Kevin

I sank my dick into her hot flesh, and my body felt electrified. The ruffles of her dress were perched over her tight ass, and her glistening sun-kissed skin beckoned for the love taps only my hands could provide. I smacked her luscious ass and watched her beautiful body jiggle at its impact, and when I felt the tip of my dick leaking with joy I grabbed it and began lining myself up with her entrance.

We always did things like this, my best friends and I. We met in college at freshman orientation, and bonded when we found out we’d all be taking various business courses. I took a few business classes alongside my I.T. major, and by the time I had my Bachelor’s degree I was already starting my first web business. I began an ecommerce website that specialized in selling customizable and engraved gifts and goodies, and eventually I grew it to a platform where stay-at-home mothers with no lives could sell their homemade trinkets for a bit of money to spend on their holiday vacations. I made my first million when I sold that platform, and invested it into what I’m known for now: professionally mass-developing websites.

Brady was my best friend all throughout college, and he was a hospitality major. We met in our first overall business course, and I thought he was incredibly weird for liking wine as much as he did. He’d somehow always have a few bottles of wonderful wine stashed in his dorm room, and we thought we were hot shit whenever I’d come by and we’d pop a cork of fine wine and pour it into our plastic dollar store champagne flutes.

It should shock no one that when he graduated, he opened and grew his own wine distribution service. Now, he is a multi-award winning wine creator with acres of his own grape yards, and he just began his own monthly shipping service that distributed his limited edition wines.

Me and Brady, we palled around quite a bit, and eventually we met these two smoking hot women with banging bodies. And the best part? They were also in the business school. Brittany had a mind for real estate and was constantly talking about how she would one day dominate the all-male marketplace. She studied constantly for her exams and took a few business classes on the side, and always told us she would go straight from school into opening her own real estate firm. Her and Brady smashed for a while before she got caught up in her studies, and they just fizzled out.

I, on the other hand, met a beautiful woman by the name of Tina. Now, Tina had a mind for politics. Granted, it’s the most boring fucking conversation for a 19-year old college kid with wine in his hand to be talking about, but she took every political and business course she possibly could. Out of all of us, she’s the only one that didn’t make all her money by opening her own business. She did, however, make all her money by becoming the go-to public relations woman for everyone who was anyone in politics.

She always said she didn’t have her own business, but we all know that’s a bunch of bullshit. She works out of her home, takes meetings in her guest house out back, and charges outlandish fees for completely fixing everything about someone’s image.

That’s actually how I’m here now as I slip my dick into the tight entrance of this faceless, masked woman. Her perky tits are slicking across the silk bedsheets of one of the many rooms in this sprawling island estate, and I could feel the heat of her body gulping me down as her pussy opened wide for my cock. She was so tight, and so perfect, and when I finally bottomed out and felt her ass clench against my pelvis, I felt something burst inside of me.

I began pounding into her and I watched her splay her hands across the headboard. My balls slapped her swollen clit while obscenities splashed from her lips, and when I reached down and wrapped my hand around her hair, she tilted her head back and said those three beautiful words every drunk man with a boner wants to hear.

“Yes, please. More.”

Skin slapping skin soon filled the room and the rest of the drunken party fell into the background. The thumping music was vibrating the walls as it drowned out the rhythmic thumping of the headboard, and I felt the walls of her swollen pussy begin to flutter around my cock.

“Yes, baby. Take it all. God, you’re so tight.”

I dropped down and began rolling my hips into hers, and when she buried her face into the pillow I knew she was done for. I didn’t know her name, I didn’t know where she had come from, and I didn’t even know what color her eyes were. All I knew was that I was filling her sweet pussy with thick streams of cum while her walls gulped every drop of essence that was available for me to give her. Her body was trembling and her ass was red, and I collapsed on top of her before I slowly trailed the tips of my fingers over the raised pattern of my handprint on her skin.

“Holy fuck,” she breathed.

I rolled off her and laid on my back while my cock slowly dwindled back down to size. Never in my life had I ever orgasmed as hard as I just did, and I felt her curl up into my body while silver stars burst in my frame of vision. I knew I told Brady I’d come back out to the party when I was done, but the only thing my trembling legs wanted to do was feel this soft, beautiful woman snake hers in between mine.

And it was if she had read my mind.

She sighed in content and laid her head on my shoulder, and slowly I began to untangle the knots in her hair. The thumping of the music had my eyes fluttering closed, and the only thing I could think about was how hot and spicy her pussy felt around my dick. I couldn’t wait to get up in the morning, roll over, and slip right back into her just so I could hear her moan the moment she fluttered her eyes open.

