Courtney: The Golf Cart Girl Ch. 01

May 31, 2024 // By:analsex // No Comment

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Courtney Connors was one of those girls everyone called hot. Red hot.

Courtney had been every guy’s dream girl in high school back in the late 80s, but I got to know her at the Stone Harbor Golf Club where I worked as a cart attendant and she as a cart girl.

For those who aren’t golfers, the cart girl is a sort of waitress on wheels. She drives a golf cart stocked with beverages, snacks and so forth around the golf course. These women are generally young and good looking, quick with a quip and a smile because it led to tips.

At this New Jersey club it meant a hundred bucks a day if the weather was good and play way high. .Like most experienced cart girls (there must be a manual somewhere) Courtney always had a big smile, wore tight white shorts and a club golf shirt. Prim and proper to one degree, oozing sexiness to another.

Courtney had little time for me, choosing to cavort with sports studs, but whenever she needed some help around the club I would pitch in, if only to get a close look at the 18-year-old blonde cheerleader.

“Hey Rob, can you help me with this box?” asked the 5-4, blue-eyed girl.

Boy can I help with your box, I thought, but merely replied “sure”.

I loaded the box into her cart, staring at her shapely tanned legs as she slipped in to the driver’s seat an drove away.

God she was hot.

On the infrequent occasions we got a chance to talk — usually when she was stocking the cart — Courtney mentioned she had received a partial scholarship to Villanova, but unless finances improved she might start college at a local community college.

I joked she could go to Rowan University with me…maybe even share a dorm room, causing her to laugh out loud and mutter “In your dreams.”

She was out of my league, so I was thrilled just to infrequently talk and of course soak in her good looks whenever I could.

Midway through the summer Courtney was talking about Philadelphia and I mentioned college, and she informed me that she definitely would be attending school on the Main Line. She told of her parents finally agreeing to a school loan, and she said her earnings over the summer would make up the difference needed to attend the prestigious school.

I didn’t think about it at first, but one night after giving her a hard-pounding fuck in my masterbatory bed I somehow got to wondering how she had gone from someone with little chance of getting the money for the college of her choice to a slam dunk entry. The partial scholarship and the small student loan didn’t add up to the large amount required to attend, but I guess the tips were good when you were a beautiful female batting your eyelashes and wiggling your behind at men all day.

The events of late July enlightened my thinking.

It was a hot, sticky Jersey Shore day, complete with a 4 p.m. thundershower which sent most of the members scurrying to shelters on the course or into the clubhouse. Courtney drove into the cart barn then headed toward the restaurant with her cash box, and I remember thinking that maybe she was skimming money off the top to add to her tips. Nah.

The rain was torrential at times, and the barn got hotter and stickier my the minute, so when it began to let up I decided to head out to my car for a new shirt. Rather than walk around to the lot, which involved heading around a long pathway then behind the maintenance shed, I sort of trekked up a sandy mound and through some evergreens and to my car.

Opening the trunk, I pulled out a new club shirt then glanced around the lot. Seeing nobody, I slipped off my wet shirt. Just then I heard a car approaching, and realizing I could get into some trouble for changing in the lot I quickly grabbed my new shirt, shut the trunk, then scampered up the closest hill into the trees before being spotted.

Out of breath, I paused at the top of the hill in the evergreens and tidied up my shirt before heading back to the cart barn. Something, however, told me to see who was driving into the lot, and I glanced out of my secluded location only to eye the black Mercedes of Mr. Gamble, a local realtor. Nothing surprising there, although I did wonder why he was driving in to the back lot normally reserved for employees.

What startled me more was that Courtney was in the passenger seat. Pretty, sexy, untouchable Courtney.

My inquisitive mind got the best of me, and I sat out of sight as the twosome parked in the rear of the lot, well away from spying eyes but not mine. The two talked for a couple minutes, and I noticed Courtney laughing at one of Mr. Gamble’s corny jokes. At least that’s what I surmised, because he was known around the club for two things, his lousy tips and his bad jokes.

I knew I needed to get back to my job, but I couldn’t get myself to leave. I had to know what was up. It wasn’t long before I knew.

Mr. Gamble began looking around and I noticed him sort of adjusting his midsection, shuffling in the driver’s seat. It all happened so fast that nothing dawned on me until seconds later when Courtney, miss prim and proper Courtney, miss I don’t have time for mere görükle escort mortals Courtney lowered her head into Mr. Gamble’s lap.

