Divorcee and Debutante

Author's Note: I was hoping to release these weekly but didn't realize there could be long delays on publishing.

All characters are over 18 years old.

***

Garret got another text from Sarah late on Thursday evening. All it said was, "I don't have to work this Saturday"

He knew that the guys would tell him to ignore her. It was definitely still a low-effort text, and he was still annoyed with her, but after four days had passed he was mostly over it. He debated what to do for several minutes, but ultimately decided to give it another shot. They had liked each other well enough, and he didn't want her to be a one-night stand. If the modern hook-up culture was bad, and the younger guys insisted that it was, then he would 'be the change he wanted to see in the world'. Right?

So he texted back, bantering with her for a bit before setting up a real date. She wasn't as enthusiastic about it as he had hoped for, mostly keeping her practiced attitude of cool indifference, but was still somewhat positive. He was going to pick her up at her place, take them to dinner somewhere nice, then they'd get drinks, and he assumed that after that they'd be coming back to his place. He told her to wear a dress, preferably black, under her coat for the evening, and she said she had something she thought he would like. It was going to be a nice, classic date for a gentleman and the lady he was interested in, Garret thought.

***

He arrived at her apartment the next evening, just a few minutes late. Sarah had said that she had two female roommates, and the area they lived in was fairly decent. On the night he met her he had learned that she was an office worker at some sort of logistics company. She obviously wasn't that interested in her work so he had stopped asking her about it quickly and moved on.

One of Sarah's roommates let him in when he knocked and let him know that Sarah was still getting ready. The girl was reasonably pretty but Garret consciously decided not to try to hit on her and just sat down and reviewed some documents on his phone instead while he waited. He knew that the guys would tell him this was a mistake. After all, if he made some mild moves on Sarah's roommate, that would communicate that she wasn't that special or valuable to him, which would give him more power in the relationship. But wouldn't it also make her more likely to not care about him? Wasn't this whole power struggle concept just a recipe for permanent mutual dissatisfaction?

Sarah didn't come out of her room for more than a half-hour, and Garret groaned inwardly as he imagined what the guys would say was really going on. But he had a choice: He could interpret this as a subtle power-play, showing him that he was barely worthy of her time and he would only get to see her on the schedule she chose. Or, he could view it as a woman who was nearly two decades younger than him who wasn't great with time-management. He determinedly decided that he would choose the second option.

Sarah finally came out and greeted him with a quick kiss before they left to try to make it to their reservation on time. She had followed his instructions at least, wearing a tight black dress that was both low-cut and short enough to get some attention. She also wore tall black heels, black thigh-highs, and had done up her hair and makeup nicely. She had a knee-length, wool, red trench-coat that she wrapped around herself before they went out into the cold.

Her light brown eyes were highlighted again with dark eyeliner and extensions on her lashes, and her full red lips reminded him of how she had looked, bound and naked on his floor, as she obediently sucked on his cock. He felt a pulse of arousal through his body at the memory and told himself that he had made a good decision to see her again.

***

Garret played the gentleman role as he took her out to dinner at a nice restaurant he had gone to with clients but never with Ashley. It would have felt too strange to go somewhere he had been with his ex-wife while the wound of the divorce was still so fresh. They made it just in time before his reservation expired and sat down across from each other at the small table.

They had made a little small-talk on the ride over, chatting a little about their favorite places to eat in town, although Sarah had also been on her phone and texting the entire time and wasn't as responsive as he had hoped. Garret ignored it, assuming she was just letting her friends know where they were going.

"So what's your next big travel destination," he asked once they were seated. Sarah had talked extensively about her travels on the night they had met and he thought this might be a way to get her involved again.

"Oh, yeah, some friends are going to Spain next summer and we're going to have an amazing time on Ibiza," she replied, looking up from her phone with a smile. She looked back down and swiped on it for a few seconds before holding it up to him.

"These are some of my best friends," she said, showing him a picture. "This is our trip to the Bahamas last year, which was soooo amazing."

