“Are you awake?” Cheerilee asked, softly.

I thought it was quite an odd question to ask first thing in the morning, but remained still. Curiosity got the better of me. And if it wasn’t quite so obvious yet, of course I was awake. I always awoke when the Equestrian sun struck me and even now, I have no idea why. It was as if there was something in Celestia’s Light that triggered an alarm clock inside me. It mattered not if I had slept only an hour ago, every time the sunlight hit, my eyes would open.

In most days, it would have been a blessing. Gentlemen were supposed to disappear once the sun rose. While it was not a policy I agreed with, the boss has been adamant on it, and I always tried not to be insubordinate.

Yet, staying in with a mare was very... comforting.

I was currently in Cheerilee’s bed, having been awakened almost ten minutes ago in her warm embrace. I could hear her snore gently as she had snuggled intimately to me, and in turn, I nestled closely, comfortably on her neck, enjoying the slight prickly feeling of her coat as I took pleasure in the oddly satisfying scent of her sex and musk.

I remembered that I had one more day with her and I wasn’t about to waste it, my mind already planning something special for her today. Maybe some breakfast in bed? A nice coat brushing would be a nice touch. Or maybe a personal bath together? As I began to think of other ways to begin her day, she had suddenly asked me that question.

“Are you awake?”

I said nothing, wondering the reasoning behind the question. I kept my eyes closed, feeling her shuffle slightly, trying her best not to try and wake me, I supposed, as she separated herself from me. I shivered slightly from the chilly air that made itself readily present, missing her warmth as I felt her move around the bed.

For a moment, there was nothing. The next, I felt warm gentle suckling sensation of her hooves hovering over my stomach, and to my surprise, began its journey downwards. I almost bit my tongue as I felt her two hooves gently massaging my naked exposed member.

“Please don’t wake up,” Cheerilee began to chant fervently.

Yeah, a little too late about that, I thought.

I suddenly felt her shifting her hooves in an up and down motion, feeling her hot breath encompassing my manhood. She then stopped chanting a few seconds before I felt her tongue work on my growing erection.

Through all that, I suppressed my groans. For some reason, Cheerilee wanted to have a little fun while I slept, and having heard her whisper it so cutely, so passionately, I did what she wanted. I pretended to be asleep. Well, at least, as best as I could with a growing erection. Her hooves and tongue worked wonders on me as I felt a little unbridled lust as she sloppily took me in her mouth and began to suckle on it with gusto.

How could I describe the feeling of her thick wet tongue moving in interesting ways, circling, licking, while her warm mouth blanketed my manhood from chilly air as I felt the ghost of her teeth adding texture to the whole experience? Or how should I express the fact that the sloppy noise of her mouth going up and down on me was probably the most stimulating thing I have ever listened to? Or how about how I felt the warm, suckling sensation of her hooves between my thighs, spreading and holding them in place as she worked?

I can’t. All I can say was it was thoroughly enjoyable, all of it.

Minutes after building me up, she stopped. I almost groaned my protest, but kept my mouth (and eyes) shut. I felt her hooves letting go of my thighs as the bristly feeling of her warm coat slowly enveloped my legs. I felt the bed wobble slightly as she began to clamber on top of me. I could feel her nuzzle me in the neck as warm liquid began to pour over my thighs and manhood. I was also verily aware of her mare folds winking, enclosing at the tip of my erection once or twice.

“Please don’t wake up,” she begged as she lowered herself.

A grunt escaped my lips. I couldn’t help it. Her marehood felt very hot, feverishly so, as it surrounded me. The walls pulsated, moved in random waves as Cheerilee lowered herself totally, absorbing my length. She struggled as she climbed up, but couldn’t get far as her own walls betrayed her, clamping down around my manhood.

Still, with what little she could, she continued in the slightly odd rhythm. She would lower herself and clamber as high as she could, letting her hot and moist walls gleefully rubbed itself around mine, causing an immediate build up of pleasure as I felt the imminence of my ejaculation. I shifted a bit, forcing myself to still my hips as I felt her moving up and down.

She still chanted, begging me not to wake up, but as time passed it was getting harder and harder to fulfill her wishes. My pleasure was passing through its final threshold, and I could only just stop myself from opening either my mouth or eyes as I came inside her.

Cheerilee shouted for almost a second before it turned to a muffled whine. I could imagine herself biting either her lips or front hooves as she finally settled herself to the whole of my length, letting her vaginal walls twist around me, hoping to extract from me all of my juices. It continued on for several seconds, and once more, I was reminded on the exquisite pain of pleasure.

Thankfully, Cheerilee successfully withdrew herself from around me, almost landing on top of me painfully as my manhood was freed from its hot erotic confines. I could feel her lips on my chest as she panted, her body twitching ever so frequently that it touched on my softening sensitive member. I couldn’t help but wince as a something akin to a spark of electrical current travelled from my manhood to my spine.

We stayed like that for a moment, with me enjoying her twitching and warmth. She slowly nuzzled me, licking my neck as she tenderly enveloped me in a hug.

“Thank you... for pretending,” she whispered.

I opened my eyes, and saw her; a beautiful cherry-pink coated earth pony with a two-toned pink mane, looking back at me with mesmerizing light-green eyes. She licked me softly in the cheek before she snuggled her head on top of my chest.

“You knew?” I asked.

“Yes,” she replied in whisper, her tone somewhat sad. “I used to have coltfriends who would pretend to sleep when I turned the conversation something a bit deeper than the weather.”

