Chapter 1: Discrete Liason

Shining Armor finished masturbating, feeling spikes of pleasure emanate from his cock as he jerked it while jizz spilled from the tip. He focused his eyes on the image on the computer, a busty mare milking a cock with her breasts. Shining could only imagine how great that must feel for real. He didn’t know how the stallion in the film didn’t pass out roaring in pleasure, cumming the moment those luscious breasts touched his shaft. And when the mare had added her touch and mouth to it, it looked like it must have been heaven for that stallion. Lucky guy.

Shining closed several incognito tabs on his computer and wiped himself off on his sheets. It hadn’t been a particularly good wank. He sighed discontentedly, still feeling the lust within himself. He remembered back when he was in his earlier teen days, when everything sexual was new and exciting, when he got rock hard erections on a whim, when every new orgasm was his best ever, and just the thought of a mare in a revealing outfit was enough to send his hormones racing. He’d been once almost giddy with excitement to get home from school so he could spend some quality alone time with his thoughts, or a clandestine picture. And then a magazine. And then he’d discovered what was available online… what a revolution in boyhood sexual evolution! Every kind of mare doing every kind of thing. So many, seemingly infinite. He’d quickly figured out what was and wasn’t for him. He’d spend hours stroking gently, just soaking in everything there was. Over time, he developed favorites, learning sites, tags, and stars, and that had been enough for them. His adolescence had passed and now he was just a week out of high school; he was eighteen, ready to take on the world, and hadn’t gotten past awkwardly kissing a few fillies a few times. He had signed up for the Royal Guard and was going off to training by the end of summer. So there he was, just waiting for his recruiter to get back to him with a full list of potential ship dates.

His hormones were demanding action. Nay, his pride, too. Was he really going to join the military as a boy who’d never even felt a boob? What if something happened to him before he ever got the chance? After all, tensions with Griffiya were looking up and the possibility of being deployed was looking more and more likely by the day. All in all, he simply had to find a way to sate his curiosity and his lust, soon.

He thought back to the moment that had sent him on his was to this particular sojourn to pornland. He had just come back from his jog, stumbling in the door, all hot and sweaty, grateful for the cool of the air conditioning in the late July heat, when he crossed paths with his mother in the kitchen, wearing her standby barely clothes summer attire. The smell of lavender mixed with sweat... Nonono, that couldn’t be right; the day had been hot, meaning plenty of pretty ladies going about in their sexy summer clothes. Indeed, he remembered now, it had been a veritable carnival of feminine flesh very much like a jewelry store in that he could look but not touch, and all of the samples on display seemed hopelessly out of reach for a young stallion like him. He had to be sure to not get caught staring at bouncing bosoms, bobbing butts, lithe legs, and that most appealing sound of mares breathing heavily in the heat. Twice he had nearly run into traffic, and once almost careened headlong into a telephone pole. He couldn’t tell if he’d had an erection; if he had been sporting wood, his running shorts wouldn’t’ve done much of a job of hiding it.

He had even caught a glimpse of the glorious Cadance jogging through the park, and he’d made sure to overtake her only very slowly so he could feast his eyes on her royal fineness. Oh how he wished he could have a mare like that for his own. Of course he couldn’t; she was a princess and was, well, him, so not even in a million years. Besides, she’d been finishing up school just as he had been getting started, so she already had years on him, and being a princess, plenty of inches on him, too. She must have been courted by every single upper crust guy in Canterlot and many from all over Equestria, so as a woman on the world, what use would she have for a plebian boy like him when she had a true buffet of distinguished men at her feet? Sure, they’d talked a bit around Twiley’s foatsitting sessions, but that ironically made it worse, for now he was a friend, and not even all of Luna’s forces and Celestia’s might could rescue anyone from the friendzone.

He thought about Cadance. Oh how he liked her very much. And she seemed to like him, too. And how painful experiences with fillies at school had taught him that was the kiss of death! And there came that dissatisfaction in his loins again. The world looked like an orgy and here he was not getting his share! It wasn’t fair, damnit!

And then he’d finished his run home, stumbled through the front door, took his shoes off, glanced at his mother, and then sauntered upstairs for some relief. And now he was here, less sweaty, but just as in need of release. None of his friends were around; they were all at jobs, or traveling, or internships, or some thing or other for the next two weeks. So here he was, stuck all alone in his house with nothing to do but suffer through his horniness and boredom all alone.

Shining was about to go boot up a game when he realized there was one last tab open in his browser. It was an ad page with a picture of a busty, mature pegasus mare with outstretched wings and the text “Tired of clopping? Click here.”

Bored enough to comply, he did. The link took him to a page called Whorses.clop. The first thing he saw was one of those age verification pages which didn’t actually ever stop a single pony from gaining access. He clicked his way through, feeling a small sense of happiness that he was old enough to finally answer those things honestly. Next, Shining was faced with a map of Equestria with a bunch of dots labeled with city names. He clicked on Canterlot and immediately got a menu of things to choose from. Mares for stallions, stallions for stallions, mares for mares, gentlemen for mares, transsexuals, pseudoalicorns, interspecies! Not feeling like a pervert, Shining chose the first option and was immediately greeted by a gallery of differently seductively-posed mares of differing tribes, colors, and ages. His brain fizzled slightly when he saw just how many unicorns there were on the site. So much for unicorn mares having the sense to not appear in such disreputable places. Could he perhaps… was this for real... all these mares… and he… for sale? His dick stirred.

