Once Upon a When

I

April in Cayman was a pleasant time of year. The crowds of the high season are beginning to wind down. American college kids are back at school nursing their spring break hangovers and lamenting the fresh ink under their skin. The waters surrounding the three islands begin to warm into the 80's and a steady light breeze usually keeps a lid on the tropical heat.

Monique Milan looked forward to this time of year. She worked for an offshore fund administrator headquartered in Georgetown and the onset of spring signaled not only the end of the high tourist season but also her busy season at work. It also coincided with an annual global financial conference on the island that was well attended by financiers from around the world. Monique enjoyed catching up not only the investment managers that her company administered but also friends and contacts she had made at past conferences. Yes, Monique looked forward to April, it made her think of the poem

Spring

, by Edna St. Vincent Millay, especially the ending

April comes like an idiot, babbling and strewing flowers.

Tyler Fox, an investment manager from the United States, went to the bar. The sounds of the waves gently lapping the shore mixed with the ocean breeze rustling the fronds of the silver palms gave him a thirst for rum. The bartender poured three different liquors from bottles he did not recognize over ice, added what looked like orange juice and pineapple juice, added a splash of grenadine, shook it, poured it back into the glass, slid in a straw, and garnished it with an orange slice.

"Fancy" he said to the bartender who smiled his reply.

Tyler struck up a conversation with another conference attendee. She was an attractive woman. Thirty-something, he guessed, with dirty blond hair. The typical networking introduction revealed that she was a compliance professional for a large credit fund based in New York. She smiled and laughed at his jokes.

Monique approached the bar in the company of an older man. They were animated in their manner, laughing, chatting, and generally having a good time. She noticed Tyler right away. He was casual in his manner and his dress, a loose fitting, tropical print shirt, off white linen pants, and brown leather flip flops. He was handsome in his appearance. His shaved head perfectly shaped. His goatee adding just a touch of contrast. Attraction? Perhaps. Distraction? Most definitely.

Tyler also could not hide his distraction. He tried to carry on with the dirty blond to his left but he was drawn to this woman on his right. Her personality was captivating and her sex appeal undeniable. She was tall, 5'8" he estimated, with long dark hair, full lips, and gorgeous eyes behind fashionable glasses. They fell into conversation and pretty soon Tyler had lost interest in the other attendees altogether. He and Monique found a quiet corner to talk and sneak cigarettes and soon their small talk grew larger.

As the party was winding down the driver called out that the last shuttle was heading back to the hotel.

"I can drive you back." Monique offered. She was captivated by their current topic of conversation and was not ready to end the night.

"Are you sure?" Tyler asked. "I don't want to put you out." He continued.

"It's on the way and just past my office." She said. "I'll point out to you."

They made their way to the parking lot where she unlocked the doors to a black Porsche Cayenne. It was the nicest car he had seen on the island.

"Nice car." He said.

"Thanks" she said "it gets me to work and back."

They got in, strapped on their seat belts, and she started the car. She accelerated out of the parking lot and into the road. She pointed to a low rise office complex nearly to his hotel.

"That's where I spend my days." She said. "When I'm not playing tour guide to foreign bankers."

She pulled into the parking lot of his hotel and brought the car to a stop in a space at the far end of the lot. It was darker there and offered some, but not much, anonymity of darkness. She looked at him with her warm, dark eyes. With an unexpected aggressiveness, Tyler leaned in and crushed her lips with his. It was an unexpected burst of passion ignited by an evening of intellectual interchange. Each had become more comfortable with the other as they shared their life experiences, common interests, and embarrassing moments.

"Would you like to come in for a drink?" Tyler asked her.

"I would like to" she replied "but it's late and Cayman is a very small island. If you know what I mean."

"I understand." He said. "I hope you don't think me too forward and inappropriate."

"Very inappropriate." She said jokingly.

As he leaned in for another kiss she opened her mouth to his. His lips were firm yet soft. His was a taste that pleased her, yet its sweetness was imbued with a hint of cigarettes. An oral reminder of other small sins committed in their short time together.

"Will I see you tomorrow?" He asked anxiously.

"Most definitely." She answered.

Tyler smiled and exited the vehicle. Monique leaned back against the head rest.

What the hell am I doing

? She thought.

