Sister - Escort

This is a work of fiction; any resemblance to real people, living or dead, or to actual events is purely coincidental. All characters involved in any sexual activity are over the age of 18. I hope you enjoy this story. Constructive criticism is always welcome.

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I was preparing for my first vacation in 10 years. I had been building my own company and it seemed to finally be on solid footing.

After graduating from Case-Western University with a degree in computer science and getting my masters at Wharton, I had worked on an idea that had been germinating for quite a while. I sold the idea to some venture capital guys, giving them a 1/3 share of the company for startup capital.

I licensed the best voice recognition software that I could find, and the best voice synthesis software. I combined those with some artificial intelligence and database software to create the best front-end for call centers. The AI reviews thousands or millions of recorded calls, it identifies 99% of the topics that people call about and provides custom answers to customers' questions. It saves companies that have large volumes of incoming calls millions!

Now that I have the software integrated and have a sales force, I have finally decided to take a few days off! Some friends from college and some business associates rented a sailing yacht.

This was planned to be a week of 'clothing optional' fun and sun. The other guys were either married or seriously dating someone, but I had been working 100+ hour weeks for the last many years and that hadn't allowed me time for a social life. There was a modeling agency in town which also would provide escort services. I had used them when I was attending social events where a companion was needed, and I had scheduled a 'full service' companion for the week.

I had not met the young woman, but had left it in the hands of the agency. I had arranged for a first-class ticket to be delivered to the agency along with the general plan for the week, suggesting that bikinis and sun dresses would be adequate attire.

I was running close on time as I reached the boarding gate. In fact, they closed the doors immediately after I entered the plane. I walked into first class, gave my carry-on to the attendant and slipped into my seat.

I turned to introduce myself to my date for the week as the plane began to push away from the terminal. I nearly shit myself! Sitting in the seat beside me was my younger sister!

"What are you doing HERE?" I exclaimed. On one level, I knew what she was doing. She was working on a modeling and acting career, so...

"Hello, Matthew! It's so good to see you again."

We had last seen each other at our parents wedding anniversary several months before. I sputtered, "But what are you DOING HERE?"

"I believe that you contracted with my agency for a companion for the coming week. Right? I am going to be that companion."

"But...." I mumbled.

"You are my big brother, my big successful brother. And I am going to be your companion. We will have SO MUCH FUN!"

"But I can't.... We can't.... I mean...."

"You may introduce me to your friends by professional name, Bethany Stone. They need not know that we have any relationship except a dating relationship. And I think that this is going to be FUN!" She added, "Did you know that I had a huge crush on you when we were growing up? Now I have you all to myself for a whole week!"

I considered the situation. I could send Beth back on the next flight and go sailing without a companion. It would be awkward with me being the only person without a companion, and the cruise was specifically intended as clothing optional. Every lady would feel like I was perving on them. It would be uncomfortable for everyone.

Or I could have Beth join me on the cruise. She would have a good vacation; we could enjoy a pleasant week together and platonically share a cabin. We could do that. It wouldn't create a disturbance for the guests. We could make this work!

"OK." I said. "We can make this work. I don't love it, but we can make it work."

"You're a smart guy, I knew that you would see that, given a little time and encouragement!"

The stewardess came by offering drinks. I asked for a double bourbon on the rocks, Bethany asked for a glass of champagne. We talked and talked, catching up on parts of our lives that would never come up at dinner with our parents. As we talked, I realize what a beautiful woman my sister had become. She had long, shapely legs peering out of a slit in her skirt that extended well up her thigh. And she had breasts that nicely filled her silk blouse despite the obvious fact that they were unsupported by a bra.

An objective appraisal would say that she was a beautiful woman. She certainly was no longer the awkward 15 year old girl she had been when I left for college. She was HOT! And she certainly was not the conservative woman who appeared at the occasional dinner with our parents!

I ordered another round of drinks for us. I asked, "Are you really up for a clothing optional week with me, my friends and associates?"

"Each of them is bringing a companion, right?" I nodded. "So I could spend a week naked with YOU?"

"And seven other couples." I clarified.

"This is WAY BETTER than my best teenage fantasy!" She paused then continued, "Do you know that in my very first orgasm I was fantasizing about being with you?"

