The Best Summer Job Ever

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A young man gets the best summer job ever.
7.7k words
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Part 1 of the 3 part series

Updated 06/09/2023
Created 07/27/2018
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(This is both parts combined for the "Summer Lovin Contest)

*

One summer, I had the best job a young man can have, I was a bartender at a a resort in the tropics that my Uncle Mike owns. Uncle Mike couldn't pick me out of a police lineup, and his kids run the place, but family is family. They were at least eight years older than me, and we had never been close. I was 19, after my first year of college, and getting desperate about what I would do in the summer, when my father said, "Why don't you go work for Uncle Mike?"

Dad made the call, I got a passport, bought some sunscreen, packed my bags, and there I was, being introduced by my cousin, Michael Hammond, Jr. to Bertrand, the manager of the resort's dining areas. The place was sprawling, with several pools with floating bars and dining options ranging from formal to casual. I trained with Alfonse, the head bartender for the first week, I was given a radio and sent off to man one of the many bars on the property.

It was early in the season when a hurricane was forecast to come ripping through our resort, and we all began to prep feverishly for the upcoming disaster, but at the last minute, the hurricane veered off, out to sea. So we went about unpacking and getting back to normal, but nearly every guest had canceled.

The resort was still fully staffed and it felt like we employees outnumbered the guests. I was sent to man station thirteen, a small poolside bar on the ass end of the property. It was up over a small hill and down some stairs, and while you could walk to a beach from it, it wasn't the most convenient or famous beach. I set up, applied my sunscreen, and went to work reviewing the weird tropical cocktails that I was expected to make.

I was slowly getting bored out of my mind when a trio of men arrived, my first customers of the day. They ordered beers, realized this bar was not where it was going on and left. I put up the 'Be Right Back" sign, locked the register, and went off to answer nature's call.

When I got back, there they were two stunning young women sitting at my bar. With the bright sun reflecting off the pool into my eyes, they were like a mirage or hallucination. One was tall and thin, with soft blue eyes, modest breasts, and nipples that were poking her bikini top, the other was short, and busty, with brown eyes, dark brown hair and a mischievous smirk . And immediately they started flirting with me and giving me a hard time, "Is this place open?" "Are you even old enough to drink?" "Are you a real bartender?" and asking if I knew what was in 'The HammondCane' . After a couple of drinks, I learned that they had come to the resort with their boyfriends, who were attending a small conference on mortgaged securities that hadn't canceled (bankers being cheap) and they were pissed off at being ignored. Also, the SCUBA instructor, McGillis had buggered off ahead of the projected storm and wouldn't be around.

A few customers came by, stopping for a drinks before heading down to the beach, and the girls decided to take their drinks to the chaise lounges at the other side of the pool, which were finally getting some sun.

"Hold it there, you two have to settle up!" Now it was my turn to give them a hard time. They looked startled. They had both run out of their rooms without their keycards, the cards the we use to bill things to their rooms." One of you could stay here, while the other goes back to her room"

"But that's a long walk!"

"Well, if you two show me your boobs, I'll let you drink for free," I said. I braced myself, half-expecting to get both of those drinks thrown in my face.

But they turned aside, put their heads together and whispered. Gina, the taller one seemed unhappy about it, but Mindy, the shorter, bustier of the two seemed think it would be good payback to their boyfriends, who only seemed interested in showing them off and banking.

"We'll do it!" I tried to hide my shock and delight, as I looked around to make sure there weren't any other employees around. Being a Hammond wouldn't save me from this. "OK, here are the rules: Every time you want a drink, you have to lift up your tops and count to three. Not real fast, but for three full seconds. Got it?" They nodded.

They looked around for a moment, then looked at each other. Mindy went right ahead, and Gina was a moment behind. "Onetwothree!"

"Very nice, girls, but that was not three seconds. Let's try that again"

"One...two...three!"

I examined their boobs. Mindy's were larger and fuller, and Gina's had long nipples that were just starting to perk up when she pulled her top down over them.

"So, what'll you have?"

"Margaritas!"

I made them margaritas, and they headed off to catch some sun.

A little while later, the two of them came back, and said, "Two margaritas, top shelf!"

"Whoa! Top shelf? You know that will cost extra."

They looked confused. "Ok, here's what you'll do. Gina, you'll stand behind Mindy and count to three while pulling up her top. Then you'll switch. This time they didn't grumble or discuss, they just did what they were told.

