The pool cleanersStory by WinterWoollyWetboyPosted 1/12/25 506 views
Hello fellow wet lookers.
Here's another story from my younger days. I was in my early 20s and temporarily out of work. I saw an advertisement for a pool cleaning job & knew that for obvious reasons this would be a line of work that was right up my alley. I responded to the advertisement by phone & was told the job requirements.
Apparently I was to work in a large country club style resort & needed to be dressed appropriately in smart casual country & western style clothing, ie neat brand new very dark blue or black jeans & a Western shirt with a cowboy style hat. I had to report to the resort on the outskirts of our small inland town for a interview. I was told to be prepared to start immediately if successful & to be dressed as described & ready for work that day. I reported for duty wearing my brand new, slightly too baggy & oversized very dark blue jeans and my brand new blue cowboy style long sleeved Western shirt. It had double pockets with flaps over them & nice pearly white buttons. It would look very smart for a job interview of this kind. I think I looked like Woody from the Toy Story movies. I was a real cow poke looking guy. Underneath I would wear my underpants briefs and my singlet vest. For some reason I was required to wear a white tee shirt underneath my Western shirt. At the time I didn't have one because my mother never let me wear tee shirts so I wore a long sleeved white cotton turtleneck skivvy as an under shirt. I had not been been living on my own for long & hadn't had enough time to purchase such luxuries yet. I would have long white thick socks and my leather elastic sided cowboy boots with a cowboy hat & Western style cowboy belt. I was a country boy in a small inland town about to start work at a very expensive & quite exclusive country club resort & this suited me well.
I was told that I would mainly be working in the pool area as a pool attendant & would be expected to also clean & maintain the swimming pool. I was told quite firmly that I would need to be dressed in this clothing at all times & under no circumstances except for a life saving emergency was I ever to enter or bathe in the pool itself. That suited me well because I was was going to get off on staying out of the water while the guests would be able to swim & hopefully there would be some pretty hot bikini clad girls doing just that while I had to remain dry & hot dressed in heavy blue jeans & cowboy attire. After all didn't they have long poles & things for cleaning pools without getting wet? Who knows somebody might actually push me in the water. It might not actually happen but it would be nice if it did. If it didn't happen the fact that I had to stay dry while others got wet would certainly be a serious turn on.
I was told that I would get a trial run & I would be working with a partner. I was soon introduced to this partner who turned out to be a very hot looking girl about the same age as me. She was an absolutely smashing brunette. She was wearing long brown leather cowgirl boots, cowgirl hat, neat tight fitting very dark blue jeans & a long sleeved Western shirt that was the female version of mine. I think she had a long sleeved white tee shirt underneath it all. Her gorgeous breasts shaped her shirt beautifully & it was hard not to look at them or think about her wearing that white shirt wet. She looked so hot wearing this cowgirl clothing. Can you just imagine those clothes all wet & shiny? I was quite turned on by the appearance of her & she turned out to be very nice bubbly friendly kind of girl. We hit it off straight away.
We soon arrived at the very upmarket resort which had a very nice large pool. We proceeded to set up the equipment that was necessary for the job. The pool looked quite clean to me and didn't seem to need too much work at all. The first job was to set up the vacuum cleaner which was connected to a long telescopic pole. A fat cowboy manager with a serious face informed us that we were there to work & not mess about or bathe in the pool or we'd be dismissed immediately. He told us to thoroughly vacuum the sides and make it clean as well as clean the surrounding pool areas & bring drinks & light snacks to the poolside guests. Once John Wayne had left we started laughing & joking and having quite a lot of fun cleaning the pool & occasionally serving the guests. Some of these bikini clad girls were absolutely gorgeous to behold & the viewing was great
The weather continued to get hotter & we started to feel quite hot & sweaty. The work was definitely harder than we had both realised. Occasionally we would lightly splash each other. She said, "Wouldn't it be so good if we could go bathing. What a shame we can't " I agreed that this would be really good too but I knew we would lose our jobs so we continued to work hard. Suddenly out of the blue she said, "Why don't we just strip down to our underwear and have a quick swim while Fat boy was in the field on his tractor." I was very turned on but also very self-conscious even at this age. I could not be seen in my underpants especially in front of this girl. I declined the offer because also I didn't want to lose this job even though it was really starting to get to me. I told her that if she wanted to she should go ahead and enjoy the water. I was sorry I hadn't brought my bathing costume now as it would have been really nice to swim and the water looked very nice and inviting. She was egging me on badly now & it was so tempting. A thought had however entered my mind that maybe if I had turned my back to her there was a possibility that she might just push me into the pool fully clothed. She seem to be a cheeky sort of a girl and this could be a very real possibility it might not happen but hey wouldn't it be fun if it did and even if it didn't I could be turned on by the fact that I was dry and she was wet. I turned my back on her and started to remove the vacuum cleaner from the pool
I was standing right next to the edge when I heard a another girl shriek with delight. I realised it was a friend of my partner. She was really hot clad in a very skimpy bikini. It was hard to take my eyes off her. I started firming up immediately & felt my manhood straining against the heavy thick denim of my new blue jeans. She laughed & said, " Oh look, I think he really likes us. Why don't we all have a swim?" I looked at the inviting water longingly. It was so tempting. My partner shook her head. It was too much of a risk. They looked over to see where John Wayne was & saw that his tractor was a tiny puff of dust miles away. I wouldn't have minded at least getting splashed. The legs off my jeans were burning hot by now & my armpits were very wet & sweaty. Her friend laughed & pointed out the fact that I was wearing a white turtle neck under my Western shirt." Who would wear a turtleneck skivvy on a hot day like today especially under a cowboy shirt? That's a winter shirt & a turtle neck skivvy. It's what you wear instead of a tee shirt in winter, a sort of long sleeved winter tee shirt. Even a short sleeved tee shirt is too hot to wear under that shirt. What a country boy you are. Come on you too. You both need to lighten up." She was pretty hot but a bit of a spoilt Karen & her demands for food & drinks became a bit much throughout the day. She regularly complained about the way we served her & became a bit of a pain in the arse as she got more drunk. Finally she slurred something about how we'd have to be punished for our sloppy service. I was uncomfortably hot by now & my jeans legs were starting to burn my legs big time. My turtleneck skivvy & long sleeved cowboy shirt by now had wet armpits, collar & the back was soaked with sweat. My hat was making my head & face run with sweat & I'd just about had enough of her whinging & whining. "Well I said loudly. I've done everything I can to make your day as pleasant as possible but I can only do so much. I'm hot & tired & I've had enough. If you're going to complain to the management there's not much I can do. We've done our best." She smiled cruelly & said, " No I'm not going to complain because I sort out things my way. You will definitely have to be punished now though.
