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Sean From High School

"After years of hot sexting, a rough night of fucking turns into a romantic morning of lovemaking."

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5.3k words 5.3k words
Competition Entry: The Moment You Knew

Author's Notes

"This story is inspired by several people, including: the guy I sext whenever I have a breakup, my last two ex boyfriends, my current boyfriend, and some random guy I met at a friend's birthday party in 2015."

She always hit Sean up after a break-up via SnapChat...And this time she was getting divorced. The ultimate break-up. They were together for two years and married for one when she discovered several videos of her husband's "friend" Annie touching herself on his phone. Annie. His "lesbian" friend. She left him in the middle of the night, leaving behind a note that just said, "Fuck you and Fuck Annie." She stayed with her mom for a little while, and then decided she needed a change of scenery. Her dad's whole side of the family was still in Orlando, and Orlando is one of the best places for an idiot who studied dance in college to be. She made all the arrangements, and about a month before the move, she snapped Sean.   

SarahTyler: Hey. I'm single again. I've got my vibrator out and ready to go. You down? 

She turned on the vibrator and pressed it to her clit, anxiously waiting for a response. It took all of two minutes for her phone to buzz. 

SeanJohnSilver: Hell yeah. You start this time (; 

SarahTyler: Okay. I want you to throw me up against a wall, put one hand around my neck and then finger me with the other.

SeanJohnSilver: Mmmm hell yeah. 

SarahTyler: I want you to bite my neck and suck on my nipples. 

SeanJohnSilver: I'm gonna fuck you in missionary while I do that. 

SarahTyler: Good. Then I want you to bend me over the bed/chair/desk WHATEVER THE FUCK IS CLOSEST TO US and hold my hands together behind my back while you fuck me. 

SeanJohnSilver: I wanna see what you're going to look like when you suck my cock.

SarahTyler: I wanna see your cock right now. 

They both complied. He sent a dick pic. She sent a selfie from a high angle, mouth open and eyes begging, "fuck me, Sean." He had that effect on her, even from all the way across the country. 

SeanJohnSilver: God you're so fucking hot. 

SarahTyler: and what are you gonna do about it? 

SeanJohnSilver: I'm going to go really slow while I look you deep in the eyes and kiss you, slowly sliding my cock in and out of you so I can feel every inch of your tight pussy wrapping around me.

That sent her over the edge. She managed to grab a video of herself cumming so she could send it to him. 

SeanJohnSilver: God you're so sexy when you cum. 

SarahTyler: fuckmefuckmefuckmefuckmeFUCKME. 

SeanJohnSilver: I'm going to throw you on the bed and bend you over. Then I'm going to tie your hands behind your back. I'm going to tease your tight little pussy again by sliding the tip in and out until I slam it in balls deep. I'm going to grab your hair and pull you upright while I'm still fucking you and kiss you. Then I'm going to throw you back down on the bed, lay you on your back and slide back in. I'm going to slide in and out of you slowly and tell you how much I love being inside you. With every thrust, you can feel my cock throbbing just waiting to explode. I'm going to put my hands around your face and look into your eyes and thrust as deep as I can. You can feel my throbbing cock shoot spurt after spurt of cum deep in your pussy. 

She was edging herself while reading that entire paragraph and finally allowed herself to cum when she finished it. She managed to catch another video of her orgasm face for him (which she thought was rather cute.) He loved it, as always. 

SarahTyler: ...So I'm actually moving back to Orlando in about a month. 

SeanJohnSilver:...You're not pulling my leg, are you, Ghost? 

She smiled. Being one of the palest girls in high school, "Ghost" became her nickname. She didn't mind since it was in jest. She was porcelain-skinned with chestnut brown hair, big blue eyes, and a curvy figure. 

SarahTyler: I'm completely serious. 

SeanJohnSilver: I'll believe it when I see it. 

Sarah couldn't sit still on her flight. She thought about taking a few minutes to excuse herself and masturbate in the bathroom, but she had explicit instructions from Sean to not touch herself until they were together. That day was finally coming tomorrow. She could hardly stifle her excitement. She was shipping her car from Michigan, so she needed a rental for a few days. She couldn't stop thinking about Sean for even a second on the ride to her new place. She had been perpetually wet for the last month. She tried to focus on unpacking and decorating her apartment, but it was hopeless. She wondered if twenty-five was too old to still have tapestries in her apartment, but then she decided, "Nah." She was a stoner, so tapestries can be expected. She didn’t know whether or not Sean smoked, but she’d find out soon enough. She packed a bowl, got a little stoned and danced around her apartment while she decorated, all while thinking about Sean and how he was going to (hopefully) rock her world. 

