STEPSISTER

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by Laffalot

“Man, that sister of yours is fuckin’ hot. I would so love to tap that ass.”

“Dude, she’s not my sister.”

“Okay, your step-sister is hot”

“I know that but you don’t have to be so crude.”

“If she was my step-sister I’d fuck her.”

“You’d fuck a donkey if there was one around here.”

“You may have a point there my friend, but your step-sister is definitely not a donkey and I would chop off my pinkie finger for the chance to make mad passionate love to her.”

“Sure, why not, after all you have two pinkie fingers right.”

“That’s right. How would you like to earn a fifty dollar bill?”

“Doing what?”

“Get me a pair of her soiled panties. Freshly soiled, like right after she strips to take a shower. I’ll give you fifty bucks if you do.”

“Your serious?”

“Of course I’m serious. Look, as much as I’d like to sniff her pussy for real, I know she doesn’t like me and she won’t agree to it. So this is the next best thing.”

“You are one sick, perverted person.”

“But I know that you need the money and your gonna do it aren’t you?”

“I’ll try, but I ain’t makin’ any promises.”

That was the conversation earlier that day between Tyler and Nathan. Nathan had been brash and unapologetic for as long as Tyler knew him, and Tyler was not surprised in Nathan’s reaction when he saw he saw his step-sister Kimberly for the first time. She was home from college for the summer and she was quite a knockout. Long jet black hair framed a perfect face. Sky blue eyes, a cute pixie nose and a mouth that seemed to be designed for sucking a cock. Her body was even better. Tall and slim with curves in all the right places. Even Tyler occasionally caught himself staring at her ass. He was eighteen now and he thought about girls all the time. He wasn’t proud of himself but sometimes when he jerked off he would think about her sexy jean clad ass. He would never admit it though. And now he was going to steal a pair of her panties so he could make some money. It should be fairly simple, he thought, she always takes a shower after working out down stairs and he could easily sneak into the bathroom while she was in the shower and take the panties out of the hamper. He waited in his room and listened to her close the bathroom door and a few minutes later the shower started up.

He waited another full minute, knowing that she always took at least ten minutes in the shower. His room was connected to the bathroom as was her room on the opposite end so he carefully, quietly opened the door and walked in. They had always had an agreement about the bathroom. The toilet was in a nook that had it’s own door so there was no worries about using that. As for the shower, the rule was that if someone was in the shower, the other would respect their privacy. It had always worked and Kimberly had no reason to believe it wouldn’t still work. Tyler worked his way to the hamper, opened it, and peered inside. Her clothes were sitting on top of the pile and he quickly spotted her undies. The were pink with thin straps, but larger than a thong. Tyler closed the hamper and quickly went back to his room. That was easy enough he thought.

Up until the moment he carried the undies into his bedroom and closed the door behind him, the only thing they represented to him was money. Fifty dollars to be exact, and he hadn’t thought about much more than that. He knew what Nathan was going to use them for but hadn’t really put too much thought into it, until now. As he walked around the side of his bed he really looked at what he had in his hand. The thin pink material had a wet stain in the crotch area and suddenly, Tyler had an overwhelming urge to sniff the spot. He knew it was wrong, but he was mostly just curious. After all, he had never smelled the private parts of a female and Kim was a female, and a very fine one at that. His mind rationalized that just a sniff wasn’t that bad, and nobody would ever find out. He raised the garment up and took a tentative sniff from about six inches. It wasn’t close enough so he brought it closer and took another whiff, pulling it away quickly when he smelled a musky scent. He decided that he wanted a better smell, after all nothing could be worse than Nathan’s nuclear farts. Tyler was quite certain they could peel paint off the side of a building. This time he brought the material up close, about a half an inch away, and inhaled deeply. The effect was almost instantaneous.

His penis expanded rapidly as it filled with blood, and he became incredibly horny. He was surprised by the response but remembered what his Health teacher had told the class about the female smell being a turn on to a male. Apparently his teacher had been right on that. He decided right then that he had enough time to masturbate. The shower was still running and he knew that Kimberly would be in there for several more minutes. By the time she shut the water off, dried up, fixed her hair, got dressed and whatever else girls did in the bathroom, he figured he had at least twenty minutes and that was more than enough time. He also knew that his step mother was busy downstairs and she never bothered him when he was in his room. He decided that he wanted to be naked. He had masturbated plenty with his pants pulled down and that was alright, but there was something about getting naked to jerk off that just made it so much better. Part of it may have been the risk of getting caught, even though he couldn’t imagine getting caught. The embarrassment would be so great he would want to die, but it raised the adrenaline and made it somehow better.