There was a drop-down menu containing various tags. Unicorn, Pegasus, Earth, Canterlot, Trottingham, Prench, Model, BDSM, Estrus, Mature, Bloodhorse, Chestnut, Clumper, Cob, Dam, Piebald, Solid. He clicked on dam, immediately being greeted with mature mares. His shaft continued to harden, and so he stroked himself as he browsed down the gallery. This was what he wanted; no more skinny, immature fillies at school who whined daddy on their phones while begging to be allowed to go to parties; here were proper mares with their graceful sexuality and undeniable muliebriety. Shining Armor scanned down until he found a particular ad.

He didn’t know why he clicked it, only that the mare in the photographs was a curvy silver mare, a unicorn, with a flowing pink and yellow mane which cascaded long down her shoulder, a strand lying teasingly between her large breasts. He read the profile.

Hello, my name is Eventide Velour. I am a refined older mare looking for a good gentlecolt to keep me company. I know and appreciate the finer things in life; wine, food, song, and more. And just as much as I like to receive, I also like to give in return. If you are tired of selfish sluts, a tryst with me is just what you need. I am a truly elite companion with graces for every occasion from a royal reception to a sultry weekend alone. They say that the blood of Princess Platinum runs in my veins, and I would love to give you a true royal treatment. Let me be good to you. Let me pamper you and take care of you as only a lady can. If you have only heard the term courtesan, get in touch with me, let me show you the magic of a true mistress of the intimate arts and a pleasure only a select few ever get to experience, either at my incall or whatever upscale location you have in mind.

I’ll be waiting,

-Lovely Eventide Velour

Hours
Friday-Sunday, 11AM-Midnight. Weekdays by special request.

Please be on time; ideally arrive 10-15 minutes prior to your appointment, dressed nicely, showered, and with your teeth brushed. Please book no fewer than 36 hours in advance. If you cancel within 24hrs of appointment, you will be charged 25% of your booking which you will have to pay before our next date; no exceptions! Outcalls receive a surcharge plus my transportation costs. For bookings longer than four hours, a non-refundable 15% deposit is required and must be booked at least 7 days in advance. I do travel with a daily surcharge and a least two weeks prior notice including an itinerary.

Experiences

1hr incall: 100
1hr outcall: 200
1.5hr incall: 150
1.5hr outcall: 275
2hrs incall: 200
2hrs outcall: 350
3hrs incall: 300
3hrs outcall: 415
4hrs incall: 400
4hrs outcall: 500
Each additional hour: 50
All night: 1000
All weekend: 1800
Week: 5000

These donations are for my time and companionship only. They do not indicate consent to any act, sexual or otherwise. They are non-negotiable and to be paid with an envelope containing the full agreed amount at the start of our date. If payment is short, regardless of the scheduled length of our date, you shall only receive the amount of time you have paid for. I accept cash only.

To schedule a date, either email or text me. No temp emails, voice calls, or private numbers. These will be ignored. Do not ask for pictures. Do not discuss services or prices in communiques. Until an appointment is set, we discuss time only. Do not ask about sex acts. Serious suitors only.

I await your pleasure.

The ad ended with a phone number and an email address. Shining hesitated for a long while. Did he really want to do this? He wasn’t exactly rich, but he had some money from an allowance as well as working a few small jobs. He didn’t have any real expenses and there wasn’t anything he wanted to spend money on, other than firearms and military gear, which his mother absolutely prohibited, telling him that if he wanted them so much, he could join the Royal Guard for real instead of playing make-believe soldier at home like a colt.

What the hay, why not? It wasn’t like his immediate future was swimming with chances for him to get what he was after? And besides, his parents had given him a fat check as a graduation present; he could not work a day this summer, spend more lavishly than he usually did, and still come ahead from if he’d been thrifty and industrious. He browsed the rates, trying to do a bit of mental math to figure out the best deal. He knew outcall to his place was out of the question – he couldn’t even imagine trying to explain to his parents and sister when a hooker showed up at their door asking for him! So incall it was. He knew intuitively that the best per hour deal would come from a longer booking, but he couldn’t afford a truly long one, or get away with spending that much, not that he even had that kind of wealth. And there would doubtlessly be things he’d want to buy sooner rather than later, too. After a rough bit of number crunching, he’d reckoned a week was roughly 700 bits a day, or a hair under 30 an hour, a far cry from the flat 100 an hour for shorter sessions. A rumble in his stomach; time for lunch.

Shining Armor composed a text on his phone. “Salutations, Madam Velour. I was wondering if I could perhaps engage your services at incall this weekend? Please text me back at your first convenience.” And with that, sending the text away, his heart fluttered with the shameful rush of doing something that felt dirty and perhaps more than a little naughty. He decided that, while he waited for her reply, which he bet would not be for hours, he’d get something to eat. And so the naughty colt went downstairs.