The next day at around 3:00 pm, she received a text after hours of pacing around, waiting for him to text her. 

SeanJohnSilver: Be ready at 6:00. 

Oh, she would be. She had already showered and shaved every single hair off of her pits, pubes and legs. She DOUSED herself in various lotions and perfumes, and she made sure that, while the outfit was casual, (Shorts and a tank top. Simple but still sexy,) she made sure her hair and makeup looked PERFECT, even though she knew all of her hard work was going to be just as destroyed as her cunt by the end of the night. She finished (most of) the unpacking and decorating, and let out a satisfied sigh. The apartment looked cute. It felt like home. 

She heard a knock on the door at around 5:40. She answered, and he embraced her with a huge bear hug and then looked her up and down. 

"Damn, Ghost, you're even sexier than I remember," he smirked that killer smirk. She pretended like her heart didn't just skip a beat because of his smile. 

"You literally watched me cum on camera like a month ago." 

He laughed. She was just like he remembered her. Sassy. 

"It's different in person...Like, wow, Sarah. You're a smokeshow." 

She didn't want to blush, but she did. 

"So where are we going?"

"Just back to my place." 

"Perfect." 

They got in the car and just stared at each other for a while. He couldn't wait to see her mouth around his cock. Couldn't wait to touch her, to taste her, to fuck her. To finally be inside her. After a minute or so he popped the car into drive and headed down the street. They made small talk. They talked about their various college experiences, and he filled her in on all of their mutual acquaintances from high school. Kris got arrested for slinging coke, Will knocked up Katherine, Jenny opened up her own hair salon, and Alexa was running for Mayor. At the first red light, he pulled her in and kissed her. She melted into the kiss. Most of the men she'd made out with were shitty kissers, but Sean knew what he was doing. He kissed her mouth, then her cheek, and then whispered in her ear,

"There's a towel in the back seat. I want you to take off your shorts and cover yourself with it."

She didn't need to be asked twice. Within a minute she was out of her shorts and under the towel, still in her little red thong. He rubbed along her legs, up and around her thighs, occasionally brushing up against her most sensitive parts, but never actually touching them. She let out a moan.

“Calm down, Ghost. We’re not there yet.”

“Can we get there?” She said, impatiently.

He crept his hand right where her pussy met her thigh and let it linger.

“Sean.”

“What do you want?”

“You know what I want.”

“Tell me what you want.”

“I want you to play with my pussy.”

“Say please.”

“Please, Sean. Please play with my pussy.”

He moved the little thong over and started rubbing her clit in slow circles. Having not masturbated in a month, the sensation was intense.
 
“Good Girl.”

She felt those words course through her entire body, but she refused to cum. It was too soon. They approached a red light and he stopped immediately. That was so much worse than cumming early. She let out an impatient whimper.

“Sean.” She reached for his hand.

“Nope. Red means stop.”

“SEAN.”

He waited with a cocky little smile on his face for the light to turn green. God, he was cute. Perfect smile. Not very tall, probably around 5’8, but it didn’t matter. She was only 5’1 so most guys were taller than she was. He had dark brown hair that was styled well, but she knew it was going to be a tousled mess once she was done with him. Piercing blue eyes. Or maybe green? It shifted in the lighting. 

Speaking of green, the light changed and he was right back under the towel. He dipped two fingers into her pussy and she jolted at the sudden penetration. He moaned out, too.

“God, Sarah. Your pussy feels so nice.”

“Your fingers feel so nice.”

“Yeah?”

“Y-yeah.”

He traced his fingers out of her hole and back to her clit. She moaned out.

“Yeah, you like that?” He prompted.

“I f-fucking love it,” She said, inching closer and closer to the edge of her first orgasm.

“You gonna cum?” He asked, that smug smile spreading across his face again.

It was getting hard for her to fight it.

“I think so.”

“Cum for me, baby.”

