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Madelaine Petsch Tries Anal Sex	By : TheChemist Category: Celebrities - Misc > Het - Male/Female Views: 5851 -:- Recommendations : 0 -:- Currently Reading : 0
Disclaimer: I do not know or have anything to do with Madelaine Petsch. These events did not happen. I make no money from this fictional story

Chapter List
- 1-Madelaine Petsch Anal
- 1
It wasn't a good start to the summer vacation for Madelaine Petsch. Even though she was making a healthy amount from portraying Cheryl Blossom on the TV show Riverdale, she had access to little of it. That was because her parents, who only had the best intentions for the budding actress, controlled her money. And though they allowed her to do things like buy a house in LA and own an apartment in Vancouver, they didn’t allow for frivolous spending. They also wanted the 22 year old actress to stay humble and grounded. And it was these two pieces of information that was the cause of why the fair-skinned, red-haired actress found herself outside in the driveway with a bucket of soapy water and 2 dirty cars in the driveway.
Having to wash her parents car was in direct response to her acting foolish last night. Though she was 22 years old, she was only in LA for 3 months a year so she still shared her house with her parents. Well, they didn’t take kindly to when Cheryl came into their house last night at 3 in the morning like a bull in a china shop even when trying to be quiet. She had also had sex with at least two random guys despite having a boyfriend, though her parents or Connor, her boyfriend, didn't know that. As punishment for being disrespectful, they punished her with a long list of chores to do, but an added wrinkle to the punishment was when her stern father woke her up at 7am with a cow bell.
First on the list was to make a big breakfast, which was eaten by the whole family. Vanessa, her mother, had to leave shortly thereafter so Madelaine had to do the dishes all by herself. Her dad didn't even allow her to use the dishwasher, she had to do it by hand and of course her siblings offered no help, whether out of their own devising or her fathers.
The day finally started to look up. While she was shining her dad's work shoes, she overheard her dad having a phone conversation with her mom. Apparently her mother was working on a big project and wouldn't be home for a long while yet. Madelaine thought nothing of it and continued her work.
"Ok. Well I have to go in to work a little early. While I'm out, you don't get it easy but I figure even prisoners are allowed outdoor time. I want you to hand wash my classic Chevy 1961..."
"The old red car in the garage. Sure dad," Madelaine cut him off.
"Less attitude too. It can sense bad moods," her father joked. "Be good and see you in a few hours. And I’ll take your car to work so you don’t run off. Plus this way you can wash my regular vehicle as well."
Madelaine may not have been book smart, but street smart was a whole different game. Though she wouldn’t have a car, she at least now had hours of free time with no supervision while all she had to make sure she had to do was wash the two cars. No easy task mind you since her dad was particular.
However, the red-haired actress quickly went upstairs and got all the things she was banned from. The TV was started up and put on Netflix, Madelaine not caring what was on. The computer was booted up and immediately she started surfing the web. Her phone was turned on and she started chatting with her friends.
"Connor," she said aloud.
The boy who had been with her for a year had texted her cell over the last 12 hours. She decided he deserved a call and a confession, though that would need to be face-to-face. She owed him that much. She may have been a slut and a whore but Madelaine Petsch was a good person with a loving heart, it was just lust was hard for her to deny.
"Hey Connor...wanna come over," Madelaine asked her boyfriend. "I have to wash my dad's car actually. Sure you can help but that's not why I called. Seriously you don't mind helping? God you're the best. See you soon, sweetie."
It took Connor about 20 minutes to arrive at the Petsch's residence, a place he had been too often. He pulled into the driveway and parked a good distance behind the two cars nearest the garage with Madelaine already outside and wetting with hose water. Due to the garage being so far recessed behind the house, coupled with the high fence and now Connor's truck, the neighbors of the populated suburb had no line of sight to them.
"Hey sweetie. Boy do you look smoking hot," Connor said as he approached her.
He wasn't wrong, not in the slightest. Her back was to him so the sight that greeted the tall man was one of pure delight. The short, red-haired 22 year old was dressed in super tight cut-off jean shorts that showed the bottoms of her large, meaty ass. She also wore a white tank top that was cut short to show off her womanly hips and flat stomach.
When Madelaine turned around to see her boyfriend, he was able to observe her from the front as well. The talented actress had a beautiful face that was natural most of the time she wasn’t acting on Riverdale, including now. It was framed by her trademark long red hair, however the thing his eyes went straight to where her tits. Large, perky C-cups, they were rivaled to be her biggest asset, along with her ass, making her a complete package.
"Hi yourself," she said, running and jumping into his arms.
"I'm gonna go throw my cell on the kitchen table so I'll be out to help in a second," he told her, patting her ass as he left.
When he came back no more than a minute later, Madelaine had his back to him again as she was taking a sponge with suds on it to the side of the vehicle. Rather than announce his arrival, Connor grabbed the running hose laying on the driveway and adopted a devious grin. He brought it to waist height then quickly flicked his wrist. The result was a torrent of water jetting onto the low back and ass of the hungover actress.
"What...the...hell babe," Madelaine turned around, annoyed.
"Hahaha I'm sorry, did I soak you," he asked, still laughing.
Madelaine took a break from washing, returning the sponge to the bucket and walked into the shaded portion of the garage. It was hot and getting out of the sun was important, especially to maintain her flawless pale complexion. Truth be told the hosing off wouldn't have bothered her in the past, but the combination of being overheated and annoyed with her punishment grated on her nerves.
"Yes! I'm fucking soaked," she fumed.
"Don't be mad honey, I was just trying to get your great butt," Connor grinned, though he had stopped laughing. "Did I get it?"
Rather then reply, Madelaine simply turned around and showed him the evidence. She didn't know how bad it would appear, but her cheeks were thoroughly damp. It must have been visually as obvious as Connor broke into more chuckles. Looking over her shoulder, Madelaine saw that the majority of the material had turned a much darker shade of blue.
