thatguywiththeface Sumtember 2019

[thatguywiththefaceOG]

Hey guys, it's been awhile. This september I'm doing a 30 day writing challenge called Smutember. It can be found here I have taken ship requests from my social media and be writing a different story for the month of September. Please enjoy

[thatguywiththefaceOG]

Cuddles-Wenpines. Request by anonymous.

Growing up, Dipper was never what you called a ladies man. So it was strange, that as a college student, he found two women who could get enough of him. Even stranger that the women in question was his childhood crush and his twin sister.

The bed bed creaked under the weight of the three. Mabel was wrapped around Dipper. She was holding him close as he rammed his cock into his sister. Dipper could hear her moaning in his ear. He couldn’t get enough of her. The sight of her naked body, the voice of her voice, craving him, craving her own brother. The way she said his name drove Dipper crazy.

“Oh, ha, Dipper, don’t stop. Don’t you dare stop.”

“Huh, huh, Mabel. I love you so fucking much. I’m gonna cum soon. Do you like that? Do you want your brother’s cum inside you?”

“Yes. Cum inside me. Cum inside your sister!”

Upon hearing Mabel saying sister, Dipper was pushed over the edge. True to his word, he fired his load right in his sisters pussy. Heavying, Dipper wanted to stay in her longing but his other girlfriend had plans.

Wendy came from behind him and pulled him down. The redhead kissed him deeply, feeling his still hard cock press against. Thank God that Dipper had enough stamina for both of them. She got off of him and crawled over to Mabel. She stuck her finger into Mabel’s pussy, still leaking ample amount of her brother’s cum, and took some for herself.

She directed the goo into her asshole, making sure that Dipper got a good look at her doing it. Dipper knew the lumberjack’s daughter enough to know what she wanted. His cock pressed against her hole. Dipper pushed more of his dick into her tart back hole. Mabel made sure to crawl forward, her mouth meeting Wendy’s lower lips. Her tongue pressed into her wet ,wanting folds. Mabel’s finger’s worked Wendy’s clit as she lapped her up. The three had made to what the lovely called a redhead pines sandwich. Wendy was brought to orgasm herself, as Dipper found himself cumming again so soon after his last orgasm. With both girls leaking his seed, Dipper fell to the bed, spent.

Mabel was the first to join him. Her thighs still sticky with her brother’s cum, face smeared with Wendy’s juices. Her arms wrapped around Dipper. Wendy soon followed suit on his other side. He loved the feeling of both their bodies. Mabel was large and soft. Wendy’s body was hard and lean, all muscles. He could feel the girls hands rub his body. Cradling each other, the three lovers all drifted off to sleep.

[thatguywiththefaceOG]

Going Further Wendipbry

Tambry had always been close to Wendy. Sleepovers and hanging out. When they grew older, they explored their relationship more. Awkward practice kisses and groping became common. When Wendy and Dipper had started in college, Tambry was very supportive of their relationship.

Wendy began to talk about how she and Dipper wanted to go further with their relationship and needed Tambry’s help. It didn’t take long to understand. She and Wendy kissed. It was more confident from when they were kids, but no less passionate. A single breast was being massaged by Wendy. Her fingers pulling the plump mound, thumb rubbing her hard nipple.

Dipper sat on the bed, a few feet away. Legs crossed, he watched with rap attention. All party members were already nude. He didn’t mind watching his girlfriend make out with her friend. It was strange but arousing.

“I think your boyfriend is lonely Wendy.”

“Let’s fix that.”

Tambry brought her face close to his. Their lips touched; Tambry’s tongue pushed into Dipper’s mouth. Meanwhile, while Tambry went north, Wendy went south. She planted a series of kisses along Dipper’s dick. As she licked the head, Dipper released a moan into Tambry’s mouth.

Wendy gave the shaft a few pumps. “You seem ready.”

Tambry was pulled onto her back by the couple. Dipper got between her legs, looming over her, cock rubbing her slit. Tambry couldn’t see any of this as Wendy’s ass had blocked her view. Fluids dripped on to her lips. She stuck her tongue into Wendy’s sweet pussy.

