Nightshift at Judy's Ch. 1byDancing Sprite©
"You won't do it!" Wendy said, convinced that he was bluffing.
Dave glanced over his shoulder to make sure the only customer in Judy's SuperBurgers was really the person he thought she was. "Yes, I will!" he assured her, grinning from ear to ear.
"No way!" Wendy insisted.
"Sure I'll do it!"
"Then what are you waiting for?"
"Let her finish her meal. It would be rude to interrupt her while she's eating."
"You're trying to chicken out!"
"I'm not! The moment she finishes off her burger, I'll walk over to her and do it."
The next five minutes, Wendy and Dave, cashier and cook at Judy's SuperBurgers, watched in silence as their only customer dug into her SuperBurger, nibbled on her fries, and sipped on her coke. At 3:30 in the morning, she was most likely to remain the only customer for a while longer. At least Dave hoped so, since he'd need a little time to collect his bet.
"She's done," Wendy pointed out immediately when the girl at the table had swallowed the last bite of her burger and fries. "Go ahead! No more excuses!"
"Right. Watch this!" Dave said as he walked around the counter and out into the customer area. "And keep an eye on the front door."
He walked straight to the table the girl was sitting at and bent slightly forward as he talked to her. Wendy watched and listened intently, but couldn't make out what they were saying. As their conversation dragged on for several minutes, however, with both of them smiling and laughing, Wendy got a bit worried and for the first time contemplate the possibility that she might actually lose her bet.
A few minutes later, the girl smiled from ear to ear and nodded enthusiastically. Wendy cringed, fearing the worst. And sure enough, Dave sank down on his knees in front of her, pushed her skirt up and ran his hands all over her thighs.
"Hot damn!" Wendy muttered as the girl raised her ass off the chair a couple of inches, allowing Dave to bunch up her skirt around her waist and pull her panties down. She considered walking over to their table to get a better view, but quickly decided against it. She wouldn't be able to see the door from there, and getting caught would cost them both their jobs which they depended on to pay their way through college.
So Wendy stayed behind the counter, watching with rapt attention as Dave's head disappeared between the girl's spread legs. She couldn't see his tongue working on her pussy and slipping deep inside, but the expression on the girl's face confirmed beyond any doubt that he was indeed eating her out.
Wendy stared at the back of Dave's head with a mixture of disbelief and fascination. As her nipples strained against her tank top and the first drops of moisture began to ooze out of her pussy and dampened her panties, she regretted that she had resisted Dave's advances. Three wasted days -- three wasted nightshifts, she corrected herself -- during which he had kept making passes at her and she had kept turning him down.
Not that she wouldn't have liked to screw him; in fact, she was extremely hot for him and wouldn't have hesitated to spread her legs for him -- in a place where they had some privacy. But screwing him on the job, in a restaurant where people could walk in anytime and surprise them, just hadn't seemed like a good idea. But now she might have to do it. Probably. He had accomplished the hard part already; he had somehow convinced the girl to let him eat her pussy and Wendy didn't doubt that he'd be able to bring her off.
To her own surprise, the thought excited her. Not just screwing him, but screwing him right there in the restaurant. While the very idea of having sex in a public place would have sent her running in the opposite direction just hours ago, watching Dave and the girl doing it right there in front of her eyes aroused her so much that she slipped a hand into her skirt and rubbed her pussy lightly, wishing it was her sitting there with Dave's head between her legs.
The girl in the chair in front of Dave was obviously having a great time. Both her hands were clamped around Dave's head, holding it firmly between her legs and on her pussy, while her head was thrown way back, her mouth half open, and she was trying hard -- although not entirely successfully -- not to scream with pleasure.
Wendy knew that the girl was about to climax, at which time Dave would have won his bet. Some rational part of her mind was still wondering why she had ever agreed to it, but the answer to that question was obvious enough: because she thought Dave was bluffing and she wanted to call his bluff. She had never expected him to really do it. But he was doing it. And he would win. Then she would have to . . .
"Yeah, Dave! Wow! I'm coming! This is fantastic! Yeah!" The girl's screams put an end to her reverie. Wendy looked up and saw her shuddering and jerking in her chair, still holding Dave's head firmly between her legs, obviously in the throes of an intense orgasm.
"Damn!" Wendy muttered again and pulled her hand out of her skirt reluctantly, not wanting them to see her jack off.
