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Struggling to Sleep, Part 2

In Sara's city, Shawn has an hour to pass.

Spankmasters
May 13, 2024
15 min read
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Can't Sleep Pt. 02
Can't Sleep Pt. 02

Struggling to Sleep, Part 2

Shawn beamed as he thumbed through his recent messages. These were messages he exchanged with Sara.

It had been close to a year since that fateful evening when they hooked up in Nia and Scott's basement. It was also almost a year since Sara returned home and got engaged to her boyfriend within a few hours. Sara had added Shawn as a friend a week later and sent him a message.

"Can you call me?"

Shawn took a while to answer, promising to call and then taking even more time before he finally dialed the number Sara provided immediately afterwards.

"Hello?" Sara asked on the other end. Her voice sounded distracted.

"Hi Sara, this is Shawn. I was just calling like you asked, but you sound busy..."

"No, no, no! Let me find a quieter place." Shawn felt a flutter of nerves as he waited. The rain was coming down lightly outside his window, mirroring his mood. After what felt like an eternity, Sarah retrieved the phone and said:

"Sorry, I was on the stair climber at the gym. I thought this was a spam call."

"Nope, just me," Shawn smiled. He breathed more easily, settling into a nearby chair. "You said you wanted me to call?

"Right," she exhaled. "Look, Shawn, I want to tell you I'm sorry."

"Sara, you don't need to apologize..."

"I do," she countered. "I didn't expect this conversation while I was at the gym and didn't expect you to find my Facebook and like my post." As her breathing returned to normal, she continued. "I went downstairs because Nia had been talking about you constantly all weekend. I was curious, so I went to find out for myself."

"I thought you and that guy were engaged?"

"We were! And we'd been together for over a year."

"Not anymore!" Shawn chuckled at the idea of Nia and Scott scheming to get their friends together.

"We broke up a month ago and hadn't heard from each other until that day. And then came you."

"I'm glad you two are engaged," Shawn said insincerely.

"Thank you, but that's not why I'm calling. I thought you were great. I wanted to see what would happen."

Shawn sighed and sat back up. "I guess life happened."

"Yeah, it sure did." Sarah's voice trailed off. "I just wanted to clear that up."

"I appreciate it. And I'm sorry too. I could've ignored the post."

"Nope. You're not sorry. This one's all on me." They were both silent for a moment. "I'm going back into the gym. Thanks for actually calling. It was nice to hear from you."

"You too, Sara. Goodbye."

Since then, they hadn't spoken on the phone again. There were no more chance encounters when he visited Nia and Scott. Twice.

However, Shawn did send her a funny video about a week after their call. She responded with a voice message, almost making him choke on his lunch.

Later on, she shared a picture of teenage Scott and Shawn hanging out next to one of their first cars.

Sara: Too damn cute! 😅

Shawn returned the compliment with a voice message, accusing her of becoming a Facebook stalker.

This routine continued until now, with one of them sending a video or picture and the other always taking a few moments to reply in person.

Despite the friendship that had developed, breaking their routine proved challenging, even for something as simple as a question.

Shawn lay back down on his hotel bed and took a deep breath. He clicked "send."

Shawn: I'm in town for an IT event tomorrow. So, I decided to drive in tonight, get a room, and head home after it's finished. I've never set foot in this city since I was a kid, and it's Valentine's Day... Any suggestions on where I could grab a meal that isn't yet booked up?

He put his phone down, reached for the remote, and began flipping through the channels. He eventually settled on a familiar action movie.

The sound of his phone buzzing woke Shawn from his unintended nap.

Sara: Order room service?

Shawn: Because I'm one of those strange people who doesn't mind dining alone in restaurants.

Sara: Oh, you truly are strange! Wait, let me see what I can find.

A short time later, Sarah sent a link to a restaurant called DaVinci's. Shawn opened the website and confirmed a 9 pm reservation in his name.

