Winging it With a Ukulele

by hwrogers

Ch. 13 Surprises and Preparations

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For nearly an hour I sat, trying to piece together what had transpired this day, and failed in everything but sipping away the sample of wonderful beer I'd been sent. The beer gone, I got up and deposited the pile of porn into its designated spot, and went downstairs to eat while I sorted the additional contents out of the clocksmith's quarterly and set to read that for the rest of the day.


The next morning I got out of bed, got my shower and morning routine out of the way, got dressed up in my warmest clothes and set a pot of water to boil for my coffee before leaving for better coffee and muffins over at 'The Corner' as I'd come to call the Cakes' bakery. I am not a morning person by any measure, and so the sun shining brightly through the few windows that had the drapes pulled had averted my gaze. Done with the first step of my waking up schedule, I pulled on my boots, put on my grey duster coat and plaid flatcap, along with wool lined driver's gloves, and opened my front door to go to a proper breakfast.


"SURPRISE!" shouted an enormous congregation of ponies occupying my yard, as well as the street for a fair distance in either direction.

"Hey Pinkie," I groggily replied as I walked out to my gate. "Excuse me. Pardon. Comin' through," I said as I navigated the sea of ponies on my way to the bakery.


"HA! I knew it!" Carrot exclaimed just after I walked in and pointed to the blueberry muffin tin.

"So what's the news today?" I asked as I picked up a newspaper from the short pile that was always next to their register in the mornings and tucked it under my arm. "Blueberry?" I said, pointing again at the rack that held the completion of my morning ritual. 'The foals must have done something extra hilarious this morning, he never laughs this much,' I thought to myself as my friend got two of the items in question out and placed on a plate for me while I poured my own cup of coffee from the pitcher at the other end of the counter. "Slow day it seems, huh?" I asked as I sat down at my usual table facing the door.

Carrot laughed hysterically as I began eating my muffins and coffee. "Ha! you have no idea how rich you just made me! Do you?" he asked once he calmed from his gales of laughter.

"Six bits more so than before I came in?" I guessed.

"Ha! I'll leave ya to it then!" he said, walking back into the kitchen to what sounded like an excited conversation with Cup.


"Wait a minute. So you guys did what now?" I asked, not believing Pinkie's description of what had happened overnight.

"We wrapped up winter overnight to celebrate the six month anniversary of your arrival here in Equestria!" the pink pony exclaimed.

"You, you brought spring out early?" I asked, still not believing her.

"Duh, silly! Why else would it be so sunshiny outside right now?" she said in response.

"But why? That's not supposed to be till tomorrow isn't it? I thought you'd just throw the usual party," I said, still not understanding the situation.


A few hours later I had finished with the hoof-shakes and greetings and congratulations of my six month anniversary morning party and found myself quite happy to finally be left alone for a moment.

"Um, hi, Hoyt," said a grey pegasus as she took a seat across from me.

"Hey Ditzy, how ya Doo'in?" I said, smiling at my sometimes breakfast partner. "Cinnamon roll? Did Carrot already sell out of your favorite strawberry muffins today?" I asked, noticing her unusual divergence from the regular breakfast tradition she typically kept.

"Oh no, just thought it'd be nice for a change. Got a small side job today," she answered, smiling a little bashfully at me.

"Ah, going for a little extra cash for you and Dinky? What'll ya be doin'?"

"Oh, not too much. Just um..." she trailed off as her face was overcome with more blush than even Doctor could accomplish to pull from her in public. "Heh, um, Marieur... Ma- hoo boy," she said, getting my fullest attention. Then, after some more stammering, she took a deep breath and said, "Matchmaker. I have been hired to play the role of matchmaker... for you."

I picked up my coffee cup, slammed back the remainder of its contents, then pushed my plate to the side of the table and placed the cup on top of it. Then I folded the paper neatly and set it to the other side, and rested my elbows on the table. "Come again?"

"Matchmaker, somepony who asks a pony out on a date for somepony else," she explained. "Would you rather we discuss this at your house?"

"Yeah, go ahead and finish your roll, and then we'll go to my place..."


"I'm sorry, there must be something wrong with my ears today. Who did you say?" I asked, not believing what had just come from the blonde mare's mouth.

"Ahem, 'The Ladies Luna, Twilight and Rarity would ask that the Bachelor Hoyt,' that's you, 'accompany them to dinner, a show and perhaps other romantic activities as the mood may see fit.' Well, it'd be a smallish herd, but those are the best ones to be in," Ditzy said, reading the note again and confirming what I heard the previous two times.

I leaned back in my chair as it slowly sank in that I'd been delivered a proposition from not one, but three of the most beautiful mares in Equestria. 'Wait a fucking second here, what was that last part?'

