Shelby's Dirty Vacation free porn video

“You’re such a whore, Shelby! But that’s still fucking hot…” Chelsie said as I briefly mentioned one particular aspect of my vacation to the Cayman Islands. “How were they? Big? Muscular? Come on, Shelby, details!”

“Geez, let’s not be too demanding here. It was just sex on the beach with three incredibly hot guys! After all, I was on vacation…” I just stared at Chelsie, hoping she wouldn’t judge me for spilling the contents of my wild and dirty vacation.

“Oh, please do tell! And you couldn’t have taken me with you, you whore?! I wouldn’t have minded seeing that…or even being a part of it…” she dropped off as her face turned several shades of red and her panties quickly became soaked.

“Okay, okay, but I’ll warn ya up front, this is pretty graphic and very dirty. I have a hard time keeping my fingers out of my cunt when I think about it…” I began recalling the dirty events of that night on the beach after I met those three guys.

The day started off normal and innocent just like it always has. But something about this day was different – this was the day I left for vacation, to spend a week in the Cayman Islands. What made the trip even better is that I was going alone. No parents, no siblings, nothing. Just me and my slutty tendencies. And did I ever plan on putting my slutty habits to work. I just didn’t think anything like that was going to happen.

My plane landed around noon, where I then headed straight for the hotel to check in and kind of relax after the long flight. After the bustling cab ride, being checked out like crazy by the cab driver, and finally fighting through the crowd of other tourists, I finally made it up to the front desk to check in. Upon receiving my key, I quickly made my way over to the elevator. And from there, I began to ascend to the room that would house some of my potential behaviors of my trip – assuming there were any potential prospects.

I didn’t have to wait very long for that either. As soon as I hit the elevator, out popped Mike – a successful entrepreneur from the U.S. The meeting seemed casual, like two people on a business trip rather than meeting on a vacation. The subtle glances and hellos while waiting for the elevator were enough to attract my attention to him. Hmm, this guy seems interesting, I thought to myself. The thought bugged me all the way to my room. And from there, I began kicking myself for not at least getting his name. I then wondered if I were going to run into him again. He’s staying in the same hotel! Of course I’m gonna see him again…

I showered and settled in my bed to get some sort of rest before hitting the beach to get work on some sort of a tan before the night festivities began. I began flipping through the channels in hope of something arousal to get me by. But of course there was nothing on, so I decided to succumb to a light nap.

“Shelby! Details of the beach! I don’t need to know about the events leading up to you being completely filled up and ravished!” Chelsie said, snapping me from my story.

“Hey, bitch! This is my story! And it’s important to know what led up to this…” I snapped back before I continued my story.

*

Hard and deep, his thick cock plunged in my wet hole. I was moaning out like a bitch in heat as he ravished my body with his mouth. Over and over again, his cock hit my deepest depths. I couldn’t believe what was happening. I looked up and saw his face – this face I saw down at the elevator. I couldn’t believe he was fucking me, fucking my tight pussy when we didn’t even know each others’ name!

It seemed like he had no end in sight, as his thrusts continued to pound my pussy. As for myself, I was near a very powerful orgasm, one that could possibly rattle this bed loose. He showed no signs of being close. He kept the same speed and intensity as I rode wave after wave of pleasure that crashed through my slender frame. Yet he still didn’t stop…

I snapped awake, breathing deeply, before looking down and noticing the wet puddle between my legs. The dream seemed so real and vivid, as if he were actually there fucking the hell out of me. My clit and pussy throbbing so bad. They were aching to be touched, to have that sweet release that I crave every second of the day.

I ran my hand down to my cunt and began toying with my clit, finger slipping a bit lower to collect my juices before running them over my sensitive bud. I circled my clit, flicking it with each pass, feeling my body tense and that familiar feeling build in my stomach. I reached lower and sank two fingers deep in my pussy, working and rubbing on my spot that gets me off every time. This session, I decided to be bold.