I didn't know what to say.

"And you were my primary dream lover until I was out of college." I simply shook my head.

"So when I saw your request on the manager's desk, I volunteered for the assignment. I don't usually do escort assignments, so my manager was a little surprised, but I assured her that I really did want the assignment and that I was certain that the client would be pleased!"

"So this isn't a simple quirk of fate? You actually engineered this?"

Beth nodded, shyly. "I hope that I didn't screw things up," she said tentatively.

"I don't know what to say! So you actually volunteered for this assignment? Knowing that I was the client? And knowing that it was planned to be a clothing optional outing? Where everyone, including you, would be nude most of the time?" Bethany nodded to each of those questions.

"And you were aware that we would be sharing a cabin with a queen sized bed?"

"I expected that the bed would be smaller than that!"

"You were expecting to be sharing a bed with me?"

She looked at me from beneath her eye lashes and nodded.

I pulled her toward me and placed a kiss on her lips. She leaned into the kiss, and soon I felt her tongue teasing my lips. I took her hand in mine and we snuggled together in our seats and finished our drinks. Before long the plane was descending into the Miami airport.

After reaching the terminal we retrieved our carry-on bags and headed to the cab stand. Soon we were approaching the docks where we would find our sailboat.

Bethany and I stowed our bags and returned above deck to greet our other boat mates. Wine was opened and poured as others returned to the deck. As the boat motored out of the harbor, several couples returned to their rooms to change clothes. Swimsuits, bikinis, and open weave tops began to appear on deck. Drinks were flowing freely until the chef asked that everyone help set up the dining tables and be seated.

As we were seated introductions were repeated. Several couples were relatively young married couples; others had been dating for months or years. I introduced Bethany as a long-time friend. Everyone was welcoming and it was clear that several men enjoyed looking at her.

The sun was setting over the Caribbean as dessert was served. We wandered around the deck, watching stars appear one by one. I stood with my arms around Bethany. I said, "I was concerned about having you here. After all, you ARE my sister! But you have been so good with all of the other guests, and it is so very comfortable being with you."

Beth turned toward me, wrapped her arms around my neck, and kissed me warmly. I could feel her large breasts rubbing against my chest. Without thinking, I gripped her buttocks, pulling her firmly against me. Our kisses became more passionate, and then I was kissing down along her neck and throat.

Bethany took my hand and led me to our cabin. There she pulled off my shirt and pulled down my swim trunks. With me naked, she pressed against my chest until I sat on the bed and reclined. Then she slowly and sensuously began to remove the open weave cover up she was wearing.

She faced away from me as the top exposed her perfectly sculpted buttocks, encased in thin, form fitting nylon. The suit was not the most revealing thing I had ever seen, but it was extremely enticing, and the top of cleft between her butt cheeks was clearly visible. She turned to the side as she pulled the top higher and higher. Her flat stomach was visible in profile, but her breasts were obscured by her arms as she lifted her top higher. When she tossed the top away, the profile of her breasts took my breath away!

Bethany turned to face me and smiled. A look of awe was plastered on my face! "You're BEAUTIFUL!" I exclaimed.

"Why, thank you, kind sir! But there is more to come!"

My little sister reached behind her neck and pulled the string, then pulled the string across her back. One hand held the scraps of material that covered her breasts. I was holding my breath, waiting for her to reveal her beautiful breasts to my hungry stare. Then she slowly moved her arm until the fabric dropped to the floor. Never had I seen more perfect breasts than hers! They were large and firm, shaped more like a bullet than a ski slope, with smallish sized areolae and long, erect nipples. My mouth drooled to suck on them.

Finally, she released the strings on each hip. She shook her hips and the fabric dropped to the floor. Her pubic hair was trimmed to allow all but the most daring bottoms, and her pussy lips were completely shaved.

Bethany trailed her fingers along the inside of my leg and up my thigh. Then she slowly traced along the length of my rigidly erect manhood. My cock twitched at the contact; my eyes were glued to her beautiful nude body.

