Adam stared below him as each thrust was mesmerizingly swaying the brunette’s supple tits. The fact that he was repeatedly ball-deep in his bitchy stepsister, Holland, made him achingly harder. Glancing to his left, his fiancée Mia stood in green lace thong panties, intently watching her husband-to-be, giving his stepsister the raw fucking of her life. Holland, confused but lost in her own lust, licked her lips unconsciously as she looked at the lithe blonde. Mia wryly smiled at no one in particular and took that as a sign from the thoroughly fucked brunette.
Moving deftly, she knelt on the bed and lifted one leg over Holland so that each knee was beside her head. She pulled her panties to the side and slowly lowered herself onto Holland’s face saying, “Now how about a nice little welcome to the family for me, my little pet.”
****
Twelve years earlier, Holland’s mother had just married Adam’s father and it was move-in day for the ladies. Adam watched as Holland, everyone’s perfect high school sweetheart, walked into the house taking up residence in a bedroom across the hall from Adam. The mid-summer sheen of sweat was glistening off her body from bringing boxes to her room. She was every teenage boy’s wet dream.
Trouble was, she wanted nothing to do with Adam. Even though she was just over a month his junior, she had absolutely no respect for him from day one. The newlywed parents had forced them into ‘bonding time’ that was punctuated by Holland repeatedly telling him how much of a loser he was. She’d find a way to tell him differently each time, attempting to be crueler with each barb.
Adam had struggled with everything over the loss of his mother. A brain aneurysm had unexpectedly taken her away from him just four years ago. His life was sent into a tailspin, and his father, Bruce, tried mightily to help, but in the end, the easier route was to withdraw from it all. As Bruce started dating again, Adam rebelled against everything he thought his father held dear. His grades plummeted, he dropped out of all of his sports and afterschool activities. He was on the fast track to a long unfulfilling life. Holland dutifully reminded him of this almost daily.
As high school progressed, Adam learned to hate Holland much more than anything else in life. As if trying to shield himself from the constant vitriol spewed by his stepsister, he pulled himself up and started turning things around. He started caring about school and found a small group of friends that were the 'outsiders' of the high school. His grades started to rise and he slowly crept out of his depressive cocoon to escape, and ultimately spite, the hateful Holland.
He worked to erase years of neglect of his education in his senior year, making the honor roll for the first time since his mother’s passing. This only fueled Holland's hate and contempt for him. The parents continued to shower accolades on Holland at every turn, completely ignoring Adam’s effort to right himself. This just steeled his resolve to make a better life for himself away from all of this... and especially from her.
The culmination of her venom came late at night after prom, as a drunk Holland stumbled upon Adam and his date making out at an afterparty. She viciously laughed at the awkward couple.
“Kim, even you’re too good for this loser. I know you took him out of pity and out of options when Brad dumped you, but you don’t have to debase yourself by making out with this tiny dicked loser! Have some fucking respect for yourself!” Holland cackled.
Kim broke into tears and ran off as Holland continued to laugh at him. She flipped him the bird as she stumbled off with her hunky boyfriend. Adam's hate for her seared deep within his soul. She may have won high school, but I’ll beat her in the long run, he vowed that night.
With her perfect grades, three-season varsity athletics, and ample charity work, Holland went off to Dartmouth on a full ride. Adam was able to get himself into state school based on his senior year performance and an inspired admissions interview punctuated by his grappling with his mother’s death.
The first year at college was much of the same. They both did well, but the praise and love showered on Holland failed to extend to him at holidays and school breaks at home. Nothing seemed to change no matter how hard he worked. He didn’t care and didn’t need any of them much longer. Even his hatred of her waned from the lack of proximity. That first summer he lucked out with an internship at a start-up hedge fund. He threw everything into that job and impressed the firm to a point where they kept him part-time through the rest of his college years.
Over the years, Adam flourished. After he graduated, the firm he’d worked so hard for hired him full-time right out of school, and he quickly became the golden child of the firm with a knack for identifying the hot trends of the biotech sector. He subsequently made a small fortune in a short period of time. He didn't allow the newfound money to go to his head. No flashy cars, just a nice apartment in the city, modestly furnished. He did spend quite a bit on personal training, buffing and trimming him to beyond recognition to any of his old acquaintances. He maintained his relationship with his father, and at this point, had essentially cut all ties with Holland. He now, in some small part, owed his success to the drive catalyzed by his stepsister.
