Bernie's date was Gail from California. Bernie lived three states to her east and offered to pick her up in his private jet. She easily accepted. Their date was scheduled for Friday. She was to meet him in the airport lobby around three in the afternoon with her passport. He arrived at two. Gail was early and apprehensive. She showed up at two thirty. She said she didn't want to be late.

They had an hour before flight time and ordered a drink at the bar while the pilot refueled the plane. Gail drank wine. He had a gin and tonic with a slice of lime.

The time was well spent. Bernie checked her passport for identification, and asked her how she decided on playing the online reality game. She said she enjoyed a challenge. "Mr. Simmons," she said, "Bachelor4U is definitely my kind of challenge."

"I guess you're right. It's a challenge for all of us," Bernie replied.

Bernie had already invited her to stay with him. He only wanted to know if they were to sleep together or separately. Gail said to table the question until they landed.

Gail was worldly for her age. Bernie decided it was a result of her being a veracious reader. Conversing with each other wasn't a problem despite their age difference. They were on the same page from the very first minute except for one thing. He was a conservative Republican, and she was a liberal Democrat. They agreed to disagree but better yet, just avoid politics.

They took off at three forty-five. At four, Bernie opened a bottle of 2002 Le Mesnil Blanc de Blancs Brut and served hors d'oeuvres . Gail gushed, "Gosh, I don't know a thing about champagne but this is absolutely delicious!"

"Thank you. I'm glad you enjoy it. It has won a few awards. We'll have a proper dinner at the condo. By the way, my friends call me Bernie. I hope we are friends."

"We are friends, Bernie, as long as we don't mention the election," and she smiled a devious smile.

The flight time was four hours, so they didn't reach Bernie's condo until after eight. He had called ahead to the chef. Their dinner was waiting for them.

"Is this really a game like the 'Bachelor', or just a way to get women in bed?" Gail asked.

"Really, Gail, for me it's all about the game. I can't say the same for the others. Guy is divorced and could use some company. Randy is young and always on the prowl. Anyway, it was interesting to compare the responses we got."

"Did you get many?"

"Yes, in fact, I got nearly two-thirds of them."

"Really! And you picked me. Wow, I'm really honored."

During dinner, they talked about literature and music. After dinner, Bernie put on some light jazz. They danced and sipped Cognac.

So what is it, Bernie? One bedroom or two?"

"It's entirely up to you, Gail."

"You know Bernie, I'd like to get to know you better. Is it okay with you if we are in separate rooms tonight?"

"Fine. Keep in mind we need to get up early. We're taking a flight to the Bahamas in the morning."

"You're kidding!" She examined his blank face then said, "You're not kidding."

"Do you have a bikini?"

"No, I didn't know we were going near the ocean."

"It's not a problem. There are plenty of stores selling them. I'll even get a chance to advise you on the best one."

"You want it conservative like you or liberal like me."

"In this case, the more liberal the better," and they both let out a healthy laugh.

It was an early morning flight. They were in the air at eight with breakfast on board. Their destination was six hours away to a private island in the Caribbean The first stop was in Miami to refuel and stock up on provisions. Meanwhile, Bernie and Gail strolled along the beach. By mid-afternoon, they had arrived at a small postage size island. A Land Rover was waiting to pick them up for a thirty minute drive to a beach house by the ocean.

"Bernie, it looks like we're all alone except for the driver."

"Well, Gail, Perry is from Jamaica and more than a driver. He's my handyman, cook and a wonderful sailor."

"But I didn't see any stores or hotels."

"There are none. I own the island. They say that Columbus first landed here when spotting land."

"Where am I going to get my bikini?"

"I'm sorry, Gail. It totally slipped my mind when we stopped in Miami. Actually, you don't need one. Perry is discrete and a full body tan is customary here. Anyway, how about a short nap then a swim before dinner? Perry is preparing a special seafood meal, so we should be well rested at dinner. The swim will invigorate us after our long day."

"I'm all for the nap."

