Applejack's Odyssey

Rarity

Rarity heard he needed money so took advantage to have the “biggest cock within arms reach darling.” He'd accepted but was struggling to fuck her the way she wanted.

He'd begun by throwing her on her bed, ripping her pretty dress off (to shreds even), and tying her up. Then the rough part started.

He looked up at the list she'd left for him to do and sighed, dropping into his acting mindset. She was so small he picked her up to a sitting position by the throat, his other hand slapped her smallish tits and punched her nipples when she jumped away from his hand.

She was crying and Mac was about to stop when he saw the look AJ gave when she was loving whatever he was doing so he persevered.

He was already naked as per Rarities request, so his hard cock was free and hard after seeing one of AJs hottest friends nude for the first time, he looked up and followed the next instruction.

He pinched her nipple and as she gasped in pain he shoved the first few inches into her open mouth and plugged her nose to force her to keep it open, pushing further and further until his pelvis met her soft, plump lips and held it there.

Rarity was a small girl and dainty, she couldn't fight him off if she tried so her flailing as she ran out of air was nothing to him, Mac waited until she started to slow down to pull out enough for her to breath before fucking her face like a fleshlight, making sure to grab handfuls of the softest hair he'd ever felt messing up her well maintained hair style.

Mac was shocked that even with all of his reservations he was actually about to cum and tried so hard to pull out in time, he was too used to AJs love of swallowing and shit one rope into Rarity’s mouth before pulling out and painting her face with a few ropes before aiming the last shots and dribbles onto her purple hair. Rarity convulsed and shuddered as he watched and knew it was time for the last part of her list.

He picked her up by her waist and slammed her face down on the bed, spitting on her tiny asshole and beginning to push into the prissy girl. He looked down and had to admit that splitting the ass that has been teasing and taunting him for years was nice, even if he was being tasked with “destroying” it as she’d put it.

He noticed she'd slipped a ball gag in at some point after he'd cum on her, but didn't mind. It was hard enough to bring himself to abuse a woman like this and one so pretty as her.

He took a deep breath, put his hands on her narrow waist, and rammed the last inches into her. Rarity straightened and screamed into the ball gag, from pain or pleasure Mac couldn't tell but he pushed on. Her ass was tight and gripped him well, but he could tell that just as AJ said when she was mad that Rarity had excessive mileage on her holes already.

Rarity tried to wriggle away to safety but Mac smacked her ass hard each time and she submitted either cumming or getting close on each slap.

Mac's second orgasm was boiling inside him and he tried to think clearly while balls deep in the posh teen’s ass, and said screw it. He held on tighter, digging fingers into her so hard he was sure she'd have bruises and fucked her harder somehow, before hilting inside her and blasting his cum into his first crush (that wasn't his sister at least).

Rarity shuddered harder and began to jerk around while grunting before fully passing out. Mac let his normal self take back over and he placed her gently on her bed, tucked her in, and left her some pain meds and water on the nightstand.

Rainbow Dash

“Come on Mac, that's all you got?” Rainbow ran another lap around him. She'd challenged him to stamina and sports competitions and if he'd won she'd give him the money, if he lost then he did whatever she wanted for a weekend.

He has agreed and shown up to the school field and gym, and of course the cocky girl was wearing practically nothing to distract him.

He liked Rainbow but he never knew had AJ put up with her all the time, and something he'd never told AJ because she'd kill Rainbow is how often the sporty girl teased him in outfits just like she was wearing now.

She was wearing spandex running bottoms very clearly tailored by Rarity to show off even more on the fit girl, from some angles Mac could swear her could see her pussy lips around the edge of the fabric. Her top was a normal sports bra but even with her A-cups she had cleavage and she loved to show it.

Mac was very muscular and he tried to run when he could but the sporty girl was running literal laps around him, but he pushed on to finish and get to the other events she had planned. When he crossed the finish line the last time she was stretching and grinning “You almost caught me on the third lap” Mac grinned and tried stretching as well, but winced in pain from his legs.

“Whats tha next one?” he said looking down, Rainbow moved forward and moved his face up until he was looking at hers “Well I can obviously beat you out here, wanna join me inside for the real fun?”

Mac walked in to the facility and saw what little clothes Rainbow had on the floor leading to the boys locker room. He couldn't help it and cleaned up the clothing as he went to the showers.

When he got in the showers were running hot and after folding the clothes and putting them on a bench he saw the girl he was looking for.

Rainbow’s body somehow looked even more statuesque while nude, very firm but not too big ass, narrow waist perfectly sculpted, tiny breasts topped with very hard nipples, smooth muscular legs, and a bald tight looking pussy. Rainbow giggled “gonna stare at me all day or are you gonna join me?”

Rainbow watched and played with her nipple as she saw the man she'd wanted for years, she knew what Mac’s body looked like after so many “accidental” run-ins in the bathroom or late night spying. The only thing she'd never gotten a look at was the tool between his legs, based on the few times she'd teased him she knew it was big but this….

Mac was rock hard by the time he stripped and joined her in the shower letting his cock press against Rainbows belly as they grew close and as he kissed her she shivered from the contact. “Heh, yer pretty cute when you're like this.” Rainbow tired to push away, but Mac was turned on enough to need to fuck the girl rough.

So he gripped her waist and hip, making Rainbow squeak, and turned her around slamming her into the shower wall. Kissing and biting at her neck while his cock went between her muscular ass cheeks.

