Trials And Tribulations Of Online Dating © 2018 Louisa Masters
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Trials And Tribulations Of Online Dating is a work of fiction. All names, characters, events and places found therein are either from the author’s imagination or used fictitiously. Any similarity to persons alive or dead, actual events, locations, or organizations is entirely coincidental and not intended by the author.
Table of Contents
Chapter One
Chapter Two
Chapter Three
Chapter Four
Chapter Five
Chapter Six
Chapter Seven
Chapter Eight
Chapter Nine
Chapter Ten
Chapter One
Samantha flopped onto her best friend’s sofa and tucked her messy brown hair behind her ear. “We’re in a rut.”
Leona took a more sedate seat in an armchair, looking neat and pretty as she always did. “Part of that rut could be sitting here telling each other we’re in a rut,” she suggested. “Instead of, you know, actually doing something different.”
Sam sat up. “Like what? What could get us out of this pattern? We see the same people, go to the same places, do the same things week after week. What is going to move us to the next phase of our lives?” She reached out and snagged her wineglass from the coffee table and glared at it. “We even drink the same wine all the time!”
“That’s because we like it.” Leona smiled. “There’s nothing wrong with that.”
“But how do we know there isn’t another wine out there that we might like better? We should try other wines, see what they’re like. Maybe expand our wine repertoire.”
“Repertoire? Really?”
Sam shrugged. “You know what I mean. All I’m saying is, we never try new things. Take men, for example. Neither of us has had a date in months, because we never meet new guys. We need to get out there, or we’ll end up old maids, living in the same retirement village, knitting, with a thousand cats.”
“Dramatic, much? Come on, Sam. It’s not like we deliberately hide away. We go out all the time. It’s just hard to meet new guys.”
“So we should make more effort! Maybe I should ask someone at work to fix me up with someone. A blind date. Or....” She eyed Leona speculatively. She was pretty sure her friend was going to hate this idea. “We could sign up for online dating.”
Leona sipped from her glass. “Who is this ‘we’ that you speak of? Because it sure as hell doesn’t include me.”
“Come on,” Sam coaxed. “It’ll be good for us. Even if we don’t find Mr. Right, we’ll still meet new people. New friends can’t hurt, right? We’re social people. Friends are always welcome.”
“Sure, but online dating? I don’t think so, Sammy. Have you heard how many predators sign up for those sites?”
Sam rolled her eyes. “I’m not saying you should pick a guy at random and go over to his place without telling anyone what you’re doing. We’ll be careful. Screen matches. Communicate through email, graduate to phone, and then a date in a public place. Lee, thousands of people do this all the time. It’s like everything else—as safe as you make it.”
“I just don’t get why I have to do it. I’m not stopping you.”
Samantha hesitated, bit her lip. “I don’t want to do it alone, that’s all. Besides, it’ll be fun to do it together. Compare matches and stuff. Maybe have some double dates.”
Leona shook her head. “I just don’t like the idea of deciding to date someone based on an online profile. At least with something like speed dating you get the chance to evaluate the person face-to-face.”
Sam sat up straight. “Okay. I’ll sign up for online dating, and you go to one of those speed dating parties.”
“What? No, that’s not what I meant.” Leona put her glass down with a clink.
“Why not? It’s a great idea! We’ll both get out of this stupid rut we’re in, meet some new people. You can do your face-to-face assessment and help me narrow down some online matches.” She leaned forward. “Plus, aren’t you sick of spending your free time with me? I mean, you know I love you, babe, but you can’t give me all the things a man can.”
“Isn’t that what Levi’s for?” Leona’s voice had turned very dry. Sam knew her best friend didn’t fully approve of the friends-with-benefits arrangement Sam had with her next-door neighbor.
She waved a dismissive hand. “Levi and I aren’t like that. I don’t want someone who can be my best friend and give me regular orgasms; I want that romantic thrill. You know I’ve been waiting since I was a little girl for a man who makes my heart beat faster. If this were an ideal world, that would be Levi. Unfortunately, life doesn’t work that way, so until I find the man who gives me arrhythmia, I’ll take hot sex with one of my best buds.” She winked, and Leona cracked a reluctant smile.
“I don’t know how you can separate sex from emotion, that’s all.”
“I’m not,” Sam explained, for what felt like the millionth time. “I have emotions for Levi. Friendship. Fondness. A huge appreciation for his dick, and genuine admiration of his ability to use it. Love, even; I’m just not in love with him, and he’s not in love with me. Why should we have to be alone while we wait for our perfect matches? And if I find Mr. Perfect Match while I’m online dating, then Levi and I go back to just being friends. He’ll be happy for me.”
Leona sighed. “You’re really set on this, aren’t you? This is going to be one of those things you’ve decided on that you’re not going to let go.”
“Pretty much,” Sam agreed. “I really think this is a good idea. I think at the very least it’ll shake us up and give us some new direction. It may lead to happy relationships.”