"I'm sorry," Connor said, though he didn't seem it.
Madelaine tried to calm herself down, remembering why she had asked him here in the first place. She was about to break his heart and crush his soul while he was just having fun with gestures she normally would have found cute or funny. However, her attention was broken when the man, still holding the hose, flicked it at her again, drenching her chest now.
"Connor! Seriously," she huffed.
Her shirt was now soaked through, showing off her breasts beneath it. She was glad at this point that she didn't elect to wear a bra as it would have been one more thing needing to be dried. Besides, she didn't need a bra, no one did when their tits were that perky, which was rather impressive given how large and heavy they were.
"You know how hot you look when you come out of a shower," he told the vain girl.
"I do, don't I," she asked with a smile finally donning her face.
"You're darn right," he replied. "Now look how wet I got you."
Instantly he had stepped closer to the girl who was calming down. His hands touched her bare legs, slick with tap water and he noted her start to relax further. His other hand touched her meaty thigh of the opposite leg and the result was the same. This time he traced his hands up and onto her stomach, flat without the presence of any fat. How a girl with an ass that big and tits those large and round could have no belly fat was a mystery to him.
"I have to wash the car baby," Madelaine finally said when he groped her tits through the wet material of the shirt.
"How about I wash the cars for you," he said looking down at her.
"So you wash the cars and what do I have to do for you," Madelaine asked, looking over at the already soaped up vehicles before licking her lips.
"Let's see...I rinse the car and you..."
"I know how you work Connor. So let's cut to it. You do that for me and I'll suck you off," Madelaine bargained.
"Deal. You suck first then I rinse off the cars," Connor said. "But first...how about a show."
"What about the neighbors," Madelaine asked.
Her words lacked any type of conviction however. Her tone soft and playful and she did nothing as Connor's hands went to the waistband of her jean shorts. In the next moment the button was undone and he was folding the edges of the garment back.
"They can't see anything. No show for them," he answered.
Already the red underwear she was wearing were visible for Connor to see and he felt the first bulge of his erection hitting his own pants. Madelaine hooked her fingers into the undone shorts and gave them a little shake before turning around to flash her barely concealed bottom.
"Do you like my ass," she asked over her shoulders before lowering them.
"Oh God yes! It's so amazing," he admitted honestly.
Madelaine smiled so hard her nose crinkled and she gave in. It would have been the end of her world if any neighbors saw the little performance and told her parents, or worse if they taped the sexual liaison and posted it, but at this point she was going to risk it. With a quick motion of her arms, she dropped the shorts halfway down her ass, exposing her red thong with white frills around the edge. However, in the next instance she had then pulled right back up.
"Damn," Connor groaned. "I know this is just a tease but you gotta show me more of your beautiful butt."
His begging and appealing to her vanity clearly was the way to win over the guilty-feeling actress. Madelaine smiled over her shoulder at him then slowly and seductively dropped the shorts, this time stopping only once her entire ass cheeks were shown.
Her ass truly one was to marvel at. Nice and round, her wide hips meant that it had great width while she was genetically blessed with thick muscles in the area. It was a top ass, very much so given the modern standard of any good booty needed to be big. She’d worked hard for this nice of an ass with countless hours in the gym, but clearly it had been worth it.
"I'm still a bit concerned with the neighbors seeing us. If they record us or even just told my dad he would kill you and ground me for life," Madelaine said, pulling them back up after a minute of drooling over her.
"No car in the driveway, we're fine," Connor motioned to the next door neighbor.
"Good point," she replied, feeling his hands on her chest.
"Show off your tits," he demanded. "Besides, even if someone recorded us the sex tape would be epic and probably launch your career bigger and faster."
"True," Madelaine smiled.
She didn't get the chance to take the wet shirt off her body before Connor reached in over the top of her tank top and flopped out her tits. They were a glorious C cup, large and meaty. The perfect companion to her big ass as it evened out her upper and lower body, plus gave men two things to stare at on her. It also gave her the classic hourglass figure that had her male audience creaming their pants when they watched her on TV, especially since Riverdale loved showing off her assets.
"Take your shorts off, I'll put them in the dryer," Connor offered, though his intentions were clear.
The taller man's hands didn't leave her recently exposed tits as his fingers continued to pull lightly on her nipples, making them erect in the hot sunlight. Madelaine was still able to let the short shorts slide off her great thighs and onto the ground, where they were picked up by the nice boy.
"Thanks," she said, folding them and placing them on the table top.
As she had bent over to put them on the table, a strong hand was placed on her back between her shoulder blades. She smiled and shook her head as she knew Connor was doing this so he could get another long look at her great ass with her bent at the waist.
"Shake it for me," Connor asked.
With them deeper into the privacy of the garage, Madelaine was feeling braver. First she chucked off her see through top then did as Connor wanted. Taking him through all her moves from the dance floor, Madelaine Petsch wiggled, bounced and made her booty clap for the horny man. She dropped it low to the floor before finally bringing it back up, an inch from his face. At some point she had taken off her thong too, which was met by a low cheer from her boyfriend.
"Like that," she smirked.
"Yeah," he admitted. "Fuck, you have me so turned on."
"I can see that," she said, observing his erection through his pants.
"And what about you," he said, stepping right in front of her.
His hand slid downward, starting at her pillowy breast which he knead for awhile. After tweaking the nipple like he was so fond of, he continued down over her flat stomach then where most girls had a triangle of curly hair that led to their sex. Though Madelaine found a complete bald pussy to look erotic, she found men preferred that she leave a thin, trimmed strip of her bright red hair just over top her pussy. Connor was one of those men, as it looked sexier knowing the carpets matched the drapes, plus it still allowed for his fingers went unimpeded to her pussy lips, already dripping in her arousal.
"Fuck," she tossed her head back and moaned as his finger entered her. After a minute of being fingered, Madelaine finally spoke again. "Let me taste."
