Anal

Kristy looked out over the city of San Juan from the balcony of her resort hotel. The sun was setting to her left and ahead of her lie the old city. Out of place in the picture, but adding to the charm, was the cruise ship port with one brightly lit boat heading out into the Caribbean. San Juan was the epitome of old and new, undeveloped and contemporary, inactive and on the go.

That’s also how Kristy used to feel about conferences like the one this week. She loved the traveling part of her job, but she hated the tedium of conferences. They used to all blend together and all the attendees looked and acted the same. Then she took control.

At the age of thirty and among the most attractive women at any conference she attended, the sexy, single blonde would have no problem finding company among the young and old corporate executives in attendance. However, she wasn’t satisfied with just sitting at the bar waiting for offers.

What she yearned for on trips like this was the impossible-to-find man of good looks, intrigue, wits and intelligence, who knew how to amuse her. Would she have sex with him? She didn’t know the answer to that until knowing the man better.

Kristy, like most adults, had sexual fantasies. Unlike most adults, she acted upon them. She made them happen and it took a special man to be the lucky recipient of her favors.

Now, standing on her enclosed balcony on the first evening of the San Juan conference, she was ready to begin her quest. The sound of the sliding glass door opening and closing on the balcony next to hers was a good sign. Kristy heard a chair being pulled and what sounded like a glass being set on a table.

She had noticed earlier that an opening of several inches between the balcony wall and the hotel room allowed a view onto her neighbor’s balcony from just inside her sliding door. She quietly walked now to that spot and peered through. A man of about forty years of age sat at the table, looking out at the city and port. Every feature of his face attracted her at once. His perfectly groomed hair and crisp shirt signified success, or at least class, to her.

Seldom was she so lucky to have a potential target right next door. And if he only turned his head a little, he could see her. She decided to give it a try.

Kristy pulled a t-shirt and shorts out of her dresser, then returned to the spot allowing him to view her. She purposely slammed her sliding door shut to attempt to get him to look. The instant he began to turn his head, she pivoted so that he was looking at her silhouette. Kristy gave no sign of knowing he could see her.

She tossed the new clothes on a nearby chair and extended her arms high above her head in an apparent yawn. She wore a short skirt which rode high up her legs when she stretched. Her blouse hugged her full breasts even after she let her arms fall back into place.

Then Kristy began to unbutton the blouse, deliberately slowing the pace to about half of what she would normally do. She hadn’t yet attempted to sneak a glance his way to see if her neighbor was watching. But she would.

As soon as the last button was open, she slid the blouse off and tossed it aside. She made sure to turn in such a way that he had a couple different angles to view her breasts. Then she reached back to unhook the tiny bra.

That was when she was able, out of the corner of her eye, to confirm that he was, indeed, observing every move she made. She held the bra in place while the straps fell down her arms. At the very last second, she turned her back to him and let the bra drop to the floor. She took a few seconds to run her hands over her tits, making it obvious she was massaging them.

Then Kristy unzipped her skirt. That, too, fell out of view. She pulled up on her bikini style panties, giving an extra little tug to expose a bit more of her ass cheeks.

Then she leisurely put on the t-shirt and shorts before walking away from the door, into the center of the room out of his sight. She smiled and wondered when they would meet again.

The following day started with the usual hodge-podge of convention seminars, none of which were going to make Kristy an industry giant. But she was obligated to attend some before the afternoon pool break and chose one that sounded the least tedious.

It was packed, which was a good sign. But about fifteen minutes into it she began to question her seminar selection skills. Kristy started to look around the room. At the same time, she felt an eerie presence of eyes staring back at her. She looked over her shoulder and he was there. The man from the balcony was behind her and one seat over.

The moment he had her attention, he mouthed the word ‘Lunch?’ Kristy tried not to let her delight show. She grinned shyly and nodded.

The moment the seminar ended, they met in a back corner of the room.

“Is noon, OK?” he asked.

“Sure. Where?”

“The entrance to Choices Restaurant, right outside of the convention center.”

Kristy nodded. “Yeah. I know where it is.”

He pendik escort caught her stealing a glance at his name badge.

“I’m Doug.”

“Hi. I’m Kristy. I don’t think we’ve met.”

He grinned sheepishly and her attraction to him grew stronger by the second.