Quickly he stripped his clothes off and piled them on the floor next to his bed. Before climbing on his bed he dug beneath his mattress and box spring for the porn magazine that Nathan had given him. It was an older book, mid 90’s, and the condition of it was rough. The book was a fetish book simply titled BDSM. Tyler climbed onto his bed with the underwear in one hand, the mag in the other, and his erect penis flopping around. He realized right away that in order to stroke his penis and look at the magazine, he needed to put the panties somewhere where he could smell them without using his hands. So out of necessity, he put them over his head so that the crotch of the undies was covering his nose and mouth and his eyes were looking through the leg holes. It worked perfectly. Every breath that he took was filled with the smell of pussy, and his hands were both free. With his right hand he opened the book and found his favorite photo spread. In it one man was being dominated by two sexy women. One of the women was older and was dressed like a teacher.

The other woman was probably in her twenties but made to look like she was young with pony tails, a lollypop, and a mini skirt to complete the illusion. The man was supposed to be a student, who was a dumb jock or something. They were all alone in a classroom setting and the ‘teacher’ was pointing menacingly at the ‘jock’ while the ‘schoolgirl’ looked on with a bemused smile. A few pictures later and the ‘jock’ was naked while the teacher sat astride his chest and the ‘schoolgirl’ gripped his rock hard cock in one hand. Tyler was so turned on that he knew it wouldn’t take long for him to explode. The smell of the soiled panties over his face was such a new thrill that he couldn’t remember the last time his dick had been this hard. He was well on his way when the unthinkable happened. The door to his room opened. Not the door into the bathroom, but the door to the rest of the house, and Kimberly walked in. She was starting to say something when she saw him in all his glory and wound up shouting “TYLER, OH MY GOD”

Tyler was in shock and jumped about a foot off the bed. He quickly pulled the covers up in an attempt to cover his private parts. His first attempt failed and he yanked them again yelling “KIMBERLY, GET OUT” but instead she walked toward him. The look on her face was one of revulsion, confusion, and curiosity. Tyler wanted to crawl away and never come back. He couldn’t understand why Kimberly, who was supposed to be in the shower, was now in his room. And then things got much worse.

“Is that Mom’s panties on your face?”
Just when he thought it couldn’t get worse he was reminded that he still had a pair of soiled underwear on his face. He quickly yanked the material off his face before the full meaning of her question hit him like a ton of bricks. They weren’t Kim’s panties, they were her mothers.
“Oh my God your sniffing Moms panties.” This was said in a more controlled voice as she came to grips with what she had witnessed.
“NO” Tyler was still in freak out mode and it was only getting worse. “I THOUGHT YOU WERE IN THE SHOWER!”
“Moms using our shower because hers is not draining good. You are a nasty little pervert.”
“KIM GET OUT!!” Tyler shouted this which was the worst thing he could do.

In the bathroom, Sarah had just stepped out of the shower when she heard yelling from the next room. At their age it was rare for them to fight like this, and the ferocity of the shouting made her rush to wrap a large bath towel around her and quickly enter her step-sons room.

“What’s going on in here? Why are you screaming?” She said mostly to Tyler and then realized that he was naked and his face was redder than she had ever seen. “Tyler where are your clothes?”

Tyler was crying now, his shame was so bad, even at eighteen years old, and he just wanted to be alone. “Sarah, please just leave me alone. It was all a mistake. I need…” he trailed off as he started crying harder.
Sarah looked at Kim for an explanation, but she just smirked and shrugged her shoulders. That’s when she noticed the magazine that had been knocked on the floor in all the commotion. As she bent to pick it up, Tyler lunged for it with one hand. Unfortunately, he wound up falling out of the bed and the blankets that he had been covering up with were knocked aside, exposing his genitals and the panties that he had tried hiding.
“Are those my underwear?” Sarah asked, now completely confused. “Tyler, you need to explain just what the hell is going on. I’m not leaving until I get an explanation.”