The fact was, over the last couple years since her divorce Monique's libido had shifted into overdrive. Her sexual appetite since turning 40 was proving to be insatiable. When she first started noticing, she worried that she may have a chemical imbalance. She had a few on again off again boyfriends and had always enjoyed a satisfying sex life. Only, recently, she had not been completely satisfied. She found herself masturbating much more often than she ever had and fantasizing constantly.

The next morning Tyler burned through his rum induced fog with strong coffee, a toasted sesame bagel with cream cheese, and a banana. He made his way into the ballroom and settled into a chair at a table in the back corner. Once seated he opened his notebook, pulled out his pen and smartphone, and looked around the room. He hoped to spot Monique in order to position himself to randomly run into her at the break. His initial attempt to survey the room proved unsuccessful. She was nowhere to be found.

Tyler returned after the break to find his previous table to be full so he grabbed a spot at the next table over. At his original table, in the chair directly next to the one in which he previously sat, was a woman in a striking blue dress. Her long dark hair looked familiar.

Could that be her?

Tyler thought to himself. He shifted in his seat to try and get a better look. To get a glance of her face.

Monique had spotted Tyler as soon as he walked through the foyer Tuesday morning. He seemed to be walking in sort of a haze but she was impressed that he made the first session after they closed down the bar the night before. She thought that he might sit next to her in the ballroom but he was oblivious.

Typical guy.

She said to herself. When he did not notice her at the break she decided to take matters into her own hands. She went back into the ballroom early and planted herself in the seat right next to the one where he sat the first session. Only he didn't show.

WTF?

She thought.

Is this guy purposely avoiding me?

Her table filled and in her annoyed state she did not notice that Tyler had come in late and sat himself at the next table.

He approached her at the end of the session flashed his casual smile and commented how happy he was to see her. It warmed her to hear the words.

Now WTF is wrong with ME?

She wondered.

Am I crushing on this guy?

"Would you care to sit with me for lunch?" Tyler asked her.

"Yes, yes I would." She replied with her own sexy smile.

They enjoyed a lovely lunch catered by the hotel. They each made small talk with the respective attendees to their immediate right and left. And as the lunch was winding down, Tyler leaned over to Monique.

"Are you going to the beach party after this?" He asked her.

"I don't know" she replied "I have been out late the past couple nights."

"It would be nice to see you" he said "to spend some more time with you."

"I'm glad to hear you say that" she said "I'd like that to."

There was a nervous energy between them yet it was also seemingly comfortable.

Monique arrived casually late to the beach party after catching up on the calls and emails that had piled up while she had been out of the office. Tyler saw her straight away and smiled. She had an effect on him. His smile drew her to him.

"I was beginning to think that you were not going to make it." He said. "I'm so glad that you did."

"I had to tie up a few loose ends at the office." She replied.

She did not mention the small fight she had with her current boyfriend about her going out for the third night in a row.

After all this was business.

She thought.

Wasn't it? Or maybe it was pleasure...OMG, it IS pleasure. I'm so fucked.

II

Summer in the city is a test of one's attention span. The heat lays upon you like a blanket, the humidity soaks your most private cracks and crevices, the crowded streets bustle with businessmen, tourists, touts, and hustlers. The city itself feels alive. Manhattan: an island one third the size of Grand Cayman; with thirty times as many people. The city reeked of opportunity; and rotting garbage. Apparently the sanitation workers had went on strike that week.

Monique arrived at JFK in the late afternoon. She had cleared customs in Miami so she only had to stop by baggage claim, grab her bags, and hop a cab into the city.

"The Sanctuary hotel please" she stated "between 6

th

and 7

th

Avenues."

"Yes ma'am." The cabbie replied.

With that they were on their way into Manhattan. They drove down 278 to 495, across the East River, and through the cavernous streets and avenues that crisscrossed the island. As the cab brought her closer to her destination she got more and more excited about her opportunity to finally explore her crush.

The cab stopped upon arriving at the Sanctuary. A hotel that she was not familiar with but Tyler had assured her that it would be perfect for their rendezvous. She swiped her credit card in the reader in the back of the cab, adjusted for a tip, and asked for a receipt. The cab driver pulled her bags from the trunk, handed them to the bellman who had opened the cab door, and thanked Monique for the fare.

