Single Dad’s Plaything: A Single Dad First Time Billionaire Romance

by Natasha Spencer

  His head started to swim and he felt a little drunk. He picked up his phone and looked at it. He brought up Kalyn’s profile and looked at the video of the drunks. The dog, a Shiba Inu was Japanese. The word Shiba meaning brushwood and was a type of tree whose leaves turned red in the fall similar to the dog’s coat. The dog had a small diminutive stature and was sitting silently in the video while Morrissey sang out his song.

  The video had repeated itself a dozen times when he got the buzz. It was Kalyn.

  “You up,” the text read.

  Gary’s fingers flashed across the screen.

  “There is a light that never goes out.”

  “So that means you are still up. I decided to head into San Francisco. I wanted to meet up with my friend. We got a drink and she went home. Are you around,” Kalyn had written.

  “I am. Did you want to meet,” Gary wrote. He looked at his clock. It wasn’t that late, eleven at night. He could still meet up with Kalyn.

  “Sure. If it’s convenient. Where do you live?”

  “Why don’t we go to the Redwood room. It’s near Union Square.”

  “Okay. I’ll take an Uber over. I should be there in 30 minutes,” Kalyn texted.

  Gary didn’t know what had changed her mind. Maybe this would be a platonic meeting, maybe this would be something more again.

  Gary made a call to the hotel, the Clift and booked a room. He wasn’t sure that he would be sharing it with Kalyn but he wanted to be ready just in case.

  Before he left he looked into the bedroom. Joy was still passed out the champagne bottle sat half full on the night stand along with the glass of water. Both had been untouched. She snored lightly. Gary went into the bathroom and took his wedding ring off. The ring was simple and platinum. It had their anniversary printed along the inside. He twirled it in his hand before he put it into the drawer. He wanted this. He turned off the lights in the apartment and walked out of the door.

  Gary got to the hotel before Kalyn and checked into the room. It was a private apartment on the top floor. The room had custom furniture made of wood and Venetian glass. The bed had 300 thread count bedding and a down duvet. Everything was state of the art and new. He plopped down on the bed waiting for Kalyn to message him or call. It seemed like forever but was only five minutes.

  “I’m here, where are you,” she’d texted.

  “Be right down.”

  “Down,” she texted back.

  He locked the apartment up and took the elevator to the lobby. The elevator doors opened and he caught sight of her from across the room. She was standing by herself in the lobby. His breath was taken away. She looked magical. She was wearing heels and a maxi dress. The pink dress was off her shoulders with the straps around her biceps. The criss cross lacing on the front hinted at her ample cleavage and the dress fell to her mid-thigh. It had a light look to it. Gary could feel his cock throb when he looked at her.

  “You look great,” he said to her.

  “Thanks. I’m maybe a little overdressed,” she replied.

  “Not at all.”

  “So, you live here,” Kalyn asked.

  The two still stood in the lobby and so Gary pulled on Kalyn’s arm leading her to the bar.

  “No. I just have a room here.”

  “Oh. A room by yourself,” Kalyn said.

  “Yeah. For tonight, at least. I wanted to get away from the house and everything.”

  “It must be nice to be able to do things like that on a whim.”

  “Having money has its perks,” Gary said.

  Kalyn nodded. He could tell that she was nervous and was a little stiff. They sat at the bar which was composed from a single redwood tree. The bartender came over and the two ordered drinks. Gary got a manhattan and Kalyn ordered a margarita.

  Kalyn played with her straw, stirring the ice cubes around. Gary wasn’t sure what to say to her.

  “Thanks for coming over,” Gary said.

  “Yeah. To be honest I was thinking about the other night more.”

  “What were you thinking,” Gary asked.

  She turned in her chair and uncrossed and crossed her legs. Her body was turned so it was facing him. The two were parallel to the bar. Gary spread out his legs and Kalyn put hers between his. She leaned forward and kissed him on the cheek.

  “I think I’d like to do it again,” she whispered into his ear.

  “I think I’d like that,” Gary replied.

  “I want you inside of me,” Kalyn said. “I know you’re married but I couldn’t stop thinking about you. I want you. I need you.”

