An Unlikely Holiday Pairing: Pt. 02

Fingers gripped her shoulder. With one turn, she felt herself spun and rolled onto her back. Her eyes locked with Oliver's as his fiery, hungry eyes met the sparkles in hers. It was a look she had never seen from him before.

No words exchanged. Madi pressed her hands down into the bedding, pushing herself upward a bit more. Oliver followed suit, staying close and keeping himself head to head, face to face with her while kneeling, one knee on each side of her hips. Without breaking eye contact, he reached down and grabbed her wrist, latching his hand around it like a shackle. He raised it up, bringing her hand above her head and pressed it up against the pillow resting against the headboard. He repeated the action, bringing her other hand with ease, no resistance to the same place, both arms bent slightly at the elbows.

The heavier breathing between the two, the near standoff, the palpable sexual tension that no longer could be ignored by either of them, shifted the air in the room. The primal aura between them grew stronger as Oliver leaned down closer, keeping her in place as if she was his prey.

Madi's eyes softened as she felt herself melt inside in a warmth that grew from within her. The growing wet excitement in her panties confirmed the same, fully known to her now. She spread her legs out ever so slightly between Oliver's, signaling her receptiveness.

Oliver moved his head downward, bringing himself closer and to within an inch of her, his nose nearly touching hers. His hands gripped the girl's wrists a bit more loosely, fingers staying tight. He let her arms drop down slightly, just enough for him to rest his thumbs in the center of her palms. With the moment feeling right, he pressed his lips against Madi's lips. Her fingers softly closed on Oliver's thumbs as the pair shared a soft, tender kiss.

That moment--the feeling of euphoric bliss--instantly erupted within Madi before the kiss was broken ever so slowly by Oliver. Their lips parted, reluctantly. Madi looked up into his eyes, no regret of her own for the kiss or for being kissed. She looked at him, she really took a hard look at his face. Her senses seemed overwhelmed, her eyes scanning him as if she were seeing him for the first time. His calming brown eyes, the sharp trimmed beard, the cute smile, but most importantly, the confidence that he wore on his face wasn't that of her step-brother, but of the man that she had been crushing on all day, arguably for years.

"I win, Madi," Oliver broke the silence, speaking slowly to her with his voice smooth like butter.

His eyes traveled upward, being a guide for hers as she followed to see that her wrists were pinned, that she was pinned. Madi turned her head slowly back to Oliver.

The same feisty, sassy, flirty girl who broke hearts all throughout high school suddenly found herself timid, submissive, sexually aroused, and in want. Laying in defeat, Oliver had her pinned as promised.

She threw caution to the wind, knowing that none of this was for the sake of some playful wrestling match between step-siblings, most certainly not that kiss. Foreplay. The wrestling was nothing but a prelude to something greater, an elaborate ruse that Oliver orchestrated, but that Madi wanted deep down.

"Ollie," she spoke, barely above a whisper.

Her natural instincts took over, ignited by the unwavering assertiveness of the man opposing her. Madi raised her head upward and kissed Oliver, meeting his lips. Aggressive in her advance, her fingers clamped down on his thumbs even more.

Oliver returned the kiss with passion, grunting and pushing down as he freed his hands from hers, hers sinking down slowly. The two engaged in the lip-lock even longer than the first one.

Madi slid her hands up the man's bare chest as he leaned down on top of her. Again, Oliver broke the kiss and brought his left hand around her head, holding her close as he planted another kiss on her, this time on her nose, nibbling slightly, then on her cheek before going lower and reaching her neck. His right hand slid down the front of her body, down her stomach and around her back, taking a butt cheek in hand again. A man with a clear affinity for her tush. For all intents and purposes, Madi's butt belonged to him now.

The girl moaned through the sensual neck kisses, extending her head and neck in the opposite direction for him to more easily continue unabated. Her hand traveled upward, running along his cheek, feeling the smaller sharper hairs of his beard tickle her palm. She loved that feeling, the feeling of a man's beard. Such a powerful and simple sign of masculinity, she, as an overtly feminine woman, craved it.

Wrapped up in their passion, blazing hot and fast on the heels of a journey of self-reflection and denial, Madi and Oliver groped and writhed around on the bed without inhibition or pause.

