Trials and Tribulations of Online Dating

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by Louisa Masters


  “Honey, I’m really excited for you—I know how disappointed you were that dates one and two sucked—but I have to ask something. You really like this guy—what’s his name, by the way?”

  “Jack.”

  “Okay, so you and Jack had an awesome first date, you’re going out again, but doesn’t it seem weird to you that your scheduling conflict is your fuck buddy’s father’s birthday?”

  Sam closed her eyes and sighed. “Stop calling Levi my fuck buddy. The term implies that our relationship is only about sex, and that’s not true. After you, Levi’s my best friend. Besides, I like his dad. He’s a great man. Levi and I spent the afternoon working on his birthday gift, to the point that I was nearly late for my date with Jack. I made a commitment to go to Tom’s birthday, and I’m not going to back out because of a date, no matter how much I like the guy.”

  “But you’re still having sex with Levi in the meantime?”

  “Yes. No. I don’t know. I don’t think Jack and I have quite reached the point of exclusivity yet,” she troweled on the sarcasm, “so until we get there, Levi and I are the same as we’ve always been.”

  “I’m bringing you down, aren’t I?” Leona asked.

  “A little. I get why you’re concerned, but you just don’t understand how it is with Levi and me.”

  “I do get how it is with Levi and you, and it breaks my heart. I think the two of you would be perfect together. I want you both to open your eyes and see that you’re not just friends that fuck. You’re made for each other.”

  Sam closed her eyes. “Lee, I’m not going to lie. Levi’s awesome. In so many ways, he’s my soul mate. But he doesn’t make my heart beat fas—”

  “Fuck your heartbeat!”

  The outburst sat between them, and the moment stretched. Finally, Leona sighed.

  “Listen. I know you’ve been waiting all your life for a man who makes your heart beat faster. I know you’ve felt little heart flutters with guys before, and then it didn’t work out, but that was okay, because it wasn’t really beating faster. But here’s the thing: the heart beats faster for a lot of reasons, Sam. It’s just a reaction in your body. Exercise causes it. Stress. Excitement of many kinds. And yes, attraction. Maybe you meet a guy who makes your heart beat faster. Maybe that guy is Jack. Will you have with him everything you have with Levi? Because Levi is your best friend and you have amazing sex. You just said it; he’s your soul mate. For a lot of people, that’s a dream come true.”

  Sam remained frozen, unable to process. Leona sighed again.

  “You should definitely give Jack a chance. But I think you should do the same for Levi.” Another short pause. “Okay. Call me tomorrow. You’ve got another date with a prospect, right?”

  Sam pulled herself together and shunted aside thoughts of dating Levi, her best friend. “Yep—last one, until I run another group of matches. Maybe I’ll get another Jack.”

  Leona chuckled quietly. “Maybe. Good night.”

  Sam said good night and disconnected the call. She stood and wandered toward her bedroom, flicking off lights as she went. Her phone chimed just as she was sliding under the covers, and she picked it up. It was from Levi.

  Let me no if ur home safe

  Leona was totally wrong. Levi was the best. He was awesome. But he wasn’t for her.

  Home & in bed – AMAZING date! Ttyl xox

  Chapter Five

  Tom Matthewson slid an arm around Sam’s waist and hugged her close. “How’s my Sammy?”

  Sam laughed. She loved Levi’s dad. “I’m good. Happy birthday! How has your day been?”

  Tom let her go and handed her a beer. “Excellent. I got breakfast in bed this morning and then sneaked off for a round of golf. What’ve you been up to?”

  Sam told him about her online dating mission, finishing with, “So I’ve met one really great guy and one potential friend, which is a pretty good outcome so far.”

  “You should be careful.” Tom had been frowning since he heard about date number two.

  “I am being careful,” she assured him. “Levi and Leona both know every time I go on a date, when I get home, who I’m going with—the whole thing.”