Shawn: You didn't need to go to that extent.

Sara: The same courtesy I'd extend to any of my other friends.

Shawn peeked at the time: 5:47 pm.

Shawn: Guess I'll have to find something to do until then. Thank you!

Before taking a shower and searching on Google, Shawn discovered that DaVinci's was in the same parking lot as a big shopping center. Believing he would find enough entertainment to occupy him for another 2 hours and 30 minutes, he headed out.

However, by 8:30 pm, Shawn was moving through the crowd of people waiting at DaVinci's to reach the hostess stand. He inquired if there was a spot at the bar while he waited for his table, which the host confirmed. Shawn sighed, grateful for the last available seat next to the kitchen entrance and a dining couple.

When the bartender approached, Shawn ordered a Blue Moon and declined a menu, stating that he would have a table shortly. Sipping his beer, Shawn observed the people around him and engaged with a different bartender in a conversation about a sports story they had seen on the TV.

When the host returned, he informed Shawn that his table was now ready. Shawn finished his beer and accompanied the host to the other side of the restaurant.

The host mentioned, "Your date is already seated."

"Date?" Shawn inquired, puzzled. Claiming he had meant to take someone else's reservation, he prepared to protest until the host gestured toward his empty table and the person who was waiting for him.

"Hi, I'm Sara," she greeted him with a smile.

Shawn took his seat, feeling uneasy. Sara had her dark hair pulled back into a ponytail and wore a black dress with straps that just showed the smallest glimpse of cleavage. She had applied minimal makeup, different from her natural look when they first met.

"What are you doing here?" Shawn stammered.

"Good to see you too," Sara replied sarcastically, picking up her menu. "Kenny and I are celebrating Valentine's this weekend because he's traveling for work. I've been itching to eat here since they opened a few months ago."

"You could have gone with Kenny this weekend..."

"All the reservations were taken," Sara responded. She set down her menu and looked him in the eyes, sending butterflies to Shawn's stomach.

"I guess I shouldn't be so weird," Shawn conceded.

Sara smiled and continued looking at him, captivating him with her gaze. Shawn glanced at her menu when she asked him to place his order. After making his selection, he returned his attention to her.

As they discussed their chosen dishes, Sara's phone rang. "Hey, babe. How are you?" She mouthed the words "It's Kenny" to Shawn before beginning her conversation.

Shawn's eyes widened at the prospect of a potential issue, but Sara waved him off. "I'm fine. I'm at DaVinci's with Shawn. He's in town for a work event. He offered to take me out so you wouldn't have to spend Valentine's alone." She winked at him.

Shawn's heart skipped a beat. If she's willing to flirt like this, I don't need to worry about anything else.

But is it real? After requesting a New York strip, Shawn decided to change the subject. "So, you told me how you and Kenny became engaged. How did you two start dating?" Sara playfully tore apart a roll from the bread basket provided by the waitress while Shawn listened.

"He came into my work once weekly for package delivery. He would attempt to talk to me. I thought he was attractive but didn't pay much attention to him. Then one day, he insisted on buying me coffee, and I said okay. And we dated for a year, as I mentioned."

"You didn't want him making decisions like that for you," Shawn added. The waitress returned and poured their wine.

"I'm getting the filet mignon. I don't see why I should refuse something my friends have praised so highly." Sara grinned at him again and ordered a glass of Merlot, suggesting one for Shawn.

Engrossed in their conversation, the couple hardly noticed their entrees. Was that just teasing? Shawn thought after selecting a filet mignon and deciding to shift the topic. "So, you told me how you and Kenny came to be engaged. How did you two start dating?" Sara sliced a piece of bread.

"He comes to my work every week to deliver packages. He would always try to talk to me. I thought he was cute but didn't pay much attention to him. Then one day, he asked me for coffee, and I decided why not. We dated for a year as I told you before."

"You didn't want him making decisions like that for you."

