A Tryst in the Night

“Oh, wow! This is so awesome, Thunderlane!” Rumble trotted inside their hotel room and let his saddlebag slip from his back. Two beds lay next to each other on his right, separated by a nightstand that a sole lamp sat on. On the other side of the room was a small desk with a chair, complete with a fully-stocked mini fridge.

Rumble wove his way through the room and slid open the glass door that led to their balcony. Luckily for them, his big brother was able to save up enough money to go on a vacation to the beach. The Baltimare hotel room had an ocean-side view, giving the boys a grand view of the beach that lay just behind the pool. Rumble looked to the right and saw a line of houses stretch out into the ocean, all connected by one long dock.

He stepped outside, his mane blowing in the wind. He closed his eyes and smiled, then opened his wings. A particularly strong gust lifted him off of the ground, making him open his eyes in shock. His wings snapped shut and he dropped back to the balcony, his legs a little shaky.

“Heh, gotta be careful about that sea breeze, Rumble,” Thunderlane said as he walked up behind him. “Those things can come out of nowhere.”

“Yeah, no kidding,” Rumble muttered. His brother stepped up beside him and sat down. “So...” He nudged Thunderlane on his shoulder and chuckled. “What do you want to do first? Wanna go swim in the pool? Maybe the ocean?” He looked back around and eyed the vast expanse of water. “How deep do you think it is?”

“I have no idea, dude. This is the first time I’ve been out here.” Thunderlane sat down and peered over the railings, then he smiled down at Rumble. “You know, I think I have a better idea.”

“What’s that?”

Thunderlane chuckled and nudged him back. “Let’s go to the bar and pick up some chicks!”

“Oh, uh...” Rumble chuckled nervously and rubbed the back of his neck. “Yeah, I’m down to go the bar, but can we hold off on picking up chicks for a bit? We did just get here, after all, and I’d like to relax a little.”

Thunderlane glanced up and rubbed his chin as he thought. “Well, I suppose we can do that.” He glanced over the railing and grinned at him. “Ya know, I think that’s the bar down there! Wanna just glide down? I don’t feel like walking down all of those steps.”

Rumble bit his lower lip. “Um... I don’t really feel like flying, ‘Lane. That breeze kinda shook me up.”

“Oh... okay then.” Thunderlane shrugged and laid a wing over his brother’s back. “Let’s get going. Those drinks ain’t gonna drink themselves!” he said with a chuckle.

“Yeah, true.” Rumble chuckled as well. As they made their way down the hallway, he said, “You know, I’m glad I finally turned eighteen. At least we don’t have to worry about Mom and Dad finding us drinking again.”

“Pfft, yeah. I didn’t like how Mom lectured me for being a bad role model for you for a half hour.”

“And then Dad bitched at you for another hour for giving me alcohol before I could drink legally.”

“Yeah... that wasn’t a good time...” Thunderlane shook his head as he nudged open the door leading to the stairs. He folded his wing back to his side and motioned for Rumble to go first with a hoof.

“But now we don’t have to worry about that anymore because we don’t have anyone to tell us what to do!”

“Damn right, Rumble.”

The two of them made their way all the way to the ground floor. Having their room on the ninth floor made the walk down a little monotonous, but the promise of drinks and hot mares spurred them on. They emerged into the hotel lobby, and after looking around for a few seconds, Rumble located the hallway leading out to the outdoor bar.

Rumble nudged Thunderlane and nodded in the direction of the bar. “I think it’s that way, dude.”

“Awesome. Lead the way.”

Rumble nodded and sped up a bit. They turned a corner and made their way down the length of the hallway then emerged out onto the pool area. He stopped, making his brother walk right into him.

“Dang dude, why’d you sto... woah.” Thunderlane’s jaw dropped as he saw what his little brother was looking at. Sexy mares lined the pool, all of them wearing the skimpiest of swimsuits. He couldn’t help but stare at them, their curves captivating his eyes. His eyes drifted from mare to mare, each as cute and hot as the last.

