This is my first attempt on this site. Please let me know what you think. Any honest feedback is appreciated.
-Serena_Dare
***
Every time Brooke opened her eyes she'd see her Uber driver trying to catch a look at her in his review mirror. She didn't want to give him the satisfaction of knowing she kind of liked it, so she didn't let her pride reach and upturn her lips. She closed her eyes again and went over her routine in her head.
Right when she gets there, she'd go straight to the hotel lobby's bathroom and check her outfit, makeup, and teeth in the mirror, spit out her gum, and then head over to the hotel bar. Mark, her nervous and hopeful, prospective sugar daddy should be waiting there. This would be the first time they met in person so she'd asked Sarah to plan on calling her a half hour into the date, just in case he turned out to be a creep and she needed an excuse to get away. If Mark seemed nice Brooke could just text Sarah to tell her not to call, then she'd ask Mark what he felt like doing that night, and let him take charge from there. It wasn't Brooke's first time doing this. She'd paid for nearly four years of her undergrad by following her routine. The problem was she liked to spend as fast as she earned, so she had no savings for grad school, but she knew she had no reason to worry. It wasn't hard for her to find willing sugar daddies like Mark. The two other daddies she saw at the moment kept her very comfortable. Add a third and what was left of her tuition would be paid for in just a few weeks.
Her Uber pulled up next to the valet station of the towering downtown Chicago hotel. Brooke had suggested the place. She liked running up a big bill, at least for the first date. A young man in a red vest opened her car door for her, she said thank you to her driver and stepped out towards the hotel. The same valet opened the lobby door for her. Brooke said thank you again and walked inside to head toward the ladies room, spitting her gum into the gilded trash can next to it.
She looked herself over in the mirror, ignoring the other women and their looks of jealously. She knew what they saw; her in her tight strapless black dress that followed her curves perfectly, the left side ending just a little higher on her leg than the right but both above her knees, her brunette hair shining and spilling over one of her shoulders and her lightly tanned skin giving her just a tiny hint of an exotic look. At 5'6" plus her 4 inch black heels she bent towards the mirror to reapply her rouge red lipstick; the effect of the added lipstick created lips begging to be kissed. Finally looking into her deep brown eyes, Brooke took a deep breathe, and began walking over to the bar.
She readied the smile she used for all of her daddies; one that offered excitement and happiness at finally meeting the incredible man she'd be talking to for so long. She saw a dark haired man sitting alone who looked like Mark from the pictures he'd sent her. He was looking down at his half drunk glass, spinning it nervously.
Brooke had met him through an online sugar baby/sugar daddy site. He'd messaged her telling her he'd been looking for a younger girl he could spend some time with, admitting that he was married, but that neither him or his wife really cared for the the other anymore. Brooke had looked through his profile a little and he seemed alright for what she was after. Early fifties, good paying job, okay looking. She gave him her number and they'd texted for a week, setting up a day they could both meet, and Brooke had gently made sure he knew her expectations. He seemed sweet, and just needed some company. Brooke was happy to give it to him.
Mark must have heard Brooke's heels click lightly against the floor as she drew closer, drawing his attention away from his spinning cocktail. Both his mouth and eyes wide at the sight of her, her stunning smile shining, and her perfect body swaying. Mark stared just long enough to become embarrassed about it, turning his beige face a light pink, trying not to think about the blood rushing to his growing member. In an effort to recover, Mark jumped up out of his chair to shyly greet his nearing date.
Brooke quickly looked him over. He was dressed like he'd come from work. Black suite, blue shirt with no tie. A little pudgy but not fat. His black hair with gray streaks through it. The blue eyes behind his glasses timid, not quite meeting her eyes.
"Hey! Mark?" Brooke started brightly, making her smile even bigger.
"Yeah! Yep that's me!" Mark answered, smiling through his nerves.
Brooke, seeing him try to work out whether he should offer her a handshake or give her a more familiar hug, took the initiative and moved up against him, putting her arms under his for a hug and kissing him on the cheek. She purposely brushed against his pants with her leg and felt his cock jump a little at her kiss.
He went from light pink to bright red as Brooke pulled back and he said with a little more confidence and a smile that wasn't so forced,
"Please, sit down." And he said gesturing to the booth he'd gotten for them. "I already ordered your drink. You said you like manhattans right? I hope that's okay." He said sitting back down across from her.
"That's perfect," Brooke answered warmly. She squeezed his hand a little, and said, "You're so sweet to remember that!" Brooke could already tell she was totally safe with Mark, so she pulled her phone from her clutch, to text Sarah not to call.
Mark was smiling a little easier back at her and stroking her hand slightly with his thumb. Brooke could tell he was trying not to look at her 36c breasts in her push up bra, but he was losing the fight, so she made it easy for him.
