Dream Vacation

(NOTE) The women in this story are based in appearance on some of my favorite porn stars, as follows:

TRINA portrayed by TAYLOR HAYES

As my daily Escorts...

Day one, CANDI - Jenna Jameson

Day two, KATIANA - Tera Patrick

Day three, NATALYA - Veronika Zemanova

Day four, BIANCA - Bonita Saint

JUSTINE - Justine Joli

Day five, MONIQUE – Ashton Moore

Day six, AKIMI and KIKO – Felicia Tang

Day seven, JULIE – Julia Hayes

Day eight, NIKITA – Chloe Vevrier

EVELYN – Taylor Wane

STACI – Taylor Francis

SUSIE Q – Levena Holmes

Other Escorts and Strippers...

Escort, DANIELLE - Nikki Dial

Escort, LEXUS – Sandy

Stripper, CHARLA - Celeste

Stripper, SANDI - Jenna Haze

Stripper, DELILAH - SaRenna Lee

Stripper, VICTORIA – Zdenka

MY WIFE - Herself

The Hostess, SAMANTHA – Use your imagination

While the policies of Literotica prevent me from offering links, images of any and all of these ladies can be easily found via your search engine of choice (with the exception of my wife – but she resembles Helena Bonham-Carter, for those who want a visual). In some cases, the appearance of the ladies has been somewhat idealized from those who supplied their inspiration, so no jumping down my throat about Julia Hayes being shorter than six feet in real life! J

===== DAY ONE =====

It was a string of unlikely events that all came together which ultimately allowed me to spend a week in the kind of paradise I never would have thought possible. It started with a scratch ticket that won me a sudden windfall of twenty thousand dollars. I wasn't sure at the time what made me hide it from my wife, but in the end... well, let's just say that there was a reason, it was a good one, and it worked out seriously well for me.

I converted the winnings to cash and placed it in a safe-deposit box, feeling a little guilty about hiding such a large amount of money from my wife but unable to resist the sheer self-indulgence of it. I thought about using it to finance my sexual flings outside our marriage, but the idea of juicing it down the drain of so many strip clubs and massage parlors seemed rather small-minded, and besides, I couldn't do it that often or I'd eventually get caught.

What I really wanted to do was try the sexual adventure of an erotic vacation package, the kind I'd read about on the web. A week under the Caribbean sun with a beautiful and sexy woman ready to cater to my desires sounded like more fun than mortal man deserved, especially if I shelled out for a second woman. I even had my package all picked out with an outfit called Fantasy Vacations, and sometimes I'd go online to look at their women and wonder what it would be like. Now I had the means, but not the opportunity, as there was no way I could get away from the wife for that long.

Then lucky chance number two fell into my lap.

My wife greeted me at the front door one day when I came home from work and gave me some startling news. It seemed that her women's group was organizing a fourteen-day trip to a cabin one of them owned in Colorado, and she wanted very much to go but, of course, we didn't have the money for airfare or other expenses. I thought quickly, and told her to pack her bags because I'd just won a thousand dollars on a scratch ticket and had been waiting for her birthday to surprise her...

Well, I got a lot more thanks than a lying bastard like me deserves.

So my wife would be out of touch for two weeks without even a phone, and I had that time to indulge myself. I immediately made arrangements to take the time off work, explaining that I wanted to take a week-long class (I told my wife the same lie, and to make it as real as possible I actually signed up for such a class - it offered internet lessons, so with luck I'd actually be able to study and complete it). I then took advantage of an evening when my wife went to bed early, got online, and with a lump in my throat and a cock hard with anticipation prepared to actually book the vacation of my dreams. After two hours and a deposit off a credit card my wife knew nothing about, I was all set.

The next month crawled by until the day my wife left town, thanking me profusely once again for letting her have this time with her friends and promising to try and call me if she made it to a phone at some point, but I reminded her that I wouldn't be able to answer my phone in class so she would probably just have to leave a message. Once she was gone, I raced home to make preparations to leave the next day.

I got very little sleep that night!