Dipper pushed his cock into Tambry. She gave a muffled cry into Wendy’s snatch. Tambry was being attacked on both fronts. Wendy’s juices ran down Tambry’s tongue, filling her mouth with tangy flavor. While Dipper’s dick pierced her groin. The couple worked in tandem, bringing and pulling pleasure from their friend. A wave of warmth filled Tambry as Dipper reached orgasm and cum into her. Finished, he stayed in her, and massaged her clit.

As Tambry’s tongue swirled around her folds, Wendy succumb her body and cum, squirting Tambry all over her face. Dipper’s fingers soon did their job and brought Tambry to climax. The three laid on the bed, tired.

[thatguywiththefaceOG]

She Ra No Regrets-Adora/Glimmer/Bow

It started with a clumsy kiss. The best friend squad sat on Glimmer’s bed, hanging in the air. She and Adora shared another. Adora’s life changed so much since joining the rebellion. The trio awkwardly pulled off their clothes, which was difficult because everyone dressed in complicated layers.

Adora’s tepidness increased with her nakediness. A blush spread across her body. Glimmer noticed.

“ Adora, our you alright?”

“It’s just that I've never really done something like this before and I know I look weird.”

“What? Adora you’re hot! Bow is she hot?”

“Totally.” Bow sat their, cross-legged, hands cupped over his erection. “But if you’re not comfortable, we can stop.”

“Yeah, we would never want to do something you would be uncomfortable with.’ She brought in Adora for a hug. Bow joined in on Adora’s otherside.

She placed her head on Glimmer’s should. She took in the feeling of Glimmer’s skin against her own. The warmth of Glimmer’s skin filled her heart. “Thanks guys. I think… I think I can do this.”

“If things get too intense, or you get uncomfortable, just let us know. And we’ll stop.”

Adora looked into Glimmer’s eyes and gave her a stronger, more confident kiss. The kisses traveled down Glimmer’s body. After a series of kisses across her stomach. She reached Glimmer pussy. Her wet puffy lips was framed by curly pink hair. After a beat, Adora ran her tongue over Glimmer’s welcoming sex.

A cry escaped Glimmer’s lips. Adora technique was clumsy, but she made up for it in eagerness. While Adora was exploring down south, Bow crawled to Glimmer’s head, leaving his erection in her face. She opened her mouth, allowing him to slide his rod in. Glimmer was being stimulated at both ends. It wasn’t long until she reached climax. A flood of vaginal fluid sprayed Adora in her face.

“Oh my gosh! Adora are okay?” Glimmer rushed to comfort her friend, handing her a towel.

Adora wiped her face. “I’m fine, I just didn’t expect it to, you know, fly in my face like that.”

“Yeah, I’m a squirter,” Glimmer admitted. She pulled Adora in for another hug.

“Did...did it feel good?”

“Adora. It felt amazing! Are you ready for your turn.”

Adora took a big breath before answering. “Yes.”

Glimmer sat down with Adora laying down in her lap, using her stomach as a pillow. “Spread your legs.” The sparkling princess told her. She obeyed. Bow crawled to between her legs. His length slide along her wet sex.

“I’ve heard it hurts the first time.”

Bow contended rubbing as her explained. “Yes it can hurt, even bleed the first time, but if you’re careful enough.” He gently inserted himself into her. “All that can be avoided.”

Bow was right it didn’t hurt, but it was a lot. New sensations filled Adora’s body. He went slow, as not to overwhelm Adora. She moaned at the feeling of penetration while Glimmer petted her head. As Bow increased his speed, Adora’s breath grew heavy. It wasn’t long until Adora felt Bow cum inside her.

The dance continued in the night, at the end the best friend squad cuddled together. Glimmer pulled in Adora. “Any regrets?”

Adora felt herself smile. “No.”

[thatguywiththefaceOG]

Tickle Me Gravity Falls Mabifica

Pacifica exhaled a deep breath as the hot water ran down her naked body. God it felt so good. Her shower was large, large enough for several people. It was square, with a glass door, two glass walls, set up a thick brick wall.