As Connor withdrew and offered her his fingers, Connor stepped behind her once again. Madelaine didn't care, she was focused on getting the two digits that he used to penetrate her pussy into her mouth and suck her tasty cream off of. However, with his more coordinated right hand busy with Madelaine's mouth around the fingers, Connor used his clumsy left hand to reach back behind her to feel her sex once more.
"Oops," he said at the same time she blurted. "Whoa."
Connor's hand had accidently poked against Madelaine's backdoor. He didn't need to be reminded that it was something they hadn't done before, but the redhead took the chance to tell him anyway. He knew better than to just go right for the backdoor before even talking with the girl, but Connor was too horny so didn't want to admit it was a mistake.
"It's fine just relax," he told her, aiming lower and fingered her snatch.
An idea suddenly hit Madelaine and the more she thought about it the more she liked it. It was a way to stop her from feeling guilty about drunkenly cheating on Connor while at the same time not exposing her secret and breaking his heart. He got the opportunity to finally take her someplace he never has before, a pretty sweet offer on his part if she said so herself.
"Did you want to try," Madelaine asked him.
"Try...here," he asked, grazing her puckered asshole with his thumb.
"Yeah...I mean we haven't done it before so I thought..." she said before trailing off.
"I mean yeah I would love to!"
"Ok cool...so we'll try," Madelaine confirmed.
"But first..."
"But first you want me to suck your cock so good you get to cum in my little slutty mouth," Madelaine finished his sentence.
"Sounds perfect," he grinned wickedly.
Madelaine gave one last look around to make sure that no one was around and that the visual access to the garage was blocked. Satisfied enough, the redhead dropped down to her knees, a position she found herself in fairly regularly, and really enjoyed.
His cock was already straining against his pants so Madelaine had to be careful not to get smacked in the face when it was freed from his shorts. An impressive 9 inches, it was one of her favorite cocks she ever had between her lips. His smooth shaft was decorated with some small veins, while his cut manhood with exposed pink head looked so inviting to suck on.
With a wicked grin on her face, Madelaine licked her lips before guiding his cock towards her face before engulfing his bulbous head between her lips. The golden-haired man couldn't help but let an audible moan as her hot wet mouth worked the first half of his cock over. Connor was already close to popping his load in her mouth once she started inhaling his whole cock into her mouth with each stroke.
"Yes. Suck it babe," he moaned in delight towards the dirty actress.
"Mmmmm," Madelaine moaned as she noisily slobbered on his meat stick.
Sucking cock was something Madelaine really enjoyed. She didn't understand how some girls wouldn't do it, or would only do it reluctantly yet they would love when their man went down on them. Boys loved head and they would do anything for a girl that would willingly and happily do it, especially if they were as good at it as Madelaine was.
Madelaine parted her plush red lips and brushed her long hair behind her ears then took him into her mouth again. Just like before Connor moaned audibly as she started sucking him off while he was left with his head tilted back and fingertip digging in to the top of her head. She enjoyed the effect she had on him, but shifted all her focus on building momentum as she bobbed her head up and down his towering pole, taking more of him inside her each time. After a good minute of the more intense blowjob, she slowed her pace back down then pulled off his spit-covered cock altogether.
"God I missed this cock," Madelaine said as she licked his shaft. “Could suck it all day long.”
"And I’d let you, Madelaine," Connor agreed.
Madelaine wanted to give him a great blowjob for two reasons. One was that he was going to do her chores for her, which was a big bonus because she hated washing cars, mostly because either a machine or someone else could be paid to do it. And two was because she felt guilty for cheating on him, so by giving him a great sucking it would relieve some of that guilt.
The young actress pulled her mouth from his dick, now slick with her saliva and used her hand to feverishly beat his meat. She did this so that she could use her tongue to help corral his heavy sack to bring it into her mouth.
Madelaine took turns taking each nut into her mouth and giving it proper attention before she moved back to something more solid. She moved half of his pole between her lips while stroking the other half. Using her free hand to massage his sack again, she could hear how much he appreciated what she was doing.
With her lips back around his dick and no more words need to be spoken, Madelaine could concentrate on the task at hand. Connor couldn't help but look down and observe the slutty redhead in what looked to be her natural environment; on her knees with a cock in her mouth.
After taking half of him in her mouth to get them both back into a normal tone for the blowjob, she planted her lips completely around him and bobbed her head back towards the tip. Her mouth felt warm and wet to him, and the way her plump lips dragged along his slick skin made his resistance to pumping her full of cum right then and there wane.
"I'm not gonna last forever Madelaine," Connor warned after a few more minutes.
Madelaine knew exactly what that meant, having been hooking up with the boy for close to a year. If she wanted she could finish him in short order or she could pull off him and fuck him for awhile though he wouldn't last too long. However, the deal for washing the car was a blowjob so Madelaine set her sights on making him cum.
The red-haired actress increased her suction and bobbed her head back and forth. Her speed was a sight to behold while her hand stroked the second half of his cock not occupying her mouth. With mouth sucking and hand jerking him off, Madelaine felt his knees wobble some, while his hips hunched forward towards her skilled mouth. Taking these as telling signs, the horny girl worked harder and faster to finish him off and get out of such an exposed position where a neighbor could stumble upon them.
The girl was too good and Connor hadn't gotten any in a few days which meant he was never going to last that long when faced with her skilled technique. He reached his hand out to steady himself on Mr. Petsch's workbench as Madelaine got more intense by the passing second. Connor knew his girlfriend well and didn't have to vocally warn her about his imminent release. Unless in the shower he was to cum in her mouth and she would happily swallow the salty load, though when easy access to clean up he was able to cum on her tits or face, whatever he preferred.
"Cum for me baby," she pleaded, hand a blur on his cock.
"Uggghhhhh," Connor grunted as her slutty words pushed him over the breaking point.
Madelaine felt the first blast of his sticky load smack the back of her mouth shortly after his load groan. It didn't take him long to fill her mouth with his excessive amount of semen but the middle Petsch girl was equal to the task. She collected every drop he offered her until he finally ran dry. In one big gulp the horny redhead swallowed down his warm salty load, loving the feeling of the thick liquid as it slid down her throat.