"Y'know, if you wanted, you could have almost half of Ponyville for your herd. But then again, no stallion in his right mind would turn down an offer like this," she said, nodding at the note again. "So, what'll I tell them is your answer?"

"I uh, heh. Okay, tell them... Yeah, I'll just go to the library myself. Need to see about a book or two."


"Wait, so what about Shining and Cadance, the Cakes, Cranky and Matilda, or Berry and Shoeshine?" I asked, trying to wrap my head around what the three mares had just explained; stallions are expected to take multiple mares, and form herds.

"Shining has Cadance, Celestia, Gem Shine and Shimmer Heart in his herd. Carrot has Cup Cake, Pinkie Pie, Cinnamon Swirl and Roseluck in his. Cranky and Matilda are the only two donkeys in Ponyville, and they generally form very small herds anyhow, and Berry and Shoeshine are mares," Twilight explained.

"Why would it be different for mares?"

"You see, Hoyt, for a mare to expect a stallion all to herself is, well it's taboo," Rarity said.

"While for two mares to be monogamous together doesn't interfere with other ponies' chances to... perpetuate the species, as it were," Luna added.

"I thought you would have figured this out on your own, what with there being so many fewer stallions around," Twilight said.

"Honestly I had no idea, it looked like everything was pretty much the same in that regard. Wait, Celestia and Shining? But she's so much taller than him..."

"They make use of several non-standard posit-" Luna said before Twilight interrupted.

"Can you two PLEASE not discuss that right now? I have a hard enough time not thinking about that already!"

"Though it does bring a different thought to mind," Rarity said, hoof to her chin. Twilight shot her a suspicious glare, so she added, "Don't think me so crude darling, I'm not considering their situation... But our own."

Suddenly three very attractive mares were eyeing me closely, very closely with considering looks, and no doubt each was calculating her own methods of copulation. "Um, might I have any say in the considerations for how uh, that may be accomplished?" I asked, feeling the heat in my face reach critical levels and snapping the mares out of staring at me, more specifically at my gentleman's area. As the three all assumed bashful postures and massive blushing, I added, "I think we can cross that bridge when we get to it, don't you?"

"Um, yeah, that can wait for now... So, is that a 'yes'?" Twilight asked, looking up somewhat from staring at her hooves.

"Uh, y- I um... s- sure I- I guess. I mean, 'when in Rome' and all that, right?" My palms were sweating, I had no idea what to do with my hands, and my breathing and heart rates were both elevated.

"Are you sure? You're looking a little nervous, darling," Rarity asked, concern at the edge of her tone.

Glancing down I saw I had been fidgeting my hands. "Heh, yeah, I suppose I am, considering I've just been asked out by the three most beautiful mares in Equestria," I said, scratching the back of my head as they smiled and blushed from the compliment. "But yes, I'm sure. I'd have to be crazy or stupid to turn down an offer like that... And I guess it does make it easier, not having to choose."

"So, tomorrow evening then? To allow you time to prepare?" Luna asked.

"Y- sounds good to me. But, how does this normally work? I haven't actually seen any of the classically romantic things people do um, being done," I said.

"Well, Sugar Cube Corner and the library are hardly romantic points of interest," Twilight replied.

"Nor is the bookstore, darling. Though it can be a good place for gift shopping," Rarity said. After a glance around she added, "Though unless you get some other mares it may prove a bit pointless..."

"Yeah, I reckon that would explain why I haven't witnessed any such activities," I said, resting my chin on my hand. "So what did you gals have in mind?"

"Well..."


The next morning was similar, except that it included turning back into the house once I stepped out and noticed the temperature. Properly dressed for the weather I went as usual for breakfast, this time with no surprises and no winning any bets for anypony. "So, I heard you might have joined the game. Heard you did a pretty good job of it too," Mr. Cake said, joining my table with his own cup of coffee once he new I'd reached a civilized level of awareness.

"Hm? Oh, um yeah, I guess... How come I never picked up on that before though?" He gave me a questioning look, so I continued, "Herds, or polygamy as it would be called back home. I had no idea that was how things were done here. Back home you'd as likely get- well, let's just say the idea of more than one romantic partner is heavily shunned."

Carrot scratched at his head for a moment before he asked, "So what happens with the extra mares?"

"We have roughly even numbers in that regard, so monogamy is the norm, not the exception. I'm just wondering how I never caught on to how it works here though. Like with you in particular, I've never noticed any kind of... Well, according to Twilight you're with Pinkie and two others besides Cup, but I haven't noticed any indications of a relationship between you and Pinks," I said.

Carrot thought with a hoof to his chin for a moment before he answered. "Ya know how she tends to be the affectionate type? Hugging everypony and nuzzling her friends often?" I nodded, having observed as much from the pink mare. "Have you ever noticed that besides you and me she doesn't hug many other stallions, and I'm the only one she nuzzles?"