Downstairs, Shining was greeted by his mother cooking dinner in the kitchen. The fragrances of mushrooms, pepper, beets, carrots, and tomatoes filled the air along with the babbling bubbling of a boiling pot. “Hi, Mom,” he greeted.

“Hey, Shiny, what’s going on?” She wasn’t wearing much, just a tank top and a pair of denim shorts. She was a pedestrian, middle class mare, unlike Madam Eventide Velour, though she had a clipped Canterlot accent.

“Just hungry, Mom,” he replied.

“Well, you’ll have to fix yourself something; I’m busy here.”

He winked at her. “C’mon, Mom, I’m your firstborn; you can’t starve me.”

“Well, what do you want me to do? Make you a sandwich?”

“Yes please,” smiled back Shining as a ding went off that could have been any number of things in the chaotic kitchen.

“Sorry, I can’t; I’m cooking and need all the space and ingredients we have. You’ll have to get something yourself or wait until dinner.”

“When’s dinner?”

“In an hour.”

“But I’m starving,” he whined melodramatically. “I’ll die if you don’t make me something, Mom.”

“Fine,” Twilight Velvet fake groaned, “One sandwich for my little prince.”

“Yay!” Shining cheered. His mom gathered bread and toppers from the fridge and then pulled out her phone and started texting in between some step of the cooking process or other. “By the way, Mom, is dad coming back on Thursday?” This was their game; it wasn’t unusual for Shining to play beg his mom for snacks, and she’d put on a token show of irritated resistance, grumbling all about how there wasn’t time, space, or food to do that, and then produce something opulent to be called a meal in some other households. To be honest, at some times, it was the only thing that kept the days the least bit interesting.

The older mare shrugged. “Sadly not; the company’s project is going overtime and they need him there now more than ever.” Her shoulders sagged.

“Isn’t that what they always say?”

“He swears they mean it this time.”

Shining quipped, “Don’t they always?”

“Can’t talk; cooking,” hummed Velvet. To her, having her son hanging around bugging her was a welcome nuisance, since with her husband away on one of his frequent long business trips, and Twilight being a hermit bookhorse, he was the only one who would keep her company and his unending shouts for her cooking reminded her that she was loved and needed by her family, even if she didn’t get to see too much of them oftener than she would have liked. She didn’t work, but she always seemed to have something to go to more or less every weekend. And as she did this, she texted away on her phone.

Shining was seated at the table when his phone went off. There was a new message, fresh back from Eventide Velour’s number! He read it silently. “My good gentlecolt, I am available this Saturday at 4, 7, 8:30 all the way to 11. Sunday has 1:30, 2, & 6:30.”

Shining texted back, “Cool.” A ding he ignored out of habit. The reply came a couple minutes later.

“Cool isn’t a time, Sir.”

Shining flushed. Only he could have been a dork in a text to someone whom he didn’t even need to impress. “Sorry. A bit nervous. :)” Ding.

“No need to be. May I recommend the ninety minutes so we may get to know each other?”

This mare was texting back quickly. The colt was too engaged now to back down, the excitement of knowing there was a potential mate on the other end inspiring him to keep going to see where he ended up. “Sure.” He tried to think of a date and time. There wasn’t any real difference between Saturday and Sunday, but he wanted it soon for fear that he would lose his nerve and chicken out of the whole thing. Ding. As far as hours went, none held any real advantages, although he could conceivably sleep through the earlier appointments and he wouldn’t want his mom and sister getting too worried if he was out too late.

“Your choice, Baby.”

“I would like a date at 9P.M. on Saturday, please.” Ding.

“Certainly, Sir. I will be a pleasure to have you.”

“Same.” Well, now he’d done it, no backing out now. Ding.

“What is your name?”

Shining paused for a moment, scrambling to come up with a name. Then he remembered the one on his fake ID, not that he’d ever used it; he’d just gotten it for the hell of it. He typed out, “Gleaming Shield.” Ding.

“Well, Mr. Shield, see you soon.”

“You too, Madam Velour.” He sent it. Now he’d really done it; no backing out now. He didn’t know if he felt more nervous or excited. Ding.

Shining was woken from his reverie by his mother leaning over to give him his sandwich on a plate, giving him at eyeful of her plentiful chest accentuated all the more by how it hung right in front of his eyes. A deep part of him approved more than he wished to even acknowledge. “For you, my darling prince,” Velvet presented, kissing him right by the base of his horn.

“Gross, Mom,” he fake gagged before digging into his sandwich, which was a thick stack of tomatoes, cucumbers, oats, lettuce, and pickles put between two toasted slices of rye bread. “And what’s with this grainy stuff? Don’t you know growing colts can only take the purest of white bread with the crust removed?”

“Growing colts who are about to join the Royal Guard can do grocery shopping if they want something.”