That was it for her. She’d always hated when a man asked her to cum for him because it never worked. This time it did. She shook in the passenger seat and held onto the door handle for dear life. He laughed and continued to rub her sensitive clit, this time picking up the pace.

“Oh god, Sean.”

Second stop light. Before she could say, “Don't,” his hands were back on the wheel. He looked at her as if to say, “I control you.” It lit a fire in her core. The light turned green and he put his hand back on her pussy.

“You’re going to have ten orgasms in twenty-four hours, Sarah. Mark my fucking words,” and continued his assault on her clit.

“Ohhh FUCK, Sean, that feels so fucking good.”

“Oh, yeah baby.”

“I want you to do everything to me.”

He stopped in his tracks.

“…Everything?”

“Yes!”

“…Anal?” He joked. She had never liked anal. She always told him no when he tried to bring butt stuff into their sexting.

She’d had an aversion to anal sex ever since she had a failed attempt a few years back. There wasn’t any lube, and the other person was just as inexperienced as she was. Lately, she’d started watching porn involving anal sex. She didn’t know why, but it fascinated her, and she’d decided that if anybody was going to change her mind on the subject, it would be Sean.

“Yes. I want you to fuck my ass, and I want you to fuck it good.”

His face lit up, and he went back to her dripping snatch. He wasn’t pulling any punches at this point. She was so wet, and he was rubbing furiously as she bit down and moaned through gritted teeth. Her second orgasm tore through her right as they entered the parking lot to his apartment complex. She put her shorts back on, panting and ready to get inside.

Time spent together: 0.25 hours
Orgasms achieved: Two.

 


The minute they stepped into the studio apartment, he immediately grabbed her and threw her against the wall. He lifted her up and she wrapped her legs around his waist, grinding against the hardness in his jeans.

“God I can’t wait to fuck you,” he growled in her ear, animalistic this time.

“I can’t wait for you to fuck me,” she said with bated breath, kissing his neck.

“Oh, fuck yeah,” he whispered, grinding against her and kissing her.

They dry fucked for a few minutes, moaning into each other's mouths with anticipation before he carried her to the bed. On the bedside table, she noticed a vibrator and a set of handcuffs. Her excitement tripled. He went into the drawer in the table and pulled out a bottle of lube and a butt plug.

“Don’t worry. I bought these toys for you yesterday. They haven't been used.”

“Why a butt plug?”

“Wishful thinking,” he said, leaning down and kissing her. He circled the bed, looking at her like a hungry tiger as he removed his shirt.

“Holy shit,” she said, gawking at his hot-ass shredded body. She’d seen a bunch of photos of it at this point, but those photos couldn’t hold a match to the real thing. Her jaw about hit the damn floor. 

“You like what you see?”

“Get the fuck over here,” she pulled him on top of her, and he yanked off her shorts and thong again. Her breath hitched in anticipation as he circled her clit with a finger and felt up her shirt to caress her breasts. He lifted her shirt and bra so he could get a good look at her.

“God, Sarah, you have gorgeous tits.”

“You’ve said that before,” she teased.

“Yeah but, in person,” He groaned, taking a nipple into his mouth, “It’s a whole ‘nother story, baby,” She moaned a little as he alternated between nipples, still rubbing her pussy. He stopped to remove her shirt and bra completely, and then just leaned back and stared at her in awe for a moment.

“You,” he leaned in and kissed her, “are perfect.”

She blushed again and he kissed her deeply. He then kissed his way down her neck, then her chest. He gave each breast one little bite, making her gasp. He kissed down her stomach, and all around her thighs. He stopped at her pussy and just enjoyed the view for a minute.

“Something wrong?” She asked.

“Not at all.” he groaned. “This is the most gorgeous pussy I’ve ever seen,” He kept looking at it while he started rubbing her clit again, inserting a finger into her waiting cunt. He entered and exited her slowly with his finger as she started to shake and pant. She was going to cum again, and he could sense it. He took his finger off her clit but continued fucking her with his finger as he pulled her bottom half off the bed and knelt on the floor. He licked her clit this time, slowly. She hadn’t felt a tongue on her clit in months. She let out an almost embarrassingly loud moan.

“That’s right, baby. I want the neighbors to hear you. I want them to know I’m making a beautiful woman scream.” He went back to licking her, pushing two fingers into her pussy.

