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Heather’s Not so Bad Day

Category: Group Sex
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This was probably not Heather’s best day. She had taken the wrong exit on her way into the city and, after passing by closed factories and chemical plants, the “check engine” light came on. Seconds later, the car shuddered and stopped. Fortunately, or so she thought, there was a garage at the end of the dingy street. The mechanic looked at the car and told her the repairs would be at least $1,000 and that they would have the parts the next morning.

After asking for directions to the nearest hotel, Heather began to walk. If only Don and the kids were accessible — instead, they were camping in an area without cell phone reception. Ah well, Heather thought, I’ll get the nicest room in the hotel, a bottle of wine, and have some “girl time.”

Heather was not blessed with a strong sense of direction, and she soon became lost in an area that became more and more sketchy the further she walked. Her Chanels were not made for walking, however, so she took a break at a bus stop, sitting on the bench and resting her feet. It wasn’t until she stood up that she noticed that her purse was no longer on the bench beside her.

“Shit!” she thought. And then the rain started. It wasn’t a soft rain, either. It was a monsoon-like deluge. She grabbed an abandoned newspaper and held it over her head, but within seconds the orange pebbled Diane von Furstenburg dress that she thought made her look so sexy was clinging to her like a second, very wet, skin. She rushed through the gathering darkness to the one light she could see through the rain and pushed her way through the door. It was a pool hall, dark and smoky, and the bartender, the three men playing pool, and the waitress stopped what they were doing as she stood framed by the doorway. She realized, awkwardly, that her hard nipples were poking through the fabric of the dress, and this was bringing a slow smile to the men in the bar (not that the waitress took her eyes off of Heather).

She mustered her courage and walked up to the bar, her high heels clacking self-consciously on the floor. “Can I have a glass of red wine, please?” She asked the bartender.

“This is all we have,” the bartender said, showing her a bottle of cheap red wine that made her cringe inwardly.

“I’ll take it,” she said. The bartender, a tall, well-built man, poured the wine for her. She drank it in three quick sips in less than 5 minutes and then asked for another. As she nursed the second glass, she decided to end the awkward silence and began chatting with the bartender. By the third glass she was relating the story of her day.

When she finished, the bartender said, “So you’re wallet is gone?” Heather nodded, her mouth full of wine. “Then how are you gonna pay for the wine? Or your car?”

“Oh, shit!” Heather thought. She looked over at the pool table and had an idea. “I’ll play you for it! If I lose, I’ll wash your dishes.” Surprisingly, the bartender agreed. The game proceeded quickly. Heather noticed that every time she bent over to take a shot, the men were at the other end of the table admiring her cleavage. Of course, this made her self-conscious, and her nipples swelled again. And the wetness began again, but this time between her legs.

She was doing surprisingly well. “Is he always this bad?” She asked the waitress who had sidled up beside her. “Not usually… he must be distracted,” she said, whispering in Heather’s ear and brushing her arm with her breasts.

Heather won the game easily… but then she decided to take it a step further. “Let’s make this more interesting,” she said. “Let’s up the stakes.” Beating him had been so easy. “I need $1,000 for my car,” she said.

“What’s in it for me?” the Bartender asked. “What do you have right now that’s worth $1,000?”

Heather felt bold and over confident. She put her arms on the pool table, mashing her breasts together to deepen her cleavage, and smiled “I’m sure you can think of something.”

The game took longer this time, and went down to the last ball — and Heather lost… “Double or nothing,” she blurted out in desperation. This time he cleaned the table before she even had a turn with the cue. Then he walked over to the door, put the “closed” sign up, and pulled the blind down the door’s length.

Heather stood by the pool table and watched him as he turned from the door. “A deal’s a deal,” she said, and she pulled the sash of her dress, allowing it to fall open. The bartender smiled at the sight of her trimmed pussy. He walked over and pushed the dress off her shoulders and then unhooked her bra. She stood naked in the middle of the pool room with the bartender, the three patrons, and the waitress.

Now it was the bartender’s turn. He pulled his t-shirt over his head, pushed his sneaker’s off, and then, with one movement, pushed his jeans down and off. He now stood before her naked. The two of them being naked in front of the spectators was making Heather very wet and very horny. The sight of his eight-inch cock didn’t hurt, either… She knelt on the floor in front of him and began licking his hard shaft, letting her tongue run along the vein, up the shaft to the tip, and then swirling it around the head. She took the head into her mouth then, sucking lightly, then harder, then taking in more cock, then sucking harder, bobbing her head back and forth. She held his cock with one hand and stroked his balls with the other. He grabbed her hair and pushed her down on his cock so that it reached the back of her throat and then went down her throat.

As big as his cock had seemed, her attention to it seemed to be making it grow even larger in her mouth. Then, he suddenly stopped her, pulled her up until she was standing, and then gently lifted her up and laid her on the pool table. He climbed onto the pool table and lay on top of her and began kissing her, gently at first, kissing her neck and biting her ears — arousing her… Then he put his mouth on hers and thrust his tongue against hers. The invasion was so erotic that Heather almost came. She returned his kiss, pressing back up against him. Their mouths locked, his hands rushing over her body and settling on her tits, her hands on his muscular back, pulling him into her. He slid down her body and took one of her breasts deep into her mouth, sucking hard, twirling his tongue around the nipple, biting it gently, then harder. She moaned loudly, throwing her head back and writhing. When she opened her eyes, she saw the others watching them, and the thought of the two of them putting on a show caused her first orgasm.

