Dares Gone Wild

The bottle slowly came to a stop pointing at Kayla.

“Oh! Uh, I dare everyone to tell me their first kiss.” Kayla said, and she turned to Brooklyn to start it off. Brooklyn’s cheeks reddened.

“Uh… I… I haven’t kissed anyone before.” Brooklyn confessed in a mumble. Jace’s eyes widened from the other side of Kayla. A gorgeous girl like Brooklyn hadn’t kissed anyone before?

“Oh, well, I’d like to change my dare then.” Kayla said suddenly.

“I’ll allow it.” Skylar nodded, making Kayla smile.

“Alright, so then I dare Brooklyn to have her first kiss.” Kayla said. Brooklyn’s eyes widened and she rapidly shook her head.

“C’mon, Ms. Roberts, seriously?” Brooklyn groaned, looking nervous and shy.

“Yup.” Kayla crossed her arms beneath her bra covered large tits.

“With who?” Brooklyn blushed harder.

“Your choice, honey.” Kayla said kindly.

“Here, Jace, you do it.” Dana spoke up.

“Me?” Jace asked, surprised but certainly not opposed.

“Yup, that’s a good idea.” Kayla nodded.

Brooklyn, her heavy, very large tits clad in just an orange bra, came shyly up to Jace, and Jace resolved to give the stunningly gorgeous girl an amazing first kiss. He stood up and pulled her close, her very large tits smushing against his chest as he planted his lips on hers.

Brooklyn gave a kind of groan into his lips, and her arms around his neck tightened.

Jace’s mouth was hot on hers, Brooklyn realized happily, and she loved the way his hands felt wrapped around her. She was having the time of her life, kissing the boy she’d been crushing on for years.

Her hips felt like they were meant for his hands, and the way their bodies fit together… it was like it was destiny.

She had no desire to ever stop kissing Jace. She knew she needed air eventually, but she was determined not to stop kissing Jace until her lungs were about to go.

She felt Jace’s posture stir, and she was worried that he was pulling back, so she pushed herself closer to him, and then she felt something amazing.

A big bulge in Jace’s boxers. Pushing into her thigh. Jace wasn’t wearing any shorts, thanks to the remove a clothing item dare, and she could feel his hard cock pressing against her thigh in such detail because of it.

Was… was that her doing that? Did she really have the looks to arouse Jace Holland? THE Jace Holland? She could hardly fathom it.

Jace held Brooklyn tighter, and she moaned happily, then, completely out of instinct, she started rubbing his erection with her thighs. Brooklyn was just in jean short shorts, so her thighs were bare. She also had quite thick thighs, which she understood some guys loved, while other guys preferred skinny girls like Dana.

Brooklyn wasn’t sure which kind of guy Jace was, but as Jace’s erection was rubbed against the insides of her thick thighs, she felt it throbbing. That was a good sign, right? Right?

It was then that Jace let go of her and broke the kiss. A sad mewl escaped her lips, and she flushed at the sound of it. She certainly had not intentionally made the sound. Brooklyn hastily retreated back to her seat, head down and cheeks flushed. Rachel wolf whistled, which only made Brooklyn flush harder, while it made Jace laugh.

Jace looked around and saw cheerfulness on Dana’s face, and proudness on Danielle’s face. He chuckled at how proud his mom looked.

Kayla scooted forwards to the bottle and gave it a spin, and around it went until it landed on Rachel.

She grinned deviously.

“Alright, Dani, I presume you have some form of blindfold in this house?” Rachel asked her friend.

“I have some bandanas that you can make into a bandana.” Danielle said, confused.

“Perfect.” Rachel nodded, and then she pointed at certain people as she counted.

Jace, Evan, Jayden, Owen, David.

“I’ll be needing five.” Rachel said, and Danielle quirked a grin at her best friend as she got up to go and get them.

“So, I’ll explain the dare while Dani’s grabbing the blindfolds.” Rachel said, “All the boys are going to be blindfolded. All of us ladies are then going to take off any bras or tops they might have on. I’m looking for bare tits. Then, I’m going to randomly pick a girl and they’ll have to walk forwards and let each guy grope their tits. The guys will then have to guess which lucky lady’s tits they were just playing with. A wrong answer will eliminate them from the game, but they’ll remain blindfolded for us ladies’ decency’s sake. The winners will go into the next round and so on until there’s just one guy standing, and he wins.”

Jayden and Owen’s eyes looked like they might pop out their skulls, and David wasn’t much better. Even looked positively thrilled, and Jace was pretty excited himself.

“Is there a prize?” Evan asked with a grin.

“You’ll have to win to find out.” Rachel retorted. Danielle came back with the blindfolds, and each boy had their eyes blindfolded by Danielle.

Then Jace felt soft hands taking him by the shoulders.