“Ohhh god,” she moaned, as she shook frantically, the orgasm flying through her at light speed. She swore she blacked out for a second. By the time she’d recovered, she opened her eyes to Sean staring into hers, stroking his gorgeous cock. His eyes had turned grey in the light, and she could hardly stand it. And when did he have time to get his pants off??? Such talent.

“You look so hot when you cum.” He said.

“Yeah? Let’s see how you look when you cum. I bet your orgasm face looks stupid.”

“Oh yeah?” He said, grabbing her by the hair and throwing her onto her knees. He grabbed a fistful of her hair and shoved her mouth onto his already throbbing cock. He knew he wasn’t going to last very long. She was gagging and tearing up as he fucked her face, but she had been issued a challenge, and she never turned down a challenge. She maintained eye contact the entire time. He groaned and pumped his first load into her mouth. She was eager to swallow every drop.

Before she knew it, he had picked her up and bent her over the bed. He pushed her head into the mattress.

“So how did my face look?”

She smiled into the mattress,

“It looked pretty fucking stupid.”

She felt a hard blow to her ass and squealed with delight. That was exactly what she hoped he would do.

“Sorry, what was that?” He said, His voice almost threatening.

“Your orgasm face. Looks. STUPID,” she taunted, hoping for just a little more of a punishment.

He did exactly what she wanted, delivering five more HARD blows to her sensitive cheeks. She pictured the redness and handprints he must have been leaving and felt her pussy throb. She heard the vibrator, and then he heard him turn it up to the highest speed. He stuck it between the mattress and her pussy, resting it against her clit. She shuddered. She felt the cool metal of the handcuffs around her wrists, snapping shut. He knelt down and pulled her ass cheeks apart. He groaned.

“Jesus, Sarah, you have such a nice ass. Every part of your body is just perfect,”  He said, kissing both cheeks before licking her tight little asshole. She inhaled sharply, taking in the new sensation. It was good. No, scratch that, it was great. She couldn’t believe how much she was enjoying it. He stuck two fingers into her pussy as he ate her ass, the vibrator still expertly placed on her clit. It was too much and she came again, all around his mouth and fingers. He laughed and she heard him pop open the bottle of lube. She inhaled sharply. He could tell she was nervous. 

“Don’t worry, baby. I’m going to take care of you.”

 She felt the cool liquid fall onto her ass as he massaged her tight little hole, sliding a finger in. He kept doing that, just sliding one finger in and out as she adjusted to the sensation. He knew exactly what he was doing. He put two fingers from the other hand into her pussy.

“Oh my god, Sean. This feels-“ she couldn’t even finish the sentence before another orgasm decimated her. He laughed again. He was loving this. She was dumbfounded, disoriented. Nobody had ever gotten her off this many times in a day before. She wondered if he was going to actually make do on his promise.

“Hold still, “ he said, dripping more lube onto her ass. He held her on the bed by her back to keep her steady while he slowly inserted the butt plug. It…surprisingly didn’t hurt at all. It just made her feel full. He then positioned himself behind her, rubbing his dick up and down her slit, the vibrator still tickling her clit in the most divine way. He pushed just the head of his cock in, causing her to moan in frustration.

“What do you want?”

“You know what I want.”

“Tell me what you want.”

“I want you to fuck me.”

“Like this?” He asked as he continued to just push the tip in and out, driving her mad.

“No, not like that!”

“Like this?” He asked again, pushing just a little more of his cock in and out of her.

“I hate you so much,” she said. She wanted to punch him in the face.

“Tell me. Exactly. What you want.” he commanded, smacking her ass again. She yelped.

“I want you to FUCK me, Sean. I want you to shove your entire cock in me and fuck me like there’s no tomorrow!”

“Good girl.”

He laughed and shoved his cock inside of her as hard as he could and started fucking her frantically, like an animal. His balls slapped against her ass as she cried out,

“OH, FUCK YEAH, SEAN! FUCK ME! GIVE ME ALL YOU’VE GOT. I FUCKING LOVE IT!”

