Just Winging It

by Freakeasy

Chapter 3

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Author's Note

As I intend this to be, hopefully, a more plot-focused story, I feel it would be helpful to at least point out when chapters will cross over into clop territory. There is always going to be sexual humor, that's the nature of my character, Jimmy, but I will try to make him behave otherwise, :pinkiecrazy:

So this one will feature an adult scene, just fair warning. :unsuresweetie:


Chapter 3

The pair set down on the front porch of a large, floating cloud mansion.

Rainbow let Jimmy go and, thankfully, the bat was indeed able to stand on the steps leading into her home. She pulled the door open using her right wing then stepped aside to let her guest in, “Well, here we are. Cloud sweet cloud! What do you think?” Why did she suddenly care what a guy she’d just met thought of her home?

Jimmy walked in, his bare feet cold against the smooth tile floors. He looked around, the place looked like an ancient Greek temple mixed with some old one-percenter’s fancy manor. The staircase which led up to where he assumed Rainbow’s room was had a gorgeous red carpet over a black and white checkered tile and the railing had those beautiful Greek columns lining it from foyer all the up to the mezzanine. Jimmy finally answered Rainbow, “Damn, Rainy! You know, for such a rough an’ tumble girl, I would never expect somethin’ this fancy!”

Rainbow blushed while rubbing her head with a wing, “Oh, its really just a hand-me down. I had it moved here straight from Cloudsdale, that’s where I grew up. The best city in the sky! So you really like it?”

The bat smiled and he nodded, “Hell yeah! This is some badass digs ya got here! Tell me, y’all get some dirty, naked freaks up in here sometimes, huh?” He jabbed her playfully.

She blushed more, “Oh no, not exactly. Not everyone in Ponyville can actually come up here. This place is mostly clouds and only winged creatures, or ponies who know a unicorn with a cloud-walking spell, can actually walk around up here, so no I don’t have a lot of parties up here. All our parties are pretty ground-based, though if you like those dirty, sex parties, Pinkie does have those, but only for certain nights and ya gotta sign under the desk for that sorta thing.”

Jimmy smiled, “So you’ve been to these sex parties?”

RD flustered, “N-no! Of course not! I already said, I’m not that kinda mare!”

The bat grinned, “Well, between you an’ me, I am that kinda bat, though for your sake, I’m just gonna leave it that. I don’t think your face can take that much blush.”

The pegasus coughed uncomfortably, “Yeah... Uh, so, let me just show you around and then we could get some sleep.”

The bat with those intimidating red eyes took a winged bow before her, “Lead the way, Master.”

RD’s cheeks turned an even darker purple from all of his endless teasing, “O...kay, just this way.”

...

“And down that way’s the bathroom, and by the way,” Her cheeks had returned to a bluish violet at this point, “if ya need to, you know, careful when you flush, sometimes you can get sucked in and yeah that’s not a pleasant experience.”

Jimmy had to stop when he heard that, “Well, there’s an image to haunt my dreams.”

Rainbow laughed now that she’d finally gotten him back for all the teasing, “Yeah, it’s better you know now than later when you’re possibly plummeting to your death.”

The bat shook his head while his irises shrunk, “Nah, it’s not even the dyin’! It’s the whole gettin’ sucked out through a... That’s just wrong! I know I like nasty stuff, but I gotta draw the line somewhere!”

The pegasus snickered, “It’s okay, just don’t stand too close to it when you flush... Can’t tell ya how many times I’ve had friends who got stuck in there... I won’t say more because hey, I respect my friends too much, but some of ‘em never use it when they come up here anymore. They usually make sure they’ve done business before comin’ over.”

The bat’s face had paled from such a colorful description about cloud mansion bathroom etiquette. He bumped Rainbow with his hip,
“Okay, I get it! Ya got me back for all my assholery before; happy?” His face was pleasant mix of annoyance and mirth.

Rainbow laughed, “Very!” before she trotted down the hall towards her room. She stopped when she got there, “Now... I don’t really have the guest room set up, usually I gotta be told in advance if somepony’s gonna come and sleepover, and it’s already late so...” She took a breath before finally spitting it out, “If you promise to behave and keep your claws to yourself, you could stay in my room with me for the night.”

Jimmy smiled, “That is a nice offer and a great show of trust, but I wouldn’t ask to put yourself out for my benefit. I can just sleep out here... I was homeless once, I’ve slept on cold floors before.” He showed off his wings, “God gave me two built-in blankets to keep myself warm after all.”

The cyan pegasus shook her head, “No! No, you don’t have to do that... I-I want you to stay. Other than Fluttershy, Derpy, the few other pegasi friends I have around here, I don’t often have somepony I could talk to up here.”

