Hesperus

by doctor dapples

Rating: mature
Tags: Romance
Length: 3471

A unicorn, frustrated from visiting his parents, reluctantly makes a talented friend (M/M)

Glasgow Smile has just had another less than heartening visit with his eccentric parents in Canterlot. After dealing with their nonsense, he would rather just be left alone to unwind with a couple of drinks. But another unicorn at the bar is about to change his entire evening. (M/M)

UPDATE (9/29/2012): Felt I should add this warning. While there is no active violence in this story, there are elements akin to date rape in this story. If you are sensitive to such topics, I would recommend avoiding this piece.

Published 1970-01-01 00:00:00 UTC
Last updated 2012-04-03 20:04:03 UTC

Chapter 1

The first shot he didn’t even drink. He just swished it around his mouth like a mouthwash, trying to cleanse every nook and cranny of his mouth. Then he spat it into the trash can. No luck. He could still taste his father’s tea.

“Dammit,”  he said with a sigh, before raising his hoof to order a second vodka, this one on the rocks.

It wasn’t as if Glasgow hated visiting his parents, persay. He certainly never had to worry about growing bored. Before he’d even said hello, Gatsby would immediately offer Glasgow a cup of Earl Grey. No matter how much of the tea he drank, he never seemed to be able to empty a cup. He wasn’t sure how his father was refilling it every time he looked away from his beverage, but even as a child he had never seen the bottom of a single teacup.

And then his mother would come in. Regal would descend from the upper flow with her long satin train following her, and her husband would bow (whether it was out of genuine reverence or a wry jab at her sanity, nopony knew). She would ask for the daily report, and then address her “subjects”. Cheshire was a little better at being ingratiating, but Glasgow had little patience for her airs and usually cut straight to the point. His brevity usually earned him an order of execution that always got stayed.

At the end of most trips, he would leave with the taste of bergamot on his lips, and a price on his head. On the rest of them, he used his special talent and vanished. Most of the times he didn’t even care where he showed up again, just as long as it wasn’t there.

From across the room, a large gray unicorn watched Glasgow nurse his second drink. His violet eyes traced the pony’s figure: his long legs, the slim body, the disheveled yet elegant fetlocks...

Yes, this one would do nicely.

Glasgow took another sip, and silently cursed Canterlot. While to some ponies it stood as a symbol of Equestria’s might, to Glasgow it was closer to a tomb. Everytime he was here, he felt trapped, cut off from the world he cared about, from Jojo. Joyful Wings, like most pegasi, couldn’t stand the oppressive nature of Glasgow’s family, and aside from a few visits early in their courtship, had always opted to stay behind. Jojo was smart that way. He took a long swig of his drink.

“Whoa, slow down there,” said the grey unicorn sidling up next to Glasgow at the bar. “The night’s young and you have plenty of time.”

Glasgow glowered at the unicorn. “Can I help you?”

“Yeah, I need help moving out of my apartment this week. You available?” The grey stallion shot Glasgow a toothy grin that was not returned.

“That’s a joke, right?”

The unicorn shrugged and held out his hoof. “The name’s Star Seams.”

Glasgow looked at the outstretched hoof as if he had just been offered a bag full of worms. He eventually accepted Star’s gesture with his own and gave it a passive, yet firm shake. “Glasgow Smile.”

“So, do you want another one of those?” asked Star, nodding at Glasgow’s nearly empty tumbler.

“I’m fine,” he grumbled, taking his last sip. He was seriously considering pulling another vanishing act.

“Don’t be silly!” Star rapped his hoof on the bar twice. “Two more over here!” he called to the bartender, who used his magic to pour both drinks without breaking his conversation with a cute mare at the other end of the bar. Star swapped out Glasgow’s empty with a little magic maneuvering of his own, earning a suspicious stare from the striped pony.

“What’s your deal, Mr. Seams?”

“Please, there’s no need to be that formal. Star works just fine. After all, you wouldn’t want me to call you Mr. Smile, would you? Especially since you don’t seem to do that much of it.”

Glasgow snorted.

“Look,” said Star, sidling up much closer to Glasgow than he would have liked. “I get it. You don’t like me. But like me or not, it’s clear there’s something on your mind that you need to get out there. And these ears are big for a reason.”

“It’s really not any of your business.”

“Of course it’s not! But you’ve got the look of somepony who needs to talk. And he’s not going to be any help.” Star gestured to the barkeep, now whispering something into the ear of the giggling mare.

