Crossing the Line - Cover

Crossing the Line

Copyright© 2019 by Twren

Chapter 3 - Winterhaven

Incest Sex Story: Chapter 3 - Winterhaven - Samantha is a smart, attractive 17 year old high-school senior who had grown up with her younger brother as her best friend. This is a story about how she came to realize her ideal mate had been living just 10 feet away from her for her entire life. Starting with the discovery of their unconventional feelings towards one another during an experiment with Ecstasy and progressing through the Holidays and on into College, Alex and Sam nurture the well of emotions and lust that grow between them

Caution: This Incest Sex Story contains strong sexual content, including mt/ft   Mult   Teenagers   Consensual   Drunk/Drugged   BiSexual   Heterosexual   Fiction   Humor   School   Sharing   Incest   Brother   Sister   Group Sex   Cream Pie   Double Penetration   First   Masturbation   Oral Sex   Petting   Tit-Fucking   Big Breasts   Violence  

Winterhaven

Silence reigned inside the Jeep as Mike and Sam neared the finish of their 5 hour drive back home from the camp site. Things had changed drastically the second morning of the groups planned 3-day camping excursion, having been abandoned by her boyfriend during what should have been the most erotic and sensational experience of their young lives up to that point.

With all 4 of their group high on Ecstasy and marijuana, their shared tent had quickly evolved into a temple of the senses on that first night, with Samantha’s best friend JoAnna lying naked on the floor and inviting any of the other 3 to come and touch her. JoAnnas boyfriend had quickly obliged, while Sam and Mike had begun fucking on the floor nearby. When it came time for Mikes “big finish” however, Sam had told him to pull out. While this was normal during sex, he had immediately gotten up and moved over to JoAnna so that she could suck his cock to finish him off while she was being ploughed from behind by her own boyfriend, Reed.

Sam did not mind really, in the end she realized that Mike simply no longer held the same place of importance to her, and so the following morning she had worked herself up to feign heartbreak as to having been “betrayed” by Mike. While it was not true, she figured this would be the quickest, cleanest way to extricate herself from the relationship.

“An unforgivable mistake in judgement all around, but none of us can take it back and i will never again be able to see you in the way I once did” That is what she told him. And he understood. How could he not? They were all high and he had given in to his deepest and truest urges, in the end opting to satisfy himself with Sams taught, fit, young looking gymnast friend rather than spilling his seed on Samantha’s stomach as he had done many times before.

Everyone in the group understood, and no one could blame her for the way she said she now felt, but it was all a lie. She didnt care that her best friend was a cumslut who let Sams boyfriend face-fuck her. Hell, Sam had done all but encourage it with the way she had glanced suggestively at JoAnna after telling Mike to pull out, but no one else seemed to put it all together.

Luckily for her.

Now, after giving up on the pretense of trying to finish the camping trip while still having a good time, they had all decided later that 2nd morning to head back to town. Sam and Joey hugged each other as girls do, even when they hate each other they can still put on a good face. Though, neither of them hated the other, Sam was just kinda confused. On the one hand, JoAnna had helped her extricate herself from a relationship she no longer wanted. On the other hand, it seemed like Joey would have taken any other boy that had been there with them, no matter who claimed him.

At that thought, Sams mind flashed to Alex, if he had been there and been the one whose cock Joey had drained down her throat.

“Over my dead, rotting corpse” Sam almost said aloud, but was able to keep it internal. She was going home to her brother and she would be DAMNED if JoAnna and he were ever in the same room together again, let alone in a position where Joey could steal him from her.

“Ok, what th’ hell?” Sam said to herself, “it was one night and we haven’t ever expressed any kind of similar desire towards each other, And here i am already talking like he’s my boyfriend. He’s my goddamn BROTHER” Sam sighed as she finished her thought, what was she to do?