“Yeah.” Rumble felt his wings start to rise. His eyes going wide, he frantically hid behind a bush and thought of as many unarousing things as he could. Thankfully, he was able to fold his wings back to his side after several moments of thinking about regular things. Dirty dishes… sandy wings… He stood back up and nudged Thunderlane, breaking him out of thought. “Want to get some drinks?”

“Hell yeah!” Thunderlane lifted his head high, squared his shoulders, and fluffed his wings. He flipped his mane to the side and shot a confident smile at Rumble. “And once we get some liquid courage in us, I’m gonna give you a crash course in Thunderlane’s Tips and Tricks on how to pick up mares!”

“A-awesome!” Rumble chuckled, though his tone was a bit nervous.

Thunderlane shot him a strange look, then smiled slyly at him. “Hehe, you’re a virgin, aren’t you?”

Rumble looked anywhere but his brother. He rubbed the back of his neck, bit his lower lip, and swished his tail from side to side. “Uh...” He debated not telling the truth, but Thunderlane had never lied to him, so he surely wasn’t going to start now. “Yeah... yeah, I am,” he muttered.

Thunderlane laid a wing over his back and gave him a noogie. “Ain’t nothing to be ashamed of, Rumble. Think of it like this: what place could be better than this to lose your virginity?”

Rumble perked up at that. “Heh, yeah, I guess you’re right. This place is pretty tight.”

“And the mares are even tighter...” Thunderlane whispered into his brother’s ear as a pair of hot mares trotted past them, giggling at each other. Their tails were hiked up higher than normal, each of them wearing the smallest pair of bikini bottoms imaginable.

Even though he was much more experienced than Rumble, Thunderlane had to struggle to not pop a boner.

Thankfully, the bar was not much farther. They snagged a pair of chairs that lay between a cute blue mare and a lonely-looking light brown stallion. Thunderlane glanced at what everypony else had at the bar until a certain orange drink caught his eye. He waved at the bartender. “We’ll have two of what that pony’s having!” he said with a smile, pointing at the drink that caught his eye.

“You wanna start a tab?” the bartender asked, his voice low and rough.

“Yeah, sure. We’re gonna be here for a while.” He smiled at his brother. “Ain’t that right, bro?”

“Oh yeah!” Rumble let his legs swing free over the chair’s seat, curious as to what Thunderlane had just ordered them. “Do you even know what you just ordered us?” he asked with a chuckle.

“Nah, but it sure looks good. I love fruity drinks!” They waited in silence, sneaking glances at the scantily-clad hotties that strutted their stuff around the pool. Once their drinks arrived, Thunderlane wasted no time at all. He lifted the glass up to his lips and tilted it back. “Hmm... tastes like a fuzzy navel, so it must be a fuzzy navel!” he said with a chuckle.

“Dang bro! You’ve already gone through, like, a third of your drink!” Rumble exclaimed with a chuckle. “If I didn’t know any better, I’d say you were an alcoholic!”

Thunderlane shook his head. He smiled and took a smaller sip from his drink, eyeing a mare across the bar. She was a light blue unicorn with beautiful soft pink eyes. Her mane was light yellow, and the tips of it curled around her neck in a way that sent shivers of excitement down his back.

She was going to be his tonight.

“Hey bro, you see that little cutie over there? The light blue one with the yellow mane?” Thunderlane chuckled and pointed at her. “Watch how it’s done, Rumble! You’re about to get your first lesson in how to pick up cuties!” After finishing off his drink, he locked his eyes on his prey and walked around the bar, praying that no other stallion would show up to take her away. He noticed that she was chatting with another mare next to her. Hm... how should I do this...