He continued to pump into her harder and faster than she’d ever been fucked before. His groans and growls were so fucking sexy and she exploded again. Unbelievable. This guy was magic. His hands were magic. His tongue was magic, and most importantly, his cock was magic. He felt himself ready to bust, but he wasn’t ready yet. He needed a moment, and he knew exactly how that moment was going to be spent. He was terrified of what he was about to do, but he needed it. He undid the handcuffs and tossed her onto the bed on her back. He switched off the vibrator, climbed on top of her and looked into her eyes.

“You know I’ve had a crush on you for a long time now,” he said.

“You’ve mentioned that once or twice, yeah.”

“Well, it goes a lot deeper than that.” He was nervous. She could tell. “I’m in love with you, Ghost. Hell, I’ve been in love with you for a decade.”

“Since sophomore year, really?”

“Yes. I never said anything because you were always dating some guy named Ben.”

She cracked up. She only dated two boys in high school…both named Ben. She couldn’t believe he remembered that after all these years.

“Sean, I always thought you were really cute. Always. I don’t know if you remember, but Ben and I…The second Ben…were on-again, off-again, and I’d always hoped that you’d do something in those off-again times, but you never did.”

“I was nervous. I thought it would be safer to have you as a friend than to date you and potentially lose you forever in a breakup. I wish I’d said something.”

“I’m glad you didn’t. You’re right. There’s a really good chance that we wouldn’t be here now.”

He hesitated, “Sarah, I love you. I’m so glad we’re together right now.”

“Love” was a strong word for her right now. On one hand, she was fresh out of a breakup and the wound from that was still fairly deep. On the other, she was feeling a very intense connection with Sean. She pondered what to say for a moment before he spoke up,

“You don’t have to say it back. I just wanted you to know,” and he kissed her forehead.

“Love is honestly a strange concept to me right now. But I love this. I love being with you. I love having sex with you. Just give me some time. I’m definitely falling for you, I’m just not there yet.”

“And that’s completely fair,” He said, now ready to continue. 

He moved her so her bottom half was off the bed again, and licked her clit slowly as he turned the vibrator back on and fucked her with it. His words rang in her ear, “I love you,” and she was so overwhelmed by the feeling those words gave her that she came again, harder than all of the other times combined. He then slowly removed the butt plug, and she knew exactly what was coming next. He grabbed the lube, applied some to his cock and applied more to her asshole. She gulped. He noticed the fear in her eyes.

“Shhh, baby. Don’t worry. It won’t hurt, I promise, and if it does, just tell me and I’ll stop, okay?”

“…okay…”

He looked her in the eyes, kissing her passionately as she wrapped her legs around his waist and he aligned his cock against her little opening.

“Hold this against your clit,” He said as he handed the vibrator off to her. She pushed it onto her clit, starting at the lowest setting. 

He pushed into her just a tiny bit and she gasped. It did hurt. It totally hurt, but she wasn’t going to tell him that. It was a good kind of hurt. It hurt so good. He slowly inched more and more of his cock into her, letting her adjust to him as he went along. She increased the speed of the vibrator every time he got further inside. They rocked along like that, never breaking eye contact until he finally had his entire length inside of her. He took the vibrator and put it inside her pussy, pushing it in and out of her with this thrusts to her asshole. She started rubbing her clit with her hand, and he increased the pace, pounding her sweet little ass hard and fast. They were both going crazy, fucking not only for their own pleasure but for each other’s as well. She bellowed out,

“Yes, Sean! Fuck me! Fuck my ass!”

“Oh, god, Sarah.”

“Oh, god, Sean.”

“I love you, Sarah,”

She grabbed his face and kissed him hard. She may not have been ready to say it back, but she wanted him to feel it in her kiss.

“I’m gonna fuckin’ cum, baby.”

“M-Me T-t-“ She couldn’t even finish the sentence before she was catapulted into nirvana, milking his cock with her spasms, causing him to explode inside of her. She could feel his cum pumping into her, filling her up.

That was her first simultaneous orgasm. Ever. They looked at each other in complete disbelief.

And that was when she knew.

They stayed up talking and laughing until around 4:00 am when they fell asleep in each other’s arms.

Time spent together: 10.0 hours
Orgasms achieved: Seven.

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She was dreaming about Sean. They were on a roller coaster that was slowly climbing the track up to a huge drop. He was fingering her as the cart climbed further and further up the track, and right as they were about to drop, an intense orgasm pulled her out of the dream and back into reality.