“They sound like jerks,” I commented. Cheerilee gave me a sad smile.

“Maybe,” she replied, her tone going soft again. She kissed me on the neck once more, sending some good shivers down my back. “It wasn’t really their fault, and I got used to it. This is the first time I recall really appreciating someone pretending to be asleep for me, though. You’re a kind stallion – er, uh, man?” When I nodded, she continued. “Okay. You’re a very kind man, Mister Wingman.”

I moved my left hand, and arched it over her head, letting my fingers run through her mane as I felt her shiver.

“Was that another phase?” I asked gently. I just felt her nod. “You could have woken me, Cheerilee. I’m here to take care of it, and you.”

She was silent for a few minutes. Then, she sighed.

“I...” she began, but stopped for a few seconds before she continued. “I’m sorry. I don’t particularly feel comfortable in letting anyone help me in regards to this. I... I know you are here to help me through the phase, but...”

She trailed off, leaving the sentence hang in the air. For a few minutes, I just continued my ministrations, stroking her mane gently before I extracted myself out of her embrace. I saw the slightly surprised look on her face before her eyes suddenly went down, her lips frowning slightly before I sat at the edge of the bed and stood up.

“D-did I offend you?” she suddenly asked, her voice growing concerned.

I grabbed a fallen pillow off the floor. I gave her a warm smile, and said, “No,” before I threw the cushion gently at her head. She caught it easily with her hooves and gave me a confused look. “I just thought it was prudent to be up and about. Don’t you have classes today?”

Cheerilee blinked and she realized, after a few seconds, the truth of my words. It was entertaining watching what came next; from her prone position, she suddenly jumped and sprung up from her bed and landed all-fours on the ground, like an equine gymnast. Seeing her cute panicked face as she looked around wildly was an added bonus.

“Oh, no! I have to bathe, I have to get breakfast! Oh my... what time is it? I can’t—” and I cut her off with a finger on top of her lips.

“Take a bath,” I ordered. “I’ll take care of breakfast.” When she was about to protest, I shushed her. “Don’t make me repeat myself, Cheerilee,” I declared with a bit of a stern tone. “I’ll take care of breakfast, so you go on and take a bath, now.”

Her eyes sparkled slightly as she looked at me. It was an odd look, as if her eyes expressed both a mix of lust and respect behind them. She could only nod and slowly trot off in a direction, hopefully, towards her bathroom. Satisfied, I began my search for my underwear and clothes, dressing up before I walked towards her kitchen.

What to cook, I wondered as I began to go through her pantry. The icebox had a few bottles of drinks, water mostly, though there were at least two bottles of milk, one, which was half-full, labeled as Buttermilk. There were also a few brown eggs, and a bowl of what looked and smelled like fresh butter, and I also spotted fruits and vegetables, though nothing I could really use to serve a full breakfast. Her cupboards though had a good collection of flour, baking powder, and other items. What caught my attention was a small jar of thick dark-brown maple syrup.

Yeah, I think I know what to cook.

Getting a flat pan and a few bowls out, I made sure I had enough ingredients before I mixed them, separating the wet and dry ones into different bowls. I kept hesitating when it came to handling the fresh butter as I really wanted to taste it. There was something incredibly enticing about freshly churned butter, complete with liquid dribbles on its side, that I could not describe.

I was not a great cook. Heck, I didn’t know how to cook until I came to Equestria. It was made worse when I found out Equestria wasn’t that advanced yet when it came to food technology. Every ingredient was... ‘fresh’ for lack of a better term, making almost any trade between villages and cities reserved for preserved goods, like cider, baked goods and dry ingredients such as flour. It was expected that every Equestrian city to have their own land reserved for growing food.

It also didn’t help when the Diamond Dogs had gotten bolder over the years with their raiding.

Living all alone for a few months pretty much gave me a crash course in kitchen. I had no ‘instant’ food products. I had to obtain ingredients freshly made or harvested, and also had to learn how to cook them myself. So, yeah, no instant pancake batter, no cans of tomato sauce or mushrooms.

I missed the dried pasta, though. Fresh ones tended to spoil faster.

So, yeah... living in Equestria was like living in a bit in an older time, I guess, but one good thing came out of it; the practice paid off. I make the meanest batch of pancakes.

Don’t ask me to cook pasta though. Last time I tried, the fettucini I was cooking turned to macaroni.

Yeah, like I said, don’t ask.

The batter was ready. Heating up the flat pan over the stove was an easy enough task and by the time Cheerilee walked in the kitchen, I was already done cooking the fifth pancake.

She smelled nice. A bath did her good, almost removing the telltale scent of musky sex that clung to her the whole night (not that I minded). Her scent, a mix of earthy floral sweetness, blended well with the smell of the golden brown buttery goodness of the pancakes.

“Oh, that smells good,” she mumbled, her jaw holding on to a brush as she trotted into the kitchen. Her mane and tail were still slightly damp, and a light pink towel wrapped around her neck. I swear to God, she pulled off the wet look so naturally. She looked absolutely delicious.

I placed three fluffy pancakes in a plate, spread out in a semi-triangular shape. I put some butter on top of the three pancakes, letting its still-warm presence melt it as I placed it on the table.

“Come on, Cheerilee, dig in,” I said, motioning her to sit down.

“Oh, I can’t yet. I have to brush” – and I cut her off.

“Cheerilee,” I said, my tone turning a bit stern once more. She gave me that same odd look like earlier before she slowly settled to her seat. I gently grabbed the brush out of her mouth, and offered to pour syrup on her pancakes, only stopping when she told me to.

