Journal of an Agent Ch. 17

Story Info
Sking, relaxation & Winona Ryder?
4.7k words
4.26
49.4k
6
0

Part 17 of the 28 part series

Updated 10/23/2022
Created 05/22/2001
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Standard Disclaimer:

You must be 18 to read this story, be able to read erotica in your community, not be offended by the contents of it...blah blah, you know the rest.

This story may be distributed freely, for commercial or non-commercial use, but PLEASE leave my email/name on it! That's all I ask!

This is Part 17 of an ongoing series. Yes I know the celebs don't act like this in real life, but this is a fantasy after all.

* * * * *

"Are you sure you have everything Dean? Briefcase, luggage, passport, tickets..." Damon said, rushing around my office in a fever of activity.

"Yes Damon, I'm fine. I have everything. And if I don't, I'll just call you on my cell phone and have you FedEx it, ok?" I replied, standing at the door waiting on him to finish looking around so he could take me to the airport.

Damon stopped in the middle of the room, dropping his hands to his side and smiling weakly.

"Sorry, I just know how I get before trips. I freak out and always worry that I left something behind," he said.

"I have everything I need. Besides, this is a vacation. It's NOT a business meeting. Relax," I said, ushering him out the door.

We got into my BMW and headed to the airport, Damon driving frantically on the freeway like a maniac, trying to get me to the airport, despite my plane not leaving for 2 hours. I tried to tell him to relax and calm down but he seemed to ignore me, so I just let him do what he wanted.

Whipping into a parking space, he barely had cut off the engine before he flew out of the car, grabbing the luggage with him and hustled into the airport. I armed the car and chased to catch up behind him.

"Damon..." I said, jogging beside him. "Damon! DAMON!" I finally screamed, getting his attention and making him stop.

"Huh? What?" he said, out of breath as well.

"STOP. We can walk. The plane doesn't leave for over an hour. Relax," I said, grabbing his shoulder. He set the luggage down and wiped a small trickle of sweat from his bald forehead.

"Ok. We can walk the rest of the way," he said, picking up the suitcase and continuing on down the terminal calmly.

I checked in and boarded the plane a few minutes later. Damon had indeed chilled out while I boarded, his nervousness over being left to run the office while I was gone very apparent.

The plane took off after only a minor delay and I relaxed in my seat and enjoyed the plane ride on the non stop flight to Sweden, where I would spend the next week skiing. I had decided to take this vacation at the spur of the moment, the summer heat and energy crisis fiasco of California wearing me down. I hadn't skied since I was much younger back East, but felt that Sweden would be the perfect place to go and unwind. No celebrities to deal with, no headaches and nothing but a ski lodge and a mountain of pure white snow.

I arrived at the small airport outside the even smaller city where the resort was located. No terminal or rush of commuters around, I actually walked off the plane onto a tarmac. The air was bitter cold, a strong wind gust ripping at my face as I shielded myself from it. A line of cabs were waiting for passengers outside the airport, so I hopped in one and was on my way. The driver thankfully knew English and we arrived in no time.

After checking in, I went up to my room and took a long shower before taking a brief nap to kill some of my jet lag. Refreshed and ready to go, I walked down the mahogany stairs and scoped out the resort. A grand architectural style encompassed everything about the building, with a huge stair case leading to the second floor of rooms. The lobby/entrance area was plush and comfortable, the ceilings vaulted by two huge wooden beams. The roof was made of thick glass that looked out to the night sky, stars twinkling above. The lobby was practically vacant so I made my way to the bar, where I heard many revelers and fellow guests, speaking in a wide variety of languages, enjoying the thing that brings cultures together: alcohol.

The bar was rustic like the rest of the resort, with emerald green marble columns supporting the bar area itself. The back wall was lined with booths that were mostly empty, except for a few couples talking closely and intimately with one another. There was a very international flavor to the drink selection, as the majority of drinks above the bar I didn't know the slightest bit about.

"What can I get you sir?" said the bartender in a heavy Swedish accent.

"Jack & Coke please, with just a cube or two of ice," I replied, folding my hands on top of the bar and looking around. I glanced down to my right and saw a quite attractive blonde woman sitting alone, nursing a margarita. She smiled at me and I could tell she was checking me out. Not one to pass up the chance with a beautiful woman, I took my drink and went and sat next to her.

"Hi. My name is Dean," I said, extending my hand.

