World Traveler Seeks Companion

He paused again, regained his composure and then said, "It has taken me five years to reach a point where I can do as she instructed. I've sold my company. I have the time and the money. Now I'm looking for a compatible companion. I have a sense of urgency. I feel I must get on with my plans before the clock runs out."

Jan nodded and asked simply, "Why me?"

"I want a real experience. I figure I need a real person. I want someone who will honestly enjoy the trip too. I think you will."

Isabella asked pointedly, "Why did you include the requirement about sex?"

"I've thought this through and felt it was necessary. Tell me if I'm off base. There are things I want to do and I don't want my companion's sense of modesty, moodiness or outright obstinate to interfere with me having a good time.

"For instance, if we are out having dinner or drinks and the band plays a song I like, I want my partner to dance with me. If we are at the beach and I need sunscreen on my back, I want her to apply the lotion. If I want to go to a nude beach, I want my partner there, willingly participating.

"I can see some women objecting to these requests. Whatever the reason, she is ruining my dream trip. I figure if she's agreed to suck my dick, she's not likely to object to dancing cheek to cheek, rubbing sun block on me or walking hand-in-hand, buck naked on a sandy beach.

"Sex and nudity are issues that need to be addressed," Sam said. "You'd have asked, if I hadn't brought it up, right?"

"Yes," Jan agreed.

"Some of the trips I have planned will provide less privacy than others. If we end up sharing a room or a ship's cabin, I don't want to feel I have to duck into the bathroom to dress or leave the room to let my partner dress. If she has agreed to have sex with me, the privacy issue is moot."

Sam continued, "I plan on being kind and polite and I hope my companion will behave likewise. I expect there will be give and take on our trip. You go shopping. I'll play golf. You go with me to the museum in the afternoon and I'll take you to the theater tonight."

"Sex is the elephant in the room. If my partner has agreed to sex, many other problems are solved. That agreement negates a whole host of lesser issues and concerns."

Isabella laughed and said, "I can't fault your logic. Although it seems like overkill to ensure that your dance card is full."

Sam said, "I said earlier that I'd give you the straight skinny. I have my likes and dislikes. There are times after a great meal, I will smoke a cigar. I like to watch the sunset while sipping a fine whiskey and sometimes, after a good day, I like to put a woman on her hands and knees and take her from behind."

"Oh!" Jan said. He had painted a vivid picture. She almost felt his hard dick quickly parting her flesh and sinking deep inside her.

Sam noticed that her face blushed a bright red. He asked Jan, "Why have you agreed to have sex with a stranger?"

Jan said, "I asked myself the same question. I don't think of myself as a particularly promiscuous woman. I've had a dozen or so lovers."

Jan took a deep breath to settle herself and explain further. Sam waited patiently. Isabella was shocked by the number of sexual partners her daughter admitted to and how casually she stated it. She said to herself, "I'm twenty years older and I've only been intimate with four men."

Isabella's first lover was her deceased husband, Mike, Jan's father. The fourth man was a kind man she dated three years after her husband had passed away. Two years after she buried her husband, well-meaning friends encouraged her to date. She was after all only forty-four years old. She ignored their advice for months. Finally, she agreed to go on a date with a widower her friends spoke highly of.

Bill, the widower, was in his late forties. He was a handsome, successful businessman whose wife had tragically died around the same time as her husband. They had many things in common and enjoyed each other's company. He was kind and attentive. She slept with him mainly because she missed the intimacy she had had with her husband.

They had sex only once. He was a considerate lover, but she broke things off with him because the coupling lacked the magic Isabella always felt when she was with her husband.

Isabella blushed recalling her other two lovers. Even today, years later she was embarrassed. Three years after the birth of Jan, Isabella and her husband went on a weekend getaway to a winery. They and the other guests had a light lunch and then tasted a variety of wines. A lot of wines.

At the end of the tasting, everyone was feeling the effect of the alcohol. Isabella and Mike were giddy and ready for more fun. It was mid-afternoon. The day was warm and sunny. When someone suggested a hike to visit a nearby picturesque waterfall, Mike and Isabella joined a dozen other intoxicated souls on the trip.

Mike fell in with a group discussing sports. Isabella left his side and focused on the wonderful scenery. She lagged behind the main group. She ended up walking beside a pair of brothers who also enjoyed observing the floral and fauna.