Pacifica looked down at her body. It was fine although she felt her butt was too big. Her wife instead it looked great, but Pacifica couldn’t help but think that she had alternative motives. As she bent down to lather herself, she felt fingers crawl up her buttcheek. After a giggle escaped her lips. She snapped up straight.

“Mabel!”

The blonde turned around and saw her wife standing there with her big doofy grin plastered on her face. “I decided to join you.”

“I noticed.” Pacifica looked over her wife. As opposed to being blessed with a fat ass like Pacifica, Mabel’s breasts had grown quite large. Even bigger than Mabel’s head. Pacifica couldn’t help but notice the hot water running down her cleavage. “What have we talked about tickling me?”

“Oh come on Paz, we both know you love it.” Mabel reached out her right hand for another attack. Pacifica backed away.

“Ah!” Mabel’s boobs dangling down as Mabel bent down for a better entry of attack. The blonde smirked to herself. “While then, let’s see how you like it!”

Unprepared for her wife’s attack, Mabel fell on her butt as Pacifica unleashed her tickle attack over her boobs. Pacifica stood over her, Mabel helplessly giggling as fingers danced over her large breasts. She decided to explore Mabel’s body more. Fingers ran down her thigh, Mabel shivered when she felt fingers on her vagina. Pacifica stuck her fingers in there. Mabel was wet and it had nothing to do with the shower. As she pleasured her wife, Pacifica felt some satisfaction.

Mabel’s juices flowed out as she climaxed. “Huh, huh. No fair. You cheated.”

Pacifica leaned against the brick wall of their shower, spreading her legs. With her fingers she opened her slit, showing the wet pink folds. “Well, why don’t I give you a turn.”

Crawling toward her, Mabel orally pleasured Pacifica. The blonde petted Mabel as she ate her out. Her pussy soon clenched as she climaxed over her wife’s tongue. As Mabel finished, she lifted her head. Pacifica bent down and kissed her.

“Your face is a mess.”

“Well it’s a good thing we’re in the shower.”

[thatguywiththefaceOG]

Gravity Falls Wendy/Mabel First Time

“So you’re still a virgin?”

“Yes, Wendy. It’s not a big deal.”

The now adult girls had taken a break from their lives to meet up for old times sake. Mabel had driven up from her North Californian college up to her old summer stomping ground of Gravity Falls. A long drive, but it was worth it to see her favorite redhead. Wendy was just amazing as ever. She had grown into a lean, muscular body. But that still couldn’t compare to her sparkling eyes, framed by her flaming red mane.

As they talked about how their lives were going, the discussion lead to boys which lead to their sex lives, which Mabel’s was nonexistent.

“Nah, man. I don’t mean to judge. I’m just surprise is all. Personally, I’d like explode without any sex. Bet you hand is sore from all the jilling off you do.”

“Ah, what?”

“Jilling off? It’s the girl version of jacking off. You know, masturbating.”

“What? No. I never… done that.”

“You’ve never masturbated?”

“I don’t know how.” Face red, Mabel turned away, too embarrassed to look at her friend. She really didn’t like where this conversation went.

“Hey, it’s no biggie.” Wendy jumped on a log, unbuttoning her jeans. “Here I’ll teach you.”

Panicking, Mabel looked around the forest they were in, terrified that they would be seen. Wendy had finished pulling down her jeans and kicking them off. Her crotch was a forest of red hair, her shiny pink lips showed how excited she was.

Wendy stuck her fingers into her hole, juices dripping down. Between heavy breaths she said, “The most important part is your clit, this little guy on top. This is where your orgasm is gonna come from.” Grabbing her friend’s hand, she guided it to her sex. Mabel nervously poked Wendy’s pussy, invoking strange noises and gasps.

Mabel looked up at Wendy’s flushed face. “Does this feel good?”

