Caring for a Regular

This is a work of fiction. All characters are 18+

*****

Stan sat at the bar alone, nursing a jack and coke and wondering what the next stage of his life would entail. The divorce was hard on him but he still wore his ring, hoping that maybe he would wake up and it would all be a dream.

He never woke up, though. Every day was the same now. He would go to work, stay until seven or eight now that he had no one to go home to, go to a bar downtown, have a few drinks, then head back to the shitty one bedroom he had been renting until the paperwork was finalized. He didn't want to spend the money on a nicer place until his marriage was truly over.

The bartender knew him well. She was a plucky young college student, no older than twenty-one. Long blonde hair tied neatly in a ponytail for work bounced behind her as she walked over to Stan to check on his drink. Her large breasts bounced under her black v-neck, just barely hiding the weight that hung on her chest.

"Everything alright, Stan? You've barely touched your drink tonight."

"And I suppose you'd prefer if I had already bought a few rounds?"

"Well, my wallet would, but I wouldn't. I'd prefer to see you happy." She bent forwards, letting her forearms rest on the bar. Stan was given a five-star view of her cleavage, and he was too downtrodden to bother looking away. "What's going on, Stan?"

Stan looked down at his wedding ring, running a thumb over it. "Messy divorce. Not a fun story."

The bartender gestured to the empty bar. "I've got time."

Time passed as Stan relayed the story to her, giving all the little details and ins and outs of the divorce. She still loved Stan, but not the same as she used to. She had moved on, romantically, and didn't want to burden either herself or Stan any longer than necessary. They didn't have kids so she wanted to rip the bandaid off before things got more complicated.

By the end of the story, Stan had ordered another few drinks and was feeling a bit looser than usual. He looked into the bartender's ample cleavage unabashed. He wasn't hurting anyone, right? Just enjoying the view.

"Thank you for listening" Stan said with a slur. "You know, I don't think I ever asked your name, and I've been coming for weeks now."

"It's Rachel." Rachel looked down at Stan's flushed face and smiled. She felt good about herself knowing he was staring at her cleavage. He was only in his early thirties and was attractive, much too attractive to be getting a divorce with no baggage. He'd get taken off the market immediately by some fox his age in no time.

She squeezed her tits together with her arms and put a hand on Stan's. It was hot under her touch. "You know, I get off in ten minutes. Maybe you could come back to my place for a cup of coffee? We could keep the conversation going."

"Rachel, I'm..." Stan looked away from her cleavage and down to his ring. "I still feel like I'm married, you know?"

"It's just a cup of coffee, nothing more." Stan looked back up at her cleavage. It was like a deep valley between two mountains.

"Alright, fine, but just coffee." Rachel giggled and told him to wait for her replacement and then they could leave. About fifteen minutes later, Rachel's coworker walked in. She yelled at him for being late again, but he just shrugged it off and got behind the bar. Rachel grabbed her bag and walked over to Stan, holding out her hand.

"Come on, let's get going." Stan looked up at her. She was glowing in the dim light of the bar, her silhouette painting an erotic display in his mind. Her legs were long and thin, her ass tight and her stomach flat. Her tits pushed up against the fabric of her shirt, begging to be released from their captivity.

Stan took Rachel's hand and stood up, dizzy at first but finding his footing. Rachel hooked her arm into his and they walked out like a couple, chatting the night away as they walked to her apartment. It was a twenty minute walk, but it flew by as they laughed and joked to each other. Stan hadn't felt that good in months and was happy just to have the company.

Rachel had a one bedroom apartment downtown. It was nothing special, but it wasn't bad either. It was clean, furnished, and well-lit. Couldn't really ask for much more.

Rachel led Stan inside and brought him to the couch and sat him down as she went to change out of her work clothes. She emerged from her bedroom wearing a baggy t-shirt and men's boxers. Stan could tell she wasn't wearing a bra underneath the shirt as her tits shook with each step. They didn't hang low on her torso, surprisingly for their size, and looked like they were actually pretty perky underneath her shirt. He could feel his cock stir in his pants but paid it no attention, still too tipsy to really care.

Rachel brewed up some coffee and brought two mugs over to the couch, sitting down next to Stan as she handed him a mug. Their legs touched together as she sat, choosing to sit right next to him instead of further down the couch. He could smell her perfume, a gentle vanilla fragrance that wafted through the air. It was comforting.

"So tell me, how is it a man like you is single again? I can't believe she just isn't in love with you anymore."

"I don't really understand it either, but I guess some people just change. I thought we'd be together forever, you know? I never would've expected this."

