Nicole lay naked on an unfamiliar bed, next to a similarly nude older man she had met only today, vigorously tugging on his semi-erect penis. They were already significantly over the one hour mark, and Nicole was hoping this would end soon. Numerous breaks to catch his breath and waiting for his pills to kick in had added up. He wasn't unattractive, but her hand was cramping and this was, after all, a job. One of the less glamorous aspects of her newfound career.
"I'm sorry, dear," the man apologized. "Those blue pills just haven't fully kicked in yet."
She paused for a moment to reassure him. "Don't worry about it. Would you prefer it if we tried again another day?"
"I think we're getting there... maybe you could try again with those gorgeous lips of yours?" He caressed her face, running his calloused fingers along the side of her cheek before pressing his thumb onto her lower lip. Nicole responded by sucking his thumb, which was more satisfying than his cock at the moment. Her client seemed to like it, so she continued for a while before switching to his index finger.
"There we go, there we go," he repeated as his cock started to swell again. Those pills must have kicked in finally. Nothing to write home about, but Nicole could at least do something with it. She popped his finger out of his mouth and replaced it with his dick. In just two minutes he went from limp to on the verge of orgasm.
"Yes, yes!" he moaned, his hand groped at her naked body, and Nicole could feel him smearing her saliva all over her ass and thigh with his thumb. "Look out, dear... I'm close now..."
Nicole sped up slightly as she awaited his load, but it never seemed to come. Another minute passed and he fell silent. Nicole was getting frustrated.
Coming up for air and a jaw break, she resumed stroking him. "You were so close, what I can I do to bring you over the edge?"
Her client looked her in the eyes. "Beg me for it. Tell me you want it. Say my name."
Nicole's stomach sank. Was it Victor? Kevin? The classic John? She really had no idea what this dude's name was. Fuck enough old men in a week and they all sort of blend together.
"Give me your cum... I want your cum," Nicole pleaded with him as she gave him a handjob. She punctuated each statement by popping him in and out of her mouth a few times. "Please... I want your cum. I need it!"
It seemed to be helping, as he returned to the brink once more. "Yes! Almost... almost..."
More time passed and her hand cramped again. In a last ditch effort she decided to play one card that she generally avoided unless specially requested. "Daddy!" she yelled. "Give me your cum, Daddy!"
His warm load finally flooded her mouth just as she took it back between her lips, the salty taste of a hard fought victory oozing over her tongue. Once he was finished, she managed to avoid spilling anything on him or the comforter and dashed for the bathroom. There's no way she was going to swallow for this guy after she already gave him so much extra time.
--
Nicole checked the time on her phone. "Shit, I'm definitely going to be late." She had been texting with Anthony for a few weeks, mostly catching up and gossiping about people from school, and they had traded some late night risque photos. After numerous hints from Nicole, he finally asked her to join him at the end of his shift for the closest thing to a date she's had since Mikey. Yet again, he had her at "free drinks".
After a few swigs of mouthwash, a quick wipe down, and re-doing her makeup, she bolted for the door. She almost forgot to check in with Emily on her way out for her pay.
"Aren't you forgetting something?" Emily called out as Nicole stepped out the door. She ran back and grabbed the envelope from her boss, looking away and blushing as she grabbed the evening's take. "Big plans?"
"Yep, uh, just meeting up with some friends for dinner! Bye!" Nicole didn't bother with small talk and instead darted back for the door. Things between them had been awkward ever since their threesome with a client a few weeks back. Emily had acted like nothing ever happened, but it was a big deal to Nicole, and she was a little hurt by Emily's complete lack of reaction. Despite this, she had seen Emily watching her twice now while Nicole pleasured clients.
--
Nicole traded the keys to her beater car to the valet for a ticket and speedwalked inside trying to make up time. The normally frugal girl decided to splurge on a valet to save the five minute walk from street parking. She stopped right outside the door to put her heels on while leaning against the glass window. Inside the lobby bar, there were only a few patrons, mostly older folks sitting alone. She spied Anthony in the back and went over to him, wobbling unsteadily in her heels.
"I'm so sorry I'm late," she apologized. "Got held up at work. Don't ask."
