I just graduated.... thank all. The horrendous loads of studying,homework,and money going into my degree was finally over. I had not dated in many months and then when I did it was short lived with me constantly preoccupied with my scholastic life. Now I had time for fun. While at home one evening, I come across a banner on a "site" that visit regularly that advertised you could win a weekend with a pornstar. Strictly curious I click on it and was surprised it was not as it sounded. It was guidance on a variety of different things to help make you a star in your life. Hmmmmm is the only thing that crosses my mind. I could use a little vamping. I'm not exactly plain by any means, but somehow attracting a different kind of guy and learning how to keep up with him for a bit was an extremely tempting and just enticing to the fullest. As I go through the page, it describes what the whole package includes: "pick from our 10 male stars, or 10 female stars and get a makeover!" 10 people to choose from, an allowance to shop for anything, a weekend at a villa in a secret location,and anything they see fit (except medical). I sign up just for a little kick and then commence with checking my mail and clowning around.
I start to yawn and decide to go through my normal little bedtime routine. Slipping into bed, I started thinking about if I win that contest what would happen and I start laughing and blushing a little sitting there shopping for huge stilettos with some chick and guys drooling then commenting on her "acting abilities" and what I have been in. It was comical yet a bit eerie to mull over. Falling asleep helps me forget about winning a contest I knew I never would and just enjoy the night with no dreams. I wake up at noon and fix a little something for lunch while once again, flopping in my chair to squander hours relaxing on my pc. Password,wait,pull up browser,type shit in,go to some sites, finish eating,go to mail and.... I see an email from the contest. "Of course it's just a thank you for entering message" I think. As I open it, I start reading and realize that I won. I won? I won? I WON! It wasn't Publisher's Clearing House or anything, but it was the reward for being uptight and future minded in high school and college. Only one of my best girlfriends really knew what was going on, the rest of my friends and definitely family just knew I won a vacation. I get my arrangements and find out that my entire weekend is in the Virgin Islands! Oh my what to take.... I decide a new bathing suit needs to be purchased, shoes,and of course plenty of sunscreen.
The day of my flight I hop on the plane and just sit there with my purse listening to the chatter and dribble of the flight attendants waiting for takeoff when I finally hear the captain's voice chime in we will be taxing in five minutes. At the last minute a very attractive man sat next to me and gave me a smirk. I attempted conversation, but I received nothing but him giving one of those little looks my dog gives me whenever I start talking to him where he just cocks his head a little to the side and looks at me like a piece of modern art. I just smirk back and lay my head into the comfy rest and just nap my way through the whine and turbulance of the ride.
After hours of being numb and stiff, we file out of the plane and stretch making my way to the luggage carousel. I manage to get mine, then walk a little while to a pick up point as someone taps my shoulder asking me my name. Hesitantly I answer and he says "ah yes good good.... I was given a brief description." He takes my luggage and tosses is with ease into the back of a beautiful Cadillac with leather interior and wood panels. I scoot in and he shuts the door beside me, climbs in, ans we are off to the villa. The ride is amazing with the locals in their colorful clothes walking across the very plain grey road. There are birds flitting and swooping about as they settle in for the evening that I watch while talking to my driver. As we pull up the winding drive I see the building coming up. It has some very simple but privacy keeping landscape with a few lights on. I head up the stairs and make my way through the large carved door and see two chefs, a maid, and my hostess Anna there to greet me. I shake hands and chat learning the layout of the place while heading off to my room. It is magnificent! It is red with birds painted on the wall and a white bed and matching setee. The dressers and nightstands are a dark wood breaking up the room a little. I am left to unpack and then head back downstairs. Dinner is waiting on the veranda outside while we all sit with some wine and our gourmet dish; nothing a recognize which is obviously a local delicacy. We dine and go over the weekend: shopping, lunch here and there, then a get together Saturday night with a few of Anna's good friends. I worry about being around all of those skimpy overdone barbies. Oh well, time to settle in.
The night seemed to fly by as I wake up, get dressed and go out. We both go to a few shops with nothing exciting except for a few pieces of jewelry and some shoes. After a quick lunch, we walk around for a while and head back. The day seemed to also go by too quickly but, what can you do about it? We get dressed in our hottest dresses she in a little mini blue thing with everything hanging out and a large necklace going all down her chest to her navel. My dress was black and with wider straps just covering my bra. My bra was another story under my sexy yet still classy dress. It matched my thong which was black see through mesh with red outlined lace and tiny diamonds that Anna picked out and I somehow found cute. My hair and makeup were stunning too. I go to the little living room and meet everyone. There are no other women to be found, just four men. They are the model types with short hair, muscles everywhere and nice suits the shirt exposing their chest. The music gets into Anna and they all get up to dance. One of them pulls me off of the sofa in one swift jerk and flings me into him. There wasn't a bit of space between any part of us and our salsa. A few twirls broke that up. I feel another one of them come up behind me and start rubbing his hands up and down my thighs then press against me. They are grinding with me up and down while starting to put their hands into my dress periodically. I am a bit nervous, but I am enjoying this too much. Anna and her two are already half stripped and she alternates kissing the two.
They make their way to the couch and continue their groping. I am still sandwhiched feeling them growing while we go to the same extra long sofa and sit. The one in front of me shoves his large tongue down my throat while he and the one behind me take their suits off and get down to their boxers. I rub my hands all over him and make my way to his large bald head peeking out of the flap. He then grabs my hips and leads me to the ottoman. I lay down on my stomach and take it in my mouth. He puts the straps down while the other man unzips me. He then grabs my boobs and massages his hands into the bra. I feel hands on my ass and the thong pushed to one side while another head goes in about two inches. I moan and he starts fingering my clit at a medium pace. I love having two in me at the same time, a first for me. I feel him lean into me ear and say "come on baby drench me.... squeeze my dick!" Just the feeling of a head that filling with his fingering was fantastic. He rubbed making me clench and I would hear him moan and go faster. I yell to him "more! give me more!" "Oh you want more? you're going to have to earn it by getting soaked!" I finish off the now completely stiff cock in my mouth and he moves over to the otttoman and sits down keeping his hard up until it is needed again. I have another three inches shoved in and he fingers me so fast and speeds up his pounding until I bite my lip and spread my legs apart further for every bit I can get. He shoves them together and goes full in. I cum and hear him sigh then take a deep breath and go all in. He recklessly rams me over and over causing my back to arch and my head goes back far enough for him to grab it and hold it keeping my eyes up at the ceiling. I then see anna crawling over to me and her huge tit goes down and one of the other guys puts her nip in my mouth. I think how fascinated these guys are with them and dismiss the thought. I never thought about a woman sexually but this is kind of fun. I grab and play with them for some time while sucking and being pushed into those silicone pillows and hold on to them tight as a raging orgasm builds. I let go and he pulls out as they reposition me. One of them picks me up with little effort ans lets me fall onto him as the other slowly squeezes into my ass. Then comes the ride of my life. My ass is gently fucked while my pussy once again is pounded. I start shouting yes yes yes! and then cum again and they keep the rhythm going to get it all out. They set me down and shoot all over the sofa. I am barely able to breathe as I get over my various partners and nearly an hour of vigorous fucking.