My folks recently moved to a large property in the hills outside of a major city. I thought it would be cool living in this urban setting not too far from the college I attended, but I soon found I needed to supplement both my time and pocketbook.
One of my classmates mentioned a nearby golf course was looking for a beer cart girl. Her friend had worked there while in school, and said it was easy making good tip money, so long as you knew how to “play the boys right."
“Tammy, most of them like cute/sexy," she said. “Chat ‘em up, laugh at their dumb jokes, but cut them off if they get out of line. And most of all, wear clothes that show off that tight little body of yours.”
The last comment felt vague to me. I was hardly one to have to fend off many boys through high school. I was slim yet strong, having run cross country and hurdles. My body had stopped growing at 5’1”, with a lithe 32A-22-33 figure, and I considered myself plain. It didn’t help that my dad was the weightlifting coach and put the fear of God into suitors. Since I had little experience around older men like the ones I’d encountered, she ran me through some scenarios to help me get the feel of it. It all seemed pretty simple, so I applied for it and got the job.
At first, it was okay. Sure, I would get bored hearing their dumb stories and comments, but the tips made up for it as I followed my classmate’s suggestions. After a while, I became more comfortable with role-playing and started buying cuter outfits while honing my skills at flirting with these guys. Truth be told, most were easy to manipulate, and I found pleasure in seeing just how much tip money I could extract from them.
As the next semester came around, my available days changed. I was disappointed to lose Ladies’ Wednesdays and hear all about the goings on, especially when it came to the salacious trysts among the members. These ladies knew all, and I began to understand the critical value of discretion. The rundown on who was sedate, who was fun and playful, and who was a Lothario helped me proactively manage my interactions with them while maximizing my income. They taught me some tricks as well, confiding in me that wimpy men would spend more on you just for the pleasure of your time and company.
“Greg West is known to dole out hundreds just to be near a woman,” Margie told me once. “That poor sap! He’s not bad looking, and with a little confidence and guidance could be getting laid.”
Rita chimed in, “what will your workdays be now?”
“Tuesdays, Fridays, and the weekends.”
“You’ll enjoy Tuesdays for sure,” she responded. There’s a foursome of eye candy that any woman would love to wrap themselves around. All four at once would be dee-licious! I wouldn’t be surprised if they’ve pulled that off more than once.”
“Who are they?”
“Phil, Steve, Ralph, and Gerry. We call them the surf brats. That’s how they met and became friends. But, beware, they’re well-seasoned. You’ll have to be in top form around them.” I was certainly interested in seeing what these four were about.
It wasn’t long before the surf brats and I crossed paths. As described, they were thirty-somethings that were athletic and fun. I confirmed that they swam and surfed together back in college, and, by the looks of their physiques, had kept it up, much to the pleasure of the women I would see swooning over them at the club.
I was especially interested in Gerry. He was about six feet tall, with that strong, tapered swimmer’s body that looked scintillating. I found myself looking forward to their company, even dressing special just for them, but Gerry’s eyes and voice cut through all that like he knew there was lust beginning the brew within me. And he’d be right. Those eyes both melted and moistened me in a way I’d never felt before.
On one particularly slow Tuesday, I drove through a sheltered part of the course and came across Gerry alone with his bag. He was wearing a muscle shirt that highlighted his features, and those feelings rose in me again.
“Hi, Gerry, where’s your crew?” I asked. “They bailed on me”, he replied. “But Tuesdays aren’t quite the same if I don’t get to see what you’ve prepared for me.”
“What do you mean?” I said rather coyly with a knowing grin.
“Exactly,” he replied. “I could use some Heine.”
I looked at him for way too long before I realized he meant beer, or so I thought, then laughed sheepishly and went to open one. The thought that he was eying me caused me to lose focus, and the unopened can slipped from my hand onto the grass. Then, to make things worse, I picked it up and opened it without thinking. It sprayed all over the semi-sheer top I’d worn that day, highlighting the braless cami I’d put on beneath, and my aroused nipples. I turned towards him, raising my arms and swearing before I realized how exposed the wet clothing had made me. Flustered and embarrassed for being so obvious, I walked into the nearby washroom to clean off.
As I tried to dry and settle myself, I heard Gerry near the doorway. I froze and was afraid to turn around, certain he’d see my exposed, aroused state, and the desire in me. He entered the washroom, walked up to me, and, for a moment, simply stared into my eyes in the mirror. I turned as if under a spell. Sensing my condition, he easily hoisted me atop the counter and planted a long, searing kiss on my lips. Disengaging, he raised his eyebrows and head slightly, as if asking permission to proceed further. I stared deeply into those amazing eyes and slowly nodded.