Madi dropped her hand down, along Oliver's not overly chiseled, but visible abs, gently landing on the bulge of his boxers. Her delicate fingers, thin and warm, caressed and gripped the man's erect package, shameless in her desire to take things further with him.

"Let's do it," she uttered in a breathy whisper into his ear as he bucked his hips forward to allow her more access.

He kissed her neck and slipped down lower, kissing the top of her exposed chest, below the neckline. Oliver pulled back and reached down, kneeling with her between his legs. He gently tugged on her shirt as she let go of his manhood. Her arms went up as he removed her shirt from her body, leaving her in just her black bra. She smiled as her face lit up, flushed with lust and passion.

Oliver grinned and stole a quick kiss from Madi's lips before sliding himself down on her body. His mouth quickly found her upper stomach area, kissing softly beneath her breasts as his hands slid under her back to undo her bra for her.

Madi assisted, tossing her bra aside. The arch in her back became more pronounced as Oliver placed his hands, index fingers inside the waistband of her black panties. His mouth gently kissed her breasts, licking and suckling on her nipples that became erect in short order.

"Ollie..." Madi moaned with an almost defeated gasp of appreciation for this man's efforts to pleasure her.

"We're only getting started, babe," Oliver replied, raspy as he kissed his way down her body, slinking down lower until he started to slowly tug down on her panties with each kiss.

Madi's breathing accelerated. The rush of wet heat that radiated out of her womanhood, caused her entire body to ache for something more intimate. She grasped his hair with both hands, pushing down into his head as he focused on her belly button, licking and kissing her there with more fervor. She giggled and cooed, completely messing up his hair as she shoved him lower.

Oliver grunted and grinned as he placed soft kisses over Madi's black thong, kissing the fabric and feeling her shudder each time. He peeled it down to reveal her trimmed hair. She shuddered at the feeling of his wet lips reaching there, kissing her pubic hair, a most unexpected display of domineering affection. He shattered her resolve. Oliver found no desire in Madi to slow the pace or tempo as she normally had to do with a guy.

Madi's thong rested around her ankles as she and Oliver worked together to quickly rid her of them without breaking his concentration. She desperately didn't want him to stop kissing the bottom of her exposed bikini area.

"Madi, wait," he said, pulling his head up slowly. He leaned back and reached with one hand, taking her thong and bringing it to the side of the bed. "Spread your legs."

Madi beamed, smiling at him as she listened despite having no objection. She spread her freed legs out as Oliver positioned himself with his head resting on her lower abdomen.

"You're so sexy, Madi," he admitted for the first time, planting another kiss on her belly button.

He placed his elbow down, left hand across her lower abdomen, and used his left shoulder to act as a buffer so she couldn't close her legs should she have to for any reason. His right hand pushed gently, resting on the underside of her thigh at the midpoint. He flattened himself out, blowing a slight breath out of his mouth against her womanhood, surveying her nakedness in full. Her pussy, lips glistening from her own arousal, beckoned him.

Madi covered her face and arched her back, unable to insulate Oliver from knowing how she felt in the moment.

He leaned in and moved his head to the side, kissing the inside of her thigh instead. Madi's eyes widened at the action. He went in again, and she lifted her head up to watch as he did it once more, kissing the other inner thigh. Like a shark circling its prey, Oliver wickedly teased her, letting the anticipation build. He went for it. His lips connected first, a soft kiss to her lower lips. Madi felt a surge like electricity ripple through her body. The combination of it being a sexual encounter like no other she ever had along with it being with whom she now only saw as the man she had a crush on for years, was enough to make the gesture highly intimate and extremely emotional for her.

"Ollie..." she gasped while instinctively cupping her breasts, her thumbs gently massaging her nipples.

Oliver relentlessly lashed her labia, washing the girl's curtains up and down, before nuzzling in and licking the entrance of her vagina. He repeated the gesture, hearing the girl writhe in ecstasy on his bed.

"Thought you'd like that, babe," he said with even more confidence in his abilities. "You'll like this too."

He started to aggressively lick her clit, flicking it with his tongue while sending her into a tailspin due to her heightened arousal and sensitivity as well as his beard. Her hips shifted wildly, only minimized greatly by Oliver's left hand securing her, the one that he strategically positioned for this very reason. Madi pushed against the restraint, loving the fact that she was being restrained by Oliver as he pleasured her with prejudice.