Getting closer now to her house, Sam texted Alex to come out and help her bring her bags inside if he was home. She got no response during the intervening minutes, so she assumed he was gone out with his friend Brian or something. No big deal, she could carry her own bags


As Alex turned off the shower head and opened the curtain, he reached for the towel and started patting himself dry. With the towel covering his head he suddenly heard his sisters ringtone going off - ‘what ifs’ by Kane Brown - he quickly wrapped the towel around his waist and hustled to his bedroom to answer the phone. Upon looking at the screen he saw that it was a notification from his sister, apparently she would be home today and...”wait what? ‘Almost home’?” As he realized what the text said, he heard a car parking in the driveway. “Shit!” Alex said while rushing to the window. He moved the curtain and looked out at the driveway. Not giving much thought to it, he dropped the towel and quickly grabbed some sweat pants and threw on a windbreaker then headed to the front door.

Stepping into his sandals that always sat near the front door, he stepped outside and glanced down the driveway. Alex saw his sister pulling the last of her bags from the back seat of Mikes Jeep, so he rushed down to help.

“Hey Sis, hey Mike” Alex said, moving his hand in a small gesture of acknowledgement towards the drivers seat, he heard Mike say something but it was not clear. Reaching the car, Alex came up behind his sister who was still leaning in the back seat of the jeep trying to get her last night-bag. With a glance around Alex was able to subtly take in a few key details - he noticed that Mike wasn’t helping Sam with her bags, Sam had tossed her bags on the snowy ground seeming not to care that her things might get wet, and the fact that she was wearing her fluffy pajama bottoms and an oversized T-shirt that she normally reserved for bed-time. All of this combined with the unexpected fact that she was home over a day early told Alex that something had gone wrong on the trip.

Being a considerate brother, Alex leaned down to give his sister and best-friend a brief hug while welcoming her back. “Hey there” Alex said, giving Sams shoulders a squeeze, “I’ve got your bags, go ahead and finish up anything else you need to do and come inside where its warm” he finished, taking the night bag out of her hand and situating it around the other two larger bags he already had under his arms. Nodding his head to Mike, he said “Mike, good to see you and thanks for getting my sister back safe, I gotta get inside before I catch cold, because my hair is still all wet from the shower” Alex then turned and walked back into the house after acknowledging Mikes half-hearted response.


Even though it was Christmas break and the kids were out of school, their parents still had to work. Their Dad worked in the petroleum industry as a truck driver, so he worked 12-14 hours a day usually, and their mom was a nurse who also worked 12-hour shifts at the local hospital that was just a few blocks away. Both of them started around 6 AM and it was only 830 AM now, so Alex and Sam had the house pretty much to themselves until dinner when aunt Christine and the family would probably insist on taking them all out for some fancy spread.

Setting the bags down next to the couch in the living room, Alex went back to his bedroom, removed his windbreaker and continued drying himself off with the towel. “Damn its freezing out there” he said to himself. Bare-chested, Alex went back to the kitchen to set some water to boiling for a cup of tea.

“Some cinnamon and cloves I think will be just the thing right now” He said as he fingered through the stacks of tea bags in the wooden box his mom kept on the counter. “Maybe with a hint of peppermint” he continued, grabbing a candy-cane off of the refrigerator to use as a stir-stick.

Their family was absolutely nuts when it came to christmas. The tree went up the day after thanksgiving every year, each family member had a box of ornaments they had collected for years, and they always spent the morning together trimming the tree on Black Friday. Alex and his father would then spend the afternoon outside hanging lights up around their yard, house, and garage.

“God damn, Tom!” One of their neighbors had commented to Alex’s father this year, “you’re going to induce neighborhood-wide seizures if you put up many more lights” he said with a smile and nod at the house, clearly joking.

While Alex was finishing up with the tea box, he heard the front door close and knew that Sam had finally made it inside. He was a bit nervous and unsure about his relationship with his sister at this point. He knew they had both had fun a few nights ago when Sam had tried the Ecstasy, and the morning after hadn’t been very awkward at all, surprisingly. Alex wasn’t sure how to act now, he had always been best friends with his sister, and they had seen each other naked before that time but it had always been in passing by accident - someone walking in on the other, or not realizing the other was home when walking naked from the bathroom to their respective bedrooms, things like that. He had never, NEVER woken up and watched as his sister had to wipe his dried cum off of her body, but she had done so all the while chatting with him in a pretty normal way as they always had - talking about christmas plans, her pending camping trip, and their visiting family from out of town.