It had been a long day of travel. She looked forward to settling into her room, pouring a cold glass of chardonnay, drawing a hot bath, soaking and sipping away any lingering feelings of guilt for what might happen. For what she hoped would happen. After a quick stop at the front desk, she had her room number and key card and was walking to the elevator. She entered, pressed the button for the 19

th

floor, and up she went. She exited and made her way to her room.

Tyler caught the 5:00pm Acela from Washington's Union Station. It was scheduled to arrive at New York's Penn Station at 7:49pm and they were a few minutes ahead of schedule. He could barely contain his excitement. Monique had lit a fire somewhere deep inside of him. He was not looking to complicate his life but she was an itch that he had to scratch. A treat that he had to taste.

When the train came to a halt in Penn Station Tyler alighted and made his way to the Madison Square Garden exit. He pulled out his phone and fired up Uber. Within five minutes of leaving the station he was in a black sedan and on his way to the Sanctuary. He was grinning from ear to ear when the Uber driver asked him what he was in town for.

"Business" Tyler said "and pleasure" he added with a conspiratorial laugh.

Monique had emailed Tyler the room number so he by passed the front desk and went straight to the elevator. He nearly skipped through the lobby. Inside he pressed 19 and took a deep breath.

Well, here goes.

He thought. He got to the door, took a quick glance down the hall, not expecting to see anyone, just reacting to a spontaneous tinge of paranoia, and then knocked. Monique opened the door wearing a white terry cloth robe. She had finished her bath and was relaxing on the plush, pillow topped bed with leather headboard, watching TV and sipping her second glass of chardonnay.

"Wow" he said "you look good enough to eat."

"Well maybe if you play your cards right..." She replied coyly.

"I know when to hold 'em" he said "and when to fold 'em" he continued "but I'll be damned if I'm gunna know when to walk away from you!"

He reached behind her back, pulled her into him, and kissed her hard. After a long, deep, passionate kiss, that had Monique melting into his arms, he pulled back.

"That's nice" he said "but I want to rinse and relax. Why don't you watch a few more minutes of TV and warm us a spot on the bed?"

"Do I have to?" She asked rhetorically as he turned and went into the bathroom.

Tyler turned up the heat and stepped into the shower. He lathered himself with the bar soap provided by the hotel. Any misgivings that he may have had were washed away in the heat of the shower. He turned the knob to the off position, grabbed a thick white bath towel, and dried himself. Toothbrush, toothpaste, deodorant, and then cologne. He felt clean. Refreshed.

He walked back into the bedroom wearing only the towel. He made his way to the king sized bed where Monique was passing the time watching some reality show. She was laying on her left side with her right leg crossed over, right foot flat on the bed, right knee raised. Her skin was exposed beneath her robe. Tyler reached out and stroked her right thigh with his left hand. Monique rolled her eyes from the television to his face. They held each other's eyes. The desire was palpable.

Monique grabbed the remote, clicked the off button, and stood up. Her thick, white, terry cloth robe opened as the loosely tied belt came undone. Tyler reached in with both hands, sliding them around her back, and onto the top of each perfectly shaped ass cheek. He squeezed as he pulled her closer to him.

"You are SO sexy" he said "I could just melt into you."

"I wish you would." She replied.

With that, he reached behind her head with his right hand, running his fingers through her hair, and pulling her head towards his, her face into his, her lips onto his. Then he pulled back.

"I've imagined this kiss a thousand times." He said.

Monique backed away, placed her thumbs under the shoulders of her robe, tossed it back and let it fall to the floor. She stood before him completely naked. Vulnerable. Staring into his eyes. Awaiting his next move.

She did not have to wait long. Tyler stepped to her dropping his towel in the process. He embraced her. As his naked body pressed against her she felt a pulse of what she deemed sexual energy from her head down to her toes. Her body was charged. Electric. She wanted him.

Tyler sensed her desire, when she shuddered ever so slightly when he held her, when the hairs on her body stood on end, her goose flesh revealing secrets that she had hoped to keep bottled up inside. Yes, she wanted this man. She wanted him to make love to her. To fuck her.

