”

“Thanks, Billy.”

“Well it was good to see you, Pam,” I said meaning it in every way. I took another risk: “And I like the new wardrobe…”

She lifted her head, removed the eye-guard, and with that glint in her eye said, “What? This old thing?”

She gave me a wry smile and said, “Speaking of wardrobe, what ever happened to pool boys wearing those short little athletic shorts. All I see are cargo shorts anymore. I guess those were the good old days, huh.”

“Well, I wouldn’t be surprised if you only ever saw them in movies or something. Still, you never know. Styles can change.”

“Well, I wouldn’t mind a little change.” She grinned. “Thanks, Billy, see ya.”

I grinned back and said, “Have a good week, Pam,” and clattered out the gate.

As my week went by, the pleasant encounter with Pam kept returning to my mind. I had had a fairly serious relationship with a woman that ended almost a year before. I had had a few dates since then but there was nothing really special about them. I even had sex with a couple of the girls. It was fine but nothing really clicked. And now Pam. Really? The divorcée and the pool man: what a cliché! And still…

Little by little, through the next week my mind was wrapping itself around a plan that would be just slightly risky. I rummaged around in my drawer and found some old soccer shorts. They were very basic, just plain blue nylon, not part of an actual uniform. They were a little shorter than uniform ones and a little small for me besides. I usually wore a Hawaiian shirt to work. But I found a white tank top.

So, Wednesday morning, I left for work with the soccer shorts in place of my boxers under cargo shorts and the tank top under the Hawaiian shirt. When I got to Pam’s, I wriggled out of the cargo shorts and left the Hawaiian shirt. While I was legally decent, I felt a little exposed. There were no pockets anywhere and I had to leave my wallet and phone behind. I had nothing but my truck keys tucked into the waist band of my shorts.

“Well, here goes!” I thought.

When I came around the corner to the pool deck, I was a relieved to see nobody was there. Then after all that mental buildup, I was a little disappointed. It’s a little-known fact that often, due to reflections and light and shadow, the pool man can’t see into the windows of the house. Someone could be standing right inside waving and the pool man looks like he’s rudely ignoring them. It’s just that he can’t see. But I sensed movement through the kitchen window which I ignored.

I was working my way around the tile line when the sliding back door opened. It was Pam. She carried out two tall glasses of iced tea and set them on the patio table. She was wearing a light blue men’s work shirt closed with a few buttons as a coverup. Her tan and shapely legs looked fine!

She looked at me across the pool and said, Sincan Escort “Well, check out that new uniform! I like it. Come over here ‘pool boy’. Have some iced tea.”

I grinned and headed around to the table. She watched me approach rather blatantly, I thought. It was a little embarrassing. We both sat down and I sipped some of the tea.

She looked at me over her glass and said, “Billy, thank you for taking my wardrobe suggestions to heart! It’s very thoughtful of you.” She had that radiant smile and that mischievous glint in her eyes.

“Well, Pam, the customer is always right,” I said.

“So how is your week going?” she asked as she picked up her glass and took another sip.

We chatted amiably for a while with no obvious flirting. I got to glance at her face and her hair and her hands and arms and the top of her chest. The more I looked, the more attractive she became. It was not perfection but her looks and personality all fit together comfortably into a charming whole.

We had mostly finished our drinks and I said, “Pam, this is great but I have a long list of pools to clean.”

She got up and said, “Yeah, and this is my sliver of time to work on my tan.”

I resumed my work and she took the glasses back into the house. When she came back out, she had lost the work shirt and was carrying a book, a towel and some sunblock. She was wearing a different bikini from last week, a black one. It covered about the same amount of her body but was somehow less substantial. More flimsy. I don’t know…

We attended to our tasks: she was applying sunblock while I was doing the pool stuff. I was trying to watch her without being obvious. I doubted that I was doing it very well but she didn’t appear to notice my sideways glances. It was exciting to see her rubbing her arms and legs and belly and shoulders with cream. But I tried to contain myself. I could feel my dick twitching under the thin nylon of my shorts but I was pretty sure it wasn’t a tent yet.

As I was getting closer to where she was, she said, “Look, Billy, I know it’s not in your job description but could you just do the middle of my back? It won’t take a second.”

“Sure,” I said.

She put a dab of the cream on my fingertips and turned around. “Right between my shoulder blades.”

I proceeded to apply the cream. Her skin felt smooth and warm and her back muscles felt firm and strong. The gym, I thought. From this vantage point, I got to freely check out her butt. It was splendid! Rounded everywhere but not fat. I realized she had a very narrow waist that set off her womanly hips to great advantage.

“Get it right under the bra strap. That’s good.”

I hesitated as if to ask, “Am I done?” I got no answer.

She turned back around and started coating her chest. Then, she got a big dab on her fingers and reached right inside the cup of her bikini top and started massaging it into her breast. This caught me way off guard and I couldn’t do anything but gawk. She proceeded to the other breast and looked up as if she just noticed I was there.

“What?” she asked innocently, “This is just for later when no one is around.”

That impish smile and twinkle in the eye again.

I was really twisted up at this point. That fine line again. Should I just grab her and kiss her? Then what?

“Oh, Billy, I’ve been wanting you so bad…” or “HELP! RAPE! Get off of me you animal!”

I eased away from her and she gave me an enigmatic smile, adding to my confused state. She laid down on the lounge chair to continue her tanning and I worked my way around the pool to finish up. I decided a complement wouldn’t do any harm.

“Ya know, Pam, servicing your pool has become my favorite stop of the week.”