“Nothing to drink?” Before he could react, a glass of water was on the table. Shining let her win this round; any more whinging and he’d be crossing the boundary from ribbing to actually being unfair to his old mare. Shining relished the exquisite sandwich, eating it quickly. He couldn’t tell his mom just how amazing her cooking was or how much he loved her; stallions weren’t supposed to be mushy like that. They had to be cool. And so, when he finished his lovingly make snack, he waited for her to be at another section of the kitchen before loading it in the dishwasher himself. “Thanks, Mom,” he said.

“You’re welcome, Shiny.”

The wait for his date was nerve-wracking. Shining didn’t know why, but it was. The next few days passed in a slow blur. He broke the anticipation and monotony by masturbating and going on runs, and sometimes he even checked not just the ad of the mare he’d booked, but also looked up relevant laws. Equestria had no laws against voluntary prostitution by adults, but it did demand that all prostitutes have a valid paramour license, as well as always use condoms for all penetrative acts for more than a century now. Clients were obligated to treat a trick like any other mutual bilateral business transaction as well as to respect a prostitute’s consent. The old joke asked if raping a prostitute was rape or theft. The law answered that it was both. And to his surprise, there were no laws about escorting, either for clients or providers, other than it was a legally recognized profession. Apparently, the difference between prostitutes and escorts was that the former charged for acts and the latter charged for time. Now, it was somehow illegal for an escort to prostitute, but not for a prostitute to escort. He had to shrug his shoulders at that law, though it did probably explain why Velour’s ad had been so strict about communications.

He hung out with some friends on Friday afternoon. He didn’t inform them of his plans to visit a mare of the evening, but the topic of mares did come up. “Shine, I’m telling you, if any of us is getting a mare soon, it’s me,” Fletched Arrow boasted.

“And what makes you think that?” Shining prodded.

The sienna pegasus stretched his wings proudly, “Because word around the flock has it that Derpy Hooves’s parents are looking for a nestmate for her-”

“So what,” the third friend, Sprocket Spring interjected. “That’s like the pegasus equivalent of roomies. You’re getting friendzoned and set up by her parents, so uncool.”

“Shut up, mud pony,” Fletched teased. “I’m telling you guys this, because, in case you haven’t noticed, pegasi aren’t the most common types in Canterlot. There are the Wonderbolts, tourists, and then like a handful of us, mostly on weather or in the guard; you don’t need me to tell you this is a unicorn town.”

“Horny master race,” proclaimed Shining, saluting comically high into the sky.

“Let me finish,” insisted Fletched. “As I was saying, in pegasus culture, when a mare comes of age to move out on her own, her parents find her a nestmate. Nestmates are chosen by her parents from the coming of age sons of families they know-”

The other two interrupted, “You’re getting married? So young!? Don’t throw your life away – you still haven’t done anything you’ll regret yet.”

“Shut up, Sprocket, your kind doesn’t even marry! Anyway!” Fletched shouted, flaring his wings agitatedly. “It’s not like a marriage; it’s like a training wheels marriage, sorta. It’s so young pegasi can learn how to live in the adult world with somepony else to watch their back and help out. And usually, when a nestmate is chosen, all the of age sisters on the mare’s side and of age brothers on the stallion’s side get put together into one arrangement matched in birth order as best as possible.”

“Great, you all get to have awkward breakfast together after hearing each other go at it all night long. So, anyway, featherbrain, what makes you think you’re going to get Derpy?”

The pegasus grinned slyly. “Because it’s considered bad luck for stallions to outnumber mares in a nest. The numbers can be equal. There can be only a few more mares. There can be a lot more mares. But there can only be a maximum of one stallion per mare. Derpy is all alone and up for nesting. I’m an only child. There aren’t exactly a lot of other options…”

“Given that pegasi breed like pidgeons,” Sprocket snarked.

“Yeah, you talk with your four plus mares to a stallion herds with more foals than teeth.”

Shining laughed, “Both of you sex-crazed animals, overindulging your lust with harems.”

“Sucks to be you,” fired back Fletcher.

“Unicorns are unlucky enough to have a gender ratio that supports monogamy.”

Shining chuckled, “Better than our parents setting us up.”

“At least we get matched by ponies we know instead of some fat bureaucrat,” said Fletcher.

“No wonder you guys have population issues; you can’t even come together and get busy without somepony having to tell you to do it,” the yellow earth pony remarked. “At least we earth ponies get together and get busy. I know unicorn marriage isn’t considered complete until the bride gets pregnant, but you don’t even need to have sex with nestmates.”

“Yeah yeah whatever, mister expert,” rattled Fletched. “Anyway, any foals that result from nestmates breeding get taken care of by the mare’s parents if they’re fillies, and by the stallion’s parents if they’re colts. The partnership lasts three years and automatically dissolves if the mare hasn’t at least gotten pregnant once. If the nestmates don’t even have sex, the whole thing get annulled and they have to do the thing all over again with different ponies. If they’ve had foals together, they get a choice.” He winks. “Most of the time, nestmates have foals together, even if they don’t ultimately stay together. So it’s not like roomies, Spring.”

