Jake 02: Career Move

It was early Friday evening, and Rosemary's bar was as busy as one might expect. Jake was seated at a small table in the middle of the bar, fingering the label on his beer bottle. His second drink of the night. He had dressed smartly for the occasion, wearing a black button-up shirt that matched his curly hair, well-fitting jeans that hugged his sculpted legs tightly, and a pair of dark brown leather loafers. Those were his nicest shoes. He made sure to avoid wearing them in any situation that risked getting them dirty. They were not work shoes, for sure. Then why did he feel as if he was enduring a job interview?

In front of him was a petite woman. She had stood barely up to Jake's shoulders, in her slick black ankle strap pumps, when they had met barely half an hour ago. It felt much longer. This woman certainly knew how to dress smartly. She wore a deep blue pant suit, consisting of a blazer that almost shone in the dim lighting of the bar with its gold trimmed buttons, and matching slim fit leggings. Her light brown hair was tied up in a pony tail that stretched down to the middle of her back. Behind her thick rimmed designer glasses were a pair of stern eyes that shifted between light brown and hazel in depending on the light. They were currently fixed on Jake with a piercing gaze.

Her name was Giselle. Jake had messaged her on a dating app. She had been very forward about her dislike for those kinds of apps, so Jake had taken a shot and suggested that they meet up at a bar for a casual drink. Giselle had agreed swiftly, and so here they were. It felt anything but casual. She had peppered him with endless questions at first, inquiring about his work schedule, exercise habits, if he was planning to move or travel, and everything in between. Jake had been to plenty of job interviews, and most had felt more casual than whatever this was.

To add to the tension, Natalie was at the bar, seated at a booth about ten feet away, together with a tall, skinny guy. She seemed to be doing everything to avoid making eye contact with Jake, and he had decided to respond in kind. Still, her presence didn't exactly make this weird date any easier. The two of them had spent a hot night together, and then Natalie had simply dropped out of Jake's life. It would have been nice to have gotten some closure, he thought.

Natalie looked just as hot as before. Jake had only managed to get a glimpse of her for a second or so, but that was enough to know. She had the same curly dark brown hair, and wore a casual but sexy outfit that showed off her curves. He remembered her naked body that night they had gone out together, and quickly cut off that thought before his mind wandered too far. Now was not the right time for that.

"I have to get going in a few minutes." Giselle finally broke the awkward silence, as Jake was taking a sip of his beer. "Thank you for taking the time to meet up with me. It was pleasant. I will be in touch." She got up from her chair, gathered her purse, and strode off, pausing briefly to give Jake one last discerning look. The clicking of her heels seemed to drown out all the other noise in the bar as she left.

Well, this is just great. Jake was now alone in a packed bar, an old flame of sorts sitting a few feet to his right. There was plenty of beer left in his bottle, and he wasn't about to waste it. With a sigh, he placed his phone on the table to give himself some kind of entertainment while he finished his drink.

"Can I get you anything?" A voice interrupted Jake's tipsy train of thought. One of the waitstaff. He had seen her before, on the date with Natalie. A small, cute girl, with green eyes and auburn hair. Dressed casually in jeans, sneakers, and a black t-shirt, she looked expectantly at Jake with her hands clasped behind her back.

"Yeah, I think I'll have uh..." Might as well call it an evening, with a strong nightcap. "Whiskey, please."

"What kind?"

"Oh yeah... Whatever's cheap. Just, you know, a regular whiskey." Jake didn't know what exactly a regular whiskey entailed, but he was too flustered to make a detailed order at the moment. Having Lorelei's, the lady next door's, intricate knowledge of drinks would have been good right now.

The cute waitress lingered for a few seconds, giving him an empathetic smile before going off to fix up a "regular whiskey".

Ten grueling minutes later, Jake had finished his beer and his regular whiskey and was driving back home. He was feeling tipsy now, but he was also definitely under the legal limit, not to mention an experienced delivery driver. On his way out of the bar, he had made sure to keep his back turned to Natalie's booth the whole time while going up to pay and exiting. He had texted Lorelei before starting the car. Hopefully she would be available tonight.

His phone buzzed in his pocket. Lorelei's response only took a few minutes. He'd check it when he got home. He may be a scumbag, but at least he was a safe driver, he thought to himself, as the alcohol made his head spin.

