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From Pool Boy To Cabana Man

How A Pool Boy Turns Into Cabana Man Is Every Mans Dream

By Casey KellerPublished 4 years ago 11 min read
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If you can withstand eighty percent humidity with temperatures in the eighty's year-round except for during the rainy season I have the most excellent place for you to visit. It's at my place in the Maldives. The weather is breathtaking every day of the year. The water is just right. Sand tickling your toes. The beaches are pristine white and golden sands much like the bodies down here. Everyone has nice golden suntans. There's not a body down here that has bikini lines. Everyone is beautiful in all shapes and sizes. It's the perfect place to be. The food is ethnically a little different but still has similar tastes as to that as of being in America.

Even I don't have any bikini lines on my beautiful five-foot-seven-inch frame with my black hair and big tits, big beautiful plump red lips as I sit here sipping a Maitai looking out on the jetty's that go from island to island. Southeast Asia is beautiful. What made me want to stay here though wasn't just because of the weather and the women. Yes, I am a bi-sexual woman. I like women just as much as I like men and sometimes both at the same time. There is nothing more exhilarating than having a man fuck me while a woman is licking my clit at the same time and having another woman sitting on my face.

I first met Jake when he would come to my place to do the weekly maintenance and cleaning of my pool. Jake, even at 17 is a very good looking young man. He has broad shoulders and abs that you could go surfing on. His arms are like cannonballs, and legs built like palm trees. A very motivated young man who in-between cleaning pools also worked as a barista in the mornings with a bunch of cute petite women, Giselle, Brandy, Adaline, and April. He also worked as a mechanic at a small garage with his dad. I admit I probably stalked him a bit always getting my mocha caramel skin fat milk latte' with three shots of espresso, and getting small things fixed on my Honda Accord. He was always ready and willing to help me.

Sometimes I would think that he had a crush on me as well. How he would ask questions about sex and girls made me think that he was still a virgin. I couldn't imagine that though with where we live and the abundance of cute girls and women and the body that he has. I would enjoy our conversations and would occasionally see him stealing glances at my shapely legs, my big tits, and my big red luscious lips. He was always very considerate though and would always hold a gaze with my eyes. Sometimes our looks seemed to be very intense. I soon found out why. His birthday is in November, so he's a Scorpio.

One day though Jake got my attention when he asked about oral sex. He had asked what feels better to a woman, licking her clit or sticking his tongue inside her and about the amount of pressure? I had to tell him that all women are different but love consistent movements of the tongue on the hood of our clit that gets a woman off. I had to ask if he had a girlfriend and if he was trying to get her to the big orgasm. He responded with a no but that he had someone in mind with whom he wished that he could practice on. It made me think that he was thinking about me. I was hopeful but didn't seduce him. I could see his cock getting hard as we had talked more about it. I wished that it was me that would get his first load of hot sticky cum in my mouth. But I had a better plan in mind for helping this fine young man lose his virginity. I would invite all of the girls down at Starbucks to come to my place and we would give him a surprise titty birthday party and let him jerk his cock off on all of our tits. So I became friends with Giselle, Brandy, April and Adaline and would talk to them when I would go down to Starbucks when I would get my triple shot of espresso mocha caramel with skim milk. I had talked to each of them and if they would want to do this and they all were in but thought that it would be better and more fun if they each could bring a friend. After all, it's not a party until you have 9 beautiful bare-chested women to jerk off to.

It was about a week before Jake's birthday. I was wearing a skimpy swimsuit that barely covered my big tits and I was fantasizing about having sex with Jake. I could hardly wait for his birthday to get here. I laid there in my hammock watching Jake while he cleaned my pool. His body glistened with a bead of sweat as I watched his strong arms glide the net in the pool getting small leaves out of it. His strong chest flexed as he lifted the net out and slightly shook the net out. Jakes, legs were lean and muscular no doubt from running on the beach on the little bit of time off that he had. I could just imagine the size of his cock and feeling it fill all of my holes.

After Jake left I went to my bedroom where I have this beautiful canopy bed with silk sheer drapes around each pole. I slide my bikini bottoms off and slide my fingers inside my pussy and rub my clit with my other hand. I pinch my nipples a couple of times, until my back arches and I cum all over my fingers. Jake's birthday couldn't get here fast enough my pussy ached for his cock. I almost didn't want to share him with the other ladies, but I knew that having a bunch of beautiful women to jerk off would be one hell of a birthday present for any man.

The night before Jake's birthday I invite Giselle, Brandy, April, and Adaline to my place to discuss the plan and to decorate the pool area. Giselle was bringing her friend Cathy. Brandy was bringing Sierra, April invited her cousin Stephanie and Adaline brought her Sister Nikki. They were all in agreement with what we were going to do for Jake's 18th birthday.