Jimmy smiled, “Well, you are someone fun to talk with... But,” But what? Marina’s not here; she’s home probably losing her mind over you.
He shook his head, “Okay, I’ll stay with you and I swear I won’t bother you in anyway. I may paint myself as kind of a freak, but I do have my standards, and number 1 is I treat all my bedfellows with total respect whether it’s a sexual thing or not.”

Rainbow looked at him, “Well, okay... So, I guess all there is to do is just to turn in and get some shut-eye?”

He nodded, “Sure thing, Rainy.”

They went into Rainbow’s room and to Jimmy, it looked like exactly what he would’ve thought of this rough, tomboyish little pegasus. What he saw was a room plastered with posters of the famous aerial team, the Wonderbolts. What he didn’t see of them, he saw of some Indiana Jones-type explorer named Daring Do that just looked like Rainbow with a different color scheme to him. He looked at that some before he saw some of the pictures Dash kept on her dresser drawers. He picked up a little portrait of her with five other ponies and one little purple dragon. He recognized Rarity.

Rainbow saw him with the picture of her friends, “Yeah, that’s me and the girls!” She pointed to each with a wingtip, “The purple brainiac there is Twilight Sparkle, she’s the Princess of Friendship! There’s Applejack, you really do sound like one of her cousins by the way and... I should probably introduce you to her last... She’s not a particular fan of bats since that time a whole swarm of ‘em nearly destroyed her whole apple orchard. There’s Fluttershy; she loves animals but she’s real timid. We grew up in Cloudsdale together so I’ve known her longer than any of them. You already know Rarity, that’s Pinkie Pie... I should probably prepare you for her too, she is very random. And the little guy there is Spike. He’s been Twilight’s assistant for years, he lives in the castle with her.” She leaned in closer, “He’s got a major crush on Rarity, though everypony already knows anyway. You’ll see him at her place more often than not, he’s always helping her when he’s not helping Twi.”

Jimmy nodded, “Quite an interesting bunch you surround yourself with... Sure wish I had a picture so I could show you my friends.”

Rainbow climbed into bed while Jimmy sat next to her, “You could tell me, I’ll try to picture them in my head.”

Jimmy shrugged, “Okay well, there’s Jacob, he’s kinda the leader of our group. My best friend, though we don’t always agree on things, such as how hot I think we’d both look if he just went gay a little.” He snickered, “There’s Jill, his girl, Hidaya, she’s his girl too... Sometimes a guy gets all the luck. There’s Jonny, Desiree, Jill’s brother, James and her adopted sister, Isabella, then there’s...” He stopped, “Marina.”

Rainbow felt something from the way he’d said that last name. She had to ask, “And who is Marina?”

Jimmy petted Rainbow’s mane as he thought of the pretty otter he’d left behind, “Marina Roosevelt... She’s my girl. We’d been living together for some time now and we were thinking about eventually getting married and now...” He grew more mores, “Now I’m here.”

Was this jealousy? Rainbow thought to herself, for a girl that’s not even here? She shook her head, “Don’t worry... When we go to see Twilight tomorrow, I’m sure she could find some way to help you.”

The bat smiled as he suddenly hugged Rainbow again, “Thank you. You’re a good friend, Rainy.”

She was blushing again when they separated, but this wasn’t an embarrassed blush. This one felt good, like she’d really helped her friend feel better about his situation. She scooted over to her side of the bed, “So... I guess I’ll see you in the morning?”

The bat just remembered something, “Oh, Rainy! I just remembered, and please don’t be mad.”

She was already yawning, “What would I be mad about?”

Jimmy smiled at her, seemingly a little embarrassed for a change, “Well the thing is I sleep in the nude.”

She stopped mid-yawn when he said that. Already images of his junk out in the open sprung to her mind, “Oh... Uh, well, I’m always naked so that’s not strange and... I guess I did already see your stuff before so...” She blushed, “Knock yourself out!”

Jimmy already had the loincloth untied but he still hesitated, “Are you sure? I wouldn’t want to make you uncomfortable.”

Rainbow giggled, “Jimmy, it’s not a problem. You just stay on your side, ‘member?”

He joked, “Yeah, and I’ll make sure Little Jimmy ‘members too.” So then, he took off the loincloth and let his privates out.

Rainbow’s eyes widened as soon as them out in the open. She’d looked at the odd stallion and seen the weighty pairs that they had dangling. Jimmy’s were a tad bigger than a typical stallion, and not as smooth looking, covered in the same bushy gray fur as the rest of him. She’d also, on occasion, seen a colt whenever he’d been aroused. Their penises were fairly large, though she’d never personally perused a stallion. Jimmy’s had a similar floppiness and thickness, but he did seem lengthy, and where stallions had a sheath to contain their malehoods, he had a loose skin wrapped around his like a tight sock.

