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Click hereThomas Matthews looked at himself in the mirror and shook his head. "How did I get here?" he said aloud, to no one.
Thomas was a pretty typical 50 year old man. White male, salt and pepper hair, a dad bod (but working on it), glasses for reading and an empty nester. He had a good job as an insurance executive, was well thought of and was well respected in the industry. After 28 years in the business, he had a position that leveraged his accumulated knowledge and relationships and provided generously for it.
This should have been the best time of his life. His daughters were in their early 20s and out of the nest--off the payroll--as he often said. They lived close enough to visit, but far enough away to have their own lives.
Unfortunately, his empty nest was supposed to include his wife, but she was tragically killed in a car accident 18 months ago. The other driver was a wealthy Wall Streeter—a drunk who was going the wrong way on their one way street. Wrong place, wrong time. To say he was crushed was an understatement. Despondent, paralyzed, angry, lonely—all of those words fit. His children had lives of their own, and while they were nearby initially, the "new normal" became just Thomas.
There was initially a lot of press around the incident, but that was quickly buried with the NDA that came with a high seven figure settlement. So Thomas was suddenly well off. After all the bills were paid and some money was set aside for the girls, there was still plenty left, but no one to share it with.
If you believe in the personality type tests, specifically Meyers-Briggs, Thomas was an ENFJ, thus an Extrovert, but really just barely. He felt deeply, and needed some human connection beyond office and client camaraderie. Unfortunately, the introvert tendencies tended to dominate in the months after the accident. He was yearning, silently, for some connection, but for someone who hadn't gone on a first date since 1993, there just didn't seem like there was much hope.
After a few months, he had to make a change---he sold the house and bought an apartment in the West Village in New York City. It's a charming neighborhood of old townhomes, brick streets and small cafes. Families lived there and walked their kids to school. There are parks, sidewalk Christmas tree sales in December, and no skyscrapers. It could have been a charming neighborhood in a hundred cities, but it was in Manhattan.
His home was a charming 2 bedroom/2 bathroom apartment with huge windows, great light and an updated kitchen. It's close to his office, but far enough away that the walk home clears his head. His daughters would come and visit now and then, and a new normal descended upon him.
This change was refreshing, and it gave him a bit of a boost socially. He tried a few first dates, but wasn't comfortable. It wasn't guilt, it was just massive insecurity. He realized needed professional help.
The professional help he sought was not what many would first think of. He sought out paid companionship. There is a whole world of bright, kind and beautiful women who are both exceptional human beings and who have a gift of knowing how to make someone feel "enough". To feel that they are enough as they are and don't need to pretend to be something or someone.
Surely there was someone with whom he could connect and give him confidence and intimacy to bridge the gap between his past and his future.
Enter Sarah.
Sarah is all the things that are attractive to Thomas in a woman---bright, kind, beautiful, a talented writer, a brilliant conversationalist and a wonderful sexual partner. She is an intuitive, loving and trusting woman—an old soul despite her being half his age. They quickly forged a wonderful connection within the context of appropriate boundaries. He was left a little better after each of their times together, and she also became very fond of Thomas. They reveled in each other's successes, supported each other through challenges and neither pushed the other beyond what was appropriate.
She was 5'5", a deep brunette with brown eyes, slightly olive skin from her Mediterranean heritage, the softest skin he's ever touched, magnificent lips, wonderful curves and a smile that you could feel as much as see. She could be comfortable enjoying a fine meal at a new restaurant, drinking a cold beer at a ballgame or sipping champagne with their feet up on the couch.
Over time, as he saw her every three or four weeks, their physical intimacy continued to grow. Each learned the nuances of the other and the few hours together would always be a welcome respite from the ordinary. This was a real relationship, but one firmly bounded by reality and real expectations.
When he decided to book himself two weeks at his favorite spot on earth, Key West, he could think of no one else he'd rather share it with than Sarah. Though this was a significant escalation from three or four hours once a month, she quickly agreed and they easily hashed out the economics, the boundaries and expectations of alone time and such each day.
So as time approached for their trip, the Coronavirus scare really ramped up. There was concern of course, but each had been careful to work from home more often, and were not showing the least bit of any symptoms, so they kept the trip on the calendar.