“Mabel, this feels amazing.” The redhead pulled Mabel’s face closed and pressed their lips together. Mabel parted her lips, allowing Wendy’s tongue to enter her mouth. There faces parted, a line of spit still connected their lips. “Would you like to feel amazing?” Mabel only nodded.

Wendy pulled her in, kissing her deeply. Her hand found its way into her pants. Mabel had never felt anything like it. Her body quivered with pleasure as Wendy brought her to orgasm. Exhausted, Mabel laid on the log, trying to catch her breath. She was still wrapped up in Wendy’s arms, while Wendy peppered her face with kisses. This was Mabel’s first time. And it was the first of many.

[thatguywiththefaceOG]

Adventure Time Finntress First Time

Finn and Huntress’ date was going how it normally goes, heavy making out. Huntress patted Finn’s crotch. He pushed her away.

“I’m sorry. I went too far.”

“No, no HW, I’m not angry, I just didn’t expect it.”

“It felt right to me. Did it feel good?”

“Yeah.” He leaned in for another kiss. “Could I touch you?”

“Yes.” Huntress undid the laces on her tunic, and let it fall off, exposing her breasts to the adventurer. His hands wrapped around her orbs. The warm flesh of his left and the cold metal of his right. While they kissed some more, Huntress Wizard undid Finn’s pants, pulling them down.

“Do want to you know go all the way?”

“Yeah, I think we’re ready for tier 15.”

“Tier 15?”

“It’s a Jake thing.”

“Have you ever ‘reached Tier 15’ with anyone?”

“No, no. You would be my first. You?”

“You would be my first too.”

It was a moment before the two lovers continued. Huntress Wizard laid on her back pulling her pants down. Finn loomed over her, pulling his shirt over his head. Both were caught off guard by the other’s nudity. HW’s nipples were hard, her pussy wet. Meanwhile, her eyes were drawn to his erection.

His throbbing member pushed passed her lips. She let out a gasp as she was entered for the first time. The forest was filled with the soft slap of flesh meeting flesh. Her arms pulled him close. Penetration didn’t hurt, but it felt strange. Huntress Wizard and inserted things into herself before but this felt different. The otherness and warmth that Finn’s penis filled her with was titillating. She knew that Finn was reaching climax by his increased speed. His breath grew shorter with each thrust.

And true to her suspicions, Finn came. She loved the warm feeling that him filling her gave her. Finn gave a last few thrusts before stopping. He stayed in her, both of them catch their breaths.

[thatguywiththefaceOG]

Untied Kim Possible Kim/Ron

“This is embarrassing,” the famous heroine muttered. Kim and Ron had done there thing and saved the world again and gave the bad guy and their goons over to the authorities. And lo and behold Kim set off a trap, getting trapped in a freaking net of all things.

Her dedicated boyfriend was working on getting her out. “Don’t fret KP, these things happen.”

“Yeah too you maybe,” Kim pouted.

“Ah, none of that KP. And seem to remember a certain cheerleader enjoying being tied up.”

“Ron!”

“Ah come on Kim. Everybody’s gone. We’re all alone.”

Kim bit her lower lip. “Fine.”

Ron undid her baggie pants, letting them fall to the floor. Fishing his cock out, he walked behind Kim.

“Agh, Ron you are such a tease.”

Ron could help but grin. He pushed his dick between her thighs. He began thrusting away. Kim could see his dick head peeking out. The couple filled the abandoned lair with animalistic grunts. Ron’s milky seed squirted across her stomach.

“Okay, that was fun. Now untied me Ron.”

[thatguywiththefaceOG]

Superman Quickie Lois Lane/Superman

“Come on Clark. It’ll be quick.”

The famous reporter was on her knees, face rubbing against Superman’s tights. Superman, however, wasn’t so sure.

“Lois, you know how I feel about doing it in the suit.”

Lois laughed. “Ever the boy scout, huh Clark.” She rubbed his hardening cock. “Just a bj? Please?”

He looked at his wife and let out a sigh of resignation.“Fine, you win.”

She fished out his rod of steel from his famous red shorts. The appendage felt warm and firm in her hand. She teased the head first. Her tongue swirling the tip. She loved watching Clark’s face contort in pleasure.

