The rain debated its permanence for hours that day. Clear sky gave way to downpours that dwindled to a heavy mist and then resolved once again in full sunlight. It was to be expected this time of year along the coast, but it complicated her plans for the evening all the same.
No matter, she told herself. Complicating factors were not always bad. Obstacles that invite challenge often heighten the reward. Jamie thought of this as she walked through the thick May air of the early evening. As she navigated the wet sidewalks that led to Connolly’s Bar, she looked out over the harbor. She saw the breaks in the clouds that were slowly making their way east and felt a small sense of relief.
This was not her first time starting a new relationship. Still though, Jamie experienced the small gnaw of panic that festered in the bottom of her belly as she approached the bar where she planned on meeting her new someone tonight. She worried that she would say the wrong thing or that her usual black attire would turn be a turn-off. With a deep breath, she pushed all these thoughts away and stepped inside. The warm darkness of the bar’s foyer comforted her, and she knew it would all work out.
Connolly’s had become Jamie’s place, an unexpected retreat. As the head curator of the new contemporary art space just a few blocks away, Jamie had spent many hours at the corner table nursing beers while writing art reviews. She could safely escape there and finish her work in peace—left alone to think and relax. Primarily a bar frequented by the boatyard workers next door, Jamie loved the authenticity of the place. It smelled of men and beer. The loud banter that followed these men from their work offered her a kind of serenity from the high-pressure intellectual conversations in which she was expected to engage during her days. The bartenders and some of the regulars had even come to know her and welcomed her, which only deepened her affection for the place.
As Jamie’s eyes adjusted to the dim light of the bar, she scanned the room. It was already crowded, but she found a tiny opening at the bar where she could order her beer. Jamie squeezed up to the bar and ordered her favorite local IPA. As she did, she noticed the looks from some of the men around her. While not exactly parting for her, they did shift, perhaps hoping to get a better look. Her black skirt fell above her knee and her black boots fell just below. Her trench coat still cinched tightly around her waist revealed her ample curves, no doubt adding mystery to what was beneath. As she found a small table near the porch overlooking the harbor, Jamie felt the men’s gaze linger. Relishing it, she slowly untied her trench and let it slide over her shoulders and down her back. She hung it over her chair and, clad only in a silk tank, turned to give the group a smile of acknowledgment. Their interest gave her the confidence to know that tonight would be a success.
It had been months since Jamie had sought out anyone. She met her last lover at a gallery showing, an easier venue than Connolly’s. But their relationship had become wrought with too many emotions, so she had ended it — just as she had said she would if things became too complicated. It was messy and hard, but necessary. Finding a lover here, however, at a bar full of men who looked upon her with a novel curiosity, would be a first for her, and she had decided weeks ago that the excitement of it all was worth any anxiety that it provoked.
But then there was the part of having to explain what she wanted from her lover. She wouldn’t have to do that tonight, but soon. The rain, the meeting—that was easy. Having him understand that she was happily married to Ben, and that what got Jamie off was having him watch her fuck another man was more complicated. A well-heeled intellectual woman was not supposed to like those things, but here she was. And she did like it—very much. She had done it all before and had to assume that she could do it again.
Jamie settled into her cozy corner, positioning herself so that she had vantage points of both the harbor and the bar. She took out her iPad and began scrolling through articles that she was scheduled to review and edit. Most nights, she would have been able to focus on them, but tonight, anxiety got the best of her, and she gave up. She scanned the bar, which continued to fill as the 5:00 hour neared. At the far end stood five or six men, all wearing Bay Street Boatyard T-shirts, stained and dirty from the day’s labor. Thinking of the physicality of the men’s work, she felt the rush of excitement. Their t-shirts stretched around their biceps and thick chests, and the tug of her desire grew.
As she watched them, one caught her eye. Maybe it was the soft cappuccino color of his skin or the golden-flecked curls of his otherwise dark hair. Whatever it was, she could not look away. He stood at the edge of the group, laughing with them, but clearly not fully engaged; his gaze would wander, looking out over the tables to the open porch and the harbor beyond. Despite the increasing raucousness of the bar, he maintained a calm tranquility around him that Jamie couldn’t ignore. She was taken. He was the one she wanted. Of all the men in the bar, her art-trained eye landed on him and refused to leave.
