That's the Onebyeroslit©
Brad felt his heart pound as he stared at the photo. After seeing so many faces and bodies of so many women, it was an incredible feeling to actually find the 'perfect' one.
"That's her! That's the one," he exclaimed.
Sitting next to him, Jim smiled. "I can't believe it. Eileen is my favorite. But the guys all seem to pass on her because she's not busty enough."
"But that's what I want," Brad said with enthusiasm. "About thirty, thin, average tits and ass and fucking sexy as hell."
He turned the page to see a couple more photos of her in various outfits and poses.
Eileen looked like she could have come straight from the Hollywood set of an Irish movie. Faint freckles dotted her face. A tint of burgundy mixed in with her brown hair. She was an adult with a touch of innocence.
"That's the one."
"She's available," Jim said, taking notes as they spoke. "Let me get the paperwork and you'll be all set."
Jim ran an escort service, specializing in women who accompanied men, or other women, on business trips and vacations. In this case, Brad was going on a cruise. Jim would arrange for Eileen to meet up with him on the cruise ship and the rest would be up to Brad. Jim WAS happy for Eileen, who rarely had this type of an opportunity for a week-long cruise with a class guy. He considered her sophisticated and elegant, but her girl-next-door body made her a less attractive pick for most men looking for the otherwise unattainable woman.
Brad was a good-looking forty two year old corporate executive who preferred going to his old friend Jim for a no-strings-attached week of companionship and sex with a woman he could trust, as long as she agreed to all 'terms and conditions.' Primarily, that meant do what Brad, the client, told her to do.
Little did Brad know that Eileen was capable of far more than that.
Eileen could barely contain herself when she got the text from Jim about her 'assignment.'
"A cruise. A fucking week-long Caribbean cruise!" Eileen shouted.
She was alone in her condo, but that didn't matter. Jim had told her this was a perfect guy for her and he loved her photos. She rolled off the couch and jumped in the air like a kid at Christmas.
"Finally," she said. "I'll make this guy the happiest man on the face of the Earth if it kills me. I'll fuck him until his cock falls off if he wants."
She skipped down the hall and into her bedroom, anxious to pack enough clothes for a week of sun, sand, and sex.
A long time ago, Brad quit beating himself up over the fact he had to use Jim to find dates like this. In fact, he now chose to take this route every time. He decided his position in the corporate world, once it became known by the women he met, simply made him the target of money hungry bimbos. Nothing against arm candy, he told himself, but long-term relationships with such females did not excite him.
Eileen excited him.
For the first time on one of these vacations, he truly felt nervous. In a strange role reversal, he wondered if HE could satisfy Eileen. He laughed to himself at the thought. Still, he wondered.
She looked too perfect with her flowing brown hair, tan skin, dark eyes and small, turned up nose. Her mouth was thin and sensual. Her breasts hinted at being firm and round. She never appeared nude in the photos, but he liked the way she used her body to tease him with her attributes. Her waist was small and her hips perfectly curved. Her ass was tight; her legs smooth and firm.
Even without a picture before him, he felt his cock react.
Eileen never got to see the man she would be with until the day they were to meet. On that morning, Jim would e-mail her a picture. All Jim told her now was that he was forty two, twelve years her elder. He said she would not be disappointed and Eileen trusted Jim completely.
She filled her suitcase with the 'special' outfits she had reserved for an occasion like this, even though one had never occurred before. She held certain things in front of her as she looked in the mirror, hoping beyond hope this man would appreciate her selections. Or was he more concerned with how she looked WITHOUT them on?
She smiled at that prospect, too.
Brad and Eileen were to meet at a designated spot inside the Miami airport around noon of the day the cruise began. Both flights arrived on time and Eileen instantly checked her e-mail upon landing. The picture Jim promised was there. She smiled with nervous approval when she opened it and felt, at last, that the trip was really going to happen.
Eileen made a quick stop at a restroom to check her hair. A quick glance in the mirror at the deep cut of her v-neck top and exposed cleavage—what little there was—convinced her she made the right choice for this first meeting. She checked the back of her shorts one time and walked out to head for baggage claim.
