An Unlikely Holiday Pairing: Pt. 02

She walked up, one foot ahead of the other before she reached the edge of the bed. She leaned over Oliver, seeing that he was comfortably situated closer to the center of the bed.

"Yeah... earlier would've been better," Oliver chuckled, turning his head to the girl and feeling a sense of longing for her to get in now. "I'm pretty tired, Madi... want your turn now? You just might win..."

Madi smirked and turned her head sideways at him. "Oh, so you were serious about wrestling with me, huh?"

Her eyes studied his body, only the young man's upper body being visible to her. As shirtless as he was last night, she could now see him clearly with the aid of the lights of his room. Her gaze lingered a bit too long, causing Oliver to take notice.

"If you're looking for any bruises, you won't find any," he teased.

Madi pressed her knee into the bed and climbed on top, kneeling into the bedding while staring down at her step-brother. She gently peeled back his covers, revealing his lower body until his bare thighs came into view, just past his mild crotch bulge. She rolled her eyes and let go, slipping back a bit and crossing her arms.

"You know, I thought that you'd maybe put some clothes on since we'd be sharing a bed again," she said.

"I am wearing clothes... boxers."

"Something else... maybe?"

Oliver thought about it for a moment. His eyes went to the ceiling and then back down as he locked eyes with Madi again. "Are you wearing panties?"

"Ollie...?" Madi questioned as she started to blush, raising an eyebrow at him.

"Well, are you, or would you prefer that I checked you?"

She gave him a half-smile, realizing that Oliver wanted to return the favor.

"Ugh... no, you don't get to check, and yes, of course I'm wearing panties, Oliver. W-Why...?" Madi inquired, a little taken aback, but also growing more curious with each passing second.

Oliver gingerly sat up in bed, back against the headboard. "Okay, how about this... since you're pretty sure that you'll pin me if we wrestle, how about if you win, I'll put clothes on to bed for the next few days that you're sleeping here."

"And...?" Madi asked with a healthy skepticism in her voice before continuing, "if I lose?"

"If you lose, then... you can only come to bed in your underwear," Oliver declared, smirking at her.

Feeling a mixture of embarrassment, growing excitement, but also feeling an opportunity to test her mother's advice about just acting natural without any inhibitions, she readily agreed. "You're on, Ollie, but don't cry when you lose."

Oliver coughed and pressed his hand up into his chest, massaging himself. "Ouch, don't make me laugh, Madi. Let's raise the stakes a little... if I win, I get to strip you."

Madi started to giggle nervously, scooting back on the bed while still kneeling near Oliver. The sudden image of her step-brother stripping her down to her underwear before she was allowed into bed flashed in her head, an image that she quickly disposed of as the escalation made her feel a little hot under the collar.

"Strip me? Ollie... no way..." she protested, letting her soft eyes tease him. She scanned his body again, his muscles still reflecting the dedication of a young man who prided himself on his physical well-being.

"Come on... what's it matter? You're going to win anyway," Oliver admitted. "If you want, I'll even sleep on the floor if you win so you can have my bed to yourself... just like you wanted last night."

Madi put her hand up to her face, covering her mouth with the webbing between her thumb and index finger. She bit down gently while tipping her head down, and glared at Oliver. He had given her plenty to consider now, leading her to try and decide if she should agree or cancel the entire wrestling idea. Despite knowing it to be risky, no part of her wanted to forgo this now. Her attraction to Oliver now proved to be undeniable and her hesitation conveyed her interest to him. Whether it was a romantic attraction, lustful needs, or just enjoying his company, she had never felt this close to him despite having lived with him for over a decade now. The feeling of excitement caused her heart to beat a bit faster, convincing her to stay the course.

"Fine, Ollie. If you somehow miraculously win, then yes, you get to strip me too," she scoffed again, hardly believing it anyway. "But before I beat you, I need to use the bathroom. Don't go anywhere."

She backed up and slid off of the bed, spinning around to head into Oliver's bathroom. He turned slightly onto his side, watching her figure disappear before the door closed. Oliver's lust and feelings for Madi had significantly shifted from the morning. He couldn't explain what it was about her, but throughout the day, it had dawned on him that his failure to truly connect with any of his ex-girlfriends in the past were due to Madi. None of them were her. None of them could ever be her. None of them had that perfect combination of beauty and sass and everything in between that made her so special to him. He resolved to just act natural with her to see where things would go and the fact that her own demeanor towards him had changed so dramatically since last night only encouraged him to pursue this, to pursue her.