===== DAY ONE =====

The next morning I hit the ground running, took a cab to the airport, and soon found myself flying out over the Gulf of Mexico. The package I had selected included five nights at the resort and another three on a cruise ship, with the result that I'd be getting back home a full day before my wife. I had chosen the double-escort deal, which allowed me to choose one woman as my main companion, and then on each night I could select someone to join us. The deal was that the women themselves would provide full service, and that my primary companion would be with me for the duration of the trip with two hours off out of each twenty-four. Of course, I wouldn't have the resort to myself - there would be other customers there as well. I felt a little weird about the idea of living my fantasies with strange men around, but I figured we were all there for the same thing and that certainly no one would judge me.

Once we landed, I was greeted by a chauffeur who loaded up my bags into a stretch limousine and drove me to my first stop on my vacation, the reception hall where I would meet my potential ladies. As I had paid for the first-class treatment, I would be able to take my time and select my companion from about a dozen available women, while those who elected for cheaper packages would meet them as a group at the resort itself (except, of course, for the ones I chose for my first night!). The anticipation made me positively giddy, and as the beauty of the island swept past the windows of the car, I saw none of it but instead imagined what lay in store for me in my greatest sexual adventure yet to come.

After a short forever, the limousine pulled up to the front door of a fine hotel and I was let out. The driver told me that he would take my bags on ahead to the resort, and I tipped him generously (not only was I in a good mood, but I wanted to be on excellent terms with all the staff). I was met at the door by a good-looking fortyish woman in a lady's tuxedo.

"Good morning, sir," she said warmly. "Welcome to the Caribbean! I trust your flight in was comfortable?"

"Very much, thank you," I said.

"Please, let me show you inside," she said, offering to take my arm. "My name is Samantha, and I'm in charge of companion services for Fantasy Vacations. It will be my pleasure to introduce you to the ladies who will give you the best vacation of your life. We think it's very important for you to meet our girls and get to know them face-to-face before making such an important decision, because there's so much you just can't get from a photograph. After an hour or so, we'll be ready for your decision. Now, since you're here on the VIP package, you can also choose your second companion for the first night."

"Are all the women willing to... provide full service with another woman?" I asked.

"Yes, but of course not all of them have the same degree of experience with that sort of thing. If it's important to you that they be totally comfortable with that, then that's one of the things you'll want to ask them and it's one of the reasons why we have you come and meet our girls before making your choice."

While we had been talking, Samantha had led me across the lobby to the elevators, and we rode up a level and proceeded down a hall. We finally came to a door where I could hear several women's voices talking and laughing together.

"Are you ready?" Samantha asked with a smile.

"As I'll ever be," I replied gamely.

She opened the door.

I walked with her into a room with about a dozen women all standing or sitting enjoying drinks, and as we entered they all turned my way and smiled, calling out greetings as if I were the life of the party who had finally arrived. I found myself suddenly surrounded by ten or twelve very pretty ladies, wearing a variety of sexy party dresses.

Samantha raised up her hand to get everyone's attention. "Ladies, this is our guest of honor, Xavier," she said, giving the alias I had adopted. "Now, we've only got an hour for him to get to know you all and decide who he wants to choose as his companion for the next week, so please let's give him a chance to meet everyone. Xavier, let me offer you a drink."

"Peppermint Schnapps, neat," I said, grateful for the offer as my system needed a shot of something. Pretty and sexy women don't usually make me nervous; I've had jobs with some real hotties for co-workers, and I can always talk to them just like everyone else. However, when the objective is to get physical, I tend to become very shy and awkward. I'm lousy at "picking someone up" and the odd thing is that the more likely I am to actually get some action, the worse it gets. In this case, every woman in the room with me was a sure thing, and I had a serious case of the shakes over the idea.

"Hi, I'm Danielle," said the slim brunette who happened to be closest to me. "Welcome to the Islands, sweetie."

"I'm Bianca," said a Latina beauty to my left. "I

love

to party, if that's what you came for."

"Hello, Xavier. My name is Lexus." This greeting came from a sultry blonde who gazed upon me with slightly narrowed eyes and a seductive smile.