If ever there was a time that he wanted the earth to open up and swallow him whole, this was that time. There was no way out of this and he knew it. The only thing that he had was the ugly truth and as bad as that was it all that he had. He took a few moments to try to calm down and work up his courage. Finally he spoke. “It was all just a big misunderstanding. Nathan was going to pay me fifty dollars for a pair of Kim’s underwear.”
“That fucking maggot” Kim angrily snapped.
“Go on” Sarah prodded.
“So I thought that Kim was in the shower and I snuck in and took these.” He held up the pair. “I was only going to hang on to them until I saw him later and then get the money, but I…” He didn’t know how to tell the rest of the story. It was too embarrassing, too humiliating to go on.
Sarah had an idea what happened, but pressed him anyway. “So tell me what happened”
“I can’t.”
“He was jerking off with your panties.” Kim said giggling.
Tyler shot an angry look towards his step-sister.
“Was you wearing my panties Tyler?”
“NO” He didn’t know what was worse, what she thought or what he did.
“Yeah, on his head.” Kim snickered.
“SHUT UP BITCH!!!” Tyler screamed. He wanted to kill her now.
“Tyler I will not allow you to talk that way to my daughter.”
“But ….” This was all going very bad and it was about to get worse.
“Don’t you ‘but’ me young man. So lets put this all together now, you steal my underwear thinking that they are Kim’s, then start to masturbate with this filthy magazine and my undies over your face. Is that about right?”
Tyler just wanted this whole nightmare to be over. He wanted to change the events of the day so this debacle never happened. But he knew Sarah was not in the mood for any lies. He was in enough trouble so he hung his head and said “Yes, that’s what happened.”
“So what do you think your punishment should be?”
He shrugged, still unable to look anybody in the eyes.
“I can’t believe he is so perverted”
That was the last straw for Tyler. He couldn’t control himself any longer. Losing complete presence of mind he launched himself at Kimberly, his hands going for her throat, but she was quicker and stronger and she caught his wrists before he could grab her. His momentum only pushed her back a half step and then she pushed back much harder and they both fell on his bed with her on top of him. She held on to his wrists and climbed up so she was sitting astride his chest.
“GET OFF ME” He screamed vehemently, kicking his feet and trying his best to dislodge her. She simply slid forward and used her knees to pin his arms to the bed, this move put her crotch almost on his neck.
Sarah quickly moved around to the other side and said “Kimberly, let him up.”

But Kim was not ready to quit now. “Mom, are you going to let him get away with what he’s done? He needs to be punished.”

Tyler had been in this spot before when he was younger and had fought with his older and stronger step-sister. In the past when she held him down like this, she had forced him to yell ‘mercy’ before she let him up. He had always held out for as long as he could because he secretly liked it when she held him down like this. It had always given him a hard on that was hidden by his clothes. This time however he had no clothes on and despite his anger, his penis started to grow. He felt the slow movement of his cock and with every ounce of his strength he flung his legs up in an attempt to dislodge her so he could cover himself up. Unfortunately, his plan backfired by pushing her forward so her sweaty shorts covered crotch was right in his face. Had Sarah not been right there, Kimberly would have lost her balance and fallen face first off the bed, however, she saw her daughter going over and caught her. This caused the towel that was covering her to be knocked to the floor and Kim’s face went right into her breasts. This took them both by surprise and Sarah had to hold her daughter for a few moments ‘til she caught her balance. Meanwhile, Tyler’s nose and mouth were up against his step-sisters bare thigh as her shorts had ridden up when she was bucked forward. He turned his head back to try to get air and wound up with his nose pushing aside her panties and coming into contact with her moist pussy lips. It all happened very quickly and was totally unintentional by all involved but the effect was felt by all. Tyler realized in a moment that he had his mouth and nose in contact with pussy and his cock expanded even more, now standing straight up and waving in the air. His arms were free and he was all done being mister nice guy. He knew he was in trouble and he figured that he might as well take advantage while he could so he wrapped his arms around his step-sisters waist and pulled her down tighter to his face and then he stuck his tongue into her vagina.