The day of departure arrived and Sarah was to arrive at Thomas' apartment early in the day where they would relax a bit before heading to the airport. She arrived looking casual but nonetheless as beautiful as ever. Her long dark locks in a ponytail, a casual top with just a touch of a scoop neck to tantalize and tease, and snug yoga pants. A great travel outfit and, frankly, sexy as hell.
After a warm embrace they sat together and chatted for several minutes. Her hands on his knee, his hand gently stroking her arm.
In a moment of quiet in the conversation, her hand lazily, almost imperceptibly, inched up his thigh. His hand slid up her arm to her back and he pulled her to him. They were inches apart staring into each other's eyes.
Who moved to close those final inches first?
Whose eyes fluttered closed first in anticipation of that kiss?
It didn't matter, their lips met tenderly for just a couple of seconds. The kiss was so soft, so sweet—but it also ignited a fuse for a more passionate, fiery kiss that exploded a second later. Stifled moans and the soft wet sound of lips together.
Short of breath
Heaving breasts
Stop to breathe
Pull her closer
Hold her tight
Roaming hands gently caressed her over her blouse and pants. She held him tight to her as his fingertips delicately ran under her untucked shirt and up her spine. Her breath caught as he slid his hands down her sides—grazing her skin with his fingernails ever so lightly.
"I love the way you touch me" she whispered.
He smiled through another kiss as he continued the exquisite torture of these gentle, sensual touches.
He traced his fingers along the waist of her pants, up her spine again and this time slid her blouse over her head and off. Her delicate bra was dispensed quickly and he paused to drink in her beauty.
Firm breasts capped with light pink nipples, which stood out aching for contact. He grazed his fingers across her smooth stomach and up to the underside of her breasts. They were extra sensitive underneath as he'd learned over the past few months. He made her breath catch again by gently caressing the undersides up and along the curve to the glorious nipples on top. He stroked up and down each breast while kissing his way down her neck---stopping to pepper her clavicle with delicate kisses.
His hands and mouth met as he engulfed first one nipple in his mouth, and then the other. Sucking, licking, blowing, teasing.
She was tugging at his clothes in a vain attempt to get them off him—he paused to help by peeling off his shirt and unfastening his belt. She pushed him back and dropped in front of him to relieve him of his pants. His cock sprung out as his pants and underwear were tugged down swiftly.
He was hard and already weeping pre cum. She delicately kissed up his six inches from root to tip before sliding her soft warm lips over his cock. It was always magnificent---that sensation she gave him with her mouth.
Warm
Wet
Soft
Aching and urgent
She slowly bobbed down and up his shaft and led him on an erotic journey that nearly toppled him over.
Seizing an opportunity when she stopped a moment, he suddenly realized she was quite overdressed compared to him. He pulled her up to him gently, and kissed her while his hands reacquainted themselves with her gorgeous curves.
He massaged her butt through her pants, and then slipped his hands inside them. Her skin was perfect---soft but taut, unblemished and hot to the touch. He kissed down her chin and neck, through the valley between her breasts toward her midsection. As he dropped lower, his fingers hooked in her pants to slide them down with agonizing slowness. He kissed each inch down her abdomen toward her silky smooth mound.
Reaching her treasure, his hands pushed her pants the rest of the way down as she stepped out of them.
His head remained at her core, nuzzling her pussy with his nose and gently kissing her most precious space. Lifting one of her feet up on the couch, she exposed herself more fully to him and he began to kiss her labia with more fervor. Savoring each inch with gentle kisses and playful licks, he tasted her sweetness and drank from it like a parched man. His tongue found entry into her flower, reaching as deep as he could while holding her above him.
She moaned---
Breath sharp and uneven
Legs shaking
Core quaking
Hands shaking as they held his head tightly against her. He tilted his head back just a bit and found her clit with his mouth. He toyed with it with his tongue before taking it between his lips with gentle suction. This was taking her to the peak of her passion.
Her voice raising an octave at a time as her orgasm finally took her. "Ohh, Ohh, Ohhhhh!" Trembling and weak she needed to sit---and he held her as she settled back on the couch.