"Okay, the bedroom is around the corner. I'll be on the hammock outside. When you wake up, there is a robe in the bathroom and a towel. Bring them along with you to the beach." The implication was clear. She would be nude under the robe.

Gail had overslept. When she woke up, it was nearly six. Quickly she covered her naked body with the robe and ran into Perry. "Where is Bernie?" she asked.

"Miss, Mr. Simmons is waiting for you on the beach. Please don't worry. We are not slaves to the clock here." Perry was a man about her age with chocolate brown skin, and she loved his soft Jamaican accent.

Gail looked toward the beach and could see a tall naked man with a colossal shock of white hair. Bernie looked as if he had been an athlete in his younger days. He was physically fit for a man of sixty-three. Later she learned he had been an Olympic swimmer.

As Gail walked past the cabana, Bernie turned toward her. She couldn't help noticing his private parts. For a split second, she saw her dad, not Bernie. Growing up, nudity was not an issue in her family, so she often saw her dad naked. In her teenage years, she fantasized about being with older men like her dad. Finally at the age of thirty-four, she had found Bernie to satisfy her fantasy.

He walked up to her and gave her a huge hug. "Did you have a good nap?"

"Yes, but I overslept."

"That's never a problem here," then he gently drew back her robe and let it fall onto the sand revealing her satin ivory skin. "You are absolutely gorgeous, Gail."

It was true. In her younger days, she had been a model. Her face was flawless with dimples and sparkling blue eyes. Gail's breasts were not large but hardly invisible. She was completely shaved.

Bernie took her hand leading them to the water's edge. She dipped a toe in the azure blue ocean. "Bernie, it's not cold at all," then she flew into the waves abandoning all caution.

They splashed and played in the ocean like kids for awhile until Gail threw her arms around Bernie saying, "This is fabulous, Bernie. I never expected anything like this," and she gave him a big wet kiss.

He returned her affections with a bonus. His cock stiffened like bread dough rising in bowl, and she could feel it rubbing against her tummy. "Oh my, Bernie. You have to save that for later," and he knew what she meant.

Dinner was served in the cabana. They didn't bother to dress for dinner.

It was everything Bernie had said about Perry's cooking. He served them a seafood platter on a huge round tray. There was shrimp, lobster, several kinds of fish, and crab legs. The meal was served with a delicious French white wine. They didn't hurry through dinner. Every bite was an event. The two diners savored every morsel.

The sun began to set under the horizon just as they had finished dinner giving them an opportunity to take a short moonlight swim. There was no further discussion regarding sleeping arrangements. They would share a bed on this night.

Neither of the roommates were particularly adventurous in bed. They both knew the basics of foreplay. He had his lips on her pussy. She had his cock in her mouth. She was wet enough, and he was rigid enough. They used the missionary position when he penetrated her the first time. His thrusts were methodical. She enjoyed finally consummating her desire to have sex with an older man.

Gail asked if he wouldn't mind doing it doggy. "I really like it that way best." 

"Of course. Why not?" he answered.

He slipped back into her from the rear. It took awhile before she had her first orgasm. Gail thought it would never happen, but finally Bernie ejected a potent stream of cum into her smooth slick vagina. She didn't bother cleaning up before they both fell asleep until morning.

Gail was the first to crawl out of bed the next morning. She was a little sticky and needed a shower. The warm shower revitalized her, and she was ready to seize the day. Carpe diem. Gail watched as the sun rose over the ocean, and looked down the beach noticing that Perry was in the water. A few minutes later, Perry emerged from his swim. He was naked. Her heart skipped a beat when she saw his glistening bronze body. Most of all, Gail almost fainted seeing his virile attributes. He couldn't see her as she touched herself for momentary pleasure, just before hearing Bernie say, "Good morning. Did you get much sleep?"

"Yes, thank you, Bernie."

During breakfast, they said nothing to each other about their bedroom frolic. Perry served breakfast in the cabana wearing a thong and nothing else. Perry's warm body lightly touched her as he served them coffee and a croissant. It ignited a fire inside her. Gail had never felt so horny before. She began wishing for an hour alone with Perry.