Glasgow’s sneer turned into a frown. He looked around the room. The bar was filled with ponies, but each of them seemed to be chatting or laughing with somepony else. And they were all smiling. He sighed as he looked down, past the melting ice, into the bottom of his glass. Then he glanced up at Star, whose smile carried a warmth he hadn’t seen a moment ago. “Alright.”

“Woohoo!” Star cheered and clinked his glass against Glasgow’s. “Now, first of all... tell me about yourself.”

So Glasgow talked. He allowed himself to vent his frustrations with his family. From the moment he had entered his once childhood home, now dilapidated after years of neglect, he had been carrying a tension inside him, and that tension had only gotten worse as he had attempted to carry on meaningful conversations with Gatsby and Regal. But that tension began to subside with every word that left his lips, and the words flowed even more freely as time passed and more drinks were consumed.

“She’s beautiful.”

“What was that?”

“Jojo,” said Glasgow. “My mate. She’s beautiful.”

Star smiled wider than ever. “Tell me about her.”

“She’s beautiful.”

“You said that already.”

“Joyful Wings. She’s a beautiful blue pegasus with a fiery red and orange mane. Sometimes I like to chew on it. It drives her crazy.” Glasgow chuckled at the memory, and Star echoed it.

“What’s she like?”

“She’s a lot better at just having fun than me. I think she balances me out by having more faith in ponies than I tend to.”

“So what do you bring to it?” asked Star.

“Well, she’s not always very assertive, and I like to think that I encourage her to be more confident. A lot of ponies think she doesn’t care about anyone but herself, but really its just because she’s shy.”

“She sounds like a real catch.”

“She is.”

“Let me get you another drink, Glasgow. The same?”

“Let’s switch it up just a little bit. Barkeep?” He raised his hoof to signal the bartender, but no one answered. He looked up and widened his eyes, as he realized that his surroundings had completely changed. The bar was gone. The other couples were gone. And in their place was a sofa and a coffee table. “Where the hay am I?”

“You’re at my apartment.” Star appeared with a full glass in each hoof. “You walked here with me while telling me about your parents.”

Glasgow gave his head a quick shake. He didn’t remember any of that, but he was also pretty sure he hadn’t looked up since the third drink at The Lounge. “You took me home?”

“Well, they had to close sometime, and you weren’t done talking.”

Glasgow looked over at the clock and shuddered. In a few hours, Celestia would be raising the sun. “You’ve got to be kidding.”

“Hardly.” Star handed him his glass, which Glasgow looked at skeptically.

“I don’t know about this, Star.”

“Last of the night, I promise.”

Glasgow nodded towards Star’s drink. “You’re in this, too.”

“To the end.” He lifted his tumbler. “To new friends.”

Glasgow smiled and echoed the toast. “To new friends,” he said, clinking his glass against Star’s before gulping down the vodka with a grimace and a cough. Star smiled and drank down the contents of his glass: ice water.

Almost immediately, Glasgow felt his thoughts begin to swim. He struggled to remember the last thing he had told Star, but his brain refused to focus. The only word he was able to properly center on was “Jojo”, and as he said that word, his eyes rolled back into his head, and he passed out on Star’s sofa.

“And away we go,” said Star with a grin.

Glasgow’s eyes snapped open at the sound of the whistle. He gave his new surroundings a cursory glance before his eyes focused on the large window on his right. Behind it, rural Equestria passed by in a blur, beneath the grey clouds that seemed to hang ominously in one place. “Great,” he murmured. “Where am I now?”

“You're sitting on a train, a train that will take you far away.”

He turned towards the voice to find Joyful Wings standing in the doorway to the cabin. “Jojo? What are you doing here?”

Jojo continued as if she hadn’t heard the question. “You know where you hope this train will take you, but you don't know for sure. But it doesn't matter. How can it not matter to you where that train will take you?”

Glasgow sat up and trotted over to Jojo. He took her into his forelegs and begin to kiss her on the muzzle. After some hesitation, she returned the kisses, ending with a soft kiss on his lips. “I missed you, Jojo.”

“I missed you, Glasgow.”

“How did I end up here?”

“Your friend.”

“Who?”

“Star Seams.”

“Ah,” Glasgow said, nodding. He tried hard to remember the pony she was referring to, and he vaguely remembered the blue-maned unicorn, but the mental image of him remained fuzzy. “He called you?”

“First thing in the morning. He said you had been lonely after your visit, and you needed the company. When I got there, you were still out cold from drinking, so he helped me load you up onto the train.”