Holland, on the other hand, had fallen on hard times. A liberal arts degree from an Ivy League school didn’t get you very far these days. She thought the jobs she was offered post-graduation were below her. In the end, she ended up living back home falling back with friends from high school who hadn’t been able to escape the orbit of the small town. Her prize boyfriend left her for an older leggy European woman from his new job. She let herself go in the spiraling depression in the aftermath of it all. The constant adoration from the parents turned to constant nagging about her getting a job, at one point suggesting that she get in touch with her stepbrother for help. She scoffed at the thought and in quite the ironic twist, she settled on a barista job at the local coffee shop instead.
The tides had turned on Holland and at twenty-five, she had no sense of direction.
Adam came home for Christmas with a new girlfriend, Mia. Late one night, the two stepsiblings awkwardly ran into each other in the kitchen.
“Go ahead, rub it in my face. I deserve it,” Holland dejectedly sighed.
“High school was shitty. We were both young and dumb and did stupid things. I don’t hold it against you.”
“Are you fucking kidding me? The shit you endured because of me, and now you’re going to give me this smug, ‘I’m above it all now’ shit? Fuck you, Adam! You’re not fucking better than me,” she animatedly gasped.
“You’re right, I’m not. It doesn’t mean I have to hold anything against you,” Adam earnestly pleaded.
“Fuck you, you little prick!” she spat and stormed off.
Doing so, she failed to notice Mia hiding around the living room corner, from where she had eavesdropped on their entire exchange. She’d heard the horror stories of how his stepsister tortured Adam in his youth. She hadn’t quite believed all of it until now. What was Adam thinking, she thought, willing to forgive that stone-hearted bitch after all she'd done.
****
Adam and Mia’s relationship grew and he finally asked her to marry him a year later. The families all came together for a celebration of the couple. As the night waned, a tipsy Holland approached Adam.
“I know you and I are who we are. I’ve been terrible to you ever since I met you. I just want a chance to reconnect a bit if you can handle that?” she sheepishly asked.
“I told you last time, Holland, I’m not the one holding a grudge. If you want to be a part of my life in some way, I think I’d actually welcome that.” He smiled lovingly. “Just don’t think you’ll end up in the wedding party, OK?” he joked.
“Maybe we could hang out sometime? I just don’t want to live the rest of my life as the evil stepsister to you.”
“Haha, I guess that’s why I always hated those Disney flicks.”
They made their niceties all the while Mia carefully watched the interaction from across the room, suspicious of her intentions. Her fiancé had a big heart, maybe too big in this particular case.
Through the following week, the stepsiblings met up for a lunch together later. The lunch started much like the last conversation with Holland apologizing and surprisingly bringing Adam back through the embarrassment of his youth. By the time they were waiting for the check, the conversation had awkwardly landed on a particular instance deeply rooted in Adam’s mind.
“You remember walking in on me in the bathroom?” she leadingly asked.
“Um, er… I think I might have a vague recollection of that.” he timidly replied. His body deceived him as he blushed at the thought.
He’d shamefully jerked off countless times to the mental picture of his eighteen-year-old stepsister, naked and dripping wet as he’d walked in the unlocked and slightly ajar door. She was reaching for a towel as he entered, shower-soaked hair dripping onto the floor. Her young athletically tight body wrung out reaching for the towel rack. Her heavy breasts swaying seductively. The thought was again making him hard.
She too remembered this moment vividly. The look of the scrawny teen much like that of a deer in the headlights in oncoming traffic. He was unmoving, taking it all in before she screamed at the top of her lungs to get the fuck out, as she noticed the outline of his hardening cock in his gym shorts. She had unleashed a tirade of demeaning explicatives soon after getting dressed.
“Yeah, it looks as if you remember it fondly…” she smiled. “I didn’t bring it up to embarrass you, really I didn’t. I just…” she made a show of trailing off.
“Last time we talked at Christmas, I was in a bad spot. Jeff had just dumped me, I was depressed and completely let myself go. I just thought, you know, you grew up seeing me… and that time all of me. I wanted to show you how I’m trying to better myself as a person, mentally and physically.”
She grabbed her phone beside her unlocked it, flicked through a screen or two, and handed it to Adam. “I found my old high school swim team suit. Swipe through and look at these two pics.”
Adam was looking at a picture of Holland in her very tight swimsuit from the high school team. It was a shot of an actual photograph and while the quality wasn’t great, he could quite clearly see the highlights: Her hardened nipples on top of her well-developed chest were pointing out of the suit and her eighteen-year-old body was perfection in every way. Tanned and toned from a season of swimming, she was quite the sight. Memories of her naked body in the shower flashed before him.
Holland watched his reaction closely. He was whetting his lips while studying the pic at length.
“Go ahead, swipe to the next one,” she urged.
His finger swiped to the next pic. His eyes bulged out of his head as there was a top-down view of his stepsister with a combination of her hand and lips around a massive cock sucking a cock looking lustfully at the camera. It was just like she was looking at him.