Mac slapped her ass making her jump and use that hand to guide his cock to her soaking pussy. He was able to slam his entire cock into the petite, fit girl in one go “Yah really needed this huh?” As his hands went to her hip and one grabbed her hair, entwining the rainbow locks in his hand he began to fuck her.

Rainbow's mind went blank and she had to focus on staying standing as her pussy was assaulted by her best friend's brother like she'd wanted ever since her crush began. She could only squeal and pant as her insides were battered by the much bigger man.

Mac kept fucking the sporty girl as hard and fast as he could, slowing down and speeding up as he tired and recovered, for 10 minutes.

By the time he pulled out and came hard shooting rope after rope of thick goopy cum onto the girls face and chest, Rainbow was catatonic and unmoving, but the grin of a satisfied slut was on her face.

Sunset

“Thank you for coming Mac, I know I'm paying you for this but I really appreciate it” Mac barely heard what she said if he was honest. Sunset answered the door in one of the tiny robes that Rarity had made her friends, and much like AJs hers hugged her curves perfectly and showed hints of what's underneath.

Sunset giggled as his eyes roamed over her body “glad you like it, I dressed to impress. And don't worry big boy, you'll get to see so much more. Now come on in while I get everything ready, you'll follow my lead on this I hope”

“Eeyup” and a nod were all the confirmation she needed to walk him to a chair in her apartment and told him to wait there, giving him her phone.

After a few minutes he heard a lilting voice say “Ohhhh Maccy, please start recording” Mac did as he was asked, and just as he pressed the button Sunset came around the corner and struck a pose.

Mac's mouth dropped open as his eyes drank in one of AJ’s hottest friends wearing a lacy, fancy set of lingerie.

Her long, shapely legs encased in thigh high white stockings that accentuated her well toned thighs, the lace garter and panties hugged her flush hips and when she did a spin for the camera her sexy back leading down to her full ass, the underwear barely holding the cheeks from jiggling, as she stopped her almost AJ sized breasts were held firm in by the lacy, yet covering, bra.

Sunset swayed her hips and danced a bit, showing off her body in an erotic dance that put pornos to shame before winking at the camera and swaying her hips while sauntering towards Mac in the chair.

She practically bounced with glee when she squatted between Mac's legs, hands running up and down his thigh until his cock was clearly shown through the fabric.

Sunset cooed and her eyes went wide “you've got such a big one for me sir” her finger traced his cock “let's get this tasty thing out and see what I'm working with” Mac lifted his ass up as Sunset masterfully undid his belt, button, and zipper in one smooth motion and yanked the pants down. Mac's cock flopped heavily onto his belly, and Sunsets mouth visibly watered as she took in her new toy.

“Wow babe look at this thing!” She said excitedly as her soft hand held his cock upwards, examining it like a scientist. “Oh sorry Mac, I'll stop teasing you. Plus I know a certain someone wants to see me play with a big toy like this”

With that Sunset’s flush lips kissed the tip of Mac's cock, she kissed her way down his shaft until she got to his balls making sure to suck on each, then glided back up his cock with her tongue until she engulfed his cock into her mouth drawing a moan from Mac which made her grin and wink at the camera.

Sunset's Cyan eyes looked into the camera, not Mac's eyes he noticed, as she took as much cock as she could each bob but never even got half.

Her mouth clearly strained but she soldiered on and kept sucking on the cock in front of her, bringing a hand with her mouth to jerk while she sucked. Her other hand was clearly playing with her pussy from the morning she was doing.

After a few minutes of sucking Sunset popped her mouth off his cock and stood up, showing off her bare dripping pussy to the camera as she turned around “I know you love this angle babe.”

As Sunset lowered herself onto his cock Mac was engrossed in her narrow waist, plump ass, and the pussy that only rivaled AJ’s in terms of looks.

Sunset was wet enough that with a little wiggling as she impaled herself that she took him in fully in a few seconds causing both to groan as Mac felt the warm, tight pussy squeeze every inch of his cock and Sunset from being fuller than she'd ever been in human form.

She turned back to the camera with a sultry look, a blown kiss and she put her hands on his knees, circling her hips and making sure his cock stayed buried in her while she did so. Then began to bounce on his lap, the wet squelch of her pussy yielding to his cock almost rivaling the sound of her ass slapping into his hips.

Mac tried his best to hold the camera still through the sexy girls attack on his cock while also trying to hold on and not cum too soon. Sunset was making it so difficult though, the girl clearly did this before, she knew every trick and move to make men enslaved to her.

He now understood why Snips and Snails were so obedient to her even after she stopped harassing his sis.

Sunset could feel his cock growing harder and swelling and knew he was about to cum so she did her meanest trick “selfie mode please Mac” Mac was confused but did as he was told.

She leaned back and mashed her soft teen body into his rough, mans body grinding hard and fast while kissing him hard. This was all too much for him, he held the phone at a good angle as best he could while he thrust into her.

His hand went to her waist eliciting an “Eep” from her, holding Sunset down on his cock while he came hard inside the slutty teen. When he was done Sunset fixed the camera back to normal and climbed down to suck his cock clean from her juices and collect some cum in her mouth letting the camera see it running from her tongue before she stood up, showing the trail of goopy cum dripping hard from her abused folds.

Blowing a kiss she stopped the recording she thanked Mac, giving him a towel, “Rest up Mac, I appreciate it a lot as does Twilight, she LOVES seeing me fucking men like you”