She shifted her body in her seat, switching the cross of her long legs, all in the hopes of gaining his attention. As she imagined her body against this man, she felt the heat rise in her and took the last sip of her beer. The collection of silver bracelets that she so carefully chose every day slid up her arm and made a soft metallic clank. She loved the feel of the metal against her skin; given her rising interest in her man across the bar, the feeling only heightened the excitement that was building inside her.
Pushing her empty beer glass aside, Jamie bent down to put her iPad back in her bag. As she rose again, a chunk of her thick hair fell out of the messy bun she had wrapped at the top of her head. She tucked it back behind her ear and looked in his direction one more time. And this time, he was looking back.
Even half a bar away, Jamie could feel the power in his eyes. For a moment, his eyes left hers, perhaps embarrassed to be caught. Jamie’s eyes, though, did not waver. When his gaze returned, she smiled and gave the slightest nod. Again, she switched the cross of her legs, letting her skirt move higher up her thigh, where it would stay. The paleness of her skin contrasted with the black made noticing her toned thighs unavoidable. His gaze lingered.
She leaned back in her chair and let him take in her whole body. The silk of her tank top showed off the shape of her ample breasts. Underneath, she could feel her nipples begin to harden. The thought of his hands cupping her tits and bringing them to his mouth electrified her and made her once again shift in her seat.
She would have him.
Now, she had this man’s full attention. His friends’ conversations had slipped into the background for him, and his mind was only on her. With every sip of his beer, the softness in his gaze that had scanned the bar earlier revealed a new intensity. He never took his eyes off her, perhaps fearing that she would disappear if he were to lose sight of her, even for just a moment.
Looking away, Jamie reached into her trench coat pocket and pulled out her phone. A quick text to her husband — ‘Be out in 20’ was all she needed to say. He would know what to do and where to be. As always, sending the text sent a new wave of exhilaration through her that released a pool of wetness between her legs. Her mind began to race with images of her and her new lover that she struggled to quell. Sliding the phone back into her pocket, Jamie stood.
It was hard to ignore her presence as she walked across the open floor. With relatively few women in the bar, as well as her tall statuesque figure draped in her silver necklace and bangles, she attracted more than a few glances. She walked slowly, absorbing the attention. As she approached the bar, he turned towards her. But she deliberately ignored him, squeezed in next to him, and waited for the bartender. Despite the closeness of this man who clearly wanted her, she resisted any temptation to acknowledge him. After the intensity of their connection from afar, being so close without a word or gesture was painfully electrifying.
“Can I buy you that one?” he asked after Jamie ordered another beer.
Jamie shook her head.
“I’m Simon,” he offered, persisting, but with a hint of confusion in his voice.
“Jamie,” she said, still looking straight ahead.
Now that she was close to him, she could tell just how young he was. Mid-twenties, maybe.
“Are you here often?” he asked, breaking the sea of silence between them.
“Yes. I like to come here after work,” was all she offered.
“I just started at the boatyard. They brought me here.” Simon gestured to the group next to him, now keenly aware that their friend was talking to this unexpected and clearly older woman.
“I’m glad,” she said.
She finally smiled in his direction and looked into his eyes. They were a clear deep green that nearly took her breath away. She let go of her beer that she had been cradling between two hands, reached down under the bar and grasped his thigh. Through his heavy duck canvas work pants, she felt the muscularity of his body. There was no doubt in her mind that she wanted him now. She felt him shift his weight, towards her. Her hand moved closer to his crotch. She grazed his cock, certainly becoming hard with her proximity.
“Do you want to sit?” he asked.
“No,” Jamie said, taking a long drink from her beer. A slight tingle of relaxation echoed inside her as her third beer took hold. Grateful for the feeling, she knew it would make everything a little easier.
“OK,” Simon said, hesitating.
Jamie waited a moment, then leaned into his ear and whispered, “I want you.” She smelled the sweat on his neck and felt herself falling deeper into her pool of need. “Do you want me?” she breathed into his ear, grabbing his crotch firmly under the bar.
It was a simple direct question. Perhaps an unexpected one, but an obvious one, Jamie thought.