It was always interesting to me to see ponies work on utensils. With deft practice, her hooves grabbed out a fork and a knife, and with very human-like motions, worked on her pancakes, slicing smaller bits, stabbing them with the fork, and putting the morsel in her mouth.

She groaned slightly, and then blushed when she realized how she sounded. “This is good,” she muttered quietly.

“Glad it is,” I replied before grabbing her brush. “Cheerilee, I’m going to brush you, so just worry about eating right now, alright?”

I thought she was going to protest, but she just nodded and continued eating. I positioned myself behind her, admiring the mussed-up look of her wet coat and the messy style of her mane and tail as I placed my hand on her side, my fingers enjoying the feel of her short cherry-pink hair. I felt her shiver at contact, and a soft groan escaped her lips.

“Mis-mister Wingman, you’re insatiable,” Cheerilee accused. I just smiled.

“I am just admiring a beautiful mare,” I replied easily. “Besides, Miss Cheerilee, I’m not doing anything untoward.” I put a little gruff on my next words. “Unless you want me to, of course.”

She shivered again. “Y-you think I’m... beautiful?”

I picked up the brush with my right hand, and with my left, I smoothed out her coat a bit before sweeping it with my right. “Of course you are,” I replied with total honesty.

We stayed like that for a while; she ate her pancakes while I continually brushed her coat systematically, three strokes per column, smoothing the short hairs into a soft finish. I then began to work on her mane, trying as gently as I could to untangle the knots with my fingers before flattening it with the brush.

“You know, I’m tempted to nuzzle you,” I said, continuing my ministrations. “You smell really good.”

She shivered again. She said nothing, but just continued to eat. I, in turn, just continued to groom her.

It was a beautiful morning.

Cheerilee just left for school, leaving me for clean-up duty. She had tried to protest, again, saying she should at least clean up her own plate, and I’d advised her she was already running late. I didn’t even need to put a stern front again, just mentioning the fillies and colts was enough to push her out of the door.

She cared so much for her students. I wished I had someone like her for a teacher when I was a kid.

Making sure I had arranged everything in the kitchen, I stepped out into Ponyville, just in time to see the morning bustle. As I made way to the central hub, I spotted groups of ponies walking in random directions, talking and interacting – not unusual for a morning routine. There were some humans as well, mostly dressed in casuals or in sweat suits, jogging along paths with their companions (pony or otherwise). I thought it was strange to see so few people until I passed through the train station. There, I saw more people dressed in professional capacities, probably off to work.

I stood still for a moment, watching them. I remembered that if circumstances had been different, I'd probably have been one of them. I shook my head and I walked past the central hub, my eyes searching for the specific sign. I had spotted it from a corner of my eye yesterday, and I could have sworn it was somewhere around—

Ah! There it was.

I walked up to the stall, making sure the sign did indeed have the three white clouds and purple hot air balloon over the light blue background before I approached a bored-looking off-white pegasus mare with somewhat puffy blonde mane and tail. She even yawned a moment before spotting me, and immediately stood up, alert.

“Hi!” she greeted with cheer. “Welcome to Amour Veil! My name's Surprise.”

I smiled back. “Nice to meet you. Name is Wingman, and I want to set up an appointment for later this evening.”

“A little date then?” she asked.

“Yup.”

“Alright,” Surprise declared and ducked under the counter, coming back up with a parchment and a human ballpoint pen (ponies loved them, and it was slowly replacing quills as the mainstream tool for writing) and handed them to me. “I need you to fill up these forms. And you’re in luck. Nopony... um, I mean nobody has scheduled anything for later.”

“Slow day then, eh?” I asked as I read through the parchment. It was the usual reservation form, something I had recognized and filled dozens of times already.

“Yup,” the pegasus replied. “Not a lot of customers for the weekday. I usually get more reservation requests tomorrow. Lucky for you and your girlfriend, skies will be all clear for both of you.”

After I finished filling up the parchment, I paid her in bits and went on my way. Next stop? Carousel Boutique. I was feeling a bit generous with my money, especially knowing I was given an in-heat rate for two days. Also, Eve may have finally infected me with her thoughts as I felt that, with the boss paying more than half of the fee herself, I could splurge a little. Besides, I could use with another set of attire.

Of course, I couldn't deny that I also wanted to see Miss Rarity. There was something about her that grabbed my attention. Maybe it was the contrast of her attitude? She had that air of sophistication that was not misplaced in Canterlot or the bigger cities, yet she showed no sign of the extreme pompous pride and arrogance that many nobleponies displayed.

It also helped she was very easy on the eyes.

I knocked at her door on my arrival, waiting just a bit before I heard a muffled voice coming from the inside.

“Come in!” Rarity’s greeting came out in a sing-song voice.

Entering, I immediately noticed the purple tones of the place. Darker ones crisscrossed in diamond patterns over the lighter shades, creating a design not unlike a fence one would see in a circus fair. Columns were strewn all over the place, giving the surrounding an edged look, and between each column was a large circular window with drawn violet shades, letting in enough sunlight to give the interior a soft glow.

I also spotted pony and human mannequins placed randomly at one side, near the sewing machine and the wooden display that showed off different cloths, threads, and gemstones. Pony figurines sported some of the most complicated-looking dresses and suits. It was a stark contrast compared with the human models, which, while their attires were pretty elaborate and well-made, were far more subdued to fit human fashion culture.

