tagLesbian SexWish You Were Here

Wish You Were Here

byJukeboxEMCSA©

(A brief disclaimer: The Ocean Club in this story should in no way be confused with the One and Only Ocean Club, and this story in no way represents any events, occurrences, or incidents at the One and Only Ocean Club, nor is it intended to represent the behaviors, inclinations or proclivities of the One and Only Ocean Club's guests. Any resemblance is entirely coincidental.)

Postmarked February 16th, 2009

Front:

A picture of an idyllic white sand beach at sunset, the waters tinted the same glorious shades of orange and red as the clouds. A few palm trees stand in the background, and a few happy couples watch the sun disappear below the horizon. At the bottom, a legend reads, "Paradise Island--The Closest To Heaven You'll Find On Earth".

Back:

Dear Beverly,

Having a wonderful time. Wish you were here.

Hugs,

Tiffany

*****

Postmarked February 18th, 2009

Dear Beverly,

Sure, it was mean, but I couldn't help myself. After all, you were the one who was saying, "Oh, you should just take the cash value of the prize, Tiff! You had your cell phone shut off last month, you had to move back in with your terrible aunt, and you can't afford to jaunt off to the Bahamas, even if the trip is all-expenses paid!" So you'll understand if I decided to tease a bit before giving you all the juicy details. (And don't think I don't totally know you were just saying that because your job was keeping you too busy to take the second ticket. You know you'd be right here with me if you could. I'm still bummed out about that, you know. I mean, it's nice to have handy studliness whenever the urge strikes, but Ethan's nowhere near as much fun to hang out with as you are. He's well-endowed in a lot of attributes, but conversation isn't one of them.)

My aunt said the same thing you did, by the way (the meanest thing I can say to anyone!) She heard the cost of the travel package, and she was all, "Cash that puppy in! Spend a weekend in Miami if you need to waste time at the beach!" But I am so glad I stuck to my guns--this is a once in a freaking lifetime experience! We're not talking about a week at the Hilton, here. This is an all-expenses paid two week vacation at the Ocean Club--and I gotta tell ya, Bev, the words "all-expenses paid" take on a whole new meaning at a place like this. We have our own butler. Seriously, our own butler, on call 24/7. We say "More champagne, please!" and he says, "Yes, Madam." I'm actually being called "Madam" by someone, and without the words, "Could you please be a bit quieter?" after it!

This place is so awesome you wouldn't even begin to believe it, Bev. My nicest outfits barely qualify as casual-wear here. I've seen five actual movie stars--and I'm not talking washed-up actors or guys that you maybe saw on TV once, I'm talking actual bona fide "Oh my god is that Tom Cruise?" type movie stars. This is the kind of place that royalty rents out when they go on vacation. (And I'm not just saying that, by the way. I actually had lunch with a Duchess yesterday. I only ordered a salad so I wouldn't embarrass myself by using the wrong fork.)

We're eating five-star cuisine, Ethan's playing nine holes of golf every day, and I'm blissfully tanning and swimming and snorkeling my brains out. And then at night we hobnob with the rich and famous. Well, I do. Ethan's so totally star-struck that he's coming across like a total twerp, while I have managed to remain suave and calm and talk to them like it's no big deal and I meet big celebrities all the time. Is it wrong of me that I've started ditching him?

I promise I'll write more later.

Hugs,

Tiffany

*****

Postmarked February 21st, 2009

Dear Beverly,

I know, I know, what's the point of writing letters when you're on vacation if you get back before the letters do? Why not use the free wi-fi Internet access, or the free long-distance phone service? Because this is a vacation, honey, and it is one hundred percent traditional when on vacation to take the phone off the hook, let the mail pile up (the email, too), and ignore the rest of the world until it's time to get back on the plane and force yourself back to real life. (I don't know how I'm going to get by without a butler. You laugh, but once you've gone butler-y, you can never go back. Maybe I can press a homeless person into service or something.)

So that's why I haven't called. But I had to write you to tell you about the most unbelievably awesomest awesome thing to happen on this vacation. You know Camille Rothschild? (See, this is the advantage of writing a letter to you about this. I can skip all the parts where you act all nonchalant and pretend not to know who she is, when we both know full well she's one of the richest and most eligible heiresses in the world and she's got her own line of clothes and she's going to inherit a whole vastly huge business empire and you read about her in the tabloids all the time, and then I point that out to you, and you try to insist that you don't read that stuff and I have to go into your bedroom and grab one out and wave it at you triumphantly. This way is much easier.)