I was flush with desire as he pulled the wet top and cami over my head and arms, then hoisted me to him. My arms and legs instinctively wrapped around him as he began kissing and sucking my neck and breasts. My body let out a yearning moan as I pulled him tight towards me, my splayed pussy spasming with anticipation as I took in his scent.
After minutes of delirious entanglement, he put me down and backed away a bit. As he pulled his top over his head, I instinctively leaned forward to pull his shorts and briefs down past his thighs. His semi-erect cock and bulbous mushroom head sprung from underneath. It was as thick as my wrist and at least eight inches in length. My heart swelled with unbridled lust as I dropped to my knees and stretched my mouth over its head, slurping it to rock-hard rigidity before he stood me back up, spun me around, and placed my outstretched arms on the wall, saying “There’s a better place for that right now.”
He lifted my skirt and slipped my panties off. “Arch your ass up,” he commanded. I willingly complied, aching for him to fill my depths, despite apprehension that much of his massive member would fit. My two previous sexual partners hadn’t had anything like his immense manhood between their legs, but my cunt was overflowing with anticipation, resolute to submit and be tamed by this beast. As I heard a condom foil being opened, he licked my pussy skillfully, causing my legs to shake involuntarily and playing me to the edge of orgasm. Elevated to the precipice of exhalation, he suddenly stopped, stood up behind me, and rubbed his sheathed cock head across my steamy opening.
“Push back if you want this,” he said. I arched my back and eased towards his waiting tool. Despite my excitement and the concern that my pussy would never submit sufficiently for his plum-like head to fit inside me, I wouldn’t back down. He sensed my situation and used his thumb and forefinger to part my vulva, then grazed his blunt tip against my opening, lubricating it with my sodden wetness. I moaned in anticipation and was determined more than ever to take him into me.
A resolute push popped his crown into me. I gasped fervently, then remembered where we were and placed a hand over my mouth. He eased the head out and back multiple times, teasing me while lubricating his tip, then pushed halfway in, grazing my G-spot with anticipatory delight. I yelped with pleasure as his massive girth massaged my cunt and induced copious amounts of juices to flow. I began to wriggle my hips as he returned to slow in-and-out motions, working together to find that perfect angle. Soon, the planets aligned, and I let him know by stilling myself. He sensed this and wasted no time, sliding his entirety into me to crash against my cervix with astounding delight.
The wind was knocked out of me as I cried out with pleasure, lost in abandonment from feeling so stretched and full. I was in heaven and wanted more, needed more. Regaining my breath, I began grinding back into him, slamming my cheeks against his hips while gasping hungrily for breath. I couldn’t believe I’d taken him entirely! That thrill and the blunt cervical contact brought me to orgasm quickly and violently, causing my legs to buckle under submission to his onslaught.
He pulled out, spun me around to hoist me, and lowered me towards his glistening cock. I reached down and guided it into my wanton sex, then wrapped my legs and arms around him and began riding him unabashedly. Guttural screams filled the air as he wrenched another explosion from my cunt, my legs quaking again mercilessly.
He swiftly expunged himself from me, a squelching, popping sound accompanying the sudden void he’d created. As air raced into the deepest caverns of my sex, he lowered me to my feet while steadying me. I collapsed to my knees and engulfed his cock, worshiping it fervently until two massive streams of cum erupted in my mouth. I closed my lips to swallow the immense magnitude of jizz choking me as more hot seed spewed onto my face and chest. As the deluge of cum subsided I massaged the overflow onto my neck and heaving chest, then greedily sucked my fingers and his cock clean.
We regained our composure, then he pulled me up and kissed me soulfully, followed by emphatic laughter. Looking down at me he said, “I think we’d better stop before we’re discovered.”
I kissed his lips and responded, “Only if you promise to come back soon.”
“I’ll definitely come soon, and often, if you’re up for it,” taking advantage of the double entendre while redressing.
“Will you be?” I replied. A smile eased onto his beautiful face, as I wondered if I’d only been another conquest.
“At your service, m’lady, but I warn you. I’ve dreamt of this since I met you, and I’m not one to share. Are you OK with that?”
“Neither am I,” I replied with a wink as I put my things back on. “But for now, can you assist a poor lady in distress and get my hoodie from the cart? I’m looking…vulnerable.”