She took about half of him on her first go, which was a lot. Superman’s cock was as thick and long as you would imagine. There was no way she could take him all, but she could try As the drool pooled down her chin, she gorged herself on Kyptoian cock. As she gleefully bobbed her head on and down Clark rested his hand on her head. Keeping himself steady.

“Lois, Im-I’m close.” She took that as initiative to pick up speed. He climaxed, shooting his milky speed to his wife’s mouth. It became too much and she pulled him out. His still firing dick coated her face with thick white goo. The semen dripped down her face to her blouse.

“Lois! I’m sorry.”

“It’s fine Clark, it’s an old blouse.”

“You might want to shower.”

[thatguywiththefaceOG]

The Loud House Luna/Sam Do That Again

“Agh!” Sam shouted in surprise.

Luna freaked. “Sam! Was that too weird? It was too weird. I’m sorry.”

“Do that again.”

“What?”

Sam turned to face her girlfriend. Her face was red from embarrassment. “Luna, do that again. I...I liked it.”

Luna was peppering Sam’s back with kisses, going lower and lower. When she reached the bottom, Luna decided to try something and ran her tongue down Sam’s ass crack. And it seems that Sam liked it. So she did it again, eliciting a moan from her girlfriend.

“Deeper,” Sam pleaded.

Luna spread her ass cheeks, revealing her brown little hole. She swirled her tongue around the edge. Pressing her tongue deeper to the anus, Luna inserted two of her fingers into her girlfriend’s wet sex. The room was filled with slurps and groans as Luna continued.

Fortunately, Sam kept herself clean down there, so wasn’t an unpleasant taste. But this wasn’t about taste anyway, it was about the sensations and the act. Sam’s whole body clenched as she climaxed. Spit dripped down her ass cheeks, mixed with the vaginal fluids she discharged.

“Whoo, that was intense,” Sam muttered.

Luna wiped the spit of her face. “You okay babe?”

“Yeah, just need to rest up a bit. Love you.”

“Love you too.”

[thatguywiththefaceOG]

Gravity Falls Tangled Wendip

There was always a risk when playing twister with a cute girl. “Okay left foot blue. Come on Dip, you can do it.” Dipper moved around the redhead, hoping upon hope that Wendy did not notice the boner in his pants.

“Right hand yellow.”

Wendy reach over, boobs pressing against Dipper’s face. “Left hand green.”

Poor Dipper had difficulty finding his spot with a face full of lumberjill boob.

“Right foot red.” Wendy was much more nimble due to years of lumberjack training. Dipper’s face was freed from her chest, but now her ass was resting on his crotch. His erect crotch. Panicked, Dipper slipped.

“Oh god, Wendy! I’m so sorry.”

“Sorry for what dude. I love it when a cute boy compliments me." She removed her flannel, feeling his manhood through the jeans. “How about the next round, we go all natural?”

Getting tangled with Wendy, sounded like a good time for Dipper.

[thatguywiththefaceOG]

She Ra Guided Adora/Glimmer/Bow

It had been a few weeks since the best friend squad took to relationship to the next level. Between missions the three explored their bodies and pushed their limits.

It was dark out in Brightmoon, all had gone to sleep except for a few guards patrolling the grounds. The only light lighting Glimmer’s room was the moonlight. If any guard had peeked in the window they would see the princess and her friends were very much awake.

Adora poured oil down Glimmer’s backside. Adora had always found Glimmer’s bottom imitating, more so up close, shinnying with oil. Spreading Glimmer’s cheeks, Adora rubbed the oil in.

“Are you ready?” Adora asked.

“Yes.”

Glimmer let out a gasp of surprise as Adora’s index finger entered her rectum. She slowly pulled in and out, playing with the sensations. She soon added a second finger. Glimmer’s grunts became more intense. Pulling her fingers out, she turned to Bow.

“She’s ready.”