We set up a Happy Birthday banner over two stands at the shallow and narrower end of the pool. We blow up some inflatable coasters and put a piece of cake on each one. We each blew up balloons and tied them sporadically around the pool and put candles around the deck of my swimming pool and I call Jake to come over. All the ladies Giselle, Cathy, Brandy, Sierra, April and her cousin Stephanie and Adaline and her cousin Nikki all took their tops off. They were all very beautiful women some with bit tits some small tits and perky nipples made me horny. But what I wanted was to feel jake's hard cock slapping in my hot wet aching pussy. As we hear Jake drive up we each grab a piece of cake and light the two candles in each piece and we start singing Happy birthday as he walks through the back yard gate to my pool area.

His expression was priceless. With deer in the headlight eyes, and being shy and bashful as ever seeing nine beautiful women topless singing happy birthday he walks up to us with his head down. His face must have been fifty different shades of red he walks up to us. I tell him to make a wish and to blow out his candles. We all huddle around him pieces of cake in between each of our tits and he blows out all the candles in one big heavy blow. His breath blew on our nipples making them hard. Then each girl kissed him on the lips and told him Happy birthday.

"Jake, this isn't all your getting for your birthday". Each lady stripped out of there bikini bottoms and jumped in the pool and swam to an edge and got out and sat on the edge with there pussies each over the edge. I strip out of my bikini bottoms press my tits and nipples up against his strong chest and kiss his lips, then whisper in his ear that he gets to lick each woman till she cums. I grab his white t-shirt with both hands and rip it off of his body then went to my knees and stripped him out of his shorts. His cock was big, bigger than I thought. It was at least 8 inches as I took it in my mouth. I get up kiss his kips again and dive in the pool.

Jake swims over to Giselle and Cathy first. Cathy sits on top of Giselle's lap, Jake licks both of there pussies at the same time. While the rest of us watch and wait for our turns. Cathy and Giselle are soon moaning and fingering each other while jake licks there clits until they both cum in his mouth. I look over to my right to see April and her cousin Stephanie deep french kissing each other. To my left were Adaline and her sister Nikki sucking and licking each other's nipples made my pussy wet, I closed my eyes visualized what it would be like to be with each woman and I suddenly feel a hot wet tongue licking me. Jake had swum over to my edge of the pool and started licking my clit and it wasn't long and I was cumming in his mouth. He put his hands on the edge of the pool and lifted himself in front of me and kissed my lips. I feel the head of his cock barely touch my pussy lips. I tell him that when he's done that I have a special surprise for him later. He lowers himself back down into the pool and swims over to my right to April and her cousin Stephanie.

Stephanie lays on her back pussy over the edge of the pool, April Lays down on top of her tits up against each other and start kissing each other while jake licks there pussies. Sometimes fingering one and licking the other and vice versa until they both cum on Jake's tongue. Giselle and Cathy are in a hot sixty-nine position make my pussy ache for some much-needed spanking by a hard cock. I get up and walk over to Giselle and Cathy and we get in a hot daisy chain action of licking each other's pussies while Jake finishes up and licks Brandy's and Sierra's pussy.

After we had all gotten our pussies licked and fingered by jake we all get out of my pool and down on our knees in front of him while he slowly jerks himself off on our tits and nipples. We each take a turn and lick his cock and suck his balls. We all get in close to each other as Jake shouts that he's cumming. We put our hands under our tits and he explodes his load all over our tits and nipples. After that, we each take a turn and suck his cock some more till he's hard again. We all wanted more, all of our pussies wanted to be banged by this hard eight-inch cock.

We take Jake to my bedroom and tie him down to my four pillar canopy bed. We each take turns jerking, licking and sucking his cock. I wanted to feel his cock first. I straddle his cock as it slides up into my pussy. "Oh my God," I shout. I slowly at first start sliding my pussy down on his cock, Giselle sits on his face. While riding his cock, Cathy stands in front of me letting me lick and suck her pussy. Brandy stands in front of Giselle for her to lick her pussy. It was the hottest Bi-sexual lesbian orgy that I had been in. I gyrate my hips back and forth a bit more till I explode my hot juices down on Jake's cock. Cathy then takes her turn sliding her hot petite body down on Jake's cock and almost immediately cums.

Brandy, Giselle, April, Adaline and her sister Nikki, Sierra, and Stephanie each take there turns fucking and riding Jake's cock till they each explode their hot pussy juices all over Jake's cock. We each take turns licking and sucking him off some more until he says that he's going to cum again. We untie him just in time as he shoots his load in each of our mouths. It was the hottest bisexual lesbian orgy that I ever had and the best birthday present that turned a pool boy into my cabana man.

After that every week, I let jake have his way with me pounding his hard dick inside of me for payment for cleaning my pool. I don't think that there is a piece of my furniture that we haven't done it on. Once a year we all get together and have a similar birthday party for everyone, where there's plenty of tits and pussy all sharing a big hard cock and hot juicy loads squirted into hot wet mouth-watering mouths.

Victoria Cumming

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About the Creator

Casey Keller

Hi, I'm a 47 year-old-veteran/photographer/door dash driver/uber driver as well. When I am not doing any of those things I can be found sitting in front of my computer writing books for amazon/vocal. keep your mind busy the body stays young

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