"Sure, he relocated." Sara's cheeks turned a rosy shade. "And now I'm at dinner with you." Shawn winked at her jibe. "However, currently, I only see him on weekends, and the wedding is on hold while we determine where we'll establish ourselves." She picked up her glass of Merlot and raised it.

"A toast?" Shawn inquired as he picked up his glass to join hers.

"Certainly." Sara smiled broadly and looked into his eyes again. I can't determine if they're brown or copper... "To not being alone on Valentine's Day!"

They clinked glasses and sipped in unison.

Sara had intended to pass by his place when he texted, yet she didn't have any plans to see him until noticing DaVinci's had a reservation. Her job as an accountant had been overwhelmed with stress, and an unexpected visit from corporate on top of that. It made meeting him a suitable solution.

In the restaurant, they poked fun at one another while attempting to photograph their food.

"I don't even post them," Shawn guffawed. "I just admire good plating!" Sara came close to tears when the waitress appeared for the last time before they began consuming their meals.

"I reckon we'll require two additional glasses of wine, especially if all we're going to do is snap photographs!" Unaware of the joke, the waitress nodded but slightly rolled her eyes as she departed.

They both relaxed, and Sara began complimenting his meal. However, after a few morsels, Sara held up her wine glass and looked at him again.

"What?" Shawn questioned as he covered his mouth to hide his chewing.

"You know everything about Kenny now. I want to hear details of some of these 'undertakings' you've been working on back home." Shawn grimaced when the story about Scott the previous year reached Sara's ears.

"There's not much to say, in truth." He set his utensils on his plate, drank deeply from his water glass.

"I'm on the dating apps, though I haven't logged in recently. I had a few dates in October and November, but one was merely a casual hookup that continued until she met someone else."

Sara swallowed her wine to conceal her exasperation upon his sincerity. And jealousy.

"Three dates didn't go anywhere. I had been seeing a former colleague from the previous year."

"Did you have elaborate Valentine's Day plans?" Sara asked while cutting another piece of steak.

"Yes, I'd indeed organized some elaborate plans. I had sent her flowers to her workplace, went an hour outside the city for dinner, and then we saw a fantastic band right after and danced. Well, she danced, and I attempted to follow." Shawn chuckled. "Then we shared a night in the hotel and returned home in the morning."

"Sounds enjoyable." It was her turn to laugh.

"What?"

"The hotel part." She made air quotes with her unoccupied fingers. He smiled and rolled his eyes slightly.

"By late March, I visited her residence, and she stated she wasn't happy with how our relationship was progressing and terminated it. I've only encountered her once since in a supermarket last summer."

"That's unfortunate," Sara frowned subtly and she patted the top of his hand. Shawn laughed at her touch. "Then I met this girl in April..." Sara abruptly withdrew her hand and raised a finger in the air.

"Time to go!" She smilingly apologized.

Sara and Shawn exited DaVinci's, both being among the final patrons departing as the restaurant closed for the evening. After a small quarrel over who would settle the check, they split the bill.

Sara retrieved her keys from her purse and turned around to say farewell to Shawn, but he was still several feet away in front of the restaurant.

"Has the river view ever seen you here?" Sara inquired regarding the sign, moving back to his side.

"Absolutely. Once or twice."

"It states it's open until midnight for Valentine's. Would you mind taking a trip with a novice?"

Despite the cold, Sara experienced a thrill down her spine.

"Well, I can't let you go it independently. But you're paying this time!"

"You're the first couple to arrive since the night has fallen. It's too chilly for most of them. But I can help you out if you'd like." The lift operator assured them.

Shawn looked at Sara and they agreed with a nod. The operator flicked a couple of switches and the lift started running again. As the next car approached, he pressed a button, changing its color from green to red.

"Alright, folks. It'll take around 20 minutes to complete one round trip." He invited them in by opening the door. "The ride might be cold, no matter what. Here you go, have this blanket." He smiled while the lift continued to move.