Rainbow had been so focused on her dreams about being a Wonderbolt she’d never devoted much else to her relationship status. Now she was a Wonderbolt and still as much a curious virgin as she’d been in flight school. Seeing Jimmy this close was awakening a feeling she didn’t know existed in her.

Jimmy noticed, how would he not notice a girl staring at his dick for the last thirty seconds? It flattered him that she was so interested but, he’d already promised that he would respect her boundaries. He pulled back the quilt on Rainbow’s bed then slid himself under, “Well, we could just sit there an’ keep lookin’ at each other’s privates, but I think it is more vital that we get a good night’s sleep, eh?”

Rainbow blinked once he’d covered his maleness with her blankets, “Huh? Oh, oh yeah, right... Um, good night, Jimmy.” She smiled. But then, as soon as the bat had gone to sleep, Rainbow mumbled to herself, “Oh Celestia... I want him.”

...

“Mmm, now who is this?”

Jimmy’s alert ears wiggled. He was dreaming, he was home surrounded by friends and family. There was Jacob, the handsome black rat with the two lovely females, a ferret named Jill and a meerkat named Hidaya. Hidaya, to Jimmy, was especially sexy with her more petite body, green eyes, red hair and the fact she could easily kick his ass if he so much as looked at her wrong.

Over there was the bodacious beaver, Desiree with her two handsome men, Jonathan, a wispy brown squirrel and James Jr, Jill’s “Baby Brother” as she always referred to him.

He looked to the right and there he saw his family, what family he had anyway. There was his little brother, a mute coyote named Robert and the old roadrunner who cared for the both of them, Miguel.

Then there was Marina... The otteress staring back at him with those beautiful brown eyes, that long dark brown hair, those magnificent breasts, her wide hips, that cute Australian accent of hers, “Jimmy...”

“Now, who could you be?”

He heard that voice again, a female voice, one that sounded regal, very important. He turned his eyes once more until they fell upon a great, beautiful, navy blue alicorn with a flowing mane which resembled the night sky.

Jimmy blinked, “Who are you?”

The alicorn spoke to him kindly, “I am Luna, stranger, Princess of the Night.”

He blinked, “One of the royal sisters of this land?”

Luna smiled, “Indeed, thou hast heard of us?”

The bat nodded, “Yeah... You’re real pretty but, what is this?”

She blushed, “It is one of my many duties, to gaze into the dreams of the many denizens of our land. I had seen your door but did not recognize the symbol, this symbol.” She pointed to the tattoo on his chest.

Jimmy looked back at her, “This symbol, I guess like the cutie marks of your ponies, it is the source of my power... I am magic too, but a different kind.”

Luna brushed her hoof over his bare chest, “Fascinating, I wish I could stay longer, but I must depart. I do sorely wish to meet you, in the flesh!”

The bat joked, “Well I’m already naked, so we’re already there.” He snickered as his comment had made the princess blush.

“Yes, well...” She tried to think of something, before she just abandoned the dream altogether.

...

The next morning, Rainbow had awoken before Jimmy. The cyan pegasus opened her pretty magenta eyes then looked at her friend while he slept. She felt that feeling again, that warm feeling. She leaned in to sniff him. There was an earthiness to his musk; he really smelled like he could have been an earth pony.

She shook her head; she shouldn’t be feeling this way. He’s not even the same species.

He was still so cute, though.

She pushed off the quilt so she could get out and try to shake off this feeling, then she saw it.

Jimmy’s Little Jimmy, though she couldn’t really call that thing little, had stood up on its own, the loose skin peeling slightly to expose the round tip beneath.

Rainbow shielded her eyes with one of her wings. She shouldn’t have looked, but now she had and now that feeling was stronger. She brought her wing down and the thing was still sticking, maybe not up, but definitely out. She had a thought. She looked up to see he was still asleep, then back down to his... Thing.

Jimmy slept peacefully for the next few seconds before he felt something rather warm brush against his prick. The bat was always a light sleeper, especially concerning matters of sex. He opened his bright red eyes and caught sight of a blue wing wrapped around him, its soft feathers tickling him while a certain pegasus found it hard to follow her own bed rules apparently. Not that he was complaining, but if someone says no touching, he would expect some unspoken agreement that the other person would do the same. At the same time, he’d never been jacked off with a wing before and he was always eager to try new things. So he let her, remembering to close his eyes each time she seemed to peer back up to make sure he hadn’t woken yet.

Rainbow looked at it while she played with it, it was like she had found a new toy now all she wanted to do was play. It felt firm in her wing, felt warm. She smelled it; that earthy musk was even stronger with a hint of something salty. She looked at it as it twitched and a droplet of some clear stuff dribbled from his tip. Before she could stop herself, Rainbow licked it.

Jimmy bit his lip to hold back on the moan he gave from her tongue flickering over his tip. He hadn’t even touched himself within the last 24 hours, a new deal for him he realized. He looked at her while she seemed to register his flavor.