“Yeah… I mean…” Simon stumbled on his words as a smile broke across his face. “Of course, yeah,”
“Good,” Jamie said. She took her hand from his crotch and looked directly at him. From there, she could see how beautiful he truly was. Despite his obvious strength and familiarity with physical work, there was a softness about him that drew her in. It was all she could do to not reach over and begin touching every part of his body.
Jamie put her money down on the bar for the beers. She said, “I am going to grab my jacket and bag and leave. If you want, you can follow me. Meet me at the edge of the parking lot, closest to the boatyard.”
Not giving him time to respond, she turned and walked towards her table. She grabbed her things and headed towards the door. She turned only once, briefly, to look. Simon was leaning back against the bar, watching her, his eyes piercing and beautiful.
Outside, the night air remained heavy with moisture and had taken on a chill that cut through her jacket. Jamie walked to the edge of the parking lot, bounded only by a few large rocks, and waited. She turned and looked out over the then quiet harbor.
She heard the crunch of gravel and felt Simon’s hands pull her hips backward. “Hi,” he said, as she turned to look at him.
“Hi,” she said, pushing him away despite her body’s longing for the heat that she felt even with the layers of clothing separating them. “Not here,” she said, taking his hand and leading him around the rocks into the boatyard.
Jamie wove her way around the boats being readied for summer. Floodlights spotted the inky darkness with rounds of orange light that she walked between as she headed to the nearest corner of the main building, a huge green metal square structure. Except for the side that faced the small street behind the boatyard, Jamie and Simon were surrounded by boats. The usually deserted street had but one car, parked in the shadows. It was unsuspecting enough, but Jamie knew that in the car, shrouded in darkness, Ben sat, watching. And knowing that was all she needed.
“Better,” Jamie said, smiling and pulling Simon close to her. “I want you here.” She pushed his yellow rain slicker off his shoulders and down his arms. Her hands immediately found his chest and she felt the power of his body.
“Really? Are you sure?” In Simon’s voice, Jamie heard his readiness, but also the faint hint of apprehension. “My apartment is nearby… If you want,” he continued. It was clear, though, that waiting was becoming less of an option for him, too. He pulled Jamie to him hard and kissed her deeply, not waiting for her answer. His tongue was thick and warm and tasted of beer and salt. He probed her mouth as his hands held her head firm.
Jamie accepted his kiss as her hands found their way under his shirt. His skin was smooth with only a small trail of hair that led from his chest down to his belly button and beyond. She traced it with her finger, and hooked her fingers into the waist of his pants, pulling him into her.
Simon’s hands slid down her body and fumbled with the belt of her trench coat. As Jamie pulled away from his frantic kiss, she turned her head to peer across the street to where the lone car sat. Now that her eyes had fully adjusted to the darkness, she saw Ben’s figure in the car. His shadow made it clear that he was watching his wife. She saw the slight rhythmic movement of his shoulder and arm, and she knew he was beginning to enjoy what he saw.
Knowing this sent Jamie into a new frenzy. Her wetness had soaked her panties, and she could feel the rising tide of ecstasy. Just the thought of Ben stroking himself in the car while watching her was enough to make her explode, but she had done this enough to know that she had to control her mind just a bit longer to reap the full intensity of the moment.
The cold air hitting Jamie’s shoulders as he pushed off her trench brought her back to her place in the boatyard. Simon was quick. His warm hands moved under her tank with a deft awareness of her body. He explored her breasts and felt the hardness of her nipples with his thumbs. Pushing her bra and shirt up, his hands stroked the softness of her skin, before lowering his mouth to them.
As he tickled her nipples with his tongue, Jamie’s head fell back. She inhaled deeply at the first sensation of his warm mouth on her body. She held his head and guided him around her tits, pushing his head into the soft ample flesh of her chest.
“Bite,” she instructed.
His eyes searched her and then obliged. It was a gentle nibble at first that grew in confidence and strength as Jamie’s breath became more urgent. She felt the grip of excitement tightening around her, and she focused herself to once again look over towards Ben. His silhouette was still stoic in the car, except for the constant motion of his shoulder, now more obvious to Jamie as she turned her focus back to Simon.