“That still doesn’t answer our question,” states Shining.

“I’m getting to it; calm your tits. I think I’m going to get Derpy, because we’re both solo eligibles, her family knows my family, and our fathers are thinking of going into business together.”

“Congrats,” the two other friends say together.

“It’s a shame I’m not a few years older; I could have been nestmated with Spitfire.”

“Bro,” Shining says, “I don’t know how anypony would get with Spitfire without being a Hurricanian like her. Blood like that doesn’t just mingle with any old seed.

“I know. So, Hero, you got your eye on any mares?” Shining had to remind himself to keep quiet about his upcoming tryst. “Come on, you can tell us. I don’t bite too hard and that toothless mule can’t bite at all.”

“Well,” Shining muttered, “there’s Cadance…”

“Man, you’ve had the longest crush on her,” Sprocket said. “Take it from me, no good comes from pining after just one mare when there’s a nation of forty-five million or so of them. I bet at least a thousand-”

“Maybe more like one hundred,” Fletched interjected.

“Regardless, there are plenty more clovers in the meadow.” The earth pony stretched his neck.

“And I should take your word for it why?”

“Because I’m the only one of us who’s been with a mare.”

“No denying that,” agreed Fletched Arrow.

Spring continued, “While you featherbrains and pinheads are busy trying to get official authorization to shack up before you even start knowing each other, we earth ponies have a simply way of figuring it all out. If you think the other pony’s a fine piece of ass, you tell them, and if they like you back, you get down to business, then you meet the herd. If they like the newbie, then you’re all set. If not, that’s just the way things are; everything gets settled there and then with no lawyers, rituals, or politics. That’s what makes our herds so awesome. If anypony isn’t working out, they can come and go at will. If we have a mare or two who just can’t gel well, we can always send them on to the next herd and get somepony else to take their spot.”

Fletched sighed, “Spring, remind me to never ask you lazy, selfish bastards for any kind of relationship help.”

“As if I’d give it to you.”

Shining laughed, “Well, come on, Sprocket Spring, who’re you looking at?”

“Me?” The earth pony seemed completely nonplussed. “Well, Cheerilee and I like each other. She said she’d show me her maids next week. Aloe, Lotus, Vera, and I are thinking we may just form a herd with me and Birch Bucket being the stallions.”

“Lucky you,” congratulated Fletched.

“Aren’t they related?” Shining asked.

“Nah, they just all have accents.”

“Think it’s gonna be a serious thing?”

“Nope, Hero. They aren’t Apple family mares, so no worry about having to sign my soul on the dotted line. By the way, you thinking about marriage yet?”

“Trying not to.”

“That’s the spirit,” the earth pony smiled.

“It’s not like there aren’t plenty of matches for me here, but I’m going into the guard soon and I have no experience with mares. And because my dad’s always away for something or other, I can’t really go with my family to a matchmaker. In short, I’ve been condemned to freedom.”

Fletched remarked, “You sure are doing your best to stop being free as quickly as possible.”

“Shut up,” grinned Shining. “I’m just worried that if I don’t die in the guard, that I’ll be too old yet inexperienced for a mare by the time I get out.”

“Don’t worry, Shining,” said Spring. “Unicorns are supposed to be virgins. That’s why they’re such great wizards.”

Shining drew a deep breath, admitting, “I’d at least like to know what mares are like before I go off to serve.”

“Not a bad goal, man. Lemme tell you, if pussy got hyped even one percent as good as it really is, every ad in the country would be selling nothing but pussy.”

“For the love of Celestia, Sprocket, don’t go corrupting the poor guy. What if his mother or Cadance learned their dear Shiny was turning naughty?” The pegasus appreciated the minor redness appearing on the unicorn’s cheeks.

“Ooh, I bet his mom would say finally and Cadance would just swoon into the arms of our muscular, delivishly handsome hero.”

“And what would little Twiley say?”

“She’d probably want to watch,” teased Sprocket.

“That’s enough, guys!” Shining growled with real annoyance this time, though he did have to admit that Twilight Sparkle would probably be enough of an inappropriate nerd to somehow find a way to take an academic interest in his carnal adventures, probably reading a massive reference tome while jotting down notes,

Fletched Arrow yawned, “Anyway, guys, it’s been real, but I’ve got to get home before my falcon starts hunting her majesty’s park animals again. Later.”

“Later,” echoed Shining.

“Later,” affirmed Spring. “Get some, Shining.” And like that, Shining Armor was starkly reminded of his situation again.

On the day of his liaison, Shining Armor had planned that he would wear nice clothes to his date instead of his usual t-shirt and cammies. The only obstacle in the way was his mother, whom would definitely see something amiss if he just walked out of his room dressed unusually nicely. He had the address now and had used the internet to figure out how he was going to get there. It wasn’t too far to walk. It was a little bit of a trek and mostly uphill, but it would only be a few miles, where there would be an upscale hotel waiting with a beautiful mare waiting for him. He was in shape; conditioning to go into the guard hard turned him from a slightly flabby guy four years ago into a toned young man. He wasn’t ripped, he wasn’t swole, he didn’t even look that strong, just toned. As he preened that evening in the mirror, he had to admit to himself that he was actually pretty nice looking. He wasn’t good looking enough to be approached by mares, but he doubted any mare would take special pains to avoid looking at him. He stood there in front of the bathroom mirror clad in a button-down shirt with khaki pants.