“Fine, then. You do online dating and I’ll do speed dating.”
“Yay!” Sam leaped up and hugged her friend. “I promise, you won’t regret this.”
“I’m not so sure,” Leona said darkly. Both women looked up as Sam’s phone chimed from the bench. She let Leona go and went to check it.
U home 2nite?
“Levi,” she answered Leona’s unasked question, and ignored the look of mixed worry and resignation on her best friend’s face. Lee had often expressed her concern that sex was going to ruin Sam and Levi’s friendship.
Give me an hour. I’ll come 2 u.
“Are you dumping me to go play with your fuck buddy?”
“He’s not my fuck buddy.” Sam paused. “Exactly. And no, I’m going to finish this wine and then we’re going to hunt down some speed dating parties. Then I’ll dump you and go play with Levi.”
Leona took a huge swallow of wine. “Lovely.”
# # #
Sam knocked on Levi’s door and then leaned against the frame. It had been three days since she’d last seen him in person, and she’d missed him—on several levels. Levi was one of her dearest friends, with whom she’d had an easy bond from the moment they’d met, but she also hadn’t been kidding when she’d told Leona that she admired his sexual abilities. The man
was seriously talented.
The door opened, and she smiled. “Hey.”
Levi’s return smile was warm, lighting his green eyes.
“Hey yourself. Come in.”
Sam crossed the threshold, waited for him to close the door, and then jumped him, the collision of her body into his forcible. Grasping his shoulders for leverage as he stumbled back into the wall, she wrapped her legs around him and planted her lips on his.
It took only seconds for him to respond, turning them so she was the one pressed against the wall. He tore his lips from hers and planted hot, open-mouthed kisses along her jawline until finally he took her earlobe between his teeth and nipped gently. Sam’s stomach cramped and lightning shot through her. Levi undulated against her, his hard cock pressing against her pussy, then drawing away before returning to torment her with fleeting pressure. Sam let go of his shoulders and grabbed his hips, nearly overbalancing them in her attempt to grind against him.
Levi tore his mouth from her flesh and staggered back, taking her with him and lowering them both to the floor. Sam barely had time to put her hands back on his hot, sexy skin, before he was working at her top.
Good idea. She grabbed the hem of his T-shirt and yanked it up, getting in his way and tangling their hands in the fabric.
“Sammy, wait.”
She maintained her grip. “Take it off.”
He grinned and released her shirt to take hold of his own. “Let go.” He barely gave her time to do so before he tugged it off over his head.
Hmm. His chest was amazing, firm and muscled, and she ran her hands familiarly over the hot flesh. Her gaze zeroed in on his nipples, and she leaned forward and clamped her teeth on one.
“Ung.” The shudder that coursed through Levi encouraged her to lave her tongue across the nub. He shuddered again, then stroked a finger down the side of her face.
“Let go. I want you naked.” He was still working on the buttons of her shirt. Reluctantly, she released his nipple and straightened, unbuttoning his jeans as he stripped off her top then unclipped her bra.
Within moments, they were both naked, and Levi rolled her under him. The tile floor was cold and hard against her back, but her front, pressed against Levi, was burning hot, and the contrast was incredibly arousing.
Levi shifted, rubbing his dick against her clit, and shivers of pleasure vibrated through her. “Can’t wait,” she muttered, undulating, loving the drag of his throbbing cock on her.
Levi moved away.
“No!” she protested, and he laughed. She heard the rustle of fabric, then he was back, condom in hand. “Let me do it,” she begged, and he handed it to her without argument, his eyes gleaming.
She sat up, ripped open the packet, and took his dick in her hand. It was hot, the skin impossibly soft and smooth, and she stroked, once, twice and squeezed gently. It jumped in her grip.
“Samantha!”
Sam cast him a wicked smile and rolled the condom on. She’d barely finished when he pushed her back to the floor and entered her in one swift, incredibly arousing thrust. She moaned, a drawn out sound, as Levi started a steady, rhythmic thrusting that managed to hit all her sensitive spots, but she needed more, needed it faster, harder….
She surged upward, paused to appreciate the hot fullness as Levi’s cock hit impossible depths within her, then shoved him, rolling them over and seating herself on him.
He gazed up at her, his green eyes slumberous and his dark hair tousled. There was a half smile on his mouth and the hint of color on his impossibly high cheekbones. He shifted slightly, and his dick rubbed the swollen tissues in her cunt. She closed her eyes to savor the sensation and began to move, slowly at first, determined to tease him the way he’d teased her, her urgency appeased somewhat now that she’d seized control.
The sudden grip of hands on her hips, of calloused palms sliding up her torso, had her opening her eyes again. Levi’s attention was fixed on her chest. Her breasts were bobbing slightly as she undulated over him, and as she watched, he rubbed them, paying special attention to her painfully erect nipples. Every touch on the swollen nubs was like a direct shock to her pussy, which clenched and unclenched in response. Within moments, they were both moaning, and she set up a faster rhythm, matched by Levi’s urgent tugs on her nipples.
