Humpday Story: Five Years Without Dessert

Late evening. Quiet restaurant. The best cherry pie in town. 

Caleb places his hand on top of Michelle’s. If only he planned this perfect date. Perfection meaning, only coffee and dessert. Maybe more later…

Sometimes, perfection happens when not planned.

***

the best friday night

On a whim Caleb Nelson placed his hand on top of Michelle’s. He wanted to do that all night, and thought about it all day before their date. 

The waitress just brought cherry pie a la mode for both of them. Rock music played from the other side of the wall in the kitchen, almost loud enough to drown out the cooks’ bantering, the heavy rhythm an annoying counter-point to the softer pop music playing from the dining room’s speakers. 

Hardly anybody was at Betty’s Stackhouse at ten o’clock in the evening. It was like the world had gone quiet and stayed home. Either that or Betty’s was going out of business. Judging by the potholes in the parking lot and the funky smells in the bathroom, that wouldn’t have surprised him. 

Just Caleb and Michelle, and an older couple who ordered heavenly smelling blueberry pancakes. Caleb almost wished he’d split an order of that with Michelle, instead of the pie. 

She wrapped her fingers around his and clasped her other hand over his. She had the most amazing green eyes that lit up when she smiled at him. Her long black hair was tied up in a loose bun, the green and purple dyed strands hung down in front of her ears. She wore a pink cardigan over a white and black stripped dress. 

Under the table, every so often, she bumped her ankle boot against his calf, especially when making a point. 

“Your pie smells delicious,” she said, bumping into his calf. 

“So does yours,” Caleb squeezed her fingers gently. 

He almost hadn’t chosen Betty’s. Almost hadn’t gone out with Michelle for the second time this week. Their first date had been impromptu after work on Monday. Just coffee between coworkers, nothing more. And that’s what Caleb figured it would remain, despite how wonderful that made the beginning of the week feel. 

Until Michelle texted him early in the morning, while he was still eating his bagel and on the first cup of coffee for the day, and asked him what he was doing. He called her, and asked her to meet him for pie either later tonight or on Friday. 

Michelle immediately responded, “Tonight.” 

Betty’s was a choice of habit. Despite the mediocre service and the smelly bathrooms, they had the best pies in town. 

He relaxed his fingers out of her hands, and she let go. As she dug into her pie, he poured fresh coffee for both of them. 

“I’d ask how your day was,” he said. 

Michelle giggled. “Rule number three.” 

“Right,” he said. Three simple rules they’d made up and agreed to before their first date. Rule three was to never ask about work outside of work. Since it was still Friday, and they both worked at an IT call center, Caleb already figured how her day went. 

She wiggled her spoon at him. “You did forget to ask me something.” 

Caleb poured creamer into her coffee and stirred it. Funny how he knew her preferences, like they were already a couple—one creamer, no sugar. He took the exact opposite, preferring sweetness over taste. 

“What’s that?” he said, trying to hide his smile and failing. He honestly figured he lost his chance after their Monday night date. Having a second chance so soon was a pleasant surprise. 

“You forgot?” she said. Michelle glanced at him askance, then shook her head, the green and purple strands jiggling about. “Well then, you’ll have to figure it out for yourself.” 

“Well crap,” he said. 

And then she laughed at him. He could’ve watched her laugh all night if it were possible. The way one eye slitted almost shut, the other widened. The quirky way her lips curled. And the cute pink blush on her ears and throat. 

They chatted about nothing and everything while they ate pie and drank coffee. Books, movies, concerts they’d love to see. He stacked her empty plate on top of his and shoved them aside. Then he poured more coffee for her. 

“Slow down there, buddy,” Michelle said. “You want me up all night?” 

“Maybe I do,” Caleb said, winking. He added another creamer to hers, a sugar to his, and stirred both. 

“Good thing I don’t work tomorrow,” she said. “And if I did, I might not care.” 

“Is that so?” 

“Depends on what your intentions are,” she said with that funny quirk in her lips. 

“I… I don’t know,” he said. He stared down at his mug, not sure how to say what he needed to say to her. After an appropriately awkward silence, he blurted it out. “It’s been a long time since I’ve done this.” 

“This?” she said. Then she took his hand in hers. “Sex? Or dating? Just asking.” 

“Both,” he said. “The last time was a date like this. Too much coffee, a sugary dessert, and we ended the night rolling around in bed.” 

“May I ask how long ago?” she said. “Not my business if you don’t want to tell me.” 

“Five years,” he said. 

Caleb expected her to take her hand away from his. Maybe recoil in shock. Or pity. She did none of those things. 

Instead, she massaged his thumb with hers. “Sorry to hear that,” she said, and sounded like she meant it. 

“Nothing to be sorry for,” he said. “I told you about my bookstore? I got busy building a business and had so little time for anything serious. Nothing unserious came along either.” 

“Nothing wrong with a focused man,” she said. 

“And then the recession happened and I lost everything,” he said. 

“Nothing wrong with that either,” she said. “I lost a six-figure corporate job and moved back in with my parents for three years. Talk about not having dessert.” 