The trio stopped and stepped off the path to observe a cute, little chipmunk. Isabella tripped and fell. She caused Paul to tumble as well and she landed on top of him in his lap. He attempted to catch her and ended up grabbing her breasts. No one was hurt. Isabella laughed at her clumsiness. Her head was spinning so she stayed down.

Paul fondled her large breasts. Isabella was too tipsy to care. In truth, it added to her general feeling of well-being. The wine she had drank made her feel warm and good all over. Paul's touch was gentle and warmed her more.

When she didn't object, Paul added sensuous kisses to the back and sides of her neck. She moaned approvingly.

After the fact, Isabella wished she'd objected that day, but she didn't. She liked it. The young men were good-looking and the alcohol interfered with her ability to reason. It lowered her inhibitions and squelched her normal concerns.

When Tim joined in, Isabella enjoyed it even more. Soon they were naked. She came when Tim ate her pussy. She came again when she rode Paul's cock and she came a final time when Tim took her hard from behind as she sucked Paul's cock.

Isabella woke and found herself nude, sated and with two men in a similar state. Her bum was red from over-exposure to the sun and even more distressing she had a hickey on her right boob. She dressed quickly and went to find her husband. She found him sleeping on the bank of a stream by the waterfall.

The band of merry men and women had found the waterfall. Mike and the others went skinny-dipping in the pool at the base of the fall. Tomfoolery followed and it turned sexual. A flat-chested, skinny ass, drunk chick decided to give all the guys blowjobs. Mike came in her mouth.

She was an aggressive bitch. She grabbed and scratched his ass as she pulled him to her and deepthroated his cock.

Isabella learned this later when she overheard the cocksucking woman bragging about her exploits to a friend. Mike and Isabella never talked about what happened that day. She never asked how he got claw marks on his butt. He never questioned his wife about her sunburned ass or the love bite on her boob.

Isabella shivered recalling that trip. She snapped back to the present when her daughter spoke and explained to Sam why she'd answered an ad that required her to have sex with a man she'd never met.

Jan said, "I answered your ad knowing all that it entailed. I could because I gave myself an out. This meeting. In my mind, I haven't agreeing to sleep with anyone. I'm vetting one possible candidate.

"I have always looked at sex as an act of love. I have been searching for a soul mate or at least a husband. I've given my body to men who I thought were going to be the love of my life. I think I have finally outgrown the fairy tale where I fall madly in love, marry and live happily ever after.

"I'm going to be pragmatic from now on. My vagina is built for sex. There's no harm using a tool for its purpose. People have sex for a variety of reasons: for love, for procreation, for fun, because they feel close to someone or just to knock the horns off. Why shouldn't I behave that way?" she asked with a nervous laugh.

"I think I have been taking sex and life too seriously. The question isn't 'Why sleep with a stranger?' The new Jan asks, 'Why not?' It's not like I have a finite number of fucks in me. Perhaps I haven't been successful in love because I have been giving off a vibe, 'I'll sleep with you, but you better marry me and do it quickly'. I think I need to calm down, chill out and let love find me.

"I'll sleep with you. I'm no longer using my pussy as a honeypot to snare a man. It's a part of me like all the other bits of me. I use my eyes to see. My legs take me places. I will use my vagina for fucking."

Her tablemates stared at Jan. Both recognized that she'd been hurt in her past relationships. They saw that she trying to be a strong, independent woman.

Sam said, "Thank you for being so open and honest with me. You meet all my requirements. How did I do in this interview?"

"You passed," she said with a laugh.

"In that case, will you join me in my room at the Sheraton? It's just down the street. There are a few legal details to take care of and we can discuss the trip."

They walked down the block and up to his room. Sam had a large suite. They sat at a table.

"My attorneys had insisted I address some legal issues. Do you mind if I film our discussion?"

"No," Jan said even though the suggestion unnerved her.

Sam walked over to a camera he had set up earlier and turned it on. Then he sat down at the table and handed them a document.

"This is a recent medical report. I am in good health and free of any STD's."

"Jan, are you healthy and free of STD's"

"Yes."

He handed her a card and said, "Please say your name and age and read the statement on the card I just handed you, if it is true."

"I am Jan Romano. I'm twenty-five years old. I am freely and of my own will agreeing to go on a trip with Sam Spears. I am not being coerced. I am not intoxicated or under the influence of any drugs."