"But you seem so nice, and you're definitely a handsome guy." She grabbed the bicep closest to her and gave it a squeeze. "And so fit!" One of her boobs pressed into his arm as she grabbed it, squeezing softly into him. He could feel her nipple brush against his arm.

"I don't know about that" he said with an awkward laugh, trying to politely move away from her, but she held on tight. Rachel wasn't letting him go that easily.

"Oh, come on. There's no way you don't work out" she said as she fondled Stan's arms. He turned his head to look at her face. Through his semi-drunken gaze he saw a beautiful and vibrant woman caressing him and pressing her body into his. His member began to lurch in his pants, unable to stop itself. Rachel looked into his eyes, her greenish-blue iris' piercing into his own blue orbs. She lifted her head and softly pressed her lips into his. She closed her eyes as her lips made contact; a gentle caress of vanilla perfume rolled into him. Stan's eyes shut momentarily as he felt her silky touch and opened just as quickly when she pulled back only a moment later. They looked at each other for just a fleeting moment before embracing once more. Still with a delicate touch, Rachel pressed her lips onto his. This time, however, she kept them there. They kissed with a subtle sensuality before Stan's hands began to act on their own. They found their way over her shirt, groping her breasts with no sense of delicacy. He was too drunk to care about romance, all he wanted was to feel Rachel's tight, young body. His hands squeezed and kneaded the generous mounds on her chest as Rachel's tongue began to slide between Stan's lips and into his mouth. Her tongue found his. The taste of alcohol and coffee was still ripe in his mouth, but it only turned her on more to finally get to taste his mouth. Their tongues battled like gladiators, Stan's losing to Rachel's dominant and sober approach.

Without breaking from the kiss, Rachel got up and mounted Stan's lap. She leaned into him so that her tits were pushing up against his chest. She wrapped her hands around his cheeks, her fingers a soft bouquet of digits enveloping his face. She moved her hips like she was giving a lap dance, rubbing his now engorged cock through his pants. She could feel it press up through the thin fabric of her boxer shorts and up between her tight ass cheeks. It was massive. Way bigger than anything she had ever experienced. Her pussy salivated at the thought of trying to fit him inside of her.

She leaned back, finally breaking off the kiss. Strands of spit stretched out between their lips until the distance broke them off. She lifted her shirt off her body and brought her tits out for Stan to get a clear view. They only sagged slightly, no doubt due to her youth. Her nipples stuck out like dark red thimbles. Stan instinctively grabbed her breasts and covered her right nipple in his mouth. He sucked on it with wild abandon. Rachel let out a yelp as Stan's teeth gently nibbled at it. She ran her hands through his hair and bit her lip. She pressed further down into his lap trying to feel more of his cock but was unsatisfied because of the fabric barrier separating her and his meat.

Rachel stood up and backed off a foot or so from Stan who was confused about why she got up. She yanked down her boxers to reveal her cleanly waxed pussy, dripping with her excitement. She got on her knees and closed the gap between her and Stan's lap. He looked down at her expectantly, too drunk to ask for what he wanted. He just nodded at her knowingly. Her mouth contorted into a mischievous grin as she unbuttoned his pants and pulled them down below his knees and to his ankles. He lifted his ass just enough to let her pull them down and then plopped right back onto the couch. His turgid cock flopped out and stood at full attention to salute her. She pushed his legs out so that they were spread wide and brought her face to the base of his shaft. Her tongue emerged from her hungry mouth and lapped at his balls. Stan groaned painfully as her tongue lifted and licked them. She let her tongue rise slowly as it found its way up his shaft and left a trail of saliva in its wake. She could feel his cock quaking against her tongue, begging already for release. She had to be careful not to let him cum too quickly so that she could enjoy every inch of him to the fullest. A cock this beautiful needed to be worshipped and she had every intention of worshipping it properly.

Rachel's tongue reached the tip of Stan's engorged cock head, meaty and pulsing with blood, almost purple. It was begging for Rachel to slip her lips over it and swallow it. A glistening bead of precum bubbled at the glans. Her tongue lapped at it, tasting his salty essence for the first time. A shudder took over Rachel's body as excitement coursed through her. Lips puckered, she planted a soft kiss on the tip of Stan's cock. He gave a drunk groan, loud and unabated. The taste of his flesh in Rachel's mouth sent a chill down her spine. His masculine scent whisked her away, threatening to take her control with it but she held firm and steady. The glans was fully encased in her mouth as her tongue licked up and down and around it, tasting and teasing Stan. Without even realizing it he tried to put his hands on Rachel's head but she grabbed them and planted them on his sides, holding them down as she teased him.