“Stop,” she moaned, pulling away from him. He looked up at her obediently. Jamie’s hands quickly moved to his cock. Thoughts of her husband’s hard cock made exploring Simon’s that much more exciting. As she pushed him upright, she unsnapped and unzipped his pants. The bulge in his pants made it difficult for her to pull his pants down enough to get a good look. But after a brief fight, she had wiggled his pants down enough to grasp his hard substantial cock.
He let out a simultaneous shiver and groan. “Sorry,” she whispered, as she realized how cold her hands were against the heat of his skin. Jamie began stroking his cock harder and faster.
“Don’t stop,” was all Simon said, as he found his way to the bottom of her skirt, which he desperately pulled up above Jamie’s hips.
With his calloused hands exploring her ass and pulling on her thong, she felt her body racing towards climax. As Simon pushed her underwear aside, he spun her around and pressed her against the building. The cold wet metal of the corrugated siding sent a jolt through her body that reset her urge to come, at least temporarily. But his roughness was intoxicating. And not only for her. Ben, who had a penchant for rough sex, was seeing her being pushed up against the building. She knew that he was undoubtedly rushing towards his own climax, and this again forced her to the brink of ecstasy.
Simon had his fingers pushed deep into Jamie’s pussy. Her wetness was everywhere, and Simon’s exploration only spread it. As his fingers delved into her, his palm adeptly massaged her engorged clit. With every plunge of his fingers, a loud moan escaped from deep within her. Her hips thrusting into his hands, Jamie continued to jerk Simon off with an intensity that caused him to shudder and moan, too. Her mind flashed back to Ben and the idea of bringing both of her men to climax.
“Get inside of me, now,” she said through clenched teeth, her voice low and demanding.
Wordlessly, Simon picked her up. Her long legs wrapped around his hips like a vine, searching for stability. He plunged inside of her. “Fuck,” he murmured. With his hands grasping her ass, she slammed her pussy into his cock. It filled her, and she emitted a small squeal as he stretched her further apart than she had expected.
As Jamie rode him, her hair fell around her shoulders. She tipped her head back and caught a final glance at the car. Inside, Jamie could tell that Ben was at his breaking point; she saw that both of his hands were now pleasuring himself, that his stroke mimicked that of Simon and Jamie’s movement.
She would not take her eyes off Ben now. She would feel and listen to Simon, holding herself tight against him, his body taking on a power and life of its own. She would listen to Simon’s breathing, now shallow and fast. But Jamie’s mind and eyes would remain on Ben. She watched the frantic speed with which his shoulders pumped until he froze. It was only for a second, but in that moment, everything needed to fall in synch.
As Ben’s body seized with his come in the car, Jamie gave up her final grasp of control. “Come now, Simon.” Her whisper was tense. “Come. Come. Now. Now,” she implored him between gasps as she, too, felt the wave of orgasm wash over her. The strength that she possessed at that moment overtook Simon’s rhythm, and her hips followed Ben’s movements as she imagined seeing him explode.
Jamie rode her wave of pleasure from Ben to Simon. As she pounded her pussy into Simon’s hips, she felt his come burst into her. The sudden increase in hot wetness inside of her sent her into a new feverishness, and she came again. She felt Simon’s grip slip briefly as the power of his ecstasy rendered him weak.
“Don’t stop,” she pleaded with Simon. “Come. Come.”
Simon buried his face into her chest and moaned. Over and over again, he shot his come into her, until he was spent. “Fuck,” was all he could muster.
Jamie felt the sweat between them as he finally lowered her down. He stood and looked her in the eye and said nothing.
She smiled as she pushed her skirt back down over her ass and picked up her trench coat and bag. “Thank you,” she whispered. As Simon pulled up his pants, she brought her hand to the soft skin of his cheek. She softly kissed his lips.
“What now?” Simon asked as he took her hand and once again pulled her close to him.
“I’m sorry. I really have to go,” Jamie said.
Those moments were still the most difficult. The guilt wound its way into her being every time. She would tell Simon everything, she just couldn’t explain it now. She needed tonight to be just as it was.
As she glanced one last time over to Ben’s car, she saw him sitting motionless, hidden to everyone except her. Jamie leaned into Simon’s ear, kissed it and whispered, “Next week.”