Doug said, “We’re neighbors.”

“Really? At the hotel?” she said with totally believable astonishment.

“Yeah. That’s a great view from the balcony, isn’t it?” he asked, assuming she didn’t catch the irony of the question.

“Yes. I think I’m going to like it.”

“Me, too,” he assured her. “So, Choices at noon?”

“Sure. I’ll be there.”

The next hour couldn’t go fast enough for her. This was a guy she seemingly could have fun with. But Kristy had gone through this before on trips and she knew that one meal always told her what she needed to know.

He passed the good-looking test, however. His tan was clearly natural and she wondered what he looked like in less formal attire. But if his ass was any indication….

Kristy spent the five minutes prior to noon in a ladies room checking her makeup and hair. She wasn’t one for bright lipstick or eyeliner, but she knew how to do great things with just the right touches in the right places. Her natural beauty would do the rest.

Soon, she was at the restaurant, being ushered to a table along with her new companion. The conversation never once turned to the previous evening. Doug wanted to know everything about Kristy and her job and she did the same with him.

Doug learned that Kristy was a star soccer player in college. She learned he played guitar in a garage band in high school and still played in a Rolling Stones cover band. He admitted to never having lifted a weight, but finished a half marathon once. She admitted to trying weed once.

They laughed a lot and missed their one o’clock seminars.

After the bill was amiably picked up by Doug, he asked, “Are you going back for more riveting lectures?”

Kristy shook her head. “I’ve had my fill for today. I think it’s pool time for me. How about you?”

“I’m not sure. I might just go to the room for a bit and then head into old San Juan for the evening,” he said.

“If you decide to do the pool, either look for me…or…knock on my door to see if I’m still up there,” Kristy said in the form of an invitation she rarely made this early at a conference.

“OK,” was his only reply.

Back in her room, Kristy changed into her bathing suit, a one piece affair that she felt much more comfortable in at a conference than her normal vacation bikini. She was, after all, supposed to be a professional working woman. In public, she would act like it.

She neither expected nor heard Doug’s knock on the door, so she headed for the pool. To her surprise and delight, he grabbed the lounge chair next to her fifteen minutes later.

Her wish of seeing him in less formal attire was more than granted by the fact Doug wore a boxer-style pair of trunks and no shirt. He was well toned for his age, and for a man who claimed to have never lifted weights. Apparently guitar playing was good exercise, she thought to herself.

They spent an hour talking, with Kristy being the only one to enter the water and that was only to cool down. Doug never took his eyes off her the entire time and that did not go unnoticed by her.

As soon as she was dry again, she said, “Well, I’m heading back. Are you staying?”

“Can I walk up with you?”

“Of course.”

As they approached their rooms, Kristy debated with herself. ‘Do I let him go?’ ‘Do I invite him in?’

“When are you going out again?” she finally asked.

“A few hours yet. Whenever I’m hungry,” he said with a grin.

Her mind was made up. “Want to come in?”

“Sure,” he said calmly.

They laid their towels down and Kristy offered a drink, which Doug refused. She suggested they sit on the balcony and he accepted.

Their small talk was friendly, if not all that interesting.

Doug was almost getting used to seeing the beautiful woman in her bathing suit, with her full breasts barely contained at the top and her smooth thighs flowing below the high cut at the bottom. But he still stared occasionally and she sensed his eyes at times.

She finished a soda and excused herself to get another. Doug moved inside and sat in a chair opposite the couch, where Kristy seated herself and put her glass on a table. She let her eyes moved from his crotch to his face.

“Excuse my straightforwardness, Doug, but do you have fantasies?”

A younger man would have lost his chance with Kristy at that point. Doug surveyed the woman, quickly calculated the situation, and replied, “At this very moment?”

Kristy giggled, looked at him with approval, and said, “Not necessarily. In general.”

Doug was barely grinning, but she saw the confidence on his face. They were both enjoying the game.

“Yes. Of course. We all do,” he said. “I often think about watching a beautiful woman undress.”

If maltepe escort that was his clue to her that she was seen the evening before, she got the hint and it excited her to no end.

“And then what?” she asked.

He paused, crossed his legs, and said, “And then watching her masturbate.”