The image showed a mix of young men and women smiling on a boat. He recognized Sarah lounging against the railing, her head leaning on the chest of an attractive young man who had his arm around her in a way that was clearly more than friendly. The bikini she wore was about as revealing as it could possibly be, and the man's hand was clearly cupping her bare ass cheek.

Garret raised his eyebrows slightly and said, "Looks like a fun time," in as non-committal of a tone as he could muster. He struggled to avoid viewing this as a power-play by her, showing off that she had plenty of other male suitors to make him jealous and more prone to chasing after her. He told himself that she was just showing what she thought was a nice picture from her last trip.

"So just Ibiza, or just Spain, or more of the Mediterranean?"

"Ibiza and Madrid," she replied, taking her phone back and swiping on it some more as she looked down at it. He expected more of a reply, or for her to show another picture or something, but nothing came. After a few more seconds she giggled and clearly started typing something.

***

The rest of their date together was basically more of the same. Sarah didn't outright ignore him, but she was on her phone more often than not and her answers were typically short. Once dinner was over and they moved to the bar to have a drink she was a little more attentive, but still showed little interest. She did ask him about his company once, but she obviously stopped paying attention almost immediately when he started to describe what he did, even though he tried hard to make it sound as interesting as possible.

When Sarah excused herself to go to the bathroom, Garret texted the guys in frustration and told them what was happening. He mainly got laughing responses back from them and "I told you so." Sean gave the only serious answer, telling him that the only way to salvage the situation was to move the date back to his place ASAP and fuck her, and Garret couldn't really think of a better option.

He looked up from his phone and saw that, while Sarah was coming back from the restroom, she had obviously run into another man she knew. She was talking with him and laughing, putting her hand on his arm, and then she glanced over at Garret to confirm that he had seen her. She talked with the man another few minutes to be sure she got her point across before she walked back and joined Garret at the bar.

He maintained a cool and calm exterior, but inside he was livid. It wasn't that Sarah was interested in other men. He knew that he had no claim of exclusivity on her after their single night together. And it wasn't that her lack of attention was insulting to him, because he could easily write that off as immaturity and a short attention span. It was that he now believed that it was all deliberate, part of a game designed to make her feel she had power and that he had none.

The worst part was that he knew that Sarah wouldn't actually be happy in a relationship with a weak man, so if she 'won' this power struggle it would inevitably mean the end. Women don't actually want a man who worships their feet and lets them get away with murder, because they can't respect that sort of man. There was no way to date a woman like this without playing, and somehow winning, the game of power. And according to the younger guys, all the women they had met so far were all playing exactly that same game.

Garret sipped his drink and chatted about nothing with her for a couple more minutes while he decided what he wanted to do. He could tell her it was over, end the date, leave her there or take her home, and he could feel good about himself that he had made some sort of statement. Or, he could continue to suffer and ignore her disrespect until he could get her back to his place. Or... maybe the third option could work?

"You know, I've got to be honest with you," he said suddenly, putting his hand on her knee somewhat abruptly as they sat next to each other at the bar. Sarah looked directly at him with slight surprise at the change in direction and tone.

"I thought I wanted to go on a real, serious date," he continued, "and this has been fun. Sometimes I like an excuse to dress a little nicer and enjoy the finer things. But honestly, at this point I'm kind of bored with a serious date and I think I really just want to fuck you instead."

"You just want to fuck me?" Sarah repeated, raising her eyebrows in surprise.

"Yeah, like, as soon as possible," he answered, nodding seriously and looking into her eyes. He thought this move might have a fifty percent chance of working. She would either be offended and end the date, which would be fine, or she'd come back to his place. He stood up and took her hand as if to lead her away from the bar, hoping to force the issue before she thought too much about it.

"Um, okay," she said, standing up and grabbing her coat before following him. He moved them quickly through the restaurant, looking back at her with a wink and a cheeky grin. She smiled in response, obviously warming up to his impatience and brazenness, and the idea of getting laid sooner rather than later.

He pulled her to his side as they walked towards his car, running a hand from her shoulder down her arm to her hip, and holding it possessively through her coat.