Shawn and Sara remained quiet for a few moments, admiring the city lights as they glided through the air. They shared a blanket that separated them by a small distance, much like how they were sitting in the basement at Nia and Scott's.

Sara was already shivering in her warm coat, prompting Shawn to move closer and wrap his arm around her.

"Perhaps this wasn't the best of ideas," Sara mentioned.

"It's fine, and I'm happy to help," Shawn reassured her. She turned to him and didn't seem cold anymore. Only the darkness, the city lights, the humming of the lift, and Shawn's arm surrounded her.

Shawn's arm.

As they came closer, their lips met and he gently placed his hand on her waist. Twelve months of tension gave way to passion. Sara stroked his arm and he responded by lending his other arm around her, pulling her even closer.

Their online messages didn't prepare them for the intuitiveness of their kisses and touches.

Shawn pulled back for a moment to tease her, but Sara surprised him by biting his lower lip. Needing no further invitation, their lips rejoined, and Shawn traced his hand down her back.

"I didn't know how much I enjoyed your lips until now," Shawn admitted as he interrupted their passionate embraces. He proceeded to kiss her cheeks and her neck, utilizing his tongue and teeth.

Sara's nails dug into his shirt as she moaned into his mouth.

Wanting to reciprocate, Shawn slid his other hand down from her waist, falsifying a move away from her but instead discovered her bare skin.

"Wow," he murmured at the discovery. She wasn't wearing any underwear.

Shawn hesitated, unsure if she wanted him to go further, but Sara's hand locked with his and guided him higher up her leg.

"Go on," she urged, his fingers inside her, spreading her, "please make me come, Shawn."

Shawn paused momentarily, making eye contact with Sara before pushing two fingers deeper inside of her. Sara squealed and summoned his fingers when they retreated.

"I've always wanted to taste your sweet pussy," Shawn voiced his desires.

"Don't you dare!" Sara cautioned. "I'm at the end of my rope for you to change things up now. Push..." Her hand pressed into his wrist, pressing his fingers deeper, "there! Oh god, I am coming!"

Sara gasped as her body convulsed with her climax. Her head stumbled against the glass, making a soft thud.

"Are you all right?" Shawn asked, concerned.

Sara nodded and gripped his hand, pushing it more firmly on her clit.

"Keep going." Her voice faded as she became preoccupied. "I'm right on the edge again ...oh, I'm coming, oh god."

Sara could no longer form coherent sentences, only focused on the pleasure of his hand against her clitoris amidst the moving lift.

Shawn's hard-on grew uncomfortably against his jeans but he focused on Sara's pleasure more than his own. When her body subsided, her eyes opened and locked with his.

Shawn tasted her with his fingers, savoring her flavor. She giggled and asked him to taste her, one finger at a time.

The blanket had fallen to the floor, sending Shawn sitting on his knees, fingers still digging into her. Sara's eyes locked with his, admiring her lips as she pulled his fingers to her mouth. He sucked her off, absorbing her unusual flavor. The lack of underwear surprised him, but in that moment, it was enough.

Shawn traced her neck with his lips and tongue, tormenting her until she felt the warmth of his fingers between her thighs.

"Oh my God," she moaned, "I'm coming! Oh fuck, I'm coming!"

Sara lost all ability to form words as she experienced her second orgasm. She bit down on her lip but he persisted.

"Keep going, give it to me," she urged, panting and moaning, "I'm close."

Shawn was now faced with an incredibly difficult decision. Remembering that they had risked being caught resulting in severe consequences, he chose to still his fingers.

The lift jostled them as it reached the end of the loop, and hesitatingly, he pulled away, leaving her feeling unsatisfied.

"Sorry," he muttered guiltily but pleased with his decision, "I'm sorry."

The two of them looked at each other but could only feel a thought communicated: next time. She was left aching and yearning for more. She leaned closer and whispered, "I'll remember this" before returning to her previous position, clutching his arm as the lift finally came to a stop.