The arrangement was far from tidy, though unlike Cheerilee’s mess of a house, the shop had a look of order in its chaos. All in all, it looked like it was always busy; much like its owner, I ventured as I saw Rarity. She hovered in front of a pony mannequin, sprucing it up with a dark velvet cloth. She was, judging by the way she bit her tongue and the concentrated look behind her red cat-eyed spectacles, carefully sewing the seams. Her magic was working its wonders as the needle and thread, glowing with ethereal light-blue aura, weaved around the cloth in a precise rhythm.

I stayed quiet, unwilling to break her concentration, as she finally began to put the finishing touches. Once done, she turned around, giving an easy smile as she greeted, “I’m very sorry about that. Welcome to Carousel Boutique! Where everything’s—oh, Mister Wingman. What a surprise. It’s a pleasure to see you again.”

“Pleasure is all mine, Miss Rarity,” I greeted back. “I had some free time, and I thought I’d take you up on your offer.”

She blinked and looked a bit confused. “Uh, what offer is that, exactly, darling?”

“You mentioned I should visit whenever I needed new clothing?” I reminded her.

“Oh...! Oh, quite, yes.” She shook her head a bit. “I’m sorry about that. My mind went to places.”

“Why, Miss Rarity... were you thinking of something quite naughty?” I joked, smiling.

Her cheeks blushed lightly. “Now, Mister Wingman, it’s quite rude to tease a lady,” she replied. She tried to sound stern, but her ever-present smile gave it away. “Actually, I’ve been somewhat busy these days, so pardon me if I seem a bit slow on the uptake. I hope the mess of my shop doesn’t turn you away.”

“It just tells me you are quite the busy mare,” I said, and motioning towards the human figurines. “I am actually quite impressed by your sense of human-style fashion. I’ve visited a few stores in Manehattan and Fillydelphia and for some reason they insist of trussing us up in innumerable layers of clothing.”

“They don’t tend to get a lot of human customers, do they?” she asked. All I could do was shake my head. “Well, I don’t mean to speak ill, but it’s no surprise. A lot of ponies are a bit stubborn. It didn’t mean I was much better, of course. My first foray to making human attires ended up in a complete disaster!” She raised her eyes to the sky as she rested her right foreleg on the top part of her head, just below the horn. “Oh, it was quite a horrible time!”

Wow. She can be dramatic at times. My smile widened.

“At least you got better, though, right Miss Rarity?”

“Well, I had to import Earth fashion magazines. Oddly enough, some styles were akin to mine, but there were a lot more conservative designs that I tried, and lo” – she pointed towards the air with her right hoof, smiling wide – “I sold out!”

Yup, she definitely had a flair for the dramatics. I just stayed quiet as she continued to speak, motioning me to towards an elevated stage near the center of the shop, dragging a tape measure, pencil and a human mannequin in tow.

“I then realized something so obvious: humans don’t regard clothing as something only worn for special occasions, but an essential part of their lives! They wear it every day, whether it’s for work, while at home, visiting friends, or even swimming! It was so strange to me.”

“I actually understand that, the strangeness,” I replied, smiling as I remembered my first visit in Equestria. “When I first arrived, I was behind a mare and she was in quite an animated conversation with another pony. Her tail kept swishing left and right, which basically exposed her. My face was as red as a tomato.”

“Oh, dear!” Rarity exclaimed, chuckling slightly at the imagery. “Did you say anything?”

“What was I supposed to say?” I asked. I cleared my throat and spoke with a slightly altered tone, deeper than my usual voice. “Oh, excuse me, miss, but I just got off a boat ride and passed through time and space. I know Equestrians are friendly, but not this much, please. Hoh-oh no. The way I was positioned behind her, if she took offense, it wouldn’t turn out well for me. And you know what was worse?”

“What was that?”

“She and I had the same destination. I could not look at her, at all! I tried to cover my eyes slightly, subtly with my hand, always avoiding her position,” I finished, mimicking my actions with my right hand, open-palm, index to the forehead and thumb to the cheek. Rarity began to stifle her laughter with her hoof. It reminded me how the other ponies at that time reacted to me.

Good God. That was really an embarrassing moment for me. And it also didn’t help that Miss Rarity’s chortling was getting louder.

“Well, at least you are enjoying yourself,” I said in mock anger, crossing my arms over my chest. “Here I am, pouring out my heart and soul, and there you are, mercilessly, gleefully stomping it all over the place. You are a cruel lady, Miss Rarity.”

“Oh, hush darling,” the unicorn declared with a final giggle. She then turned her face, blinking as she gave me a look. “I’ve played that game a thousand times,” she said, giving me one of the most powerful pouts I’ve ever encountered in my life. “Do you want to take me up on that challenge?”

“No,” I said immediately. Wow, that was really unfair. I'm not a stranger to pouting mares, but Rarity's was... just wow. “You win, Miss Rarity.”

Rarity said nothing, just giving me a smile as she snaked her measuring tape around my waist. For the moment, we stayed in comfortable silence, with the dressmaker unicorn writing the measurements down on the human figurine at the same spots where she measured me, with off-hand comments of ‘oh, interesting’ and an ‘oh, my’ for good measure.

I have no idea what was so interesting in my measurements to warrant those comments. And no, she wasn’t measuring anything... ‘dirty’.

“So, how is your tête-à-tête with Miss Cheerilee?” Rarity suddenly asked as her tape measure encircled my arms.

“I’m not the type of Gentleman that kisses and tells, Miss Rarity,” I replied with a slight smile.