It struck me like a ton of bricks. Courtney Connors was sucking cock. Mr. Gamble’s to be precise.

Now from my vantage point I couldn’t be sure. I mean, I didn’t see his cock and to be honest I could only see the top of her head. But that head was bobbing up and down on something in his large lap. It didn’t take a map for me to get the picture.

I attempted to slip a little in the shadows to get a better look, but it was impossible to do without moving into a location where I might be observed by the lovemaking twosome. So I resigned myself to see what I could from my secure spot. I remember thinking that it was odd that this middle aged, married man with a paunch was able to attract this blonde beauty, but those thoughts were quickly dispelled as I was drawn to the naughty couple.

Never before had I been a voyeur, but I have to tell you, even not seeing everything it was the hottest thing I had ever seen. Hotter than when I stumbled across my dad’s porno collection. The actors into raw sex, but the vision of Courtney going down on Mr. G. was way more exciting to my eyes.

Mr. Gamble’s head was well back against the headrest, and I could tell his body was rocking up and down. The top of the blonde mane of my favorite cart girl slipped in and out of view, first slowly, then a little faster, then speeding up as the two rocked together. Suddenly Mr. Gamble stopped mid-bounce, and his hands encircled Courtney’s head.

Uh huh, he was cumming. He had to be cumming. And from the way he was holding the girl’s head, he was cumming in the mouth of the girl with the light red lipstick.

They held that pose for several seconds, and I noticed his hands moving off her now slowly bobbing again head. She stayed down there for about a minute, barely moving, as the man laid back in luxury. Soon Courtney pushed up and moved back to her side of the car, saying something to the man before reaching into her purse to grab her lipstick.

My hard-on nearly exploded, not from watching the blow job, but from watching Courtney reapply her lipstick.

I slid back, slithering out of my hiding spot, and ran back to the cart barn. It wasn’t easy, because my cock was rock hard all the way, but I pushed it down into my underwear to be decent. Luckily, nobody complained about my absence and I quickly began drying and moving carts and clubs out of the shack in anticipation of the return of the members.

Several went back out to the course, and in my devotion to work I nearly missed Courtney’s reappearance. When I spied her she was already in her cart, attempting to drive out but slowed by several carts blocking her way. I had trouble looking at her, knowing what she had just done minutes before, but first got one, then another, cart out of the way.

“Thanks, Jon,” said the girl.

“No problem, Courtney. Any time! We’re here to help, you know, that’s the cart attendant’s credo,” I stammered, awed at how the girl could be so composed just minutes after sucking the cock of a club member twice her age.

Courtney looked at me as if I was from Pluto, but smiled.

“Uh, Courtney, I don’t want to get too personal, but, uh, your lipstick is a little smeared.”

I couldn’t believe the words came out of my mouth. The girl looked at me in shock.

“Got ya,” I said with a laugh. “You are just always looking perfect, I was kidding you.”

Relieved, she laughingly called me a jerk, shook her head then sped out onto the course.

From that day forward I did all I could to observe the young girl. I’d look at the tee sheets to see if Mr. Gamble was scheduled to play, but on the couple of occasions he was there didn’t seem to be any hanky panky going on with Courtney. I just couldn’t figure it out.

Courtney was the nightly featured attraction as I whacked off to the vision of her sucking off Mr. Gamble. Sometimes, right before cumming, I’d have her look up and motion me over to blow the two of us. As they say, the mind is a terrible thing to waste…so I used it to imagine ways of using the young girl as my sex toy.

It was difficult working with her daily, because I knew of her parking lot dalliances. I was jealous of Mr. Gamble, wondering what she could possibly see in that older guy when eager guys like me worshiped her every wiggle.

Yet the reality was she had no time for me, and apparently had time for Mr. Gamble. I had nearly resigned myself to my chance observation of the two lovers being a one-shot deal, but something in the back of my head said time was on my side and I would catch some more voyeuristic action.

Turns out I was sort of right. Let me explain.

It was a warm Tuesday evening, just after 8. I was the only attendant remaining, with my sole responsibility to clean the carts as they came in and orderly drive them into the cart barn. Once taken care of I’d lock up and be on my way. There were about five or six groups left on the course.