She rested one hand on the top of her right leg. The other hand casually brushed past the bottom of her breasts. Then the hand on her leg moved onto her thigh and up to the edge of her suit.

“Should I? Now?” she asked in a near whisper.

Her fingers lightly touched her pussy, on top of the suit.

“That would be nice, Kristy,” Doug replied.

She stood and faced him. Kristy took hold of both straps of her bathing suit and very slowly pulled them off her shoulders. She revealed her breasts in tantalizing pieces, inch by inch, until the top of her suit hung at her waist.

Just as slowly, she pulled the suit down and stepped out of it, remaining on her feet for Doug to view her nakedness.

Her tits were perfection. Her waist and hips curved magnificently. Her pussy was neatly shaven with a patch of light hair above the clit.

“Turn, please,” Doug requested.

He had seen the ass before, but not this close and not completely bare. It was better than he imagined.

Kristy sat again and placed her hand on her pussy. She leaned back. Not wanting him to see the trembling of her hand, she began to massage her pussy in long, slow strokes.

That’s when she first noticed the bulge in his bathing suit.

“Take it out, Doug. But don’t touch it after that,” Kristy said. “Just watch.”

Her pulse quickened when he lowered his trunks and released the already sizable cock. Kristy found her clit and rubbed it harder, unable to take her eyes off his erection. Doug’s eyes were in constant motion with Kristy’s hands working over her tits and pussy simultaneously. Soon, he was rock hard and the cock throbbed from the need for attention.

Kristy masturbated more urgently, spreading her legs farther and slightly bending her knees. She clutched at her tits and pulled on the nipples, moaning louder as the minutes passed. Doug watched her insert a finger into her soaking wet pussy and then use it to stroke her clit some more.

Her body shook as she got closer and she thought of the previous time he watched her. This time he would see, and hear, her climax. A drop of precum leaked from his cock and Kristy smiled to herself. She whimpered as her orgasm came nearer and Doug’s own breathing accelerated.

Kristy tilted her head back, stabbed at her clit a few more times, and cried out, “Oh God. Yes! Yes!”

Doug watched her body writhe on the couch. Her hips thrust forward to meet her hand and she massaged the clit harder. Over and over she voiced her ecstasy while inserting a couple fingers inside her pussy, only to return to her clit and cum again.

Several times he had to stop himself from grabbing his cock, wanting desperately to let her act out whatever fantasy she, herself, was having.

In the end, Kristy slumped back and caught her breath, not opening her eyes for more than a minute. Finally, she looked across at Doug and his harder than ever erection.

“Thank you,” she wheezed. “Thank you for just watching.”

“My pleasure.”

She looked at him with growing desire. “If you’ll have me, I’d like to go to dinner with you.”

“And we can discuss your fantasies,” he said with a smile.

“We can do that. I owe you at least that.”

Old San Juan is the historic center of the city and the main tourist area on that part of the island. With the convention center and surrounding hotels within a five minute cab ride, the district buzzes nearly every night. Colorful, narrow streets fan out in all directions with water a short distance away on three sides.

Restaurants are plentiful, but inconsistent. Fortunately for Kristy, Doug had done his homework online before arriving for the conference. His recommendation was accepted by her without question.

She wore a sleeveless, form fitting dress that stopped well short of her knees. The plunging neckline certainly met with Doug’s approval, along with every male they passed on the way to the café.

The talk was a little more centered around the conference and their jobs this time. It wasn’t until dessert that the discussion became more personal.

Kristy leaned forward after the waiter left at one point and said, “So, you haven’t asked about my fantasies yet.”

“You know I would have,” Doug admitted. “I’m all ears.”

“First of all,” she said. “Was this afternoon as good as you hoped for?”

He grinned. “Absolutely. Couldn’t you tell?”

She blushed.

Doug continued, “I loved every second of it. But I fought back every urge I had.”

“To do what?” Kristy asked.

Now Doug leaned forward and said quietly, “To fuck the hell out of you.”

Kristy nearly choked, putting her napkin up to her mouth, partially to cover her laugh.

“I see,” she finally kartal escort was able to say. “You looked…ready. Which brings us back to my fantasies.”

She paused to make sure she had his attention, which was unnecessary.