“Of course not,” the unicorn declared with utter seriousness. “It is just... well, I sometimes worry about her.”

“What do you mean?”

The unicorn bit her lower lips, her eyes scrunching over a decision. After an internal struggle, she shook her head. “I am not quite... comfortable talking about another fellow pony. She isn’t exactly a friend, but she’s no stranger either. Ponyville is quite a close community; you should ask my friend, Pinkie Pie. She knows the name of every pony, zebra, mule, and human in town.”

“Applejack mentioned someone named Pinkie. Are they one and the same?”

She smiled and nodded. “Applejack and I share the same circle of friends. And if you meet her, you’ll know that there’s definitely only one Pinkie Pie. Thankfully, she’s out of town.”

Huh. That was almost exactly what Applejack said yesterday. What warranted such reaction from both these ponies, her friends? This Pinkie Pie sounded... dangerous.

“Where was I? Ah, yes,” she continued, her tape measure now going around my legs. “I know you’re here to take care of her, but as far as I know, you’re still quite a stranger to town. No offense, darling.”

“None taken,” I assured. “The reason why I’m curious is because she strikes me as a very lonely mare.”

Rarity sighed. “That she is. That she is,” she replied. She looked pensive for a moment before she took a final measurement and wrote down the numbers on the mannequin.

She then turned towards me, smiling slightly. “I may be uncomfortable talking in regards to Miss Cheerilee’s private life, but,” she paused, “you are quite a bright young man. You could probably guess that she hasn’t had much success in her romantic pursuits.”

I blinked, then looked at Rarity as she smiled a bit more deviously. I just shook my head, letting my lips curve upwards.

Oh, Rarity, you are quite the mare.

“She also strikes me as a mare who doesn’t have much confidence in herself,” I ventured.

“If that’s true, and I’m not confirming it is, you could guess her lack of confidence may have affected the premature end of her relationship with Big Macintosh, even though they had something quite heartwarming. However, I can’t tell, and I really apologize about that dear.”

I blinked.

“Big Macintosh, eh?” I asked, letting my mind wander a bit. I heard the name, yesterday. Wasn’t he the big red stallion of Applejack’s?

“If you could talk to him, you could ask him about the details,” Rarity replied. “I can’t tell how much he’ll reveal, but then again, I’ve never been quite clear on the rules of talks between stallions.”

“I would, Miss Rarity, but considering how Miss Applejack seemed a bit, uh, apprehensive on the nature of my work, wouldn’t I earn more of her ire if she saw me talking with her stallion?”

Rarity blinked, her face showing an expression of utter confusion. Then, she broke out a smile, her lips quivering before she burst out in a full-on laughter.

Oh-kay?

“Oh my goodness,” the unicorn began, breathless. “You think Applejack and Big Macintosh are together... in a herd!?”

I could only nod stupidly. I could only assume I was missing something here.

“My dear Mister Wingman, Applejack is Big Macintosh’s younger sister.”

I think my jaw dropped to the ground, and judging by Rarity’s even louder guffaws, steam was coming out of my ears as well.

“Okay, I’m keeping my mouth shut before I embarrass myself further,” I muttered.

“Whatever you say, darling,” she teased.

After all the measurements were done, she and I delved into the colors and styles of how I wanted my clothes to be done, and the matter of payment. I was once more surprised at how low the price sounded, considering all the materials she had enumerated, but she just advised me that since I was a first-time customer, she was giving me a bit of a discount.

I told her she was being a bit generous. She replied, with a slight giggle, that she was known to be quite so.

Okay, that nagging sense that I was missing something returned, this time with a full band of horns and slide whistles. Was there a joke in here, somewhere, that I wasn’t aware of?

It was five o’clock. Anyone coming in just now missed a storm of fillies and colts as they flooded out of the building. And judging by my still ringing ears, the volume they had exuded was much stronger than yesterday’s celebration.

I stood there and watched as all the foals met up with their parents or guardians, all smiles as they finally finished school and could enjoy their weekends. I’m not ashamed to say it, but it warmed my heart. After a while, I saw those three fillies again, Apple Bloom, Sweetie Belle, and Scootaloo. The former was seemingly happy their teacher was now acting relatively normal, and that I apparently did some good work in letting Cheerilee have fun.

It’s nice to get praise from kids, even though they had no idea what they just thanked me for.

Unlike yesterday, though, Applejack or Rarity weren’t present to pick up the fillies. Big Macintosh was there instead. Apparently, with the weekend looming, the three were going to hang out at their clubhouse and continue with their ‘Crusading’. I wished them luck (even though Scootaloo was still looking at me suspiciously) and watched them leave, escorted by the big red stallion.

I was still conflicted. Part of me wanted to talk to Big Macintosh. Another told me to leave it be as I was already treading on uncharted territories by exploring the personal life of a first-time customer, and I didn’t want to needle into affairs I had not fully understood.

It didn’t help that the stallion looked quite intimidating. He was larger than any other stallions I had met, and had quite a deep voice too. That was enough to let me know that, if he wanted to, he could knock me out six-ways from Sunday and Friday (or at least, the Equestrian equivalent) was barely over.

Yet he struck me as a quiet type, more of a listener. He had given me a slight look when he first spotted me. I half-wondered if Miss Applejack had told her older brother about me, but he didn’t show any aggression or even voice an opinion. He just greeted me with a nod.

One odd thing I noticed though was the fact that he had increasingly been receiving stares from a lot of mares, who either passed by or were there to pick up their foals.I was pretty sure Big Macintosh here had some pretty interesting stories to tell.