Anyway, she's totally hanging out with me!

I will now pause for your squeals of jealous delight. Okay, pause over. I'll tell you how it happened.

I was out dancing the other night--I have by now almost completely ditched Ethan, by the way, and I think he's actually screwing one of the maids. How skanky is that? You come to the height of the upper class, the place where the rich go to get away from it all, and you wind up schtupping one of the maids when she comes in to tidy up. Ugh. I mean, I'm not angry or anything, Ethan and I weren't ever exclusive and I'd never thought of him as much more than "cock of the hour", but still, tacky much?

Anyhow, I was dancing, and drinking, and putting it all on the club's tab because hello, all expenses paid, and I was feeling absolutely no pain because they do these awesome martinis here (it's so totally awesome drinking a martini here, I feel like a female James Bond.) And then I stepped off the dance floor, and I suddenly realized that I was having too much alcohol and dancing and not enough water and stretching, because all of a sudden my legs cramped up so bad I literally fell over.

And this girl spotted me, and ran over, and she was like, "Oh, are you all right?" And I was gritting my teeth, and I was trying to stand but it just was not happening, but I was being all stoic and saying, "Oh, I just over-exerted myself a bit, it's just a bit of cramp."

So she said, "Here, let me try to help," and she stretched me out and started trying to massage my legs back into shape. And that's when I recognized her. If it wasn't for the pain, I would have totally freaked. Camille Rothschild, girl with her own brand of perfume and more jets than I have dresses, is giving me a massage! Suave and calm has its limits, and that would have been mine if my legs hadn't been distracting me.

But the massage wasn't doing any good--and that's not a knock against her. Her hands felt damn good, and she was really working her way up and down my legs, but my muscles were knotted up good and tight and they had no interest in letting go. But this is where it gets truly awesome. Camille recognized me from the Ocean Club! She had her chauffeur (Ooh, chauffeurs! I might need a whole staff of homeless people!) pick me up and help me into the car, and we drove back to her villa at the club.

And oh my god, if you think the rooms are swanky here, you can't even imagine the villas! This is like a four bedroom house in the middle of a luxury resort, and it's all Camille's! I haven't asked her how much a night it is, because rich people don't do that (and no, I'm not pretending to be rich. She knows I won this trip, and she's totally cool with that.) But I looked it up online, and she's spending a cool ten grand a night for this place. She doesn't use the resort staff, either. She has her own private butler (is it still a butler if it's a woman? Does it become a butler-ette or something?), and her own private chauffeur (chauffeuse? Camille doesn't have any guys on staff. Me, I'd have a hard time resisting having some eye-candy around, but I guess she wouldn't have a problem whistling up men when she needs to.)

And most importantly for purposes of this anecdote, her own private masseuse. I thought I was getting good massages at the spa, but this woman had my muscles melting like butter. Seriously, after five minutes I was totally limp, like a ragdoll made of wet cardboard crossed with a boneless kitten. I barely even remembered who I was, let alone where. Those cramps didn't stand a chance.

And after that, we chatted a little. Then we chatted a lot more. Camille thought it was really neat that I'd won this trip, and she agreed with me that Ethan was a total punk, and we totally bonded complaining about guys and how we wished that we could get all the fun of being fucked without the hassles of dealing with them. And the whole time, her masseuse (Andrea, her name turned out to be) was just working away at my muscles until I was tingling all over.

I wound up actually nodding off, it felt so good, and I apologized when I woke up but Camille was totally cool with it. We hung out all the next day, playing tennis (she won, but I held up pretty good for someone who doesn't have all day and every day to practice) and swimming and tanning, and then we went out clubbing again...and between you and me and the skeezy guys in the post office who probably read everybody's mail, she slipped me these little pink pills that made my head feel like it was full of cotton candy. In a good way. I was lucky she was there to help me out, because I don't know what they were, but they were strong enough that I needed a thinking-brain girl to help me out.

I am going to have such a hard time getting back to reality.