She threw her arms around both our necks & led us both to the edge. I had a feeling about what was to come next. I tried to break free but it was too late. Sure enough she leaped off the pool edge taking us both with her. I realized I was going in whether I wanted to or not so I just let it happen and plunged face down into that swimming pool with a heavily clothed country & Western style heavy denim clad splash. I was still wearing everthing including my leather elastic sided boots & socks. Suddenly we where treading water fully clothed in our Western wear. The water was pressing in on my jeans & shirt layers. It felt so refreshing & good. " There you are. Ive dealt with the problem. You wete just to hot & not working hard enough. Now you have no excuses because now you are cooled down. She looked at me suddenly in a sexy way. You look so hot now that you're wet. Aren't you a very naughty wet cowboy. Her sexy voice & being in the pool wearing my best clothes at work really turned me on & I felt so suddenly horny as I was treading water. When I rubbed my legs together I could feel an erotic feeling in my knob as if I was masterbating. I nearly creamed my jeans a few times. White frothy water foamed around us as people laughed, clapped & cheered. Our jeans were so lovely & shiny. But our cowboy hats were suddenly very floppy. We threw them to one side & had a huge splash fight immediately. I made a mock attempt to protest to add to the illegality of my fully clothed entry into the pool. however it was hard to hide the fact that I really love the way long sleeved shirts puff up into a big hump on ones shoulders when one is bathing fully clothed. They could see by by my shiny dark blue jeans bulge that I was turned on big time. I just couldn't hide it & afer I'd drunk several beers & mixed spirit drinks I stopped bothering to hide it. I became turned on by the fact that everyone could see it trying to burst out of my shiny dark blue jeans. I eventually confessed that I was as horny as hell & this made them both laugh. I was still a bit apprehensive about what to do about how we would get our clothes dry. We had absolutely nothing to change into.
My work partners friend said, "Surely you must have a change of clothes? I'm surprised in this line of work that you don't. Wouldn't you expect to get wet now & then? Did you not think this could happen?" I laughed and answered no because it was forbidden to bathe at this job. I told them that it was generally expected that we wouldn't find ourselves bathing in a swimming pool wearing our best clothes. "They are brand new and I've just worn them to the job interview this morning." They laughed and said, "He doesn't know much about this line of work does he?" I laughed in return and I stated that I had not planned to get wet when I arrived here for work. "This is definitely not allowed." She laughed and said, "Of course not but what they don't know won't hurt them will it? I'm surprised you didn't realise that there would be some bathing involved in this game. I guess you learn something every day don't you? You are gonna learn that it will take all day to dry out those clothes & you're gonna be wet all day in your heavy wet jeans, boots, a fucking turtleneck skivvy and that country style shirt. Fancy bathing dressed in all those Western clothes with boots as well." I think it was turning her on & my partner didn't seem to mind at all either. I briefly wondered If they were both into wetlook. I'll never know I guess.
We played around, & flirted for a bit & then it started to get very steamy. My lovely work mate put her arms around my neck & started to pash me off wildly. She didn't care who was watching & next thing we were madly humping each other in our wet Western wear. Her gorgeous dark brown hard was flowing free & smelt wonderfully sexy. I couldn't hold it back any linger & neither could she. We both climaxed for what seemed like forever moaning gently. I completely creamed my brand new dark blue shiny jeans. We floated blissfully on our backs enjoying the post orgasmic glow. We then played in the pool like silly kids as if we were wearing our bathing attire.
We were completely distracted from the reason we were supposed to be there. We were supposed to be working. We suddenly realised that Tractor Boy was getting closer. We hurriedly left the pool, tipped the water out of our boots, wrung out our socks & got back to work dripping everywhere. The bar staff laughed & said. "Half your luck. I wish we could've joined you. Don't let Fat bum catch you though or you'll both be straight out the gate." Well fat boy didn't catch us & we continued to work until we had mostly dried off. At the end of our shift he came in & paid us before sitting down miserably & drinking his beer. He did look at us a little strangely however because we were still damp but he didn't say anything.
I blew my first wage taking those two out for dinner that night but that wasn't the only thing that got blown as we all ended up in a threesome that night. It was great for a while until I realised I couldn't afford to keep paying for girls who where such great fun. The trouble was that my work partners friends had expensive tastes for a country boy on low wages. Eventually we parted company on good terms & got on with our respective lives. I often wonder where they are now. We were pretty good pool attendants it must be said. Here's a recent photo of me wearing dark blue jeans, dark blue singlet vest, a light grey turtle neck under a blue country & Western shirt. I was wearing boots & winter socks & a baseball cap. I swam wearing these in a pool recently. Sorry I don't have any old photos from the time the story occurred.
Cheers, Winter Woolly Cowboy.