Fifteen minutes after Eileen was in her designated spot, Brad was approaching. He recognized her instantly, even from three gates away. She was prettier than in her pictures and presented a stunning figure as she sat with her legs crossed. As often as he had met Jim's girls, the process still scared him. But never had he longed to meet somebody as much as he wanted to meet Eileen.
Their eyes met.
Brad reached out his hand and Eileen held it lightly.
"Good flight?" he asked.
"Uneventful. My kind of flight," she replied.
"Ready to go, or do you need more time?" he asked.
Eileen sprang to her feet. "I'm ready."
The ensuing conversations while the couple traveled to the port, embarked onto the ship, and waited for their cabin to be ready persuaded both of them that their personalities matched fairly well. Indeed, Brad was not paying for Eileen's great personality, but it certainly didn't hurt. By the time the cabin was prepared for them, Brad and Eileen were comfortable enough around each other to enter their home for the next week with relative ease.
"When the luggage arrives, you can have first choice on any closets and drawers," Brad said. "I'll take whatever is left over."
"Oh, you don't have to do that, Brad. I won't take...," Eileen said.
"No. It's alright. Take whatever you want."
"Thanks," she said with a grin. "I didn't pack as much as you might expect."
"How about a swimsuit?" he asked. Brad's wicked smile assured that she took it in the playful way he intended.
Eileen patted her carry-on. "Right here. I thought we might have time for the pool before the luggage arrived."
"Can I see it?"
Eileen unzipped the bag and pulled out both pieces of the light blue bikini. She held them up for his assessment.
"Put it on, please."
Eileen's heart thumped rapidly. This was it; the first step. For right or wrong, so much of the success of the rest of the week rested on how she handled this moment. Eileen was prepared.
She laid the bikini on the bed and turned to face Brad. With full confidence, Eileen grabbed the bottom of her shirt and pulled it up. When it cleared her head, she shook her hair back into place and tossed the shirt aside. Brad openly stared at her bare breasts, marveling in the perfection of their size and shape.
Eileen gave him a second to look, then opened her shorts and gently let them slide down the top of her legs. Small, white panties covered her pussy and ass. The shorts slid down her legs and Eileen bent over to pick them up. After another short delay, she took off the panties. When she bent over again, she made sure to give Brad a complete show without being too blatant.
This time she offered her body to him for a complete viewing.
"Beautiful," he said softly. "Very nice."
Eileen slid on the bottom of the bikini, pulling the material tight against her pussy and ass. Then she put on the top, turning her back to Brad, saying, "Tie it, please."
Brad eagerly complied, glad to see that Eileen had the self-assurance to ask him to do it. He let his fingers slide down her bare arms, across her back, and down the outside of her legs.
"You're very beautiful, Eileen."
"Thank you. I hope I can make you happy," she answered.
"Oh, I think you'll do just fine," he assured her. "Now turn around."
She didn't know what to expect, but was pleasantly surprised when he took her face in his hands and kissed her. At first, it was a gentle kiss on the lips. Then their mouths opened and their tongues met. Soon, he was hugging her tight and the kiss was passionate. Immediately, Eileen felt the stiffness of Brad's cock against her body. She sighed at the suddenness of the embrace.
"It's going to be a fun week," Brad said when they separated.
Eileen grinned. "I think so, too."
It wasn't a total coincidence that her hand was lingering on the outline of his cock when she said it. But she got the impression this was not going to be their first sexual encounter. Brad alone would determine when that occurred.
"Want to head for the pool now?" Brad asked her.
"Sure. Let me get a shirt out," Eileen said, digging in her carry-on for the top that went over her bikini.
Once that was on, they were ready and the couple spent more than an hour sitting at the pool talking and drinking sodas. Brad apologized to Eileen for making her go on a cruise with somebody who didn't drink much, but it suited Eileen perfectly fine. She'd had more than her share of bad experiences with drunks. If Brad treated her well, she didn't care what else he did.
They each learned a little about the person they would be with for a week, but neither divulged any secrets they didn't want out. Eileen admitted to being divorced and a former flight attendant. Brad told her he was engaged once, but it broke off at her request. Ever since, he was married to his job.
They talked briefly about what shore excursions they might want to sign up for, but Eileen deferred to Brad. He half-joked about a clothing optional beach he knew about and Eileen enthusiastically agreed to 'try anything once.'