  Gary put his hand on her thigh. Her leg felt smooth and silky. He yearned to push up her dress and fuck her right there and then. He waved at the bartender and settled the bill quickly. The two took their drinks and headed to the elevator. The doors opened and shut. They were going to the room.

  Chapter 9

  Gary leaned over and kissed Kalyn just moments after the elevator door shut. They were tied to each other when the elevator stopped. The doors opened and another couple entered. Kalyn pulled away from Gary guiltily and looked down. A small smile crossed the lips of the man when he saw the two. The couple went up three flights and then got off. Gary and Kalyn stayed in the elevator for another five floors until they reached the pent house private apartment.

  Once they were inside, safe and alone, they both visibly relaxed. Kalyn went over to the window and looked out.

  “You can see the whole city,” she said.

  “Yes. It’s beautiful, isn’t it?”

  “Yes. I don’t think I’ve ever seen it like this before.”

  “It’s not as beautiful as you though,” Gary said.

  He was behind her and Gary gently placed his hands on her shoulders. Kalyn kept her gaze on the brightly lit horizon as she felt Gary’s lips touch her neck. The small hairs on her neck began to stand and her skin prickled as she felt her lips on her neck. Kalyn could feel the heat of his body and she felt it even more when his hands slipped up the side of her dress pushing it up. He pulled her close to him. Her ass smashed against his pelvis and she could feel his hard erection.

  Gary traced a path up to her earlobe from her neck with his tongue and began to gently suck on her earlobe.

  “That feels good,” Kalyn said. She hummed to herself for a moment as she felt a growing wetness between her legs.

  Kalyn turned around from the beautiful view and stepped into Gary’s arms. They kissed tenderly. Gary was becoming impatient though and his hands pushed her dress even higher. His hands massaged the mounds of her breasts and he squeezed at her nipples over her bra. Her nipples were puckered and pointing. They pushed through her bra. She moaned with pleasure in his ear. Kalyn tilted her head back and pushed her pelvis forward. Gary had enough and turned her back around. He pulled on her dress’ zipper and her Maxi dress fell to the floor. He then deftly undid her bra. Her large breasts swung freely. He grabbed them from behind and kneaded them.

  “You have beautiful breasts,” Gary said. “They feel good in my hand.”

  Kalyn said nothing and instead moaned. She was wearing only her lacy panties and her high heels. Gary was still fully clothed.

  “I like when you pull on them. I like the way it feels when you massage them,” she whispered.

  Kalyn turned back to face him. The lights of the street came into the room and bathed her in a soft light. Gary saw a beautiful face before him. Her hair was short but well arranged. Her breasts with swollen nipples pointed out at him and he could see the dampness between her legs.

  Gary bent slightly and kissed her nipple. He took it into his mouth and tugged at it slightly with his teeth as Kalyn ran her hands through his hair.

  “Lick it,” she said.

  He took his tongue and ran circles around her breasts. After a minute, she pulled him off her breasts.

  “I want to feel you inside of me,” she said.

  Kalyn didn’t have to wait long as Gary took off his clothes quickly. His har
d cock sprang to attention. She took his cock into her hand and began to slowly massage it. Precum leaked out of it. She rubbed a circle around the head. She then took her cum covered fingers and put them into her mouth.

  “It tastes so good,” Kalyn said.

  “I want to taste you,” Gary said.

  He dropped to his knees and opened her thighs. He slipped her panties to the side to reveal her wet pussy. Cool air from the air conditioning pressed against her skin and again she ran her fingers through Gary’s hair.

  Gary buried his face into the haven of pussy. She could feel his tongue lap up her juices and his tongue slide into her opening. He pushed his tongue deep into her and then pulled out delicately circling around her swollen clitoris. Her hips pushed against his mouth to meet his tongue.

  “Oh god, oh god,” Kalyn said as her head fell backwards. She wanted him to keep going but she also wanted to feel the hardness of his cock in her. Gary took her ass cheeks into his hands and pushed her into him.

  Kalyn could feel her body contract as the pleasure of orgasm ran through her. She gushed out pleasure and Gary licked it all up. He lapped at her pussy greedily.