“Not having dessert?” Caleb said. 

Michelle chuckled. When she talked to him, often she got ahead of herself in conversations. Caleb suspected this was one of those times. 

Rule number two—always ask for clarification before assuming. A good rule. One Caleb wished he’d had with previous girlfriends. 

“Your last girlfriend,” she said. “You had dessert and then sex. You haven’t done that in five years.” 

“Gotcha.” Caleb nodded his head. And then laughed. Five years without dessert seemed like a damn long time when Michelle put it like that. 

She cocked her head to one side, letting the multi-colored locks of hair fall across her shoulder. “Just saying, you should allow yourself some dessert now and then.” 

“I just had cherry pie. Not sure what you mean by that.” Caleb patted her forearm. She brushed him aside. 

“I think you know what I mean,” she said. “If you knew what to ask me about.” 

He smiled. Caleb hadn’t forgotten of course. Just put it off, unsure if he was ready. If not now, then when? Ever? Fuck it… 

“Do you want to come back to my place for a night cap?” he asked. 

“I do,” she said, bumping him in the leg with her boot. 

He allowed the moment to sink in. At last, after all this time working so hard with no play, Caleb finally had a shot. He wasn’t going to force things to happen, but a chance was a chance. But he still needed one thing. 

“You sure about this?” he said. “Could get complicated at work. Not like I’m trying to blow my own chances or anything.” 

Michelle nodded slowly, smiling. “And if it gets complicated? I don’t know, I’m due for another job soon. We’ll figure it out. Besides, you violated rule number one.” 

“Oops,” he said. “I won’t make that mistake again.” 

Rule number one… see rule number three. 

They laughed together, holding hands. He leaned forward and kissed her on the mouth. Michelle leaned toward him to get closer. She licked his teeth and played with his tongue. Caleb became uncomfortably hard. He wanted to adjust himself, or better yet let himself out. 

Once the kiss ended, he stared into her eyes for a long time. Michelle cupped his face with both hands. He held her by the elbows. Only the table was in the way. The moment could’ve gone on forever. 

“I’ll text you my address,” he said. 

“Sounds good,” she said. “Just bring a condom.” 

“Thought of that earlier today.” 

“Oh?” she said. “Somebody likes to be prepared.”

“I live fifteen minutes from here,” he said. 

“Good. I can’t wait much longer.” 

He scooped up the bill, tossed a five on the table for the waitress, and went to pay. 

His boner hadn’t gone down. The waitress certainly noticed, though he tried to cover it with his jacket. But he felt too good to care what she thought. 

Tonight was the best Friday night he’d had in a long time.

***

Caleb barely shut the front door behind him when Michelle grabbed the back of his hair and kissed him again. He pressed her up against the wall, hands on her waist, tongue in her mouth. She felt small in his arms, like she was made to fit inside him. Much smaller than he imagined. Working with her, seeing her as an equal made her seem larger than life. Now she was flesh and blood and in his home. 

She still smelled of coffee and pie. Her perfume was faded now, just a hint of chamomile and lilacs. 

He made out with her in the front hall. It’d been so long since he’d done this with a woman in this spot, it felt unreal and amazing at the same time. Like a dream, but lucid. He kept expecting to snap out of it any time, and come back to reality. 

And then he picked her up in his arms. She giggled and wrapped her arms around his neck, holding on loosely. That was reality enough for him. 

He carried her upstairs to his bedroom. Luckily he left the bedside lamp on and pulled down the covers just for this occasion. Funny how he hadn’t expected this, but prepared for it anyway. 

And then he tossed her onto his bed. Michelle bounced a couple times. 

“I’ll get the nightcaps,” he said. “What’s your poison?” 

Michelle pressed a finger under her lip. “My poison? You, of course.” 

Caleb liked the sound of that. He took his shirt off and climbed onto the bed with her. Her fingers were all over his skin, up his ribs, lazily across his nipples, down his stomach. He worked out, but hadn’t been particularly proud of his progress. By the whimsical expression on Michelle’s face and her hungry fingers, she had no complaints about his physique. 

He nudged her down flat on the bed. Michelle pulled the pins out of her bun, letting her hair fall apart around her. He toyed with her hair, his fingers combing through her mane. 

“I think I love you,” he said. 

“Stop thinking already and do something about it,” she said. 

He kissed her on the neck. Thrashing about, she managed to take off her cardigan, breaking a few seams along the way, and tossed it aside on the floor. His kisses went down her neck, her shoulder, down her bare arm. He kissed all the way to her wrist. And then back up her other wrist, repeating the motion in reverse. 

One knee between his legs, she tickled his ribs, making him stop and gasp. 

“Ticklish?” she said as if sorry, but not. 

“Damn it,” he said, “you figured it out.” 

Michelle giggled. “Damn it all.” 

She focused her fingers on other parts. Across his back, His shoulder blades. Just above his belt. Her fingers roamed everywhere, as if she wanted to touch everything all at once. 