Now, watching him leave, I wondered if talking to him (even if it was just regarding mundane things like the weather or Ponyville life) would have been a fruitful pursuit.

Well, no use wallowing over wasted opportunities. With them leaving, like yesterday, I was left alone in front of the red building. I felt a wave of trepidation once more, though this time, the school didn’t look like it wanted to swallow me, nor did I feel I left my scrotes at the market. A rational part of my mind reminded me that I was probably nervous because this was actually my first proper outing with Cheerilee and I wanted this to go perfectly.

I entered the school building and knocked on the door leading towards the classroom before I entered. I spotted the cherry-pink earth mare at the end of the classroom, humming a happy tune as she erased the writing on the blackboard. When she spotted me, she smiled ever so slightly, which matched well with her growing blush.

“Mister Wingman,” Cheerilee greeted.

“Hello beautiful,” I greeted back. If possible, her blush went a shade deeper. “Enjoyed your day of teaching?”

“Quite,” she nodded. “I felt another phase during lunch, but i-it didn’t affect me much. And w-with you here...” she trailed off.

I approached her and went down to one knee. My hands cupped her cheeks and I slowly approached, positioning my lips to kiss her. I let my tongue split her lips open, touching her tongue ever so slightly before we lost ourselves, exploring each other. Cheerilee’s face began to heat up as she stepped forward, deepening our little embrace.

I finished by moistening her lips with a lick before separated from her, smiling. I said, “I’m quite proud of your self control, Cheerilee. I’ll make it up to you.”

She shivered, looking at me with pleading eyes.

“Here, now?” she asked throatily.

I brushed her mane with both my hands. I shook my head. “I have something else in mind. Can you hold off until later tonight?”

Cheerilee blinked in confusion. It took a moment before she nodded. “Uh, sure. Why? What do you have planned?”

I gently grabbed her right foreleg, and with practiced motion, placed my lips on her hoof, kissing it.

“Let me have a chance to take out a beautiful mare on a date,” I replied, whispering it slightly. “Allow me to shower her with praises, celebrate on her beauty of both body and soul. We’ll have a nice meal between us. Let me treat you in a way I think any proper mare should be treated, under Luna’s veil of stars.”

She giggled slightly. “The dramatics don’t suit you, Mister Wingman.”

True. We can’t all be a certain Ponyville dressmaker.

“But... yes,” Cheerilee finally replied.

I smiled. “Good. You’re going to love this.”

“Maybe I should have stated that I reserved the right to change my”—Cheerilee shouted the last word as a strong wind knocked our basket around for a bit—“mind!”

I held her tightly, enjoying the contrast of the ever increasing chill of the air and her constant warmth. We were currently a hundred feet or so above Ponyville, riding a dark purple hot air balloon being pulled by Surprise. The white pegasus had a three-cloud cutie mark (two blue clouds at the bottom, and one yellow one at at the top forming a loose triangle), something I finally noticed from this angle as she steered us towards a reserved cloud that was created for the date.

I was willing to bet Cheerilee never experienced an Amour Veil date. Like Gentlemen for Mares, the company started out from an idea; what if they could bring pegasi-exclusive cloud-dating experience to the unicorns and earth ponies? Apparently, a lot of ponies were pretty curious and the company’s been raking it in ever since.

Surprise was having a bit of a hard time steering the balloon as the North Wind had unexpectedly made its presence known, but she assured me that it wasn’t going to be a problem. After a few maneuvers, I finally saw it.

Equestrian clouds looked a bit similar to the Earth ones, though they always seemed to have fuller volumes, being thicker and fluffier. This one was artificially set up, giving it some interesting contours around the edges, as if made into a fence, along with a few mounds to use as seats or recliners. In the center, though, it was made flat to accommodate its guests.

Surprise was finally able to land the balloon on the edge of the cloud, formed like a dock, and began the tie-up procedures.

“Okay, let me take care of this bad boy,” Surprise mumbled, having a length of rope between her teeth. She began to scramble around the cloud, and a few moments later, I could hear her again, quite clearly, “Alright, warming potion is the orange one. Cloud-walking potion is the light-blue one. Both are in the picnic basket.”

I was already ahead of her, having used Amour Veil for quite a few customers already. Grabbing out a warming potion first, I handed the vial of glowing orange liquid to Cheerilee, who looked at it, and at me, apprehensively. I raised my vial, touching hers gently, before I downed it. She followed a moment later.

Swallowing the liquid, I felt a burst of heat blooming from the center of my body going outwards. The north wind was present, but somehow, its chilly embrace was mitigated, transformed to nothing more than a slight cooling sensation.

I still shuddered, though, and this time it wasn’t because of the wind. Potions and the like were something of an ‘acquired taste’ for human beings. Apparently, we didn't have the capacity to break down and digest ingredients of magical nature, leading to some unexpected... side-effects for first time potion drinkers. Heck, my first warming potion turned my hair fire-orange for a day, how weird was that? Thankfully though, human constitution allowed some form of adaptability, and with continued drinking, the side-effects would diminish until no longer present.

Yet, I was still nervous.

“Okay... that was my first warming potion. It was, uh, interesting,” Cheerilee declared as she handed her vial back to me.

“Not as interesting as my first time, believe me,” I replied, grabbing another vial of light blue liquid. “One more to go, Cheerilee.”

The mare nodded and after another set of vials done and over with, I made sure Surprise gave me the okay before I unlocked the hatch of the balloon basket, and slowly guided Cheerilee onto the clouds.