Jan put the card on the table.

"Thank you," Sam said. "I was thinking we'd go to St. Martins in the Caribbean. I'll cover all expense for you, your mother and I for a week in the sun. We will share a villa. You and I will share a bed. You do not object to nudity or having sex with me?

"That is correct,"Jan stated.

"This is a Valentine's Day trip. The 14th is a Sunday this year. We can get a direct flight out of Philly leaving on Friday the 12th and returning on Sunday, the 21st. Is that acceptable? Can you get the time off from work?"

"Yes."

"You both have valid passports?"

"Yes," mother and daughter replied.

"Great," Sam said. He stood and turned off the camera. Then he said, "One last thing. Jan, please stand and strip."

"What?"

"You've told me nudity is not going to be an issue. I don't want to travel 1675 miles and then find out that you haven't been honest with me."

Jan saw his point. She stood and removed her clothes. She placed them on the table and presented her naked body for Sam's inspection. She had full breasts, a plump ass, and a shaved sex. Her dusky colored nipples hardened before his eyes. She even twirled about. She had a single tan line on her lower body.

She said, "You can see I sunbathed topless and I keep my bottoms on. I can make an exception on this trip."

Isabella felt bad for her daughter. She took it as an affront for her to have to get naked. She demanded, "You need to strip as well. You've handed us documents and claim you are disease free. Show us you cock so we can see for ourselves."

"Mother, I hardly think this is some ruse Sam is using to give me a sexually transmitted disease."

"Jan, it's okay. It's a reasonable concern," Sam said.

He stood and removed all his clothing. His flaccid cock nested in his black pubic hair. It was his turned to twirl about and show that he had no boils, rashes or signs of infection on his body. He was a fit man with long, lean muscles. He was tanned except for a pronounced pale area around his hips and upper thighs.

He walked up to Isabella and said without malice or any sign of being perturbed, "Inspect my genitals. If I remember the STD's lecture from my high school health class, you should look for unusual bumps, sores or a discharge. A rotten scent is also a warning sign."

Isabella grabbed his cock. She checked it by touch and sight. She slid her hand over his penis and looked it over top and bottom. He grew hard in her hand. The women discovered that he possessed a normal, healthy, functioning cock.

"Everything seems to be in ordered," the mother said. She was chagrined for having brought the matter up. She apologized, "I'm sorry. I probably took my concern for my daughter too far."

"It's ingrained in your mom DNA. I'm not taking it personally. If everything is in order, you can let go of my dick."

"Oh. Yes."

Isabella released his dick like it was radioactive.

Sam glanced from mother to naked daughter. He said, "Isabella, I need to thank you. This was a good ice breaker. Jan and I were going to be nude in front of each other and now we've done it. It should be less awkward next time.

"Any more questions or concerns? Anyone?" he asked.

The women shook their heads. Sam started dressing. Jan followed his lead. When he was clothed, Sam went to his briefcase and retrieved two envelopes. He handed one to Jan and the other to Isabella. He said, "This is some cash to buy new clothes or incidentals for the trip."

Jan looked inside the envelope. There were twenty one-hundred-dollar bills inside. She gushed, "You didn't have to."

"Perhaps not. I find there are always expenses that occur with vacations. The trip is my idea. I don't want to get things off on a down note by putting a dent in your finances."

He smiled graciously added, "Then if everything is settled I'll see you two at the airport in two weeks. Our flight leaves Philadelphia at 3:40 p.m. and five hours later, we should be in our villa at Club Orient."

^^^

Thursday, February 11th

Jan was preparing to leave her office when her boss popped in and said, "I'm glad I caught you. We have an emergency. I need you here tomorrow for the Smithsonian presentation."

"What?" Jan shrieked. "You know I have a flight to catch tomorrow afternoon."

"Yes. I'm sorry. Randall and Susan can't get back in time due to a snow storm. I need you for the morning. I promise I'll have you out of here by noon. I'll have a limo service take you to the airport."

Her boss shrugged. Jan nodded. She had been working on this project for months. It was important to the company. She reluctantly agreed.

^^^

Friday, February 12th

Jan was frantic as the limo raced to the airport. She wasn't a good flier. The whole process stressed her. She worried about missing her flight and she would be even more anxious on the plane. She didn't understand how a metal object that weighed thousands of pounds could fly. She found the whole experience nerve-rattling.