When the girl's orgasm subsided, Dave stood up and helped her to her feet. She waved at Wendy and grinned before she pulled her panties up and straightened her skirt. Dave walked her to the door and gallantly held it open for her while she turned and smiled at Wendy. "He's good, go for it!" she laughed merrily before she walked out into the parking lot.
Dave looked longingly at her back for a few moments, then returned to the counter. "I've won," he said proudly, his face still covered with the girl's pussy juice.
Without hesitation, Wendy wrapped her arms around his neck, kissed him passionately, and licked the juices off his face. "I really didn't think you'd do it," she said admiringly. "I guess you want to collect your bet now?"
"Right away," he smirked. "Want to do it here or in the kitchen?"
She dragged him into the kitchen, where they couldn't be seen if a customer walked in on them unexpectedly, and kissed him again. "Just be gentle, I've never done that before."
"You're a virgin?" Dave asked incredulously.
Wendy burst out laughing. "Not really," she replied. "It's just that I've never had a dick up my ass."
"You've missed a lot of fun," Dave smirked.
"You don't say! I'm sure it's a lot of fun for you guys, but for us poor girls . . ."
"It's fun for you girls, too," Dave assured her. "Once you've overcome your inhibitions and done it a few times, you'll love it."
"You say so," Wendy said noncommittally. Although she wanted to believe him, she still had her doubts.
"I'll prove it to you," Dave said. "Now pull your skirt up and take your panties off."
Wendy hesitated a moment, then grabbed the hem of her miniskirt with both hands and wrapped it around her waist. As she slid her panties down her long, well-tanned legs, she stuck her ass out in Dave's direction and wiggled it slightly from side to side.
"Very nice ass," Dave commented as she stepped out of her panties and kicked them aside heedlessly. "I can't believe nobody ever wanted to stick his dick up there."
"It's not that nobody wanted to. I just didn't let them."
Dave shook his head exaggeratedly. "You will, from now on," he said, very sure of himself and his ability to make her enjoy it.
"We'll see," Wendy said as she bent over and rested her elbows on one of the kitchen tables. She stood with her legs wide apart and her puckered anus was clearly visible above her clean-shaven pussy lips.
Dave took his dick out and had it fully hard after a few strokes with his hand. He set out to rub it along her wet and swollen pussy lips for lubrication, but stopped as another idea occurred to him. He quickly stepped over to the mayonnaise squirter and coated his dick with a thick layer of the white, gooey stuff, then extracted another handful, which he proceeded to work into Wendy's asshole.
"Hey, what's that?" she squealed when his greasy finger slipped into her asshole.
"My index finger."
"Smartass! I'd be really disappointed if it were your dick. What's on it?"
"Mayonnaise. Makes you nice and slippery. Now hold still and let me prepare your asshole."
Wendy murmured something in response and spread her feet a little wider apart.
"How did that feel?" Dave asked when he had worked most of the mayonnaise into her asshole.
"Okay so far," she said. "But your cock is a lot bigger."
"Don't worry about it. You'll love it," he said reassuringly and inserted two fingers past the second knuckle. "How's this?"
Dave waited a few moments until her sphincter relaxed a little, then added another finger. "And this?"
Wendy was surprised that his fingers had slipped into her asshole so easily and without causing her any pain. As he wiggled them about and moved them slowly in and out, she decided to go for it all. "Stick your dick up my ass now!" she ordered before she could think too much about it and get scared of her own courage.
Dave grinned from ear to ear as he pulled his fingers out and placed the tip of his mayonnaise-coated dick at her asshole. "Here it comes, baby," he said and pushed lightly. Her sphincter resisted the intrusion for a few moments, then gave way and allowed the head of his dick to slip right in.
"Stop!" Wendy cried out as a bolt of pain shot through her entire pelvis. Strangely though, it mixed with a warm and pleasurable feeling and soon ebbed off, leaving only a dull throbbing.
"Relax, baby," Dave said softly and waited patiently for her to get used to the new sensation.
Wendy took a series of deep breaths while she made a conscious effort to relax. It worked. "Deeper!" she demanded as she adjusted to the dick invading her asshole.
Dave pushed forward and slowly buried another inch of his dick in her.
Wendy inhaled sharply as another bolt of pain spread out from her asshole, but to her relief this one wasn't nearly as intense as the first one and subsided much faster. "Deeper!" she cried again. "Give me more!"