Damn, I can't believe that made me even wetter.

When Shawn landed awkwardly on the floor, they both burst into laughter. After a while, Shawn managed to get himself back in his seat, and Sara smoothed the blanket over their laps. Holding hands, they shared a sweet kiss on the cheek.

The elevator operator and the approaching end of their ride seemed well-timed.

"Did you enjoy the ride?" he asked, half-bored.

"It was beautiful out there," Sara answered, taking his hand as she stepped onto the solid ground.

"Yes, I'm really glad we did it," Shawn said, not moving his gaze from Sara. "Crap, I should've considered that before we got on. How much do I owe you?"

"Like I said, you're the first people I've seen tonight. This one's on me," he smiled, checking his watch. "I hope you two have a lovely evening."

Shawn thanked the man but still handed him ten dollars for being so kind. Turning back to Sara, they smiled silently at each other.

Once they reached their vehicles, they dropped each other's hands and looked each other in the eye. They couldn't say a word, feeling the guilt of their actions, and yet, their bodies betrayed them.

"Thanks for setting up the dinner reservation," Shawn said, eventually braking their silence. "That was one hell of a meal I won't forget." Sara nodded, struggling to maintain eye contact, and fished for her keys in her bag.

"I'm glad I got to try it," she replied, then looked away. Shawn wanted her to join him at his hotel. He didn't plan to continue what they'd started, he just wanted her there longer. But he knew saying that might scare her.

"I'll let you know when I make it back to my hotel," he ventured, trying his smallest smile. He opened the car door and waved goodbye.

"Okay, have a good night," Sara replied, opening her own door and waving back. A minute or so later, they both drove off in opposite directions.

After a few minutes, Shawn returned to his room, shut the door, and leaned against it. He massaged his face, still smelling Sara's scent on his fingers.

"Fuck," he sighed, feeling defeated. He walked over to the bed and flopped on his stomach and chest. He picked up his phone, remembering he promised to text her.

"Made it."

Shawn stared at the screen, waiting, but there was no response. Of course not, you idiot. You took advantage of her loneliness on Valentine's Day while she's fiance is out of town. Why should she say anything? Setting it down, he lay back against the bed, feeling more at peace with his defeat.

That night, his phone rang, waking him from his drunken stupor. He rolled over and took the phone.

"Sara? Are you okay?"

"Yes, I got home. Everything's fine. I'm just trying to figure out how to say this. Shawn, what happened tonight... it can't happen anymore. I'm getting married to Kenny." She paused and swallowed hard.

"It wasn't just you. I didn't have to invite you on the ride. I didn't have to kiss you... or anything else we did. I was wrong for taking advantage of you."

Sara laughed.

"Really? I didn't feel like I was being taken advantage of. I kind of initiated it all, remember?"

"Yes..."

"Fuck, you were so good." Shawn grinned.

"I know, it's so much fun watching you respond to my touch." Sara bit her lip, her body in conflict with her brain.

"I'm serious, Sara. This can't keep happening."

"I know... I have to tell Kenny. I was completely wrong in how I acted."

"Right," Shawn agreed, his heart sinking.

"I'll go now. Sleep off that wine."

"You too. Have a good night."

Rubbing her temples, Sara went in search of some peace. Why does he make me feel so crazy? And why doesn't Kenny make me feel like this? After pondering fruitlessly, she crawled into her bed, still a mess from that morning.

She shut her eyes for around 45 seconds before she reopened them to glance at the roof.

She exhaled and bent over toward her nightstand drawer, extracting a slender pink sex toy. Once she shut the drawer again, she resumed her supine position, maneuvering slightly to slip out of her underwear.

There's nothing wrong with recalling how he was caressing me earlier though. Her toy sprang to life with a frantic buzz, and she carefully guided it into her wet pussy.

"Gaaaaaah, if only you were here, Shawn..."

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