Over the next half hour I met everyone in the room and chatted with each woman, getting a sample of each personality and an idea of what spending time with them would be like. I felt oddly like I was at a buffet or even an auction, where I had to make an impossible choice from so many opportunities. The idea that I would be able to sample a number of other women by the time my trip was done helped ease the stress a bit, but it was still a tough decision.

My eyes kept returning to a finely sculpted brunette who had greeted me only briefly but who continuously sent me little flirts from across the room. A smile, a wink, a lick of her lips, a feathery stroke across one of her breasts... she never came closer than ten feet and never said a word beyond her first hello, but she enticed me. The allure was all the greater because she was truly a stunning woman, ordinarily far out of my league. I decided to take her up on her unspoken invitation.

"I can't help but think you're trying to get my attention," I said as I approached her.

"Was I giving you that impression?" she asked with a playful smile. She had wide eyes of deep brown, deliciously pouty lips, and model-perfect cheekbones.

"Can we talk together for a moment?"

"I was hoping you might say that," she purred, and we sat down together on the sofa.

"Trina, wasn't it?"

"Mm-hm." She scooted closer to me, until we were definitely sharing personal space. "So, have I indeed caught your attention?"

"I'd say so," I replied, more than a little taken off guard.

"I like a discerning man," she said. "One who seeks out what he wants instead of letting it come to him. That's why I prefer a more subtle approach... at first." She put her hand on my thigh and rubbed it in tiny circles.

"So, what else do you prefer?" I asked, trying to maintain composure in the face of an absolutely beautiful woman blatantly coming on to me. "I'd like to know that we're, shall we say, compatible."

"I can be very open to ideas," she said.

"Do you like... other women?"

She actually seemed to brighten further at the prospect. "I think making love with a woman can be

very

exciting," she said. "That's one reason I hope you pick me, so I can share a different woman with you every night you're here. I can even help you find the best ones."

I took a moment to look over her body. She had a nice, firm rack of D-cups, a slim waist, and long deep-tan legs. "I'm beginning to think you can find the best one by looking in a mirror," I said.

She smiled wider. "You're very sweet. But tell me what else you like, I want to know."

For the next ten minutes, we talked about my turn-ons and such, and I was pleased to find that she was willing and even seemed excited about everything I wanted. I figured I had found my girl for the week, but there was one more matter to check.

"How do you feel about deep tongue kissing?" I asked.

"Let me show you," she whispered, and moved in for the kiss.

Her tongue touched my lips first and parted them by thrusting inside my mouth, and then warm and soft lips followed as she kissed me with deep fervor and passion. With arms around me she slid up onto my lap, and as I felt her soft body next to me I knew she was definitely the one.

"That's how I feel," she whispered through lips that still touched me. "Do you like the way I feel?"

This was going to be a great vacation.

* * * * *

For my first night on the Island, I decided I wanted to get to know Trina a little better and figure out for certain that she was the woman I wanted; I was allowed to switch if I chose, and though I couldn't imagine finding someone else who would turn me on more, there was always the possibility. Of course, I was also entitled to a second companion. We would have our opportunity to select one at the reception party for all the guests.

Trina wore a rose corsage on her wrist, indicating that she had already been "claimed", and carried a second one for whomever I chose as my other companion for the night. We strolled around and mingled while the other guests made their rounds and found the ladies they wanted. I suppose it was only natural that I found myself wishing I was the only man there, feeling a little self-conscious about living my fantasy with an audience, as it were. Trina picked up on my nervousness and her experience told her what the problem was before I even needed to explain.

"Really, it's no big deal," she said soothingly. "Especially as it's your first time here, I'd be surprised if you didn't feel a little self-conscious. Believe me, you'll get over it soon enough. And if you'd rather be more private with our... intimate activities," she said with a smile, "we can certainly be accommodating. We just want you to relax and have a good time. Think of me as your girlfriend, even as your wife if you like."

