Do You Dare

"Before tonight, you mean?" Ashley asked. She shifted uneasily in her seat and closed her eyes as she thought about what she'd dreamed of, alone in her bed.

"I played Basketball in College." Ashley croaked. "I mostly sat on the bench, unless the game was a blowout. I was desperate to play in the homecoming game against our rival. Something to remember my time there, other than some dusty degree. The rest of my team offered me the opportunity to prove myself. I had to agree that if I wasn't good enough and failed their test, I would be punished for wasting their time." Ashley turned away for a moment and sipped a drink.

"I asked what I would have to do... the penalty was.... sexual." Ashley now looked directly at Jennifer. "I backed out. Lost my nerve." Taking another sip, Ashley paused and took a deep breath. "I always fantasized about what would've happened. In my fantasy, I played my hardest but wasn't good enough. Ever since I wish I had gone that day. Found out what would have happened." Ashley gulped, as she started to reveal her deepest thoughts. It seemed crazy that this would be harder than revealing her naked body to these strangers.

"I think about how they might have taken me, surrounded me, and made me strip off my uniform. Make me crouch over a basketball, at center court, and masturbate until I came. I would rub myself hard, in front of my teammates. I'd be right on the edge before I realized someone was recording me." Ashley coughed again.

"I'd complain, but they wouldn't let me stop. They said this was just in case I didn't finish... to give me motivation not to back out... so I had to continue. Rubbing myself, playing with myself, all while they watched,..." Ashley could feel herself blush as she continued. "So I came, eventually. I fantasize about how they mock me while I do it... and they act all horrified that I've made the basketball wet." Ashley stopped and took another swig of her drink.

"... they say that this means I have to pay another penalty. I protest, but they have the video. So they lead me over to the goal, They have handcuffs... I don't know why exactly... but they handcuff me to the post... they.... ummm.... they then tell me the men's team is scheduled to practice soon, and then... then they all just silently turn and leave. I don't even beg them to let me go. I just stand there. Naked. Helpless. Unable to cover myself.... then the men strut onto the court...." Ashley's voice faded out. Looking around her, she cursed herself as she heard the words come out of her mouth. "... and that's the end of my fantasy."

Idiot! Ashley berated herself. Twelve, just twelve more points, and Jennifer will be her possession. Great time to lose your nerve! Ashley toyed with her drink, waiting for her score.

"That's not the end. Is it?" Jennifer coaxed Ashley. "Of course if you don't want to... I can deduct points."

Jennifer's light nudge dragged Ashley back into the real world. Mumbling something into her drink, Ashley at the audience and saw that they wanted more. Ashley stared down the barrel of a one, or at best a two-pointer. That had the very real prospect of costing her the game.

"As... as the guys come over, I don't say a thing. The team captain, a tall beautiful black man, asks if I want to be untied. I hear a voice say 'no'... and I'm shocked to realize it's my voice. I said 'no'." Ashley dipped her head down so that she could continue without having to look anyone in the eyes.

"They tell me we're going to play a game. They blindfold me, and then I hear them drop their shorts. I know these guys. The teams socialize a lot. They undo the handcuffs so that one of my hands is free while the other is handcuffed to my ankle. Then I'm told that I have to feel each of their cocks and guess who the player is. Every time I guess wrong I have to give that person a blow job."

Ashley went quiet, as the fantasy began to get her wet. With a noticeable struggle in her voice, she forced herself to continue.

"I... I guessed four wrong. Four blow jobs. They don't make me swallow. They pull out before they cum, and make sure my face and tits get coated in cum. Once the last guy blew his load on me, I hear somebody else walking onto the court. They stand me up and then bend me over at the waist. They ask me if I want to go. I hear another voice say 'no'. It's my voice again." Ashley shook her head as her breath became a little ragged.

"While I'm bent over, my free hand is cuffed to my ankles. Suddenly..... suddenly I feel something slide into me. It's hard. Very hard. I almost jump, but I can't go anywhere. Whoever it is, pushed in a little, then pulls out. Then in again, a little further this time. This continues over and over until they're deep inside of me. I know everyone's watching as this stranger does me from behind. It's not long before I climax, As I do, one of the guys steps forward and removed the blindfold. Looking between my legs, I see a pair of women's legs. In our team uniform."