"Here you go," Dave laughed and pushed another couple of inches into her tight virgin asshole.
Wendy felt almost no pain this time and found the throbbing in her asshole thoroughly enjoyable. Together with her euphoria at losing her anal virginity, it made her impatient for more. "Deeper!" she demanded again. "Give me all of it! Shove it all in!"
"That's the spirit, Wendy," Dave complimented her, rather impressed with how fast she had gotten into it. He rammed the last two inches into her asshole and waited for another scream, but to his surprise it never came.
Wendy took a series of deep breaths and held her ass absolutely still, willing her sphincter to relax even more. "God, my ass feels so full," she moaned between deep breaths. "Is it all in?"
"It is," Dave said. "Six and a half inches of dick are buried in your asshole."
"God," she panted again. As she became more comfortable, she began to wiggle her ass slightly from side to side, causing his rock-hard dick to rub against the walls of her rectum. "This is fantastic! Your dick feels so good in my asshole!"
Dave snickered and gently patted her ass cheeks. "Ready for more?"
"Yeah! Fuck me!" Wendy almost screamed. "Fuck my asshole!"
Dave slowly pulled his dick out, then pushed it back in again, just as slowly, relishing the exquisite pressure of her sphincter on his dick as it slid back and forth. The thick layer of mayonnaise, both on his dick and in her rectum, eliminated most of the friction, but still the tightness of her sphincter and the satisfaction of having his way with her and taking her anal virginity excited him in the extreme.
"Faster!" Wendy hissed when the full length of his dick was buried in her again. The sawing movement that had seemed to rip her sphincter apart at first had kicked her excitement to a new level, which she wanted to experience to the fullest before Dave would shoot his load into her and withdraw, leaving her empty.
Dave settled into a slow, easy rhythm to give her time to adjust, then increased his tempo as she began to push her ass back at him and met each of his thrusts with one of her own. After several minutes he reached full speed, pulling his dick out of her almost entirely, then slamming it back in until his hips collided with her ass cheeks and his balls swung into her soaking pussy lips.
Wendy moaned and screamed with pleasure as her asshole got fucked for the very first time. She had already decided that the pain at the beginning had been worth it. More than worth it, actually. As she got used to his dick penetrating the depths of her rectum, she enjoyed it more and more and repeatedly screamed for Dave to fuck her faster and harder.
When Wendy felt Dave's movements getting jerkier and more erratic, she was already on the brink of a powerful orgasm, her very first anal orgasm. To make sure she got off before Dave blew his load, she reached between her legs with her right hand and slipped two fingers into the wet folds of her pussy, where they immediately found her engorged clit and rubbed all around it.
"I'm coming!" Dave groaned moments later and slammed his dick balls-deep into her asshole.
Wendy was ready. When she felt the first spurts of his cum gushing into her rectum, her own climax set in and rapidly increased in intensity. As wave after wave of orgasmic bliss washed over her, she pulled her hand back from between her legs and rested it on the table in front of her to keep her balance.
Dave huffed and puffed behind her and kept his dick buried deep in her asshole until the last drop of cum was spent and his organ began to deflate. The pressure of her sphincter pushed his dick backward until it finally slipped out of her asshole, allowing him to take a step back and look down into her mayonnaise-smeared ass and soaking pussy.
He watched with fascination as a gob of cum trickled out of her asshole, which hadn't completely closed yet, and slid down towards her pussy. "We better clean up," he said as he surveyed the mess on her ass and his own dick.
Wendy stood up with a deep sigh. "God, that was good!" she panted as she gripped a handful of paper napkins and began to wipe her soaked pussy and ass. "I should have done this years ago!"
"I told you you'd love it," Dave laughed as he cleaned up his dick. "You've got one hell of an ass. I want to fuck it all the time."
Wendy grinned from ear to ear. "Guess I could use some more practice. But you'll have to take care of my pussy, too. And I like to give head . . ."
As they both continued to clean up in silence, Dave couldn't help but wonder what he had gotten himself into. But he did look forward to sampling her other holes and appreciated the opportunity to break up the boredom of long nightshifts with few customers during the small hours of the night.
Wendy dumped the last of the napkins in the trash and inwardly sighed with relief that no customers had walked in during their escapade. She grabbed her panties off the floor and stuffed them into her backpack, deciding to go without in case Dave got hot again. "Funny," she giggled, "I think the graveyard shift has just become my favorite shift."