I watched Bethany as she climbed onto the bed and straddled my waist. She allowed her nipples to drag along my chest. Then she dropped one breast into my mouth. I sucked her nipple into my mouth, latching onto the nipple and suckling hungrily at her delicious breast.

She pulled back slightly and allowed her other breast to fill my mouth. I was deliriously happy as I reveled in the fullness of her breasts and her large, erect nipples!

Bethany kissed my forehead and pulled away, much to my dismay. She kissed her way down my body until she reached my pubic area. There she grasped my dripping erection and gently pumped the shaft up and down.

Her mouth hovered over the head of my cock. I nearly shook with need as I anticipated the moment when she would engulf my cock in her warm mouth. She kissed the crown of my penis and licked on it like an ice cream cone. She looked up at me and said, "You don't know how many times I have imagined this!" Then she took the head of my cock into her mouth!

My hips lurched upwards! I moaned! I have never experienced such a beautiful sensation! I could feel my sister purring as she held my penis in her mouth!

Then she began to move up and down on my cock, sucking and swirling her tongue around the sensitive head and pumping her hand on my shaft. It had been a long time since I had last had sex, and a far longer time since I had experienced anything even remotely as erotic as this.

In only minutes my hips were pumping up into my sister's mouth. Her tongue swirled, her mouth bobbed, and her hand pumped on my cock. "Beth! I'm going to...."

She redoubled her efforts and I began to blast load after load of my semen into her mouth. She sucked and swallowed, sucked and swallowed as I pumped my semen into her mouth and down her throat. It seemed that I had an endless supply of semen to pour into her mouth, and she was swallowing every drop!

She climbed up beside me; I couldn't move. My entire body had been reduced to mush. Beth snuggled next to me and pressed her large breasts against my side. She wrapped an arm and a leg over me as she nuzzled and kissed my neck and cheek. Moments before, I would have sworn that I could never move again, but soon I was kissing her back.

Passion built and soon I was kissing down along her neck and throat. I continued down across her chest and onto her breasts and nipples, enjoying the soft fullness of her breasts and the rigid points of her nipples.

I placed her hands above her head and against the headboard, instructing her to keep them there. I kissed the full roundness of the sides of her breasts, placing erotic, tickling kisses up and down each side.

Then I continued down her body. I kissed over her flat abdomen and to the fringe of her neatly trimmed pubic hair. I reveled in the musky aroma of my sister's sex.

I kissed down the valley between her leg and her body, continuing along her leg and down to her knees. I kissed, caressed, and sucked on the sensitive flesh behind each knee before tracing a leisurely path up the inside of each thigh.

As I moved higher and higher along the insides of her thighs, Bethany began to squirm and gently pump her hips. As I approached the seat of her sex, my little sister was moaning softly and pumping her hips more vigorously.

I traced my tongue along the edge of her pussy lips on one side then the other. She twisted her hips and lurched upwards, trying to increase my contact with her sex.

When I traced my tongue along the opening of her dripping sex, she moaned loudly and pumped her hips up to greet my mouth and tongue. But she kept her hands touching the headboard as I had instructed.

My tongue dipped into her wet slit again and again, each time pressing slightly deeper between the lips of her pussy, each time gathering more and more of her delicious nectar. Bethany's hips were pumping up to meet me on every stroke. Then I flicked her clitoris with the tip of my tongue. She screamed!

I lay on my stomach, my arms encircling her hips so that I could reach her breasts, caressing her nipples as I lapped at her delicious pussy. Every stroke ended with a little flick of my tongue on her clitoris. My little sister was moaning and begging for me to make her CUM! "GIVE ME YOUR COCK! MAKE ME CUM! MAKE ME CUM AND CUM AND CUM AND CUUUMMMM!!!"

I began to concentrate on her distended clitoris, licking it and swirling my tongue around her sensitive little nub. Beth was nearly beside herself with sexual need. I brought one hand down and gently inserted a finger into her surprisingly tight pussy. Then I sucked her clitoris into my mouth while tugging on her nipple and caressing her G-spot.

Her hips lurched upwards frantically, forming a rainbow arch of her body and I felt her fluids spraying my face! I stroked my little sister's G-spot, sucked on her clitoris, and tugged on her one nipple as her body repeatedly lurched against my face. She was bucking wildly. Forgotten was the instruction to hold onto the headboard, she was gripping my head and pulling me even tighter to her spasming pussy.