Ever since she started giving guys blowjobs, Madelaine understood quickly that boys and now men liked cumming in a woman. Could be her mouth or pussy, didn't matter, they just didn't want to pull out. She quickly learned to get used to the taste of cum and now after a half a decade of gladly swallowing load after load, she loved it. The salty taste was common to her, and she got pleasure from the way men loved it and how their member would throb before spilling onto her tongue, then wiggle around in her mouth.
"Not to rush you at all, but those cars need cleaning and I want sex afterward so maybe hop to," Madelaine said, still on her knees with hand on his cock.
"Oh right," Connor agreed.
The man stepped back and pulled up his shorts passed his softening cock that was still tingling in the after-orgasm bliss. Finding the hose left in the soil beside the driveway, Connor ran the water over the entire vehicle, washing off the small section of suds Madelaine had lathered onto the door.
"What are you doing," Madelaine asked, still tasting his cum in her mouth.
"What do you mean? Rinsing the car like we agreed," Connor answered, soaking the vehicle in water.
"No I haven't soaped it first. My dad will know the difference and I'll be in more trouble," Madelaine argued. "You said..."
"Said I would rinse it for a blowjob. You did your job and I did mine. Washing the truck is a whole new deal, much bigger consequences," Connor stated.
"Really," Madelaine asked, her curiosity peaked. "Okay big boy. I hate washing the truck and will agree to anything. You do that, let me go hang out inside and then you can collect your reward."
"And my reward is," Connor asked.
"Whatever you feel you deserve," the redhead replied.
Connor was left to ponder her words, as after she told them she turned to go inside. Halfway towards the door she looked over her shoulder at him, wiggled her ass, gave him a sexy look then continued walking.
* * *
It wasn't the first car Connor had washed so he set about the task in a deliberate manner that was found to give good results in as quick a time as possible. Though Madelaine was waiting for him inside, ready to do whatever his disgusting, sexual mind could conjure up, he wasn't going to rush doing a poor job on Mr. Petsch's vehicle.
All and all, it took Connor just under 30 minutes to get the car shining in its brilliant bright green color in the Californian sunlight. The shirtless man took a minute to appreciate his good work while sipping some soda before remembering what was waiting back in the house, no more than 40 feet from him.
Connor entered the house through the garage and stepped into the kitchen, which dredged up many good memories. He ate and enjoyed many meals in this room in the last year, he had also had sex in the kitchen, bending Madelaine over the counter and fucking her from behind while the rest of the family was out.
"All done," Madelaine asked.
Connor had just entered the living room and found the red-haired young actress lying on the sofa. She had her laptop on her lap and the TV on, but her big eyes flashed to the tall man as he walked into her visual field. She hadn't bothered to change, though her bra-less tits were pushed back into her wet white tanktop, while her shapely legs were completely bare. In fact, the only clothing on her lower body was her red lacy thong that she knew Connor loved so much.
"Yup," he grinned.
"Ok."
Madelaine closed the computer and set it aside on the coffee table in front of her. Swinging her legs off the sofa, she got to her feet and walked over to Connor, who had made it halfway inside the room. She took his hand and led him towards the stairs, up the steps then entered the second room on the left.
Madelaine released his hand as they went through the threshold of the doorframe and climbed onto her good sized bed. Standing tall on her knees, the redhead turned around to face her boyfriend who had predictably followed her closely. Her arms immediately went around his neck as the couple kissed, slowly and tenderly at first before the passion started to ramp up.
The Riverdale actress felt the older man rub her back, traveling downward the entire time. When he reached the sexy curve of her low back his fingers closed around the hem of his tank and lifted it easily over her head and off her body. Connor broke the kiss and took a moment to close his lips around each of her nipples in turns, getting them hard with his sucking.
"Fuck," Madelaine swore, head tossed back and hands running through his long hair.
The actress only had her thong left on, but that proved no barrier for the horny man. Connor went back up to Madelaine's mouth, kissing her with his tongue pressing into her mouth with their bare chests pressing against each other. He loved the feel of her large tits with rock hard nipples pressing against the tight abdominals of his own physique.
However much he liked her boobs against him, Connor wanted to do more than just kiss the hot and bothered girl. Creating some space between them, the single-minded man slid a hand down between them and under the waistband of Madelaine's panties. Instantly his fingers were rubbing through her folds, collecting her ample amount of juices before penetrating two fingers deep into her sex.
"Wow...you are still so fucking wet," Connor observing, his fingers sliding in without friction.
"Well you teased me outside. Got me all hot with no follow through," Madelaine pouted.
"Bend over and let me see your ass," he told her.
"Do you like my ass," Madelaine asked, giving it a little wiggle.
"You know I do," Connor replied as he rubbed it's soft flesh.
"You can play with it," she told him.
Though Madelaine and Connor were no strangers to sex with each other, the one act they never did with one another was anal sex. Madelaine had a bad experience with a senior in high school when she was a sophomore, but had garnered the reputation of "anal girl" around the high school. For the rest of the year she was sodomized weekly by a different male student, as she was so vain as to not want to lose favor with the upperclassmen. However, it had soured her to the act and hadn't been taking it in the ass for three years.
"Whoa...mhmmmm," Madelaine squalled at first before moaning.
She wasn't sure what she was expecting but he had surprised her. After lightly swatting each of her pale cheeks, an action he was doing with more regularity as the time passed, he stationed himself directly behind Madelaine. Sucking on three fingers, he brought them forward then pushed them into her snatch in one stroke without warning.
Once she started to moan Connor went about fucking her with the three digits pressed tightly together. His girlfriend was a slut and loved sex, but she was still surprisingly tight for someone with her reputation. He supposed being petite and only 22 years old accounted for that. However after a minute of getting finger blasted, she was cumming around his digits in the fastest orgasm of her life.