A series of guttural moans emerged from Madi as her breathing intensified. She threw her head back into the pillow with her eyes closed, her hands against her forehead, finally settling on grasping at Oliver's hair again. Like a comb used recklessly, her fingers twisted through his hair, grabbing and clawing at him as she loved every second of his sexually aggressive behavior.

The giggling smile didn't fade from her face as her body and mind were thoroughly ravaged by this man's mouth as the natural grooves of his tongue lapped and tickled her wet intimate flesh. She found it easy to gyrate her pussy into the man's face, knowing that he loved every second of delighting in the sampling of her nectar. Madi gave it up to him without reservation, as if her honey nectar was rightfully his from the very start, always meant for him.

Oliver's tongue ventured down further as he capitalized on Madi's arousal. A wet lash struck her puckered balloon knot, followed by another and then another in rapid succession.

Madi's eyes opened as she looked up at the ceiling, too captivated by the intense emotions and the erotic atmosphere to be bothered by an incidental lick to her anus. Tried and true, Oliver's resolve pushed him further as he pushed Madi's leg up and back more to cause her butt to present to him more conveniently.

"Ollie," Madi said, eyes opened fully and now realizing that the man was wanting a closer inspection. "Wait, I don't--"

He broke away for a moment. "Hey, it's okay, Madi. Just relax and let me--"

Madi grunted softly, trying to pull herself up on her bed as her butt cheeks clenched slightly. She brought her eyes down to awkwardly lock with his, realizing that Oliver's left hand still kept her pinned down.

"No, Ollie, I've never--" she started, her face now naturally a bit redder as a growing sense of embarrassment started to come up to the surface.

Oliver let go of her leg, moving his right hand down and letting his thumb gently massage her anus, using a steady circular pattern. He held his eye contact with her while doing so, wanting her to fully feel and experience the totality of the safety and trust that existed between them, even if she didn't fully realize it. She couldn't break her gaze, melting at the fact that what she normally found to be embarrassing with other guys didn't even remotely faze Oliver or stop him.

"You can trust me, babe... we're not doing anything that makes you uncomfortable," he said with a reassuring tone, sending a wave of warmth through her as his thumb continued to maintain its circular path. "Now, don't clench."

Madi felt herself able to breathe again, mewling and moaning as Oliver eagerly pampered her butt. She quickly found solace in the man's ability to make her feel safe even when approaching such an intimate area of her body, allowing her to feel at ease and willingly submit herself to him to make the experience perfect for them both.

She never experienced the deep intimacy and eroticism that came with being rimmed by a man, a feeling that left her feeling a deep desire for Oliver and a welling up of excitement in her being.

Finishing out the act with a few quick kisses to her cute knot, his head slid up as he licked her from her crack up to her clit. Madi shuddered and giggled in satisfaction while letting her eyes find his again as Oliver sat up, kneeling between the girl's legs. He slurped the residual saliva around his mouth, the animalistic gesture causing Madi to bite her lip and shake her head at him playfully.

Suddenly, her gaze fell downward, spotting the fully erect cock in Oliver's boxers. With a glimmer in her eye, she smiled and reached out towards him. Her hands started to tug on the clothing, the only barrier between herself and his manhood. Oliver assisted, letting his boxers slip down to the bottom of his knees. His erect cock sprang out towards the girl. Her eyes widened with delight as her delicate fingers gently gripped the warm rod.

"I want it, Ollie," she panted, her voice hushed and short. "I need--"

Oliver grabbed her shoulders with both hands and brought his face down to hers, cutting her off with a passionate and long kiss. Madi melted, but delicately stroked Oliver's cock with an overhand grip before she settled on a more convenient underhand grip, all while still lip-locked.

Oliver groaned at Madi's feminine touch. Her fingers, dainty and thin, felt so good around his shaft. The pre-cum on his tip rubbed into her palm, making Madi even more eager to feel Oliver inside her.

She broke the kiss and pulled her head back, not removing her hand from stroking him. The girl looked into his eyes before she moved close and planted a soft kiss on his cheek. Laying herself back and releasing the throbbing cock from her hand, she slid into position, rolling her knees back towards her so Oliver could position her best.