My juices were running heavily from the vivid dream I had. I collected them as they ran over my ass and used it as lube to work my finger in my tight orifice. So there I was lying there with two fingers in my cunt and a finger in my ass. I felt somewhat full and fucking loved it! I sped up my own assault and soon enough, I came with an explosive orgasm. I squirt so much that I was afraid the bed would still be wet when I got back later that night. I just lay there in post coital bliss, lightly running a finger over my clit, with closed eyes, while I thought about that sexy guy at the elevator. I was determined to find him just to know if he actually fucks that well or if that was my imagination in overdrive.

I got out of bed – completely naked, I might add – and made my way over to my suitcase to retrieve my bikini. I decided to pull out the sexy one. You know, the skimpy orange one with the thong bottom. I remembered how crazy it used to drive your brother, so I decided it would be fitting for this trip. I quickly slipped into it before grabbing the giant shirt that accompanies it so well once it’s lying on the beach and not on me. But damn, was I ever excited to show off what I have in hopes of landing a good lay on the first night there.

“Wait, so you had a dream that this guy was fucking you in your hotel room?” Chelsie asked, once again interrupting my story.

“Yeah! And it was completely unexpected too…”

“Hey! You teased my brother on purpose, didn’t you? By the way, did you ever fuck him?” She asked with a raised eyebrow.

“He was too easy to tease! And as much as I love sex, I haven’t fucked your brother because of you. However, I’d love to…damn, he’s sexy too…” I trailed off as I became distracted. “Damn you, bitch! Let me get back to my story!”

I was at the beach for no longer than fifteen minutes – and stripped of my giant tee, so you know – when guess who walks by. I about flipped shit I was that excited. And damn did he look good without a shirt on! I sat back and began admiring his sexy body from behind my sunglasses. In a way I was hoping he didn’t recognize me because I was nervous as hell with him just a few feet away. At first it seemed like he didn’t recognize me until he looked over, looked away and then looked back with a smile. I couldn’t help but smile back at him. And then he approached me. Holy fuck, was I ever nervous!

“Hey, good lookin’,” he said with a wink. I about melted right then and there.

“Hey, how are ya?” I shot back with a smile, my eyes roaming up and down his body.

“Pretty good and now even better that I found you.” My eyes the size of saucers behind my glasses.

Holy shit! And I’ve been looking for you, my sexy piece of meat… I wasn’t aware I was biting my lip until I noticed the smile on his face turned to a total shit eating grin. My face turned a few shades of red, I’m sure. “You know, I was hoping to run into you down here. Not gonna lie, I was pretty pissed that I didn’t get your name when we were on the elevator.”

“I know, I was pretty disappointed with myself that I choked when I first saw you. Can you blame a guy for fumbling around a gorgeous girl such as yourself?”

That was the end of me. My bottoms were completely soaked, my face like fifty shades of red and my mind reeling. “Well, this also works both ways. I was caught off guard by your good looks and dropped the ball on that one as well.” Holy shit, I was fucking soaked.

“Well, I’m glad we ran into each other. I’m Mike,” he said as he continued that heart melting smile.

“I’m Shelby. And I must add that I love your smile!” I beamed back, his face turning red and his smile becoming bigger.

“You sure know how to make someone blush…by the way, what are you doing tonight?”

“I planned on finding you, hoping you’d wine and dine me, get me drunk and then take me back to your room and fuck me senseless!” I smiled at him as his mouth dropped. “I’m only kidding, Mike! I was hoping to hit some clubs and see what they are like.”

“Oh wow, you are not shy! But if you’d like, you can go with my friends and I. We could use another girl since mine decided to dump me before this trip.” He looked kind of sad as he said this.

“I’d love to join you and your friends! At least I won’t be alone tonight.”

“Are you here by yourself? I noticed that no one else was with you.”

“Yeah, I figured taking some time to myself and meeting new people would help out.” I continued scoping out his body. And damn, did I love what I saw!

“Well, here you are! But, um, how do I get a hold of you later?”

“Just come by my room. It’s 613.”

“I’ll be by your room at eight then,” he said as he smiled. “I’ll let you get back to whatever you’re doing. I have some stuff I have to do before tonight. See ya later!”

“Okay, see ya!” With that, he walked off, my eyes following him as he walked away. Don’t be falling in love as he’s walking away.