"Huh, I hadn't really paid attention to that. So what about, uh..."

"Cinny and Rose? They both prefer privacy, more so than even Cup."

"Well then... How often do y'all go out? As a herd I mean? Oh, sorry, I don't mean to pry, I'm just trying to sort things out, if you don't mind my questions," I said, realizing I had asked a rather personal question.

"Heh, it's alright, I understand your situation here. Normally most herds try to average at least one group outing or date each week, with missing a week here or there not being too great a concern. Now for my question though; Who did you get?" he said.

"Um, Luna, Twilight and Rarity," I answered, feeling at the same time proud, and slightly embarrassed as if I was bragging.

"Wow! I'd heard you had aimed high, but dang, you mean the two princesses and Ponyville's own fashion star?" he asked incredulously after his jaw returned to its correct place. I couldn't help but smile while I nodded and he added low whistle as he said, "Ha, so when's your first date? Tonight?"

"Yeah, yeah it is," I said, finding myself quickly warming to the idea of dating the three mares.

"Wait here a minute, I've got something for ya," he said before rushing out the door.

"What the Tartarus is he doing now?" I said to the empty bakery as Carrot rushed out the door and up the street.

A few minutes later I had finished my breakfast just in time to get my answer. Carrot came back in and had Roseluck with him looking a bit confused. "Hon, just what was it you had me come here for? I don't think I heard you, right..." she said, trailing off after she noticed me. "You mind telling me again?"

"Yeah, they finally asked him. So our friend here has a big first date tonight, and needs your help getting ready," Carrot explained.

"Now really, that's not necessary. I can handle getting myself ready for for a date," I said, smiling and politely refusing the help.


My objections fell on deaf ears as I found myself being pushed all the way to Ponyville's day spa. "Hightower here got himself a hot date. Let's get him fixed up," Roseluck said, informing Lotus (or maybe Aloe, I never could get their names right) of the reason why she had brought me here.

"Oh, is that so? Who are the lucky mares, Meester Hoyt?" the mare behind the counter asked brightly. Roseluck whispered in her ear a moment and her eyes shot wide. "Oh my, this is special indeed. To the massage room with you, hurry now," she ordered, coming around the desk to push me towards a door that lead deeper into the building.

Once through the door and a small corridor to another door, I found myself in a large room with several massage tables, and the other of the spa's proprietary sisters. As the door shut behind me the three mares huddled and only faint whispers and occasional words of a foreign language spoken aloud could be discerned as one or another would rise from the huddle to look at myself, the clock or the door. "Okay, Meester Hoyt, thees way please," the sister who wasn't at the front desk said as she beckoned me to follow her to a corner of the room separated by some folding partitions. Behind the portable walls was a much larger massage table, long enough for someone even taller than myself to lay on comfortably. "Thees is our special table for clients of your particular proportions, or Celestia when she chooses to veesit," she said.

"Alright, here's a towel, once that's all yer wearin' Aloe here will start your massage, and in the meantime I got something else to go get ready for ya," Roseluck said with a wink as she placed a large towel on the table before running out while I heard muffled hoofsteps of several ponies entering the main area of the massage room.

The blue maned pink pony sat facing the opposite corner from where I was standing. "Um, is this all the privacy I get while undressing?"

"I am a professional and must alzo respect the privacy of the other clients. You can trust that I vill not be looking until you say you are ready," she said, turning her head down so as not to be speaking directly away from me.

"Alright," I said, deciding to invest some trust in the masseur pony, and making a mental note the she is Aloe, and her blue sister is Lotus. "I'm ready," I told her once I had taken off and folded my clothes and put the towel on over my boxers.

"Vedy well, if you would please lay face down on ze table, and I will begin the massage," She instructed as I heard idle chatter from the main portion of the room.

"Okay," I said as I moved to cooperate. "Never had a massage before. Is this normal for a stallion going on their first date?"

"Not every stallion, no. But then it is hardly common for a stallion, even one such as yourself, to get the attentions of a princess, much less two and our own Rarity as well..." she answered as I heard her shuffle around some bottles before feeling oil drizzle onto my back and shoulders. "You may not know eet, but you are quite the catch," she said as her hooves began pressing into my back. "Oh my, so much tension. You really must try to relax more."

"Sorry, I kinda picked up my Mom's stress levels, and these last two days haven't really helped," I said, chuckling a little into the cushioned table.

"Wow, she must bear the weight of the world if you inherited thees much stress in your poor mooscles... I'm going to have to mount the table, just relax Meester Hoyt, and I vill be relieving you of thees tension," she said as I felt the table shift slightly before more firm pressure was applied.

"Ahhh... That's the spot," I said involuntarily as she brought all four hooves and her full weight to bear on my back, soothing aches I wasn't even aware of.