------

"Jake dear, I have been on a million dates. That one would make the top ten weirdest, for sure."

Lorelei sat next to him on the couch. She had dark, curly, shoulder-length hair, and large dark brown eyes. She was wearing a bright green and white patterned dress. Jake didn't have to take it off to know that there was nothing underneath. His neighbor had never worn panties, at least not when he was over, and her lack of bra was obvious from the button-like protrusions poking through the chest of her dress. Her breasts were big and heavy.

"And Natalie was there too?" She said, lifting her thick legs up on the couch, placing her bare feet in Jake's lap. Her toenails had a fresh coat of black paint. "You know, I almost feel sorry for you. Almost."

"Do you like my pedicure?" She asked him, playfully kneading at the crotch of Jake's pants with her toes. He had never been much of a foot guy before, but it felt good. Lorelei's feet were small and soft, and the black paintjob reminded him of Eva, Lorelei's friend who had visited a while ago. He remembered how Eva's foot had been stroking his dick as the two ladies commanded him to fuck them both. Something had awoken in him then. Eva's skin had been much darker than Lorelei's olive tone, but her toenails had also been painted pitch black, like Lorelei's now.

"Yeah, it looks great," Jake said and put his glass down on the table in front of them. His head was spinning a bit. Lorelei had mixed them a couple of strong gin & tonics, which seemed to be her go-to drink. He bent down and kissed her leg, from the toes all the way up to the knee, which made her coo in response. She grabbed her drink and took a big sip before putting it back down on the table.

"Do you think she was scoping you out? Like, figuring out your habits, so she could rob your place when you're not home?" Lorelei asked him.

"I doubt it. Everything about her screamed upper class. What would she have to gain by robbing me, my four year old laptop?" Jake answered. He had already considered that possibility, but it seemed too implausible.

Lorelei snorted and sat back upright, putting her feet down on the floor. She pulled a cigarette out of the package on the table and grabbed the lighter next to it. "I'm gonna have a smoke on the balcony. Do you need any further instructions?" She turned to face him with a mischievous grin.

Jake did not need any further instructions. The two of them had developed a bit of a routine after seeing each other for the past several weeks. He simply gave her a smirk, stood up, and opened the balcony door. The evening air was warm, and the neighborhood was silent as usual. He sat down on the balcony floor, back leaning against the railing, his mouth watering in anticipation.

Soon thereafter, Lorelei stood in front of him, feet planted on the balcony floor beside his outstretched legs. He lifted up her dress and put his head underneath it. His hands then grabbed her big, fleshy ass cheeks, pushing her towards his face, where he was eagerly waiting with his tongue out. Lorelei's pussy was framed by a full bush of curly black hairs. She hadn't shaved since they had met. Jake had grown to like her bush, though he usually preferred it shaven, or at least trimmed.

He stopped close enough that she could feel his hot breath on her pussy, exhaling heavily, waiting for the signal. She was already wet. Jake took in the aroma, as her coarse pubic hairs tickled the tip of his nose. He heard the clicking of a lighter. The signal.

Jake pushed her into his face again. With his nose buried deep in Lorelei's bush, he started lapping at her pussy, from its dripping opening to the throbbing little clit poking out from under its hood. She let out a long, muffled moan, her lips likely sealed around the cigarette. He kneaded her thick ass cheeks vigorously, and intensified his licking, tongue pressed hard against her pulsing clit. Juices started flowing onto his tongue, tasting sweet and tangy.

Lorelei moaned between drags of her cigarette, judging from the sounds she was making. Her hand was rubbing Jake's head through the hem of her dress, pushing his face into her pelvis, coarse pubic hairs pushing into his skin. Jake was straining the muscles in his neck to keep steady, in order to prevent Lorelei from humping the back of his head into the balcony railing.

Jake's right hand slipped away from her ass and down between her thighs. Two fingers found the slick wet entrance of her pussy, and slipped in easily. During the last weeks of seeing Lorelei, he had found a surefire way to bring her to an intense orgasm, provided that she was worked up enough. And she was. His fingers started rubbing against the front wall of her pussy, making squishy sounds as more juices flowed out of her throbbing hole. Keeping up the rhythmic massage of his fingers, he sucked her clit into his mouth as hard as he could, assaulting it with the tip of his tongue.

