Playboy Ever After

by Chance Carter

  They’d gone out for dinner the night before, their third date. Nora had gone into the evening fully expecting it to be as hot, if not hotter than the date before, and Leo did not disappoint. He took her to a romantic little rooftop restaurant with a gorgeous view of the city. She liked that he pulled his chair close to hers so they could sit intimately side by side, instead of across from each other. Leo was a great story teller, and while they didn’t share anything too deep or personal, he was still engaging and funny. Nora appreciated the quick-witted banter they both seemed to enjoy, and she easily kept up with him. She could be cheeky with Leo because he really seemed to enjoy her teasing. On top of that, they had an undeniable physical chemistry. It was obvious all though dinner that both of them were itching to get their hands on one another. His soft caresses and kisses throughout the evening drove her crazy. She couldn’t ever remember a time in her life that she felt so sexually charged. Leo seemed perfectly pleased with himself and the effect he was having on her, and really enjoyed teasing her as well.

  At one point in the evening she had felt particularly daring. Leo had just given her one of his delicious kisses as the waiter had come by to check on them. They had just finished their coffee and were anxious to get home, both of them feeling worked up. Nora let her hand slip over Leo’s lap and slide gently up his thigh until she found the prize she was looking for. The look on Leo’s face was priceless as he tried to stay composed while the waiter was asking if they wanted anything else. She massaged his cock through his slacks as discreetly as she could, enjoying the stiffness of him under her touch. She loved torturing him and had to stifle a giggle when Leo’s voice cracked as he requested the check.

  After the waiter left, Leo turned to her and whispered in her ear that she was being a very naughty girl. That probably shouldn’t have turned her on as much as it did, but fucking hell it made her hot! She left him at the table and went to freshen up, and then they hightailed it out of there. There were a few other patrons in front of them sharing the elevator ride, but that didn’t stop Leo from kissing her. She waited for just the right moment and then slipped her damp panties into his pocket. His eyes and his grin, widened when he realized what she’d given him. He put his arm around her waist and pulled her closer, then lifted her dress slowly from behind, exposing her bare backside. The thought of getting caught was both horrifying and exhilarating at the same time. If anyone turned around they would have been busted!

  As worried as she was, she didn’t want him to stop. Her heart was pounding in her chest, and the adrenalin coursing through her only served to heighten her desire. He slid his hand between her legs, trailing his fingers up her thigh until he found her dampness. She sucked in her breath hard, making a loud enough noise to draw a playful warning look from Leo. His long reach allowed him to gently brush her clit before he slipped his fingers into her soaking wet hole. God, she could have cum right then and there!

  She didn’t even remember the ride home, she had been so worked up, and as soon as they walked into her apartment Leo had her off her feet. He carried her straight into the bedroom, kissing her all the while, until she felt herself dropping back onto her mattress. He grinned at her sheepishly before burying his face between her legs, as if he couldn’t wait even one more second to taste her. His velvety tongue traced her folds tenderly, eagerly lapping up her juices.

  Normally, she was too shy to allow a guy to go down on her, but Leo made her feel wild, impulsive and daring. Besides, she didn’t think he would stop even if she’d asked him to, and that alone aroused her even further. It was as though he wanted to swallow her whole. She was so swollen with desire that as soon as he plunged his fingers into her she came for him. He must have approved because she could hear him moaning between her legs.

  She would have loved to return the favor and taken him into her mouth, but he was too impatient. As soon as she helped him unzip his pants he slipped them off and eagerly pushed her back onto the bed. When she playfully tried to protest, he just smiled wickedly at her and brought his lips down on her hard, his tongue filling her mouth. She could taste herself on him, but she didn’t care, she craved his kisses. He expertly tore the wrapping off a condom with his teeth, and then quickly rolled it over his erection. He had the look of a man on the brink of madness, and she could only assume it was driven by his own insatiable need. Within seconds he had buried himself into her, his cock filling her completely. She rocked in perfect rhythm with him as he plunged himself in and out, her legs wrapped tightly around his waist.

  Without a doubt, they would have other opportunities to fuck each other, but in that moment there was no question of who was in charge. Leo was a man who knew exactly what he wanted, and even more importantly, how to get it. And he could back it all up with his skills. He left her breathless as he desperately fucked her, positioning himself at exactly the right angles for her to feel the full pleasure of his cock. She grabbed his ass just as an orgasm coursed through her, her body rocking and shaking uncontrollably. That must have been more than Leo could take because in that same delicious moment he released his own passion as though he’d been holding onto it by a delicate thread, and on his last deep thrust he spilled his seed.

  They held each other for a few minutes, catching their breath and enjoying the afterglow of their pleasure. She smiled up at Leo while he brushed the hair out of her eyes. She liked the feel of his weight on top of her, oddly it made her feel warm and protected. Finally, Leo rolled himself off of her, leaving a chill where his body heat had been. She shivered and pulled the covers up around her while he went to the bathroom to clean up.

  As Nora waited for Leo to return, she wondered whether or not he would spend the night. It wasn’t that she needed him to sleep over to validate her or the relationship, but it had been so long since a man had warmed her bed, she welcomed the thought. As soon as he came back, he slipped under the covers and pulled her close. She lay her head against his chest waiting for him to speak, but he just held her in silence. Soon, his breathing slowed to a deep and rhythmic pace, and she knew he had fallen asleep.

  She drifted off to sleep herself until a full bladder woke her up. It was close to 2:00 am and Leo was still sleeping beside her, snoring peacefully. She gently slipped out of his embrace, careful not to disturb him, and went into the bathroom to freshen up herself. She washed the makeup off her face and brushed her teeth before returning to bed. Again, she did her best not to wake him, but to her surprise he seized her by the waist and pulled her toward him. His naked body was warm against her own, his soft chest hair tickling the sensitive flesh of her back. He moaned quietly in her ear, and spooned even closer to her. She could feel his erection swelling against her skin, gently flicking and teasing her pussy from behind. Leo reached his hand down and lazily massaged her mound, heating her up all over again. Nora sighed deeply and opened her legs, inviting his cock to tease her, flesh to flesh. She placed her hand over his and applied the pressure she needed, guiding him to the perfect spot.

  Leo must have appreciated the gesture because he growled some naughty words in her ear and pulled her ass up towards him. Nora couldn’t help but giggle, loving his response. He kissed the back of her neck, gently grazing her flesh with his teeth. This sent a volt of pleasure straight to her womb and she gratefully moaned her approval. He skillfully kneaded her pussy, slipping the tips of his fingers into her, in and out, in and out, until her climax reached its peak. She grabbed his hand and held it in place, while another orgasm surged through her, spurred on by Leo’s whisper.

  “Cum for me, Nora.”

  While she took a moment to recover, Leo must have retrieved another condom and placed it over his still hard shaft. He snuggled up beside her and took her from behind, his cock finding her swollen and ready for him. This time he fucked her slowly and tenderly, his free hand trailing up and down her body as far as he could reach. As much as Nora enjoyed the sleepy sex from behind, she wanted to move more freely and enjoy his body. She wiggled hers
elf away, allowing his cock to spill out of her and then rolled over to face him. She kissed him fervently, shifting him on his back, straddling herself over him as she nibbled, sucked and scratched down his neck and chest, stopping to graze his small buds with her teeth. Leo groaned quietly as she reached between her legs and grabbed his cock, positioning it perfectly so she could skewer herself down on him. From this position she could feel the full length and girth of him inside of her as he filled her to the hilt. With her new found confidence, Nora rode him hard until they both came again, pleasured, exhausted and content.

  She hadn’t slept long after that, but she slept well, wrapped in Leo’s arms. They woke when the alarm chimed on his smartphone. He squeezed her breast and gave her a kiss to the top of her head... then headed to the kitchen with the promise to return with coffee.

  Nora stretched again, a smile on her face from the memory of an awesome night, and waited for Leo to return. There was so much she wanted to talk to him about in the short time they had before work.

  Chapter 12

  Leo

  It was no surprise to Leo that Nora’s kitchen was clean and organized. He had very little trouble finding everything quickly and easily to make a pot of coffee. He sleepily leaned himself against the counter, wishing he had a few more hours to lay around in bed with her. While he had the morning off, she told him she had to be out the door by 7:30 if she was going to make it to work on time.

  Typically, he didn’t like to spend the night with a woman after sex. It just left the wrong impression. In his experience, women usually read too much into it. He stayed overnight with Nora for two reasons.First, she was not like most of the women he dated. She was intelligent, mature and interesting. He liked that she was witty and not overly sensitive, so he could tease her without her taking it personally. Corrine had been that way too. The truth was that she held his interest beyond the sexual chemistry they obviously shared. She made him feel like he needed to step up his game, to make sure she knew he was not just fucking around.

  The second reason he stayed? He had been so worked up the first time they had sex it had ended almost before it started. He didn’t want to leave her with the notion that he was a two-minute man. That would just be fucking embarrassing. So, by all accounts, he crashed overnight to make sure he left her with a good impression.

  He really liked Nora. She challenged him and if he was being honest, he was pushing himself out of his comfort zone because of his attraction to her. Whether that was good or bad was still undecided. Last night was fantastic, but he was concerned his feelings for her were developing too rapidly. He wasn’t sure he was ready for that. He knew he needed to be clear with her about his feelings, because a woman like Nora would settle for nothing less. He just wasn’t sure how to tell her without spooking her or pushing her away. He still wanted to hang out with her, but he wanted to keep things casual until he knew for sure that his feelings for her were genuine.

  Leo grabbed two mugs out of the cupboard and poured coffee into both of them. He remembered that Nora took hers with a little milk and sugar and prepared it the way she liked before making his way back to the bedroom. Nora was sitting up in bed in her bathrobe. He smiled, once again recalling the night of their first meeting, noting how damn lucky it was that he had been in the right place at the right time. A few minutes before or after and he may never have met her. Maybe it was fate, he wondered casually.

  He handed her a mug and sat down beside her, giving her a quick peck on her pretty, full lips. It was remarkable that she looked just as beautiful in the morning, with not a stitch of make-up, as she had all dolled up the night before. He liked that she looked mussed up and satisfied, and even better that he was the lucky bastard that had made her look that way.

  “Thank you for this.

  ” Nora held her mug up in a ‘cheers’ motion before taking a careful sip of the hot beverage.

  “My pleasure,” Leo assured, offering her a quick wink.

  “All of it.”

  Nora smirked playfully, shaking her head at him, as if to bring his ego down a notch.

  “That was quite a night. I know I enjoyed myself a lot. I’m happy you decided to sleepover. It was nice waking up beside you. And serving me coffee in bed? I could get used to this,” she teased, holding her hand out to him. Leo looked at it for a few seconds too long before taking it in his own. He wondered what she was thinking about, if she had read too much into him staying all night.

  “Well, what can I say, I like serving you,” he growled, raising her hand to his lips. He kissed and nibbled her fingers seductively, his eyes suggesting he wanted to taste more.

  “Did you have a good night?” she asked guardedly.

  Leo had enough experience with ‘post-sex’ conversations that he knew what Nora was looking for. She wanted validation that he was still interested, that his expectations had been met, and that it wasn’t just casual sex. She wanted to know if they were on the same page. This was usually the part when Leo would ‘buddy’ them up, keep it light, talk about how much ‘fun’ they’d had. He was good at smoothing things over so that they both parted ways happy, with their egos in check. Hell, most of the time they came back for round two or three, despite the fact that there was no promise of anything more than friends with benefits.

  But he didn’t want to have that conversation with Nora. The problem was, he wasn’t exactly sure what he did want.

  “I had a great time. I did,” he offered carefully, pausing to process his thoughts.

  Nora just looked at him warmly, waiting patiently for him to speak. She wasn’t going to make this easy for him either, which was one of the things he dug about her.

  “Can I be honest with you?” he finally asked, setting his mug down on the bedside table.

  Nodding, she said, “I would hope for nothing less,” her eyes suggesting she was more curious than wary.

  “I really like you, Nora,” he began, trying to find the right words so he wouldn’t sound like a complete asshole. “I’ve never been much for monogamy, I’ve been playing the field for a long time now. I’m not sure I would be any good at it.”

  He met her eyes for a moment or two, trying to gauge her reaction. She didn’t look hurt, or shocked, or even surprised, but instead she looked rather patient. This encouraged him to continue.

  “I’m not sure how you are feeling about this,” he said, gesturing between them, “but I’m feeling really good about it. I want to see where things go between us, but the truth is, I have a hard time committing to one woman. I’m not saying that I don’t want to, but that I’m not sure I know how. I guess I’m just asking for a little time to see how things develop. I don’t want to rush things.”

  “Leo,” Nora whispered, gently squeezing his hand, “it’s ok. I’m not asking for a commitment. We’ve only been out a few times, and granted they were awesome as dates go, but I don’t want to jump into anything too quickly either. I want us to get to know each other better, and see if our chemistry extends beyond the bedroom. There’s still so much to learn about each other.”

  Leo nodded at her, surprised but grateful that she seemed to understand. Maybe she would make it easy. She had a maturity about her that seemed to go well beyond her years…, what some people referred to as an old soul.

  “Then we agree. Let’s hang out some more, maybe go dancing again?” he grinned, leaning in for a kiss. She put her mug down and took his face in both hands, they were still warm from holding the coffee cup. It felt comforting. She kissed him sweetly, lingering just inches from his mouth as she stared into his eyes.

  “Thanks for being honest with me,” she whispered.

  “Of course,” Leo replied, drawn in by her gaze. She was bewitching him, he thought humorously. She released his face and he slowly straightened himself back up, but not without wondering whether or not they had time to fuck again.

  “I wanted to bring this up with you myself. I’d love to spend more time with you Leo, for sure. I real
ly like you too, we have so much fun together. But while we are keeping things casual, I think we could also see other people, at least until we agree that we would like to take things to the next level, if that ever happens. What are your thoughts about that?” she asked cautiously, picking up her mug and taking another sip of coffee.

  It seemed sensible to Leo, especially since he seemed to be the one that needed an escape hatch, but for a brief moment he felt jealous at the thought of Nora dating anyone else. He knew it was stupid to think that it was okay for him to play the field and not her, but in a perfect world that was exactly how he wanted it.

  He nodded and chuckled awkwardly, inwardly chastising himself for being a sexist jerk.

  “Makes sense to me,” he agreed quietly, reading her face for more clues. Was she really okay with this or was she just telling him what she thought he wanted to hear? Nora reached out and gave him a hug, then kissed him on the cheek, as if to reassure him.

  “Good. I’m glad we talked about this. I was wondering when we would finally talk about something a little more personal and intimate,” she purred, kissing him sensually, the heat from the coffee lingering on her lips.

  As inappropriate as it was, in that moment of honesty between them, he couldn’t help but think about how her warm mouth would feel swallowing his cock. Not a gentlemanly notion at all, yet he found himself aroused all the same. He wondered if he could shift the conversation to oral sex without looking like a complete jackass.

  “I think I’m going to jump in the shower,” she told him, gently prying herself away. He pulled her back and whispered in her ear, asking if he could join her. She nodded her consent, her eyes glistening with desire, as he helped her off the bed and led her to the bathroom.