You see, Chelsie, I was so fucking wet after he walked away. No guy has ever done that to me before. I don’t know what it was about that boy, but damn, he had me tripping over myself as I began preparing for the night. I showered again to get the sand and salt water off me, but all I could think about was having his cock inside me. While I was showering, my hand kept lingering around my pussy, threatening to dive deep and potentially make me late for his arrival. I resisted the temptation to frig myself silly and hurried up with washing the rest of my body.

As for what I wore, well, I happened to see my strapless mini dress peaked out from the corner of my suitcase. It seemed very appropriate for the night, so I slipped into it – purposely not wearing panties. I was going to give him a show and if he didn’t want to fuck me by the end of the night, then I was going to find someone that would.

Sure enough, right at eight, that sexy piece of meat knocked at my door. Butterflies started up all over again as I answered the door and placed my arm on it in a sexy and seductive manner. I want to fuck your brains out right here, right now…

“Well hello, gorgeous…” Mike’s eyes roamed my entire body, my juices threatening to run down my legs.

“Hello, sexy…” where have you been all my life?!

“You about ready to go?” He asked, his eyes still roaming my body.

“Mmhmm!” I walked out, making sure to grab my purse before taking his hand and walking down the hallway with him.

The party scene was unreal, nothing like I’ve ever witnessed before. There were all sorts of exotic dancers – strippers, acrobats, feathers, lights. Anything you can name and it was there.

We hit a few different bars before finding the cities hottest club. There, we met up with his friends and we all ventured into this giant club. Oh, Chels, you should’ve seen this fucking place! There were at three floors and different balconies from what I could see. But noooo, that was off limits to the VIP’s. Who’s so damn special in the islands that they deserve access to the upper levels while the rest of us fight for a spot on the dance floor? Of course, being the outspoken one, I almost got us kicked out of there for asking that exact question.

“Miss, miss, no one goes there unless they are VIP. Except that or leave the club!”

I opted to not leave the club, so I kept my mouth shut and followed my sexy piece of man meat up to the bar where I decided to have some fun. Alcohol running through me by this point, I reached around the front of his pants and took a firm hold of his bulge – apparently he was feeling rather worked up himself – and began rubbing and caressing it, everyone oblivious to it considering we were right up against the bar. He jumped a bit, but let it happen. Then the bastard reached behind him and discovered I had on no panties.

He slipped a finger in my thoroughly wet hole and went to town on my cunt. I had to bite into his shoulder to stifle the loud moan that would’ve come screaming out of me. He found this amusing – I’m assuming – since he buried a second finger deep inside me. And somehow he knew I was about to cum! I was right on the verge of flooding his hand and the insides of my thighs when he let go and pulled away. I was pissed, so I gave his cock a very hard squeeze and pulled away. He shot me a smile, and once again, I melted. All was forgiven that he didn’t make me cum.

After a few rounds of drinks – all supplied by him of course – he then decided to introduce me to two of his friends. “This is John and Kyle. You two, this is Shelby. I met her down at the beach earlier today and she gladly decided to join us tonight.”

I took a look at his friends and about died. All three were gorgeous as can be. I was planning on taking each of them for a ride while we were there. I planned on starting with Mike, then moving to John and then finishing with Kyle. With some luck and seduction, I was going to pull off the trio at the same time. I figured luck would be the biggest factor, unless they were looking for a slut to take advantage of. And if that were the case, then they found one in me. Little did I know, that was their plan from the get go.

After some playful banter and my best game on display, I leaned into Mike, “I don’t know about you, but I’m about ready to get out of here.”

“I’m thinking the same thing,” he replied before saying something to Kyle and John. He grabbed my hand and led me out of the club and back to the hotel.

So, Chels, at this point I was shitting myself. I couldn’t believe that I was about to have this guy fuck the ever loving shit out of me. I was going to make him rail my slutty cunt for all he was worth before cumming deep inside me. But for some reason, my expectations and reality didn’t seem to want to line up that night.