All the preparations had been made. He had discretely acquired some condoms in his size, he had withdrawn the 150 for Madam Eventide Velour as well as put it into an envelope he had swiped from the desk in the living room everyone in the family used for all their stationery needs. He had made sure to showed very well, using soap, shampoo, and conditioner, then getting himself with a hint of body spray. At long last, on his dry run there, he had discovered a florist shop and had factored in time to grab a solid dozen red roses. And finally, to cap it all off, he’d gotten the genius idea of hiring a locker by the park to store the money and condoms in so his family couldn’t spot it and ask questions. This was the perfect time to go. His mom was downstairs, but had hinted she wouldn’t be around to cook dinner that night, Twiley was studying with Moondancer at the castle, and his father would be out of town until some vague point in the future. All clear, unless he ran right into somepony. But who? Cadance? She had never shown on any of his dry runs. His mother? Fat chance. His friends? They’d be busy either at their jobs or pursuing good times of their own. The moon was bright and the tide was right.

He waited, passing time on his computer in that very unrelaxing way of relaxing, forcing himself to browse the web while he waited for the telltale signs of his mother leaving. Once she was gone, he’d give her a twenty minute head start before he set out just to be sure she didn’t come back for anything or see him. It would take about an hour to reach his destination, fifteen minutes each mile.

Finally, words came up the stairs. “Shiny, I’m leaving. See you tomorrow. I love you.”

“Seeya, Mom,” he answered back. Then he waited for several extremely long seconds until he heard the front door wham shut heavily like it always did. He spent the next twenty minutes excited but nervous as hell, listening keenly for any sign of anypony’s presence. When the time did pass, he breathed deeply, exhaling, “Mission is a go.”

Shining Armor stroke forth from the house, locking it behind him. He strode briskly along his meticulously memorized route. He stopped by his locker to grab the condoms and money, stowing in his pockets. He stopped by the florist to quickly grab his ordered dozen red roses. He was now set to rock and roll.

The hike wasn’t that hard, but he did sweat a bit and his heart did hammer more. Months of exercising to prepare for his shipping off to boot camp had paid off, and he made progress at a rate many other ponies would have gawked at had they been following. He made sure to avoid the heavy traffic streets, as not only would they more likely have someone on them who would recognize him, but there was a higher chance of his whole setup being ruined by someone crashing into him or pickpocketing him. And so he made his march along a deliberately chosen progression of side streets, alleyways, and service roads. He had to admit that not being in the crowd and by the traffic definitely made his progress not only quicker but also more pleasant.

The third mile was the hardest due to having the steepest slope that simply did not let up. It was also at this point that it began to rain. First it was a slight drizzle, but a few minutes later, it soon began to rapidly intensify from a near mist into a pitter-pattering spritz into drip drops of water into full on big Canterlot mountain raindrops. Canterlot had Equestria’s second best weather control, but their ability to corral one hundred percent of the mountain weather would never quite be complete due to the capriciousness of the mountain, the rain shadow effect, and also the simple fact that there simply were not enough pegasi in the city to form a large continuous weather force. In order to keep things working, sacrifices had to be made, and less weather control on weekends after dark was one of those. After all, an angry weather team could very quickly make one wish that they didn’t even have weather control at all. The rain failed to dampen Shining’s spirits, however, he was going to get LAID! There was that marvelous, heady feel like a slight tightness in his chest coupled with a bit of heat in his lungs and his groin. He could swear that his balls were warmer, slightly swollen and tingly. It was the same excitement he’d known as a boy when he did something fun but against the rules – something he’d enjoy doing but didn’t want to be caught at, like sneaking cookies or climbing buildings. When he’d got older, this was the feeling he’d come to associate with sneaking peeks and masturbating. Recently, he’d come to associate it with scoring some discrete liquor. Now, there was a new thing to associate with it: the knowledge that he would soon experience the height of mortal pleasure.

Then, like a looming giant, there stood the Shemareaton. He stood still for a few seconds. The rain was abating due to a few pegasi taking a personal opportunity to foist that bit of dampness of on somepony else. He walked along the loop and then stepped into the lobby through the big automatic doors.

The interior was well decorated yet understated despite the obvious air of class and low luxury it projected. He took a seat in a chair off to the side and texted Eventide Velour. “My lady, I have arrived in the lobby. I await your instructions.”

Not even thirty seconds later, he got a reply. “Sir, come inside room 762. Knock four times.”

The stallion turned off his phone to ensure no distractions later. He pocketed it, taking one last opportunity to check for his condoms and money. All clear. And so he went to the elevators and got a lift to the seventh heaven.