"Fuck. That was quick, even for you," Connor complimented.
"Your fault, you're really good at that," she admitted. "But while I'm all relaxed from cumming, you should play with my ass."
Connor was impressed by her gung-ho attitude towards the act that most girls hated, including Madelaine herself until recently. Not wanting her to change her mind, the tall boy didn't hesitate and got ready by placing his hand towards his mouth.
Madelaine could hear him wet his thumb as he stuck it in his mouth to transfer as much spit onto the digit as he could. She couldn't help but jump a little bit when she felt his palm contact the top of her ass, but she condemned herself for the irrational action.
Connor was surprised by her start so he waited for a few moments until her muscles melted into her more normal, relaxed tone. With her back to calm, Connor slowly lowering his thumb downward, stopping when it was pressed against her tightly clamped butthole to rub her starfish and transfer the surface spit.
"Just be gentle," she pleaded softly.
Nodding his head to answer her, Connor started to apply pressure. He could tell that she was still slightly tense, but his own experiences were telling him it was still loose enough to continue. He was correct, and after applying a little more pressure he watched as her hole gradually expanded until finally the first part of his thumb disappeared inside her backdoor altogether.
"Ugghhh...awww," Madelaine moaned as his thumb slowly was worked into her backdoor.
For the next few minutes no words were exchanged between the couple as Connor focused on his task. He made small thrusts into her anus, getting more and more of his digit into her booty until it was completely inside. Madelaine reacted well so after that he made long yet slow strokes with his entire thumb over and over again. To both their delight, and Madelaine's amazement, she was getting very positive groans as a result of his methodical fingerblasting her asshole.
"Mmm...yeah I like it," she admitted honestly with lust in her eyes as she looked back at him.
"How much do you like it," he asked, burying his digit all the way into her asshole.
"A lot...ahhh," she groaned.
Connor didn't want the act to get stale and he also wanted to keep making positive strides. It pained him to do so, but he pulled his thumb slowly and smoothly from her rear, watching as the starfish paused in that state before sealing back up tight. His middle and index finger were coated in copious amounts of Madelaine's cum from earlier so his first finger had no problem making its way past her muscular ring in order to call her asshole home.
"Mhmm," Madelaine moaned, penetrated by a slimmer digit then before.
Connor allowed the juices to spread along the depth of her backdoor before he pulled back so only the fingertip remained in her booty. Pressing his longer middle finger alongside the first, the long-haired boy pushed forward. It was more of a struggle this time with the added thickness, but his determination won out and now he was fingering the Riverdale stars asshole with two fingers.
"I think I'm turning you into my own personal butt slut," Connor grinned at her after she started moaning from his attention.
"I think you might be right," Madelaine smiled back.
"Now you do it," Connor said.
He didn't know if Madelaine would do it or not but he figured she would given how sexually liberated she was. As he expected, she brought a finger into her mouth to prepare it with saliva then reached back behind herself, overtop her thick ass then nestled her hand in the deep canyon of her cheeks.
"I've never done this part before," Madelaine admitted as her finger rubbed her starfish.
She seemed nervous about it but Madelaine never met a sexual situation that she wouldn't try. With her wet finger already in position, the redhead pressed her middle finger against the center of her backdoor. It was surprising to her how quickly she relaxed and let her own finger inside her asshole, penetrating herself.
"Oh shit," Madelaine screamed, knuckle deep in her booty.
She rested the finger in her backdoor for a moment then was curious. So far it didn't hurt, but that wasn't surprising given how Connor's thicker finger had already been inside. However as she moved her finger in and out, only working two inches of a thin finger, but regardless it felt pleasing. It didn't hurt and the tightness and frequent squeezing of her muscular ring was interesting.
"Congratulations Madelaine Petsch, you just fingered your asshole for the very first time," Connor said in a game show host voice.
"Haha, shut up Connor," she laughed. "Can I be honest? I'm really curious how I taste, you know, back there."
"Try it."
"Really? You don't think I'll be gross," she asked, wrinkling her nose.
"You love how your pussy tastes so may as well sample the other hole too."
Truth be told Madelaine was going to do it regardless but it was nice having her man's support. Pulling out of her anus, Madelaine brought her arm back around to a normal position before sticking her middle finger apart from the rest. Her eyes flashed over to Connor and saw him watching her with intent so she smiled and put the digit in her mouth.
"Gotta admit, I really do taste great," Madelaine said before going in and sucking her finger again.
"You really do," he said with a shit-eating grin.
"Now why don't you help me out again," Madelaine said, wiggling her ass to emphasize her point.
"Actually I think you should help me out," Connor said, eyes flashing down to his erection.
"Help you," Madelaine asked, already turning around. "Get up here,"
Connor was kneeling on the bed across from her in no time, but before his hands could start undoing his shirts, Madelaine's hands were there. She gave him a tongue filled kiss as he felt her undo the belt first, before more pressure was relieved from around his waist as his button was undone.
The redhead had made short work of his last remaining clothes and was stroking the cock she had sucked off 30 minutes prior to life. It felt smoother than before, likely the result of her saliva bathing him and making him slick, but it glided with ease in her hand, getting harder. It reached its full height and thickness when she dropped down low onto knees and elbows and took his swelling head in her mouth.
Looking down, Connor observed as Madelaine stroked his long shaft a few times before parting her lips and engulfing the first several inches inside her warm orifice. The fire-haired actress wasted no time with pleasantries as she immediately got down to business. After taking a few long sucks at only the tip of his cock, using her tongue to lick his sensitive pee slit, Madelaine pushed over half of his length into her mouth until his head was pressed against the back of her throat.
"Ugghhh," Connor grunted his approval. "So talented with your mouth."
"And that's not all," Madelaine said with a wink.
That would wait for now as Madelaine went about getting him good and hard for more fun to come. She figured she wouldn't be blowing him for long, not that she would have minded of course. But given the promises of anal sex and how hard Connor negotiated for it, she knew he'd want to get to business sooner rather than later.