Courtney had been hanging bursa escort bayan around the women’s locker room and parking lot. It was as if she finished work, left for the day, but got to her car and realized she had forgotten something. I’d see her walk back to the clubhouse a couple times, heading into the employee’s entrance. Later I saw her go out toward the parking lot, only to come back in. Once I saw her standing near the club, looking out at the golf course.

It was confusing to me, because it appeared she was looking for someone, but I knew Mr. Gamble wasn’t on the premises so it wasn’t as if those two might be hooking up (and I might get to watch!). Still, it was odd.

Douglas Mack’s group was coming up 18 and I looked to see if possibly Mr. Gamble had evaded me to play with his business partner. Nope. It was just the businessman and three men I didn’t know. Guests of the man, most likely.

They completed their round and drove up. I cleaned their clubs and Mr. Mack tipped me a $10 bill. “It’s a good day, Jonathan, the boys here donated to my favorite charity….me!” said the man, nodding at his playing partners. The men headed inside while I racked their clubs and then took care of the cart. I had a funny feeling, a guess really, that Courtney had not left. I took a quick walk toward the back parking lot where I stumbled upon Courtney sitting in the front seat of her car, her radio playing softly. Hers was the only car in the lot except mine, but they were well apart. Unlike the prior week, this time she was much closer to my vantage point.

I was intrgued, but knew I had to get back to the job to avoid suspicion. I knew she was up to something, but what?

Quickly taking care of the next two foursomes who finished their round, I again scampered back to my vantage point. Courtney remained in her car, listening to music. Slipping back toward the clubhouse I waved at several members as they left the club, then watched a father and son practicing on the putting green.

That’s when it dawned on me. Courtney was waiting for Mr. Gamble in “their” favorite spot! Of course, the parking lot was relatively safe from the prying eyes of members, a good place for the two lovebirds to meet late in the day. Mr. Gamble wouldn’t worry about his wife driving up, the club was nearly deserted, in other words, perfect!

Courtney, I surmised, was merely early, waiting for her older lover. I got an instant hard-on imagining what I soon might see. Would she blow him? Or could it be possible she’d fuck the geezer?

I was a whirlwind cleaning up the barn, so much so that I passed on attempting to get tips when one of the groups came in, busying myself with parking the carts.

The cart barn had a seldom used back door, but I used it that night to sped my trek toward my hiding place among the evergreens. At first I thought I was wrong, because only Courtney was in the secluded locale. I nearly started back to the job when I stopped mid-step upon hearing an approaching automobile.

Bingo. It was a black Mercedes.

Upon further inspection, it wasn’t Mr. Gamble. No, it was Mr. Mack, and be pulled alongside Courtney’s red Civic. Courtney smiled, waved, and exited her car only to enter the luxurious leather passenger side seat. What the heck was going on here?

They must be discussing a gift or something for her lover. Why not? Mr. Mack was Mr. Gamble’s closest friend and co-manager of the real estate office. At least that’s what I was thinking until Mr. Mack reached down and unbuckled his belt and slipped his wiener out of his pants.

Courtney moved closer to the man and slid her hand onto his dick while planting a kiss onto his lips. The two made out for a couple minutes, with Courtney slipping her talented hand up and down his cock. I knew this because from his car was no more than 20 feet from my viewing area.

They broke their embrace and talked for a minute … to softly for me to hear, but all the while sweet Courtney was stroking the man’s good-sized dick. Mr. Mack said something and the girl of my dreams smiled, looking down at his manhood.

The scene was priceless. Courtney licked her 18-year-old talented lips, smiled at the man, then dropped her head into his lap.

Geez, what was wrong with me? Where was my camera?

Note to file, don’t forget it next time!

I reached into my pants and slipped out my cock, stroking it at the same speed Courtney was working Mr. Mack’s meat. Unlike Mr. Gamble, whose head was well back into the headrest, Mr. Mack was still, content to let the girl work her mouth magic while observing each and every movement of her pretty face on his cock.

She ran her tongue around the tip of his cock, then swabbed it all over with hot wet tongue action. She kissed the side of his dick, then moved her head and kissed the hard spike some more. She looked up at the man, continuing to stroke with her hand, and I could swear she asked him if she could suck his cock.

He nodded, and she lowered her head once more, this time rubbing the dick against her lily white face. First she held bursa escort the dick against her skin and then she stroked it against her soft cheeks, kissing the base of his cock whenever she got all the way down against the junction of dick and balls.