"Well, this should be fun," Oliver said to himself, chuckling as he shot up out of bed with ease. "Too bad for Madi that Uncle Tyler overate at dinner and only threw me around a bit before he passed up on wrestling me today."

Madi stayed seated on the toilet, pants and panties around her ankles, barely making a peep. Having spent the first minute or so adjusting her hair and giving herself a pep talk in the mirror, she only just sat down for business. Crouched over, her elbow dug into her thigh as she propped her head up in wait.

Her eyes shot over to the doorknob, noticing that it was turning. "Huh?"

Oliver opened the door and walked inside, sporting a casual attitude as he stopped and glanced at Madi. The girl, wide-eyed and frozen stared at her step-brother's nearly naked body. The bathroom lighting providing a much better view of his muscularity and general build for her visual consumption. Snapping out of it, she quickly yanked down on her shirt hem to attempt to cover up some part of her exposed lower body, barely able to cover the lower part of her stomach.

"OLIVER! I'm in here! Get out!" Madi screamed, using her free hand to cover herself as best as possible.

"Sorry, but I need to brush my teeth... wouldn't want to offend you with my breath," he replied as he took a couple more steps towards the sink and then cocked an eyebrow at her. "Are you taking a dump?"

"UGH! No! I'm about to pee!" she yelled, exasperated that she even had to continue with this conversation. "I locked the door!"

"Oh, yeah, the lock doesn't work... been meaning to fix that," he laughed. "I'm not stopping you from peeing, so go ahead."

"Seriously? I can't go with you in here!" Madi pleaded.

Oliver walked in front of his sink, directly in front of the toilet. His back was turned to her, the mirror in front of him only giving him a view of her if he were to step over to the left or right side. He grabbed his toothbrush and paste and quickly began to freshen up his mouth, not wanting to ruin the atmosphere of sexy competition that they had established just a few minutes prior.

Madi focused hard on the back of Oliver's head, hoping that she could go without him turning around. Her eyes admired his masculine shape, unable to break away from staring.

Without warning, Oliver's knee buckled hard like a cheap tent crumpling from a gust of wind. The thunderous shove against the back of his knee and uppermost calf left him unable to stop his descent. He lost his footing and lunged forward as his kneecap crashed into the vanity cabinet door handle. His hand opened by accident, releasing his toothbrush into the sink.

"Madi!" he chided her. "That actually hurt a little."

He turned to confront her. She grinned at him and raised her foot again to repeat the attack.

"Good. Get out already!" she fired back without hesitation, finding herself more playful than upset, a bit embarrassed, but not actually angry.

Stunned, but not entirely surprised that she resorted to doing that, Oliver shook his head and turned around, facing the sink and mirror again to spit out the residual toothpaste from his mouth and to rinse and make his escape.

The moment he did, Madi kicked him again in the same spot, sending the same knee into the same handle. The young man grimaced and grasped the countertop for support. The girl saw his reflection in the mirror, delighting herself with what she simply considered a reasonable defense.

He turned his attention back to his sister who sat patiently on the toilet to pee, having a hard time holding back the floodgates now.

"You're so going to get it now..." he bemoaned.

Oliver turned around and shifted to the side, keeping himself safe from her fierce and unforgiving kicks. He rinsed quickly and shut off the water before turning around and focusing his full attention on the girl.

Madi sighed and started to relieve herself, peeing away without reservation. With lightning speed and precision, Oliver's hand was wrapped around Madi's heel, lifting it up to his knee. He grabbed her other heel and did the same, fixing her feet against his lower thighs as he started to strip her of her pants as punishment.

"Ollie! Ollie! Ollie! No, stop playing around!" she smiled and giggled with a nervous laughter while rapidly calling his name to try and appeal to him to no avail.

Successfully stripping her of her pants, he backed away, leaving her with just the skimpy black thong around her ankles.

"You'll do better with fewer clothes... should give you an edge," Oliver teased, wadding up her sweatpants into a ball before heading out of the bathroom, closing the door behind him.

"Hey! Come back! Oliver! Give me back my pants!" Madi squealed, but then trailed off into a whisper in case the commotion brought uninvited and unwanted guests to inquire. The last thing that she wanted was anyone else knowing what was happening.