Madelaine held back a smile when Connor groaned again when the redhead pushed her head down lower and took more of his cock into her mouth. She could imagine his mouth agape and eyes rolling into the back of his skull as he marveled at the ability she possessed to please with her mouth.
However much she enjoyed the feel of his hard cock in her hand while he throbbed between her lips, what Madelaine wanted more right now was his prick in a different orifice. Which was why the next words that left his mouth filled her with happiness.
"Need to be inside you," Connor practically demanded.
Madelaine wasn't going to argue at that request and allowed the boy to grab her around her narrow hips and flip her over onto her back. Her face was now pointing skyward but still close to his body, so he leaned over her head and large tits, his cock dangling against the smooth skin of her breasts and flipped her around.
"Whoa," Madelaine squalled, excited to be manhandled by the much larger male.
With her in position, Connor waited no longer to get inside her. Clutching his cock around the base, the long-haired boy kneeled closer and plunged half his length into her snatch before stopping his momentum. Madelaine moaned like a whore as he penetrated her sex, but then felt a longing to have him back when he pulled out nearly all the way.
"Damn," Connor swore, plowing back into her.
"Mhmm...awwhh...much better," Madelaine groaned.
This time when Connor stroked back inside her wetness he went all the way, much to her happiness. By the next time the lucky man repeated the action, her tits bounced up towards her face given the force he used. She loved it and begged for more, so the next time Connor plunged into her depths her boobs nearly smacked her in the face.
"Fffuuuccckkk," Madelaine dragged out the curse word.
Madelaine was in pure bliss at the moment as Connor used her body as he wished. It was exactly what she was longing for, to be used by him, filled by him. Sure, any cock could be doing what his was doing, pistoning into her wet pussy like a machine, but it was the way he did it. The twist of his hips when he speared inside, the upward grind when buried deep to stimulate her clit and the rest of it. She hated that she cheated on him but was hoping to make it up to him now.
"God you feel so good," Connor barked.
Madelaine's smile and reply was stifled when the lanky man leaned down and kissed her the next time he thrust deep into her. He pressed his muscular chest against her pillowy tits, stopping them from bouncing and allowing her pink circles to dig against his slightly sweaty skin. His tongue filled her mouth and she moaned against it while his prick wiggled and poked inside her.
"How about I turn around and get on it," Madelaine offered. "Give you a view of what you bought."
"Best idea I've heard all week,“ the blonde man commented.
Madelaine wasn't happy to her a common expression her dad used as it forced her to picture the much older man, but the sight of Connor's glistening cock, slick in her juices, broke her of that. She ran a hand over his rippled abs as he pulled out of her warm snatch before moving to allow him his turn to lay on his back on the bed.
"Now lay back and let Madelaine do all the work sweetie," she told her boyfriend.
Connor could have no complaints with that sexy comment, nor could he with the view he got as he watched his curvy girlfriend crawl to the level of his groin. Her shapely leg went over his waist before she sat back, not needing her hand to help as his tip poked around her lower lips before finding its mark.
"I love how good you feel," Connor groaned as his tool was engulfed in her moist heat.
Madelaine flipped her long, shiny hair out of her face and descended all the way down his lengthy cock. She had her fair share of men the last few years but Connor's cock was up there amongst her favorite. It was long enough to reach all her sensitive places while thick enough to fill her twat nicely.
With her sitting on his lap, Madelaine grinded back and forth to rub him deep in her pussy, hitting every zone possible. It also allowed Connor the chance to have a breather after the energetic fucking he was performing on her minutes ago.
However, with him that deep inside her, Madelaine decided to give him a good show by raising a few inches up before snapping back down. The result was her thick ass crashing down to his lap while smacking against each other. It made an audible clapping noise as her luscious ass cheeks shock in a maneuver that made her boy stiffen harder.
"I knew you'd like that," Madelaine said, looking back over her shoulder as his hands palmed her ass.
Up and down Madelaine rode on his cock, all while Connor's eyes stayed transfixed on her ass. Every since they started dating he had wondered about what it would feel like to travel her dirt road, and how it would compare to all of his other previous anal conquests. He was definitely a fan of sodomy and up until Madelaine, he only dated women who let him put it up their asses frequently, but never had he done the deed with Madelaine.
Knowing that today he had a free pass to do whatever he liked, he was going to take advantage and finally make his move. Finding his courage, he grabbed Madelaine's shapely hips and pulled them down towards his sex. She got the point after a few more bucks up his shaft and finally settled in his lap with his cock buried deep in her pussy.
Instinctively Madelaine began grinding her hips in place, making him feel her velvety cunt around the lower parts of his dick. However, it was his action which was the more bold and surprising.
"Whoa," Madelaine shrieked before calming herself.
His finger, wet in saliva after seconds of sucking on it, was placed against her backdoor. Much like he had done earlier, Connor pressed it forward, gently yet firmly until her sphincter relented again. Unlike last time though, the redhead already had a big cock filling one of her holes, and even now she could feel his padded fingertip touching his tool threw the thin membrane separating them.
"Keep riding, nice and slow," he told her.
Madelaine did as she was commanded after a second. Connor didn't try to push his finger in any deeper, instead he held it firmly in her ass up to the second knuckle and allowed her to ascend his cock once more. By the time she crashed back down and started to raise up again, she stopped thinking of the digit in her dumper and was focused back on how good it felt to fuck her boyfriend.
Connor watched on as his beautiful girlfriend became more comfortable with a finger in her ass. After another minute she was back to her original speed of bouncing on his cock, taking him deep in her snatch all while his fist clattered against her rounded cheeks.
"I think...I like it," Madelaine admitted.
Connor was going to tell her of his intention to double the amount in her bum but the way she was adjusted told him she'd be fine. With his free hand he had her slow down her reverse thrusts until stopping her completely.