It wasn’t a new experience, walking on clouds, yet the first step always threw me off. Picture yourself stepping barefoot on a thick memory foam mattress – that was how it felt like. It was the weirdest, and oddly, the most comfortable thing your feet will ever step on.

Cheerilee, judging by her soft yelp on her first step, agreed readily with my sentiments.

“Ooh, that is odd!” she confirmed as she took another step, then another. Four hooves on the cloud, she jumped up slightly, giggling as she sunk a bit on landing, but was kept afloat.

There was a rustle of wings as I spotted the white pegasus joining us, smiling warmly. “Okay, balloon’s secured. There are a few flare-gems in the pouch of the picnic basket. You know how to use them, right?”

I nodded.

“Okay, then. Red’s for emergencies and blue is for pick-up,” the pegasus said before pausing and subtly elbowed my leg, giving me a wink. “Enjoy your stay.”

I watched as Surprise left by doing a swan dive off the cloud. I chuckled, finding her quirkiness a welcoming experience. Most ponies I met during my dates regarded me and my companion mare as the most unusual sights they had ever seen. While most kept their gaze professionally neutral, a few were more negatively inclined.

Surprise just showed, uh—well, surprise?—when I showed up at her stall with Cheerilee in tow, and gave me the most supportive smile; first I’d seen, compared to the usual reactions.

It was utterly refreshing.

“Mister Wingman?”

I looked towards Cheerilee, who regarded me with some curiosity. I knelt down on one knee again and gently kissed her cheek, and continued giving out smaller pecks down her neck to her shoulder. Cheerilee just stayed still, shivering and cooing with satisfaction as my lips traveled through her coat.

“Help me set up dinner, gorgeous?” I asked gently. She looked at me, blushing once more before nodding.

The sun was slowly setting when we finally finished arranging our spread. Cheerilee set up the cloth over the cloud and handled the plates as I unpacked them from the big picnic basket. There were some vegetable-sandwich platters, some bowls of salad, some fruits and also a small chocolate cake with a nice red heart drawn on top.

We sat down, just in time to see the orange blaze sink into the horizon, and watched as the light blue sky was slowly overtaken by the velvet blanket of the night sky, filled with glittering stars.

“Oh, my,” was Cheerilee’s reaction as the night sky showed us its beauty. One by one, each house in Ponyville began to glow with warm yellow artificial light, reminding me of immobilized fireflies, contrasting wonderfully with the cool blue sparkling light of the stars.

“It’s beautiful,” she finished.

“As stunning as the mare with me,” I replied. I felt Cheerilee nudge me gently on my shoulder.

“Oh stop it,” she replied with a whisper. “I know it’s your job to take care of me and all, but you don’t have to pretend.”

I looked at her for a moment, losing myself slightly to her green eyes before I moved my hands down her neck, smoothing her coat.

“I am not pretending, Cheerilee,” I declared with absolute finality. “I have been paid to accompany mares on dates or to their beds, but I’ve never been paid to speak my mind. So” – my hands went down to her forelegs and gently grabbed her hooves, bringing them up to my lips – “when I say you are absolutely stunning, I mean it.”

Each of her hooves received one peck before I released them.

Cheerilee looked absolutely lost. Her blush went increasingly crimson, but her eyes wandered, looking at me, shaking with uncertainty. She stayed like that until I spread out the plates and handed her a tomato omelet sandwich and a small bowl of greens.

“Why can’t stallions be like you?” she whispered, as she took her platter. I could hear the strain of emotion in her voice. “Why do you have to be a hired human? Why did I have to be in heat?” Her voice suddenly regained volume and anger. “Why now, of all times!? What took you so long!? And why did I hire you in the first place?! I was happy with everything, and you... you! You come in and sweep me off my hooves pretending you’ll still be here by tomorrow!”

She dropped her plates, making the blanket and cloud under it sink a bit before it reformed. I saw her eyes closing, moistening with tears as she shook her head.

“No!” she declared. “You’re like the rest of them. You must be pretending. It’s your job to.”

I took her accusations head-on, unflinching. I don’t know whether her anger was a product of her failed relationships or her own low self-esteem that has festered over the years, brought about by a somewhat too intrusive human escort and her heat, but I hit a nerve somewhere and it was all finally pouring out.

I calculated the effect of my next words. I’d finally get through to her... or she’d buck me out of the cloud. And it was a long way down.

“Cheerilee, I love my job,” I said softly. I kept my hands to myself. Now was not the time for touchy-feely. “It wasn’t quite what I wanted when I arrived in Equestria, but I learned to love it all the same. And judging from this morning, you love your job too, right?”

There was something frightening behind her now smoldering gaze. She had the aura and face that read ‘Choose your next words carefully’ behind them. How far was I from the edge of the cloud? I was sorely tempted to check.

“When you teach your students something, does it bring joy to your life... or do you just pretend, because it’s your job?”

She took a step towards me, her eyes never changing, and her lips narrowing to one of the thinnest lines I have ever seen. I silently swallowed and just sat there, facing her. She stopped just shy a few steps, staring. I felt a shiver run through my back. I began to expect the worst as she leaned forward and...

It was a kiss—a simple kiss on the cheek. It almost made me jump though. That doesn’t say anything about my bravery.

Nothing. At. All.

“You really remind me of him,” Cheerilee whispered as she stepped away. I grabbed her right foreleg before she could go any farther.

“I remind you of whom?” I asked.

