I Dare You

bypstory©

It was a dare she never should have taken. She'd been at it all night, and she was only 1 away from her goal. But it was 1 AM - and she was exhausted. But luckily, she didn't have to do any "work" right now. Looking down the bed, to between her legs, she could see Bob as he lowered his head to eagerly begin licking at her pussy. As she watched, she thought back to the beginning of the night.

It had all started over dinner, 7 hours ago. Shelli was both going through a bit of a drought and hadn't had a steady boyfriend for a while. Oh, it wasn't that she couldn't - Shelli's long legs, round, firm ass and 36D tits virtually guaranteed her any guy she wanted. But she was "selective". Unfortunately, she hadn't found the right guy for a while. So tonight, she was spending the evening with her friend Gail.

Where it came to relationships, Gail was as different from Shelli as night and day. She could be described as a "wild child". Gail would fuck anything with 2 legs and a cock. Check that -- she didn't need the legs. Shelli was amazed as the mass of sex toys that Gail had acquired over the years, wondering how she could actually use so many.

"What you need to do is just get out of your rut. Go find some guys to just spend the night with. You're too young to be tied down," Gail was saying over desert. She'd been on this theme all night, trying to get Shelli to just entertain the thought of a one-nighter with a guy.

"I keep telling you Gail, I just couldn't do that," Shelli replied.

"Look, all you need is the right motivation," Shelly grinned, as a plan began forming in her head. "What if I dared you to outdo me?"

"Huh?"

"It's simple. I dare you to go out, and screw, or be screwed, by more guys than I've done in a single night. Do that and I'll give you a hundred bucks AND pick up tonight's dinner"

Shelli's mind reeled. Something like this was so out of the norm for her. But she did have to admit that she really missed having a cock shoved in her. Besides, how many guys could Gail have done in a single night? Sure, she enjoyed herself, but it's not like she was a hooker, or anything.

"Sure. OK," Shelli had said after a deep breath, and a look around the restaurant. "How you going to know I've done it?"

"Oh, I'll know!" she giggled. "I trust you not to try to fudge the numbers. But remember, it has to be guys. Toys DON'T count!"

"Ok," Shelli grinned. She got up from the table and prepared to head out. "So.....what's your record?"

"Five!" Gail said, deadpan. "So, you'd better get out of here and get hunting!"

Now Shelli's head really started spinning. Five! How was she going to find 6 guys to fuck her, all in one night? With a stunned look, she headed towards the door. Gail watched her go, without another word, and a huge grin on her face. Oh ya, she'd know if Shelli was lying or not!

Bob was definitely skilled at this. Pushing and rubbing his tongue against Shelli's clit brought her back around to the here-and-now. Her head rolled from side to side, enjoying as he massaged her. Reaching down, she grabbed her tits, kneading them, then pinching her nipples. Between this, and Bob now pushing his tongue into her open pussy, she felt a shock run through her. Bob was good...very good...even better than Doug.

She had left the restaurant, and started down the street, wondering how she was going to even start with this task. This wasn't like her at all. But Shelli did admit that there was a certain excitement to it -- even if it did also scare her a bit.

She was still wondering where to start when she passed the door to an apartment building, and the answer struck her -- Doug! Doug was an ex that she had dumped a while back. He had always said if she wanted to stop by, she could. Well, here was her chance. But she'd have to make it quick!

Walking up the stairs, she worked out her plan. But as she approached his door, she paused, wondering if she could carry through on this whole thing. Doubting whether this was right for her or not, she began to turn away....just as Doug's door opened. "Shelli?" she heard behind her.

This had to be a sign, she thought. Steeling herself, she turned, and walked right up to him. Grabbing him by the shoulders she pulled herself to him, and locked him in a deep, passionate kiss. "I want you...right NOW," she said, pushing him back into his apartment.

"This is a surprise!" Doug replied.

"We're not getting back together, Doug. I just want to get it on with you. If that's fine, then let's go!" she gasped. She couldn't believe she'd just said it! Fearing a rejection, she glanced down. But when she looked up, he was undoing his pants! "Any preferences, tonight?" she asked.

"You know what really turns me on," he replied. And ya, she did.