  When Gary had licked ever drop of her wetness he scooped her up into his arms and brought her into the bedroom.

  He threw her down onto the bed. She pulled off her panties and Gary kissed her. She loved the taste of her juices on his mouth and it excited her even further.

  “Fuck me, fuck me,” she said.

  “Take my dick in your hand,” Gary said.

  She began to slowly corkscrew his penis up and down. She could feel its hardness. It

  throbbed with strength. She guided it into her waiting pussy. It filled her. He pushed deep into her

  wet cunt. The moist tip of his cock flooded into her wetness. Her cunt gripped onto his cock as it went impossibly deeper into her.

  “Oh god,” Kalyn said. “It feels so good.”

  Gary pushed her legs back so they were over her head and he drove himself into her even deeper.

  “You like it deep,” Gary said.

  “Yes. I like it deep and hard,” Kalyn said.

  “You feel so good,” Gary moaned.

  “Fuck me, fuck me hard and deep,” Kalyn said.

  Gary needed no encouragement. His face screwed into a mask of determination as he pushed in and out of her. His lifted his hips and then slammed down into her. Kalyn could feel herself getting wetter and wetter and felt the approach of another orgasm.

  “You’re going to make me cum again,” Kalyn said.

  She loved the sight of him over her. She could see his large cock ram into her. Each time he pulled it out it was covered in her wet juices. Her feet were high in the air and she put them over his shoulders. He licked at her leg as he pushed into her again.

  Gary could feel his balls tighten and lift into his body.

  “I’m going to cum,” Gary said.

  “Cum on my breasts. Shoot it all over my body,” Kalyn said.

  Gary pulled his hard cock out and it spasmed. His whole body went rigid for a moment and then relaxed as a stream of cum landed on Kalyn’s body. It coated her breasts and stomach. She took her finger and played with the cum, pushing it over her nipples and then into her mouth.

  “Oh god, oh god,” Gary heaved. He’d closed his eyes for a moment but they were open again and were focused on Kalyn.

  Kalyn scooped some of the cum off her breasts and sucked on it.

  “It tastes good,” she said. She pulled his cock to her face and licked the leaking bits of cum off his cock. She licked off all the remaining cum off his dick and then scooped up what he’d ejaculated onto her body.

  She ran her tongue around her lips and smiled. Gary collapsed next to her on the bed.

  “That was amazing,” Gary said.

  Kalyn’s smile widened. She hadn’t had an orgasm as power as that in a long time. She liked the way that he had made her feel. His cock was large and powerful and he’d cum all over her. She turned onto her side and stroked his body tenderly, quietly looking at the way his muscles contoured.

  “I liked it too,” she said. Gary leaned in and kissed her. He pushed his tongue against hers and Kalyn closed her eyes. She could feel herself warming up again. She pressed her body against Gary’s. His dick was beginning to harden again.

  “I think you liked it a lot,” Kalyn said. She took his dick in her hand and put it on her clitoris. She used it to draw lazy large circles around her swollen button.

  “That feels good,” Gary said.

  “You say that about everything,” Kalyn said continuing to masturbate herself with his hard dick.

  “That’s because everything feels good.”

  “Hmmm….” Kalyn said. She could feel the tide of pleasure coming in again. Her mouth opened wide and she shook in Gary’s arms as she orgasmed once more. He took his dick in his hand and continued to use his head to circle her clitoris. Kalyn went rigid for a moment and then shook uncontrollably.

  “Fuck, fuck, fuck,” she screamed.

  Gary took that as a cue and pushed his penis into her. She was still wet inside. He pushed his hips forward and back. He could feel his penis ache as cum started to build up in his testicles.

  “I’m going to cum, I’m going to cum,” he said.

  “Cum in me.”

  Gary pushed forward once more and exploded inside of Kalyn. He kept his softening dick in her for several minutes as his warm liquid filled her.

  Eventually he got up and went into the bathroom. He came back with a towel and softly wiped up the cum deposited inside of Kalyn.

  “I’m on the pill,” Kalyn said.

  “Good. I sort of thought so but I wasn’t sure. I figured when you said, ‘cum in me,’ that meant you didn’t want to get pregnant.”