"You did a good job picking out a dress I'd like and making yourself pretty," he said to her quietly as they walked. "Are you going to be my good obedient girl for the rest of tonight too?"

Sarah leaned into his touch, enjoying this dominant sexual side of him much more than the dinner date and all the boring talking. She pouted up at him as they walked and nodded her head.

"Yes daddy, I'm going to be so good for you tonight," she said, reverting back to what was clearly her favorite term for him when it came to sex. The more Garret thought about it, he really wasn't a huge fan of the term since it reminded him of his own age and the fact that she was so much younger than him, but he decided to go with it again as well a he could. It clearly turned her on, at least.

Once they got in the car it was much better than the drive to the restaurant had been. With sex on the mind, Sarah was much more interested and submissive, and he ran his hand along her thigh and talked about how much he'd been looking forward to getting her alone. She responded by attempting to rub his dick through his pants and then started to unzip them, but he gently pushed her hands away.

"You have to wait for that, baby," he said, smiling as she pouted at him from the passenger seat. "But I have something else for you to do on the drive. Pull your dress up and rub your little pussy for me. Seeing you touch yourself turns me on so much."

Sarah smiled and shrugged out of her trench coat before obediently hiking up the black dress and sliding her black lacy thong panties to the side. She was already a bit turned on even though things had accelerated very quickly in the last ten minutes, but being told what to do by a dominant man had always gotten her going fast. She sucked in a breath quickly when her fingers found her clit and started to circle it. It was somewhat embarrassing to be told to masturbate in a fairly public way for his entertainment, but even that added to her arousal.

"That's perfect," he said, glancing over at her as he drove but mostly keeping his eyes on the road. "Don't stop rubbing your clit until I tell you to, but you are not allowed to cum until I say so!"

"Ungh, yes daddy, when are you going to let me cum daddy," she gasped, already rapidly climbing towards her orgasm.

"Slow down, way down," he said sternly as he noticed the rapid pace she was setting. "You can't cum until my cock is all the way inside you, so get that tight little pussy nice and wet for me."

Sarah groaned, but complied and slowed down to a pace that she thought she could keep edging herself at for the ten minutes it would take them to get to his apartment. While on the way, she occasionally begged him to let her cum early, but he always denied it.

By the time he parked the car in the garage for his building, Sarah was soaking wet and groaning with frustration. Garret moved around to her side of the car while she readjusted her panties and the bottom of her dress and he opened the door for her. When she lifted her hand to take his as she got out of the car, he held it up to stop her instead.

"Wait, don't get out yet," he said, moving his hand so that the palm was facing upwards. "You need to give me those panties before you can get out of the car."

"Yes daddy," she giggled in reply, sliding her hands up her thighs and hooking her thumbs under the band of the tiny garment. She lifted her hips and slid them down to her ankles before stepping out of them smoothly, in a move that Garret was absolutely sure she had done multiple times before. She placed the panties in his hand and he examined the damp garment for a brief moment before putting it into his pants pocket and reaching out to take her hand.

After she was out of the car he trapped her against it with his body and kissed her forcefully. Sarah moaned, desperate to move out of the extended foreplay and on to sex, but he seemed intent on taking his time. He grabbed her coat at one of her wrists and began to pull up, like he was going to take it off of her in the frigid parking garage, and she pulled away from the kiss in confusion.

"You forgot something important," he whispered to her as he leaned in towards her ear and then kissed her neck.

"What did I forget, daddy?" she asked breathlessly.

"I didn't tell you to stop rubbing your clit, did I?" he replied, helping her slide her arm out of the coat sleeve and then wrapping the coat shut with her arm trapped inside.

"Rub it nice and fast now to make up for the time when you were disobeying me," he said darkly, before starting to kiss her neck again as she moaned. She pulled up the hem of the dress, under the privacy of her coat, and moved her hand back to her love button to start doing as he commanded, wondering how much longer he was going to make her keep edging herself.