Hugs,

Tiffany

*****

Postmarked March 2nd, 2009

Dear Beverly,

This is just the most motherfucking awesomest thing ever in the history of the world! Camille and I were talking Saturday night, and I was saying how much it sucked that I had to go back home the next day, and she said, "Why not stick around?"

And I kind of snorted, and I pointed out that I can't afford even a single day at the Ocean Club without the contest people paying for everything, but she just waved around the villa and said, "Plenty of space here."

And I asked how exactly I'd get back if I didn't use the ticket I got with the contest, and she just grinned and pointed out that she had a private jet on standby whenever she wanted it.

And I pointed out that my boss would kind of fire me if I just decided to extend my vacation because I felt like it, and she asked where I worked, and when I told her she just got this wicked little gleam in her eye. And the next thing I know, she's on the phone with the CEO of my company--not my boss, but the CEO of the international conglomerate that runs the company that owns the branch that employs my boss. And she's all, like, "Hey, Reggie, it's Cammie! Could you do me a teensy favor?" And suddenly, I'm on indefinite paid leave. Let me just say that again, since I don't have a highlighter. Paid. Leave. Retroactive, too. I can't fucking believe it.

So now I'm unpacking my stuff in the villa. Not sure how long I'm going to stay, but it could be quite a while--I'm certainly not going to get sick of the Lifestyle of the Rich and Famous any time soon, and Camille doesn't seem to be getting sick of me. She's acting like we're having a slumber party together or something. When I brought over my suitcase, she was giggling like crazy, and all of a sudden she shouted, "I know! Present time!" And she raced out of the room for a minute, and when she came back, she handed me this amazing brand-new MP3 player like it was a Cracker Jack prize. I'm still playing with all the features--It's way better than anything I could ever get. (And not just because it's expensive, too. Apparently, she owns the company that makes it. This is like a new prototype pre-production model, won't go on the market for months.)

Anyhow, now I feel even more guilty that I'm here and you're not. I know you'd totally hit it off with Camille (unlike Ethan, who is on his way back home right now. The invitation was not extended to him, and I didn't ask her to.) Maybe when Camille takes me home, I can introduce you to her and we can all hang out together. That would be truly awesome.

Hugs,

Tiffany

*****

Postmarked March 16th, 2009

Dear Beverly,

I'm not even sure you'd recognize me if you saw me. Camille and I turned out to be the same size, so she's sharing her clothes with me. I've never dressed so hot in all my life. I'm totally turning heads everywhere I go. (Which is kind of a problem, because living at a villa with four other girls who do practically everything with you, it's kind of hard to find someplace to sneak off and have sex. I've been doing my best to handle it myself, but sometimes there are urges fingers just can't satisfy, you know?)

Sorry I haven't gotten in touch with you these last two weeks. There's something weird and fritzy between my laptop and the villa's wi-fi now that I'm no longer an official guest, and I'm not tech-savvy enough to figure out what it is so email is kind of by the wayside at the moment. I know I should try to fix it, but somehow when you're lying on the table getting a three-hour massage from a professional Swedish acupressurist while listening to music through your earbuds, everything just seems less urgent.

And I'd call, but I still haven't figured out how to get a line out. (They've explained it to me something like seven times, but it always sounds like the grown-ups from "Peanuts" talking and I always wind up doing it wrong.) The phones are all routed funny--something to do with Camille's business phone network. She isn't just here on vacation, she actually lives here, and does all her work by teleconferencing. (I know, you're probably thinking something snarky right now about how hard it must be, inheriting things for a living, but I've spent a little time watching her work. She's actually a bad-ass businesswoman. I was surprised to see her talking textiles in Chinese, arguing over factories in German, and generally bossing people around. I was like, "Isn't your dad actually in charge of this stuff?" But she told me that it's been ages since her dad actually made any of the decisions in the company. She's the one in charge, apparently.)

So I finally decided to just write you another letter. It was so funny--when I mentioned it to Camille, she actually got this little sour look on her face for a second! She hid it right away, of course, and she was all helpful and offering to give the letter to her secretary to mail out so that I wouldn't have to bring it up to the front desk (like I can't walk it over myself?), but I could tell what was really bugging her. She was jealous! All that money, all that power, but you're still my best friend and she's not. (Which isn't to say she's not totally nummy, or anything. She's hilarious, smart, rich, gorgeous and everything I would want in a husband except for the pussy. She is definitely in the number two spot. But don't worry, Bev, she's never going to beat you out. You're every bit as cool as she is, and you beat up Missy Malloy when she stole my boyfriend in ninth grade. Camille hasn't beaten up anyone for me. She probably has people for that, or something.)