As he neared his prey, he felt some butterflies flit around in his stomach, but he ignored them. He sat down in the only empty seat next to the yellow mare, threw on what he thought was his smoothest smile, and cleared his throat. The mare looked at him, and he waggled his eyebrows at her while lowering his eyelids a bit. “Uh... h-hey there, cutie-pie!” he said, interrupting her conversation. She looked at him, her smile faltering. Knowing he had to act quickly, he spotted a conch shell sitting on the bar, so he reached between them and snagged it, then held it up to his ear.

Thunderlane’s eyes went wide in fake shock. He yanked the shell from his ear and stared at it incredulously. He offered the shell to the mare with a chuckle, and when she hesitantly took it, he said, “You hear that? It sure sounds like the ocean wants you to join me for a drink!”

The yellow mare sighed and scratched the side of her head. “Yeah... not happenin’, buddy.” She pursed her lips and tossed the shell back to him, then turned back and tried to start her conversation again with her friend.

Thunderlane was flabbergasted. All of his coworkers back home in Ponyville had sworn up and down that that line would work when he had told them he was going on vacation. His friends had made him feel so confident about that line, but it slowly dawned on him that they might have been messing around with him. Trying to keep his cool, Thunderlane kept his slick smile on his face and asked, “Why not? I’m a good-looking stallion!” He stuck out his chest and fluffed his wings for good measure.

The mare scoffed and took a sip from her drink. Placing her glass down on the bar, she leaned over and laid her leg around her friend’s shoulders. “Because I’m here with my wife, dummy. Now get lost.”

Thunderlane’s eyes flicked between the two of them. “...Oh, I gotcha. Wanna have a threesome with me tonight?” He licked his lips and smiled slyly at the two of them. “Ya know, I know of a few ways I can get us all wet other than swimming in the ocean or the pool. Care to guess how?”

The unicorn’s wife smiled at him and grabbed her drink. “Oh... I can think of one!” Before Thunderlane could react, she tossed her drink in his face. It made his eyes burn like nothing before. “Ah! What the heck are you drinking?!” he asked as he struggled to wipe the drink from his face.

“Straight fifteen year old whiskey,” the mare replied nonchalantly. She turned around in her seat and waved at the bartender. He nodded back and brought her a new drink moments later. “Come on, love, let’s go lay on the beach!”

Thunderlane watched in dumb shock as his former prey skipped away from him, giggling with her wife. “...Wow.” He rolled his eyes, wondering what his brother was going to think of him now. Instead of getting to walk away with a hottie by his side, he got to walk back alone empty hoofed.

Walking back to his chair, he clambered up and waved at the bartender. “Another drink, please,” he said sullenly. The bartender nodded and fetched him another drink, but not before Rumble poked his side.

“So... what happened there?” Rumble asked with a chuckle. “She not into pegasi or something?”

Thunderlane rolled his eyes and took a swig from his drink. “Nah, she was with her wife.”

“Pfft, what? You tried to hit on a married mare?” Rumble snickered and shook his head.

“Yeah, probably not the best idea,” a blue pegasus with a short white mane spoke up beside him. She shot him a friendly grin. “You know, if you had a better pick-up line than that, you might have actually been successful. The name’s Night Glider.” She held out her hoof and smiled at him.

Thunderlane bumped his hoof against hers and took a swig from his drink. “Thunderlane.” He pointed at his brother. “This is Rumble.” His eyes drifted down to her rump for the briefest of seconds. She was wearing a pair of white bikini bottoms that accentuated her curves in all of the right ways. A small white purse lay on the bar in front of her. He glanced back up to find her staring at him.

Night Glider crossed her hind legs and smiled at them. “So tell me, what brings two fine pegasi like yourselves to paradise?”

Thunderlane threw on his smoothest smile, but when Night Glider raised an eyebrow and started to frown, he got rid of it and chuckled. That’s it! I’m done trying to be someone I’m not. He ran a hoof through his mane to brush a few errant hairs out of the way. “We’re just here to let loose and party for a while. I got some time off of work, so we decided to come up here to have some fun.”