“Come on, hon, this way.” his aunt murmured as she led him to a chair. He presumed the other boys were also in chairs, making a row, but he wasn’t positive.

Jace heard the bottle spinning, and then silence. Then footsteps.

David ended up being first in the row, so he was first to get to feel the magnificent pair of tits before him.

He gave the enormous pair of tits one squeeze and knew exactly who it was, but he wasn’t going to give up this opportunity!

David enjoyed caressing Olivia’s massive knockers, exploring each and every part of them, very happily. He heard heavy panting, too, familiar panting.

“Save your answer in your head.” Skylar’s voice came, “You’ll write it down at the end of the round, once the mystery woman’s tits are out of your grasps.”

David reluctantly let go of Liv’s enormous melons, and she stepped down the line, presumably.

Jayden and Jace both had the exact same immediate reactions as David.

Owen took just a beat longer, half unsure if it was Rachel, but no, it was Olivia. She was the Tits Queen.

Evan was also an immediate reaction, yet he took the longest deliberating.

All four guys, however, spent a very lengthy time inspecting those amazing tits… just making sure they weren’t wrong, you see. Throughout their thorough investigations, poor Olivia’s super-sensitive tits came back to haunt her, as the woman was a flushed mess by time she reached the second one in line, Jayden. She was panting and moaning almost with every touch, making it super obvious who it was, even if her tits hadn’t been the most easily recognizable in the room.

“Alright, blindfolds off.” Skylar’s voice came again, and the boys obeyed.

All five boys wrote down Olivia on their answer slips.

“No eliminations.” Skylar grinned.

“Blindfolds back on, studs.” Danielle chimed in.

They complied, and the bottle started spinning yet again.

Jayden wondered curiously who it would be, praying for Brooklyn.

But when the tits came to him… they were disappointingly small. Well, they weren’t small. But compared to Brooklyn’s? Yeah, they were small.

They were, however, perfectly shaped. Cute little hard nipples, an excellent perkiness. An image of petite little Dana appeared in his head, and without thinking he blurted out:

“They’re perfect.”

After everyone got a chance to feel the perfect pair of tits, Evan yet again taking the longest, the blindfolds were removed.

Glancing over, Jayden saw his best friend Owen had a dopey grin on his face.

Jayden didn’t waste time in writing down Dana, but when the others’ answers were revealed… oh no.

‘Skylar’ was written on the other four cards. Well, on three of the other cards. The fourth said ‘Skylar Fucking Wayne’.

“You think my tits are perfect?” Dana giggled, beaming at him.

“Um, actually, he thinks mine are perfect.” Skylar corrected, “They were my boobs he was feeling.”

“He associated them with me, though.” Dana argued.

“That’s true.” Rachel nodded, “The compliment goes to Dana. He clearly thought your tits weren’t perfect enough, Skylar.”

“Jerk.” Skylar glared at Jayden.

Dana, meanwhile, happily came up to Jayden’s chair, and she gave him a quick kiss on the cheek.

“I always knew I liked you.” Dana winked at her best friend’s little brother.

“Heh, yeah.” Jayden said awkwardly, “I’ve always liked you, too.”

“Out of the line.” Skylar snapped at Jayden, and to Jayden’s happiness, Dana took him by the hand and pulled him over to watch the rest of the game, right beside her. Well, if he had to be out, there were worse ways to spend the time battling the jealousy watching his friends grope the hot women in the room.

Back over in the row of blindfolded boys, the next topless girl approached the quartet. David didn’t instantly know the answer this time, but after lots of groping, he decided on an answer. He had a pretty extensive memory bank when it came to different women’s tits, especially tonight when they’d almost all been reduced to just bras, or completely topless, in Rachel’s case.

David was fairly confident that this was Kayla, and if not Kayla, it was Izzy. He just didn’t think the tits were pert enough to be Izzy’s. These were a more mature pair of melons, aged like the finest of wines.

Jace knew off the bat that this was Kayla. He’s had these tits smushed against his chest for a hug far too often to not know this.

Owen didn’t take too long to deliberate for once, as he’d drooled over the sexy Ms. Roberts for a long time.

Evan used his usual lengthiest time groping and exploring the mystery tits, and he too landed on Kayla.

All four boys wrote out their answers and were declared correct by Skylar. She was still shooting glares at Jayden. She wasn’t offended, but she was just shocked that someone like Jayden would insult her tits. The insult wasn’t the problem, it was the source.

But Jayden seemed happy enough sitting between Dana and Brooklyn. Dana had her hand resting on Jayden’s thigh, and Brooklyn’s head was leaned on her brother’s shoulder.

Jace grinned at Kayla, and his teacher gave him a warm smile, clearly happy for him. He’d loved feeling her tits, but seated beside Kayla, his aunt didn’t look too happy.

“Alright, blindfolds back on!” Skylar clapped her hands together.

The next pair of tits was immediately familiar to David, and he squeezed them tightly, trying to elicit a sound from the woman who he knew these tits belonged to. This was the one and only time he’d ever be able to play with this woman’s tits, because he had the perfect excuse of deniability. These were his mom’s tits, after all.

David really got in there, using his hands to roughly grope the large tits before him. David felt his mother’s nipples hardening, and he pinched and tugged on them, still feigning that he was investigating.

He wondered if he was fooling anyone. He also wondered whether his mom looked aroused or not. He was really going all in, after all.

“Alright, time.” Skylar’s voice laughed, sounding very amused, “Damn, and I thought Evan took forever with these guesses.”

“We have a time limit?” Evan asked in surprise.

“Yup. That’s how long David here’s been playing with- um, whoever’s tits these are.” Skylar nearly slipped but recovered before she did.

Owen’s turn next, and to be totally honest… he had no idea. This wasn’t someone who he’d really lusted over, he was pretty sure, or he hoped he’d know instantly. He was trying to run through a list of who all was at this game night, but his mind wasn’t coming up with good candidates. Fuck.

Maybe he could try to pull what Jayden did, compliment the tits and then guess a girl who’d be likely to reward him for his kindness. He had no idea what else to do, and that had landed Jayden squarely in Dana’s good books, so he may as well try a similar strategy.

The only question was… who’d react similarly to Dana? Skylar? No, she’d already been up.

Ugh. Owen was too busy stressing about this that he frankly stopped trying to identify the girl from their tits and just let her go down the line, no clue who it could be.

Owen just silently resolved to guess Izzy, but then he realized furiously he hadn’t planted the compliment! Too late to do it now. Fuck.

But then, to his surprise, he felt tits press against his neck from behind, and then Skylar’s husky whisper in his ear.

“Owen, darling, you look stumped.” she breathed, making Owen shiver, “Did this round finally beat you? Poor thing. That means no more tits for you to feel up.”

Owen hung his head sadly, but Skylar patted his cheek.

“Oh, cheer up. The game’s still afoot, and I don’t see it slowing down any time soon. There’ll be plenty of fun times to come.” Skylar grinned, and she nipped at his earlobe. Again. She’d done that back during the hugging dare, too. Was that her thing? A sign of affection?

Jace and Evan finished their turns, and all four boys wrote down an answer.

Jace, David, and Evan came up with Claire.

Owen wrote Izzy. Damn. He’d totally forgotten Claire was here, her name had never even crossed his mind.

“Ooh, eliminated.” Skylar smirked, and she took Owen by the wrist and pulled him over to rejoin the circle of women.

Owen saw bitterly that Brooklyn and Dana were both leaning all over Jayden, so Owen didn’t bother sitting by his friend, he just went straight to Liv.

“You did great.” Olivia consoled him, which was slightly absurd considering the kind of competition he’d lost, but Owen accepted the consolation, and when Olivia held out her arms, Owen happily sat down in her lap and let him wrap her arms around him and push her F cup tits into his back. He loved his big sister.

“And then there were three.” Skylar clapped her hands together, and motioned for them to put their blindfolds back on. The bottle was spun, and the next girl approached the trio.

“There can’t be any repeats, right?” Evan wondered.

“Like we’d tell you that.” Rachel’s smirking voice came.

Jace waited impatiently as David had his turn with whoever it was up next. Very impatiently. He was glad he wasn’t in Evan’s position at the end of the row, he couldn’t imagine how torturous that wait must be.

The mystery girl finally approached Jace, and he eagerly reached out to find her tits. His hands closed around two tits that straddled the line between large and very large. He knew nearly instantly that this was Izzy’s tits, and he wasted no time in squeezing his cousin’s plump tits. He didn’t use much ****, he caressed the flawless bosom gently, as he knew Izzy preferred gentler touches.

He was her cousin, after all. They’d experimented a little bit back at the start of high school, and she’d always complained when he got too excitable.

So gently, he stroked and played with Izzy’s generous boobs. He heard his sexy cousin’s familiar gasp, a quickly stifled one, but it just made him smile, a smile that gave him away but he couldn’t resist.

From off to the left, Jace heard Skylar laughing. Izzy moved on quickly after that, after Jace gave Izzy’s tits a few more loving rubs. She bumped a hip against his side as she went, though, making him grin wider.

Evan’s turn finished a little after that, and then the three boys all wrote out their answers.

Shockingly, Evan had finally gotten one wrong. He’d guessed Brooklyn.

Jace and David had both gotten Isabelle correct.

“Alright, this could be our last round here.” Skylar rubbed her hands together with a malevolent smile on her face. A grumpy Evan got out of his seat and returned to his seat beside Claire, but Dana was still over by Jayden, not on Evan’s other side like she had been.

“You’ll need an impossible one to trip up either of us.” Jace boasted, and David chuckled weakly.

“David does seem to be quite the bosom aficionado.” Rachel winked at the brown-haired boy, making him flush.

“He really knows his stuff.” Danielle agreed with a giggle.

“Blindfolds on.” Skylar ordered, pointing a finger at each one of the boys left. They obeyed, and waited in anticipation for what the finale would be.

Jace heard the sound of metal on the floor, but small metal. Had Skylar flipped a coin or something?

“Seems as if you’re very gifted with determine tits by your hands.. so maybe you don’t get to use those this time.” Rachel said sweetly from behind the boys, and then Jace felt his mother’s hands grab his wrists and tie them together behind the chair.

David, meanwhile, had Rachel’s huge naked tits mashed against the back of his head as she tied his hands together.

“What are we using, then?” David worried.

In answer, a pair of tits got shoved in his face.

“Attagirl!” Skylar laughed.

Jace strained his ears to try and listen. What was happening? David, meanwhile, was having a good time.

His face was buried in a lovely pair of tits. They were big and pillowy, smushing against his face like, well, a pillow. David chanced a lick, but a hand swatted him in the back of the head.

“No mouth.” Skylar ordered, but her voice didn’t come from behind him.

This actually wasn’t nearly as easy as using his hands. With hands, David could measure size with his hands and compare it to the vivid mental images he had of each present woman’s tits. With his face buried in the woman’s cleavage, he had a much less accurate idea about size.

David turned his face back and forth, using his head as a unit of measurement. David wasn’t positive, but he was pretty sure he had his face buried in Danielle Holland’s amazing tits.

He was confident enough to guess her, so when Skylar announced time up, David felt fairly good about his chances.

Well, his chances at getting it right. He didn’t think Jace would get this wrong, as it was his mom’s tits, after all.

Jace was unsure what awaited him this round, as he wasn’t groping this round, he was just going to be put through some unkno- his thoughts cut out abruptly when a pair of tits smashed into his face. Jace jerked in surprise as suddenly he had two really big boobs wrapped around his face.

Jace knew what Skylar had said during David’s turn, but he unabashedly licked the mystery woman’s tits, once, twice, three times, before someone swatted the back of his head.

“No mouth.” Skylar’s order came again.

Fine. Jace tried to pull his face from the deep cleavage so he could push his face directly into one of the woman’s tits, but a hand pushed his face back into the deep valley.

Without much to do in terms of analysis, Jace just enjoyed having his face buried between two beautiful tits, and motorboated them, getting a few giggles from around the room. They felt big, really big. Not quite Olivia big, more like Daphne big, or Brooklyn big. Maybe Danielle big.

Too soon, his turn was over, and while it had surely been enjoyable, he just wasn’t positive. His brain was set on Daphne, for some reason, so he decided to trust his gut.

When the amazing pair of tits withdrew, a few moments passed before Skylar gave the all clear. The boys’ hands were untied, and they pulled off their blindfolds.

Skylar stood between them, hands on her hips, a smirk on her face.

“So. On three, say who you think it was.” Skylar said, then slowly and dramatically counted to three.

“Mrs. Holland.” David said.

“Aunt Daphne.” Jace said at the exact same time.

“Ooh, embarrassing! It was the sensational Mrs. Holland. Your mom, Jace, not your aunt.” Skylar laughed.

Daphne was laughing, while Danielle looked rather offended.

“David recognized not just my boobs, but his own mother’s. Maybe I should adopt David.” Danielle shook her head, feigning insult.

“Sorry! It was really hard to gauge who it was just from having my face in your cleavage.” Jace shrugged, then realized that was an absolutely crazy thing to say to his own mother, but she didn’t even react.

“Well, I’m still disappointed in you.” Danielle clicked her tongue, laughing.

“So… I won?” David asked.

“Oh, yes.” Danielle told David, smiling, “You, unlike my son, got every guess perfect.”

“Hey!”

“No hey. You lost on your own mother.” Rachel laughed.

“So, what’s the prize?” David asked eagerly.

Skylar smirked.

“You get to pick one lovely lady of your choice to take you into the next room and wrap her tits around your cock.” Skylar smirked. David’s eyes widened, and his mouth fell open.

“We all agreed.” Rachel nodded, “Anyone you pick is willing.”

David’s gaze turned incredulously to Brooklyn, and she turned red and wouldn’t meet his gaze. Dana turned red, but she did hold his gaze. But David’s gaze moved to Olivia, and he knew exactly who he was going to pick.

“Olivia, huh? Shocking.” Skylar said dryly.

Olivia looked surprised to be the one chosen, but like Rachel had said, she willingly got to her feet and approached David with a smile.

“Time for your prize, then.” she said warmly, and led her former charge out of the room by the hand.

Everyone (minus Olivia and David) reformed the circle, and Rachel spun the bottle.