Despite the embarrassment of being walked in on while on the toilet, the girl couldn't stop her face from lighting up as they play fought, even when she was stripped.

"Oliver, you're so dead now," she grumbled through a smile, still unable to bring herself to be truly mad or upset with him.

Oliver chuckled and walked off the light damage to his knee, considering himself lucky that he was able to brace himself better the second time. A couple knee bends while standing and a quick rub of his kneecap and he was ready to punish Madi.

A reflection of the lamps in his room shined on his doorknob, catching his attention. He glanced at the door and then walked over, locking the door for their privacy. "Madi was right to lock the door last night..."

Oliver took a running start, launching himself onto his bed before he turned on his side for the moment to shove Madi's pants underneath his pillow.

As he turned back over, his bathroom door slowly opened. Madi, in just her short little pink tee and her fully visible black thong, stood in the doorway. With a smirk on her face, she started to approach him.

"Well, it took you long enough," he said with a smile, staring her down. "Now, come get your spanking."

"Ollie... pants. Back. Now," she said with a hint of embarrassment masking any semblance of anger. She spotted the slight bulge in his boxers, but that didn't deter her.

Oliver grimaced as he moved to his knees, kneeling on the bed, keeping up the charade for her sake. Finding her entire presentation cute and sexy, he matched her tone.

"Madi... come. Get. Them," he replied, grinning at her. His eyes blazed with a passionate longing that seemed years in the making.

She nodded and approached quietly. The arrogance on Oliver's face goaded her as she sprang from her feet. Like a skilled ninja, Madi leapt onto the bed and wrapped her arms around Oliver's neck, catching him off guard while swinging around to get behind him. She stepped between his bent legs, foot between his knees and tried to take his back, cinching her forearm underneath his chin.

Effortlessly keeping still with her weight trying to bring him down onto his stomach, he let out a short laugh as he pressed his chin down to block her from fully choking him.

"I'm impressed, Madi..." Oliver said while sporting a wide grin. "But I'm going to punish you now. I'm going to teach you a lesson. Ready, babe?"

Madi snarled and shook her head in defiance, breathing hard as she processed the humiliating words directed at her, mostly taken aback by the unexpected term of endearment, one that she never expected to hear him direct at her.

"Shut up, Ollie!" she grunted under strain while changing positions.

She wrapped her other leg around Oliver's abs, then jumped to get both legs wrapped and locked around his waist as she rode his back and desperately tried to take him down by jerking her weight.

"I think you're trying to lose," he whispered as their heads were close. "I think someone likes when I strip her down."

"You wish," she grunted back, finding his aggressively flirty tone a major turn on for her.

"You're so cute when you're mad like that," Oliver grunted, laughing before he reached down with his fingers and gripped one of Madi's feet.

He started to gently massage the ball of her foot to her amusement.

"W-What are you doing? You can give me a foot massage when you lose," she laughed, again trying to shift her weight to pull him downward.

"Not exactly trying to massage your foot," he replied slowly as his fingers began to move in opposite directions from one another, breaking out into a slow but steady tickling motion.

Madi grunted and gasped, trying to resist, but ultimately failed as she yanked her foot down, away from his tormenting fingers.

"Good girl," Oliver said, patronizing her slightly.

With her foot dropping back to the bed, the ex-wrestler reached back and pushed the girl towards his other side behind his back, dropping his shoulder as well in the process. He grabbed her forearm and pulled it forward, releasing his chin and neck as he held on tight and pulled downward, bringing Madi down onto her stomach like a surfboard.

"Ugh!" Madi cried out in shock as she tried to use her arms to break her fall.

Oliver dropped his left side on top of the girl's lower back, pinning her between his extended elbow and his armpit. He created a bridge with his arm and body to keep her trapped and effectively cut her off from her legs. He leaned back a bit and wrapped his left arm around her lower waist, just above her underwear band.

Finding no reason to resist now, his right hand gripped her firm butt cheek in his hand. An unhindered squeeze made Madi's eyes widen and left her jaw slack. Oliver gingerly tapped her butt cheek twice, watching the jiggle of his step-sister's perky butt just inches from his face.

"Time for your spanking, Madi," he teased.

