Thomas 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.