Kimberly was still getting over the fact that her face was plastered against her mothers tits when she felt her brothers arms wrap around her waist. For a moment, she thought he was trying to keep her from falling off the bed and then she felt his wet tongue slide into her and she gasped. Sarah had no idea what was happening but heard her daughters gasp and as she leaned her back away from the edge of the bed, she heard a slurping noise and Kimberly grasped her mother closer as her step-brother hit her sensitive clit with his tongue. For her part, Kim was very quickly lost in the sensations of the cunnilingus that she wasn’t expecting but was suddenly enjoying. Sarah caught a glance over her daughters shoulder and spied her step-sons seven inch penis standing tall and quickly looked down to see what was happening right below her.
“oh my god” she whispered, then louder “KIMBERLY” Kim opened her eyes and seemed to come out of a trance as she realized what was happening. :TYLER” she shrieked and tried to pull away but he held tight and by now had pulled her shorts and panties aside with his hand and his mouth was attached to her cunt.
“Tyler stop” Sarah ordered climbing onto the side of the bed to try to get him loose.
Tyler was not going to be denied. He was not going to let go. He was determined.

“MOM, GET HIM TO STOP” Kimberly half shouted. It was so wrong, but it felt so good. If her mother hadn’t yelled her name she would probably have let him finish her because it had been so long since she had a tongue in her cunt. But he was her little step brother, even though he was not so little anymore, and it was not right. She tried raising herself up on her knees and Tyler went right up with her. It was a strain on his arms but he was not ready to stop. As she came back down, her clit lined right up with his nose and for a time, he was smothering. The effect on Kim was instant. His nose pressed up against her sensitive bud and his tongue jammed into her pussy was intense. “UNNNHHHHH” she moaned not even realizing she was making noise. She didn’t want this she was trying to tell herself. Sarah was beside herself. She didn’t know what to do, and then Kim moaned and she realized that her daughter was enjoying herself on Tyler’s face. And even worse than that, her own pussy was starting to moisten. What was happening was so taboo but it was hot. It was so wrong, but it was exciting. And she leaned back and let it happen. Kim saw her mother sit back and looked her in the eyes. It was almost as if she was asking for permission without saying a word, and the look that Sarah gave her was a look of reassurance.

Kim looked down at the top of her step-brothers head and into his eyes which were just visible between her thick thighs. Reaching down with both hands, she wrapped her hands around his head and held him even tighter to her tingling pussy. He was not getting any air but her motions were not lost on him. She wanted him to continue. She was going to let him make her cum. His lungs were starting to scream to him. He needed to take a breath and it was rapidly getting urgent. He had to let go of her panties and shorts and try to move her enough to get some air. At first she thought he was stopping and she was past the point of letting him stop. ‘He started it’ she thought, he was going to finish whether he wanted to or not. After a few tense moments though she realized that he was trying to breath and she decided that she wanted to get her bottoms off anyway. She jumped up and off the bed and quickly pushed her shorts and panties down her shapely legs. Without a hesitation, she turned around and climbed back onto the bed, once again straddling her step-brothers head, but this time facing his feet. She noticed for the first time how red his face was and his chest was still heaving as he sucked in great breaths of air, but that didn’t stop her from lowering herself onto his face again. This time his nose slid into her ass crack as her pussy came to rest on his mouth. At least he was able to breath like this.

Tyler was still in shock over these events. He didn’t like being nearly smothered unconscious but he figured that was a small price to pay for what he was doing now. When Kim had stepped off the bed he was sure that it was all over except for the crying. He had been so out of breath at that point that he was just glad to be able to get any air. Then, all of a sudden he felt her crawling back onto the bed and when he opened his eyes he was looking up into her naked womanhood. She was looking down at him with a look of lust in her eyes and all he felt was love for her. As she settled herself back onto his face he realized where his nose was. Right at the entrance to her asshole. Any other time the thought of it would have turned his stomach, but right now in the heat of the moment, it was another turn-on. At that moment he felt something completely unexpected, a smooth hand wrapped gently around his rock hard erection. Because his face was buried under ass, Tyler couldn’t see who had his penis in their hand but he automatically assumed it was Kim. He assumed it was Kim that is until two slender hands slid down on both sides of his face and spread the ass cheeks that were caressing his face cheeks. His nose now wedged deep into Kim’s puckered asshole, he realized that the hand that was gently stroking his cock belonged to Sarah his step-mom. This was getting way more intense then he ever expected and he wondered how far it would go.

