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When my buddy Brett told me about this sweet summer gig and all the chicks I’d get to watch—and hopefully bang—he definitely wasn’t kidding. We’d picked up some work at a resort in Playa del Carmen, but where he got stuck with a job as a busboy in one of the resort restaurants, I got the sweetest gig of them all. Cabana boy.

My job was to hang out on the beach, give towels to people, and ensure the area was neat and tidy. The cabana is my workstation, with buckets of towels and various other amenities that our guests might ask for close at hand, like suntan lotion and bottle of water. When it was slow—and it often was, since most folks already had what they needed and didn’t need to visit me—I got to just lay in the sun. And with my dark shades I got to do my favorite activity: watching chicks.

From sorority girls with barely-there bikinis and older ladies with quite a bit more coverage, this beach had it all. I was thankful, as always, that the swim shorts provided by the hotel that identify me as staff were a little baggy. Because I had a full-on chub watching all these fine women.

“I think you’re enjoying yourself a little too much,” said a slimy voice in my ear.

I jolted, startled by his voice. Marvin. My boss. The biggest cockblock I’ve ever met. “Just doing my job,” I said as I stood up from the lounger I had sat down in. I picked up some towels from the shelf in the cabana and started folding them, holding them in front of my bulging crotch.

Marvin had a bad combover and always looked…greasy. He sneered and looked to where I’d been looking, at the half dozen sorority girls splashing each other among the waves. He stepped close to me, his hot, oniony breath rolling over me in putrid waves. He reached between the towels and my body, wrapping his hand firmly around my hard dick.

“Fuck off, man,” I said, taking a step back and trying to shove him away, but this only made him tighten his grip on my cock.

“You keep this fucking thing in your shorts, Eli. If I find you getting this wet by dipping it in one of those sluts, not only will I have you packing and sent back to whatever shithole fraternity you come from, but I’ll have your balls in a jar.” He squeezed me painfully hard, making me yelp. “Understood?”

“Understood,” I said hurriedly.

Mercifully, he let go of my cock. I pressed the pile of towels I was holding against it, partly in an effort to make the hurt go away, but also partly to protect myself from him grabbing it again.

He sneered at me one more time and then stomped away to wherever it was that he hung out all day when he wasn’t harassing me. Likely some cave somewhere, given how much of a troll he was.

With him gone and out of sight—and unlikely to return anytime soon—I put the folded towels on the counter of my little station and sat back down in the lounger. Those sorority girls were still splashing each other, getting their tiny bikinis wet.

I clasped my hands together and laid them on my lap, over my bulge. Partly to hide it, but also partly to discreetly play with it. Those chicks got more aggressive as one of them leapt across the distance between them and tackled another, her face landing fully in the other chick’s tits as they both collapsed down into the water. I firmly pressed the heel of my palm into my hardening shaft as I imagined that first girl biting down on the second girl’s nipples.

And then she caught my eye.

With half the sorority sisters out of the way, I could see the banging MILF behind them, making her way to the shore. Every step she took revealed more of her amazing body as she ascended from the depths of the water.

First were her tits, full and round. The skin tone matched that of her face—lightly sun-kissed with a bit of a tan. Those tits, which had to be a solid 32DD, were perfect as far as I was concerned.

As she got closer, and as she rose more out of the water like some sort of marine goddess, I started to get a better sense of her age. Likely in her forties, maybe her fifties. If I had to guess, her kids had either just left home recently or they were finally old enough that she could leave them at home and go on vacation.

Her stomach was taut and toned. This was a MILF who took care of herself. And her bikini bottom was skimpy, just a narrow strip of fabric between her legs.

As I watched her, my thoughts went dirty. I couldn’t help but picture her here on this lounger as I slid that strip of fabric aside and buried my face between her legs. I’d eat her out until she was so fucking wet and desperate for me to stick my cock in her and fuck her senseless.

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It was my final day as a paperboy. Tomorrow I’d be packing up the car with Dad and driving to Minneapolis for college.

There were still a few accounts that paid cash or check monthly, rather than having it drawn out from their bank account or their credit card, so for those customers, I was doing my rounds and collecting fees—and also saying goodbye. I’d been their paperboy since I was thirteen, so now five years later at eighteen and about to move off for college, it was a big change, both for me and for them.