Leaning forward slightly, so that he could look down her dress, Brooke rubbed her leg against his, pretending she didn't even notice what she was doing and said, "God I'm so glad I'm finally getting to meet you!"
Mark, giving in to the little show she'd offered him, looked down her dress, took a big sip of his drink, laughed nervously and said, "Not even close to as happy as I am! God Brooke, you look so beautiful!" Although saying it caused his face to go bright red again. "I hope you don't mind me saying that," he added quickly.
Brooke had known walking in, Mark was going to be kind of a nerd, but she didn't mind. She even thought it was kind of cute. Brooke pushed against his nervousness a little harder, and nuzzled his leg with hers some more, certain that by now that he had a bulge growing.
"Haha thank you!" She said. "I can already tell I'm going to really like you! Let's have some fun! When the last time you did a shot?"
Brooke ordered a shot of tequila for each of them, then another, and then one more after that. After their third, Brooke had moved over to Mark's side of the booth to get closer to him. She'd been carrying the conversation for most of the night but finally Mark was starting to open up, and was becoming a little more daring with his eyes.
Raising his lusting gaze from Brooke's chest, over her neck, and past her lips, to her eyes, his arm around her, Mark leaned in and said, "Do you have any idea have gorgeous you look tonight Brooke? I've never wanted anything so badly."
Brooke laughed lightly, looking down and laying her hand high on the outside of Mark's leg, then sliding it towards his inner thigh and over his clear, straining bulge. Raising her head so that her lips just barely brushed Mark's ear, Brooke whispered in her most sultry voice,
"Have you gotten a room yet, Daddy?"
***
In the elevator Brooke could tell from his stare that he wanted to start kissing her. She leaned against him, inviting him to put his arm around her as they rode up. Even with Brooke in her heels, Mark still had about 4 inches on her. Looking up at him, her best imitation of young innocence in her eyes, Brooke reached around him, deep into Mark's pants pocket, opposite her, and took out his room key. She'd seen on the check at the bar which room number he'd billed it to, so when the doors opened, she turned and walked backwards in front of him taking his hand, looking up through his fogged over glasses, into his eyes, then down to his clear bulge, Brooke ran her tongue lightly over her lips. Turning, she guided him down the hallway to his room. Brooke stopped outside their room, and slid the car into the lock. She felt Mark, breathing heavily behind her, and gently pushing against her, his hands on her hips. Brooke could feel his rock hard cock fighting against his pants and pressing into her back. She opened the door and stepped inside.
Mark pushed in a little harder, forcing Brooke forward. Clearly starving for her, Mark tightened his grip around Brooke's waist, and used it to quickly turn her around, pressing her back up against the wall. Closing the door behind them, Mark dropped one hand behind Brooke so that he could start groping her firm ass through her taut dress. With his other hand, Mark gently held Brooke's neck back against the wall. Pushing the rigid cock in his pants against her, Mark gave sighs between each long kiss he pressed against her, proving his desperation to be with her. The hand he had on her neck reaching behind Brooke toward her dress's zipper.
"Daddy... Daddy wait.," Brooke managed to say, breathlessly, between his over-eager lips. Pushing him back slightly, holding his gaze and keeping a playful tone she said "Remember what we talked about? Before all the fun stuff..."
"Oh yeah! Yeah, of course," Mark said apologetically. "I'm sorry. Guess I got excited. Been a while for me. Sorry,". He bounced over to the nightstand and pulled an envelope out of the top drawer, handing it to Brooke. "First month of, what I hope is, many allowances." He said in a way that sounded like he had practiced saying that for her, then smiling and sitting down on the queen size bed next to them.
Brooke walked over to a little table in the corner of the room, opening the envelope and brushing through the numbered bills inside quickly. She felt a little bad stopping him the way she did, but she knew how to make it up to him.
Brooke turned around to face Mark, staring into his eyes and then reaching back her unzip her dress, watching Mark follow it, as it fell to the floor. His eyes slowly started to trace back up Brooke's legs and body, savoring every inch. She was left standing there, nearly naked apart from her favorite pair of black lace lingerie. Her stomach, toned and tanned, Brooke, heels still on, stepped over her dress with her long legs and stood in front of Mark, seated on the bed staring at her, mouth open, and Brooke's hands on his thighs.
"Oh my go-," he started before Brooke cut him off, kissing him hard, letting their tongues play, and allowing Mark to run his hands across her mostly bare body, before finally dropping to her knees in front of him.
"Do you want me, Daddy?" Brooke asked looking up at her newest patron with her deep brown eyes, and watching him nod breathlessly, as she put her hair in a ponytail using the tie from her wrist. "Say the words, Daddy. I wanna hear them."