“And we’re going home?”

“Maybe a little more than an hour left now,” said Jojo.

“Where is he now?”

“He’s probably back at his home by now, sweetie”, she said with a smile. “I’m glad you we’re able to take this trip together.” She leaned in and kissed him on the lips, and he happily returned it.

Glasgow felt warm inside. He was always a fan of kisses, but this was one of his favorites: the “I haven’t seen you in a while, welcome home” kiss, and Jojo was even less shy today than usual. Her muzzle pressed hard against his, and as she cradled his head in her hooves, she forced her tongue past his teeth. Her breath was intoxicating.

Suddenly, Glasgow felt Jojo moving him backwards, pushing him against the bench in their compartment. “Feeling a little frisky?” he asked.

“Definitely,” she said with a seductive nicker. She nibbled at the base of his jaw.

“What are you in the mood for?” he asked with a sly smile.

“I want to rut you.”

Glasgow laughed. “Well, obviously. I’m a pretty sexy pony, but you’re going to have to be more specific than that. Where? What position?”

Jojo lifted herself off of the smug stallion, and shook her head. “You don’t understand. You ARE a sexy pony. I couldn’t get that flank of yours out of my head.” Her mouth curled up into a smile. “And that’s why I want to rut you.”

For a moment, Glasgow just stared. “What?”

Instead of answering, Jojo stretched out a wing and flicked off the lights. As Glasgow heard noises that sounded like somepony rummaging through a suitcase, he began to get more nervous. What was Jojo talking about? Rut him? How would she...

The light flicked back on, and Glasgow’s jaw dropped.

Dangling in front of him was the head of a large artificial, yet fully erect cock. Jojo had strapped on a harness of some sort and if not for the visible straps around her flank, there would have been no way to tell that she wasn’t born with it.

Glasgow gulped. “Um, Jojo...”

“This is Chance,” she said, gesturing to the dildo. “I picked him up before I came for you.” She shook her hips, causing the cock to wiggle back and forth in an unnerving manner. “What do you think?”

“Jojo, I don’t know if I...”

Jojo frowned for a moment, but quickly perked up. “I know it seems weird, but you just met him. You should take the time to get to know him.” She moved towards Glasgow, bringing the head of the cock within inches of his muzzle. “Introduce yourself. Give him a little kiss.”

Glasgow couldn’t deny his confusion, but he cared about Jojo, and while he didn’t exactly understand what had gotten into her, he wanted to make her happy. He closed his eyes, puckered his lips, and leaned forward to place a peck on the tip of the dildo.

“Now another.”

He kissed it again.

“Suck on it.”

As he opened his mouth slowly, Jojo stepped forward, pushing the first few inches into his mouth. She let out a soft sigh, and as Glasgow felt his mouth fill up with the toy, he wondered what exactly she was getting out of this. After all, it’s not as if she could actually feel the warmth of his saliva, could she?

“Use your tongue,” she said with a nicker. “And be careful with your teeth. Chance was expensive, and I would like to use him again.”

Glasgow complied and let his tongue swirl around the shaft. Jojo smiled down at him, her cheeks flushing with color. She ran her hoof through his unruly mane, and Glasgow began to feel the first indications that he was getting aroused too. Between his hind legs, the very tip of his own cock was beginning to creep out of his prepuce. As he increased the intensity of his sucking, he began to lightly graze the tip of his hoof against the emerging shaft.

Jojo smiled. “Getting a little excited, are we?” He nodded and tried to say something around the cock, but the words came out muffled. “Well, I think you’re in luck. I get the feeling you’ve got me slick enough to handle your tight little ass.”

With a light touch to his jaw, she coaxed the reluctant stallion to let the dildo slide out of his mouth. A thick drip of saliva hung on the tip, and Glasgow would have sworn it looked a little bigger than before. In his mind, he made the connection, and immediately pictured the dildo plunging into his anus. While the idea scared him, causing him to emit an audible squeak, he couldn’t help but feel aroused, and he began to speed up his own masturbation.

But Jojo pushed his hoof away. “No, you can’t get off yet. I need to know that you can handle this first.” She spun her hoof in a circle, indicating for Glasgow to turn around. He then felt a firm tug on his tail from Jojo’s mouth. He took another gulp, and lifted it.

As he felt a pair of hooves clamp onto his sides, he gave a yelp of surprise. He had mated before, but he had never really imagined what it felt like from the mare’s perspective. His mind began to race, asking himself a world of questions as to what it would feel like, but he immediately lost focus as he felt the tip push against his anus.