Madelaine wiggled her ass, thinking she knew what was to happen. She was proven correct when a second finger pad was felt probing her starfish before pushing into her backdoor. This time she didn't skirt away or grunt in discomfort as the finger went in to join its neighbor without much difficulty.
"And here I thought you didn't like any butt play," Connor asked, observing as she rocked her great booty back on his fingers and cock.
"What can I say, you bring it out in me," she replied with a sultry look over her shoulder.
"So, second thoughts at all," Connor asked, not too worried for the reply.
"No. I wanna try," Madelaine said firmly. "You just have to warm me up a little more. Your cock is bigger than a finger or two."
"Go on your hands and knees," he instructed.
Madelaine was being 100% compliant and did as the tall man asked her. When she was in position she saw him go to her nightstand and grab a bottle of lotion. Expensive hand lotion but if it kept her asshole from screaming in pain as it was penetrated then it would be worth it.
Connor placed a big dollop of the pale cream on his digits when did likewise to the very center of his girlfriend's backdoor. Madelaine wiggled as the cool cream touched her most taboo of places but a steadying hand from Connor stopped her. Next she felt his soft padded fingers rubbing her crinkled ring...then discomfort.
"Ugghh," Madelaine moaned as she pitched forward.
Though she was fine taking him minutes before, the difference then was the fact that a big cock was pleasuring her twat. This time, the couple was overconfident and Madelaine had learnt the lesson that when it came to taking anything up her ass, caution was the name of the game until she was more comfortable with the act.
Connor had attempted to put two thick fingers into her asshole and things didn't go great. Her sphincter relaxed and allowed him entry, however then shock of the penetration was too much for Madelaine, but he wasn't going to give up.
"Relax," he told her. "Rest down."
Madelaine did as she was asked again, lowering herself so her face and large tits were on her soft bed. Her ass remained up in the air right in front of Connor, which was the worrying part since he had a determined look on his face.
This time before she felt his fingers she felt something softer, wetter. His tongue. Connor was tossing her salad, licking her starfish, eating her asshole...and it felt nice. Good even. He did it for a few minutes, his oral sex always was great and lengthy then he slipped in a finger. It was gentle but was completely embedded in her ass and she barely registered it.
"Mmm," she found herself moaning.
This time, when he added a second, she didn't buck to get him away or grunt in pain. Instead it was a seamless transition with the briefest flickering of discomfort that soon vanished. For the next little while, the long-haired man fingered the asshole of the beautiful actress all while she moaned.
"So," he asked, withdrawing after a while.
"That felt...good," she surprised herself by saying.
"Rub your clit," he told her.
Madelaine didn't waiver as her hand shot down, quick as a snake, to flick her sensitive bean. No sooner had it happened when Connor pressed a third finger tightly against the others and pushed forward. The redhead felt her hole stretch then allow him access while any pain was pushed aside by the waves of pleasure.
"How many is that," she moaned.
"Enough," Connor answered coolly.
Madelaine felt the bed creak and shift underneath her as her large boyfriend moved around. She didn't have to look back to know that Connor was moving directly behind her, which was true. His hard dick was in his free hand while his other was stop blasting his three fingers into her asshole.
Calmly, Connor placed his cock right up against the digits in her ass then withdrew them from her anus slowly, as to not cause her pain. Once clear of her hole he acted quickly to take advantage of the gap that remained as he nestled his purple head against the hole then moved his hips forward smoothly.
"Ho...ly...God you're in my ass," Madelaine screamed in a fairly low tone.
His thick cock had finally broke through the tightness of her sphincter and now his tip was penetrating the hole that hadn't been fucked in years. As if her words weren't enough of a tip-off, Connor could feel her clench up with every fiber of her being, preventing him from moving within her though he had no intention yet.
Connor was a patient man and adored the young actress so was in no rush. He waited with his tool placed an inch within her bowels for Madelaine to grow relaxed, however this took nearly a minute. Just like he knew she would, her breathing started to return to normal and he observed the tight cords of the muscles running alongside her spine lose their tone.
"Keeping touching yourself," Connor reminded.
Madelaine had forgotten all about that aspect, actually she had forgotten about everything the second his huge cock entered her rectum. The initial penetration wasn't very painful given the thorough work Connor had done to loosen her up, however the fear and uncertainty of being sodomized again had overcome her.
Now hearing Connor's calming voice and relaxed presence behind her, she returned to her original mindset of being determined to try anal sex again. The fact Connor wasn't pushing the issue and attempting to blast through her defences really helped but her mind at ease.
"Mhmm," Madelaine moaned as she found her clit.
Connor also took her moan as a warning that she was ready for more. The beautiful girl touching her most pleasurable spot seemed to melt her hardness, more specifically he felt the iron grip of her asshole relent from squeezing the hell out of his member. He took advantage by slowly pushing the next inch of his cock into her backdoor, then stopped.
"Still good," Connor asked, slowly retreating to his initial depth.
He wasn't going to push her too far too soon but he wasn't going to stop and stand still. Taking it easy, Connor worked the very tip of his cock into her ass one inch at a time. The approach was working and soon he found that nearly half his considerable length was buried in her bountiful booty, however any time he tried progressing further his attempt was blocked by her clenching down.
Connor figured she may need more than just kind words so he bent at the waist without thrusting more of his member inside her ass. He placed his lips against her left shoulder blade and kissed the skin, sensing a tingle rip through her body.
Madelaine moaned in response to his intimate touch then remembered to keep rubbing her clit. The combination was key as when Connor brought his hips slowly forward he made half an inch more progress before reversing course.
"Awhh...ohh," Madelaine grunted, more from pleasure then aggravation as he continued pushing more meat into her booty.
She tightened up a few more times but Connor had the recipe for that down pat now. He would pause and start kissing her back, hitting her spine, shoulders or neck, it didn't matter. When she was relaxed again, Madelaine would initiate and push backwards towards him, which made him so hot knowing she was essentially fucking her own ass using his cock.