Ashley looked at Jennifer. "That's when I realize that it's my team captain, with a strap-on."

Ashley almost said more, but she mentally blocked out the final part of her fantasy. 'That would have to wait for another time,' she thought. " So," Ashley finished, "That's my fantasy. My dirtiest, most twisted sexual fantasy. My team captain does me with a strap-on while the guy's team watches after I've given some of them a blow-job. All because I wasn't good enough to make first string." Raising her head a little in defiance, Ashley dared Jennifer to only give her two points for that...

Jennifer waits to see if Ashley was going to say anything else. Her woman's intuition told her there's more. Probably much more. She decided not to push Ashley anymore. She thought about scoring a four, but the crowd might get riled if she didn't give Ashley five points for a story that hot. Looking at Ashley she holds up 5 fingers.

Jennifer 38, Ashley 43

Ashley sighed and leaned back as a wave of relief drowned out her concerns. She was only a handful of points away from victory. But Jennifer lost points earlier. That could happen to her. She scrutinized the phone, and said: "okay Jen, let's see what you're up for next."

Jennifer picked up the phone. Tapped the screen, and read out loud "Describe your first self-service experience"

Jennifer smiled and began to speak in a deep sultry voice, "I had just gotten my driver's license. I asked my dad to borrow the convertible he got for his 50th. He said yes, so I picked up a few of my girlfriends and we drove down to the beach. We cruised around the beach checking out the hot guys. We catcalled every sexy stud, hot surfers, muscular lifeguards, and cute frat boy we saw. On the way home the gas warning light came on, so I pulled into a gas station. When I got to the pump, there was a sign saying 'self-service'. I'd never pumped gas before, but I put $8 worth of fuel into the car, all by myself." She ended the story with laughter in her voice and a twinkle in her eye. When she stopped, she nonchalantly sipped a drink and waited for everyone's reaction.

Ashley opened her mouth to say something, but no words came out. She closed her mouth again and then raised a finger as if to ask a question. Her brain processed what Jennifer had said and her finger fell. Opening her mouth again, she only managed "Ahh...." this time, before a smile started to crease her lip. Breaking into a full grin, Ashley realized what Jennifer had done. She started laughing at her friend's out-of-the-box thinking. Clapping her hands, she looked at Jennifer, amused. Glancing around the audience, she saw several others laughing. After all the sexual tension of the past few dares, it felt good to get some humor into things. Ashley had to concede it was clever, even if it wasn't what the phone was suggesting.

"Okay, okay," Ashley said, finally. "Not bad, not bad. It sounds like you didn't score, so I'm taking away some points, but since you had the wits to say that, you get four points." Ashley raised an open palm to signal she wasn't quite done speaking. "But.... next time the phone asks for a story, I'll be wanting a few more dirty details than that!" she finished, with a smile.

Jennifer 42, Ashley 43

Jennifer taps the phone and reads the dare. She starts laughing hard and hands the phone to Ashley saying "I guess my nudity is making you lose a turn hun."

Ashley looks at the phone and reads "Get behind Jennifer and put your hands in her pockets."

"No pockets on a naked chick. So you can't do it" She realizes this is her chance to catch up and win the game.

Ashley considered a liberal interpretation of pockets. She was certain she could find something on Jennifer to insert a couple of fingers into. She conceded that Jennifer had forfeited a turn, so it was only fair that she pass on one.

With only a halfhearted grumble, Ashley indicated that Jennifer should take her turn. She tapped the phone and read "Ashley is your mom. She caught you in bed with someone of the same sex. Explain yourself."

Jennifer froze not sure how well this would go over in this crowd. She had no idea how a normal household worked. Hers was far from normal. She decided to admit what happened when her mom caught her in bed with her first female lover.

Ashley read the dare and realized she had a small role to play in this. Jumping to her feet, she knocked twice on the bar top, as if it was a door, and then took a step towards Jennifer. Putting on her best "shocked mother" expression, Ashley gasped in horror at the vision in front of her. "Jennifer!" she exclaimed, "what on earth are doing with that woman?!"

Jennifer looked a little scared and she had shrunk into herself a bit. Unconsciously she covered herself with her arms as she visibly swallowed. She replied, "The same thing I saw you and Grandma doing with Aunt Sally last week. If you want to eat your daughter's pussy then start licking. Otherwise, shut the fuck up and let me fuck my sister." Her face turned red and she looked around at the crowd to see how they would react.

For the second time in as many dares, Jennifer managed to render Ashley speechless. As Ashley's eyes opened wide, she felt the entire audience do one massive intake of breath.

A slow clap started from the back of the crowd. It was one person for several seconds then two. The clapping began to grow, and without even Ashley found herself clapping. The applause built into an ovation, Ashley tried to read Jennifer's face and saw fear and shame.

When the applause died, Ashley simpered, "Well, I can hardly give you any less than five for that, can I?"

Jennifer 47, Ashley 43

Damn it. The pressure was on her now. Less than a five would pretty much guarantee a loss for Ashley. That would mean she would be Jenifer's plaything for the next twelve hours.

Jennifer felt relieved that the crowd reacted so positively. There were things from that part of her life she had never discussed with anyone, even her boyfriend. She glanced at Mike and saw a look of shock on his face. He wasn't moving. He stood there and stared at Jennifer. Jennifer hung her head in shame, hoping that her revelation didn't screw up her life, again. God knows how many people are uploading her antics to Porn Hub. Taking a drink to calm her nerves, she handed Ashley the phone. She hoped she wouldn't have to participate so she could stop being the center of attention for a few minutes.

Command Jennifer to suck you. You tell her where. Ashley read. She looked over at Jennifer and put a hand on her shoulder. They held a whispered conversation, as everyone watched, wondering what was going on. Then they both stood up and they hugged. They stood there hugging for several minutes. When they separated, those closest could see that Jennifer had been crying. Mike walked over when the ladies separated. He took Jennifer's hand in his and held it for a moment while they stared into each other's eyes. When Mike let go of Jennifer she stood straighter, and her smile she returned. She ran her fingers through her hair and let out a big sigh.

Ashley watched her friend go from a distraught and scared girl, back to the confident easy-going woman she knew. After Mike walked away, she asked softly, "Game on?"

Jennifer took a sip of a drink and replied: "Unless you want to give up and declare me the winner."

Ashley smiled at the response and said, "Hell to the fuck no!" as she ran through her options. The most obvious choice was her pussy, but Jennifer had already had a go at Ashley's clit. Ashley worried that the unoriginal idea might cost her points. As she sorted through her options, half a dozen different futures flashed before her eyes. Ashley was suddenly struck by a burst of inspiration. Sitting down, she pointed at her feet. "Jennifer, suck on my toes!" she ordered. She hoped this was the right decision. Anything less than a five here, and she would most likely lose.

Jennifer dropped to her knees. She lifted Ashley's right foot, and took the big toe in her mouth and sucked on it like it was a small cock. Then one by one she took each toe in her mouth and sucked each one. After each toe had spent some time in her mouth, she took all five into her mouth, sucking and slobbering on them. Her swirled around and between each one.

Once she finished with the right foot, she started on the left, making sure every toe got her attention. After she finished with the toes, she kissed the bottom of each foot on three spots; the heel, the arch, and the ball. Once she had kissed both feet, she stood up and downed a shot.

Ashley smiled at the response and said, "Hell to the fuck no!" as she ran through her options. The most obvious choice was her pussy, but Jennifer had already had a go at Ashley's clit. Ashley worried that the unoriginal idea might cost her points. As she sorted through her options, half a dozen different futures flashed before her eyes. Ashley was suddenly struck by a burst of inspiration. Sitting down, she pointed at her feet. "Jennifer, suck on my toes!" she ordered. She hoped this was the right decision. Anything less than a five here, and she would most likely lose.

Jennifer dropped to her knees. She lifted Ashley's right foot, and took the big toe in her mouth and sucked on it like it was a small cock. Then one by one she took each toe in her mouth and sucked each one. After each toe had spent some time in her mouth, she took all five into her mouth, sucking and slobbering on them. Her swirled around and between each one.

Once she finished with the right foot, she started on the left, making sure every toe got her attention. After she finished with the toes, she kissed the bottom of each foot on three spots; the heel, the arch, and the ball. Once she had kissed both feet, she stood up and downed a shot.

When she finished her drink, she looked at Ashley. "We're getting close to the end here, and we may not score each other fairly. How about we let Mike pick a few judges to score us on the last few dares?"

Ashley nodded in agreement. At Jennifer's suggestion. As Mike began to select five people to be judges, the ladies used the break to make another visit to the restroom. Surprisingly, they didn't say a word as they took care of business before returning to the bar. When they got back there was a table with five people sitting off to the side. Mike walked up to the competitors and told them, "You need to do your dares where the judges can see clearly." both ladies nodded, and returned to their seats.

"For the last dare, Mike intones to the crowd, Judges your scores please..."

The first judge holds up 5 fingers. The second judge holds up four fingers. The third judge holds up four, the fourth judge holds up four, the final judge holds up 3. "So the average score is four.

Jennifer 47, Ashley 47

"Only three points," Jennifer whispered to herself. She reached out and hit the screen of the phone for what she hoped would be the last time that night. Describe your pubic hairstyle in one word.

Turning to the judges, she spread her legs wide and looked down "Hmm I guess that one word would be...Bald." She ran her hands over her smooth mons, and let her finger slip between her lips, rubbing herself. She hoped the judges would give her three points for her brazen display.

Ashley felt her shoulders droop as Jennifer completed the dare. She doubted Jennifer would score less than three for rubbing her pussy. Her only hope and it was a faint hope was that the crowd's appetite needed something more depraved than a quick rub. After all that happened, having the contest end that way would be anticlimactic.

Ashley decided to try and sway the judge's votes. "Anything more than three points and this game is over!" She exclaimed to Jennifer, "And I was hoping for at least one more challenge. I've been having a lot of fun."

Jennifer looked at her friend knowing exactly what she was doing. Mike was conferring with the judges, making their votes secret. Everyone is staring at the group, waiting for the score.

Soon Mike strolled back to the bar. Beaming at the ladies who had increased his tips exponentially, he placed a friendly hand on them.

"Ladies, it is with great pleasure that I get to announce a winner..."

Ashley closed her eyes tightly, barely able to listen to what was going to come next.

"The winner... of tonight's astonishing game... is..."

Ashley groaned as she waited for Jennifer's name to announced. Sure, she'd have an hour with Jennifer. But she knew that anything she did to Jennifer would be paid back a thousand times over. She'd never been "owned" by anyone before, and she could feel herself getting wet all over again. How many times could one woman orgasm in a night?

"... the winner is...... our audience!" Mike shouted, the words slightly masked by his laughing.

Ashley's eyes shot open.

"Jennifer," Mike said smoothly, "I'm sorry to say that due to the simplicity of your dare, you were only awarded two points."

Jennifer 49, Ashley 47

49! Ashley thought that puts Jennifer at 49 points. Ashley would only need to score three points to win! She could breathe again! Her fighting spirit felt like it had received a massive shot of adrenaline. With a smile plastered on her face, Ashley knew she'd have to pull out all the stops to get three points from this crowd. Masking her concern that the judges would keep giving minimal scores to prolong the game, she said, "Okay Jen, let's hear what I get to do to win you for twelve hours..."

Jennifer growled under her breath. Ashley reached for the phone and tapped the screen for her next, and hopefully last dare. Invent a new sex position. Give it a name, and demonstrate it with someone.

Ashley inhaled as the challenge was read. The trials and tribulations of the night were beginning to take their toll. She struggled to come up with something new that would get her over that finish line. Slowly rising from her seat, Ashley looked uncertainly at Jennifer for a moment. She had no real idea what she was doing, but desperation pushed her on anyway. Then, something she hoped was inspiration arrived. Inspiration, or just some random thought floating through her mind, only time would tell which. She walked over to a man sitting nearby and stripped him of his tie. Returning to her barstool she turned and asked him to come up and join her at the bar. She wasn't certain, but after all, she'd been through tonight, she wasn't going to let modesty get in the way of victory.

Slipping out of her clothes, Ashley put them on the bar and ran a hand through her hair. Looking at the man, she decided to hand him the tie. Then, Ashley positioned the bar stool in front of the judges. Sighing to herself, she then positioned herself with her ass pointing at the judges. She closed her eyes and bent over the barstool. Then she pushed her arms under the barstool so they came out between her legs.