We made it to the hotel and immediately he hit the button for the sixth floor. Okay, so he’s gonna fuck me senseless in my room. I can deal with this…oh shit! I hope there’s not a stain my sheets from play time earlier! But when we reached my door, and after I opened it to drag him inside, he pulled me in really tight, gave me a deep and hard kiss and wished me a good night. What the fuck? Who fingers a girl in a club and then doesn’t finish the job later? I was so fucking pissed that I stormed into my room and threw myself on the bed.

I was too drunk to try and go out and find a random guy to take care of my aching need, so I decided I’d do it myself. I reached for my vibrator that was in my bag, turned it up to the highest setting and pounded my pussy until I was screaming as loud as I could with a very violent orgasm. I collapsed on the bed and was asleep within a few minutes.

“I can’t believe he fingered you in the club but didn’t fuck you afterwards! Wow, that’s crazy!” Chelsie interrupted once again.

“Right?”

Anyways, so I awoke the next morning with a wonderful headache and the sun shining directly on my face. Not only did my head hurt, but the sun made matters worse when I opened my eyes. Fuck. My. Life! Was all I could think about while I lay there, naked, and tried to replay the events of the night before. Then I remembered that Mike didn’t fuck me and that made me feel even worse. Then came the knock to the door.

Me, being me, walked straight to the door and checked through the peep hole to see who it was – naked of course. Seeing it was Mike, I took my chances and opened the door for him to see me in all of my glory, my pussy an instant wet mess.

“Whoa, hey, Shelby…” he said as he looked directly at my breasts.

“Hey, Mike, see what ya missed last night?!” I prodded at him while thrusting out my chest towards him. “You could’ve fucked me last night. In fact, I was expecting it because of that little incident at the bar! But no, instead I had to come back here and fuck myself senseless since you didn’t do it!” I was fuming, letting him know what he should’ve fucked instead of what he fucked. You know, Chelsie, his hand.

“I’m not that kind of guy! Now get dressed, we’re going to get breakfast then we’ll hit a couple bars before settling in on the beach.”

What the fuck, right? I mean, here I am presented buck naked to this incredibly gorgeous man and he still turned me down? What the fuck was it gonna take for him to fuck me? Getting him drunk?

I quickly got dressed – throwing on a more modest bikini with a sarong. We headed downstairs, got some food and then hit a couple hotel bars that were on the way to the beach. I needed something to curb the urge to off myself. And damn, did that margarita have what it took to do so! I felt like a champ and back to my true self after I finished the second one.

Of course I still wasn’t happy with Mike for denying my pussy his sweet cock, but I had something up my sleeve to take care of that. I was determined to make him fuck me, even if that meant straddling him and impaling myself on him. I felt greedy and sex starved, but who doesn’t when they’re on a vacation and surrounding by a bunch of beautiful people?

When we hit the last bar, we ran into John and Kyle, both wearing nothing but shorts and holy shit! I could’ve died and not have cared. Both had bodies as well. My mouth started watering, pussy started running as I took in the sight of all three pieces of sexy man meat that stood right in front of me. There was no way I was going home without having fucked at least one of the three guys.

“I’m soaked just thinking of what these guys looked like! Damn, girl! I can only imagine what you were going through while actually looking at them!” Chelsie piped up again.

One more margarita and we were finally on the beach. Or so I thought we were gonna stay. No, we kept walking past the area where most of the tourist hung out. We kept walking until the beach took a turn and ended up in a cove so no one else was going to see where we were. I was confused at first, but I still went with it. At first I thought we were just going there to get away from everyone, but then I realized there was a completely different motive for being here than I originally thought. It all seemed to click once Mike walked up behind me and removed my sarong before grinding his hard on into my ass and kissing my neck.

But once again, I was disappointed as he pulled away and sat back on the sand, lounging out as the bright sun beamed down on all of us. John and Kyle sat down as well, so I took the cue and sat down between Mike’s legs.

Like I said, I was frustrated. I wanted him to wreck my pussy last night, and he didn’t do it. I thought maybe he’d talk me into going out in the ocean and fucking me out there. Yet again, he didn’t. I was beginning to become very confused by him. Why won’t you fuck me?!