He slid his right hand between her legs, parting her thighs, so that she stood with her legs shoulder length apart. His middle finger split her labia, his index and ring fingers gently massaged the outer folds. She was wet. Soaked, in fact. Her longing for him highlighted in her physical reaction. She rocked her hips unconsciously as he penetrated her with his finger. She wrapped her arms around his neck and kissed him deeper.

"Fuck me" she said "I want you to fuck me."

Without offering a reply, he laid her back on the bed, spread her legs with his left hand, while his right hand found her left breast. His full hand cupped and squeezed her breast. Then his thumb and middle finger pinched and pulled the nipple on that breast. Her physical response was for both nipples to become erect. She reached up and grabbed his head. She pulled his face into her bosom. Between her breasts. His lips found their way to her right breast. His tongue encircled the nipple. He replaced his lips with his left hand. Caressing. Squeezing. Pinching. While his mouth kissed across her chest to her left nipple.

Monique was getting even more turned on. The sensation spread through each of her erogenous zones as he explored the sensitivity of her body which was hyper-responsive to each nuance of his touch. She closed her eyes, tilted her head back, and he slid up her body to plants kisses up the middle of her neck, around its left side, and up to her ear. The heat of his breath sent tingles down her spine.

As he was kissing her neck, Tyler reached up behind Monique, and grabbed each of her wrists. He held them firm as he laid a trail of soft kisses and wet licks down her neck, across each breast, to her navel, lingering for a moment, before continuing on below. Monique squirmed in anticipation. She grinded her hips against his chest hoping that he would hurry up and stick his tongue between her legs. Unfortunately for her he was in a teasing mood. He stopped at the top of her perfectly trimmed pussy, kissing the skin just above, and the recently waxed bikini line on each side. Monique could feel his breathing in the hair of her pussy. If he wasn't holding her wrists she would have reached down, grabbed his head, and pulled his face into her.

"What are you waiting for?" She asked.

"What do you want?" He asked in reply.

"What the fuck do you mean, what do I want? I want you to lick me. And if you'd let me go I'd make you." She said in a labored voice.

With that, Tyler began to slowly lick lower. He lightly licked the edge of one labia from the bottom to the top, and then the other. He barely brushed the outside of her clitoris as he transitioned from one to the other. Then with slightly more pressure from his tongue he split her labia and licked the middle of her vagina bottom to top. This he did three times. The third time he stopped at the clitoris and licked. He circled it with his tongue. He softly sucked it in his lips while using his tongue to stroke it. She began to squirm with more force, bucking her hips ever so slightly. He let go of her wrists and she instinctively reached for the bald head between her legs and pulled while driving herself onto his face. Her rate of breathing increased, and her moans got louder, as she was nearing orgasm. Sensing this, Tyler stopped his oral orchestra.

"I want you to come with me inside you." He said.

"Then you better stop teasing me and start fucking me." She answered with a pant.

He stood up leaving Monique lying on the bed, legs spread wide. She leaned up on her elbows and stared at him standing before her, naked, erect. His cock was magnificent, slightly larger than she was used to, but not overly so. She had a sudden urge to take him in her mouth, to taste his manhood, to swallow him whole. She started to make a move to do so when he stopped her by showing her the palm of his hand.

"Stay there" he said "turn around."

She looked at him for a second while his words registered in her mind. The look on his face was without humor, it was not quite warmth, but commanding, expecting, intense. She decided to obey without reply. She rolled onto her stomach and pushed herself up onto her hands and knees. She turned her head back to the right to look at him. His intense look softened, ever so slightly, his lips, while not quite curving to a smile, had warmed to, perhaps, a flirty smirk.

"Clasp your hands and slide them out in front of you" he said "and press your tits to the bed."

Monique complied sliding her arms on the sheets.

"Now raise your ass" he went on "I want to take you from behind."

She did as he commanded. Her arms were outstretched, flat on the bed, her tits were pressed into the bed, her ass was raised in the air, waiting, wanting, inviting. He climbed onto the bed behind her. He reached up with his right hand and grabbed a handful of her long, dark, hair. He grabbed the base of his cock with his left hand and guided it to her vagina. He placed the head of his dick on her labia. When he pressed, ever so slightly, he felt the warm, moistness of her excitement. She was beyond turned on at this point. She rocked back onto his dick, her labia sliding over the bulbous head of his penis. She paused for a moment as he entered her.