Lorelei's knees buckled, and her thighs started to tremble, rocking Jake's head back and forth. She seemed to be trying to muffle her moans, but was doing a poor job of it. Juices flowed freely, dripping from Jake's chin down his neck. His cock was throbbing in his jeans, begging to be released. "Fuck, just like that, oh god," his neighbor exclaimed between moans. She started to tumble backwards, towards the balcony door, and Jake removed his fingers from her soaking, throbbing pussy. He knew that she always need a break after a good orgasm, to let her pussy recover. That could take anywhere from one to one hundred minutes. How exactly that was determined, he had yet to figure out.

Jake got up from his seated position on the balcony floor, wrapping his arms around Lorelei's waist from behind, to help her stumble back inside. They fell onto the couch, Jake sitting upright with his back straight, Lorelei landing next to him, resting her head in his lap, shuddering and breathing heavily. If Jake's jeans hadn't been so tight, she would have felt his cock throbbing against her cheek. He felt his ass cheeks clench on their own volition, pressing his crotch up against Lorelei's face.

He stuck his hand under Lorelei's dress, groping for her heavy breasts. "Ooh, gentle please. I just need a minute," she responded. His fingers found her rock hard nipple, twisting and pulling on it. "Aah, too sensitive!" Lorelei squirmed. Jake let go of her nipple, and started lightly stroking her breasts with the tips of his fingers. "Too ticklish!" Lorelei squirmed harder. Then, she rose up, with a sudden burst of determination.

Her fingers started digging at the crotch of Jake's jeans, unbuttoning and unzipping them. He raised his ass up from the couch, and Lorelei pulled his jeans and his boxers down to his thighs with one quick tug. As he sat back down, his member sprung free, diamond hard and throbbing. Precum covered its exposed head, making it glisten. His balls were red and swollen, demanding to be relieved. And relief seemed to be what Lorelei's determination was all about, as she took his cock deep into her throat, while her right hand grasped it by the base. Her palm cupped his yearning balls, making them feel even hotter, as she started bobbing her head up and down, making gagging sounds.

"Ahhh... How's that?" Lorelei said, after she pulled her head up to catch her breath. Her hand was jerking Jake's cock up and down. Her face glistened with saliva around her mouth, and from the tears starting to form in the corners of her dark brown eyes.

"Mmm... Yes, that feels so good, Lores." She seemed a bit taken aback by that. Eva had called her that during their threesome. Perhaps it was too intimate of a nickname? Jake didn't have much time to wonder, interrupting his thoughts with a gasp when Lorelei took his cock into his mouth once again, this time swirling her tongue around it while continuing to jerk the shaft with her hand. She kept this up for some time, while Jake's fingers tangled themselves into Lorelei's curly dark hair, pulling at it playfully.

"I want you to fuck my mouth until you come." She gave him a command. She seemed to enjoy doing that. Jake would have to switch up their roles some time, he thought. He wanted to dominate her too. At this moment however, he did not have much of a choice. He pushed her head down, and she swallowed him into her throat as before. He started moving his hips up and down. Lorelei gagged, and more tears started swelling up in her eyes. She looked so hot like that.

His hand made a fist, grabbing Lorelei's hair hard, as he felt his orgasm approaching. "I'm going to come," he exclaimed, and Lorelei pushed herself down, taking his cock as far as she could into her throat. And Jake came. His cock pulsed as he shot load after load into his neighbor's mouth. His vision blurred, and he felt his body tense up. He kicked the table when the tension reached his legs, almost spilling the glasses on top of it.

Lorelei released him from her mouth, and inhaled deeply. She grinned at him through teary eyes, drool running down her chin. A few globs of cum were scattered around her lips, which she promptly licked up. She smacked her mouth, and opened it to show him that she had swallowed everything.

Jake was still shivering, trying to relax his tense muscles. His head was swimming, and he felt twice as drunk as he was before the orgasm. He stared blankly ahead at nothing in particular, while Lorelei wiped the tears and drool from her face and took a sip from her drink. His cock was still twitching. The very air around it seemed to be electrified.

Lorelei leaned over and gave him a deep kiss, slowly and gently twirling her tongue around his. The kiss tasted like pussy, booze, nicotine, and cum. It was an acquired taste, but Jake had learned to enjoy it over time. His tongue responded in kind, pressing past hers and finding its way into her mouth. The kiss went on, and Lorelei moved her hand down his still clothed chest, slowly finding its way to his radiating member. She grasped it, and Jake felt as if his cock was being struck by lightning. "Haah, no, too sensitive!" he exclaimed, pulling away from the kiss.