And then things began to heat up a bit. Mike leaned forward and pulled my against him so my back was against his chest. He began kissing my neck again, but this time, his hands were roaming my body. He rubbed all around my stomach before dipping into my bikini bottoms and quickly rubbing the clit. He brought his hand back out and this time, he placed them on my breasts and began tweaking my nipples. This is when the other two noticed and started watching. Talk about adding to the confusion.

“Shelby, I’ll bet that you won’t suck Mike off right now…” Kyle spoke out, daring me to suck off their friend. “But we have to be able to see it.”

“Really?” I asked as I turned over and quickly pulled Mike’s cock and began bobbing up and down on it, eliciting a moan from him. “Mmmm, that all you got, big boy?” I was trying to see if he’d be bold and dare something with myself and someone other than Mike. I wasn’t disappointed either.

“Okay…you won’t suck off Kyle and John at the same time,” Mike spoke up before Kyle did, giving me a very big surprise. But of course, I was very turned on and had no intentions of turning down a dare.

I reached over to both boys and pulled out their impressive members and began pumping theirs cocks in my hand before sucking on Kyle first, then going over to John. I passed my mouth back and forth between the two until I felt a finger slipping into my pussy.

“You wonder why I didn’t fuck you last night. I wanted to make sure I had enough reserves to give you a proper fucking. The kind of fucking a whore like you deserves. But I knew I couldn’t do it alone, I’d have to have some help. A whore like you is insatiable and takes a lot to get the full satisfaction you crave. And once I’m done with you, you won’t want sex for the next day or so. Unless I’ve underestimated you, that is…” he said to me, chills and excitement running through my body, my bottoms completely soaked with juices running down the inside of my thighs from his expert fingers. “But first, we’re gonna play a little game to see who fucks you and where they fuck you. It’s called ask which hole you want. I’m gonna ask the others which hole they want and that’s the hole they are gonna fuck first. Then we’ll rotate until each of us has fucked every hole. Then we’ll cum in the hole we started with.

“John, which hole do you want?”

“I want her ass.”

“Very well…Kyle, which hole do you want?”

“I want her pussy,” Kyle answered as he licked his lips.

“Okay, then that leaves me with her mouth. Let’s get started!”

My three boys stripped naked before removing my bikini. Mike placed me on all fours and waited for Kyle to get under me. Kyle immediately thrust up into me and began fucking me hard, my moans coming out loud. John came in front of me and thrust his cock in my mouth to get it wet enough to penetrate my ass while he finger fucked it pretty hard. After a few minutes of that, he moved around behind me and slowly worked his length inside me. I felt so full.

Together, Kyle and John started fucking me in a nice, hard rhythm while Mike stood back and watched for a few minutes before joining the fuck fest and thrusting his glorious meat pole into my waiting mouth. I greedily sucked on his shaft, swirling my tongue around the head as he pulled back with each thrust. All three of my boys began fucking my in rhythm. It was so fucking hot, Chelsie! You should’ve seen how slutty I looked with a cock in every hole. I’ve never felt so full, yet so hot and alive. My insides were on fire as they abused my holes. Within a matter of minutes, they had me cumming very hard. I squirted all over Kyle.

I forgot to mention something to you and Mike before this all had gotten under way. I have no gag reflex. It’s an amazing thing because he was able to repeatedly fuck my throat and I was taking it like he wasn’t even there. It seemed like he was waiting for me to start sputtering and chocking on his magnificent cock, but it never happened. The urge to do so never arose and I think he realized this quickly as he really began laying the meat to my face, fucking my throat hard and deep.

Apparently this was a major turn on for him because not long after I came, he was shooting his load down my throat. I took it all in stride and did my best to not miss a drop while my other holes were being reamed by the other two.

Mike said nothing about my lack of gag reflex. I’m sure he was just fine with letting them find out on their own. And after awhile of being fucked and a few orgasms later, Mike decided he wanted his turn on the rest of my body.

“Okay, boys, let’s switch. I’ll take her pussy while, John, you take her mouth and Kyle, you take her ass.” My boys switch up and the feelings were pretty much the same, but Mike felt a bit bigger than John and Kyle.