Night Glider shot him a sultry smile and let her tail brush against his left hind leg. She clenched her hind legs together and “What kind of fun are we talking about, hm?” She let her tail rest against his leg, swishing it back and forth every couple of seconds.

“Oh, uh... y-you know...” Thunderlane blushed madly and took a swig from his drink to calm his racing nerves. Oh my gosh, she’s hitting on me! He winked at her with a light chuckle and let his eyes run all over her body. Thunderlane looked directly into her eyes, then let his gaze settle on her rump a little longer than necessary. He looked back up to find her biting her bottom lip and wiggling her hips.

“I see...” Night Glider’s smile deepened. Her cheeks darkened as she blushed a light rose. Never breaking eye contact with Thunderlane, she took another sip from her drink, then glanced at his crotch. His sheath was hidden from her view. Just like he did, she flicked her gaze back up to meet his.

“So, um... what brings you here, Miss Glider?” Rumble asked once he had cleared his throat.

Night Glider smiled at him. “Just call me Night Glider, please.” She took a sip from her drink, her eyes never leaving his. “As for why I’m here, some events happened that I’d much rather not go into. I decided I wanted a change of scenery, and a drastic one at that. I used to live in a barren land that looked akin to a desert, so I wanted someplace tropical, someplace beautiful with... lots of cute stallions like yourselves.” She blushed and winked at him, then glanced down at his crotch. “And I love the scenery, too...”

Rumble saw her do so and moved to cross his legs, but decided against it at the last possible moment. He blushed madly as he spread his legs a bit, showing Night Glider what he had to offer. He grinned nervously and glanced back up into her eyes. “Ah, well... I’m glad to hear that, Mi—er, Night Glider.”

Night Glider’s smile deepened. “You know... you two seem like fine gentlecolts.” She reached for her purse and opened it. She rummaged around inside of it for a few seconds, then pulled out a single key hanging on an empty keychain. Night Glider placed it on the bar and slid it in front of the two of them. She leaned in close, lightly nuzzled him just below the ear, and whispered, “My place is out on the water, down at the very end...” She leaned up against him and pointed out across the bar, her hoof centered directly on the farthest, and biggest, house out on the water. “That’s mine, riiiiight there... I want the two of you to come over in a half hour.”

Rumble stared at the two of them, his eyes as wide as dinner plates. He watched Thunderlane nod slowly as Night Glider stood up. She grabbed her purse, tossed a few bits on the counter, and kissed his big brother’s cheek. He didn’t believe it, but his eyes got wider. She turned to him, a gentle yet slightly sly smile on her face as she locked her gaze with his. He chuckled nervously and turned to look back at the bar, fully aware that she was walking up behind him.

As he reached for his drink, he felt her hoof on his left shoulder for just a moment. He tensed up, and before he could open his mouth to ask what she was doing, he felt her place a light kiss on his upper neck, right below his left ear. A shiver ran down his back as he felt her warm breath tease him, caressing the sensitive hairs in his ear. “I want you too...” he heard her whisper. He turned to look up at her and smiled nervously. His right hind leg began to twitch, but he forced it to stop. “O-Okay,” he said.

Night Glider opened her wings and used the tip of each one to make a trail down each of their backs. She let her wings rest on their flanks, barely covering their cutie marks, then she leaned in so that only the two could hear her. “So... do you boys have any plans for tonight?” She looked between the two of them, smiling as they both shook their heads. “Why don’t you two come down to my place to, oh... you know... watch the sunset? I’m in house eleven, all the way down at the very end.”

“Sounds good to me,” Thunderlane said. He leaned forward to catch Rumble’s eye. “What about you?”

“Yeah, sure,” Rumble said, taking another sip from his drink.