I saved my favorite client for the end. Mrs. Miller. She was a banging married MILF whose husband was always on long haul trucking jobs—and I guess as part of her way to keep herself occupied, she often flirted with me. We’d never done anything beyond flirt, though I would sink my dick into her at a moment’s notice if she ever felt like actually cheating on her husband.

More than once I’d gone straight home from chatting with Mrs. Miller to beat off into my cum sock. She’s fuelled many fantasies for me over the years.

As I walked up to her door, I tugged at the bottom of my T-shirt, straightening it, but also making sure it hung nicely over my pecs. I’d been working out the last several months and my body was starting to show for the effort.

At the top step, I rang the bell and waited. I didn’t hear the usual clamor of her teenage boys that had always been the backdrop noise to our little flirting game. A few moments later the door opened and Mrs. Miller smiled when she saw it was me.

“Good afternoon, Mrs. Miller,” I said.

“Good afternoon, Ryan. I told you to call me Linda,” she said, gently chastising me.

I smiled and I think I blushed a bit. “Sorry...good afternoon, Linda.” I fumbled with pulling my little receipt book out of my back pocket. “I’m here to collect your monthly dues.”

“Of course,” she said, holding the door open wide, “come in and I’ll go get my purse.”

With the door fully open, I finally got a good look at what Mrs. Miller—Linda—had on today. She always dressed super nice. Today she had a short black skirt and a black and gray shirt that seemed to wrap around her body and really accentuate her full breasts. And it was low-cut, giving me ample view of her cleavage.

I stepped past her to enter her house, and I tried to tame my boner when my shoulder brushed up against her tits. She made a satisfied little humming sound when I did that and I had to struggle to not read too much into it. This was just another case of harmless flirting that wasn’t going to go anywhere.

She closed the door behind me. “Wait right here,” she said, putting her hand on my shoulder before hurrying off down the hall. A few moments later, she came back down the hall with her purse in hand.

“Quiet today,” I said.

She put her purse on the little table just past the entryway and dug through it. “Yes, the boys went with my husband on his route. Sort of a last minute summer getaway before school starts up again next week.” She pulled her checkbook out of her purse. “Speaking of school, I hear this is the last time you’re coming by?”

I watched as she flipped open the checkbook and bent over to write out the check. Her ass, perfect and round, stuck out behind her. My eyes locked on it and wouldn’t let go.

“Yeah,” I said, managing to form full words and not drool. “Going to college in Minneapolis. I’ll be back for the holidays and next summer, but I won’t be your paperboy anymore, I guess.”

She tore off the check, stood upright, and turned around with a small pout on her face. “I’m happy for you, but I’m going to miss our little visits and chats.”

“Me too,” I said. 

She stepped closer, holding the check out, but then she stopped when her eyes landed on my chest. “Have you been working out?”

I grinned stupidly. “Yes, I have. I think it’s paying off.” I ran my hands down from my chest to my waist, smoothing out the shirt again.

She shook her head. “Can you...take off your shirt? I can’t really get a sense of anything through the shirt.”

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I held the football in the crook of my arm and just stood there, trying to give her my best smile. She walked around me, snapping pics from different angles and different heights. I noticed that she made sure not to capture the corner of the room in the any of the pics, the corner where my mirror hung on the wall, and Playboy centerfolds were posted all around it. In between pics, I side-eyed the mirror to ensure there weren’t any dried cum streaks on it. That was my masturbation corner.

“Huh,” she said as she flipped through the photos.

“What’s wrong?” I tried to crane my neck to see over the top of the camera, to se what was setting that unpleasant look on her face.

But then she looked up at me with a slight blush coloring her cheeks. “That shirt isn’t really making you look athletic. Um...would you mind taking it off?” She glanced away when she asked the question, like she was embarrassed or turned on. Hopefully it’s because she was turned on.

“No problem,” I said as I lifted my shirt over my head. I wanted to rip it right off, but I had to play it cool.
I think she thought I wasn’t looking her way, but I caught her eyeing my chest and her eyes flaring open. I think she also made a mmm sound.