As Alex was standing there waiting for the tea kettle to whistle, and getting lost in his recollection of that night and the following morning, he heard some vague shuffling behind him and knew that his sister was in the kitchen now. He felt arms wrap around his bare waist from behind, locking together over his flat, toned stomach and shook himself out of his revaries back to the present. Alex put his hand on his sisters hand, startled and turning around “Hey sis, how was the trip?” He said while bending down just a bit to wrap his best friend in a hug, rubbing her back in a vigorous manner so as to warm her up from being out in the cold. “It was ... interesting” She said into his neck and ear as she returned his embrace. Alex could tell something was wrong. From the way that Mike just sat in the car as she got her bags, to the silence between them and the fact they had returned home a day early, and now she was clinging to him in a way that seemed she didn’t want to let go. He could tell she needed the hug, so he just stood there and held her for a few moments.

Wouldn’t you know it, about that time was when the kettle started its low whistle. Alex pulled away from his sister, holding onto her arms and rubbing them up and down in a warming gesture that also conveyed that he was concerned about her, he looked into her eyes and said “Whats wrong sis? You seem down”

“Its nothing really, Mike and I broke up last night and I just wanted to come home” She said

“Broke up!?” Alex said, surprised. “Ohh I’m so sorry hun, are you OK?!” he said as he pulled a 2nd cup and saucer down from the shelf and began pouring them both a cup. “Its fine, I don’t really want to talk about it right now, I just want to relax and hang out with my brother for a few hours” she said with a small smile as she took the offered cup. “Hey! Where’s MY candy cane?!” she said, noticing the one he had stuck in his own cup. “OH SNAP!, Sorry!” Alex said, spinning around and grabbing another one off of the refrigerator, opening it for her, and then flipping it up into the air to land perfectly in her cup with the cane end overhanging the edge. “Oooh, it’s good! 10 points” he said with a grin, holding up his arms as if he had just scored a field goal Sam just grinned at him, her brother could always bring her spirits up.

“So what do you want to do? I had some plans with Brian and Nicole today, but they can go to Winterhaven by themselves that’s no big deal”

Brian Sonders had been Alex’s best friend since they were young and Brian’s family had lived next door, and his younger sister Nicole was always tagging along whenever they went anywhere. At 16, Brian was the same age as Alex (though not in as great of shape), and Nicole was a bit younger at 14. The Sonders’ home life was a stark contrast to Alex and Sam’s. Their dad had skipped out on them when they were only children, and their mom worked 3 jobs to make ends meet while holding her own drug addictions at bay. A few years ago their family had moved out of the neighborhood and to an apartment a few minutes away because they could no longer make the mortgage payments. Owing to the fact that the two kids had been forced to grow up so fast, Brian had the maturity of an older college man and his sister was one of the smartest people any of them had ever met. Seriously, it was freaky some times - Nicole was always quiet but never missed a thing.

“OH Winterhaven sounds GREAT! Let’s all go together, it’ll be a good distraction!” Sam said

“Ok! I’ll shoot him a text and tell him to pick up another ticket” Alex said

Winterhaven was one of their favorite Christmas time traditions. It was a large neighboorhood near the outskirts of the city, where each house put up dazzling displays of christmas lights every year. The Home Owners Association worked with the city to make it a kind of ‘destination’ for locals every year, blocking off streets so that they could run hay-rides through the neighborhood. Tickets cost $10 a piece, and the hay-ride usually lasted about 2 hours, taking a route through the neighborhood, and at the end turning around and going back the same way, that way the people in the wagons could appreciate both sides of the streets without having to keep looking over their shoulders at the other side.