Above Tyler, Kimberly was getting close. She opened her eyes and saw that her mother was lazily stroking her step-brothers rock hard manhood. Her mother was staring at the member in her hand hungrily, as if she wanted to devour it. It was so exciting, so intense, so incredible that she started to rub her clitoris with her fingers and within moments, she started to cum. It was the most earth shaking orgasm that she had ever experienced. It kept going in wave after wave and she felt like she was going to pass out from the sensations. She let out an involuntary scream as she ground her clenching pussy down on Tyler’s face, and trickled her thick juices into his mouth. Sarah watched her daughters orgasm and was entranced. She had never seen another woman in the throes of an incredible orgasm and now she was watching her own daughter. The look of pure joy on her face, her mouth open, the flush of her skin was incredible to watch. As Kim’s orgasm died down she sat for a few more moments on Tyler’s face catching her breath.

“Mom , that was awesome. You have to try riding his face.” She started to climb off, noticing that her mom had let go of her step-brothers penis.
“Oh I don’t think that would be appropriate.” Sarah said. In reality, it did look like fun to her but she was scared of the repercussions.
“Don’t worry mom, no one will ever find out. He’s not gonna tell anyone. How would he explain that?”
Kim had a point. The embarrassment of what he’d been caught doing would be enough to ensure that he would keep his mouth shut about all of it. She had time before her husband, Tyler’s father, came home and she was so turned on from watching her daughter cum that she wanted her own release.
Tyler’s hand moved toward his recently released penis. He needed release also and was going to take matters into his own hands. Before he could though, Kim saw what he was reaching for and quickly slapped his hand away. “Oh no you don’t. you don’t get to cum until you get mom off as good as you got me off. I’ll think about letting you jerk off then, only if I think you did a good enough job.”
He heard what she said but still tried with the other hand also. He was so close to the edge that it wouldn’t take more than a couple strokes and he’d be past the point of no return. Kim was quicker though and snatched his hand up by his wrist. Quickly, she grabbed his other wrist in her other hand and slid off the bed, pulling his arms up over his head. She wrapped her long left arm around both of his wrists and in his position, he was helpless to stop her. With her free hand she yanked the cloth belt out of her shorts and quickly and effectively tied his wrists together tightly. Holding his arms over his head she motioned to her mother to climb aboard. Sarah hesitantly swung her leg over Tyler’s chest and backed up so that her ass was hovering above his head. His face was still wet from Kim’s sweat and pussy juices.

“Go on mom, do it. He needs to be punished for what he did. He deserves to get used.”
It was all the encouragement she needed and she sat herself down on her step-sons face. The feeling was indescribable, and she liked the sensation already. Tyler noticed right away that Sarah’s ass was wider and a bit more flabby than Kim’s athletically toned ass. This ass had more cushion which felt better, but the trade off was that it was more difficult to breath. Sarah adjusted herself so that her cunt was lined up with his mouth and once again Tyler found his nose uncomfortably close to another asshole. With his arms secured over his head and behind Sarah’s back, he was helpless to change his position.

Kim climbed back onto the bed to watch the depraved scene play out. She decided to tease her step-brother some more like her mom had done earlier. Instead of stroking him though, she used one finger under the crown of his penis where the skin comes together and slowly traced gentle circles around and around. She didn’t vary the speed or the amount of pressure. It was all very methodical and intended to keep him on the very edge without letting him have the release that he needed so badly. She knew it was working to because after a few seconds of twirling her finger around, she heard him moan loudly from under her moms ass. His penis looked to Sarah like it was full of pain. She had never seen a cock head so purple, never felt a foreskin stretched so tight as the one she was working on now. It gave her a feeling of power.
Sarah was still having a hard time believing what she was doing right now. The feeling was unlike any that she had ever experienced before and she liked it, a lot. But there was a feeling of guilt in her that was eating away at her pleasure and keeping her from letting go. For several minutes she sat unmoving, allowing Tyler to use his tongue on her pussy. It felt good but it wasn’t enough to set her off. She wanted to cum. She needed to cum, but her conscience was stopping her. After nearly ten minutes of Tyler trying desperately to make her cum, his tongue was completely worn out and it was too painful to continue. Sarah was ready to call it quits to. She wanted to go into her room and finish herself in private. “This isn’t going to work” she sighed “I’m going to let him up.” Kim however, had other ideas. “No mom. You just need to use his face to masturbate yourself. Wiggle your ass around and slide up and down. He needs to suffer more. Make him suffer mom.”