"Kate, pleased to meet you. You're an American as well?" she replied, holding out her hand daintily. Her fingers were long and thin, and she had quite beautiful hands, accented by a light baby blue shade of nail polish on her fingernails. The dress she was wearing matched her nails, a very light shade of blue held onto her buxom body by spaghetti straps.

"Yes, I'm from America. California actually. How about you?" I asked, smiling warmly at her.

"Dallas, Texas. I just came here to get away from the rush of the city and my job as a bank manager. I grew up in Colorado so I love to ski. How about you, where are you from and what do you do?" she asked.

"I'm originally from New York state, but I moved to California to take over my father's firm. I run Shooting Stars talent agency, one of the most prestigious Hollywood agencies in LA. Bank manager huh? Isn't that pretty slow and tedious stuff, besides handling all the money?" I asked, finishing off my drink and ordering her and myself another.

Kate laughed. "Well, it's not as bad as you would think it is, but I'm sure it's nothing like being around all those famous people all the time. Does your firm have many big star clients?" Kate asked.

"We have a few bankable stars. Sorry, that's Hollywood lingo. Yes, I represent people like Julia Roberts, Lucy Liu, Jennifer Love Hewitt and quite a few others that I can't think of right now because I think I drank that last drink too fast," I said, laughing.

"Wow, that's incredible! Tell me more!" Kate said, genuinely interested in what I did.

We continued talking for over an hour, downing drinks and laughing about the corporate world and the lives of celebrities. It was so nice talking to her, to talk to a real person and a real woman, not a pampered and rich star. Things were going along great and I was beginning to think that this conversation might lead to somewhere else (namely, my room). By the 5th or 6th drink, the conversation turned to sex and past affairs we had had.

While I was still on my feet and able to think and talk fairly well, I had drank so much in a while and I was feeling more than a little on the wasted side. And when I get drinking, my tongue starts to slip a little.

"My last boyfriend was an ass. He wanted me to do something really kinky. He said he wanted a three way with him, me and this girl from his work. I refused right on the spot, and dumped his ass a week later," Kate said, scraping off the salt from her margarita glass and licking it from her finger.

I don't know why I did it, but I just chose that break in the conversation to blurt out: "Three ways are nothing. I do them all the time. The most recent one I had was with Jennifer Aniston and Lisa Kudrow. You wouldn't BELIEVE how well those two girls fuck!" I said. I knew I had fucked up as soon as the words left my mouth, but it was too late.

Kate's face turned to one of shock and she stood up to go.

"You men...you are all the same. Thinking women are just your sexual playthings. Nice meeting you, but I have to go," Kate said, gathering her purse to leave.

And yet again my tongue got the best of me and I said to her: "Eh, don't worry about it. You're not attractive enough to be in a three way any ways,"

My drunken stupor was quickly broken when Kate slapped me across the face, the blow stinging and quite painful. She hurried out of the bar and disappeared around the corner. The rest of the bar had been watching the whole thing but quickly looked away when I glanced in their direction. The bartender seemed to be extremely occupied with a row of glasses that needed polishing and made no eye contact.

I was just about to leave when I heard a female voice laughing behind me.

"The great Dean Simonds gets rejected! I never thought I would live to see that day!" the voice said.

Spinning around on my heel, my head swimming, I was face to face with a woman I recognized instantly: Winona Ryder.

"Winona...what are you doing here? I am in Sweden aren't I, shouldn't you be in LA or somewhere shooting a movie?" I said, slurring my words together. My head had started to clear a little but I was still talking and reacting a little slow.

"I'm on vacation. I guess I just happened to pick the one spot where my agent's rival would be, haha." she said with a smile.

Winona was dressed very normal like, hardly any makeup on and her long dark brown hair pulled back behind her ears loosely. She wasn't wearing anything flattering, just a pair of ski pants and an oversized parka. Still, I had known right away who she was, her natural doe like beauty apparent even in this bar.

"Oh. Well, I'm on vacation too. Skiing actually. Just got here today, but I don't think things are going too well so far," I said.

"Well, if the way that woman treated you is any indication than I guess not. Dean, you've got to realize that the women from other parts of the world are nothing like LA women. They can't be wowed with your tales of sexual prowess. Even I wasn't that impressed and look at me, I've been in the business for a long time," Winona said, taking a sip of the beer she held in her hand.

"What do you mean? How ELSE should I try and pick up a woman?" I said, feeling utterly stupid in asking the question.

"Let me explain it to you. Here, why don't we step outside for a minute, let you clear your head in the cold air. I need a smoke anyways," Winona said.

