It was lovely evening with the moon and stars out in the sky. Looked like the perfect night for a date, like the one Vice Principal had this evening. Right now however, she was laying on her bed in her robe talking to her sister Celestia over the phone about a plan over attempting to adopt Sunset Shimmer. Luna hung up her cell phone, wishing her sister the best in her plans for Sunset.
“But enough of that tonight.” Luna said to herself as she got out of bed. “Gotta get ready for Cherry.” Tonight was gonna be Luna’s fifth date with her girlfriend Cherry Jubilee. Luna loved Cherry’s enthusiasm and lack of a better term Southern charm and Cherry enjoyed Luna’s more mellow tone and sarcastic quirks. Also the two had hidden love of old school video games.
Luna stretched bit and went over to her dresser, she pulled open her underwear drawer and took out a box and taking from it a skimpy bra and thong with grin.
With Luna, if a relationship lasted up to five dates she’d make an effort to convince her other half to take the plunge, by looking as desirable as possible.
She went up to her mirror, removing her robe and leaving herself naked until she slipped on her undergarments.
She gazed at her reflection, while the bra and thong were small they did cover the bare essentials. Luna grabbed her breasts to make sure they didn’t pop out of the bra. While not as big as her sister's’ pair she found her breasts well-sized, but they weren’t as important to the other side in Luna’s eyes.
She turned around and bent over a little to see the main attraction: Her rather big ass. When she was younger she was ashamed of how big it was. However during her college years when she, Celestia, and friends started to go naked at their secret spot she started to feel good over her’s being bigger than the others, and more she took pride in it the better she felt. Also plenty of guys and gals have liked a girl with more junk in her trunk.
She gave her cheeks a good firm squeeze. “Yup, still got it.” She then her ass a good smack.
“AAAAAKKKKK!!!!!”
Luna’s eyes widen and turned to see a seagull on her bedpost.
“What the? Where did you-” Luna then looked over and remembered she left her window open. “Right.” She turned her attention towards the seagull. “Get out of here ya vermin!”
“AAAAAAKKKKKK!!!!”
“I said get out! You’re not getting any food!”
“AAAAAAAAKKKKKKKK!!!!!”
“I. Said. GET OUT!!!” Luna rushed at the seagull causing it to fly with Luna chasing it around her room until it flew the window.
Luna reached out through the window shaking her fist. “That’s right! I don’t wanna see you agaaaaaaaa!!!”
Luna slipped off the edge and fell out of her window kicking and screaming until she landed in her bushes.
“OW!!” Luna cried as rose up in pain. “Freaking bird!” Luna’s face grew red knowing she outside in her underwear. “Crap! And both my doors are locked.” She looked up. “Gotta try the window”
Luna started climbing up the side of her house doing all she could to keep her grasp on the wall, she managed to reach the window but when she reached out to it her hand pressed against glass.
“What?!” She pulled her head up and to her dread saw the window shut. “No!” To make matters worse she lost her grip and fell again.
This time she landed on her back in grass, however the impact causing her bra to snap off and fly into the air. Luna quickly noticed this when she felt the night air on her bare nipples and shot her eyes open to see said bra in the air and starting to descend, only for the seagull to swoop in and take it.
“NOOO!!!” Luna got up and tried chasing the seagull but it was already getting out of sight. Luna grinded her teeth in anger over the bird but a cool breeze came by and caused her nipples to harden and Luna used her arms to cover her chest and ran over the backside of her house. She couldn’t deny or pretend this wasn’t real, she was outside in only a thong, and a tight skimpy one at that.
“Just freaking great. I’ll have to try getting to Celestia’s place for her spare key and some clothes.” She turned towards the way to Celestia’s house, but stopped in her tracks. “But if I go to her, it’ll be the skinny dipping incident all over again.” Luna could never forget that night: She went over to their secret spot for a skinny dipping session, however she realized the hard way that she locked herself out of her car with her clothes inside it, forcing her to go to the ranger’s station soaking wet and naked to call Celestia for help. It was the most humiliating experience of her life and Celestia would occasionally tease her by bringing up in some form of joke.
“If I go to her for help, she’ll have free-range to tease me until either of us dies and even in the afterlife!” Luna backed up to the wall of her house unsure what to do now until idea popped in her head. “Wait! Cherry has a skeleton key at her place and she’s waiting for me anyway.” She turned towards the direction of Cherry’s home, which was not only opposite of Celestia, but a number of blocks anyways. “Her home is much farther and I run a bigger risk of getting caught.” She looked back and forth between the ways to Celestia’s and Cherry’s. “It’s either chance humiliation with total strangers or humiliation with Celestia.” Luna took a few seconds to weigh the options. “Strangers.” Luna ran towards her girlfriend’s home, keeping her arms across her chest.