To say that the colt was nervous as hell would be the greatest use of litotes in the history of understatement. Not even the knowledge that he would one day soon be shark attacked by a swarm of screaming drill sergeants was quite as fearful as this. He could stop. He could go back, if he really wanted to, but he didn’t. His mind was made up. Half a million scenarios chased each other around his head. She wasn’t there, it was the cops busting him for some crime, he was really just going to be robbed, someone he knew would be there, he wouldn’t be able to do it well, he’d panic, the hotel would catch fire, he’d have a heart attack, she’d blackmail him. All these and even wilder ideas plagued him as he stepped off the elevator and made the fateful march to room 762, where he will knock four times at the end of time of boyhood.

Before he even knew where he was, he found himself staring at the brass numbers 762. He forcibly calmed himself, though he could feel himself shaking with some unknown anxious anticipation. He raised his fist and knocked four times. Rap! Rap! Rap! Rap!

“Coming!” a mare’s voice sounded from inside. She had a mustangian twang. Seconds later, the door was thrown wide open and a mare just like the one he’d seen in the photographs on the ad. And if he thought she was stunning in photos, she was nearly overwhelming in person. He now knew what beauty looked like.

The mare stood sevel inches shorter than he did, but her undeniable presence and personality projected to make her feel like a giantess. Her silvery fur shone. Her aqua eyes fixed him with most friendly, mischievous gaze he had ever seen. Her breasts were indeed large, so large that two handfuls would struggle to contain just one of them. He wouldn’t be surprised if she wasn’t wearing a bra due to how they sat up high and perky on her chest, and if she were wearing one, wow… Her waist indeed came out to an hourglass figure. She wasn’t exactly super thin, but he could not deny her body was juicy. Her hips flared out under the skimpy nightie and black panties she wore. Her face was kind, a tad plain, actually, but kind. And her mane of hair was simply gorgeous, being glossy, vibrantly bright pink and yellow. If she was really a dam, her body definitely didn’t betray it. She was damn good loocking, but not enough to be obvious in a crowd.

While Shining was trying and failing to take in all this beauty, the door had been shut behind him, and the next thing he knew, she was hugging him. “Gleaming Shield, so great to see you!” She had a twangy, Mustangian accent. Heat suffused his cheeks as he realized she very well could be wearing nothing underneath, and that her soft body pressing against him.

“It’s uh, nice to uh, see you, too,” he stammered.

He felt himself stirring down below. The mare rubbed up against him and whispered, “I can feel you're just excited as I am.” Shining’s cheeks nearly ignited. Breaking out of the hug, he pulled out the envelope of cash and handed it to her as well as produced his fake ID just to confirm who he was. “Thank you kindly,” Eventide Velour smiled, taking both of them. “Now, into the shower. I want you all clean before our dirty fun.” And with that she smacked his ass, herding him into the bathroom, closing the door behind himself. Shining Armor stripped naked and took a quick shower, almost overwhelmed by the reality of everything happening. He dried himself off quickly, not wanting to short himself of his session. There was a robe thoughtfully hanging from the knob of the door. He got the message and put it on before returning to the main room.

For a slightly upmarket hotel room, this was fairly standard. What was not standard, however, was the gorgeous mare looking at him while posed seductively atop the far bed in a nightie and what the colt now realized was the bottom half of a lacey black lingerie set. Shining Armor had absolutely no experience with such things, but that was about to change. He approached eagerly yet cautiously. He didn’t know what to do at all whatsoever.

Luckily, Eventide must have spotted his unease, as if she couldn’t, and patted the bed. “Come, Gleaming.” She drew herself up into a sitting position and put an arm around the poor male as he sat down. “First time doing this?”

He couldn’t quite look her in the eye. “Y-yeah…” He wished he could have said any hundred other more manly things than that.

“There’s a first time for everything, y’know,” she smiled, leaning backwards, taking him deeper into the bed with her. He felt his robe part, and he knew his private part was exposed from a certain angle, not that he had time to be embarrassed. This lady’s warm embrace was beckoning him. It took him all his courage to return her touch with his right hand. Gently, he grasped her arm. They were now both lying propped up on the pillows face to face. She entwined he fingers around his wrist and moved his hand down, saying, “Come on, touch me,” as she brushed his hand along the curve of her side, bringing it to a rest on her hip.

Her body was warm and inviting. Shining could not deny that he wanted her. He felt himself stiffen. He smelled lavender and just a few hints of sweat. That was going to change before too long. He lifted up a hand towards her chest. "May I?"

She let out a pleased noise and pulled it to her bosom. He grasped soft, feminine flesh. How arousing. This was something. Something very nice. "Ohhhhhhhh..." he sighed in innocent awe.

"Do you like them?"

"Yes, ma'am."

She laughed. "How about I let you get better acquainted?" And with that, the mare sat up to pull off her shirt. She was wearing no bra! Her gorgeous breasts were sitting high up on her chest and yet slightly parted invitingly, just like those mares in those videos! Shining Armor helped himself. He was hard now, and nature was taking its course with him. This mare... oh, this mare! Sexy and mature. He dug in with his hands. He watched mesmerized as he groped and fondled the mare. He touched her nipples, eliciting an aroused groan. He took that as a sign to go harder still. He sunk his fingers in as far as they would go into the plush mounds. He squeezed as hard as he could, not noticing the grimace on her face. This was so intoxicating! He felt something hard under he skin. She was making noises. He grabbed harder to figure out what it was. "Aah" Eventide hissed, grabbing his hands and pulling them off her breasts. "Not so rough!" the older mare glared, causing the teenager to blanch.