Gina took her position, pulled up Mindy's top and counted, "One..two.."

"Gina, you know, you have really beautiful eyes"

"Aw, thank you, I get them from m-"

"Gee-NA!" Mindy shouted, and pulled her top down. I think Mindy was annoyed I wasn't gawking at her boobs.

Mindy's turn came, and she extracted some payback, counting very slowly, and when she was done, she gave Gina's stiff nipples a tweak, prompting much giggling.

The girls took their drinks, and walked unsteadily back to their lounge chairs. A little while later, Mindy came up to the bar alone, "Two margritas, top shelf!" Her face was flush.

"What are you willing to pay?" The little game we are playing was getting serious.

She pushed through the beaded entrance to the bar, leaned against the wall and lifted her top. I reached out and caressed the sides of her breasts, lightly with my fingertips, tracing the outlines of her soft curves. She sighed and bit her lip as I slowly worked my way up to her stiff nipples.

I said, "Do you really want to do this?" She answered by reaching out to massage my hardening cock through my pants.

I put together a quick plan. I opened the sheltered outdoor storage area right behind the bar, which had been cleaned out in the hurricane preparations. I locked up the register and put up the "Be Right Back" sign. Then I went back to Mindy, and closed the door behind me.

The storage area was about four feet wide and the length of the bar. It had a curb and a little wall, followed by a steel bar fence, and it overlooked our parking lot with the ocean in the distance. I held her from behind, covering her neck with kisses, massaging her right breast, and working my other hand under her bikini bottom.

She moaned loudly as my fingers diddled her clit, and I whispered, "Shh!" in her ear. Neither of us wanted to be caught.

I maneuvered her up onto the curb and pulled her bikini bottoms to the floor. I pushed her legs apart and gave her a gentle nudge forward. Now I dropped my pants and underwear, and eased my cock into her.

Mindy greeted this with a low grunt, as I edged forward and pulled back just a bit. She was wet, but tight. I pushed again and retreated, and she gave a moan. She leaned forward, grabbed the bars and her tits began to dangle and wobble back and forth, as I pushed back and forth, until finally I was all the way in. I began to fuck her hard and fast.

Her low grunts began to build, getting higher and higher pitched, until she came, crying out aloud, a cry that echoed through the parking lot below.

Mindy had cum, but I was still hard and ready. She turned around and kissed me as she caressed my dampened cock with her hands. Then, kneeling, gave it a long, slow lick, starting at the tip and ending at my balls. This had me moaning, and she licked back up towards the tip and took it in her mouth. As she licked and sucked my cock, she gently caressed my balls with her finger tips, and I was approaching the point of no return when-"SECTION THIRTEEN COME IN!!" My radio goes off, startling us both.

I grab my radio and responded, as I pull up my pants. Alphonse was closing my section and wanted me to help out the bartenders working the dinner rush. Mindy skittered off, but in cleaning up, I spot an upside down coaster, with "9:15 rm 237" on it. I smiled, and I'd swear my hard on lasted through the dinner rush.

I knew that "9:15" meant 9:15AM, not PM, I figured that the conference Mindy's boyfriend was attending would start at 9, and the coast would be clear. At the stroke of 9:15, there I was, knocking on the door of room 237.

But who answers the door, but Gina, wearing her panties and thin, white t-shirt. My jaw dropped, she looked amazing, for someone who had obviously just woken up, her soft blue eyes, disheveled blond hair, and nearly see-through shirt were irresistible. She grabbed my hand and pulled me close. I turned and kissed her, and we began to make out.

I worked my hand under her shirt, turned her slightly, and reached up to caress her breast, when, in from the adjacent room walked Mindy, "My, my what have we here?"

I was startled, but Gina took it in stride, "Why should you get all the fun?"

Relieved that this wasn't going to turn into a cat-fight, I decided to modify the plan I had for the day.

"Get your suits, girls, we're going on a road trip!"

"Whaaaat? But it's our last day here!"

"This is the first day off I've had in weeks, and I'm certainly not going to spend it here. You two complain there's nothing to see or do here, so we are going off the beaten path. Bring some lotion and towels, too. I've packed some food." I hadn't planned on taking Gina along, but sometimes you have to improvise.

We got to my car, which was, like most cars on the island, vintage, piled in, and headed out onto the highway. Gina read the directions and stretched out her long legs in the back seat, while Mindy road shotgun and sung along to whatever came on the radio, whether she knew the words or not.