  Tom sighed. “I admit, I’ve always hoped that Levi would pull his thumb out and pin you down. I like the idea of having you for a daughter-in-law. Definitely more than I like Levi’s usual bimbos.”

  “That’s not fair,” Sam protested in Levi’s defense. “He’s dated a lot of really nice women.” She snorted. “It’s just that when he picks a bad one, she’s really bad.”

  An arm came around her shoulders. “What are you two chortling about?” Levi asked.

  “You,” his father said, “and your ridiculous taste in women.”

  “Oh, fine. Pick on me. Have you heard about Sam’s ridiculous taste in men?”

  “We were just talking about that,” Tom said, and pointed his beer at his son. “Are you making sure our girl is safe?”

  “I’m doing the best I can,” Levi told him. “It would help if she’d stop picking losers.”

  Sam took a swig from her drink. “Be nice,” she told him.

  “I’m always nice.” His gaze drifted away. “Hey, Mom’s got those cheese things.” He let her go and made a beeline across the room. Tom watched him go and then turned a wistful expression to Sam.

  “There’s no way...?”

  Sam shook her head, her throat suddenly tight. “He’s my best friend, Tom, but neither of us feels like that.”

  Tom sighed. “Well, fine then. Ruin my day. You better have a kick-ass present to make up for it.” The twinkle in his eye lifted her spirits immediately.

  “Actually, I do. Levi and I went in together for this one. Let me go find out where he’s stashed it.”

  She dragged Levi away from his mother’s cheese pastries. “Where did you put your dad’s present?”

  His gaze followed the tray as his mother circulated with it. “It’s with my jacket,” he said absently.

  “Go get it,” Sam demanded. That got his attention.

  “Now?” he asked.

  “Yes.”

  Looking nervous, he left the room, and when he came back, he had the brightly wrapped parcel clutched to his chest. Sam had found Superman wrapping paper, which she thought was fitting. Levi was still hesitating, so she grabbed his arm and half dragged him across the room.

  “Tom, it’s present time.”

  Tom turned, a delighted smile on his face, and practically snatched the present from Levi, who made a disapproving noise and muttered about manners.

  “Love the paper!” Tom said, ripping it off. “I’ve always felt that Superman and I had an affin….” He stared at the eight-by-eleven book in his hands. The cover was a photo of him asleep on the couch with his also-sleeping kids piled around him, taken over twenty-five years previously. “What’s this?” he asked.

  “It’s you,” Levi said, his voice rough. Tom shot him a look, but opened the book. The first page showed photos of him holding each of his three kids on the days they were born. The caption read In the beginning….

  He turned the page, and photos of him playing with toddlers, feeding babies, even changing a diaper brought a smile to his face. Another page, and there was the first day of school, with Tom holding each of his alternately anxious and excited children by the hand. Another, and there were sporting events and recitals, all with Tom beaming proudly from the page. Dances, graduations, family vacations, birthdays, and casual afternoons around the house, all were documented, all featuring Tom and his kids. By the time he reached the last page, his eyes were misty.

  “This—” He stopped to clear his throat. “This is a wonderful present. Has your mother seen it?”

  “Not the finished version,” Levi said, “but she helped us find all the photos.”

  “Evelyn!” Tom ca
lled. His wife looked over, and when she saw what he held, her face lit up and she hurried across the room, pausing along the way to thrust the tray she was holding into her daughter’s hands. Cara followed her mother, looking curious.

  “Oh, they gave it to you! Let me see,” Evelyn demanded, taking the book from Tom. “Ooh, the printer did a good job,” she said, paging through slowly. “Nothing’s cut off or blurry. Oh, I love that photo. I’m so glad you decided to include it,” she told Sam, who murmured agreement, her eyes on Levi and Tom.

  Tom wrapped his arm around Levi and pulled him close, placing a kiss on the side of his face. “Thank you,” he said gruffly. “It’s perfect. The best gift I’ve ever gotten.”

  Levi’s smile lit his face.

  Chapter Six

  One month later….