Anyhow, what have I been up to the last couple of weeks? Pretty much professionally lounging around, that's what. I'm getting so pampered that I'm starting to lose the ability to do things for myself. There just always seems to be a butler or a maid or a chauffeur around to take care of it, and all I have to do is lie there and be pretty. (Which I'm good at.) Camille and I have done lots of shopping (she helped me pick out some lingerie that's going to make Whatsisname beg me for forgiveness when I get back--and it's so comfortable, too! I pretty much just wear it around the villa all day now, since it's just us girls.) We've been out clubbing (I try to say no to those pills she has, but she always gives me this mock-stern look and I just say "Yes, ma'am," and then it's Little Miss Candy-Brain all over again. I just wish they didn't get me all hot and bothered. Camille does a little too good of a job keeping the men away when I'm too fuzzed out to make decisions, if you know what I mean. Just once, I'd like to wake up in a strange man's bed after a night like that.) And of course, I've been tanning, swimming, and getting lots of massages and spa treatments. (That MP3 player has been an absolute godsend! It's even waterproof, so I can wear it swimming.)

Still not quite bored with the ultra-rich lifestyle, oddly enough. At least, not bored enough to go back to living with my aunt. But you know I miss you.

Hugs,

Tiffany

*****

Postmarked March 23rd, 2009

Dear Beverly,

So the last week has seen some interesting developments. They might kind of shock you, in fact, but I think we've known each other long enough that you're not going to get freaked just because I level with you. You remember how I said in my last letter I was getting really damn horny without a guy around? Um, yeah, problem solved there. In a really fucking unexpected way, but problem most definitely solved.

Which is a good thing, because the problem definitely got worse before it got better. Spending all my time wandering around in skimpy bikinis or lingerie, with nothing really to do but have fun...I didn't have anything to do to take my mind off of how horny I was. I'd slip off to the bathroom, take a long hot bath and listen to my MP3 player while I frigged off, and then twenty minutes later I wanted more sex. At one point, Andrea was giving me a massage, and it felt so good I wound up whimpering a little and rubbing myself off against the table. Which wouldn't have been so bad, except that I also found my legs spreading apart all by themselves and my butt lifting up like I was in heat and there was a huge damp spot on the towel underneath me. (Andrea acted like it was no big deal, but I heard her muttering something under my music for the rest of the massage. Admittedly, she's always muttering something under my music--I've gotten to the point where I just tune it out--but I could swear I heard something about "horny little bitch" in there.)

So here I am, getting non-stop horny to the point where I can't think straight (and I'm sorry, but I still haven't figured out how to work the email or the phones--I just always seem to get distracted.) And there we were, going out clubbing every night, and Cammie just always seemed to have an endless supply of those pills that make me all fuzzy and horny, but she was always really careful not to let the guys get too close, and finally a couple of nights ago I was so wound up I was just about ready to pop. I made up my mind (what there was of it--I keep meaning to ask Cammie what's in those pills) that I was going to find the first cute guy I saw and drag him off somewhere to have sex with him.

So I got out on the dance floor, and there was this nice-looking guy out there--dark hair, smoldering eyes, sort of like a young Antonio Banderas, and my libido said, "WANT!" And I sort of drifted over to him, and he smiled at me with this look that said he totally knew exactly what I wanted and how bad I wanted it. It was a smile that said, "I can get away with making you beg." And he was right, too. I would have begged to fuck him. I would have let him do anything. (It's a good thing you're my unshockable friend, because you can probably tell that this letter is heading into "fuck and tell" territory.)

So I danced with him a little, and he didn't say anything and I didn't say anything but the bump and grind we were doing said everything our mouths didn't, and I could feel him getting hard inside his pants. Hell, his pants were so tight that I could see him getting hard inside his pants, and he looked like he had enough down there to make me very happy. I could feel my panties getting damp just thinking about it...

Report Story

byJukeboxEMCSA© 5 comments/ 14696 views/ 3 favorites

Share the love

Report a Bug

Next
2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel