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Back on the Horse (TWAW+leia25)

ToWriteAndWander

ToWriteAndWander

Not all those who wander are lost.
Joined
Jun 8, 2020
It should not have been as much as a surprise as it was to find his daughters best friend on the dating app she had recommended to him. Richard, a single father now aged 50, had finally decided to get back to dating. It had been years, more than he cared to remember, since he had been on a date or had had sex, but he had devoted his life to raising his daughter. Now that she was 22, she didn't need him nearly as much as she used to. She and her bestfriend, Maya, had started to encourage him to start dating, that it was okay for him to get back 'on the horse' and not spend all his time with them. Maya had recommended this particular app, so of course she used it too. He just wasn't expecting to be paired with her.

He didn't know how to use the thing and hadn't set an age range. He couldn't help but thumb through her pictures, read her bio - and swipe right. Where was the harm, right? He had never expected her to swipe right on him and for that 'match' notification to come through. The girl was beautiful, of course, but felt like a second daughter to him. They had texted about matching, about how she found it 'cute' that he had swiped right on her. And how she'd love to be his first date. No pressure that way, right? Going on a 'date' with some one you knew.

He hadn't told his daughter, of course. He didn't want to make things weird, or force her out the door sooner. She was looking at a place of her own, but he wasn't exactly prodding her out of the house. Maya had suggested a casual date - a movie and dinner. He had put on a polo shirt and a nice pair of jeans. Casual wear. Then he had driven to her house - a familiar route. Once there, he debated whether or not he got out of the car and rang her doorbell. Its what he would have done thirty years ago, but that wasn't the 'cool' thing to do these days. So he shot her a text instead, saying he was outside but to take her time.

He had classic rock on the radio, drumming his fingers on the steering wheel as he waited for her to come out.
 
Maya wasn't new to dating. She was 22, just graduated from college and she was extremely beautiful. She'd had a few boyfriends before and although she wasn't vain, she knew men looked at her wherever she went. She wasn't used to feeling nervous before a date. But for some reason, she was nervous tonight. It was just Richard, someone she'd known for years, but her stomach felt queasy as she got ready.

She showered, shaved her legs, styled her long brunette hair in a bun with a couple of locks framing her face. It was just a casual date, movie and dinner. She wasn't sure what restaurant they'd eat at but she doubted it would be the Red Lobster, the most expensive restaurant in town. Even so, she took her time applying her shimmery bronze eyeshadow and mascara. She hesitated and applied some red lipstick. It was a casual date but she still wanted to make an effort and show him that she was taking it seriously. She wanted to go on the date. It wasn't a last resort. As such, she chose a navy blue dress. She bought it in a summer sale and had been waiting for a special occasion. This was special enough. She looked in the mirror. The thin straps showed off her tanned shoulders and the V neck boasted some cleavage but nothing inappropriate. It hugged her torso and flared out towards her mid thigh. She paired it with some navy blue strappy heels and grabbed her purse.

It was just a casual date as friends with her best friend, Stephanie's, father, no less. She'd known him a while and thought the dating app might be fun for him. She had it set for herself with an older age range as she felt men her age weren't as mature as she wanted in a partner. When she saw Richard on the app, of course she swiped right. She wasn't going to deny that he was very attractive and funny and smart and mature. She'd even go as far as saying she had a small crush on him. But she didn't expect him to swipe right on her. She'd been the one to suggest the date. Movie and dinner. No assumptions that it would be anything more. They'd just be hanging out and getting to know each other with Stephanie talking which she did a lot. Part of Maya felt weird about not telling Stephanie but it wasn't really any of her business.

Maya's phone chimed, a text telling her Richard was outside. She gave one last look at her reflection and left her apartment. She saw his car outside and gave a small wave as she approached the passenger door. She slipped inside and smiled at him as she clicked her seatbelt into place. "Hey. Thanks for picking me up."
 
"No problem." He responded, unable to pull his eyes from her. She looked absolutely stunning in her dress and he found his loins warming at the sight of her. There had always been a thing there between them and tonight, well, tonight it seemed to be more out in the open. "You certainly have a way of making a guy feel suddenly underdressed." He adds with a chuckle. "You look...stunning. I feel like I should be wearing a suit!"

He gave her a warm smile and then pulled out of the driveway. It was a short drive into town, almost taking as long to find a parking spot close to the theatre. The movie she had convinced him to see was some chick flick, but he didn't mind. He had seen countless of them with 'the girls' and it if meant spending more time with her, alone, he was okay with that. It was just going to be two friends, hanging out.

Stepping out of the car, he offered her his arm as any proper gentleman would do. "I went ahead and bought two tickets so we can head right in. Want any snacks first? Oh, no, we're doing dinner afterwards so that would be a bad idea. Maybe next time." He says with a wink, leading her down the hallway and to the theatre for their showing. He picked open seats towards the back of the theatre. Not too many people would be there on a Tuesday night, but not every date had to be on the weekend.

Of course, even with the lack of people, the AC was still on and it was a little chilly. She hadn't brought a jacket and he didn't have one either. "If you get cold, you can always snuggle against me." He murmurs softly, patting her leg as he settled into his chair. The armrest between them could be flipped up and out of the way if she wanted to do that.
 
Maya had never experienced 'date Richard' before. He was always so fatherly, providing meals and snacks, driving her and Stephanie places. When Maya moved into her own apartment, he was sweet enough to even do her laundry when the machines in her building were shut down for maintenance. But 'date Richard' was sweet and charming. She enjoyed the feeling of their arms linked together.

The theatre was rather chilly and she suddenly regretted not wearing a jacket. Or a bra. Her breasts were on the smaller side and considering the dress had thin straps and a rather low back, she didn't think it was necessary. Except now when she felt her nipples hardening from the chill. Sure, she wasn't wearing a thin jersey t shirt but her dress wasn't made from fleece either. She glanced at Richard who seemed momentarily distracted by the arm on the other side of him and she glanced down at her chest. Sure enough, her nipples were visible. It wasn't a huge deal. They were both adults and she trusted him wholeheartedly. Maybe he wouldn't even notice in the dim lighting of the theatre.

She nudged the arm between them up and shifted closer to him. "I am quite cold," she admitted. She hesitated for a moment and leaned into his side, feeling his firm muscles against her slender body. He was warm, too, and she was grateful for that.

Despite how she'd always known him as a fatherly figure, this shift to 'date Richard' didn't feel as awkward for Maya as she'd imagined it would. She felt comfortable with Richard and was enjoying his company. They hadn't talked much on the drive there but it didn't matter. She was enjoying being with him.
 
He certainly didn't mind the close contact as she leaned into him. Countless movie nights, he had both his daughter and Maya leaning into his sides to cuddle for warmth, even under the blankets. It was really no different now, right? He smiled at her. "I'll keep you warm then." He slid his arm around her shoulders, allowing her to nestle in closer to him. It allowed him to feel the press of one of her perk breasts against his shoulder, making him look down.

He saw her cleavage then, the way her nipples poked against her dress. No sign of a bra. Daring, he thought, and quite sexy. It made him wonder if she was wearing any panties on underneath, or a thong or something else - or nothing. He shifted a little, feeling his loins warming again, shifting into a more comfortable position to hold her as he was as the movie started.

As the movie continued, he found himself rubbing her shoulder and upper arm with his hand. Eventually, his hand started to move closer to her neck, massaging gently, fingers splaying out to tickle over her collarbone. His thumb encountered that thing, spaghetti strap of her dress and followed it, sliding up and down even as his hand came in contact with the swell of her breast, getting dangerously close to groping her right there in the theatre.
 
Maya leaned into him and enjoyed the feeling of his arm, warm and muscular, around her shoulders. There were only a few other pairs in the theatre; it was mostly empty which was fine by Maya as it was unlikely that there would be any fussing or disruptions. They were just watching a movie. It was easy to believe they were the only ones in the theatre at all.

She'd been looking forward to this movie. It starred two of her favourite actors and she wasn't ashamed to say she loved rom coms. The trailers looked hilarious. But as Richard started to rub her arm, she found it harder and harder to concentrate. His hand was large but his touch was soft. When he started to massage her neck, she tilted her head onto his shoulder, silently indicating that she enjoyed it. And then he did more, tracing the strap of her dress. With just one movement, tugging it down her arm, he would easily expose her breast right there in the theatre. But he didn't. He moved his hand lower, closer to her breast. Her heart started racing as it became clear neither of them saw him as a fatherly figure anymore.

She moved her arm down slightly. It was subtle, he might not even notice. But if he wanted to touch her, he had more space now. Keeping her gaze fixed on the screen which showed the two main characters kissing wildly, stumbling into an apartment, she dropped her hand onto his leg, just above his knee. Her touch was light, almost delicate and teasing. But it was there.
 
Richard couldn't help but notice the timing of her hand on his leg coupled with what was going on on the screen. He felt his heart racing in his chest, realizing just where his hand was on her body. But she wasn't shying away from his touch, adjusting herself to make it clear he shouldn't be doing what he was doing. And should he do what he was doing? She was his daughters best friend, a second daughter to him...and the object of his current desires.

He mimicked her hand placement, putting his other hand on her leg, just below the hem of her dress. He squeezed her leg softly and then started to stroke it, letting only his fingers slide under the hem of her dress. As the movie continued, he decided to be bolder. He hadn't hooked up with a girl in a movie theatre since he was probably around her age. There was always something kinky about the risk of being caught, by doing things in front of other people.

So he slid his hand on her chest down even more, sliding it inside the top of her dress. He kept his eyes focused on the large movie screen even as he groped her breast. He could feel just how hard her nipple was now, his large hand squeezing her perfectly sized orb. He rubbed his thumb over it before starting to massage and squeeze her breast with his hand.
 
Maya's heart was still hammering in her chest. She wasn't a virgin by any means. She'd had sex with a few of her exes but none of them had made sex into the world changing event movies made it seem. They were selfish, always wanting their own pleasure and not caring about hers. She still wasn't sure where this night was going. They'd agreed to go as friends. And yet, the way Richard was touching her made her question everything. She forgot all about their agreement and Stephanie. If the evening went in the direction of sex, she knew she'd say yes to just about anything. Part of her was willing to ride him right there in the theatre.

She felt his hand rest on her leg, his fingers rubbing her smooth skin just under the hem of her dress. And his other hand finally moved, slid into her dress and cupped her breast, his strong fingers digging into her skin. She felt him squeeze and tug on her nipple and massage her breast. Her head was still resting on his shoulder and her eyes fluttered closed. And then it happened. She let out a moan. It was louder than she anticipated but the movie drowned it out, though Richard was sure to have heard. It let him know that was enjoying everything he was doing to her in the back of that movie theatre.

She felt her lacy underwear getting damp. She was almost aching for the hand on her leg to move higher, to touch her more. Was she really wanting to fool around in a movie theatre? She felt his palm rub her nipple again and she moaned once more. Her body had never felt so hot before. She dug her fingers slightly into his leg as she part her own legs, a silent invitation that she wanted whatever he was willing to give her.
 
Stephanie would kill him if she ever found he was groping her best friend. But at her age, there really wasn't anything wrong with having a little fun was there? And that moan - that was the first moan he had heard in a long time. Despite himself, he felt his cock starting to grow erect in his jeans, even as her hand clenched at his thigh. Her breast fit perfectly in his hand so he continued to toy with it, massaging and squeezing and occasionally rubbing or tugging that hard little nipple of hers.

He felt her spread her legs for him then. He wasn't coy about it, sliding his hand the whole way up her dress to rub her between her legs. He could feel her lace panties then - making him wonder if she was shaved, trimmed, or hairy. He supposed there was only one way to find out. He could feel the heat of her arousal radiating from her pussy, her panties already growing damp - and he had only felt up her breast!

He pulled her panties to the side and slid his hand directly over her bare sex. It was the first pussy he had touched since his wifes. His cock was rock hard in his pants now. He stroked over her folds, paying special attention to her clit before sliding a finger into her. Her pussy was tight even around one finger. He could only imagine what it felt like around his cock.
 
It was happening. It was really, truly happening. Maya was fooling around in the back of the movie theatre. She felt him press against her panties, then he pulled them to one size and then he ran his fingers over her shaved pussy. And then his long finger was inside her, curling slightly. She was wet and tight. It was clear her exes hadn't been overly large. She twisted her head slightly, pressing her mouth into his shoulder, muffling her moans.

After a few moments, she lifted her head and met his gaze as his one hand massaged her breast, his other between her legs. There were so many reasons why they shouldn't be doing this and yet, part of her hated that they'd waited so long. She held his gaze and rested her small hand on his crotch, feeling his hard cock inside his pants. Without saying anything, she started unbuckling his belt, intent on returning the favour.

She slipped her hand into his pants, wrapping her small hand around his shaft. But then she paused. She heard moaning but it wasn't her. She glanced at the movie and saw the two main characters in a wild sex scene. The woman was being fucked against the wall, her moans wild and passionate. She looked back at Richard and blushed, though she didn't know if he could see it in the darkness.

"Richard," she breathed as his palm brushed her nipple once again.
 
His cock was anything but small - something she'd notice as soon as she put her hand on it. It had been ages since some one other than himself had touched his hard cock. He met her gaze, eyelids heavy with lust and desire. He continued to work his finger inside of her, sliding it back and forth as he lewdly fingered her in the theatre. Then she was undoing his pants and slid her small, warm hand into his boxers, grabbing his shaft. She'd barely be able to wrap her hand around it and - if measured - his shaft was nearly 10 inches long. It seemed like he was packing quite the package.

He didn't notice the sex scene on the screen, enamored as he was with her. He slid his hand from her breast, only to put it on her other breast to make sure it wasn't neglected. He tweaked its nipple, losing focus on their surroundings. But there wasn't much time left in the movie.

He slid a second finger into her tight pussy, rubbing her clit with his thumb. He moved his fingers back and forth as she stroked his cock. "Mara..." He murmurs back. What did he say? His eyes widened though as the movie came to its end. He quickly pulled away from her, doing his pants back up as the end credits rolled. "Shit, that was close." He says, letting her readjust herself. Normally, he left during the end credits but he needed every last second to get his erection under control.

Once the lights were fully on, he stood up and took her hand, leading her back out and into the hallway. He needed some fresh air, taking her outside onto the sidewalk - still with her hand in his. He pulled her against his side. "So...thinking of anywhere specific for dinner?" He asks, ignoring the fact they had just fingered each other in the theatre. His heart was still pounding.
 
When the lights came on, Maya pulled away from him as if she'd been hit with an electric shock. She hadn't been aware that the movie was ending. She'd been extremely close to riding him right there and then. She took a moment to adjust her dress and underwear while he tucked his cock away. His cock... She hadn't been able to see it but she hadn't been able to wrap her hand the whole way round. She was suddenly struck by the fear that if they did have sex, he wouldn't fit inside her at all.

However, before she could dwell too much on that, Richard took her hand in his and guided her out of the movie theatre, into the cool evening air. They were walking along the sidewalk, among other people who were completely unaware that just two minutes ago, Richard's fingers were deep inside her pussy and she was aching for them to be inside her once again. In fact, she wanted another part of him entirely inside her, even though she genuinely didn't think he'd fit.

It took Maya a moment to realise that Richard was talking to her. She looked up at him with wide eyes and tugged on his hand so he stopped walking. "You're thinking about dinner?" she blurted out. She searched his eyes for a moment. "Richard," she whispered. "I don't want dinner."
 
Richard blushed at her words and nervously glanced around, but no one seemed to hear or care what they were talking about either. Could they really have sex? The two of them? He was old enough to be her father. But what had happened in the movie theatre was answer enough. So he squeezed her hand and led her back to his car. Once inside, he reached over and put his hand on her leg.

He turned to her, sliding it up under her skirt again to rub at her pussy. He pulled her panties to the side once more and began to finger her again, wanting to keep her wet and aroused. "Where do you think we should go?" He asks her softly. "Stephany is home, so we can't go back to my place. We could go to Murphys Park..." Which meant sex in the back of his car, a frequent occurrence at Murphys Park, especially among younger people.

He didn't even think about her place. He'd be happy to go anywhere really, even book a motel even if for just a few hours.
 
Maya thought they'd go straight to her place and hadn't expected him to figure her again right there. As such, she cried out in pleasure as his finger worked in and out of her wet pussy. Without really thinking about it, she wrapped her arms around his neck and kissed him. It was wild and passionate, her tongue darting straight into his mouth. Honestly, if he kept doing that with his fingers, she was going to orgasm right there in his car.

After several moments or maybe hours, she pulled back breathlessly and met his gaze. "My place," she whispered breathlessly. "I'm...I'm close."

She could feel his finger thrusting, curling inside her pussy. She'd never felt like this before. The pleasure was hot and intense, not like when her exes had tried to pleasure her. She dug her fingers into his shoulders as her body tensed. She was so wet now, she could feel a wet patch forming on her dress. He continued to finger her and the heel of his hand brushed her clit.
 
Her kiss took him by surprise but he kissed her back. He hungrily sucked on her tongue before pushing his into her mouth. His other hand reached over and pushed the top of her dress down to reveal one of her breasts. He mauled it with his hand all the while continuing to finger her. He hadn't been laid in forever and now he was working his way to fucking his daughters best friend.

He pulled back and nodded his head, continuing to finger her even as he started up the car. He left her like that, her breast exposed. "You certainly are..." He murmurs before heading back they way they had come some two hours earlier. For all this time, he had never actually been inside of her place. The closer they got, the faster he pumped his fingers in and out of her.

He pulled into her driveway soon enough, only then pulling his fingers from her. "Lead the way." He says, his own cock tenting the front of his jeans even as he slid out of the car. He was giddy again, about to do something he didn't think would ever happen again for him.
 
Maya was completely breathless when they pulled into the driveway. She took a moment to fix her dress and pulled her keys from her bag. She led the way into the building and up two flights of stairs and honestly, she'd never climbed those stairs as fast as she did in that moment. She pushed the door open, revealing her apartment. It was small but tidy. The lounge just held a small sofa and a TV with a few art prints on the wall.

Without saying anything, she took Richard's hand and pulled him through to her bedroom. The double bed was covered in a blue floral comforter and the walls were painted a pale blue. A bookshelf set across from the window was stacked haphazardly with many titles. Aside from the small pile of crumpled clothes in the corner which she'd forgotten when she did her laundry, the room was immaculate.

She turned to Richard and wrapped her arms around him, once again kissing him wildly. As they kissed, she slipped out of her shoes, losing several inches in height so she had to crane her neck to continue their kiss.
 
Richard followed her into her apartment. It was small but tidy. She wasted no time in pulling him to the bedroom. The time to back out had long passed by now. He barely had time to look at her belongings before she pressed herself to him. He kissed her back, once again pushing his tongue into her mouth. His hands roamed her body, groping her ass and rubbing up and down her back. He found the bow to her dress at the back and tugged at it until it gave way, letting her dress fall to the floor.

He didn't stop kissing her, moving his hands to her panties. He pushed them down as well, until gravity took care of the rest. His hand was between her legs a moment later, rubbing her slick folds. She was ready. If ever a girl was looking for a dicking, she was certainly that girl. Then he bent down and swept her legs up with his arms, picking her up. He tossed her onto her bed.

Her pulled his shirt off then, revealing his aging 'dad body'. His barrel chest was big and burly, with short hair all the way down to his navel. But he was solid, not chubby, and kept his looks. He did all he could to keep in shape but at his age, there was only so much you could do. He stared at her naked body with lust before crawling up onto the bed on top of her. He laid on top of her, his legs between hers and continued to kiss her.

He reached down and undid his own pants, pushing them down along with his boxers, unable to push them past his knees. But that was all he needed to free his engorged cock. Unlike her shaved slit, only his balls were smooth. He trimmed his pubes - specifically for his new 'dating' mindset incase he did get lucky. But at his age, shaving the whole works was too much. Of course, with his body on hers and mouth to mouth, she wouldn't be able to see this.

Instead, she'd feel him rubbing the head of his cock against her slick slit before pressing into her opening. He moved his hand away and then thrust forward, spearing the tip of his cock into her. He moaned with pleasure, continuing to thrust into her. He didn't stop until his bare cock was buried to the hilt inside of her, the first pussy had had fucked in years. He pressed his weight down on her, making sure he was as deep as he could go, his balls pressing up against her.

He pulled his mouth from hers then, looking down at her. "Fuck...I'm inside...of you..."
 
Time seemed to move much too fast but also seemed to slow down as he continued to touch her and kiss her. When he threw her onto her bed, she shuffled back against the pillows, watching him strip off his shirt. He wasn't in his twenties. But he was toned and firm against her slight body. He wasn't like the other men she'd dated and she liked that.

Then he was on top of her, his warm body pressed against hers. And then it happened. His cock was inside her. Really, really inside her. She'd thought her ex was large but it was nothing compared to this. He was long and thick, touching parts of her she swore she hadn't known existed before tonight. Honestly, it was slightly uncomfortable, almost painful but in a good way. She was extremely wet, at least, which made it easier for her.

Richard pulled away from the kiss and she looked up at him with wide eyes. She lifted a hand, stroking his cheek. "You're inside me," she whispered. "I...um....well....you're bigger than all my exes," she admitted eventually. "I...Can we take it slow?"

Her cheeks were flushed. After all her confidence in directing him to her apartment and into her bedroom, she was kind of embarrassed by admitting how large he was compared to her past lovers. "You feel amazing but it's...a lot. I had no idea you were so big."
 
Richard liked her admission. What guy didn't like being told he was 'big', especially if he was 'bigger' than anyone else she had ever been with. So he lay there on top of her, his big, hard cock buried to the hilt in his daughters best friend. It was a wrong on so many levels but at the same time, it felt so right. Her petite, smaller body seemed to fit beneath him perfectly. Her pussy around his cock felt like a glove.

But she wasn't complaining that it hurt, or that he should stop. He smiled softly down at her, letting his eyes wander to the gap between their bodies - looking at her breasts, her flat stomach, and then where his cock disappeared into her pussy. He rested his weight on his knees and elbows, almost holding his body in a plank above here. It had been a long, long time since he had felt the sensations he was currently feeling and it felt amazing. He flexed his cock inside of her.

"Yeah? Do you like having my big cock in you?" He moans softly down to her. "Its been...forever...since I've been with anyone. You...you feel amazing around me." He started to thrust then. He moved an inch or two of his cock out then pressed it back in. Slowly. He started to pull further and further back with each thrust, thrusting back in before resting for a moment, before doing it again. "I can't believe I'm fucking you right now."
 
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