"Oh my, you are so good at that, that was amazing".
"You deserve to be treated to all the pleasure I can give" he replied. Continuing, he said "you ignite such passion in me---I want to devour you in one moment, and worship you in the next".
As she caught her breath, she gently took his still hard cock in her hands and began to stroke it. She too could elicit chills with gentle caresses and gentle kisses.
She pushed him back on the couch and slid up him sensually, ensuring much of his body was caressed along the way by her magnificent lips and breasts. They kissed again, long and deep, as she continued to stroke him.
"I want to taste you again." she whispered. Adding playfully, "is that OK with you?".
Nodding imperceptibly with his eyes closed, he knew what was coming but still that feeling, that heat of her exquisite mouth nearly overwhelmed him as she engulfed him again.
He was not going to last long at this point, and said so, though it sounded more like:
"I"
"ammmmm"
"gnh gonna"
"cummmm"
"nah nah nowwww!"
His mouth froze open and no sound came out. He held his breath for who knows how long as he exploded just as she took him out of her mouth. She stroked him as he fired several ropes of cum onto himself. She stared at these fireworks—"I love to watch you cum" she said with a giggle.
He looked down at her—her bright beautiful eyes and amazing smile were on display, reflecting true joy at this shared passion. She crawled up him to give him another kiss and they held each other for a few moments---soaking up the endorphins.
It was time to clean up and call the Uber---so quick showers were had and they were ready to roll.
Knock knock knock---
"Mr. Matthews? This is Joseph Moreland from the New York Department of Health. We need to speak to you."
"I am sorry but you may have been exposed to COVID-19 through an interaction with a Ms. Lee Jackson at Bella Design. We are contacting all individuals known to have been in contact with her. Apparently Ms. Jackson was in Milan for two weeks and was in the presence of someone who tested positive. I am sorry to say you need to self-quarantine for 14 days. You are prohibited from leaving this apartment except in case of emergency."
Bella Design is a client of Thomas's that has its HQ in Milan. Thomas met with Ms. Jackson two days ago as part of his regular stewardship of their insurance programs. She hadn't said she was in Italy when he confirmed the meeting, or else he would have made it a phone meeting. Shoulda, woulda, coulda....
Mr. Moreland continued:
"This is a list of agencies and services in the area that can make deliveries of medications or food."
"We will be by randomly to check on you."
"Ma'am, I am sorry but you have to stay here too."
"Do you have any questions? Mr. Matthews?"
They stood in silence---if there were crickets in his apartment you would have heard them.
"No, thank you" Thomas finally croaked.
The door closed and they said in unison:
"Ho
Lee
Shit"
This two week Key West fantasy would be a two week apartment lockdown....no brunch at Blue Heaven, no sunset cruises, no Hemingway House and no Duval Street.
Well, at least there was trip insurance, and since Sarah was already committed to that time anyway, it was really just riding out the two weeks. After a moment of collecting his thoughts, he clicked into problem solving mode. Being a male and a Virgo—he couldn't help himself.
"OK, this will be fine! Really!" he said, and started ticking off all the issues on his mind:
"The city has delivery everything...so that isn't an issue. I have a washer and dryer in the apartment, and a Prime membership."
"We can make this work. Plus, let's be honest---if one of us was infected the other is now as well."
"You can write whenever you like from wherever you like in the apartment."
"You can sleep in the spare room or with me, whatever makes you comfortable."
"We can split the cooking."
"I have Neflix and plenty of wine....it's all going to be OK."
He realized he hadn't even let her respond, the oaf that he was.
"Sarah, are you OK?" he asked.
She was not as upset as she thought she'd be, other than missing out on escaping the NYC winter, this could be bearable, more than bearable actually. There was just one thing.
She asked, "Since I will be local, can my cats come stay with us?"
He smiled—"Of course!" knowing how important they were to her.
By the time her brother brought her cats and their things, the shock had passed a bit. That said, their first night together was a lovely but subdued dinner, cuddles on the couch, the late news and sleep---they slept together, naked even, but it was sleep and nothing else.