I did my best to suck off John while Kyle and Mike guiding their cocks into my other holes, Kyle easier than John since my ass was already warmed up for them. All three were really fucking me hard and rough. I couldn’t believe all my holes were filled at once. I’ve had guys fuck each hole in the same night, but I’ve never had it done at the same time. I loved it too! I felt like a true whore and that I was receiving so much more pleasure than I could’ve ever thought possible. I lost count of how many times I came as they switched places once again.

Mike seemed like the more experienced of the three. I came harder and faster when he was fucking me. He seemed to know how to hit my pussy deeper than the other two and just seemed to know where my spots were. Not to mention, he was very good at hitting my clit with his pelvic bone as he thrust hard up into me. And when he switched to my ass, he just seemed to know what to do with it. He began slapping my ass, each slap ringing out and eliciting a moan from my mouth that was pretty well muffled my Kyle’s cock.

Slap after slap came across my ass. It was burning, but felt so good at the same time. I loved the way I was being treated, treated like the filthy slut that I am. Being used for their own pleasures, or so I thought until one of them confessed to me otherwise.

“So hot…” I heard Chelsie say under her breath.

“Switch!” Mike called out as he was back in my mouth, back where I wanted him, to taste his cum again.

All three began pounding my holes again. I felt some pain, but that was greatly masked by the pleasure I was receiving. I knew there was no way I was ever gonna be satisfied this way again. I would have to subject myself to this kind of fucking again to feel even remotely satisfied. I was pretty ruined for anyone else who wanted to fuck me. That was unless I really took a liking for someone. And that someone had their cock inside me when I violently came, causing him to erupt again. He coated my mouth and throat with his second batch of cum. His cum triggered another orgasm for myself, which in turn, triggered the other two to push in as far as each of them could and blast deep inside me. I finally got the satisfaction I was looking for. I wanted to do some dirty things while I was there and they delivered on that. Now all I wanted was to have steady sex for the rest of the time I was there.

And get this; the other two didn’t notice that I didn’t have a gag reflex! They both kept fucking away at my throat; completely oblivious to the lack of gagging, choking and sputtering that normally would’ve happened had I had a gag reflex.

So, Chels, can ya take a guess as to whom I want so bad right now? Stupid question, considering it was obvious from the get go, but I could’ve had my choice from any of the three studs that ravished and exploded in my holes. Any of them could’ve been mine, but I had my eyes set on one in particular because he was the one that paid extra attention to me after the whole ordeal. He was the one that paid any attention to me in the first place. He was the one who approached me first.

Yes, Chelsie, I’m talking about Mike. He stayed with me while John and Kyle left to go do their own thing. My body was sore and exhausted from the onslaught of cock and orgasms it had. I’ve never felt anything like that before and I’m sure I won’t feel anything like that again. But even that night, as he held me in his arms after making the most passionate love to me, I knew I didn’t need it again. For some reason, I felt like he was all I needed.

It’s surreal, girl, it truly is. Of course my panties and jeans are completely soaked from telling you what happened while I was there, no denying that, but now I have the dying urge to be fucked and get the satisfaction I need right now. It sucks because that won’t happen again. Honestly, I don’t need that to happen again. I just need Mike.

Mike and I had sex every day for the remainder of the time I was there. He gave me the steady sex that I had needed. We slept in the same bed every night, had the most wonderful sex that I’ve ever experienced – well outside from having all my holes completely ravished, but that’s not the point! Point is, I’ve never felt like this with anyone else. Even from the first time I saw him I was completely drawn in and absolutely soaked by his stare alone. What’s happening to me?

That was the dirtiest, yet most erotic day of my life and looking back, I wouldn’t change a thing…

BEEP, BEEP, BEEP, BEEP – text message.

Hey gorgeous! I’ll be around your area in the next couple weeks because of something that came up job related. Thought I’d let you know and hopefully we can get together again. I’ve missed you! Oh and by the way, it looks like I’ll be moving to your area because of this job. We’ll talk further about that once I get there.

“Oh my fucking gosh! He’s coming here!” I said after reading the text out loud, Chelsie and I just staring at each other, myself in shock and complete excitement. “I can’t believe this!”

*