“Then, I guess I can count on getting my pool serviced next week too?”

“Oh, yes ma’am!” I said.

“Bye, Billy. And Billy,…”


“I hope you stick with the new uniform.”

I clattered through the gate and back to my truck. I was putting the cargo shorts back on when I noticed the front of my sport shorts had a pretty good size wet spot. Precum. “Aw, jeez,” I thought wondering if Pam would have noticed. Well, if she did, she might be gratified that her teasing is working.

My thoughts turned to the Pam Situation often that week. I pretty much decided that if she kept up her flirting one more week, I would give her a strong sign. Break through the wall. Cross that fine line. Schedule be damned!

The next Wednesday, I rushed through the first few pools so I would maybe have a little extra time at Pam’s late in the morning. I shed my shorts and shirt and was back “in uniform”. (The trunks were freshly laundered and stain free.) I was a little early but she was already out by the pool. She was seated on a chair at the patio table, wearing the blue work shirt again, reading a book. As she looked up and grinned, I noticed a pitcher and two glasses. One glass was unused and the other was half full.

“Hi, Etlik Escort Pam,” I said, “Is that a margarita you’re drinking?”

“How did you guess?” There was something in her voice and look that made me think it wasn’t her first one. “Will you join me?”

“Well, it is a little early but they do look refreshing.”

She stretched out a bare foot and slid a chair away from the table. I sat down. She poured me a glassful and topped up hers.

“I felt like a vacation this morning. Pretend we’re at a seaside café in Puerta Vallarta. Right here by the water.” She gestured to the pool. “The sun and the warm breeze are real!” She laughed just a little too gaily, I thought.

Still, it was a pleasant enough scenario and I could buy in.

“Si, Senorita. El dia es muy Bueno. Gracias!” I said probably butchering what little Spanish I had. We clinked glasses and sipped.

She said, “I’m glad to see you’re sticking with the new uniform. One thing concerns me though. The upper parts of your thighs aren’t tan like the rest of your legs. Aren’t you worried you’ll get a sunburn?”

“I hadn’t noticed,” I said. I slid the hem of my shorts up toward my hip an inch or two and said, “Oh, I see what you mean.”

“May I offer you some protection?” she asked, holding out a bottle of sunscreen. I went to take it but she pulled it back and said, “Maybe I should apply it since it’s hard for you to see.”

“Good idea!” I said with genuine enthusiasm.

We both stood up. I just held still while Pam squatted down in front of me. Watching her carefully, I got the distinct impression that she wasn’t wearing the bikini under that work shirt. As she started applying the sunblock just above my knee, I could see down the front of her shirt and her lovely tits were swaying freely as she worked. I could feel my cock swelling some. She worked her hands up my leg till her fingertips were under the hem of my shorts. She was really into her work and was rubbing away with both hands. My dick continued to swell and it was at her eye level and less than a foot away from her face but she didn’t mention it. Neither did I. I was curious to see where she was going with all this.

Now her fingers were spreading sunblock beyond where it was strictly needed. They were running up the bottom of my ass cheeks and in front, tickling the hair on my balls. The treatment was really having an effect on me and my cock showed it.

She said in kind of a husky voice, “I see you’ve gone commando in your new uniform.”

I said, “From here, it looks like you’ve gone commando too.”

She pulled the front of her shirt away from her chest and looked down. “What?” she said, “I must have forgotten my bikini.”

She looked up at me with a direct and mischievous look as she undid another button on her shirt. Then she proceeded to my other leg. By now, my dick was quite hard and pushing the front of my shorts out. With her vantage point and the light, I suspected she could see the whole package through the leg of the shorts. Still, she didn’t mention it and worked the cream into the skin of my ass with one hand while the other one freely bumped into my ball sack.

“I can tell you’re doing a thorough job,” I said.

At this she stood up and said, “Done. I’m sure you’re well protected now.”

I reached my arms around her back and pulled her in for a kiss. She didn’t hesitate. She grabbed me in a fierce hug and we kissed hard. Almost instantly our mouths were open and our tongues were wrestling around with each other. After a minute or two we broke apart.

“Come on,” she said, “we’re going inside.”

She took my hand and started toward the house. With her other hand she was undoing buttons on her shirt. Just inside the sliding door was like a den with a sofa, a stuffed chair, a coffee table, a tv and so on. She wriggled out of her shirt and was totally naked. God, she looked good! Curves everywhere but firm and trim. Wonderful tan breasts with half dollar size nipples, a little darker brown. Her nipples puffed out a little and on the ends were a couple very prominent points. World class!

It registered on me that her ass was tan also and I briefly imagined her sunning out by the pool when no one was there. She stood facing me with her legs slightly apart and just let me look. She was watching my face as I studied her form. I looked at her pussy, completely bald and smooth. Were those her labia I see hanging down just a little at the bottom? This was a dream! She was a dream!

“Alright, my turn,” she said. “Get that shirt off.”

As I stripped off my tank top, she grabbed my shorts, worked them over my stiffy and pulled them down. Then she stood back and studied me as I had her. I felt a little self-conscious but fair is fair.

“Nice,” She said. “Now help me.”

She took one end of the coffee table and I took the other. She gestured with her head and we moved it toward the TV, opening up a big patch of rug. She grabbed a comforter that was folded up on the sofa and gave me one end. We spread it on the floor.

“No rug burns,” she said.

Then she got down on her knees and pulled me down with her. We embraced and started kissing again but it wasn’t long before she lifted her knees, one on either side of me and rolled onto her back with me on top. Pam knew what she wanted and was going for it!

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