I nodded and asked the bartender for a cup of coffee, black and followed Winona outside.

The air was indeed quite frigid and cold, snow falling lightly outside into the parking lot where a few SUVs and Mercedes sat, caked in it. The light from the lobby of the resort cast a pale yellow glow onto the world outside and the mountains loomed dark and foreboding a few miles away. The skyline was dotted with ski lifts hung suspended in the air, stopped for the night.

Winona and I sat across from each other on two wooden benches outside, the canopy ahead offering only a little bit of protection from the cold and bitter wind that would gust in occasionally.

I sipped my coffee while I watched Winona fish in her purse for a pack of Marlboro lights and her lighter. Pulling the long white stick from it's pack, the paper of it almost matching her pale white skin, her face was lit up as she sparked the lighter, the orange glow of the flame struggling not to go out in the wind.

"You know, those things will kill you," I said to her, watching as she inhaled and blew out a whiff of bluish smoke that was quickly ripped apart by the breeze.

"Yea, I know. And don't you tell my agent either. After I got chastised by the Surgeon General for being a 'female role model that portrays to young girls that smoking is ok in all of her movies'" Winona said in a deep, mocking voice, "My agent made me promise to quit. I tried, I really did. But sometimes, I just need one."

"We all have our little vices. You have your cigarettes, I have my full on sexual obsession with fucking celebrities," I said, trailing off.

Winona laughed, a little bit of the smoke billowing from her mouth. "That's your problem. You've lost touch with the normal woman," she said. "You need to go back to your days as a teenager. You need to know how to talk to her, find out what she wants and doesn't want and if she is your type or not,"

"Is that what works for you? Or are you just dispensing advice against celebrities while being a celebrity yourself?" I asked, drinking my coffee.

"I don't go for celebrities. I learned my lesson after Johnny Depp. Men who are famous or are around famous people get too full of themselves. They don't know how to just leave the business behind and be a real person. And while I think you are a cocky bastard who likes to brag about how much pussy he has nabbed, you still have a very normal 'every guy' heir about you," Winona said, stubbing out her cigarette and blowing out a final whiff of smoke.

"You think so huh? Well, I appreciate that. Except the cocky bastard part of course," I said with a smile. Winona smiled back.

"Don't mention it," she said, shivering a little. "I'm cold as hell, what say we hit the jacuzzi for a little bit. It closed an hour ago but I won't tell if you won't,"

"Sounds good to me. Let me just go up to my room and change," I said.

"No, you don't have to do that. I say we go skinny-dipping. I want to see if all those rumors about your, ahem, equipment are true," she said with a broad smile. The light from the hotel twinkled in her eyes and I thought I saw a flicker of lust and sexual desire in them (I've become quite attuned to picking up on that sort of thing).

"Well, I can assure you that it's all there. The question is, will you be joining me or am I going to just be putting on a show for you?" I asked, grinning at her.

"Don't worry, I'll play fair," Winona said.

We walked through the lobby and down an adjoining hallway towards the gym/spa area of the lodge. The jacuzzi and pool were at the very end of the hallway - private and secluded.

Winona went in first, not even hesitating to strip naked. In one motion, she had removed her parka and top. Next came her boots (all her articles of clothing flung haphazardly onto a nearby bench) and then her pants and panties and Winona was naked in almost 5 seconds. I watched her pale, lithe white body make it's way towards the jacuzzi, her firm and tight ass swaying and jiggling a little as she walked. Winona reached around her back and undid her hair, shaking it free over her shoulders as she entered into the jacuzzi slowly.

"Ooooo...that feels SO GOOD!" Winona exclaimed, the steam from the bubbling whirlpool encompassing her whole body.

Turning around to face me, I made out Winona's large breasts and her dark red areolas in the light, her pussy hidden under the water.

"Well? Aren't you coming? I want to see that thing!" Winona said at me, holding an arm out and beckoning, her finger moving in a "come hither" position.

Strange as it was, I was a little hesitant to strip naked. I didn't know what to expect from this situation - if Winona really just wanted to relax and talk (while we were both naked for some reason) or if she wanted to fuck. With a little bit of hesitation, I removed all of my clothing and walked into the jacuzzi.

The water felt warm and comforting, soaking into my skin and relaxing the tension in my muscles from the long flight earlier in the day. The steam filled my nostrils, a chlorine smell that felt heated and relaxing. I couldn't help but recline a bit in the jacuzzi and just enjoy the flow of water.