  Levi stretched out his legs and propped his feet on the coffee table. His attention was only half on the game, the other half listening out for Sam’s car. She was on another date with that Jack guy, the sixth one since they’d met, and even though he seemed to be on the up-and-up, Levi couldn’t help worrying a little. You heard all kinds of things about online dating.

  Besides, he wasn’t sure that this Jack was good enough for his Sam. Not that he’d met him or anything—yet—but Sam had been pretty forthcoming, and the guy just sounded like a normal dude. Sam deserved someone special, like her.

  Levi snorted. If she knew he was thinking like that, like she was some princess or something, she’d probably throw something at him. Sammy was pretty much as down-to-earth as a woman could get. She was practical, didn’t mind kicking back with a beer to watch a game, was independent, and she had those shoes with the little ankle strap that she wore with this little black skirt....

  Levi let his head fall back and remembered the last time Sam had worn those shoes and that skirt. They’d been to her work Christmas party, and before the night was even halfway over, she’d been tipsy—and horny.

  “Come on—no one ever comes in here; they’re not going to start tonight.” She shut the door to the supply closet and pushed him back against it. “I’ve been thinking about this all night.” Her hands were busy undoing his pants, her nails raking over the tender skin beneath his navel.

  “Sammy….” His protest was weak and he knew it. The idea of fucking her at her work had him so excited, his dick was practically coming out of his pants.

  She kissed him. “Shh.” She pulled the sexy top she was wearing over her head and dropped it beside them. Even in the dim light, he could see she had on one of her sexy bras, all satin and lace and revealing. His palms itched, and he yanked the cups down, plumping her tits, and ran his thumbs over her nipples. She gasped, kissed him again, and then dropped to her knees.

  Yes.

  She freed him from his pants and boxers, stroking clever fingers around his balls. Looking down, he could see her dark pink nipples, puckered and ready. Her glorious lips were parted, and her breath fanned over his cock, bringing nerve endings to life.

  She bent forward and licked him up one side and down the other. Taking the head in her mouth, she swirled her tongue over the drop of moisture at its tip. His knees weakened.

  Her mouth still on him, she looked up, and the wanton passion in her gaze as she took him deep brought him to the very edge.

  She worked his dick with her mouth and tongue, and her hands continued to play with his balls. Her touch was at first featherlight, then grew firmer, until he was pumping his hips, fucking her face, and her cheeks hollowed as she gave one long, final suck....

  Blindly, Levi shoved his sweats down and took his cock in hand, pumping roughly, smearing the moisture at the head and using it to aid his efforts. Closing his eyes, he pictured Sam later that same night, drunk and hot for him again....

  Sam’s hot, wet cunt squeezed him, clamping down the way it always did. His girl was tight as a vise. Her musky scent wafted up to him and drove him wild, and the friction of her soft skin against his hair-roughened body made him tingle.

  “Oh, Levi,” she moaned, and then her voice rose in a shriek. “Harder, more! Levi, more!”

  As he pounded into her, he focused on her mouth―her pouty, sultry red mouth, open as she panted and begged him to do her harder...

  “Ungh!” Levi’s body bowed as he came. Panting, he let his heart rate settle, and then got up and went into the bathroom to clean up. One thing about Sam, she was a hot little piece. He’d really miss that if she hooked up with this guy.

  He frowned as he dried his hands. The guy might not want her hanging out with him as much, either, and he’d miss that more. Sam was wicked awesome to hang out with. She listened when you talked, and she didn’t yammer on like other women—when she said something, it was worth listening to. She gave killer back rubs after a bad day, even without the happy ending. She made everything seem better just by being there, and he couldn’t imagine not seeing her all the time, not having her be a regular presence in his life.

  No wonder this Jack guy was into her.

  Chapter Seven

  Sam wandered around Jack’s living room. She’d offered to meet him at his place before their date because it was closer to the restaurant, and now she was indulging her curiosity while he finished getting ready.