But as soon as I tossed my shirt on top of the laundry basket and looked back her way, she was all professional again. I picked up the football again and she took some more pics. Eventually, she got down on her knees in front of me to take photos from that low vantage point.

“Perfect,” she murmured as she paused to look through a couple photos. She was still on the floor, sitting on her heels.

It didn’t escape my attention that her face was at the level of my dick. When she looked up at me, my now prominent bulge was in our direct line of sight. She didn’t notice it, or at least did a damn good job of ignoring it. I didn’t know if I should take that as a good sign or not; it at least didn’t make her uncomfortable. Maybe she was just a tease?

“One more pose,” she said as she stood up. As she got to her feet, her shoulder brushed along the length of my shaft in a way that I could only describe as being fully on purpose. She pointed at my bed. “Sit there, leaning against the wall.”

I did as ordered. My bed squeaked when I got on it, but quieted down as soon as I was seated and leaning my back against the wall. It was then that I realized I’d left the football on the floor and out of reach.

“Can you pass me that?” I asked, pointing to it.

“No need,” she said, stepping closer. She got down on her knees and rested her elbows on the bed and snapped a few pictures. She looked at the display and smiled. “Perfect.” She snapped a few more. “Would you, uh, be open to taking off your pants? I mean, you’re wearing underwear, right?”

“My-my pants?”

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“Geoffrey!”

I don’t have to look. I know that voice. Cassandra Miller, the office manager here. She is a banging hot MILF but intimidating as fuck. I always get both a boner and a shudder of fear every time we cross paths.

When I slowly turn to face her, I feel my dick grow hard and I struggle to suppress a shudder. Every damn time.

“Yes?” I squeak out. I clear my throat and try to deepen my voice. “Yes, Ms. Miller?”

She puts her hand on her hips, a position that makes the open neck of her button-up shirt stretch open just a little more, giving just a hint of the fullness of her cleavage. She’s absolutely gorgeous. Blonde hair cut just at her shoulders, smooth face, banging body, full boobs, and a hot hourglass figure.

I’ve jacked off many times while thinking about her.

“Come with me,” she says and turns on her heel, sashaying to her office door just around the corner from the reception desk. I watch her ass swing side to side in that tight black skirt of hers.

I try to look casual and hold the clipboard in front of my crotch and then hurry after her. When I round the corner to her office door, I find her waiting for me. I squeeze past her and she shuts her door. This is how some of my masturbatory fantasies have started — so it’s not helping me control my boner.

“Sit down,” she says in a tone of voice that clearly says don’t fuck with me, boy.

I obediently sit, secretly thankful for the momentary excuse to legitimately put the clipboard over my straining dick.

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The sound of the back door turns my attention back to the house. Mrs. Williams is walking toward me with a tray containing a pitcher of lemonade and two glasses.

“You’re looking a little hot, Tommy,” she says, with a warm smile. “Thought you might need a drink to cool you down.”

“Thanks, Mrs. Williams, I definitely do.” I lay the net down on the deck and join her at the poolside table. She places the tray down and pours lemonade into the glasses. When she hands me my glass, our fingers touch and I get a sudden jolt to my dick. It was a passing touch, harmless, but with where my mind is right now, it’s an incredible turn on.

I chug back half the glass, hoping the cold lemonade will cool the inferno of my building lust. Then I watch her take a dainty sip from her glass and then follow a bead of perspiration as it rolls down her neck and into the hollow of her cleavage.

She’s got a tight, white T-shirt on, with what looks like a floral bikini top beneath. Her outfit is finished off with cut-off jeans that ride high on her tanned thighs.

The lemonade is doing nothing to cool me down. My cock is at full attention, surely tenting my shorts if I would dare to look down.

Mrs. Williams quickly eyes me up and down and lets out a soft chuckle. My cheeks warm with a blush of embarrassment — I know she saw my boner tenting my shorts.

“Call me Sharon,” she says, as she puts her glass down on the tray. She takes a moment to stretch, thrusting her chest toward me. My eyes lock on her tits and my mind empties.

“Huh?”

She chuckles again and says, “You don’t need to call me Mrs. Williams. Sharon is nicer. It’s more … intimate.”

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