After passing through what seemed like an infinite stretch of sugar cane fields, we got off the highway and headed through a small town, then down a long dirt road. Finally, we pulled into a small, makeshift parking lot that had a handful of cars in it.

I grabbed a small cooler from the trunk, the girls grabbed their bags and we headed over a small dune to the beach.

"Here we are, the finest beach on the island!"

And it was gorgeous, like a living postcard! It had everything: the soft white sand, the crystal blue water, the gentle breeze bringing the scent of tropical flowers down from the hills. Only a few big fluffy clouds hovered over the mountains in the distance behind us. I quickly got out my phone to take a picture, this little bit of heaven was going to sustain me through many an endless arctic winter back home. I was trying to take a panorama shot, when a strange, bronzed man came running up to me.

"No picture! No picture!!"

He startled me twice, once when I was concentrating on taking the picture, the second time when I looked down and realized he wasn't wearing a bathing suit.

Upon further inspection, nobody on this beach was wearing a stitch of clothing, but they were all scattered about so wasn't immediately obvious. I had asked the concierge, Jorge, where the best beach on the island was, and this was obviously a prank. Vowing revenge, I did the only thing I could do, I dropped my bathing suit.

The girls looked at me in shock. "Well, do you know any of these people?" I gestured towards the sparse crowd. "The picture police are here, we won't end up on the internet, so what the hell!" I got out my suntan lotion and began applying. Shrugging, Mindy and Gina, untied their tops and slid out of their bottoms.

Putting on suntan lotion always takes me back to the lakeside vacations I took as a kid. I still remember my mom reminding me to cover my ears and the tops of my feet. I'm pretty sure she never told me to make sure I cover my cock and balls, but I think I'd remember a family trip to a nude beach.

I gave my crotch area a quick spray, as it is the very last place you want to get sunburn, but I didn't want to 'wake the beast,' if you know what I mean. That was going to be hard, as Mindy was putting on a show, oh-so-slowly rubbing the lotion into her breasts. Gina was also taking in this show, and I turned to her and asked her to do my back, while I lay on my stomach.

When Mindy saw this, she said, "Oooh, can I help?" and thus, "the beast" was woken, as Mindy dangled her tits in front of me while doing my upper back, as Gina rubbed lotion into my thighs and ass. I was enjoying the attention and wondering how long it would take my boner to subside, when Gina shouted, "Last one in is a rotten egg!" and the three of us sprinted off towards the water.

After frolicking in the surf for a spell, we returned to our towels, dried off and ate the sandwiches I'd packed in the cooler. Over lunch we got to talking. Gina and Mindy were childhood friends and roommates, Mindy was an actress/waitress, and Gina was a dental hygienist. They'd been seeing their boyfriends for about a month and a half, and they were not happy.

"They really love money more than either of us," Gina complained.

"Yeah! And they made us pay for this trip, while bragging about the fat year-end bonuses they get,"

Mindy said, "and show us off at office parties where we get ogled by creepy old men."

"Since when do you mind being ogled, Mindy?" Gina jabbed. Mindy hissed and made a cat's claw at her, as both girls laughed.

"But what about you, Johnny? How did a very white guy like you end up out here?" Mindy asked.

I told them how my girlfriend dumped me at the end of the last semester, screwing up my plan to work at her dad's restaurant for the summer. I did my 'narrator voice' "But fate had other plans for John Hammond."

Gina interrupted, "Wait a minute, you're a Hammond?!"

I had to explain that my family weren't the rich Hammonds, that my father worked in a bank, and my mother taught English at a private high school, and that when Michael Hammond, Sr. died, I'd be lucky to inherit a case of those cheap plastic "Hammondcane" cups.

With that, I lay back, closed my eyes and took a nap in the sun.

I wasn't out for long, when I felt a gentle female hand rustle under the towel I had thrown over my crotch. Gina's hand found my stiffening cock, "You were right, Mindy, I think his cock is bigger than Bradford's"

"Go for it, Gee, it seems like the crowd has left"

That was weird, the crowd had left? And it seemed like the sun had gone in, so why not lay back and enjoy a nice, slow hand-job? Then I felt a few drops, then I heard thunder, then I saw a bolt of lightning even though my eyes were closed. A storm had moved up quickly from behind us.

The hand-job was a fond memory, as we all scrambled to collect our stuff and head for the car through the pouring rain. Wet, shivering and naked, we made it to the car, and squeezed into the back seat. The windows steamed up as we tried to dry ourselves.