Anthony stood up and hugged her hello. "Don't worry about it. My shift's over, but I made you a double." He gestured towards the drink at the table.
Nicole slid into the booth and was surprised when Anthony scooted in next to her rather than across. "So, how was work..." Nicole asked in a sing-songy tone as she sipped the whiskey and diet coke. It tasted more like a triple.
"Slow. Real slow. None of the regular tippers showed today. Just the, uh, you know. Ladies."
"Ladies?" Nicole raised an eyebrow.
"The hookers." Anthony said.
"Oh," Nicole said, raising her eyebrows. "I didn't know."
"Really? I thought you said that you..." Anthony cleared his throat and abandoned his sentence. "Nevermind."
"So this is where the classy ones hang out? Good to know." She took another deep pull on her drink.
"I mean, there's an arrangement with my boss. He runs the bar, makes sure no one bugs the women. They give him a kickback. We kick out anyone they want us to kick out. Unfortunately they think that means they don't have to tip the bartenders."
"That sucks." Nicole stared at him while she sipped from the cocktail straw.
"I told you I've seen your boss in here, right?" Anthony said as he stared at the empty glass in his hand.
"Does she tip?"
Anthony laughed. "I've only seen her on the weekends when I barback, so I don't really know. Is she keeping you safe? It's a rough profession. I've seen things go bad before."
Nicole nodded. "So far no trouble. She has a whole system. Most of them are..." Nicole stopped herself before she said anything else. "Do you really want to hear about this?"
Anthony shrugged. "No judgment. I just want to make sure you're safe."
Nicole smiled, putting her hand on his knee in his black work pants. "You're sweet." She was already feeling tipsy, and not even halfway done with her boozy drink.
--
Once they had broken the ice and started talking about subjects other than the world's oldest profession, Nicole loosened up and started enjoying herself. She forgot how funny he was. It was always fun to reminisce about teachers they shared, and gossiping about who got knocked up. After a lull in the conversation, she reached into her purse, fished out a bill from tonight's pay, and slid it in front of Anthony.
"What's this for?" he asked.
"You know, twenty. I can't give you a ride, though." Nicole smiled. "Your fault. I was overserved."
"How the tables have turned," Anthony said, chuckling. The reference to their high school days of Nicole getting a ride and twenty bucks for a blowjob did not go unnoticed. He balled up the bill and shoved it into his pocket. He looked around for a minute and grabbed her hand, helping her out of her seat. Her short dress gave anyone who was paying attention a brief flash of her panties as she stumbled out of the booth. "Shall we head out?"
"I guess," she said. "Do you have a roommate?"
"Yeah, um, roommates. Sorry. Do you live alone?" Anthony asked right back.
"No, I live with Jamie, remember? She's probably there with her boyfriend."
"Oh yeah. Shoot." The pair leaned closer and closer together as they spoke in hushed tones. "I can find us an empty room again..."
"Maybe one with clean sheets this time?" Nicole scrunched her face up as she thought about the last room he brought her into.
"Let me see what I can do, I saw my boss a few minutes ago. Hold up." Anthony walked over to the bar and spoke to the guy at the register. As they talked, Anthony's boss stared at her and gave her a quick smirk and a nod. Nicole shifted her eyes and blushed. He kept staring and beckoned her over to the bar.
Anthony introduced the two. "X, this is Nicole. Nicole, this is my boss Xavier." Xavier was much taller than Anthony, and had a meticulously maintained hairline and thin goatee. Surprising Nicole, Xavier didn't seem much older than Anthony.
"Pleasure to meet you Nicole, how are you doing tonight?" he asked with the cadence of someone trying overly hard to hit on her.
Nicole gave a polite smile and a quick "Hi, I'm fine."
"So you guys want a room for a little privacy, huh?" he smiled.
Nicole blushed further. Anthony gave his boss a gentle smack on the arm. "C'mon now, don't scare her off, X."
"No it's cool, I got you, I got you." he said with a big smile. He started to poke at the register's touch screen. "Just a little jealous, I guess. Been a minute since I've had a date with someone as 'fine' as this one. You gotta share your secret, T."