Heading to the bedroom, they immediately got into a 69, with Shelli on top. She began bobbing up and down on his erect cock. Meanwhile, he started by licking all over her pussy, first driving his tongue into her, then sliding out and swirling around her clit. Quickly he pulled one of his hands from under her legs, and pushed first one, then two fingers into her hole. Shelli released his cock from her mouth as she gasped. She ran her tongue around the ridge at the base of the head of his member. She knew he liked that -- his body tensed up, and she could see the head begin to swell slightly, it turning darker red.

Doug's response was to jam a third finger into her, sucking hard on her clit. This made her begin to shake with pleasure. Shelli dropped down on his cock. She had gotten good at deep-throating when she was with Doug. He liked his oral sex, and she knew how to make him feel good! When her lips touched the very last inch of his cock she felt him tense, and his cock grew more at the back of her mouth and throat. Doug grunted hard and pulled her tight against him. He wrapped his mouth around her clit, and sucked as hard as he could. Simultaneously, he began to empty his load into her waiting mouth.

She swallowed him, beginning to feel her own body tense up. Shaking, she climaxed herself, pushing tightly against his mouth.

When they had both completed, Shelli rolled off of him, catching her breath. Knowing she was on a timeline, she wasted no time, getting her clothes back on.

"Hey, where ya going," Doug asked?

"I told you we weren't getting back together, Doug," she replied. She pulled on her shoes, and headed towards the door. "Thanks babe!" she said as she headed out the door, leaving him still on the bed, naked. Once in the hall, Shelli stopped for a second, thinking about what had just happened. She WAS able to just walk away. Thinking about this, she headed down the stairs. Count one!

Bob was now running his tongue round and round the opening to her pussy. Shelli loved how this felt, the skin there so sensitive. Beginning at her opening, he ran his tongue around, circling tighter and tighter, each pass going just a bit deeper into her. Shelli began lifting her hips, trying to get herself closer to his eager mouth. Pausing, Bob inserted a pair of fingers into her. She noticed that she was started to get rather sensitive, and a bit sore, down there. But stopping was not an option at this point. She just wanted Bob to keep going. "More," she moaned. And with that a third was in her! She was still amazed that she was finding this as satisfying as earlier in the night.

Leaving Doug's, Shelli decided that she had to find a "target rich environment" to get a couple of guys. A club, that's what she needed. And she knew just the one. There was a singles club just a couple blocks over.

The line up at the door wasn't a problem -- never had been for Shelli. A good looking blonde woman, long legs, nice tits.....the bouncers immediately had her in the door.

The music pounded inside the club. Shelli looked around, the place very full. She made her way to the bar, where several guys immediately offered her their seats. Rather than declining, her normal practice, she started to size up the offers, picking a good looking, well kept guy, with brown hair and the bluest eyes she'd ever seen. He obviously kept himself in good shape. And, most importantly tonight, he looked interested, but not sleazy. "Thanks," she said, as she took the offered barstool. "I'm Shelli".

"Hi. I'm Chuck," he replied.

Over two rounds of drinks, they entered into some small talk. It turned out Chuck was recently "un-attached", his ex not being interested in any kind of intimate contact. This was a perfect pick, Shelli thought.

"So, how long's it been since you've gotten any?" Shelli finally asked, rather bluntly?

Chuck was obviously surprised by the question. "Well, a while," he said, tentatively. Shelli got up, and whispered that they should go then. Taking Chuck by the hand, she led him over to towards the washrooms. Sticking her head in, she made sure the women's was empty, then pulled him in with her. Chuck turned and locked the door. "Wouldn't want anyone walking in!"

"Oh -- you're not an exhibitionist?" Shelli teased. Unbuttoning his shirt, she found a well-toned body. "Nice," she added, playing with his nipples. Chuck's head dropped back, his eyes closed. "Ahh, I see you like that". Shelli moved closer, sucking on first his left nipple, then his right. At the same time, she unzipped his pants, and ran her hand down to grab his dick. "My, what a big tool you have!" she said with a laugh. "I think we should do something with that"

Shelli turned to face the mirror. Her back was to him, but she watched his reflection as she undid her top, exposing her breasts to him. Then she hiked up her skirt, and pushed her thong down to the floor, shoving it into her purse. Bending forward, Shelli then placed her hands on the counter, and backed up, pushing her ass against his now rigid member. She was right, it WAS big. Fully erect, it was pushing out the top of Chuck's underwear. "Push it in," she moaned, rubbing back and forth.

Chuck needed no additional prompting. He pulled down his shorts, and flipped up Shelli's skirt so it was on her back, exposing her fine ass. She spread her legs apart, an inviting view. Without another word, Chuck pushed himself into her, making both of the gasp. Shelli was glad that she hadn't run into Chuck as her first guy. She was sure that that much dick would have torn her open!

Reaching around and grabbing her hips, Chuck began pumping on Shelli's pussy, driving himself deeper and deeper. At the same time, Shelli pushed on the counter, feeling him bottom out inside her. Faster and slower, faster and slower, Chuck kept pumping away until he couldn't hold himself any longer. He yelled, "Oh my god!", and pulled hard on her hips. She could feel him fully inside her, the head of his dick against the wall inside her. He came with such force that she could feel it coming out of him and spraying into her! This, of course, made her cum again, for the second time this night. As they both moaned in pleasure, their pace began to slow, until eventually Chuck came to rest with his now softening member still inside Shelli, both of them with their hands on the edge of the counter, resting.

"That was GREAT," Chuck panted, as he began to pull out of her.

"Ya," Shelli replied. "Why don't you head out, while I get cleaned up?" After getting his clothes straightened up, Chuck tentatively opened the door, and headed out. Shelli watched him go, then cleaned up herself. Opening her purse, she looked at her thong, and decided to just leave it where it was.

Knowing that she couldn't afford any attachments tonight, she peeked out the restroom door, and headed out of the club through the back way. There were other clubs to hit this night, and it was almost 10 o'clock. Still four to go.

About a block down the street there was another club, and another line. Flirting with the bouncer had the usual effect -- she got in right away! This place was definitely full though. The dance floor was just a mass of people packed together. Figuring that she could use this to her advantage, Shelli made her way to the floor and began working her way through the crowd.

As usual, she had no problems getting offers to dance. But one was too sleazy, the next too eager. It only took her about 15 minutes to find her next likely target. Good dancer, good looking too. They had danced to 2 songs, when a Latin beat began playing. Taking this as an opportunity, Shelli turned around, and began grinding against the guys crotch, wiggling seductively. She knew that things were going well when she felt his hands on her hips, and his cock through his pants!

The song came to an end, and the pair tried to find themselves a seat. This was going to be a challenge! Eventually, they found the end of a booth that was free. Problem was that there was only really space for 1. This wasn't going to be an issue for Shelli. She'd discovered that she could see opportunities in these sorts of things. She pushed the guy down towards the seat and plunked herself down on his lap. The music was extremely loud, so general talking wasn't going to happen in this club. She tried talking directly to his ear, that they should find someplace quite or private, but he just couldn't hear.

Suddenly it came to her. Taking his hand, she discretely moved it so it was just under her skirt. He had a good idea what she was driving it. He ran his hand up Shelli's leg, a single finger tracing where her thong should have been and down to the top of her pussy. Shelli looked into his face, with a grin, and just nodded. He smiled and nodded back. Now for the next step -- she had to figure out how to get him inside. Tilting her head to the side, she held up her left hand and made an "O" with her thumb and forefinger and slid her right forefinger in. Again, the explanation was clear, and with a nod, he agreed.

Shelli partially stood up, using her skirt to cover his mid-section. Quickly he undid his pants and pulled out his cock under her skirt. Seeing him nod, Shelli sat back down, making sure that he impaled her. God it felt good. She began to gyrate to the music, hoping that what they were doing wasn't too obvious. It only took 2 songs, and Shelli felt his arms reach around her waist, pulling her down and towards him. She could feel him shake slightly. Turning, she could see the pleasure in his face.

Eventually, he indicated that she should probably get up. Shelli was trying to figure out how she was going to get to the washroom to clean up. But when she stood, again holding her skirt to cover things, she noticed him grab a napkin from the table, and shove a condom into it. Perfect.

When he was done, she turned around, and gave him a deep, wet kiss. Smiling, she waved to him, and started across the dance floor. That was interesting, she thought. I never even got his name!

Bob now had Shelli up on her knees, with her pussy suspended above his face. This allowed him to not only suck much harder on her clit, but also get a toy into her pussy. A big cock shaped toy. It was not like any toy that Shelli had seen, the end of it swung back and forth if it was on outside her. And she could feel it moving inside her. God it felt good. As he pushed it in, it stretched her, and she shook as the wave of pleasure moved over her. Gail had said "no toys", but this one was in the hands of someone else, so Shelli was going to count this no matter what -- and she knew, so would Gail. She liked being up on her knees with a guy in her. The sensation was always more intense for her this way. She could feel it, her climax would come soon. But this wasn't the first time she was on her knees this night. Funny, the last time she ended up this way too.

Leaving the club, Shelli had decided that she really needed to find someone soon, if she was going to make it to 6 guys tonight. But she was half way there. As she left the club, she noticed the line was longer than ever. Hmmm -- another opportunity.

She worked her way down the line, sizing up each guy she saw. Each guy that didn't have a girl on his arm, that is. Finally, she found an interesting one. Well muscled, nice hair. He seemed to be with a couple of friends. So she decided to talk with him. The line wasn't moving at all, so this worked in Shelli's favour. Eric eventually suggested that they get a coffee, or anything else, just so long as it wasn't standing in this line any more.

"Sure," said Shelli. "I'm game for something". With that they said good-night to Eric's friends and found his car, over in a lot off the main street. Shelli looked - there was no one around in the lot. Eric obviously was not poor. He led her to a well-kept, large Cadillac.

"Where to?" Eric queried, unlocking the doors.

"Why don't we just stay here for a while?" Shelli had already opened the door to the rear seat, and was climbing in. Eric shrugged his shoulders, grinned and climbed in the back with her. She was definitely glad for her good looks this night -- no convincing required. Of course, find a guy who isn't interested in sex!

This encounter began with some kissing. It was only 10:45pm, so she had some time for foreplay. And besides, she found it fun. Eric liked to probe around with his tongue, and Shelli wasn't going to stop him. Eventually, he started sliding a hand up her top, tentatively at first. To help him understand the mood she was in, she reached under her top and popped the clasp on her bra, releasing her boobs. This hint was all he needed. He pulled off her top, and began sucking on her tits. She could feel the tingling from her nipples all the way down to her crotch. Reaching over, she began rubbing his cock, through his pants. He wasn't overly large, but he was definitely hard!

She undid his pants, and she got a bit of a surprise. He was commando. As soon as the zipper went down, his cock leaped out of his pants. She began stroking him, still enjoying him playing with her tits.

Pushing him back slightly, Shelli leaned forward and ran her tongue up the length of his shaft. Lightly taking the head of his cock into her mouth, she kissed him, then looked up at him.

"You want to fuck me?" she asked. He just nodded. This had to be his lucky night!

Kicking off her shoes, Shelli planted her knees into the back seat -- her head at the door. "Then do me, right here!"

Eric moved to behind her, and lifted her skirt. "Hey! We're both commando!" he exclaimed. Her only reply was to reach back with one hand and pull him, by the cock, towards her waiting mound. He shoved himself in.

As he starting moving back and forth, Shelli immediately, and unexpectedly, came. And it was forceful! So much so, she squirted in the car! It must have been because she hadn't cum in the club, sitting on that guy's lap.

"Don't worry about that," Eric chuckled, sliding in and out even harder. The pumping continued to the point where the car was rocking back and forth. It was amazing that no one stopped to see what was happening.

Shelli reached up under herself and began playing with her clit, while Eric continued to pound away. She could feel herself reaching another climax, just as Eric pushed the hardest of all, pulling her towards himself at the same time. This time they both came together, a loud groan from both of them.

Shelli was starting to get tired by this point. She made some excuses about losing track of time, hurriedly told Eric that she lived just a block over, and exited the car. She could hear him offering to drive or walk her home across the lot, so she just waved and yelled that it was OK.

She was definitely tired, and about ready to pack it in. She'd given it a good try, but she wasn't sure she could find another guy. As she walked around the corner, a little café caught her eye. Unlike the clubs, this place was absolutely empty. She walked in and sat down. Shortly a great looking blonde guy, about 5'9", came over and asked what she wanted. "Just a coffee," Shelli said.

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