Brad promised to find out if she really meant it.
When they returned to the cabin, the luggage was waiting. Brad tossed Eileen's suitcase onto the bed and put his own on the couch. When he turned around, Eileen was standing close to him in her bikini, having taken off her shirt.
"Maybe I should start practicing going topless for that beach," she said.
Brad didn't press his luck by telling her that clothing optional meant nude. Instead, he said, "I'd like that."
Eileen leisurely untied her bikini top and pulled it off. With a mischievous look over her shoulder, she walked back over to the bed and began unpacking. The next several minutes were ecstasy for Brad as they unpacked, often brushing against one another while they moved about the cramped cabin.
The only interruption was a knock on the door which caused Eileen to make a hasty retreat into the bathroom. Brad spent a minute or two being greeted by the room attendant, after which he announced to Eileen it was safe to come out.
A moment later, Eileen's empty suitcase was under the bed. Then Brad watched her fall onto her back on the bed, reaching out to him with her arms.
"Come here and do that thing with your tongue again," she begged him.
The sight of her spread out on the bed, topless, was too much for him to resist. He climbed on top of her and started a long, hard kiss. She wrapped her legs around him for the first of many times in the coming days. Brad ran his fingers through her flowing hair and ground his erection into her stomach.
"Lick my tits, Brad. Suck on them," Eileen pleaded.
"Not until you undress me, Eileen. I need to feel your skin on mine."
She tried not to act like a crazed teenager having her first sexual experience. Eileen took off Brad's shirt and spent a minute playing with his chest and nipples. Then she rolled onto her side and began taking off his shorts. He wore boxers and Eileen rubbed his hard cock through the material before reaching inside and wrapping her fingers around his cock. Eventually, the boxers came off, too.
Brad was on his back. Eileen slid up his body, more than complying with his request for their skin to touch. She ran her tits over his cock and didn't stop until they hung just inches above his face.
"Now?" she asked.
Brad reached up and put both hands around her tits. Eileen leaned down and allowed one of the nipples to enter his mouth. After a couple licks, Brad sucked on as much of the tit as he could, lightly biting the nipple.
"Oh my God. Yes!" Eileen sighed.
Brad's zeal increased with each passing second until he was sucking on one tit, then the other, with intensity that excited Eileen like never before. Any questions either of them had about their compatibility in bed were quickly being answered. But Eileen's job wasn't just to get Brad hard.
Eileen kissed her way down his body until coming to the stiff cock she passed earlier. This time it would be her tongue that slithered across the warm skin. She licked him several times before kissing the tip of the cock and then inserting it inside her mouth. Eileen clamped her lips around it and began a prolonged, sensual blowjob that Brad wished would never end.
She used her hand, tongue, and lips to make contact with every inch of the erection while Brad watched her breasts roll along with the bobbing of her head. Eileen tucked her hair behind her ears and sucked on the cock until she knew he was almost ready to cum.
Brad's muscles contracted in anticipation of his orgasm. He clutched at the bed covers. Then he put his hands on the back of her head and told her, "Now, Eileen. Now!"
A drop of precum was the only other warning she had. Immediately afterwards, at the same time as his loudest groan, a shot of cum hit the back of her throat. More cum followed and she struggled to swallow it all. Brad thrust his hips up, grunted louder, and deposited the rest of his cum in her mouth. Through it all, Eileen attempted to suck him dry.
Finally, he had to tell her, "That's all, Eileen. God that was good."
She crawled back up to his face and they kissed and rolled on the bed. Brad's hands slid inside the bottom of her bikini and clutched at the soft skin of her ass. He rolled on top of her.
"Tonight we'll fuck until I make you scream," he said.
"Oh my!" she replied. "We have to wait?"
Brad laughed. "Yes. But in return you get to choose how we do it."
She smiled. "You know what I'll be thinking about at dinner."
Eileen did her best to keep Brad's mind on sex by wearing a summery dress to dinner. The top criss-crossed her chest, leaving plenty of opportunity for sideways glimpses of her breasts, and the hem stopped well above her knees. Brad was more than proud to have her by his side.