It was salty, but not unpleasant. She continued to stroke him with her wing and as she saw more dribble out, she licked more, slowly getting bolder and more forceful with each pass of her tongue.

And for a bat who was typically proud of his own self-endurance, things predictably didn’t last long after a whole day’s worth of abstinence.

The bat moaned as he felt himself twitch then shoot into his new friend’s open mouth.

She’d been surprised when it happened, then found she liked the taste of this stuff even more. She put her cute snout over the tip and let those salty fluids pour down her eager gullet. She broke off eventually and let those last few strands shoot across her face while she relaxed with her cheek nuzzling his dwindling length. It was only then she looked up and saw his bright red eyes looking down at her. She gulped, swallowing the last of his cum while her cheeks flushed violet with blush. She sat up about to apologize when he interrupted her.

“It’s okay, Rainbow... It ain’t the first time I woke up to this.” He smiled, “I liked it, by the way. Thank you for the wake up call.” He winked at her while that signature grin of his spread across his muzzle. He beckoned her with a simple flick of his wrist.

Hesitantly, she crawled up until she was nearly nose-to-nose with the bat. He was definitely smiling, clearly not upset with what she did.

She nearly flinched when he put his hands on her, then moaned when his long, tapering tongue ran up her face, lapping up some of his own semen from her pristine, blue fur.

Dutifully, Jimmy licked up every stray strand that had painted his friend’s face. He then regarded her with the same friendly smile he always wore before gently, but persuasively pulling her muzzle against his own.

Rainbow had kissed other ponies, she wasn’t completely clueless when it came to expressing affection. She’d kissed Fluttershy and Derpy on occasions, both were quite receptive to her advances but she never went beyond kissing. She felt the bat’s tongue tickle her lips, she opened up then felt his long tongue slide in, to lap at the remaining cum still in her mouth.

She shivered when she realized this bat was tasting himself and clearly enjoying it, and she shivered from the sheer electricity of his tongue brushing against hers. His muzzle was many times bigger than hers yet their mouths still somehow fit.

Eventually, Jimmy had collected enough of his own stuff. He pulled back to swallow before he finally spoke, “Thank you.”

Rainbow blushed, “D-don’t mention it.”

...

The two sat together in Rainbow’s kitchen afterward.

Neither were very hungry, not from the salty supplement they’d just shared.

Jimmy eventually broke the silence, “So first off, I’m not upset, clearly, but definitely some boundaries were crossed there.”

Rainbow blushed, “Yeah... Sorry I couldn’t control myself but... I’d never done anything like that before. I’d hear other pegasi brag about this stuff, but I never tried it. I wanted so much to be a Wonderbolt, I put everything else to the side for that dream. Now I am a Wonderbolt and I still know next to nothing about this stuff.”

Jimmy chuckled, “That was damn good for a first try, though. A+ plus in my book.” He pinched her nose playfully, “And... While I would respect that this probably won’t happen again, I wouldn’t object if it did, as long as both of us are coherent and willing. The one thing I never, ever do is take advantage... That’s not me, not at all. Miguel brought me up to be better than that.”

She nodded, “That’s good... And I will make sure to ask... Because that was pretty fun.” She was still blushing but this was that feel-good blush. “Who’s Miguel?”

Jimmy smiled, “Well, he’s kinda my dad...”

She quirked an eyebrow at that, “How is someone kinda your dad?”

The bat explained, “Well, we weren’t exactly related. He’s a bird, a roadrunner. He is also the guy who saved me from a life on the streets an’ took me in as his own. Everything I know about bein’ a gentleman, I learned it from him. For the longest time, it was just the three of us. Me, Miguel and Robert, he was my brother, again not by blood. Rob is a coyote. I hope he’s doin’ alright without me. That boy has this shyness like you won’t believe, he don’t even talk to people. And it’s not like he was born mute, he can talk and does, but not around other people. Most of the time he just writes whatever he’s thinking so he talks to our friends through his little notes.” He nearly teared up from thinking of the shaggy brown canine.

Rainbow said the first thing that came to her mind, “It sounds like Robert and Fluttershy would get along.”

Jimmy smiled, “So... About us goin’ to see this princess friend of yours.”

Rainbow had completely forgot, “Oh right... She’s probably up by now so we should get going.” She got up, her hooves clopping on the tile floor, “Come on! I can fly you there so nopony sees you in your loincloth.”

...

The pair of them set down on the steps of the Friendship Castle. Rainbow knocked on the double doors, “Twilight!”

The doors opened and a cute little purple and green dragon stepped out, “Oh hey, Rainbow!” He nearly shrieked when he saw the large bat,
“Whoa!”

Jimmy smiled, “Howdy!”

The dragon stammered, “Uh... Hi?”

Rainbow shouted, “Spike! We need to see Twilight!”

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