The curbside baggage guy took care of her luggage and she hurried to the TSA checkpoint. The airport was crowded. The line moved at a glacier's pace. She walked about in stocking feet as her shoes and purse were x-rayed.

She was a wreck when she got to the waiting area. She saw her mother and Sam sitting together. They looked relaxed.

"There you are," her mother said. She stood and gave her daughter a hug adding, "You cut that close. We start loading in ten minutes."

"Hi, Mom. I'm a basket case. The meeting ran late, traffic was horrible. I was worrying the whole time that I'd missed the flight. I'm hungry and have to pee badly."

Sam and Isabella gave her a sympathetic look. One glance at her and you could see she was agitated and overwrought.

"Hi, Sam. Sorry to be so graphic. If you can't tell, I'm in a state and things won't get better for a while. I'm a nervous flier."

She rushed off to the bathroom. When she came out, it was time to board. The flight was uneventful, but that didn't reduce Jan's anxiety. She was continuously on edge. She jumped at every noise and bit of turbulence.

It was 8:30 p.m. before they were settled in their room. Actually, it wasn't a room. It was a beach front, two-bedroom villa with a kitchen, dining room, great room and three bathrooms. They had a front patio overlooking the ocean and their own private, fenced in patio in the back. It was top notch.

"Oh, this is lovely," Isabella said.

"Yes. Wow! Thanks, Sam," Jan said as she looked around. It was bigger than her apartment. The furnishings were luxurious.

"Hungry?" Sam asked.

"Famished!" Jan exclaimed.

They went and had dinner. That was followed by a walk along the white, sandy beach. A bright moon shined down on them.

Isabella said what they all were thinking, "This is paradise."

"Yes. Beautiful," Sam concurred. Then he added, "Shall we turn in? Tomorrow we have nothing planned. I was thinking we'd sleep in and go to the beach after lunch."

"Would this be the clothing-optional beach I heard so much about?" Jan said with a giggle.

When they returned to the villa, Isabella said goodnight to Sam. Jan followed her mother into the bedroom. When they were alone she said, "This place is spectacular."

"Yes. It is a five-star resort," Isabella agreed. "Are you okay?"

"I'm frazzled. I'm on my last nerve because of the hectic day and the flight. If you're asking if I have second thoughts about the trip, the answer is no. Sam has been a gentleman. Everything is as promised. And now I'm going to climb in his bed."

She kissed her mother on the cheek. "Good night. I'm glad you're here."

"Good night, daughter. Sleep well."

Jan laughed and said, "I hope I can sleep. Sometimes my travel anxiety prevents me from having a good night's sleep. We'll see. Night."

Sam was propped up in the king-size bed when Jan entered the room. He was reviewing the resorts amenities. "Do you golf or like to fish or ride horses?" he asked pleasantly.

"I've don't know how to play golf. I don't fish. I do like to ride."

"Good to know. I don't expect us to spend every minute together on this trip. While I play golf or go deep sea fishing, you and your mother can go to the spa or check out the local shops. I'd like you to join me at the beach. We can go snorkeling and horseback riding as well as sightseeing on the island. Plan on dinner together every night."

"Okay."

Jan slipped into the bathroom to get ready for bed. As she brushed her teeth she wondered, "I know we'll be nude on the beach. What about in bed? I guess there's no reason to put it off."

She stripped and walked into the bedroom naked. Sam eyed her appreciatively.

"You are very beautiful."

"Thank you," Jan said humbly.

When she pulled back the cover to climb into bed, she saw that he had on pajama bottoms. She grimaced. "Oh! He must think I such a slut wearing nothing to bed!"

Sam turned off the light and said, "Night."

He rolled over on his side with his back was facing her. She turned off her light and continued to chastise herself. "Good going, dummy!"

An hour later she was still awake. Her mind reeled lurching from one thing to the next. She heard steady breathing coming from his side of the bed and concluded Sam was sound asleep.

"I'm going to be a wreck tomorrow if I don't get any sleep. Why is it that I get so wound up when I fly?" she asked herself.

She slipped a hand between her thighs. She touched her pussy. "I'll not get a wink of sleep unless I rub one out. I need an orgasm to get rid of all this stress and anxiety, but I can't do it here."