Winona lay across from me with her eyes closed, also enjoying the relaxation. Her nipples and breasts swayed gently in the current of the water, the tops of her breasts sticking out just above the waters surface. "I could lay here forever. Everything just seems to melt away," she said.

Winona opened her eyes and a wide grin spread her face. "Ok, now, let's see that thing of yours! Stand up!" she said.

I gave her a kind of puzzled look, still trying to scope out the situation. Nevertheless, I placed my hands on the side of the spa and lifted myself up, so that I towered above Winona. Coincidence or not, my half erect dick hung just at the same level as her mouth.

"Here, come closer. I want to touch it!" Winona giggled.

Taking a step forward, my nine inch cock was now inches from her face. Winona lifted her arm from the bubbly water and wrapped her hand around my prick. Her fingers were small and surprisingly a little cold, despite the temperature of the water. I jumped a little when she touched me but as she began to run her hand up and down my member, I quickly adjusted.

It didn't take more than a few strokes before my cock had grown to full length. Winona stopped jerking and admired it, playing with my balls in her hand and rubbing the palm of her hand over the head.

"My my my...Jessica was right. You ARE quite well hung.I wonder how you taste..." Winona said, lowering her mouth over my prick. Her mouth was warm and inviting, just the like the water that I stood in. Winona's mouth moved down to the base of my shaft, her throat working in one motion to deep throat me. She slowly pulled her mouth off of my dick, her lips making a smacking sound as they popped off from the head.

"Tastes good too. Ok, that's all I wanted to know. You can sit down now," Winona said.

I stood there dumbfounded, my dick still coated in a layer of Winona's saliva.

"What? Sit down Dean, that thing is distracting," Winona said. Not knowing what else to do, I followed her order.

"You didn't REALLY think I was going to fuck you just like that did you?" Winona said, an evil little grin on her face. "No, don't worry, you'll get laid tonight. But first, I'm going to teach you how to please a woman,"

"First things first, you need to know how to eat a pussy. You have been kind enough to return the favor to a woman before haven't you?" Winona asked. I was getting a little angry by her methods but I wanted to see where she was going with this.

"Yes, of course I have. Just ask your 'friend' Jessica. Or any of the other celeb women I've been with," I replied angrily.

"Alright, alright. Calm down. Just a question. Let's just see if you can put your money where your mouth is," Winona said, grinning. She lifted herself up out of the jacuzzi and onto the edge of the wooden railing beside it.

Spreading her legs slightly, Winona's cunt was just a foot or so away. "Come on Dean, let's see what you got," she said, holding her inner pussy lips open a little.

I moved my way over towards her pussy, the odor from it strong and pungent, filling my nose with an intoxicating aroma. Her legs and outer lips were wet with the water from the jacuzzi, with a slight foam of bubbles. She was shaven in a V pattern around her cunt lips, and I could see moisture inside of her pussy.

Lowering my head towards her, I heard her take a sharp intake of breath as my tongue touched her. Winona relaxed a little and I began to lick her.

I began to move my tongue around her lips, delving it in sporadically towards her hole, opening her pussy up like a flower with every thrust of my nimble tongue. Burrowing my face deeper into her, I slid my tongue into the depths of her tight pussy, licking around and searching for her clit. Winona closed her legs tighter around my head instinctively, making it hard for me to breath in my wet, hot jungle. I thought I was doing a good job eating her out but apparently Winona wanted to give me some tips.

"No no no, you are doing it all wrong. What you have to do is move your tongue over theRRREE!!! WOAH! KEEP DOING THAT!" Winona said. With a flick of my tongue, I wrapped it around her clit and began sucking my tongue backwards over it. Right about when I started doing this was when Winona's complaining began, and it quickly shut her up.

"Ooooooo! Yes! Right there Dean! Yes! Don't stop! Keep licking my clit! Oh God, oh God! Yes, I'm CUMMMMMINNNNGGG!!!!" Winona screamed, her voice echoing in the small room, bouncing from the wooden walls. I felt a flood of juice hit my face as Winona orgasmed, an excess of her cum leaking down my chin and into the jacuzzi. Winona's juices tasted sweet, a tangy taste that danced around on my tongue. I swallowed half a mouth full of her cum, the rest falling on my face. I glanced up and saw Winona laying down on the floor, her legs dangling in the water. Winona was catching her breath, so I dunked my head under the hot water and rinsed my face off.

12