Glasgow grimaced. “Is it in yet?”

Jojo chuckled. “Not even the tip, Glassie. Are you that eager for it?”

“No, I - OH GODDESS” he yelled as the cock pushed its way past his entrance, slowly engulfed by his warm insides. He felt stretched to the breaking point. It burned. He took some deep breaths and steeled himself against the pain. He wanted to do this, for Jojo.

“I know it’s big. But it’ll get better soon.”

“How soon?”

“Trust me,” she said. And with that, she began to slide out. She raised her hips, pulling out all but the head, and Glasgow felt a wave of relief pour over him. She pushed back inwards, and the pain returned, but it was duller, and there was something else lurking beneath the surface, keeping his own dick hard.

He found that with every thrust, the pain dulled, and a wonderful warmth took its place. Jojo was making contact with something that was driving his body crazy, and every push sent those sensations surging through his body. Without him touching it once, his own cock was completely erect, and already a clear bubble of pre sat nestled at its tip.

While Glasgow gazed enviously at his own juices in anticipation, Jojo had whipped herself up into a frenzy. Her patient rhythms of earlier turned into hard thrusts, answered in kind by Glasgow lifting his hips into them. She craved his ass, and he craved her cock, and in the mass of sweaty pelts and pulled manes, Glasgow forgot that she was just using a toy.

Until the head of the cock flared. Glasgow’s eyes shut tight as he felt the crown expand inside his ass. He knew what was next, even if he didn’t know how it was possible. The toy jerked inside of him, and a sudden surge of warmth signaled to the stallion that Glasgow was cumming. He grinded himself into her, milking her for every last drop, but soon the girth of the organ against his insides were too much.

With a shudder and a moan that he could feel all the way into his ballsack, Glasgow came. A thick stream of semen fired out of his cock, and landed between his front hooves in a white splatter. His cock pulsed again and again, each time spilling a little more seed, until the last of his cum oozed out of the tip, and Glasgow fell to the floor of the cabin exhausted, and not even caring about the mess.

Jojo, still on the stallion’s back, leaned over and nipped at his ear. He gave a weak laugh, unable to do much in the way of retaliation. “You make a very good mare,” she said with a smile.

“You do pretty well as a stallion yourself,” said Glasgow. He exhaled a sigh of contentment, and felt his eyes start to get heavy from exhaustion. The last thing he felt before he passed out, was the peck on the cheek. The last thing he heard was “Thank you, Glasgow.”

Glasgow’s eyes snapped open at the sound of the whistle. He gave his new surroundings a cursory glance before his eyes focused on the large window on his right. Behind it, rural Equestria passed by in a blur, beneath the grey clouds that seemed to hang ominously in one place. “Great,” he murmured. “Where am I now?”

He thought for a moment. “And why does this all seem familiar?”

“You’re on the train to Ponyville, sir.” Glasgow looked up to see a cream-colored Earth pony wearing a conductor’s cap. “Could I see your ticket please?”

Without thinking, Glasgow reached into his saddlebag and pulled out the small orange stub. He handed it to the conductor, who looked at it for a second, then nodded. “Thank you very much, Mr. Glasgow! Have a pleasant trip!”

As he turned to leave for the next cabin, Glasgow stopped him. “Wait! How did I get here?”

The conductor gave him a confused look. “You really don’t remember?”

“Remember what?”

“Wow,” he said with a chuckle. “You really had tied one on. Your friend brought you here.”

“My friend?”

“A unicorn with a blue mane. He paid for your ticket and everything. Said that you’d never get back to your mate if he let your drunk flank try to figure it out on your own.” He began to chuckle, but when Glasgow’s expression didn’t change, he stopped and gave an awkward cough. “Uh, no offense, sir.”

Glasgow just stared.

“Well,” said the conductor nervously, as he began to back out of the cabin. “I’d better get to the other passengers. We should be in Ponyville shortly! Hope you enjoy the rest of your trip!” And with a quick burst of speed, he was gone.

Glasgow blinked, shook his head, and looked out the window at the passing landscape. He felt like he was losing his mind, but aside from a slight soreness in his flank, he felt fine.

“Maybe I’m just still tired,” he mused, allowing himself to be hypnotized by the trees that sped by just feet away from his cabin. His eyelids grew heavy, and soon he slipped into a dreamless sleep.

People say that your dreams are the only things that save ya... Come on baby in our dreams, we can live our misbehaviors