And then she pushed at him to let her up. She turned around, presenting the zipper on the back of her dress. He slowly unzipped her and let the dress fall down around her waist. He helped her out of it and tossed it aside on the bed. She wore a black bra and matching panties and her boots. Nothing else, besides her earrings and necklace. 

Caleb admired her for a moment. For as long as he’d worked with her, he so often fantasized about having her in his bed like this. Now that fantasy became reality, he wondered again if he’d wake up. 

And if he did, he wanted to make the most of this crazy ass dream. 

He kissed down her shoulder and back, casually tugging down one bra strap as he followed the curve of her body. And then down further, across her bubble butt. With one finger, he pulled down her panties, revealing a neatly trimmed patch of hair between her legs. Her labia were shaved smooth. 

Michelle leaned on her elbows, pointing her butt in the air to give him better access. Caleb traced his tongue across her lips. Gentle, slow. The smell of her pussy drove him insane. He’d forgotten what it felt like to do this. It was all he could do to keep himself in control, make it as pleasurable for her as possible. He wanted to be inside so badly. His heart hammered in his chest. He could barely keep his fingers from shaking in anticipation. 

“Play with my clit too,” she said, reaching between her legs to rub her clit as if to show him what she wanted. “Pretty please?” 

Caleb couldn’t say no to that. 

He flicked his tongue across her clit, back and forth, up and down, varying the pace and the rhythm. He opened her labia up, pressed his tongue inside for a bit, before returning back to her clit. He wandered across all her parts. 

And then while rubbing her clit with one finger, he used his other fingers inside her, curling them against her G-spot. Took a few minutes, but he figured out where she was sensitive. He still knew how to do the rip-and-grip technique, as his last girlfriend called it. 

Thankfully, Michelle seemed to enjoy it more. She moaned in pleasure, begging him to not stop. 

But he did. 

Michelle protested. Caleb ignored her, and reached for the top nightstand drawer. The box of condoms were there, and he got one. She watched him the whole time, a big smile on her face, ass wiggling about. 

Once he had the condom slipped on, he took her by the hips from behind. Then he teased her with the tip of his cock. And inch, then pulled out. A little further inside, making her squeal, then out again. Finally he entered her balls deep. 

Caleb wiggled his hips about, repeatedly hitting and stroking her G-spot with the tip of his cock. Her juices dripped as if somebody poured warm water down his balls. He slowed to a stop, then continued. She mumbled incoherently, rubbing her clit with her finger as he fucked her. She rocked her hips against him to try to make him go faster. 

He went faster. Then slowed down again. He kept varying the pace, making her squirm and beg. 

And then he flipped her over onto her back. Caleb lifted Michelle’s legs over his shoulders and entered her again. He closed her legs so she was tight on his cock. 

Michelle gripped the bedsheets in her fists. Her chest heaved, pushing her breasts up in her bra. Her hair clung in sweaty strands on her face. 

And then Caleb took her faster and harder. He shook the bed. His skin heated and he had a hard time breathing. His heart hammered in his chest. 

She screamed out loud enough to wake up neighbors. Caleb didn’t even care. So what if they heard? He didn’t care what they thought. This was what he’d dreamed about for so long. And now he was having the best dessert and the best date he’d had in a very long time. The neighbors’ opinions were a small price to pay for a beautiful night of action. 

He felt the come building up in his balls. The orgasm was so close. But he denied himself the pleasure. He stopped, and then kissed and made out with her. Michelle grabbed his ass in both hand, slapping him hard as if to make start again. 

He made her suffer with need. Just as much as he suffered for all those years without dessert. He wanted her body to ache just like his did. Ache with the desire to explode in pleasure with someone else. 

And then he was dangerously close. Caleb pulled out and rolled onto his back, telling her he needed a break. But Michelle would have none of that. 

She climbed on top of his reverse cowgirl style. She took him in gently, carefully. Once she was settled on top, she flipped her hair and looked over her shoulder at him. She smiled. 

And then Michelle grabbed him by the thighs and bounced on top of him. Her bra came off. And then she took off her boots. The whole time she kept him inside her. Closer to the edge, desperate to have all of her, Caleb massaged her butt and begged her to make him come inside of her. 

But before he did, her pussy spat him back out. Michelle ripped the condom off, almost tearing if apart. She took his cock into her mouth, tasting all of him from tip to balls and back up again. 

He’d never blown a load with a blowjob, and wanted to tell her so. But he kept his mouth shut. He figured she’d give him some pleasant oral and then he could continue having her pussy wrapped around his cock again. 

Except he felt the orgasm long before it hit fully. Her teeth applied pressure up and down his shaft. She massaged and tugged on his balls. 

He came all over her face. Strings of come blew into her hair. 

Exhausted and spent, Caleb stretched out on his back. Michelle settled on top of him, kissing his neck. 

“How was dessert?” she said. 

“Thank you,” he said. “Perfect.” 

He couldn’t say much more. 

Five years was too long to wait. It felt like the first time all over again, but much sweeter. Michelle had been the perfect woman to share it with.

***

Copyright © 2020 Hermit Muse Publishing

Cover image © meggj/BigStockPhoto.com

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