I was looking at Mindy, who looked me in the eyes and said, "While we're stuck here waiting for the storm to pass, I'm going to take care of some unfinished business from yesterday." And with that, she leaned down to plant a kiss on the tip of my cock.

Gina slid closer to me, as Mindy stretched out to lay across our laps. Sex in a car can be challenging for two people, let alone three, but this old car was just spacious enough. Mindy pushed my ass to the edge of the seat, so she could lick my balls, driving me nuts. Gina showed me her fingers, just as she plunged two of them into Mindy's pussy, making her moan. Mindy had licked her way back to the tip of my cock and was licking and sucking with gusto, and it was my turn to moan.

"How is she? Isn't Mindy a great cocksucker?" Gina asked.

I was startled and looked at her blankly. She gave me a wink. A little light-bulb went off in my head.

"Oh yeah! She really knows how to suck! She's going to take my massive cock and suck out all my cum like the good cocksucker she is! Take it all, you cock sucking slut!"

Gina shot me a "What the fuck dude?!" look and I took the hint and focused on my sincere praise of her skills.

Mindy was almost too effective, but as I was building towards a massive eruption, she began emitting the same grunts she had yesterday, Gina's fingering was having the desired effect.

She had settled on licking and sucking the tip of my cock, as her moans built, only taking her lips off as she climaxed with a loud, "Mmmmaaaah!" There was no need to quiet down this time.

Hearing her cum and seeing her blissed-out expression triggered my own eruption and I shot two blasts of cum at her face before she clamped her lips down and sucked the rest down.

As we slid back into normal sitting positions, Gina said, "Look at you!" and got out her phone to show her. There was cum in Mindy's hair and some on her cheek, and she laughed as she took a selfie, "This is one vacation photo I'm not sharing with grandma!"

The rain had stopped, and we got dressed and I began to drive us back. Gina was handling the directions again, from the back seat, but she was wearing a see-through mesh shirt, with no bikini underneath. This made me check her out in the rear-view mirror, and I could see her nipples poking through the mesh.

As we got closer to the resort, I made a turn into a small town and pulled over. "We're going to stop at my place, we can get showered and cleaned up before we head back." I had rented a furnished apartment above a small restaurant. I could have stayed at the resort, but I wanted to get away from that place just a bit.

As we entered my apartment, the girls simultaneously screamed, "I call first shower!!" and the two of them disappeared into my bathroom. For the next twenty minutes, I was treated to the sounds of a loud lesbian orgy going on behind my bathroom door.

Finally, the door opened, the girls appeared, giggling. Mindy was wearing a t-shirt and her bikini bottom and Gina wore just her mesh shirt and a short black leather mini-skirt.

"Oh? Did I miss anything?" I pulled my earbuds out and acted as if I had heard nothing.

"Aw, Johnny we were just teasing you!" Gina said, "When our boyfriends get drunk they are always like 'you two are bi, why don't you fuck for us?' It's so annoying!"

"Well, here at Casa Hammond, nobody is nagging anyone for anything. Our aim is to please."

"Is that so?" Gina said, "because there's someone here who could use some pleasing," and with that, Gina gave me a gentle shove into my couch. I sat down, she grabbed Mindy by the hand, and the two of them stood in front of me. Gina took a moment to tap her phone, and slow music, began to play from it.

Gina circled behind Mindy and slid her hands under her t-shirt, and massaged Mindy's breasts. Mindy smiled, and Gina grabbed the sides of her shirt and slowly tried to pull it up. She stopped and tried again, causing the shirt to tighten around the outline of her breasts. She tried one last time and Mindy's breasts bounced free, why Mindy pouted and feigned shock.

Now Mindy was just wearing her bikini bottoms. Gina pulled up a chair and had Mindy fold her arms on the back of it. Mindy's breasts hung free, and as Gina caressed the sides of her breasts, her nipples stiffened. Gina produced two small nipple clamps, and made a show of holding them in front of Mindy's eyes, which grew wide at the sight of them.

As each clip snapped on her nipple, Mindy let out a little yelp, and she began to shift her legs back and forth. Gina pulled Mindy's legs back so that she was really leaning on the chair. Standing behind Mindy, she gave her ass a forceful slap, untied her bikini bottom, pushed her legs apart, and began to stroke her mound, slowly teasing her pussy lips.