Night Glider smiled at them then glanced at Thunderlane. “Wonderful. Drinks are on me, by the way.” She slid her purse under her right wing and trotted away, a sexy strut in her step. She felt both of them staring at her rear end, so she swished her tail to the side and shot a sly glance back at them. She grinned to herself as she saw their eyes widen, knowing that she just gave them a good view at the crotch of her bikini. If she didn’t know better, she could have sworn she felt her lower lips start to swell up. Night Glider didn’t know if her bottoms were tight enough to show her slightly-aroused state, but the uncertainty simply heightened her arousal.

She didn’t know if she could wait an entire thirty minutes.

Rumble gasped as she watched her show off for them. She didn’t seriously... No, she couldn’t have... right?

Thunderlane finally looked away when she took flight. He took another sip from his drink, then looked at Rumble. He noticed that he was still staring at her as she flew towards the houses, so he nudged his side with a wing.

“Bro... you see what she did when she walked away? The way she flicked her tail, hehe... She wants us, dude. I... I don’t know about you, but I totally want to go spend some more time with her.”

Rumble blushed and took another sip from his drink. His hoof was shaking, so he took an extra big swig. “...Me too, but.... the both of us? At the same time? Could we really, well, you know... go through with it? I mean, I’ve never even...”

“Well, do you want to sleep with a cute mare like that or not? Having a threesome on the first night here isn’t what I expected either, but...” Thunderlane tousled Rumble’s mane, eliciting a soft smile from his brother. “Are you okay with it? I mean, I know it’s your first time with a mare. I understand if you want to save yourself for—”

“Oh, no. I... it’s not that. Yeah, I’m nervous, and I don’t know what to expect, but...” Rumble blushed and locked his eyes down on his drink. “It’s just not something I ever considered... a threesome?”

“A threesome with a hot mare that wants the both of us?” Thunderlane asked with a chuckle. “Come on, you saw how cute she is. She wants us both to come!”

“Don’t get me wrong, I want to go, but...”

“But what?”

“I...” Rumble ran a hoof over his muzzle and shook his head. “I don’t want to embarrass myself… There, I said it.”

Thunderlane rubbed his jaw as he figured out what to say next. “Listen bud, I know you’re not gonna embarrass yourself. And you know how I know why? Because I got your back, that’s why.” He laid his right foreleg around Rumble’s back and pulled him close. “All you gotta do is relax and do what feels natural. And if you aren’t sure about what to do, just let her take the lead. And above all?” He paused until Rumble looked up at him. “Just have fun!”

“Jeez, I wonder what she’s got in store for us!” Thunderlane said as he and Rumble trotted side by side down the wooden bridge. It was just wide enough for two ponies to walk side by side without worrying about bumping into each other and the railings. Thunderlane closed his eyes as he imagined what was going to go down that night. Scenes of him blowing his hot load all over her back, getting his cum all over and in between her feathers… He felt himself start to grow stiff, but he bit his cheek to suppress those feelings. He was a gentlecolt after all, and showing up with a raging boner just would not work well at all.

“You nervous too?” Rumble asked hesitantly.

“...A little, yeah, but it’s gonna be fine.” Thunderlane nudged Rumble’s side with a wing, then smiled down at him as they approached the house down at the end.

Rumble slowed his pace down just a little bit, then when he was sure that Thunderlane wasn’t looking, he snuck a furtive glance at his brother’s crotch. He saw his tip starting to peek out from the opening of his sheath, so he quickly looked away. Might as well get used to seeing my brother’s cock if we’re gonna be in a threesome together...

They reached the end of the common bridge, then stepped onto a small walkway that led to Night Glider’s house. Thunderlane bit his lip as he lifted his hoof to knock on the front door, but right before he did, he noticed there was a note taped onto it at eye level. “The door is open, and I’m out back. Come right on in,” he read, his voice full of unbridled excitement.

“How do I look?” Rumble asked. He fluffed his wings and ran a hoof over his mane.

“You look good. What about me?”

“Well, aside from your half-hard cock, you look good too,” Rumble said with a chuckle.

Thunderlane blushed. “Oh, uh... yeah. Sorry about that.”