Then she lifted her head and looked at the dick as the man pulled down his pants and underwear to give her complete access. She ovaled her mouth and slowly inserted the cock between her lips. Inch by inch she sucked it into her wet, willing orifice. This time the man’s head fell back in the luxurious pleasure of her talented teenaged mouth.

I couldn’t believe how talented the young girl was at giving head, not that I had much experience at receiving such attention. Fact is, I was still a virgin, having only gotten a hand job from a girl. But I had seen several erotic films and while I knew they might not depict “real” girls I knew Courtney was every bit as sensual.

Courtney took one, two, three and four inches into her mouth, stopping to savor the cock before moving into a tantalizingly slow upstroke. She then repeated the act, maintaining her slow speed as the man moaned his admiration.

My mind marveled at the experienced mouth of the girl. She was stroking the base of Mr. Mack’s slab while moving her mouth in tandem. It wasn’t long before she began moving a little more quickly, bringing the man closer and closer toward release.

The girl deliberately wormed the flesh in and out of her mouth as the man began quickly lifting his midsection off the plush leather seats. Mr. Mack put his hand on Courtney’s head and guided the speed for several strokes. Then he moved his other hand on top of the girl’s, stroking along with her.

Suddenly he pulled the cock out of her mouth, but the two continued stroking. Unbelievably he began shooting his sticky sperm all over the cheeks of the girl of my dreams. First one spurt, then two, three and four shots of man juice made its way to Courtney’s innocent face.

It was so erotic watching the cum shooting all over her face. Watching a blow job was amazing, but observing the man jerking his cock and exploding his sauce on her face brought the cum spurting out of my own cock.

Mr. Mack rubbed his dick over Courtney’s face, spreading the sticky residue of his orgasm like a painter would a wall. Even after his orgasm subsided he rocked in his seat. Courtney continued her affair with the man’s dick, sucking it back into her mouth. I watched scooped some of his come into her mouth, then looked at the man while deliberately swallowing the cum.

She cleaned his cock then sat back as the man pulled up his underwear and pants, buckling his belt. All the while he was stroking her cum-stained cheek, rubbing the sauce into her creamy face like moisturizing lotion.

The two talked a bit, then Courtney made her exit and returned to the Civic. With a wave she backed out and drove out of the lot.

I couldn’t believe she was seeing both men, guys who work together at that. It was hot to think about, but I surely didn’t understand what was going on. A week later I was startled to the nth degree when Mr. Gamble and Mr. Mack were playing a match with two local building contractors.

The heavyset man was named Norville, the other, slimmer guy John. It wouldn’t have been important until later that day, however. I spent the day wondering if either of the real estate guys would be visiting Courtney that day.

As luck would have it I was at the equipment barn when the foursome finished their round, but I did note Mr. Gamble and Mr. Mack in deep discussion with Courtney near the rear of the clubhouse later that evening. She was shaking her head “no” but the two were insistent. I figured her jig was up, that one of the men found out about the other and were in the midst of a confrontation.

Wow wrong I was, because soon all three were laughing. Go figure. The men went back into the clubhouse while Courtney drove her cart to the barn.

“Can you do me a big favor, Jon? Can you take care of my cart? I have to get to an appointment,” cooed the girl.

“Sure, Courtney, I’ll handle it. Got a big date?”

“Nah, just have to take care of some things,” said the girl.

“That’s great, Courtney!”

The girl kissed me on the cheek before whirling away and rushing down the path toward the back lot.

I knew she said she was leaving, but I had to be sure. I grabbed my camera and slipped out to my favorite voyeur spot and saw the girl slip into her car. She didn’t start it, though, preferring to apply some makeup.

Soon an SUV drove into the lot and pulled in next to Courtney. I couldn’t believe my eyes: the two guys from the real estate guys foursome were inside, and it hit me like a ton of bricks. Courtney was a whore.

This time the guys and Courtney got into the back seat, the girl in between the two horny men. My view was nowhere near as good as my earlier spying sessions, but there was no doubt at her task. The men wiggled out of their pants, and Courtney took turns satisfying their sexual needs. It didn’t take the girl long to complete her task, and I was a bit disappointed in that she didn’t take as much time or make as much effort with the two guys. Each left with a smile on their face, as did Courtney. I didn’t see any money exchange hands, so I figured my whore thoughts might have been incorrect, but who knows?

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