“What time were you guys planning on?” Sam asked

“The 8-10 o’clock ride tonight” Alex said

As they talked, both of them had moved from the kitchen and back towards their bedrooms. They went into her bedroom because it was the closest and she wanted to sit on her own bed. Alex took a seat in the gravity chair next to the closet and flipped on the radio sitting on her night-stand

‘Come to me’ by the Goo Goo Dolls had just started playing

Sam sat on her bed with her legs crossed and was mouthing the lyrics as she sipped the tea appreciatively

“Come to me my sweetest friend, Can you feel my heart again, Ill take back where you belong, And this’ll be our favorite song...”

Both of them could tell there was something not being said. Neither of them wanted to talk about the giant elephant in the room that was the sexual experience they had shared just a few nights previous.

“Hey Alex... ?” Samantha said “Hmm?” He said as he took a sip of his tea and continued flipping through one of the magazines that Sam kept on her dresser for light reading

After a moment he realized that Sam hadn’t said anything further, he glanced up at her and noticed she was looking at him intently. Once she saw that she had his attention, she said “Im glad you are my best friend”

With that one small statement, Sam had made Alex understand that there were no regrets from the sex they had shared a few nights back. She cared about him and would not let that experience change their relationship in any negative way. He hadn’t realized it fully until that moment, but he had been VERY anxious and did not want to broach the subject in case it triggered the beginning of the end to how their lives had been up until that night.

Alex let out a heavy sigh and smiled at his sister. “I love you” he said as he had thousands of times before, but this time there was an underlying promise that said it was more than just the love of a sibling and best friend.

“Hey!” Sam said suddenly, pointing at the small table under her TV “Hand me that controller” The two then proceeded to spend the afternoon as they often did, talking about nonsense and playing video games, no longer having any tension about had happened or what might happen between them.


Sam ran up, slapped the hood of her car and yelled “HA! Slowpoke!” then began dancing in a goofy manner, pretending to be a cowboy riding a horse and galloping around in a circle while Alex continued hopping towards her, still trying to pull on his left sneaker without letting his foot touch the snow.

“Beat you again SUCKAAAAA” She said, totally hamming it up and making fun of Alex.

“Ok Ok, it doesn’t help that you already had your shoes on and were halfway out the door when you said “Last one to the car buys the coffee tonight!” he grinned. He loved seeing his sister in such a joyous mood, so he wasn’t disappointed that she had beaten him. “Lets punch the highway, we gotta pick up Brian and Nicole in 10 minutes” he said

“... ‘punch the highway’?” Sam asked, then thought about it for a second, “oh... ‘hit the road’” She realized and rolled her eyes. “You know, you aren’t half as funny as you look” She told him while leaning on the hood and trying to conceal a smile at his corny play on words.

While Alex bent down to finish tying his shoe, he said “You will regret not putting on a heavier coat or some sweatpants later, mark my words. Yoga pants might be comfortable, but not THAT warm.

While he was talking, Sam picked up a small handful of snow and, with a mischievous grin on her face, said “And thats why we’re bringing blankets duh, Ill be fine”, then proceeded to stuff the snowball down the back of Alex’s shirt. With a yelp of surprise, Alex lost his balance and landed in the snow on his butt. He looked up at his sister with an unreadable look in his eyes, and somehow she knew that she would pay for that bit of cheek. But before he could do anything about it, Sam opened the drivers side door and got in, locking it behind her and sticking her tongue out at Alex. She rolled down the passengers window and yelled out to him “Hey come on, remember we have to pick them up in a few minutes, you are going to make us late!”

With a sigh, Alex accepted the defeat at the hands of his devious sister, vowing to get her back. He opened the car door and got in.

Keeping up with his sisters rambunctious attitude, he buckled in and yelled “ONWARD!” while pointing forward as if a commander leading his troops to victory. Sam rolled her eyes and put the car in reverse to back out of the driveway.