Luna was reaching the end of her second block, taking a moment in a backyard to pull the backside of her thong that kept riding up between her cheeks.
“This was not made for running.” Luna commented.
Just then the lights from the house she was behind went off near the door, Luna noticed this and ran behind a tree. The door opened up for moment and soon closed.
Luna sighed in relief and walked off, only to kick into something, she looked down to see it was bowl of dog food now scattered all over the lawn. She then heard growling from the side and turned her head to a doberman not too fond over it’s food being knocked over.
Luna gave a nervous chuckle. “Oh whoops. Look boy, you’re not the only one who's had a bad night, how about you-”
“WOOF!! WOOF!!!” Doberman barked.
Luna took her chances and booked it with the doberman in pursuit.
Two ran through the remaining yards on the block as the doberman caught up and tried to bite Luna, resulting in it getting her thong in it’s teeth, snapping the teeny undergarment right off. The doberman stopped to devour said thong. Luna was so caught up in running away to notice any of this.
Minutes later Luna tripped over a shrub leading to another yard landing on her belly ass up. Like her breasts before a breeze across her ass and pussy alerted Luna to their exposure. She scrambled up to see the truth herself.
“Of all the rotten luck.” She took a hand to her pussy and another to her ass to cover them up only to remember her breasts were still exposed. A few minutes of trying different poses she knew she couldn’t cover all three of her private areas. “It’s no use. I just have to keep going.” Luna make her way forward with her arms over her breasts and a hand over her ass, figuring her pussy wouldn’t get as much attention while she ran.
Luna made it past another two blocks, reaching the end of middle class part of town and also at the beginning of the richer part of town. However, there was something between them: A Mini Golf course with plenty of people around.
Luna currently behind a tree looking over the place. “It’s so big and the way around is too long.” Luna swallowed the lump in her throat. “I gotta risk going through the course.”
Luna ran over and climbed the fence after she was sure no one was looking where she was. After getting on the other side she snuck around the attractions on the courses, sometimes for a few seconds to minutes depending on anyone playing the hole around her. However her legs were starting to feel sore, spotting a windmill she checked around it and found a door on the back, opening it and going inside.
Luna sat down in the middle and tried catching her breath. “Just. A Quick. Rest.” She said to herself between breaths.
As Luna was resting five young girls from CHS were approaching the hole for the windmill.
“Alright, this one should settle the game.” Diamond Tiara said.
“Who’s up first?” Applebloom asked.
“I’ll go.” Silver Spoon replied. She set up her ball and took and moment to ready herself and then putted her ball. It bounced around the lanes and made through the hole in the windmill.
However as the ball went in full speed it collided with Luna’s butt, though she didn’t notice, and it came back out the entrance.
As the girls went over to the back end for Silver to finish they spotted the ball coming back out.
“Huh?” Sweetie Belle asked. “What happened?”
“Maybe it bounced against the inner walls.” Scootaloo suggested.
“Great. Now I gotta do it again.” Silver muttered. She once again putted her ball in only for it to come back out. “Seriously? I couldn’t of hit a wall again.”
“Maybe something’s blocking the way.” Applebloom said. She then got down and reached her hand inside the windwheel, and ended up grabbing Luna’s rear while some of her hair was over it. Freaking the two out.
“AAAAHHHH!!!” Applebloom pulled her hand out backed away.
“What’s wrong Applebloom?” Scootaloo asked.
“I felt something hairy and soft!”
Luna’s face was red now knowing who touched her.
“You think it’s a animal?” Diamond asked.
“What’s going here?”
The girls turned to an approaching employee.
“We think there’s an animal there.” Sweetie answered
Luna was freaking out in the windmill knowing others were aware of her and she couldn’t try getting out without being spotted by her students, but would be exposed either way if the employee open the door.
“Should we get it out?” Scootaloo asked to Luna’s dread.
“No. It might be too dangerous.” The employee replied giving Luna a sigh of relief. “We gotta put it to sleep.” Luna’s face turned pale and her eyes turned to pinpoints.
“You mean we have to kill it?” Silver asked.
“No, we put to actual sleep and let animal control pick it.” The employee replied.
Either way this was terrible for the freaked out naked woman.
Another employee arrived with what look like a leaf blower. “Alright, this gas contains a strong sedative that will have whatever’s in there sawing logs in no time.” He put the nozzle into the entrance and started releasing the gas.