I couldn't help for a moment but think of my wife and what she would think of me in a place like this, and I didn't have any illusions about it; if she knew, I'd be served with divorce papers within the week. Ever since I had started giving myself these little sexual joyrides with strippers, escorts, and the like, I'd been taking it a little further each time until there was no euphemism for what I was doing any more. This wasn't a case of satisfying a harmless curiosity or indulging in a natural male drive. This was cheating, no bones about it. I wasn't so callous that I didn't feel guilty about it, but on the other hand, exactly how much sexual frustration was I just supposed to swallow and deal with? I wasn't a pervert for wanting to have sex, and if my wife refused to provide it, then I could either suffer, force her, or find it someplace else. I'd had enough of suffering, and the second option was completely unacceptable to me or any other man with a shred of decency. If she was going to compel me to seek sex outside our marriage then so be it, and along the way I would indulge in a few fantasies like a threesome with two women.

Actually, there was a married couple there at the resort. Their names were Ted and Jean, and they were apparently frequent visitors. I felt a pang of jealousy that I didn't have a wife who would even have sex with me more than once a month, let alone coming to a place like this and inviting another woman into our bed. Certainly that wasn't the sort of thing that I expected from my wife, but for God's sake, she didn't even like kissing me with tongue!

Trina caught my long silence and interpreted it correctly. "You're worried about what your wife would think of you, aren't you?" she asked.

I nodded. "I'm here without her knowledge, of course. It's a long story, but suffice it to say that I don't get much attention at home. God knows I've tried."

"Come here for a moment," she said. "We need to talk alone for a bit, I think. I don't want this hanging over your head for your whole trip, or you'll never be able to relax and have fun."

The two of us went off to a quiet corner of the room and sat down on a small love seat behind a palm, mostly hidden from the rest of the party. I had noticed that the room had several little nooks like this, and assumed that they were used for quiet sexual interludes away from the crowd.

Once there, I gave her a short version of my wife's lack of sexual passion and the strain it put on our relationship, and how I had started to seek out satisfaction on my own terms when it became clear to me that she would never provide it. I knew that I was pouring my heart out to a hired whore and that in return she would tell me exactly what I wanted to hear, but it still felt good to get it off my chest.

"Listen, sweetie," she said, laying a hand on my knee, "you're a young, strong, and very sexy man. You deserve to satisfy your needs, and any woman you offer yourself to should be flattered. And before you think I'm saying that just because I'm getting paid, remember that I could have waited in the background and let you pick someone else. I desired you, and so I gave you my best moves. You're a really hot man and you turn me on, and I can't wait to feel you inside me."

"Think you could get my wife to see along those lines?" I asked.

"Oh, if you could bring her down here, I'd be happy to show her how much she's missing out on. Maybe I could even teach her a thing or two about how to please you?" She licked her lips seductively.

"I wish it were possible," I shrugged. "But hey, I have a hard enough time talking her into getting it on with me, let alone another woman."

"You shouldn't have to talk her into anything. She should be happy to make love to you, excited about it. I know I am."

I wasn't sure what to say. She was dishing out flattery and cheap praise, like I'd expected, but mixed in with that was a certain amount of truth. I had tried so hard to entice my wife into bed, give her what she wanted, get her to enjoy sex and intimacy, and had it all come to nothing. Why should it be such a one-way street? Who was making me happy, giving me my pleasure, and satisfying my natural desires?

The answer, for the next week, was sitting beside me, waiting and willing. The fact that she was willing, even if only because it was her job, gave me a stir of excitement and need.

"Let me be the lover you crave," she whispered as she moved in for a kiss. "Satisfy your desires with me."

Her tongue entered my mouth again and I felt her firm breasts press into my body. She took my hands and gently guided them down her own lovely curves, past her tits and over her slim waist, onto her round bottom that her dress only barely covered. We sucked at each other's tongues for a long moment, and when I moved my hands up under her dress she encouraged me to go further. Her inviting, uninhibited attitude turned me on even more than her sculpted body or her soft, luscious lips.

"I'm going to give you what you need right now," she whispered. Breaking away from the kiss, she held me with her eyes on mine while she slid down my body and, without ever looking away or down, unbuttoned my pants and opened the fly. My cock, which had grown rock-hard from her attentions, came free and rose up to meet her lips.