Panting, Sam strove to control her movements, to measure the contractions of her cunt. Instead, she steadily spiraled out of control, her inner muscles clamping down hard on Levi’s dick and sending them both over the edge.
# # #
Sam lay on Levi’s warm body, waiting for her heartbeat to slow to normal. Finally, she cleared her throat and sat up, enjoying the sensation of his semihard cock still inside her.
“So, how’s your week been?”
He laughed, a deep, infectious sound. “Better now. You up for another round?”
“You betcha. I left Lee’s place early so I could come and play with you.”
Smiling, he sat up carefully, and Sam moaned. “You’re so much fun to play with,” she added breathlessly. He eased her off him and got to his feet, then reached down to help her up.
“Come on, I want some water, and then we can play some more.” He led her into the kitchen and got water from the fridge for them both, then leaned against the sink to drink his. Sam admired the strong line of his throat as he swallowed, and let her eyes wander. He was such a gorgeous man, even with his hair standing on end from her impatient hands. He lowered the bottle and caught her gaze.
“What?”
“Nothing. Hey, Lee and I have decided to break out of our rut.”
“Oh? How?” He put the bottle down and caught her hand, tugging her along as he headed for the bedroom.
“Well, I’m going to sign up for online dating, and she’s going to do speed dating. You know, meet new people.” She followed him over to the bed and shoved him down. Climbing on top, she leaned over and licked his dick from base to top, like an ice cream. He grunted.
“Sounds like fun.”
Chapter Two
Three weeks later....
Sam sat back in her chair and tried not to let her eyes glaze over. God, how could anyone be this boring? It was like he’d used up everything interesting about his life during their phone calls, and now all that was left was ridiculously dull.
“...don’t you think?”
She shook herself out of her stupor. “Absolutely.” She had no idea what she’d just agreed with, but it must have been the right response, because he smiled and started talking again. Something about salmon....
She’d had such high hopes for this date. Online dating was not going the way she’d thought it would. For starters, she hadn’t been entirely happy with the first round of matches the site had supplied. All the profiles had seemed too perfect, almost plastic. Leona had pointed out that people naturally wanted to make themselves sound good, but it had taken a while before she could read between the lines of each profile. Still, she’d had eleven prospects that she’d sent messages to. One had messaged back, thanking her but advising that he was now off the market. Two had not responded at all. Of the remaining eight, one had messaged her with an invitation to join a cult and one had requested photos of her in a swimsuit. Six had sounded reasonably normal, so she’d graduated from messages to emails to phone calls.
Unfortunately, two of her matches were so socially inhibited they could barely maintain a conversation. There had been a lot of long, awkward silences, and there was only so much inane chatter she could manage. That had left her with four prospects, and thus four dates that she’d set up for this week.
This one, the first, was not an indication that good things were to come.
And meanwhile, her date was looking at her expectantly, and she had no idea what conversational ball she was meant to be juggling.
“Uh—if you don’t mind, I might ca
ll it a night. I’m not feeling too good.” Lame. She was so disappointed in herself.
Mr. Boring nodded sympathetically. “Of course. You do seem a little off your game.”
Uh. What? Sam decided to let that comment slide, as she had no intention of ever speaking with the man again unless she suddenly developed insomnia. She motioned the waiter for the check, insisted on paying her half, and forced herself to be civil when Mr. Boring walked her to her car. As he fumbled through a goodbye, hinting at another date, she smiled gently, and then finally said, “I don’t think that’s a good idea. I just don’t feel that we’ve clicked.” The wounded-puppy look on his face made her feel horrible, but she shut down the guilt, said goodbye again, and got into her car.
Driving home, she wondered dismally if Leona had been right all along. Was this a bad idea?
Suck it up, Sam. One bad date was nothing. Her next three might be exceptional. She had to stay focused and be positive. Hey, at least she’d broken out of her rut for the night.
She turned into the driveway and noticed that Levi’s light was on. It was not even ten yet, still early enough to bug him, maybe have a decent conversation and a massage with a happy ending. She texted him while she unlocked her front door, and then kicked off her shoes with some relief. She was changing into sweats when her phone chimed.
Come over.
She smiled as she made her way across their front yards. The door opened as she approached and Levi stood there, in sweatpants and an old T-shirt that fit really well, and her smile grew. He was so pretty to look at.
“I just had the date from hell.” She stood on tiptoe and planted a quick kiss on his mouth. He laughed.
“What happened?” He closed the door and followed her down the hall to the kitchen. “Want a drink?” He gestured with the beer bottle in his hand.
“Love one. I only had half a glass of wine with dinner—I was afraid to have more, in case it put me to sleep.”
He paused in the act of opening her beer. “Alcohol doesn’t normally make you sleepy,” he said, his gaze concerned. She rolled her eyes and practically snatched the bottle from him.
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