"S-sorry."

"It's okay, Gleaming," the escort reassured, her glare falling into a sympathetic expression. "Every colt gets a little overexcited the first time he's with a real live mare. Just not so rough, okay? Here, be gentle with me..." She pulled his head into her chest. "Lick and suck," she cooed, guiding his hand down lower. He felt the soft fabric of her panties. They were already moist. "Touch me inside." With that, Shining Armor maneuvered his fingers into her panties. For the first time, he felt a mare's slit. Whoa. He stopped his suckling at her teats to wonder in the soft, silky texture of her vulva. He found a nub and touched it. "That's the clitoris -- if you touch that just right, you'll make a mare very happy." She directed his hand just a little further down. "Now try this..." His fingertips pressed and her flesh yielded. Like that, he was inside her. She made a pleasured sound. "What do you think?" This mare was playing him like a fiddle, using her skill and cunning to get him past his awkwardness mostly unscathed. Well, as unscathed as could be done on any colt's first time, which was to say that if he didn't end up fabricating a much better story for his friends to cover his ass, that would constitute a success.

He truthfully didn't know what to say. This was fulfilling so many of his boyhood fantasies. Here he was, about to learn what true pleasure was, and at the hands of a genuine beauty. Twiley would have said something like his brain would have been melting from happiness. His mouth was dry, but he managed to get a few choice words out. "It's amazing," he said, smiling wider than the orbit of the outermost planet.

"Good. I like you, too. How would you like to be inside me?" She was fixing him with those trustworthy aqua eyes. In their gaze, Shining just instinctively knew he had nothing to fear. He nodded. She pulled off her panties before parting his robe. "Get naked," Eventide Velour said, smiling seductively at him, inducing the nervouscited colt to disrobe in a heart beat, lying on his back awaiting what was coming next. "Now just relax for a second while we take care of some business first, then it will be all pleasure." Eventide opened the drawer of the nightstand and pulled out a condom. She opened it, and placing it in her mouth, bobbed down on Shining's cock. He gasped in amazement, getting a warm smile from her. She sucked him for a bit, sending pleasure up and down his length with her tongue, lips, and mouth. She popped off it. "How does that feel, Gleaming?" Eventide asked, fingering herself to make sure she was wet.

"Good," he answered, now fully hard. "May I-" He blushed and caught himself for a few seconds while she looked on. "May I um, ummmm, well, uhh, do you?" His cheeks could have lit the bedding.

"Sure," said Eventide, taking position beside him and spreading her legs. "Have your way with me." She shoved him slightly, prompting him to take position kneeling between her thighs.

He crawled towards her, operating purely on base instinct. He shoved between her, awkwardly. She just laughed goodnaturedly and guided him inside with her hand. He gasped. So wet. So tight. So good. It felt like heaven! He didn't even notice the condom. Granted, raw saw may have just fried his neurons. She gasped, pulling him deeper inside her folds. Here he was, no longer a virgin. He was in a mare. He was fucking a mare! He was having sex! He was so excited, new, amazing sensations bombarding him in pleasurable barrages, that he lost control and went berserk, taking this mare, making her HIS whore. He had to copulate with her until he could do so no longer. He saw her tits bouncing, her lips parted, releasing delectable cries, calling his assumed name. It felt so good. He went faster and deeper, her legs locked around him to keep him trapped there until the deed was done and he was spent. Pleasure mounted light lightning, an electrical charge spreading from his groin to the entirety of his body. This had to be heaven. He was reaching a peak, a certain pressure as if his cock were going to explode. His balls had tightened. He tried to cry out, to say something or give her some warning like actors in porn did, but he couldn't make anything but a few strange noises before he lost control.

He came inside her. He came in that mare deep and hard. Madam Eventide Velour milked him for everything he had as it felt like rivers of cum flowed from his cock. He came so much it hurt slightly. He whited out momentarily from pleasure, unaware of what he was doing. That safe, familiar touch pulled him through. So good... He collapsed sweaty against his whore's chest, utterly spent, but at least presumedly happy about his entrance into her and manhood. This was fabulous. He held her close. She smelled homey, like lavendar. He muttered something happily before he fell asleep in her comforting embrace.

He could not wait to do this many more times.

And after he left, the mare breathed a sigh of relief as her mane cascaded free, turning again to strands of purple and white, her voice changing from the twang of Mustangia to the clip of Canterlot. She had to go home now, too; she had a filly and colt to take care of.

Author's Note

Thanks for reading. I hope to continue this fic soon. This is my first time tackling this subject matter. Thanks to Sparky Brony for editing. For Mothers' Day 2017. Keep calm and brony on.

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Kalash93