Far a moment Sarah thought about what her daughter had said. As crude as it was she realized that it was right. She looked into Kim’s eyes and nodded her head. Slowly, ever so slowly she started to rock her bottom back and forth. As she started to pick up speed she began sliding back and forth from the top of his forehead to the bottom of his chin. Every time her clitoris passed his nose she was jolted with pleasure. As the pleasurable feelings grew, so did the intensity of her motions. She was lost in the feelings and had forgotten that it was a human head, her step- sons head, that was under her. It didn’t matter anymore to her. Her only mission was to make herself cum and she was quickly approaching the point of no return. Back and forth she careened on his face, sweat rolling down her breasts and dripping off her erect nipples. And suddenly she was at the peak of the mountain. She tensed every muscle in her body at once, her throbbing clitoris resting right on the tip of Tyler’s nose, and held her position for a count of three. Then the release that she had craved was upon her. Wave after wave of sensations crashed over her. Her entire being was racked by spasm after spasm of delectable pleasure. She was completely out of control of her body. It wasn’t an earth shaking orgasm, it was earth shattering, and right in the most intense wave, she gushed. Not just a little trickle like Kim though, it was a river of juices spraying out forcefully. A jet of clear fluid that completely soaked Tyler’s torso and the bad around him. It was unexpected and a large amount filled his mouth and went down his throat. He swallowed the hot musky liquid to keep from choking.
Kim was entranced by the scene she was witnessing. She was so caught up in the moment that she forgot what she was doing to his penis with her finger. She had grabbed hold of it in the heat of the moment and as she watched her mother explode and spray her fluids all over the place, her hand tensed, just a bit but it was more than enough to send him over the edge also. She felt his throbbing member lurch once and she glanced down in time to see a blast of cum squirt out of the tip and arch its way to his neck , leaving a line of sticky semen from his belly button to his chin. Instead of stroking his member through his orgasm like her other lovers liked, she just held it steady, tipping it to about a forty five degree angle. The next blast was just as powerful as the first if not more and the cum plastered her mothers tits. This was followed by a half dozen more jerking spasms. By the time it stopped, Sarah’s breasts and belly were dripping long strands of thick cum down onto Tyler’s chest.

When Tyler started to cum, he desperately wanted someone, anyone, to stroke his cock, but with his hands secured behind his head and Sarah still sitting on his face, he was unable to do anything. It was almost agony to finally reach the pinnacle, only to be deprived of the most intense feelings of his release. He wanted to cry out but at the moment he was still being smothered by the fleshy pillows of his step-mothers posterior. And then it was all over. Sarah climbed off and nearly collapsed as her legs gave out. Kim gave his penis a final squeeze, too little, too late though and watched as a glob of cum leaked out and ran down her fingers. She let it drop back onto his belly and as he started to sit up, she slapped her hand down on the center of his chest and mounted him again, this time sitting on his chest. The bed around him was soaked and she was kneeling in it but that didn’t bother her. He looked up at his older step-sister and was worried that she wasn’t done with him yet.

“So baby brother” he had always hated it when she called him that, and she did it just to spite him. This time though, it didn’t even register with him. “If you know what’s good for you, you won’t ever tell a soul about what just happened. It would be awful hard to explain anyway now wouldn’t it. And from now on, you’ve got a new position in this family, and that position is under mine and moms ass whenever we want it.” those last words she emphasized by poking her cum slicked finger on his chin and mouth. “So be prepared whenever your father’s not around, because you’re gonna have to get used to having your face attached to our asses.” she smirked down at him as she swung her leg over and climbed off the bed. Tyler sat up in his wet bed and watched as Kim picked up her clothes and Sarah made her way gingerly back toward the bathroom to presumably have another shower. As she picked up the last garment and turned to leave, she stopped and turned back toward the bed. From several feet away she flung her mothers soiled underwear back at Tyler. The undies landed on his lap and he looked down at them in confusion. “You can let that horny bastard Nathan get his jollies with those. Make sure you get the money from him because your gonna buy a new strap-on dildo that we can attach to your chin so we can have more fun when we sit on your face.” she laughed a hearty laugh and walked out of his room still naked. It was going to be a very strange summer.

The End

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