Day 1
The morning was glorious---sun streamed in and made for a moment's pause---was he not in the Key West now? He heard the toilet flush and water run to fully wake him and he was brought back to reality. He was home, but he was with her.
Sarah was out of bed and freshened up before sliding back under the covers to a warm embrace.
"Hi Lover!" she beamed. "Can we play?"
"Hmmm, I dunno, let me think....." he joked. To which her reply was a smack across the arm. Dashing out to freshen himself up, he quickly returned to a vision.
She was more beautiful in this first light than he remembered. Her dark hair and olive skin a sharp contrast to the crisp white sheets of the bed. She lay there half covered by the blanket with a smoldering look in her eyes.
"Come to me" she pleaded.
He slid into bed and pressed himself against her. His arms ensnared her and their lips met again, as if it was the first time.
Tenderly
Softly
Firmly
Mouths open
Tongues dancing
Breath heaving
"Please" she said, "touch me"
His hands moved over every inch of her.
Slowly
Deliberately
Delicately
Teasing goosebumps on flesh with gentle fingertips, soft breath and gentle kisses.
Her breasts were firm against him, with her erect nipples aching for attention. He trailed down her neck, collarbone, and the side of her breast with gentle kisses—almost like whispers. He kissed further toward the glorious tips of her breasts and gently sucked on her nipples. They stiffened further in his mouth as he teased her there with his tongue. His hands continued to electrify her with delicate strokes as he paid attention to one breast, and then the other.
His fingertips made gentle, lazy circles on her abdomen as his hand inched down slowly. He traced her sides, then in toward her navel and down slowly toward her aching pussy. He put his hand over her mound and cupped it. She was hot and he could feel her wetness. He did not probe, but he continued his delicate stroking over her flower, coaxing it to slowly open and reveal its nectar.
She hummed with pleasure—her body was on fire—and he continued his teasing. Despite being so wet, she gasped when he slid a finger in her and held his hand in her. She ever so slowly ground her hips against his hand as her juices flowed.
Moving to keep his finger in her but to give her some access to his body she, in turn, grazed his skin with electric touches of her own. She teased his chest hair, nibbled on his nipples and trailed kisses down his body.
Pushing the sheets down she revealed his cock, standing proudly, almost angry, aching for her touch.
With agonizing slowness she kissed his member from tip to root and back. Engulfing him a moment, his head was thrown back against the pillow as the sensations were almost too much. But she quickly pulled off and when she pushed her mouth back down on him, she had a condom in her mouth that unrolled as she took him into her mouth. For the life of him he couldn't imagine where it came from, but a nanosecond later he didn't care.
They had been together many, many times, but their intimacy had not yet gotten to this point. For whatever reason, he was not able to make love to her. At first he was scared and insecure. Later he wanted her, and wanted to prove himself, so badly that he got lost in his head. He could never articulate this out loud, but she likely knew, and never pressed him. She was like that—so intuitive and kind. Their chemistry was special, and their intimacy was amazing nonetheless.
But today, in this setting, without the pressure of getting somewhere else, or being someone else, today was the day. She looked at him, this angel who saved him from himself, and straddled his hips with hers.
"Open your eyes, look at me when you go inside me. There will only be one first time for us."
With that, she slowly sank onto him. Her pussy was tight—but soft and warm. Wet velvet quaking as every contour melded into her depths. Their mouths each formed a silent OHHH, while piercing eyes never left each other.
Once all the way down she held still as the relished this feeling---her full and him so blissfully warm.
She leaned forward and kissed him gently on the lips as she began to rock her hips back and forth. The pace quickened over time, and she began to lift off him and drop back down. The gentleness and control of the beginning of this was replaced with fervor and urgency.
Pace is faster
Moans are louder
Sharp breaths
Mangled words
Sweet smell of arousal in the air
Sounds of slick sliding in and out
Then...a pause....
Her orgasm crashed on her like an avalanche. She shrieked, her muscles fluttered as if electric currents pulsed through her, her legs quaked and she fell forward onto his chest, hers heaving with deep breaths.
In a moment she looked at him, still embedded in her and said two of the most powerful words he could imagine at that moment: