Way Past Wild

David was very uncertain about how this was going to go. Olivia led him by the hand out of the living room where the rest of the group was, and she led him into the guest bedroom, where she closed and locked the door.

“Don’t want anyone interrupting.” Olivia blushed lightly, and she turned to face David.

Thanks to Evan’s dare, Olivia had already discarded her shirt, reducing her to just a white bra and some gray cotton shorts.

David, too, was without a shirt, and his bare, skinny chest was exposed and frankly, a little chilly.

“R-right.” David stumbled a little saying even just a single word. He’d always thought when he finally went off with a girl to do something sexual, things would just click naturally. They’d just kind of crash together and everything would be blissful.

Like with Rachel, in the shower back at the beach. That had been insane, but it had felt so… natural. Maybe that was just Rachel’s experience? David didn’t know how much experience Olivia had, but it certainly wasn’t the amount Rachel had.

Olivia cleared her throat. She gave David a warm smile.

“I don’t know why I’m so nervous.” Olivia laughed, and her fingers fidgeted with her glasses a little, “This isn’t the first time I’ve done this. You’d be surprised how many guys ask me to do this.”

David laughed.

“No, I wouldn’t. Your tits are amazing. There’s a reason your titjob was the prize.” David said enthusiastically. Olivia looked touched.

“Do you think so?” she asked.

“Uh, absolutely!” David exclaimed, shocked, “Have you really never noticed how incredible they are?”

“I mean.. I don’t know about incredible. They’re big, sure, but I mean, I kind of always thought they were too big. Growing up, a lot of girls told me they were too big, too.” Olivia explained.

“They were just jealous of how amazing you are.” David blurted, and Olivia beamed at David.

“You’re such a sweetheart.” she told him lovingly. Then she reached up to the clasp of her bra, which was on the front, and she undid it. The white bra fell to the floor, unveiling Olivia’s enormous, flawless tits.

“Wow.” David revered them. He’d groped them for a considerable length of time earlier, but he’d been blind to how amazing they were. Now, there they were, in all their glory… and he was about to fuck them.

As Olivia watched David practically drool over her tits, she began to really believe him when he said he loved her tits. The adoration on his face was impossible to fake.

“Your turn to undress.” Olivia reminded her former charge with a giggle, and David nodded, quickly stripping out of his shorts and boxers. When David’s boxers came down, though, Olivia gasped.

His cock was huge! It was so long, and thick, and… Olivia was transfixed by the huge, rock hard cock before her. She looked up at David, and found he actually looked a little shy.

“What’s wrong, honey?” Olivia asked, drawing closer to cup his cheek. David’s huge cock poked her in the thigh as she did so.

“I know I’m kind of a freak.” David said weakly, “A dick this big… it’s not normal.”

“Oh, it’s absolutely not normal.” Olivia soothed him, “But it’s wonderful. You just complimented my tits for being amazing… now it’s my turn. Your cock is amazing.”

David looked at her in surprise, and then he impulsively leaned in and kissed her. Olivia gasped in surprise against his lips, and then she pulled the boy close to her. David’s hard cock slid between her thighs and her bare enormous tits mashed against his chest.

David could feel Olivia’s hard nipples dragging across his chest. He could feel her incredible melons mashed against his chest.

Olivia soon drew back, slightly flushed and giggling.

“That was not part of the dare.” she admonished him lightly, and she stepped back, getting down on her knees. David barely heard the admonishment, too quickly distracted by Olivia getting down on her knees.

Olivia cupped her tits with her hands, and then she leaned forwards and slid her enormous tits around his huge cock. David gasped at the heavenly feeling, and Olivia smiled at his obvious enjoyment.

“Congrats on winning the competition.” Olivia beamed at him, and David grinned happily as he started thrusting his hips, fucking Olivia’s tits.

His cock tip kept hitting her face as he thrusted, David noticed, but he didn’t plan on stopping. Olivia kept her tits wrapped around his cock and she squeezed and rubbed them all over while he fucked her bosom.

“Like that?” Olivia panted, flushing as David’s cock hit her in the cheek.

David nodded eagerly.

“Yes! Yes, it’s amazing!” David grunted, making Olivia smile. Then David’s cock hit her in the lips and the tip slid inside her mouth. She let out a sound of shock, but her open, surprised mouth was a prime target for the next thrust, so David pulled back and thrust deeper. His eyes were closed, he had no idea, but the thrust pushed his cock right into Olivia’s mouth. She sucked dutifully on his cock, making David groan.

The second biggest tits David had ever seen in his life were wrapped around his cock, and he had the first few inches of his cock inside his babysitter’s mouth. What a prize, damn.

David pulled his cock out of Olivia’s mouth, and he could have sworn she looked disappointed.

Olivia hesitated as David kept fucking her tits, then she looked up at him, her pretty green eyes meeting his eyes.

“Do you want to just keep fucking my boobs… or did you want to fuck my face?” Olivia whispered, too horny to not say it, but a little too embarrassed about asking a boy she’d used to babysit to fuck her face.

David’s mouth fell open, then he grinned.

“I’d happily fuck your face.” David said instantly.

Olivia stared at David’s huge cock and opened her mouth wide. This was going to be a tough job. David put his hands on Olivia’s shoulders, and she put her hands on his thighs as he lined up his cock with her open mouth.

David hesitated so long Olivia thought he might be getting cold feet.

“Do it-” she started to say, but then she abruptly had a cock in her mouth and she choked on her words.

David eagerly thrust into Olivia’s open mouth, and she took it shockingly well. She gagged a lot at first, until David figured out how he was meant to be doing this, and then they both seemed to get the hang of it together. Olivia’s tongue ran along the underside of his cock, an area that was super sensitive for David.

He groaned and his hips bucked, shoving more cock into Olivia’s mouth.

“Fuck, this feels awesome.” David groaned.

Olivia wanted to say she was happy about that, but couldn’t. David’s hands reached down to grab her tits and he squeezed them tightly while she blew him.

Olivia’s tits were very sensitive, and she adored having his hands all over them, and it was making her even hornier. David’s cock between her tits had already left her a soaked mess in her panties, and now even more love was being shown to her enormous, sensitive melons.

“How’s it going?” the door opened to reveal a very naked Danielle Holland, who gasped when she saw the scene before her. But not a gasp of shock or disgust. More a gasp of excitement.

“David Johnson! I’m so proud of you.” Danielle laughed, coming into the room.

“H-huh?” David asked, his eyes locked on the naked blonde MILF. Why was she naked? How did she look so heavenly naked? These were just some of the questions running through his mind. Danielle came over to his side, and she looked down with him at Olivia on her knees sucking his cock.

“I don’t recall your cock in her mouth being part of the prize.” Danielle explained, “I see you talked her into more.”

Danielle’s bare, curvy body so close to David was making it ridiculously hard to think, and Olivia’s head bobbing on his cock wasn’t helping matters.

“Uh, yeah, I guess so.” David said, and he reached out to grab Danielle’s waist on impulse, a strong burning desire inside him. Danielle’s eyes lit up, and she gave him a playful smile.

“Look at you being all bold.” Danielle said encouragingly, “What are you going to do to me, stud?”

“I…” David found his brain stalling a bit, so all he could think of was pulling Danielle close, and so he did. Her bare tits squashed against his chest, he felt her hot pussy against his thigh, and her full lips curved into a smile. Danielle laughed as she was tugged against the skinny teenaged boy. She cupped his cheeks and smiled at him.

“I don’t know what training Rachel’s been giving you, but she’s right, it really is transforming you.” Danielle told him happily.

David nodded slowly, and Danielle was stunned at the hunger in his eyes. David put a hand on the back of her head, and Dani’s eyes widened as the boy pulled her down into a fierce kiss.

David kissed the married woman fiercely, making Danielle groan into his mouth. His hands wrapped tightly around her, and he pulled her voluptuous body closer, those very large tits pressing against his chest, and now the hot pussy pressed against his thigh was very obviously wet. David had Danielle Holland’s pussy juices running down his leg. Holy shit. Olivia felt his cock throbbing in her mouth, and she knew just how aroused David was right now.

David pulled his cock from Olivia’s mouth, trying to prevent the inevitable, but as he tightened his grip on Danielle’s naked ass, he knew he was going to cum whether in Olivia’s mouth or not.

Olivia didn’t help matters either, when she lifted her tits in her hands and wrapped them around David’s cock again. Her soft, enormous pillows squashed around David’s cock this time, and he grunted at the feeling of fucking Olivia’s tits.

Meanwhile, his lips were still mashed firmly to Danielle’s, and her pussy was truly gushing now. Danielle was stunned herself at how wet she was. She hadn’t been this wet since- no, don’t think about Jace. Not now. He was her son.

If it took David to forget about her depraved, incestuous thoughts, then she would happily throw herself into David’s embrace. She couldn’t do that with Jace. Couldn’t cross that line.

Besides… it wasn’t like Jeremiah had made her this wet in decades. Fuck, he’d never made her THIS wet. This was her daughter’s best friend she was all over. But she just couldn’t find it in herself to be ashamed. In this moment, she felt a lot less like responsible mother Danielle, and a lot more like reckless, horny young woman Dani.

Dani looked down at David’s cock, and her eyes nearly bugged out. The skinny teen’s cock was huge! He was hung like a horse, and he was fucking Olivia’s giant rack like there was no tomorrow.

Dani watched it happen with an open, amazed mouth. She hastily licked up the drool coming from her mouth as she ogled, no, admired, no, worshipped David’s cock with her eyes. A cock that big had only come into Dani’s life once before, and he had left it, leaving Dani heartbroken, which had brought about her relationship with Jeremiah.

It being a cock this big that finally tempted Dani anyway from Jeremiah seemed almost poetic. Looking at David’s huge hard dick, it wasn’t hard to believe he was divinely placed in her path.

“You’re huge.” Dani breathed reverently, but David’s old insecurities flared, despite Rachel and Olivia’s assurances otherwise today, “I… I’m so impressed. It’s amazing. You’re amazing.”

And then to David’s shock, she attacked him with a kiss. He squeezed her MILF body tight, and kissed her back heatedly. He was on an absolute confidence high. Forget Danielle’s husband… she was all his now.

Pride burned in David’s chest, and when he did finally erupt all over Olivia, he roared into Danielle’s mouth. He could have sworn she quivered in his arms. David broke the kiss to watch his cum spray over Olivia, relishing the ropes of his seed that streaked across her pretty face, over her glasses, and then of course, all over her chest and tits.

“That’s such a big load!” Dani gasped in David’s ear, and the pride in him burned again.

“I’m covered!” Olivia gasped, looking up at David with only one of her pretty green eyes visible, the other obscured behind a cum-splattered glasses lens.

All three people in the room were panting hard. The sounds of flesh slapping had stopped, and other than their heavy breathing, the room was quiet.

Then Olivia broke the silence.

“Mrs. Holland… why are you naked?”

———

Minutes Earlier…

Jace Holland leaned against his aunt Daphne’s side while Rachel got up and spun the bottle to determine whose turn was up next. Jace had a pit of jealousy in his stomach from knowing that David was off somewhere getting Olivia Vane’s famous tits wrapped around his cock. Lucky bastard. And all because Jace couldn’t recognize his own mother’s tits!

A glance around the group showed Jayden looking elated as he had Brooklyn and Dana on either side of him, both girls leaning on him. One of Brooklyn’s bra covered tits were definitely squished against her brother’s arm, while Jayden’s other arm rested on Dana’s cleavage, and Jace found it amusing how his twin sister was practically half in Jayden’s lap.

Owen on the other hand, was seated very close to Skylar, and the two would occasionally whisper quietly, which always resulted in Owen having a dazed, horny look on his face while Skylar’s lips would twitch with a smile or a smirk.

Evan kept trying to talk to Claire to the tune of constant stubborn rejection, which made Jace chuckle.

Rachel took her seat back next to Danielle, and the two MILFs were happily chatting.

Jace caught Zoe’s eye, and the black-haired beauty winked at him, making him smile. Him and Zoe and Daisy had been a little trio growing up, united in their mutual dislike for Evan.

The bottle came slowly to a stop on Daphne, who looked pleased with the outcome of that spin.

“Right, hmmm… who should I pick on first?” Daphne grinned viciously at her big sister. Danielle smirked back at her younger sister, and wiggled her fingers in a wave.

“I dare anyone over the age of 30 to strip naked. Sorry, old ladies.” Daphne said smugly, and then she slipped an arm around Jace and cuddled up against her nephew’s chest to watch the show.

“Old ladies?” Danielle erupted, “Watch your step, Daphne. My next turn is going to be hell to pay for you.”

“Or mine.” Rachel chimed in, but with much less venom and much more wryness, and Daphne giggled wildly.

Rachel was obviously quickest to strip. She was already nude from the waist up, she just stripped out of her bottoms and her panties and sat unabashedly, even going so far as to wink at Jace and Daphne.

Danielle didn’t take much longer either, she only had the extra item of a bra to take off, and then she, too, was naked. Jace stared at his mother’s tits, the very same tits he’d just had his face mashed into.

“Get a good look now, Jace, maybe next time you’ll be able to recognize them.” Skylar teased.

“Ha ha.” Jace glared at Skylar, who grinned at him. Jace’s gaze slid back to his mother’s very large boobs, but when his eyes flicked up, they met her blue-green gaze. She was smirking slightly, and Jace knew he’d been caught.

“I’m studying. Like Sky suggested.” Jace shrugged innocently, making Rachel laugh.

“Do I have to do this?” Claire huffed.

“Yes!” Daphne, Rachel, Danielle, and Skylar chorused.

“Fine, fine, I’m doing it.” Claire muttered sourly, shooting a mutinous glare at Daphne as she stripped off her remaining clothes and sat back down naked.

“I would’ve helped.” Evan told her with a smile, visibly looking up and down her naked body.

“I’m not that old, I can undress myself.” Claire snapped back.

Her body wasn’t quite as impressive as her two best friends’, but damn if Claire wasn’t sexy as hell. Her body was slim and fit, clearly the result of excellent workout regimens. Her ass was perfectly toned, and her mile long legs drew the gaze of everyone who was into women, because Claire was one hell of a woman.

Daphne got up off Jace’s side to reach out and spin the bottle, and it came to a slow stop pointed at Jayden.

He squirmed a little from the attention he suddenly received from everyone.

“Uh… I dare anyone sitting next to a guy to kiss them. On the mouth.” Jayden flushed.

“Jay-Jay!” Brooklyn exclaimed in shock. Jayden’s eyes widened.

“Oh, cut him some slack, hon.” Danielle laughed, “He very obviously was just fishing for a dare to kiss Dana.”

“Mom!” Dana protested, cheeks reddening, but when she looked at Jayden, a small smile split her pretty face.

“Well, I guess that means pucker up.” Daphne fluttered her lashes at Jace, and then she leaned in and kissed him gently. Their lips fit nicely together, and she hummed fondly against his mouth as they kissed, slow and steady.

“Daphne!” Danielle’s sharp voice came, “Are you making out with my son?”

Daphne’s blue eyes were a little unfocused when she opened them again after kissing Jace, and she shook her head rapidly to clear it.

“What? Uh, no. It was the dare.” Daphne muttered.

“My turn!” Kayla said brightly, and then his favorite teacher was kissing him on the mouth. His hands reached up to grab her waist as their lips smashed together, tongues wrestling.

While Jace and Kayla were tongue-wrestling, Jayden was feeling very awkward sitting between the two girls he’d made this dare so that he could kiss.

Brooklyn went first, leaning in and pecking him on the lips. It was remarkably quick, but it was Jayden’s first time tasting Brooklyn’s plump, mouthwatering lips, and damn if he didn’t love it.

Jayden turned to Dana next, and her lips met his and the whole world faded away. She was warm to the touch, which was about when he realized he was cupping her cheek, but she seemed unbothered. The kiss didn’t last too long, but it was sweet and amazing. When Jayden drew back, his breathing was very unsteady, and his brown eyes met her blue-green ones. Dana smiled her pretty smile, and Jayden impulsively kissed her again.

She gently kissed him back for just a moment, before drawing away, cheeks red.

“Me next!” Owen said eagerly, and Dana turned to give Owen some sugar. Owen eagerly kissed the petite Holland girl, his arms sliding around her tightly, smushing her bra covered breasts into his chest while his hands stroked up and down her mostly bare back.

Dana’s head was tilted up to kiss him, and he kissed her hungrily, enjoying the way she seemed so soft and pliable in his arms. The way she was slumped up against his chest, his body holding her up. His tongue slid into her mouth and licked her tongue, which was apparently a step too far, because Dana yanked back.

“Owen! What the hell?” Dana flushed.

“Don’t act like you weren’t loving it.” Skylar smirked. “Besides, it’s just tongue. No biggie.”

Skylar grabbed Owen by the chin and turned his head around to kiss him fiercely. Her tongue did slide inside Owen’s mouth, and fighting it never crossed his mind. Skylar’s experienced tongue led the kiss, and Owen was just beyond glad he had the sexy Skylar Wayne’s slender, tight body pressed to his.

Skylar drew back a while later smirking.

“Now that’s how you kiss.” she smirked at Dana, who flushed. Turning to her best friend, her grin grew wickedly. "You're up next, Izzy, and I'll be watching."

"Watching what, me kiss the orc?" Izzy asked with a slight grimace. Sure, Evan was in her friend group, but the Holland girl had never felt anything that could be considered more resigned acceptance of his presence.

"Isabelle Holland, don't be so rude!" Dani gasped in mock offense. "Evan is not an orc."

"Yes I will be," Sky added with her trademark grin. "If you try anything as weak as Brooklyn, I won't forgive you. It reflects poorly on me, after all."

"Fine..." Izzy rolled her eyes and leaned over to the tall teen. "Let's just get this over with."

Evan looked to Isabelle, and didn’t bother much with her, in all honesty. Sure, she was objectively attractive, but he had never really felt anything for her either. Excitement, he loved. Rejection, he could deal with. Disgust? The thrill of the hunt! Apathy? Did nothing for him. He gave her a good kiss, but it was far from high effort.
"Good enough, I guess." Sky said begrudgingly.

Whatever, Evan thought. The real prize was to his other side. He quickly turned to face the other woman… sexy naked Claire Johnson.

“Oh hell no.” Claire said, shaking her head, which just made her naked tits jiggle, which made Evan lose focus slightly.

“Don’t be a party pooper!” Danielle cheered, and Rachel snorted.

“Kiss him, kiss him! Look, he’s a handsome teen guy, Claire, you could do a lot worse.” Rachel smirked.

“You think I’m handsome?” Evan grinned at Rachel. Rachel deliberately jiggled her tits for his hungry eyes to devour.

“Oh, I do, and you know I do.” Rachel giggled, “Danielle here thinks you’re a stud, too.”

Evan turned to Danielle, his grin growing wider.

“Don’t tell him that. The last thing he needs is an ego boost.” Danielle joked, but she winked at Evan all the same. Rachel elbowed her discreetly, and Danielle chuckled at her friend, before jiggling her tits for Evan, too. Rachel blew him a kiss, which Danielle mimicked.

“See? Your friends are certainly willing. Why aren’t you?” Evan grinned.

“Kiss one of them then.” Claire said stubbornly.

“You girls up for that?” Evan asked Rachel and Danielle.

“Not in Claire’s place.” Rachel shot finger guns at her best friend, who scowled.

“It’s just a kiss, Claire!” Danielle encouraged.

“Damn it!” Claire growled, throwing up her hands. "Is this really what you want? I'm almost 40 years old, and the mother of a son who is legally an adult, and you want me to throw myself onto a high school student?"

Dani and Rachel looked at their ranting friend.

Then they looked at each other.

Then back to their friend.

"Yep," said Dani.

"Absolutely," agreed Rachel at the same time.

Claire's eyes widened, her mouth tightened, her chest grew red with flushed, and then she finally exploded. "Fine!" she yelled, diving towards the muscled linebacker, practically tackling him. Before Evan could blink, the naked dark haired MILF grabbed him by the shoulders and kissed him hard, her weight taking her forward and knocking him onto his back. Claire's lips locked against his own, her firm tits squished against his well-defined chest. Evan reacted swiftly, kissing back and grabbing her by her bare hips. Claire kissed deeper as Evan continued to run his hands over her body and kiss back, before the older woman let out a moan of pleasure into his mouth. "Is this what you want?" she hissed at her friends as she pulled up for a second, before lowering her face back down for a second helping. "I'm making out..." she grunted, repeating the action every few moments. "With a hot... young... beast!"

"Hell yeah you are!" Rachel cheered.

Evan's hands continued to roam over the tight bodied MILF, taking in all her curves, her soft skin, her sensitive areas. He made sure to take note of which spots elicited moans, which ones caused pants, which ones created gasps. Finally, Claire pulled herself away from Evan, looking down at the young man from a position straddling his hips. Her tits moved up and down, in time with her deep breaths. Claire and Evan held eye contact for a moment more, before she pulled herself off his lap, sitting demurely as if nothing had happened. Grinning like a madman, Evan sat back up. When she didn't move as he put her arm around her, he knew that it was just the beginning.

“Well, umm, David and Olivia are taking a while.” Danielle interjected, breaking the silence. The flush look on her face was proof enough that the scene in front of her had certainly aroused the beautiful busty blonde.“I’m going to go see what’s keeping them.”

"He’s probably got her bent over something. I’m very proud of how he’s turning out.” Rachel grinned as Danielle stood up. Danielle, collecting herself, gave a disbelieving scoff, and she headed out to see where they had went off to.

“Spin the bottle, Jayden.” Skylar invited, and Jayden scooted forwards awkwardly to do just that.

The bottle spun, and the group held their breath to see who would be chosen.