"That's it, doing so good," he complimented the sodomized girl.
"Not sure...how much more...I can take," Madelaine said through grinding teeth.
Connor couldn't help but laugh. "Really? Because that's all I have to offer."
Madelaine couldn't believe her ears, that she had successfully taken all nine inches of Connor's thick veiny cock in her tight little ass. But when he swiveled his hips she felt him against her, his wiry pubic hairs tickling her plump ass cheeks.
"Holy crap," Madelaine gushed in pride. "I'm one bad ass anal chick now!"
Connor smiled but was more interested in fucking his beautiful curvy girlfriend in the ass rather then be proud of her just yet. Pulling half of his length from her rectum, Connor stopped then pushed all the way in, stopping only when his groin smacked her cheeks with just enough force to cause them to ripple.
"Easy cowboy," Madelaine warned as her hand sprang backwards and was placed on his stomach in order for him to take it easier.
"Should I stop," he asked, concerned he went too fast too soon.
"God no," she swore. "Just a bit slowly stud."
This time when Connor took greater care to slide in and out of her lubricated asshole, Madelaine couldn't believe the feelings she was experiencing. For a girl who had as much sex as she did by 22 years of age, she was shocked to find a new act that could feel so good. It wasn't as pleasant as regular sex, but when she rubbed herself strong enough and he hit into her a certain way, it actually was more intense.
By now Connor was stroking his whole length into her backside and the pain was all but gone. If he went to suddenly forward or was too jerky withdrawing then there would be a flash of discomfort, but by and large it was feeling good, damn good actually.
The feeling of a cock in her ass, fucking her with his whole meaty shaft was hard to describe. She felt so completely full and that gave her an oddly pleasurable experience, while her fingers which continued to friction her clit added an extra layer of bliss.
"Tell me if you like it," Connor told her, growing confident.
"So much. I like it so much," Madelaine moaned for him.
She was enjoying herself so Connor decided to push his luck by using more power. It was a slow increase but he was using more force to thrust into her all the same. He only used half his length until he was sure she was able to handle it, then steadily used more of his shaft until his pole from bulbous head to his thick base was sliding into her backdoor.
"Fuck me," Madelaine swore, head swinging between her arms. "Fuck my ass."
Connor grinned like a demon when she begged for him to continue sodomizing her, but the smug look was whipped from his face when her anal hole winked around his shaft. Going tit for tat, Connor decided to stimulate another sensual zone on his lovely girl by using a hand to reach around her back and find the nipple of one swinging breasts.
She lowered her face to the mattress and bit into the sheets, stifling a moan in the process. Connor was now fucking her ass, tweaking her sensitive nipple all while she rubbed her own clit. All in all, much to her utter shock, Madelaine was getting pushed closer and closer to a second orgasm of the night, one that would easily surpass her first in magnitude of intensity.
Meanwhile while Madelaine felt her orgasm building up within her wet core, Connor was moving closer to one of his own. Working his entire cock into such a tight ass was taking an unbelievable toll on his resistance even though he had cum in her mouth in the family garage less than an hour ago.
"Hot darn that's a tight ass," Connor groaned in his typical corniness.
"Oh shit...oh shit...I think I'm gonna cum," Madelaine shocked herself by screaming.
Though it had been coming for a little while, her pending orgasm was still shocking for Madelaine to experience. Given how painful her failed attempt last time at anal sex was, she was hoping that this time wouldn't hurt much. Never in her wildest dream did she expect her bumbling boyfriend to ass fuck her to cumming.
With a loud shriek of utter delight, Madelaine creamed all over her wildly rubbing fingers. It caused her whole body to stiffen, then start to twitch and she was only vaguely aware of Connor slowing his thrusts to a crawl until she was completely spent, orgasmic bliss washing over every nerve fiber of her body.
"Nngghhhh," Connor groaned.
His goal was to ride out her orgasm with only the slightest stroking into her then take advantage of the relaxation of her afterwards. Though it almost drained him completely, Connor withheld and was rewarded with feeling her asshole loosen up significantly.
"Here it comes," Connor said, more to himself.
This time when the long-haired boy thrust into her, he did so with a new power, cranking the thrusting force up significantly. He pulled his hand away from pulling her nipple and used both to grip tightly onto her curvy hips and hold her still. Over and over he reared back his hips, only to bring his cock deep into her ass with a new savagery.
"Ohh shit," Madelaine swore with his new approach.
His new thrusts were harder then ever before but not painful so Madelaine didn't complain. She knew there was no way for her to cum again so she figured she would let him use her body however he wanted to get his own climax.
"Cum for me baby," she encouraged her savage man.
Connor wasn't going to last much longer but he certainly was going to go for as long as he could. He thought things had gone extremely well for their maiden voyage into anal sex as a couple but still, the deed was not the most comfortable for the girl all the time so Connor didn't know the next time he'd be fucking her ass.
However, her great tush was proving too much for him. He pushed in a few more times, taking only a second to do so, then felt his balls start to tighten up. One last deep thrust, Connor appreciated the feel of her curvy bottom against his thick patch of hair before pulling out.
"Fuccckkkk," the normally dopey boy roared.
Madelaine felt and saw him move like a blur through mostly shut eyes. She found herself on her back, the comfortable mattress sunk in underneath her, with the hulking figure of her boyfriend straddling her tapered waist. He barely stroked his cock once before the tip erupted, cum firing out. It took 10 seconds but in that short amount of time her large boobs were covered in his plentiful load, streaks and droplets coating both pillowy twins.
There was silence for a few minutes, in which time Connor had tilted over to lay on his back beside Madelaine. They both drank in deep breathes as they recovered their energies and their wits, though even combined that wasn't much.
"Totally worth not having to wash the cars?" Connor finally asked.
"Oh you better believe it," Madelaine smiled as she spoke. "Shit! They’re gonna be home soon. You gotta go!"
"Alright sweetie."
- 1
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Madelaine Petsch Tries Anal Sex