“What the fuck, Holland!” he exclaimed handing her back her phone as if it had some type of infectious disease.
She feigned surprise and took the phone back. Looking at the phone she instantly acted embarrassed. “Jesus, Adam! You swiped the wrong fucking way! You were supposed to swipe forward!”
“I did! Are you fucking kidding me? I didn’t need to see that!” He shook his head, nervously trying to hide his growing arousal with anger. The image of her perfect lips stretched out over that appendage made his own stir.
“Look, I took a dirty pic with a guy that I met on Bumble. I’m sorry! We all have sex lives you know. Pics are just a little kink of mine… I’m sure Mia, ah, uh, never mind,” she stumbled her words out as she quickly changed the order of the gallery displayed on her phone. She'd made it that either way he'd have swiped he'd have seen the same thing. She quickly deleted the forward swiped photo immediately, just in case.
“Anyway, here’s what I wanted to show you.” She handed him back the phone as Adam took it with some trepidation. “It’s that same suit, just a week ago.”
He looked down at her phone and saw her with the very same suit, pose and smile as the prior one years earlier. She could have passed for her eighteen-year-old self, he thought, but there was something about the maturity that made her look so much better. He resisted the urge to zoom in as the high-cut suit looked to be conspicuously pulled higher, revealing much more skin and outlining her pussy lips to the point of a camel toe.
This wasn’t helping Adam’s arousal. Deep down he knew he shouldn’t be having these kinds of feelings for Holland, but his body had forsaken his will. Holland sat suppressing a smile as she closely watched him almost drool onto her phone.
“Is it that bad?” she asked with faux concern.
“Uh, ah, no. Not bad at all. Um, what I mean is twelve years between the two pics and, um…”
“Um what, Adam?” she prodded.
“You look better today than you did back then,” he blurted out without even thinking.
“Awww, thank you. That’s so nice of you to say.” She covered his hand with hers on the table eliciting a thrill ride-like drop deep within his core.
An awkward silence came over the table. Holland looked up beaming at her stepbrother, caressed his hand lovingly and gently spoke,
“I’m just around the corner if you want to talk some more.” Adam looked surprised at his stepsister.
“I didn’t know you had moved out of the house?”
“I stopped feeling sorry for myself, called a couple of friends from Dartmouth, and got myself an entry-level job at a new advertising firm one of them was starting up. It only pays OK, but it got me out of the house and our parents off my back.”
“That’s great, Holland. I knew life couldn’t keep you down for long!” He was truly happy for her but slipped his hand out from under hers as he congratulated her.
“Come on. Come see it with me. It isn’t much but it’s my first real place!” She was laying it on a bit thicker now. She felt her prey was in striking distance of her meticulously set trap.
Adam looked down at his watch. It was his turn to lie, “I’m sorry, I wish I could but I’ve got to be back for a meeting soon and I’m running later than expected now. Let me take a rain check?”
A crestfallen Holland nodded her head in acceptance. She’d come so close, but his wall might not hold the next time. She had to make sure there was a next time.
“It’s OK. I’m just glad we’re talking again. Let’s do this again soon!”
As they rose from the table and made it just outside the door. Holland gave him a big hug. She could feel him still stiff against her. She quickly realized there was a lot more that was stiff than anticipated. Adam tried to shift away to shield his arousal from her, but the shift had the effect of sliding her full breasts across his chest.
“Thanks for today, Adam. Thanks for giving me a chance,” she said, stifling a gasp. His cock and her breasts shifting across his chest had gotten to her as well. They stepped back gingerly from each other.
Holland added, “Another time. Now get to that meeting!”
“Oh, uh, OK. I’d like that. Uh, bye Holland,” he fumbled as he turned and walked down the street. It took everything he had not to turn around to look back at her.
Holland stood transfixed on her handsome stepbrother walking away from her. She was wrestling with the unexpected feelings she had felt from their embrace. That little fuck was turning her on somehow, she thought.
****
Weeks passed with friendly text messages that eventually set up after-work drinks at the bar of a local trendy restaurant. Adam was waiting at the bar for her as she arrived. Everyone in the establishment that had a view of the entrance noticed her walk in. She wore a charcoal pencil skirt and a white silk blouse that was unbuttoned enough to show much more than a hint of cleavage.
He stood and they hugged. At least this time he didn’t have an embarrassing erection, he thought while still feeling her pillowy breasts against his chest. Adam pulled the bar chair out for her soon after and they were off talking like they were the oldest of friends.
The conversation flowed as did the drinks. Holland and Adam reminisced about their tumultuous times together, shared stories about their parents, and caught up on each other’s lives since.