"You're spent, huh? I think I am, too," Lorelei said and gave him an empathetic smile. She scooted over and laid down on the couch, putting her legs in Jake's lap once more. His softening cock rested against her ankle. Lorelei yawned, pressing her feet against the edge of the couch in a long stretch. "I'm a very pleasant kind of tired after that," she continued. "You wanna squeeze in behind me on the couch for the night?"

Jake had spent the night on her couch a lot more times than she had at his place, for some reason. He had an actual bed in his apartment, while Lorelei seemed content to just sleep on her couch. The couch could snugly fit the two of them spooning, and they often slept together like that. Jake found it somewhat difficult to get a good night's sleep with the heat from her body and the hair in his face. Not to mention the thick ass pressing against his cock, and the big pair of breasts within the reach of his wrapped around arm. He probably spent more time groping and humping her than he did sleeping, kissing her neck and back while he was at it. She always had a smile on her face and pretended to sleep. Every now and then, she would take Jake's hand into hers and press it hard against one of her breasts.

However, Jake knew that there was a sofa bed inside the couch. The three of them had all spent the night on it when Eva had visited. Why wasn't Lorelei using it? There was a lot more space on it, and the apartment was warm enough that they didn't need blankets, just a sheet would do. He decided to find out.

"Hey, maybe we should pull out the sofa bed?" he asked her.

Lorelei looked a bit bothered by that question. "I don't know. Can't we just sleep on the couch?" She poked him in the side with her foot. "Hey, your place is right there if you really wanna sleep in a bed, you know."

Jake was a bit perturbed by that remark, stiffening up slightly while pondering it. He could indeed sleep in his own bed, but he wanted to spend the night with Lorelei. Being with her felt good. He wasn't falling in love, and was very careful not to give her that impression, but he still enjoyed her company in many ways.

Lorelei must have noticed him starting to sulk, as she pulled her legs back and sat up, wrapping her arms around her knees. "Alright, that sounded mean, I'm sorry." Her voice had a guilty quality to it. "I just don't wanna deal with the whole bed thing. I'm lazy like that. I know, I'm weird. But I wanna spend the night with you, don't think otherwise."

She was weird indeed, but then again, so was everyone who ended up in this neighborhood. "I'll handle the bed. Come on, I'll even put it back in the morning. You don't have to lift a finger," Jake offered her. It would only take half a minute or so to set up, he figured.

"I haven't cleaned it since Eva was over", Lorelei responded.

Jake smiled at that. What a night that had been. "Well, at least we know exactly where stains come from then. Come on, all you have to do is get up for thirty seconds, then we'll be in bed."

"Fine, but you'll put it back in the morning too, like you said," Lorelei grumbled and stood up. She grabbed the glasses from the coffee table and brought them into the kitchen.

Jake stood up as well, and carried the coffee table to the other side of the room. Then, he got to work on clearing the sofa, and pulling out the bed. Lorelei returned from the kitchen right as he finished. The sheets were still on the bed. There were no visible stains, but they did seem to be a bit crusty in some places.

He undressed the remainder of his clothes and laid down on the bed, making it squeak. Lorelei stood beside the bed with her hands on her hips, looking somewhat skeptical. "Come on, get in here," Jake urged her.

Lorelei obliged, pulling her dress off and lying down in the bed next to him. She turned around on her side with her back towards Jake, and he turned around to face her, wrapping his arm around her. Her body was hot and sweaty. Within seconds, she seemed to have fallen asleep. Jake grabbed one of her breasts, closed his eyes, and let his mind wander off.

------

He woke up, an unknown amount of time later. The sun was up, and the street outside was buzzing with noise, mostly cars and bird song. The balcony door was still open. His mouth was dry, and his head was aching. Common side effects of hanging out with Lorelei in her apartment. She was curled up tightly in his arms, snoring loudly.

Her naked ass was pressed against his cock, which was rock hard and firmly planted between her cheeks. He started humping her, almost unconsciously. Her warm, slick ass felt good against his cock. He wondered if he would get to fuck it one day. He had eaten it a few times, and Lorelei had certainly liked it, so she was at least open to some anal play.