"Why did I not do this before?" I asked nopony in particular as I felt even more relaxation course through me from the hot bath. "If I'd known about this, I probly would have been here every day of winter!"

"Eyup, it sure is nice isn't it?" asked a voice I knew all too well.

"Hey Mac, you gettin' ready for a date too?" I asked, eyes still closed to focus on the pleasure of the bath even as I felt the waves of his entry from the far side.

"Heh, nope, not a special date anyhow. But I did hear you got a princess or two... Maybe even a certain fashion obsessed unicorn as well. You done good from what I heard," Macintosh said with a chuckle.

"Heh, yeah, guess I got quite the set I reckon. But what brings you here if not a special date? I never took you for the type to come to this sort of place," I said, inquiring to the farm pony's reasons for being at the spa, opening my eyes to see his expression.

"Oh, I come for a hot bath every couple weeks, helps to relax," he said. After sinking his head in and shaking around for a moment he emerged and added, "Course, don't hurt that Aloe likes it when I stink pretty."

"No shit, Aloe?" I asked, somewhat surprised by this.

"Eyup," he said with a wide smile.

"Easy to see why you're always so relaxed then," I said thoughtfully.

"Last I heard, Lotus may be available... If you're interested." His tone was suggestive, as was his grin.

"Ha, I think I'll have my hands full enough already Mac. Not that the thought isn't appealing, I'll admit," I told him, stretching my arms.

As if on cue the blue pony entered the room. "Meester Hoyt, we are ready for your next step as soon as you are dry," she said, placing a couple of towels at the side of the hot tub.

"Next step? What all do you gals have planned for me?" I asked as I stood to wade over the the side where the towels were placed.

"You have a date with two princesses and our best customer, and so we are going to do our very best to be sure that their stallion is presentable to the highest standards," she replied confidently with a tone that brooked no argument.

"Their stallion eh?" I said, smiling as I glanced between the two ponies. "I think I could get used to that. Next step it is then," I continued, grabbing one towel and starting to dry my hair and beard.

"Are you wearing your shorts? In the hot tub?" Lotus asked.

"Well yeah, a gentleman doesn't go giggling his giblets about where others can see," I replied from under the towel.


When I finally left the day spa Roseluck led me to a light lunch at Cafe, apparently it is considered poor form to eat too little on a dinner date, and then to my house, where she proceeded to rearrange what I had chosen to wear the previous evening for a different outfit which included a flower that she had carefully crafted for the event. "The speckles for stars were difficult, but not beyond my capabilities," she said, smiling at the multi-colored daisy that now adorned my chest, featuring the colors of each mare I was to be courting in successive rings.

"Earth pony magic, another thing I will likely never fully comprehend," I said, admiring the beautifully colored flower myself. "Are you sure I should wear the kilt and not the dress pants which Rarity made to match the jacket?"

"Well, given that you are averse to nudity, I would say that this is the best you could dress for the occasion," she answered with a smile. "It doesn't hurt to show some fur after all."

"Yeah, I guess my legs have enough hair to count as furred. Almost," I said, looking at myself in the tall mirror. My appearance had changed considerably since coming to Equestria; my beer-belly was all but gone, my arms had gained bulk despite my generally sedentary lifestyle, and perhaps the most noteworthy change was my beard; a proper Shenandoah style trim that I had taken up after some sidewise remarks at a garden party back in Canterlot. "Alright, since you're my fashion consultant for the day I'll take your word on it."

Rose nickered at that, rolling her eyes. "Fashion consultant, yeah right. Anyhow, I'm out, got some work to do to get my inventory ready for market season," she said, moving towards the door.

"Hey," I said, stopping her before she left. "Thanks for helping me out today. Tell Carrot that y'all are welcome to come over for dinner sometime."

"Dinner? What kind of dinner?" she asked, turning back to me with a very curious expression.

"It's my way of saying thanks, beyond just the word," I explained.

"Oh, alright, I'll let 'em know. Catch ya later Hoyt," she said as she walked out the front door.

"See ya 'round Rose," I said before closing the door and turning to the clock. "Ah, five minutes to three, just about time... Oh, what have I gotten myself into..."

Three knocks sounded from my front door, signalling the arrival of what I just realized was the most nerve wracking event of my life.


Author's Note

Bracing for impact, shitstorm imminent. Then again, anyone who didn't see this coming, didn't pay much attention :derpytongue2:

Thanks go yet again to Sneaky for proofreading and making sure I don't screw this all up, which he did do twice for me this chapter. Go check out his story 'Close Bonds' or he has several others that are quite good.

So, how was that for a bombshell?

P.S. The russling is over 1.5 Megajimmies. But really? Shining boning Celestia is the cause? Wtf people...

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