"Fuuuuuuuuuuuck Rachel, that feels too fucking good. I'm already gonna...gonna..." but Stan was too lost in the sensation to finish his sentence. Rachel lifted her head and released his cock from her oral grip so that he wouldn't cum too soon. His cock twitched in agony and strained fully taut as the veins popped and pressed against the skin. She ran her tongue along the fattest vein on the underside of his cock until she reached the tip where once again she slid it into her awaiting mouth. Stan groaned again and thrust his pelvis up slightly. Part of the shaft had entered Rachel's mouth. Her tongue stuck out of her mouth as she tried to lick further down the shaft while she sucked. Unable to resist any longer, Rachel bobbed her head slowly, up and down, up and down, giving Stan what he finally wanted. Even though he was drunk, it was easy for him to recognize that this was the best blowjob he had ever received. The way her tongue worked the head and shaft from inside of her mouth was a brand new experience for him. With his cock in her mouth, Rachel looked up into Stan's eyes and shot him a look of tender love that he hadn't expected to see. It put him over the edge completely. Right as he was about to cum, Rachel pulled away once again and left him panting, begging for release with his eyes. She just smiled up at him. It was a mischievous grin that said she wasn't even close to letting him cum yet. Not until she had sated her appetite.

Rachel stood up and gave Stan another look at her impeccable figure. Large, weighty breasts, incredible curves that led down to her wide hips, a flat stomach that showed she worked out, thighs that glistened in the soft light of the apartment, and a dripping wet pussy sitting between them. She groped her tits in front of him, squeezing them and cradling them in her small hands. She bit her lip as she kneaded her tits for Stan, eyeing him like he was her prey.

She let a hand fall down and snake down her stomach to her slit and began to caress it. Stan's cock lurched at the sight of Rachel fondling her tits and pussy. She had him in a complete stupor. More precum dribbled from the tip of his rod. Rachel saw it and knew what lay within his balls for her. A verdant oasis with a pool of semen was hiding in his balls and she wanted it all for herself.

Rachel stepped towards him seductively, hips and boobs swaying side to side. She straddled him, the heat of her pussy encroaching on Stan's incredible length. She leaned into his chest. Erect nipples pressed firmly into him while she brought her lips to his and tasted his mouth once more. Stan's hands reached up instinctively to grope her fleshy mounds. He squeezed them with a ravenous thirst for her that Rachel could tell needed to be quenched. She slipped a hand behind her supple ass and grabbed Stan's pulsating shaft and slid it slowly between her moist lips. They moaned into each other's mouths as their bodies connected and became one. Rachel's tunnel was hotter than a furnace and gripped Stan's thick rod like an anaconda wrapping around its kill.

She slid up and down on his cock, lubing it with her juices. It was a slow effort at first, her tight slit almost unable to take in Stan's massive member. She backed her mouth away from his just long enough to spit into her hand before their tongues reconnected once more. She took her spit-covered hand and rubbed it along his taut shaft, wetting it so that she could take it inside of her. Her pussy slid further down on it, piercing her body like a fencepost being hammered into the ground. She groaned loudly into Stan's mouth as saliva spilled in for him to drink. He released her tits from his firm grip and grabbed two solid handfuls of her youthful ass in his palms. He dragged her body down onto his outstretched pole, reaching depths inside of Rachel that no other man had ever experienced. His fingers went white as he squeezed her meaty cheeks between them. He tried to hoard her ass greedily but couldn't fit it all in his hands.

Stan began to thrust into Rachel as he took control away from her. She let him do it without complaint and simply moaned into him as he pressed his cock further inside of her. Her tits began to bounce with each thrust, her nipples being dragged up and down across his chest. Their tongues fought each other in the arena of their combined mouths, their moans the cries of the crowd cheering on the combatants.

Without any warning, Stan began to shoot ropes of cum into Rachel's hot slit. He was too drunk to even realize he had been pushed beyond the edge of his control and had begun to erupt inside of her. She accepted the inflow of his semen, in love with the sensation of him filling her up. The man she had been fawning over for months was presently cumming inside of her while they fucked on her couch. It was her biggest fantasy being acted out in real life. She quivered as she reached her own climax, juices spraying from her cunt and drenching Stan's pelvis. She quaked on top of him while his cock still pulsed inside of her. Each lurch of his cock sent her into bliss, rivulets of pleasure pulsing through her body.

Stan's cum dripped down his shaft and out of her pussy but he didn't pull out and Rachel didn't lift herself off of him. They stayed still, kissing each other gently as their cum mixed together.