She opened her eyes with Sean looking at her. 

“Good morning,” he said, removing his hands from under the covers. 

“Were you fingering me in my sleep? And watching me?”

“Best alarm clock you’ve ever had?”

“Mmmm, you’re damn right,” she said, kissing him. She grabbed the lube off the table and squirted some into her hand. She reached under the covers, finding his cock and gently stroking it.

“Oh, god, Sarah.”

“You like that?”

“I fucking love it.”

He started to make his way back down to her pussy with his hand, but she stopped him.

“Shhh, let me take care of you,” she said, continuing to stroke his hard cock. She increased the pressure and pace and made sure she was being attentive to his every little breath and moan and movement. After a while of watching him groan and his cute little face twitch, she could feel his orgasm starting to build up. She disappeared under the covers and took his cock into her mouth, sucking him slowly. She felt him shake as he came and swallowed every single drop of his cum, happy that she could please him. Happy that she had full access to him.

He grabbed her and rolled her on top of him. She rubbed herself on his cock, waiting for it to become hard again. She was at the perfect angle for them both, sliding her clit over his cock and abdomen. 

“Oh, god Sean,” she said, stimulating her clit against his hard body.

He grabbed her and kissed her as he slid her around. She quickened her pace, and with each of her moans, he became harder, and right as she came from the friction, he was hard as a rock again and ready to go. She positioned herself over his cock, sliding up and down on just the tip, driving him wild.

“Sarah.”

“What do you want?”
 
“I want you to fuck me.”

“Like this?” She teased, pushing herself just a little bit further down on his cock.

“NO, SARAH.”

“Tell me what you want,” she said with a smirk. Karma is so sweet.

“I want to make love to you. I want you to take my entire cock and ride me cowgirl. I want to make you cum for the tenth time”

She paused.

“Have…Have I really had nine orgasms?”

“You have," he said, grinding into her.

“Holy shit,” she said. She had no idea he was actually keeping track. She’d lost count.

She sank down on his cock, taking a little bit of time to re-adjust. She had tightened up a bit in her sleep.

“Oh, fuck,” he let out a little moan.

She started slowly, quickening the pace every time he made a sound until she was bouncing up and down on top of him. He grabbed her ass and fucked her mercilessly until he was about to cum again. He paused and looked at her.

“You’re incredible, you know that?”

He kissed his way down her stomach to her thighs. He licked her clit and fingered her swollen pussy. Slowly. Gently. Lovingly. What they were doing wasn’t sex anymore. They were making love. She always thought the term sounded ridiculous, but now she understood. They had formed some type of cosmic connection and he was already more in tune with her body than anyone else had ever been. When her orgasm hit, it wasn't like the other ones. It was different. It meant something.

“Oh god, Sean, I love-“

“You love what?” He said, with a knowing smile.

“I…love…when you make me cum,” She tried to save herself. It didn’t work. He knew exactly what she wanted to say.

He entered her again, missionary. They never broke eye contact as he slid in and out of her, slowly. He began circling her clit with his finger while he made love to her. It was beautiful. He increased the pace just a little bit when he was ready to cum and she felt him shake and pump her full again. God, she loved how his cock felt throbbing inside her. She loved feeling spurt after spurt of his cum shooting into her pussy. He then returned his tongue to her clit where he slowly licked and fingered her until she shook with her tenth orgasm.

They were too sore and exhausted to make love to each other again, so they just laid in bed all day, cuddling and making out, staring into each other’s eyes until about 5:30. 

“I love you,” he said.

She smiled, “I know.”

“Oh okay, Han Solo.”

“I thought you’d like that reference.”

He looked at the clock on his phone.

“Hey…our twenty-four hours is almost up.”

“Hmmm…I suppose we could grab a bottle of wine and do another 24 at my place? I caught a second wind and I kind of want you to fuck me on my kitchen counter.”

He looked at her in amazement, “Let’s go. Right now.”

“Oh, by the way, do you smoke weed? We can smoke a bowl, too, if you want.”

“God, you’re perfect.”

They got dressed and headed out the door, but not before he grabbed the lube and the handcuffs off the table.

Time spent together: 23.5 hours
Orgasms achieved: Ten.

 

 

 

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Written by smut_princess
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