After he could tell that she was doing as he commanded, Garret took her by the free hand and led her towards his place. He walked slowly, enjoying the look of growing desperation on her face and the apparent difficulty she had walking steadily in her high heels while distracted, but before long they were walking through his door and into the big open living and dining area of his apartment.

"Stand still right there," he commanded after getting both of their coats off. Sarah complied, blushing slightly as he watched her while she still rubbed her clit under the hem of her dress. She had slowed down again because there was no way she would be able to hold back the inevitable much longer at the quick pace she had been setting earlier. After a few moments he slowly undid his belt, never taking his eyes off of her, and then led her by the arm to the edge of his solid oak kitchen table. Sarah struggled to keep rubbing as he bent her over the table, pinning her hand between her legs, and then she heard his belt unzipping and what she suspected was a condom being opened.

Before long, she felt his hands pushing up her dress and then appreciatively squeezing her ass before tracing the outline of the vaguely floral tattoo on her lower back. He slowly worked his way towards her pussy while she continued to stroke herself, letting out little moans when he touched something sensitive.

Finally, she felt him using one hand to spread her pussy lips open and then felt two fingers of his other hand slip inside to start to stroke her G-spot.

"Oh my god, oh fuck, daddy I need to cum right now!" she squealed, overwhelmed by so much stimulation after all the edging. He pulled his hand back out and immediately spanked her ass hard several times, making her gasp in surprise.

"No! You will not cum until you have permission! Have I made myself clear?"

"Yes daddy, please go inside me and make me cum!"

"Stop rubbing yourself now," he commanded instead, making her let out a small sob of frustration as he pulled her wrist away. He then pushed her up onto the table and flipped her over onto her back. He guided her to lift her back off the table and then slid her dress up to her chest, before lifting her shoulders so he could take it off completely. Sarah laid back on the table, completely naked except for her thigh highs and heels, and licked her lips in anticipation as he removed his shirt.

Garret lined up his cock with her smooth and slick entrance, teasing her briefly with the tip before he started to push inside. She was incredibly wet and he bottomed out easily, both of them groaning in satisfaction.

He grabbed her wrists again, pinning them on her chest with one hand and groping her breasts roughly with the other. He then slowly started to saw back and forth, enjoying the tight friction of her inner walls while she moaned incoherently and bucked to try to get more stimulation. He took pity on her after another minute and reached down with his free hand to gently stroke her pleasure center.

"Oh god oh god oh god, I'm almost there!" she screamed, as he steadily increased the speed of his thrusts.

"Look at me," he commanded forcefully when she closed her eyes. He stopped rubbing her clit and instead reached up to grab the back of her head and hair to pull her up off the table. She opened her eyes and stared into the intense expression on his face. Without his fingers on her clit it was going to take her a little longer, but she knew that with his pelvis grinding against her nub and his cock deep inside her pussy it wouldn't be very long at all.

"Keep your eyes open and on me when you cum, and say my name," he said, as he sped up even more.

"Yes daddy, oh please Garret, I'm so close," she replied, her face showing the tension as she neared the edge of an orgasm once again. He felt her lower body start to spasm and shake, and then her eyes opened very wide before rolling back in her head as she finally came. He relished knowing that the last thing she had seen before she went over the edge was him standing over and fucking her.

"Ungh! Fuck! Oh Garret, oh fuck, please daddy," she said incoherently as he continued to pound her. He took her as hard as he could, letting out his frustration and anger with her from earlier in the night with an all-out pounding of her wet snatch until he finally came with a roar.

Garret panted, catching his breath as he laid his date back down on the kitchen table and pulled himself out of her. He took the condom off and tossed it in a trash can before picking Sarah up and carrying her into his bedroom, still mostly wearing his suit-pants. She snuggled up to his bare chest while he held her in his arms and he enjoyed the fresh smell of her hair as he laid her down on the bed. He maneuvered so that he was mostly sitting up on the bed with his back against the headboard, and then moved Sarah's head to lean on his chest again. She mumbled happily and ran her fingers through his chest hair slowly.