Vacations like this happened every so often with us. Tina was so successful in her career and invested so wisely with her money that she developed quite the nest egg for herself. She began thinking about retirement by the time she was 29 years old, and for her 30th birthday she bought herself an island.

And yes, that happens to be the island we’re all on now. In fact, we all did so well in our respective industries that myself, Brady, Brittany, and Spencer all decided to build the massive house I just fucked this beautiful woman in. We told ourselves that, during our careers, this would be our vacation house. We would come here three times a year for a week each and the only rule was that anything went. As long as there was consent, it happened. The vacations started out as just excuses to drink expensive wines that weren’t Brady’s and eat luscious foods we had imported to the island specifically for when we were there, but they eventually morphed into lusted after events. People in prominent communities began catching wind of our vacation house, and they began inquiring as to whether we would rent rooms out or not during the times we weren’t there.

Now, our real estate mogul, Brittany, was all over that idea. She was already rattling off prices and themes for the different rooms, and Spencer was talking about ways he could advertise to the upper echelon communities. Now, none of us met Spencer until we were in our last year of college, but Spencer’s area was publishing. He had four different publishing houses under his belt that specialized in different things, and the last two years of his career have been focused on the blossoming eBook market and how he can tailor his business to capitalize on it. We met him at a party we all attended off-campus one day, and it actually started when Spencer decided to try and pick a fight with me. We were both drunk and Spencer was determined to take a swing at me because, apparently, I looked like the guy who was hitting on his girlfriend.

It’s funny now because we figured out later on his girlfriend was upstairs sucking the party host’s dick, but that’s beside the point. We duked it out, we passed out on the porch, we sobered up that morning, and the five of us went to go get breakfast.

And that’s how we all became best friends: myself, Brady, Tina, Brittany, and Spencer. Us five moguls ruled our respective industries, and at the beginning of every year since Tina purchased this island seven years ago, we would hold a conference call to coordinate our schedules and plan the three weeks we would all descend on the island and have our vacation. Sometimes the vacation was just a week of us shooting the shit and getting some rest, but other vacations were like this.

Some of the vacations, like the one we took every summer, always held a party or two that would eventually devolve into no-strings-attached sex. People from politics, businesses, and even Hollywood would fly and boat themselves over to attend the party, and there were only two rules that had to be followed: 1) you needed recent doctor papers proving you were clean, and 2) there was never any talk of what happened on that island once someone stepped off it. Sometimes the parties were themed, like the masquerade ball of tonight, and other times it was simply an event where people wore their finest jewels and wrapped themselves in their best fabrics before letting someone rip it to tatters and clatter their pearls to the ground.

I felt this soft woman’s body settle against mine, and all I could think about was how I wish I knew her name. Her breathing evened out and light snores began to pour from between her swollen, pouty lips, and my fingers continued to untangle her hair while I stared lazily at the ceiling. We were on night two of our six-night vacation, and we had another party coming up in a couple of days. That party didn’t have a theme, and I wondered if I’d be able to spot her.

All I knew was her hair was dark and her skin was tan, which wasn’t much to go on since we were on an island that saw sunlight on a daily basis. Her perky tits felt soft and molded against the side of my body, and when her legs finally relaxed in between mine, I prayed to a God I didn’t believe in that when I woke up in the morning, she’d be there. I was getting up there in age, 38 to be exact. Now, that’s not old by any means, but my priorities were shifting a bit. I’d worked hard to build the technological pedestal I’d carved out for myself, but there was no point in owning the houses I did if I had no one to share them with.

After all, there’s only so much furniture a bachelor man needs in his three-bedroom beachfront property on the West Coast.

I wasn’t about to make this woman at my side my wife or anything, but I did feel a longing tug to wake up to someone. Yes, the sex was mind blowing, and yes, my dick would twitch with her scent on it in the morning and search for that silkened slick I’d just got done filling with my essence, but I also wanted a bit more than that.

I wanted someone I could connect with like that again.

But, when I woke up that morning, the side of the bed she was laying on was cool and there was an emptiness in between my legs. My morning wood jutted up to the ceiling and the afternoon sun was streaming heavily through the curtains, and I could hear Brady yelling god knows what up the stairs.

So, I threw the covers off my body, traipsed into the bathroom, and decided to take a shower.

Maybe if I got lucky enough, she’d recognize me at the next party…

… if she even came.