Inside Luna was on her feet watching in horror as the gas was coming filling the place up.
I gotta do something. ANYTHING!
Desperate, Luna started pushing the wall of the windmill with all her strength, making it to fall over, causing the gas to spread to the employees and the girls. With them blinded and coughing Luna booked it out of there.
After getting out of the Mini Golf course Luna was standing in the middle of a street, hands on her knees, trying to catch her breath only to go into a coughing fit.
Must of inhaled some of that gas.
Luna rubbed her throat as she coughed to get it out of her system.
“What the hay?”
Luna’s eyes almost burst out as she turned to see an old lady with thick glasses and a walking cane.
“Is that some kind of animal?” The old lady was saying to herself.
Must have poor eyesight. Not that I mind.
Luna tried to answer only for a wheeze to come out, followed by another coughing fit.
“You threatening me ya yermin?!” The old lady started shaking her cane at Luna. “I ain’t afraid to use this!”
Luna tried waving her hands and started backing up before another coughing fit came.
“That’s it!” She started swinging her cane.
Luna turned around to run, getting a whack on the ass in the process. She wheezed in pain and tried to get a move on only for the old lady to follow her and get a few more hits in on Luna’ ass until Luna eventually outran her chaser.
After outrunning the old lady Luna snuck her way into the patio of a house to hide it out, she laid on all fours while she tried getting all the coughs out of her.
“AAAAAHHH!!!” Luna took a deep breath. “I hate seagulls, dogs, and old ladies so much right now.” Luna let out a sigh. “At least I can talk again.” Luna tried to rub her butt only to hiss after contact. “Dang she did a number on me.” She turned her head and spotted the patio’s swimming pool and stared at the water while ignoring the floating platform in the middle, she crawled over to it and dipped her finger in and it was certainly cold. “Might be what the doctor ordered.” She looked up at the house and saw no lights were on. “Wouldn’t hurt to try.”
Luna sat herself by the edge and dipped her butt in the water, while it sent a chill up her spine she felt a wave of relief for her abused tush. “Aahh!!” Luna couldn’t help but enjoy the feeling until…
“Who’s this?”
Luna reacted like when the old lady called her out, though to her surprise this time it was a couple of college kids, all as naked as she was.
“Who invited this old lady.to the skinny dipping party?” One of the guys asked.
“Old lady?!” Luna rose up and confronted the guy to called her out. “I’ll have you know I’ll 31!”
“Whatever party crasher!” One of the girls said. “Could you get out of here? We’re about to have our butt battle.”
“Butt battle?”
The girl pointed to the platform floating on the pool. “Two stand on that and fight with their butts to knock one into the water. All to prove who’s got the best ass among us.”
Luna pinched the bridge of her nose. “That sounds completely stupid.”
“Yeah you’d say that.”
“And why is that?”
“One: You’re old. And two: your butt couldn’t handle it.”
“What?”
The girl turned about and pointed at Luna’s butt. “Something that big gotta be fake, like implants for something.”
Luna’s clenched her fists in anger. This chick struck a nerve.
She turned to face her mocker. “Listen here you! This butt is 100% percent natural and could put any of ours to shame.”
The girl raised an eyebrow. “Oh yeah?” She got up to Luna’s face with a smirk. “Prove it.”
Luna’s narrowed her eyes as she got up to her opposer’s face. “You’re on.”
The two soon stood atop the floating platform. Everyone else was cheering, but Luna and her opponent facing each other and ignored the others. They turned around with their butt now facing each other. One of the guys told them to begin.
Luna’s opponent took the initiative, striking Luna’s rear causing the Vice Principal almost topple over, Luna hated to admit it but her butt made an easy target, she managed to regain balance but her opponent kept up her assault with several hits almost took Luna out.
“Come on implants, I thought you were gonna put us to shame.”
“That’s it. I’ve been pushed around enough tonight.” Luna whispered.
Luna steeled her and and waited for her opponent’s next attack to strike back making their butts collide, this time it was her opponent trying to stay on. Luna’s butt may have been an easy target, but could also hit pretty hard. Using this opportunity Luna made a strike with enough force to send her opponent falling into the water.
The others stood in awe as their friend lost.
“YES!” Luna happily cheered for herself.
Luna’s opponent popped her head out of the water and swam out of the pool in defeat.
Luna’s pride soared as she watched her opponent get out of the pool and grumbled at her loss.
“Lucky.” The girl said.
“Oh, it ain’t luck.” Luna replied, getting everyone attention. She put her hands on her hips and gave them a cocky look. “Who else wants a piece?”