The bartender felt her shudder and immediately shifted his attentions, sliding further down her body and putting his mouth over her pussy. His tongue dipped deep into her cunt, lapping at her juices, drinking up her orgasm. And then his tongue found her clit… It flicked against her clit, alternatively fast and slow, hard and soft… until she climaxed again, even harder, grabbing his head and pulling it into her pussy, pulling that tongue onto her clit…

She caught her breath for a second and then he was on top of her again, kissing her with the taste of her pussy on his lips and tongue. She sucked his tongue deep inside her mouth as she felt his eight-inch cock press against her thigh. She reached down and grabbed it, pulling it towards where she wanted it so badly… He paused with his head just touching her pussy lips, then slowly entered her with just the head of his cock. She was wet, but his cock was massive, and as he pushed slowly inside her she felt as though she were wrapping herself around pole. It was so big that she felt like she could feel every ridge and vein of him as he thrust into her over and over again. The feeling of this massive cock pounding into her, of his chest against her tits, of his tongue (that tasted of her pussy) in her mouth… led to a climax that almost threw the 200 lb bartender off of her. Her climax was followed almost immediately by his, and she felt his cock swell inside her, and then he was jerking involuntarily and groaning, and his hot seed was shooting inside of her, pump, pump, pump…

He pulled out and rolled over beside her… “Damn boys, she’s fucking incredible — why don’t you try her?” Heather was startled, but then the bartender rolled over and looked at her and said “You said ‘double or nothing,’ didn’t you?”

The other three men started to strip down; strangely, the waitress remained standing where she was, her tray of drinks still in her hands. When Heather turned her attention away from the waitress, she found the men crawling onto the table. One very quickly inserted his seven-inch cock in her mouth, another began to suck on one of her breasts, and she could feel the third positioning himself between her legs. The cock in her mouth wasn’t as long as the bartender’s, but it was thicker, and she ran her tongue around the mushroom shaped head of the cock before taking it deeper into her mouth. The man sucking on her tit had a bigger mouth than the bartender, and was taking almost all of her 36C tit into his mouth — the feeling was incredible. She could feel the third man rubbing the head of his cock against her pussy lips, driving her crazy with anticipation.

“Wait a minute, boys,” the bartender said. “Why don’t you fill her up?” At those words the men stopped what they were doing and gently pushed Heather up into a sitting position. Then she saw what they intended. The third man was laying down on the table and — Good Lord! — his cock was at least nine-inches long. She crawled on top of him with a mixture of fear and excitement and, grabbing his shaft, she slowly began to lower herself onto his cock. The first man stood up on the pool table and stepped over to put his thick cock back in her mouth, while the second man disappeared behind her. Soon she found her rhythm, bouncing up and down on that massive cock and sucking on the thick one. Then she felt the second man’s hand on her shoulders and she knew what was about to happen. She heard him spit on his other hand and could picture him lubing his cock with it. Then she felt something pressing against her rosebud — it was hard and very large. “No, you’re going to have to loosen her up, Jesse,” the bartender said, and then she felt his tongue tickling and probing her. Now she was bouncing up and down, not just to take in the nine-inch cock, but to press her ass against the probing tongue that was driving her wild.

And then the magic tongue was gone, and something hard had taken its place. She slowed her movements now. The first man took up the pace and began to thrust his cock in and out of her mouth, one hand behind her head, pulling her into him. The third man waited beneath her for the second man to put his cock in her ass…

There was pressure, and then a sudden feeling of penetration, replaced by the tingling feeling of his cock head inside her ass. Then, slowly, he began to inch his cock forward… Now Heather felt as if she was being wrapped around not one pole, but two. She was going to split… And then he was all the way in. He waited for a few seconds, both of them savoring the sensation, and then he began to thrust. His thrust got her started again, and soon she was bouncing back and forth again, forward onto the thick cock in her mouth, and then backward taking the two shafts deep into her pussy and ass… Suddenly, she felt the cock in her mouth stiffen… the head swelled… the man groaned… and hot streams of semen shot into her mouth… He pulled out and the cum shot across her face and then spurted across her tits. Seeing the pearls of cum draped across her face and breasts, the man beneath her stiffened and groaned and suddenly his cock was throbbing in her pussy and she came with him, thrusting up and down even faster, intensifying the feeling. Her quickened motions caused the man in her ass to grab her hips, then gasp, and then she could feel his cock throbbing in her ass as he came. Ropes of cum shot into her and then he pulled out of her and she could feel his come shooting across her ass…

Slowly and surprisingly tenderly the three men disengaged from her, and she lay on her elbows, holding her cum-covered tits off the table. Unexpectedly, she felt a soft touch on her lower back and she turned her head to see the waitress standing there. “Why don’t we get you cleaned up, honey? Come with me — we’ll go back to Fred’s office, he’s got a couch and a little bathroom back there.”

Heather shimmied off the table, feeling the cum on her ass begin to trickle down the crack. Then the waitress’s hand was there, stopping the flow, and the movement as they walked back to the office caused the waitress’s hand to rub the cum into her ass at its most sensitive spot — where the lower back ended and the cleft of her ass began.

The waitress closed the door behind her when they reached the office and had Heather sit on the couch. She knelt in front of her and said to herself, “Well, well, where do we start? There’s cum all over your tits you know,” the waitress said, as she put her hand under one of Heather’s breasts and fondled it. Heather’s nipples immediately reacted, and this may have prompted the waitress to go a step farther. “I don’t think we have anything to wipe you off with,” she said. “We could rub it in,” she said and started to massage Heather’s tits. “Or we could use my shirt to wipe it up,” she said and stood and pulled her t-shirt over her head, revealing two nicely shaped tits, behind a lacy green bra. “Maybe,” she said, looking at Heather’s nipples and then in her eyes, “I could lick it up…” And then she leaned forward and took one of Heather’s cum-covered nipples into her mouth… She sucked lightly at first, and then took more of Heather’s breast into her mouth while her hands reached behind Heather to pull her forward into the waitress’s mouth.

Then the hands shifted and were on her shoulders, pushing her back down along the length of the couch. The waitress stood, tossed her blonde hair back over her shoulder, discarded her bra and pulled her skirt down to reveal a neatly trimmed blonde pussy with glistening, pouting lips. Heather reached out for her and the waitress climbed on top of her, laying down the length of her body. Their mouths met in a passionate kiss, tongues darting in and out; their breasts met, their hard nipples pressed against each other; their legs entwined so that both pressed a leg against the other’s wet pussy.

Heather broke the embrace by moving her hands down to the blonde’s ass and pulling her pussy forward towards her hungry mouth. The waitress responded, sliding forward, leaving a trail of her juices up Heather’s body, lingering to rub her clit against Heather’s stiff nipples, then she twirled about so her pussy was over Heather’s face and her face was over Heather’s pussy. Heather could feel the cum oozing from her pussy and ass, and she could feel the waitress’s tongue lapping it up and probing deeply into both orifices. Heather, too, drove her tongue into the waitress’s pussy, and then ran it teasingly around the rim of her rosebud, plunging it into her ass when the waitress squirmed.

The waitress had found her mark, however, gently nibbling Heather’s clit, licking the length of her slit, and then returning to her clit. Heather was moaning in response — it felt so good to be eating pussy again and to be having your pussy eaten at the same time… One more lick and she came hard, twitching and writhing beneath the blonde, in the most intense orgasm yet. She shuddered over and over, moaning “Oh my God, oh my God, oh my God!” as the orgasm wracked her body and she lost control.

When she regained control, the blonde was sitting on top of her, smiling. Heather smiled briefly and then pushed the blonde back on the couch, rolled off and positioned herself on her knees on the floor between the blonde’s legs, and began to hungrily lap at her pussy and lick her clit. She put a finger in the blonde’s pussy and felt her react, so she began thrusting two, then three fingers into her. The blonde’s pussy tasted incredible…

Behind her, Heather heard the door open, but she didn’t look up from the blondes’ pussy. “What have we here?” said the bartender, and then Heather heard the door close, and the bartender’s bare feet padding across the floor. He positioned herself behind her, between her legs, and she felt him position his cock between her pussy lips. She rolled her hips back to take him inside her as she ate the blonde’s pussy; he responded by thrusting forward with his big, thick cock. The blonde started to whimper and moan, her voice growing higher and higher as Heather pressed her face deeper and deeper into the blonde cunt. Suddenly, Heather was hyper-aware. Aware of the soft hairs of the blonde pussy caressing her face; aware that the blonde was cumming in her mouth, squirting an enormous amount of cum, and that the cum was running across her tongue and over her chin; aware of the massive cock in her pussy, every ridge and vein, the mushroom head, the bartender’s coarse pubic hairs scraping her ass in an incredibly erotic way… and then he was cumming and she could feel him throbbing and spasming, feel him filling her with his sperm. She came then, with her mouth full of pussy and her pussy full of cock and semen, and she could feel the walls of her pussy contracting and releasing around his cock, her cum traveling down the shaft and out of her pussy to trickle down her legs. She had an almost out of body experience caused by the most intense sensation of pleasure she’d ever known…

When she recovered her senses, she was on the floor between the blonde and the bartender. They were kissing her tenderly, gently caressing her tits and pussy with their lightest touches. “You’ll get your $2,000 now…” said the bartender. “But you’ll have to promise to come back and visit us,” said the waitress, as she rubbed her breast against Heather’s arm and ran her hand across her pussy. Heather leaned her head forward and shared a long, passionate kiss with the blonde, and then turned her head to the bartender and gave him a similarly deep, intense kiss. He got up, went to his desk, and returned with an envelope full of hundreds, which he placed in her hand. Then she stood up, and walked into the pool room with her shoulders back and tits thrust forward. She retrieved her dress and her shoes, threw the bra at the three men standing open-mouthed at the bar, and walked out the door…

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