Oliver moved back and grabbed Madi's thighs, pushing them back and pulling them apart to get the girl into position. Flat on her back, legs up and spread, feet dangling in front of Oliver's shoulders.

Madi reached forward, smiled at Oliver, and gently rubbed the head of his cock as her fingers locked around it, pulling it forward towards her as if she was controlling a snake by the head.

"Ready?" Oliver asked, his voice low, yet full of confidence and desire.

Madi simply nodded and pulled the head forward against her wet entrance. Oliver started to push in as he towered over her. She released him, letting him control how he eased into her. A few short pushes and pulls, and Oliver pushed nearly all 7.5 inches of himself into Madi's wet pussy. Her aching walls welcomed him. Like a husband coming back from war, Madi's pussy walls hugged his cock tight like an overjoyed wife.

"Oh... Oh, Ollie..." Madi gasped, hushed in her cry as she felt Oliver start to build a slow but steady rhythm.

Oliver's hips bucked forward and then recoiled, again and again, letting his throbbing cock thrust into and enjoy the pussy of the woman whom he always secretly hoped would one day be his own.

The room filled with the pants, moans, and the shaking of the bed as Oliver ravished Madi without restraint, her wet, well-lubricated pussy only amplifying the intensity. Mixing in bouts of vigorous thrusts along with the slower nearly love-making ones, his cock felt her walls grip him, their bond strengthened even further by their captivating looks into each other's eyes.

The beautiful blonde basked in the glow of orgasmic anticipation, feeling her body building up to a climax, ever closer. Her rosy cheeks flushed from the deep intimacy that she was sharing with Oliver, her step-brother, but more importantly, her lover, sent her to another sexual high. The sense of sincerity and safety that Oliver made her feel exceeded anything she could've ever expected from any kind of sexual encounter with him.

Her chest rose and fell at a steady pace, her heart rate elevated from the pleasure of their love-making session. Years of pent-up sexual frustration, forbidden love, and entombed feelings finally unleashed in the bedroom after a chance encounter led to deep inner reflection of their love and sex lives, separate from one another until now.

Oliver raised Madi's feet upward, gripping her by the ankles as he continued to plow her. Drawn to her entire body and person, he brought her sole to his lips, planting a soft kiss onto it before moving it back and doing the same with her other foot.

Madi exhaled hard, taken aback by how passionate Oliver was all along. She'd never experienced anything remotely close from her ex-boyfriends, and for Oliver's part, he'd never given any ex-girlfriend this level of what he was giving Madi now. They were all stand-ins, all placeholders, all unimportant now as the union between the pair reignited with another deep kiss.

He felt Madi tighten. Her body twisted in his grasp as he continued to hold the kiss, the weight of and positioning of his hips now keeping her legs apart as he stayed leaned down on top of her to maintain contact. His hands moved quickly, one around the back of her neck while the other gently massaged her clit. He broke the kiss, keeping his nose against hers as he rocked her body with his continued thrusting, keeping their foreheads against each other and their eyes on each other.

"Ol--" she whimpered, barely able to say part of his name before she exploded in a deliciously sweet orgasm.

Madi's toes wiggled and her walls gripped Oliver's cock even more. The feeling of breathless euphoria overtook her as her body, overheated and writhing, felt his touch cradling her delicately until she settled down.

"Good girl, Madi," Oliver whispered into her ear, holding her tight before promising, "you're going to cum on my cock again."

Oliver passionately laid kiss after kiss against her heated face, her neck, her shoulder, and cradled her again, kneeling over as he gently pulled his cock out of her for the moment. The sound of his exit from her beautifully wet slit turned them both on even more in the aftermath of the girl's orgasm.

"Ollie, you're... amazing..." Madi moaned, panting and sweating a bit as the heat that they shared exceeded their expectations.

She reached up and grabbed his arms, her fingers finding and squeezing his upper arms, his forearms, holding them as she strongly felt an overwhelming desire to feel his continued touch.

"Madi, you're perfect," Oliver smiled as he felt the heat surge through his body. He held his throbbing cock, handing under his shaft as he brought it closer to her entrance again, ready to welcome him once more. "Ready?"