She bounced and thrust as her body was consumed with orgasmic contractions. Then I quickly shifted position, lifting her legs onto my arms as I pointed my cock towards the spasming entrance to her womanhood. I thrust forward, filling her with my engorged cock. She screamed in delight.

I pumped my cock into my little sister's tight vagina again and again as it spasmed around me with ongoing contractions. Her pelvis was tipped up with her legs resting on my arms, my manhood rubbed against her G-spot with every thrust. Bethany's orgasms were unceasing; they piled one on top of the next as they crashed through her body.

I had climaxed recently, but the response of my little sister's body to my sexual onslaught was pushing my arousal higher and higher. I drove my cock faster and deeper into Bethany's welcoming body. Perspiration was dripping onto her beautiful bouncing breasts. I was possessed with a need to satisfy this woman in a way I had never experienced before.

My hips were flashing in and out of Bethany's pussy. I was like a runaway freight train roaring along the tracks. Nothing would slow me down! Nothing could stop me as my passion rose higher and higher. My need built to explosive proportions. I was going to explode!

Suddenly, I was shooting my lava hot semen into my little sister's depths. Blast after blast, load after load erupted into Bethany's core, spraying the door to her womb with powerful blasts of my semen. I couldn't stop! I was spewing my life force into my little sister again and again and again. I poured more and more of myself deep within her until I had nothing more to give. Then I collapsed onto her heaving breasts.

We lay together for a long time. I could feel aftershocks from her massive climaxes as they rippled through her body. I tried to move to one side to relieve my weight, but Bethany held me firmly in place. Finally I log-rolled the two of us so that she would be on top, but my cock could remain firmly entrenched in her pussy.

Bethany kissed me again and again, covering my face with her kisses. I felt tears dripping onto my face, but they were obviously tears of joy. Then she was murmuring, "Thank you! Thank you! Thank you!" over and over to me, while I felt that I should have been thanking her!

We rested, we kissed. Finally we talked. Bethany said that she had wanted, dreamed about, hoped for this ever since before she even really understood what sex was. Now, we were together and it was even better than anything she had imagined. She said that all of her previous sexual encounters were mere shadows of what she had experienced with me.

While I had never fantasized about my little sister, I had to agree that this was by far the best sex I had ever had. I asked Bethany, "What happens now?"

She asked, "Will couples be having sex on deck?"

"I wouldn't be surprised," I responded.

"I want to have sex with you in every place and in every way possible! I want to wear that noble member down to a nub, and then suck it back to its full, robust condition so that I can ride it again and again and again! I want you to take me morning, noon, and night, and numerous times in between! I want you to make me YOURS in ways we can only now imagine."

"WOW! So you want to have sex with me again?"

"I want us to have sex so many times that, if you carved a notch on the bedpost every time we had sex, we would have to be sleeping on the floor before the end of the week!"

"I must say, that sounds like a lovely agenda. I may need to get a little rest if I am going to fulfill that schedule. Could I curl around your beautiful body and hold your breast as we sleep?"

"That sounds perfect," my little sister replied. Soon we were both sound asleep.

The sun was just peeking through the window when I awoke to the sensation of Bethany sucking on my cock. As soon as I was aware and my cock was hard, my little sister straddled my hips, grasped my manhood, and guided me into her wet pussy. She immediately started to ride me like a bronc rider.

I was lying on my back, watching the most beautiful breasts in the world bouncing around as Bethany pumped her hips up and down, forward and back as she rode on my engorged member. I could feel her vaginal muscles gripping me every time she lifted. I wanted to reach out to touch her beautiful breasts, but she indicated not. So I enjoyed the most wonderful sights and sensations!

Bethany began to grind her clitoris against me with every stroke. Her pace had increased significantly and her breasts, chest, and neck were becoming flushed. Then she squealed, her hips lurched and flailed, and her coordination failed her. I rolled her backwards and began to thrust into her spasming pussy. I pumped long, deep strokes into her again and again. Bethany jerked and flailed beneath me.