  That was mildly irritating—it wasn’t like they were going anywhere fancy and he needed time to get dressed up. Still, if the worst thing she could say about him was that he sometimes ran a little late, things were going pretty well.

  She paused in front of the bookcase and checked out his reading preferences. There was a lot of non-fiction, biographies mostly, a few true crime books. All stuff she didn’t mind reading herself, although she liked to throw in some fiction too.

  “Hey.”

  She turned to see Jack standing in the doorway, and she smiled. “Hey, yourself. Ready?”

  “Yeah, come on.”

  In the car, he launched into a retelling of his last client meeting, with a woman who was so stupid she was almost a cliché. It sparked a memory, and when she finished laughing, she said, “You know, Levi once—”

  “Levi,” Jack interrupted flatly. Sam turned to look at him, startled.

  “What?”

  Jack sighed. “Nothing. It’s just, you talk about Levi a lot. And it seems like you’re always doing stuff with him.”

  She frowned. “Well, he’s my friend. A very good friend. We’ve known each other for years, so we have done a lot together.” She tried not to wince; Jack didn’t know she and Levi had sex, so he wouldn’t read anything into that, but the implication was very clear to Sam. Levi would have laughed.

  “I know. I just—I don’t like that you spend so much time with another guy, even if he is just a friend.” Jack’s jaw was tight, and Sam swallowed.

  “We haven’t talked about exclusivity yet,” she said carefully. “And, to be completely honest, even if we are exclusive, I’m not going to stop hanging out with Levi. He’s one of my best friends.” Although she would stop fucking him.

  A pang shot through her chest. She and Levi had been fucking for a long time. It would be weird not being able to touch him that way; even when they were just hanging out, watching TV, she liked to snuggle him.

  “I guess.” Jack sounded distinctly unenthusiastic. “But about exclusivity—I definitely want that.”

  “Me too,” Sam said, ignoring the weird feeling in her stomach. She knew what she had to do.

  # # #

  Levi opened the door to a nervous-looking Sam. “Hey. What’s up?” She followed him into the living room and stood in the middle, looking lost. “Want a drink? Sammy?”

  She started. “No. Nothing to drink. Um. We need to talk.”

  “Are you okay?” Levi’s stomach plunged. “What’s wrong?”

  She drew in a deep breath, let it out, and said quickly, “Jack and I have decided on an exclus
ive relationship.”

  Levi’s chest tightened. “Oh. Well, congratulations. That’s what you were hoping for when you started this, right?”

  Sam nodded slowly. “Yeah. And Jack’s great. I just—it means that you and I—we can’t—”

  “Yeah, I get it.”

  They stood there; for the first time ever the air between them was awkward. Levi hated it.

  “You know….” He broke the silence, and Sam jumped. He hated that, too. “You know, we never really got a last time together.”

  She blinked. “What do you mean?”

  “Well, the last time we fucked it was just.... And now you’re with this guy. So we never had a goodbye.”

  “Goodbye?” Sam sounded panicked. “No, Levi, I don’t—”

  “Shh,” he soothed, reaching out and enfolding her in his arms. “I didn’t mean it like that. It’ll never be goodbye between us. I meant a goodbye to that part of us. It just feels weird, unfinished.” He rubbed a hand up and down her back, feeling old and tired. His chest hurt. His head hurt.

  “Yeah.” She sighed, leaning into him, and he absorbed the wonderful peace and warmth that Sam brought him. Everything inside him relaxed, even as his stomach sank, knowing things were going to change. “It feels weird.”

  Chapter Eight

  “So.” Leona leaned back in her armchair. “Online dating works.”

  Sam grinned. “Yep. Jack’s great. He ticks all the boxes and I like him. You should come out to dinner with us one night, get to know him.”

  “Definitely.” Leona hesitated. “So, what does Levi think of him?”

  “They haven’t met yet.” Sam bit her lip. “Jack was actually a little jealous of Levi, you know, because we spend so much time together.”

 

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