“Why are you apologizing? We’re gonna be seeing a lot of each other soon, so... yeah.” Rumble blushed.

“Hehe, I guess you’re right! Come on, let’s go see how Night Glider’s doing.” Thunderlane pushed the door open and walked inside. Rumble closed the door behind them, then walked right into him.

“Yeesh, what’s wrong, bro?” Rumble asked. He looked where his brother was looking, then his jaw opened wide. “Woah...”

Night Glider’s house was the definition of beauty. A large piece of glass sat before them in the floor, revealing the water several feet below them. They stepped right up to the edge and looked down to find a small reef, complete with a myriad number of fish.

“Woah, is that an eel?” Rumble asked as he pointed it out with a hoof. “I’ve never seen one of those before!”

“Yup, that’s an eel alright.” Thunderlane watched as it lazily swam in between a pair of fish before it disappeared out of their sight. He saw movement out of the corner of his eye, so he looked up and saw Night Glider staring out into the sunset through the far window. He nudged his brother and nodded towards her, then made his way through the rest of the house.

Pushing open the sliding glass door, his jaw dropped as he saw what Night Glider was wearing. She was in a casual white dress, and if his eyes weren’t deceiving him, she was wearing a pair of panties underneath it. It caressed her curves, accentuating all of the sexy bits. The end of the dress just barely covered her flank, leaving little to the imagination.

Her wings were folded flat on her back, preened to perfection. Her mane and tail were combed equally as nice. She was laying on a bench with a small glass of red wine in her hoof. Two torches sat on either side of the balcony, lighting her up in the most beautiful of lights.

The boys simply could not take their eyes off of her.

Thunderlane coughed gently, making her turn around. She smiled at the both of them as she placed her glass down, then let her eyes drift lower. He knew she was checking out what they had to offer, and he had absolutely no problem with that. His cock twitched and grew a little harder as he stood there.

“Evening, boys...” Night Glider purred as she stalked towards them. She placed one hoof in front of the other as she crossed the short distance between them. “I am glad to see that you both... came for me.”

“Wouldn’t miss it for the w-world, ma’am,” Rumble said with a nervous smile.

“Oh, please just call me by my name, Rumble. We’re going to get really familiar with each other, so such things aren’t needed,” Night Glider said with a light chuckle. She winked at him, then said, “Take two steps forward, if you will.” Both boys complied without a moment’s hesitation.

Night Glider walked up to Thunderlane first and laid a light kiss on his cheek, then nuzzled his neck. She pressed her breast up against his and laid her head on the back of his neck. “So strong...” she whispered. Breaking away, she walked to his side and looked down at his shaft. He was rock-hard now, standing at an impressive length that would make most mares wet from the sight. “And well-equipped, too...” She lifted a wing and ran the tips of a couple feathers on the underside of his shaft, paying special attention to his tip. Thunderlane gasped softly at that, making her smile widen.

She folded her wing and stepped around his backside, moving to Rumble. “And last but definitely not least...” Night Glider noticed that he wasn’t as hard as Thunderlane yet, so she lowered her head and lifted his tail with a wing, then kissed each of his balls. She nuzzled them and licked them until they were glistening with her saliva. She noticed that Rumble twitched and groaned with each and every lick, so she smirked and walked around his side. He was just as hard as Thunderlane now and his tip was already dripping pre-cum. “My my... aren’t you ready to go, hm?” Without waiting for an answer, Night Glider licked his tip and swallowed what little he had to offer.

Her tail hiked up just enough for the boys to see her white cotton panties underneath her short dress. She was wearing her favorite pair. They were the comfiest pair she had, and they were covered in light pink and light blue polka dots. Her outer lips were puffy, showcased perfectly in the crotch of her panties. If she wasn’t mistaken, she knew that they were already wet with her arousal, and she was certain that the boys could see that.

“Come, let us retreat into the bedroom for some... fun.”