  “Well not yet at least.”

  “We can keep trying though” Gary said.

  “I like that idea,” Kalyn replied. Kalyn slipped off her heels and then she she pulled the covers of the bed up and slipped underneath them. “This room is beautiful. The sheets are like silk.”

  “Money can get you a lot of luxury.”

  “I think I might be able to get used to it.”

  “I like that attitude,” Gary said. He pulled the covers up and slid in next to Kalyn. He pulled her to him. She had a strong scent that was mixed with their sex. Soon Gary was asleep. Kalyn could hear his light breathing turn heavy as he fell into a heavy sleep. Kalyn stayed up watching him sleep for several minutes.

  She ran her fingers through his hair and then down his face. He had some light stubble on his face. It was soft. Her finger ran down his neck and then arm. Her touch drifted down to his right hand. She touched the back of his palm and then intertwined her hand with his. She squeezed it lightly. There was no reply. She lifted her hand and ran her fingers again on the back of his hand. She followed the line of each finger, the index, the middle and then the ring. When she came to the ring finger she felt the indentation of the wedding ring but Gary wasn’t wearing it. He must have taken it off at some point. A wave of guilt ran through Kalyn. Even though she was conflicted about having an affair it didn’t feel good knowing about it. The words of Mel, of Grace, and of Gary ran through her head.

  “So, what? Plenty of people are married. Plenty of people are divorced. Plenty of people are single. Sometimes married people don’t get laid. Sometimes divorced people don’t. Sometimes single people don’t and everyone needs to get laid. Maybe Joy doesn’t like to play on his team anymore,”

  “I’m not really sure what Joy is doing to be honest. She does her own thing.”

  “I’ve been so anxious lately. My husband and I aren’t doing to well. I am considering having an affair. He just isn’t giving me what I want physically.”

  “Don’t be so moral. One it’s boring and two marriage is a terrible institution.”

  No matter what Kalyn was thinking now she was thinking it was all wrong. She’d been impulsive about hitting up Gary.
She hadn’t even needed to meet up her friend. It was a lie. She’d come into the city hoping to see him. She’d left the salon feeling a little better about things and that had turned into feelings of romantic longing. Now Gary was asleep beside her and she didn’t know if that was what she really wanted.

  His breathing stayed the same but he twitched lightly, kicking out his leg as if he was running. Kalyn pulled out of his embrace and he rolled onto his back without waking. Kalyn got out of the bed and walked to the living room. She could still see the San Francisco skyline. It had gone nowhere. The lights were all the same. The ocean was still there, gently lapping against the bay. She stood there for a moment in the room. She found her heels beside the bed. Gary was still in dreamland. She would leave him there. She found her bra and dress along with her panties. They were still wet from her desire. She put them back on and walked out the door letting the apartment door shut quietly.

  She didn’t want to be a mistress. She didn’t want to be a side piece or some disposable object. She wanted something real, and meaningful. Being a mistress and having an affair wasn’t what she wanted. She looked down at her phone and hailed an Uber. While she waited for her ride she walked into the Redwood bar. The bar was closing up but the slap of wood that made the bar was still there. Still solid and still unmoving unlike Kalyn’s feelings.

  Chapter 10

  “Hey Kaboose,” Kalyn said.

  He’d been waiting for her as normal at the door. He looked happy to see her when she walked in but after her shower and after she’d prepared for bed he didn’t go up and lick her face as normal. Instead he did his usual figure eight at the end of the bed and plopped down to sleep.

  “What’s the matter Kaboose,” Kalyn said. “Is it something that I did?”

  He ignored her voice. Kalyn knew her dog wasn’t asleep and that he instead was just lying there quietly. She didn’t know what had caused him to change but she didn’t like it. Maybe it was her. She laid her head down and fell into sleep.

  Kalyn wasn’t a vivid dreamer but her dreams that night were alive. Joy was in front of her. Her breasts were full and flush and pointing at her like rockets. She’d grown a tail and sprouted wings. Joy flapped her wings in front of Kalyn and begin to float over her. A pitchfork appeared in her hand and she began to prod Kalyn.