“I think I’d like to repay you,” she said in hushed tones. “But not in the room. That’s so…ordinary. I’ve always wanted to do it in public. Or, at least, somewhere where the possibility of being caught exists. That would be so cool, don’t you think?”

“I’d show you what I think,” Doug told her, looking down at his crotch. “But I’d be arrested.”

She giggled and shook her head. “Not here.”

“I’m sure old San Juan had lots of nooks and crannies we can discover,” he said.

Kristy playfully used her spoon to hint at her objective. This time it was Doug who stifled the laugh.

They were only out of the restaurant for five minutes, having walked down a fairly uncrowded street in their quest, when Kristy took hold of Doug’s arm, pointed to the door of what appeared to be a narrow, tall apartment building, and said, “There!”

“If this gets us arrested, I’ll never talk to you again,” Doug said as they advanced.

“You don’t even know me,” Kristy countered.

She turned the old, rickety doorknob and, somewhat to her surprise, the door flung open. They both stared into the shadows and saw the steep set of stairs leading upwards. There was hardly room for two people to stand at the bottom of the stairs.

“Perfect,” Kristy uttered, pulling Doug in behind her.

Once the door was closed, she pushed him against the wall and commenced a long, hard, passionate kiss. Doug’s hands were all over Kristy’s dress, spending extra time on her ass and chest. Kristy managed to grab one of his wrists and she guided his hand onto her tit. Doug did the rest, exploring inside the dress while Kristy rubbed his crotch, thrilled at the quickness of his budding erection.

Then she frantically pulled down his zipper and sought out his cock. It was outside his pants in a matter of seconds and she was stooping down to meet it. She would have preferred to spend an hour indulging it with attention, but they might only have minutes.

So, she licked the underside of the thick shaft two times, kissed the tip once, and put it between her lips. Doug sighed loudly as she lowered her head onto him, taking the entire length into her mouth. Kristy’s tongue worked its magic and her lips applied more and more pressure the faster she bobbed her head up and down.

Doug held her head, playing with her thick blonde hair as the blowjob continued. Outside, the sounds of passing tourists on foot and in cars were undeniable. In the tiny space they occupied, only the sounds of Kristy’s mouth and Doug’s moans were added to the mix.

Nobody wanted the session to last longer than Doug. But the excitement of the circumstances and Kristy’s skills had him close right away. It seemed like they had just started when he felt the pending explosion.

“Jesus, Kristy. That’s so good. Yes! Just like that,” he murmured.

She never took a breath or slowed the pace. Doug held her face closer. He felt the orgasm building.

“Yes! Yesssss! Oh my God, Kristy….”

He grunted noisily and Kristy took a long blast of his cum into her mouth. She tried to swallow, but another shot combined with the first. Then another. A stream of cum flowed out the side of her mouth and Doug’s orgasm continued, resulting in his cock being covered in his sweet juices and Kristy’s face containing what she couldn’t swallow.

When he was done, she wiped her face with a couple of fingers. After she was standing once more, Doug clean off the top of one tit with his own hand, letting her lick the finger clean while he put away his cock with the other hand.

“Damn, that was fantastic,” he told her, followed by a kiss.

Just then, the sound of a door opening far above them caused them to run out onto the sidewalk and slam the door behind them, laughing the entire time.

They parted that night outside their hotel rooms, knowing that it was only a matter of time before they shared a bed. Doug wondered, appropriately, how it would happen. Something made him suspect it would not be routine. Not with Kristy.

The next morning they met again in the corner of a lounge inside the convention center, as isolated from the crowds as it was possible to get. They drank coffee and discussed their plans for the day ahead.

“I’ve got a potential client I have to pin down today, if I can,” Doug was saying. “He wants our software, but is leery of the cost because of the size of his firm. I can’t convince him we’ll work with him on it.”

“How much are we talking about?”

“I want two hundred twenty five thousand. He wants one hundred seventy five,” Doug said.

“Would you take two hundred thousand?”

Doug grimaced, but admitted, “Yeah. I could live with that.”

“Can I help?” Kristy queried, sipping her coffee and looking at Doug over the cup.

He looked back at her with questioning eyes. “If you persuaded him to accept anything from two hundred thousand and up, I’d owe you big time.”

“I can be very persuasive,” Kristy said dryly. “Did you ever think you’d get blown in an entrance to a San Juan apartment building?”

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