Bow was stroking his erect cock. We walked over and Adora took his shaft in her hands. She guided him to her anus. Glimmer grunted as the tip entered her. She let out a long exhale has Bow pushed himself in. Eyes wide, Adora watched as she took more and more of the cock in her ass. The oil really helped him slide in.

Once about half way through, Bow pulled a little way before slow pushing back in.As he repeated he picked up speed. With each thrust he pushed in deeper and deeper. He found his pelvis slapping against her cheeks. The thud of meat on meat filled the room along with their moans and groans.

Adora was cheering her friends on as they took carnal pleasure from each other.

“Come you can do it. You can take it.”

“Oh, B-bow. You feel so good. So fucking good.”

“G-guys, I’m close.”

“It’s o-okay. You can cum. Cum inside me.”

Bow deep just that. Grabbing her booty, he milked himself with his friend. Still hard, he pulled himself out, letting his cum dribble out of Glimmer’s ass.

[thatguywiththefaceOG]

Kim Possible Kisses Kim/Ron

Steamed filled the bathroom as Ron filled the bathtub. He tested the water. It was warm but not too hot. He disrobed and sank into the tub.

As he was soaking, his wife walked in. “I can’t believe you still take baths. How do you have time to lounge around? Showers are much more efficient.”

“Come on Kp, nothing wrong with taking your time. Sometimes you gotta relax.”

Kim gave Ron a coy smile. “Fine.” She slipped off her top.

“Kp?”

Pulling her pants down she said, “What? I’m joining you in relaxing.” She stepped in, slipping water down to the floor. “Uh, it’s a little tight.”

“Yeah Kp, that’s what happens when two people try to fit into a small tub.”

“This is why showers are superior.”

Ron gave Kim a kiss. Laughing, she kissed him back. There kissing evolved to full blown making out. She could feel his tongue in her mouth, his hands on her back, and his dick poking her in the stomach.

With her free hand she took the member in his hand and began stroking it. She felt Ron moan into her mouth. She picked up the pace with agusto. Eventually Ron climaxed, his milky fluids filling the tub.

Ron looked at his hand. “Okay Kp, I’m getting pruney.”

“I told you showers are better.”

[thatguywiththefaceOG]

Phineas and Ferb Slow It Down Canderemy


“Candace, Candace, Candace! Slow it down!”

Candace came to a complete stop. Her boyfriend, Jeremy, laid underneath her. “Baby are you hurt?”

“No, no. It’s just that you were riding me pretty hard.”

“Heh, heh. Yeah. I can get pretty intense. So you wanna stop?”

“No, no. But maybe we should take it slow and go gently.”

“Okay.”

Placing a hand onto his chest. Candance began riding herself onto his cock. As per Jeremy’s request, she took it nice and slow. She rose herself up and down on his shaft, savoring the sensations that were flooding her body. Her chest rose with each slow steady breaths.

Jeremy, for his part, was not taking an inactive part in their lovemaking. His hands were all over Candace’s generous ass as he bucked into her.

Feeling the pressure building in her groin, Candace braced for her orgasm. She let herself succumb to the pleasure and collapsed onto her boyfriend. Jeremy soon followed.

“See,” he told his girlfriend. “Going slow can be fun.”

[thatguywiththefaceOG]

Hey Arnold Hand Over Fist Shortaki

She’s trying to kill me was all he could think. I’m dying. I’m going to die. Helga Pataki had finally managed to kill him. Death by sex. How humiliating. At least Grandpa would get a good laugh.

“Oh, faster Football Head, faster.” She peppered his neck and face with kisses.

“Helga, please. Let me rest.”

“Nyaha. We are going to go hard, and we are going to go fast. You got that Football Head. We’re going hand over fist”

Arnold let out an exhausted sigh. “Whatever you say Helga.”

He doubled his efforts. Rapidly plunging himself himself into the love of his life, he brought Helga to full ecstasy. Arnold could feel her cuming along his dick. Slamming into her, Arnold erupted into her.

Helga’s eyes rolled in the back of her head, unable to speak.

Arnold found his voice. “Fast enough for you Helga?”