"Ollie!" she squealed, trying to kick her legs back and strike him like a scorpion, eager to get free of this precarious and compromising position. She threw her arm back, crashing into his upper back like a wall and then tried to swing her other arm, landing nowhere. "Don't even think about spanking me!"

"Don't do that or you'll just hurt your shoulders," Oliver warned as he started to rub both of Madi's butt cheeks slowly. He brought his hand back and dropped it across her cheek, creating a beautiful skin-to-skin sound that echoed right into the young man's ear.

Madi flailed and tried to get herself free. The growing sense of shame rose steadily as she knew that she should not have ended up in this position, at least not so easily. However, the sense of excitement climbed even faster, leading her to longing for more.

"Ollie! Ollie! Please!" she pleaded, yet again using her inside voice, just below her normal speaking volume.

"Don't thrash, Madi," Oliver warned her again, unleashing another swatting, but this time to her other butt cheek. "The more you resist, the longer I'll have to spank you."

The grunts and groans from Madi filled the room as did the steadily rhythmic smacks of Oliver's hand striking the girl's buttocks, keeping them very light and sensual. The mental and emotional toll evident by the raspy breathing and the continued squirming only communicated to Oliver just how humiliating this was for Madi. He also knew that she was enjoying it as well as he caught an earful of responsive moans that she tried to stifle by muffling her mouth with her hands.

Reaching for the pillow ahead of her, Madi pulled it downward and cradled it tight as she felt a surging excitement begin to overtake her reason. Her fingers traced soft fabric below the pillow, finding a lump that she pushed forward to bring into view. Her sweatpants, what was stripped of her, now dangling between her fingers, led her to contemplate only for a brief moment her true desire. That's all she needed. With a shove, she pushed her sweatpants right off the edge of the bed to the floor, all while still being spanked.

The light thud caught Oliver's attention for a moment. He paused, resting his hand on Madi's butt cheek while turning his head back slightly. Satisfied to continue again, he quickly resumed the girl's punishment to her delight, not so secretly.

The hand came down again and again, accompanied by a light squeeze. Enduring a couple minutes of the steady punishment, Madi finally relented as her struggle to keep her arousal under control failed. The act of being spanked, of being disciplined and restrained, by a man whom she deeply cared for in a way that she didn't fully understand until this moment, was more than she could bear.

"Ollie! Ollie! Okay! Okay! You win!" she cried.

The blonde relinquished her fight and laid her legs back down, cradling the pillow around her head like it was a trusted stuffed animal. The heat radiated from her face as she tried to remain still. Burying her pleasure and desires into the pillow, Madi clutched it and clamped her teeth down into it for support. Her growing sexual frustration and need felt impossible to suppress now.

The young man smirked, unleashing another final soft spank to Madi's butt before changing tactics. He scanned that pert little tush of hers, still maintaining her natural light complexion with maybe just a dash of pink where he'd struck her lovingly. Oliver had no intention to hurt Madi or leave a mark or bruise. His only goal was a lesson in obedience, in submission, one that Madi desperately needed.

With her butt inches from his face, he pulled up on her waist with his left hand, bringing her butt up closer. Lips drawing near, he planted a firm, but soft kiss on each cheek, as a way to soothe the stinging sensation and to escalate things further along.

Madi's eyes widened as she lifted her head up slightly, looking ahead while moaning out softly at the surprisingly welcomed gesture, one that struck her as both sensual and sweet.

The ex-wrestler gently released her waist, retracting his arm like a tentacle. He pressed her down softly, flat onto her stomach. Madi's light pink shirt rode up during the initial scuffle, staying up now to expose a hint of black from her bra. The small of her back laid naked, the black thong looking too cute on her perfect figure. The slim waist, the slightly widening hips into that peachy tush of hers, down into her slender legs, and off to the soles of her feet, all of it fully in Oliver's sight for the first time at this range with this type of circumstance. Seeing Madi in a bikini was one thing, but this was quite another with the intimacy being the key difference.

Madi couldn't believe what had just transpired. Her heart fluttered from the very first spank, her excitement rose with each subsequent spanking, but the major factor that eventually kept her calm and docile was Oliver's tone. The marked difference in him in the bedroom hit her like a spotlight on a first-time performer at a play. Nervous and eager to please, Madi found herself retreating into a sense of security through obedience. Inward and then overflowing from her, she refused to allow herself to fake her feelings, to change the trajectory of her path, to change from just going with the flow and being natural.