“Yeah we’re pulling up now, don’t forget the blankets” Alex said into his phone while talking to Brian. He ended the call and put his phone in the center console, “They’re coming out now, apparently Nikki misplaced something and is freaking out”

Sam was semi-listening, but more engrossed in the song on the radio. ‘I like it like that’ by Hot Chelle Ray As she lip-synched the up-beat song and moved her arms, dancing in her seat while pretending to be on stage singing to a crowd. Holding the pretend microphone out to Alex as if he were a member of the crowd she sang:

“If you’re with me let me hear you say...

I like it like THAT, Hey, windows down, chillin’ with the radio on I like it like THAT, damn, the sun’s so hot, make the girls take it all off I like it like THAT, YEAH!, one more time, I can never get enough Of eee-vree-boody, Sing it right back, I like it like that!”

“Man” Alex thought to himself, “she’s really in a great mood! I’m so glad, I hate seeing her how she was this morning”

Just then, Brian and Nicole came through the gate of their apartment complex, Brian carrying a backpack and a few blankets, and Nicole bundled up so she almost looked like she had to waddle to the car in her thick jacket and pants.

Sam turned down the radio and rolled down the window, “Hey there guys!” She said, “looks like you guys are prepared for a blizzard haha!”

Brian opened the door, leaned in and tossed his bundle onto the far seat, then backed out and motioned for his sister to get in and scoot to the far side. “Hey you two” he said, “glad you could join us Sam, I thought you were going to be camping tonight still”

“Yeah” Sam said, “I decided to come back early ‘cuz I didn’t want to miss Winterhaven”

Brian was 16 years old and 6’ tall already, and he was built like a linebacker with thick slabs of muscle and the small gut that usually comes to those that have large frames and don’t watch what they eat because they have fast metabolisms. He was by no means ‘fat’, just large and strong. A contrast to her brother who was more lean and muscular. Brian wasn’t very excited to have his sister always tagging along with him, but he had grown used to it over the years. He was like a surrogate father to her since theirs had ditched them years ago, but he didn’t really treat her very nice all of the time, he made her feel more like an inconvenience than a friend or sister.

Nicole was only 14, and on the small side for her age. A Freshman cheerleader at their highschool, she was the top of their cheerleading pyramid because she was so petite. Standing at 4’ 7” and only 85 lbs, she was still well-proportioned and was growing into her young-adult self quite nicely. Her training routines with the cheer squad kept her butt nice and firm, her legs well-toned, and her midsection toned and tight. With nice, perky, C-cup breasts, she was what the guys at school called ‘fun-sized’. Having lost her virginity in Junior high, she knew she was ‘hot’ and liked to tease the guys but had lost interest in most of the ones at their school because she was so much smarter than they were and they came across as too immature.

Constantly bored in classes, she occupied her mind with making observations of the people around her. With only a few minutes of observation, Nikki could tell if a boy liked a girl, or if a couple had engaged in sex, or if one boy had cheated on his girlfriend among many other things. Nikki wanted to be accepted so badly, she wanted to feel like someone cared for her and loved her not because they had to, but because they wanted to.

She also used her charms to score drugs on occasion. Not that she would take them very often, but if a boy was hoping to get in her good graces and wanted to give her a few free pills or a joint, she wouldn’t turn them down! With a drug-addict mother like they had, Nikki had realized at an early age the value of drugs and that they held their worth and could be used for more than just getting high.

Although Nikki had always been ‘around’, she had just started to gain acceptance with the small group of friends this year as she joined them in highschool. Sam often found herself hanging out with Nikki when the 4 of them would go to the mall or a movie, they would chat and giggle as young girls do.

Sam looked in the rear-view mirror and said “All set?” Everyone checked their mental lists and nodded or made gestures to the affirmative. “annnnd were OFF!” Sam said as she accelerated from the curb side, heading to the outskirts of town and towards the starting point for the hayrides.


As they stood in a group chatting with some strangers who were also going on a hayride, Nicole asked Brian, “Hey, can we get some hot chocolate?”

“Sure!” Brian said, Ill go get it. What do you guys want?” He asked Sam and Alex

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