The other girls challenged Luna to avenge their friend’s loss, but one by one they were toppled by Luna. After all the girls were defeated Luna challenged the guys to take her on. And either stupid or perverted enough they gave it a go, only to go down as the girls before them did. Once everyone was defeated Luna swam out of the poll, took one of the skinny dipper’s towel to dry her off, and stood before the soaked college kids with pride. “So, still think it’s just implants?”
The kids look at each other and nodded in some agreement. One of the guys walked over to their things grabbed some kind of stamper and a phone.
Luna wondered what they were doing until one yanked the towel she was using off her. “What the-” She interrupted as her ass was stamped and the guy took a photo. Luna turned to him in anger. “What do you think you’re doing?” She was then shown the photo of her ass and what the stamp was: It was five stars lined like a rating and “ASS” in big bold letters under it. “What is this for?”
“To prove you’ve got the best ass here and are the butt battle champion!” The guy who stamped her said.
Everyone then cheered for Luna who blushed in modesty for this. However something came up in her head. “Uh-oh! I forgot about Cherry! Look I gotta go, there’s someone waiting for me.” She was about to get a move on when she remembered her state of undress. “Um, do any of you have some spare clothes?”
“I do.” The girl who first challenged her replied. “Come on, I’ll give it to you.” She lead Luna indoors.
Luna left the house with a baggy yellow shirt, pink sweatpants, and flip-flops.
“Better than nothing.” Luna said to herself. She made her way towards Cherry’s house at a more casual pace now that she was dressed. Until she heard a familiar sound.
“WOOF!! WOOF!!!”
Luna made a sharp turn to see the doberman running towards her.
“OH COME ON!” She started running again. “You already took my thong! I’d say we’re even!”
The doberman got up to the Luna and chomped on her sweatpants, causing her to trip and lose her flip-flops, she landed with her ass in the air for what felt like the dozen or so time this evening. The doberman managed to yank off the sweatpants and started shredding it. Luna took the chance to get up and started running again. The doberman tossed the pants aside to presuade Luna again, getting its teeth on Luna’s shirt and with them both running the shirt tore off Luna’s body, leaving her naked once more.
“YOU’VE GOTTA BE KIDDING ME!!!” Luna yelled as she kept running
You’ve reached Luna, can’t talk right now so leave message.
Cherry Jubilee heard this for the seventh time. Waiting for Luna, she checked her reflection making sure she still looked good, her ruby dress shined and her hair flowed down.
“What is taking that woman so long?” She asked to herself.
“AAAAAHHHHHH!!!!!!!!!!!!”
The scream caught Cherry’s attention, she looked out the window and to her shock saw a naked Luna hanging from a tree branch with a doberman barking at her.
“Leave me alone already!” Luna yelled.
The doberman kept barking and tried jumping up to her.
BANG!
Both Luna and the doberman’s attention to went Cherry with a shotgun.
“Get away from her mutt!” She pointed her gun at the dog and loaded it.
The dog growled and ran off.
“Cherry, thankness goodness you-WHOA!!!” Luna lost her grip and fell.
Cherry ran and caught Luna in her arms bridal style. “Are you okay Luna? Why was that dog after you? And why are ya’ll stark naked?”
“I’ve have a long night Cherry. I’ll tell you inside.” Luna replied.
“My stars! I can’t believe you went through all that.” Cherry said as she was massaging Luna’s sore body.
“I wouldn’t believe it if I didn’t myself. OOOOHHH!!!” Luna said Cherry handled her back.
“Just be glad it’s over for you-” Cherry started caressing the cheek that was stamped “And your Five Star Ass here.”
Luna gained a deep blush for Cherry touching that area. “S-Still a shame about dinner.”
“Don’t worry about that. There are other ways for us to spend our evening.” Cherry replied as she took her hands off Luna.
Noticing this, Luna turned her head to see Cherry walking over to her dresser. While so, she pulled the straps of her dress down and let the dress fall off, revealing she had no underwear on. Rummaging through the dresser a bit, Cherry starting putting on a pair of panties to Luna’s confusion. That is, until she turned around to show the front had long plastic cock on it that Cherry starting stroking. Cherry then put on a cowboy hat, raising it up a little to give Luna a seductive look.
“We can have our own private rodeo, darling.”
Luna cracked a smile and gave Cherry her own seductive look.. “If that’s the case-” Luna got on all fours, turned around to showing Cherry her ass and shook a little to invite her over. “Ride’em Cowgirl.”
Author's Note
If anyone wants a follow-up chapter or picture from Luna and Cherry's evening plans. you can commission me.