They shared a table with two other couples, one of which immediately caught the eyes of both Brad and Eileen. Their names were Jill and Evan, and it wasn't Evan that attracted their attention. In fact, he was singularly unfriendly and aloof. But Jill was radiant in a colorful, tropical patterned blouse. Between the plentiful opening she left at the top and the gentle flow of the fabric across her breasts, it seemed certain to Brad she did not wear a bra. His kind of woman, and her personality matched her outfit.
Even Eileen was tuned into her as the discussions continued during the meal. Eileen guessed Jill's age to be around forty five, give or take a couple years. As time went on, she didn't know if Jill was more interested in her or Brad. Either way, she could sense Brad's awareness of Jill growing beyond her nice body. Eileen began to consider the various ways to exploit this unexpected meeting.
She put the first plan in motion when she and Brad returned to the cabin after the dinner and a brief stop at a lounge. Eileen walked out onto the balcony and allowed the warm air to flow through her hair and across her body. It was pitch dark as the ship carved its way through the smooth water. She leaned on the railing just enough to look left and right, making sure nobody else was in sight.
Brad watched from just inside the cabin, mainly paying attention to the effect the wind had on the bottom of Eileen's short dress. Whether Eileen intended it or not, she was tempting him almost as much as the strip she performed in the afternoon. Of course, she DID intend exactly that and it worked.
Brad joined her on the balcony and pressed his body against hers, wrapping his arms around her waist.
"This is my choice," Eileen said over her shoulder. "I want to have sex on this balcony."
"With me?" Brad asked with a grin.
"Of course with you. You can pretend I'm Jill if you want."
Brad chuckled. "What makes you think I'd do that?"
Eileen felt his hands approaching her breasts. "Because I saw how you looked at her. You'd probably give anything to trade my tits for hers."
Brad reached inside one side of her dress and wrapped his fingers around her tit. He pulled on the nipple and felt her body react under him.
"Nope. I want yours," he said.
It had been a long day for Eileen, filled with a little fright at first, then excitement, some sexual build-up that never got released in the afternoon, and finally the meeting of Jill. Now she wanted nothing more than Brad's thick cock inside her cunt so she could have an orgasm, or two, and get on with the night.
Brad, however, was in the mood for foreplay in the darkness of the balcony. He kneaded both of Eileen's breasts, never letting the dress actually fall off her shoulders. As her nipples hardened, so did his cock. The more she pressed back against his body, the more he pushed his erection into her ass. As silently as possible, they teased each other until sex was impossible to delay.
Brad used one hand to reach under the bottom of her dress and find the cheeks of her ass. All he felt was skin at first, until he realized she wore only a thong. His fingers had to search inside and above her crack to find the thinnest string.
"You ARE nasty," Brad told her.
Eileen giggled and felt her dress being lifted. When Brad finally had a view of her luscious ass, he understood how easy this would be. He cupped both cheeks in his hands and squeezed them gently. With the dress securely lying on top of Eileen's ass, Brad unzipped his pants and took out his cock.
He let it rest in her crack, slowly sliding it up and down. Both of them enjoyed the sensation, knowing that the best was yet to come. Then Brad reached around and put a hand on top of Eileen's pussy. He pushed in on the thong and used it to rub her clit. Eileen stifled a moan, but it was obvious she was very excited. Brad's fingers moved inside the thong, collected the moisture from her cunt, and used it to directly rub her clit.
"Damn it, Brad. Fuck me before I go crazy."
Brad pulled the thong aside.
"Spread your legs," he told her.
Eileen eagerly complied and Brad put his cock at the entrance to her pussy. With his hands resting on her hips, Brad gradually pushed the head of his cock inside her hole. Eileen was wet, making the rest of the trip very easy. Brad inserted the cock until he slapped against her bare ass.
He heard Eileen whimper with consent when he started to fuck her faster and harder. The only other sounds were the wind and the wake created by the ship. They seemed to be in their own world, in spite of the very public nature of the setting.
Brad continued to grope Eileen's tits, sometimes directly on the skin and sometimes through her dress. She didn't seem to care how it happened, as long as he kept it up. Five minutes passed blissfully.
Even though Brad was the one paying for the experience, he always preferred to wait for his companion to cum first. Usually he was able to hold out. And this time he had little trouble outlasting the very horny Eileen. Her increased volume and frequency of moans told him she was close.