All morning, as they lounged on the beach, Gail couldn't get Perry out of her mind. Finally after lunch, Bernie said, "I'm going to take a siesta this afternoon. How about if Perry takes you out on the boat?"

"The boat?" Gail asked. "You have boat?"

"Well, it's not the Queen Mary but, yes, I have a boat. It's docked in Pirate's Cove on the other side of the island. Perry can take you there."

"Sounds great, Bernie. Can you come along?" Her excitement was transparent.

"Not today. I have a few things to take care of and of course, the nap. Perry will take good care of you." She hoped so.

The die was cast. She wore the robe and nothing else but an alluring French perfume. Perry wore his thong bearing a firm tight ass with a string up his crack. It was almost as if Bernie had arranged this. It didn't matter to Gail. She was determined to take full advantage of the situation.

It wasn't a "boat." Bernie had a yacht that was capable of sleeping eight, a full kitchen, a lounge, a dining area and a sauna. A helicopter sat on the top deck. The first thing Gail did was slip off her robe and relax in the sauna. Perry readied the ship for their sea adventure. Within a half an hour, the ship was underway. The ocean was calm, The sky was cloudless. The sun put sparkles like diamonds on the water. Everything was perfect.

About an hour out to sea, the sun was bearing down on them, and she would be soon burnt to a crisp. "Perry, would you help me with the sunscreen?"

"My pleasure, Miss."

"Oh please call me Gail."

She had already smeared the lotion on her breasts and stomach. She needed help with her back. Perry rubbed her back and continued down to her ass and legs. The erotic sound of the sunscreen squirting from the bottle reminded her of getting a good fucking when she is ultra wet. She was getting there quickly.

Gail turned on her back and asked Perry to add more to her thighs. She spread her legs so it was clear about her intentions. As he worked his way up her thighs, she could see the bulge in his thong had grown so that the small patch of cloth could no longer hold it's contents. The head of his penis was visible driving her mad with lust.

Perry asked, "Do you wish me to go further, Miss?"

She took his hand and placed it firmly on her pussy. "Yes, Perry. I need your help here."

He spread her legs further apart and applied, not sunscreen, but his tongue and lips to her clit. His tongue worked on her like a magic wand. Gail cried out in total rapture. Moisture built inside her, and she was at flood stage, When his fingers penetrated her opening, it was ecstasy. There was only one thing she wanted more than being finger fucked. She didn't need to wait long.

Perry was big when she saw him at a distance on the beach that morning. Now, up close, he was like Harry Reems on steroids. His robust cock entered her sopping cauldron with no resistance. He was thumping and banging into her without hesitation. She moaned. He grunted. They were in harmony the whole time. Orgasms came hard and fast. Her euphoric state sent her to places she had never visited before.

When he came, Perry fired a bazooka-like blast of hot cum into her juicy cunt. She was thankful that it seemed to go on forever. Gail couldn't help comparing his prolonged release to Bernie's the night before. Perry magnified the experience a hundred fold.

"Miss, have I been helpful as you wished?"

"Absolutely, Perry, and much much more."

"Then, let's go for a swim."

Perry had them back in time to prepare dinner. Bernie was awake and asked if she enjoyed the boat. "It's no boat, Bernie. That's the most wonderful ship I've ever seen!"

"So you had a good time?"

"It was marvelous, Bernie. Thanks."

Gail stayed with Bernie for two more days and nights. She fucked Bernie at night and fucked Perry in the afternoon while Bernie napped.

There was one more remarkable event on the flight back to her home in California. Bernie asked, "Gail, are you a member of the mile high club?"

"What do you mean?"

"Sit next to me and I'll demonstrate."

They sat together and he began unbuttoning her blouse, then her skirt and finally removing her bra and panties. She knew the score and helped him out of his pants. She sat on him like in a lap dance, and they screwed over the entire state of New Mexico before arriving in California.

In parting, Gail said, "You know, Bernie. I don't need to win the game. I got more than a cruise during the past five days. You are a beautiful man. Thank you so much."

He nodded with smiled, then said, "Goodbye. You were a delightful guest."