Cheerilee just looked at me for a few seconds, her expression giving me an idea that she was either reminiscing or thinking about something quite deeply. Then, she really looked at me.

“Prove it, Mister Wingman.”

I cocked my head to the side, confused. She just gazed at me in an encompassing seriousness.

“Prove it to me that it’s not just empty words. Prove it to me that you mean what you say.”

I stared at her for a second, before I brought my lips to the base of her hooves, much to her surprise. She told me to stop and that it was dirty, but I paid no mind. I kissed her hoof, feeling the sharp biting cold of steel of her horseshoes.

“These hooves, delicate yet strong,” I declared.

I then approached her, letting my lips climb up her leg to her neck. I kissed her throat, enjoying her silent groan escaping her lips.

“Your neck, slender and straight.”

I climbed to her cheeks, giving them a peck and a deeper one to her forehead.

“A mare of beauty and smarts. Irresistible.”

I delicately began kissing her mane, my free hand moving towards her tail. It twitched as I ran my fingers through it.

“Soft and silky, with a hint of sunflower.”

When I began kissing her shoulders, back and side, I could hear her breathing shallowly. I smiled.

“Muscular tone, strong, yet feminine. Musk mixing with wood—provocative.”

I kissed her flanks, more specifically, her Cutie Mark.

“The symbol representing your compassion, your dedication and your kindness.”

I began my descent down her hind legs.

“Full hips, strong legs. Seductive.”

“Oh, Celestia! P-please...” she finally spoke, moving her hindquarters a bit, hoping I would continue my trek – but no. I rubbed her body, letting my lips travel forwards, hearing her grunt her complaints before I cupped her cheeks and looked at her eyes. I smiled.

“A mare of compassion, beauty, and brains—you, my dear Cheerilee, are beautiful,” I finished, and let my lips touch hers.

She pinned me to the cloud (luckily away from our picnic spread) and began to dictate the kiss, clambering over me and let her tongue explore me as I felt my cheeks moisten. In the corner of my eye, I saw her crying.

As our lips separated, I saw her desperately try and cover her green orbs with her forelegs. My hands rubbed her neck and gently pulled her down to my stomach. She complied easily, setting her full weight upon me, making the cloud embrace and surround me as she wept and hiccupped.

An evening shower, I thought. It didn’t put a damper on the beauty of the night – nor the beauty of this mare.

We stayed there for a moment. I enjoyed her warmth and the view of the night sky, while Cheerilee slowly began to settle down. Her whimpering finally died down, and I could feel her hooves encircle my stomach before she began to pull herself up. Her moist green eyes met mine.

They blazed with desire.

“Take me, Wingman,” she declared. “Now.”

She didn’t even wait for me to move. She clambered up my body, her coat prickly even through the fabric of my clothing as I groaned slightly, feeling it brush through my groin. Her eyes never wavered, looking straight at me as her lips finally reached mine, and gave me a wet, hungry and very hot kiss.

I kissed her just a second before giving her my cheerful reply, “No.”

Cheerilee blinked. A few seconds later, her eyes narrowed.

“W-what?”

I shook my head. “I want this to be special for you. And making love under the stars may seem to fit the bill, but we both know you’re being influenced by your heat. Besides,” I looked towards the yet untouched food placement nearby, “we still have to eat dinner.”

Cheerilee looked at me and then towards the basket. She looked back at me once more.

“You know,” she began in a deep throaty voice not unlike Eve’s. Oh wow. “I have you pinned down. I can do anything to you. And you’re going to enjoy it.”

Oh, God. She was getting sexier by the minute. But no. Not yet.

“I’ll tell you what, Cheerilee,” I replied, my voice getting a bit hoarse, “if you hold off until we get to your room, I will,” I kissed her, “make love to you,” again, “as long,” and again, “as you want.”

I felt her shudder. I saw her eyes glimmer at the prospect, the promise of ultimate satisfaction.

“Can you deliver?” she asked, heat emanating from her voice.

I just smiled.

Cheerilee slammed the door behind her as we entered her house. She was getting frazzled, and I could smell her musky sex in full force once more. She moved ahead of me and I spotted her tail twitching, lifting, always exposing her very wet, very puffy, and very ready marehood. Hell, when she turned to look at me, her eyes smoldered with impatient desire.

“Now.”

Okay, she devolved to cavemare speak. I just stared at her, standing straight and as confident as I could.

“Wait in the room Cheerilee,” I ordered.

“No. Here. Now.”

“Cheerilee, if you don’t go to your room and wait for me, I’m going to leave you like this,” I advised her, sternly.

She shivered and whined a bit, but nodded all the same. I never saw any other earth pony move faster.

Now that she was gone, I began move towards the kitchen, while at the same time removing my sweater, shirt, and loafers. By the time I reached the kitchen, I was working on my pants and underwear. The warming potion could still be working as I didn’t feel the biting cool air. Or maybe I just couldn’t feel the cold because I knew what was about to happen.

I grabbed my small shoulder bag and scrounged for two vials filled with clear golden liquid—Magical Boosters, or as I’d like to call them, Magic Viagra. I never understood how it worked, as magic was always a bit of a mystery to me, but it was, at least this mixture, supposed to increase stamina and boosted fluid production. It also had a nice effect of shortening the refractory period between coitus, allowing more increased performance.

Wow, would you listen to me? I sounded like some sort of sex ad salesman.

I opened the vial. I hesitated, realizing that this was going to be the first time I ever drank a booster and I didn’t know what the side-effects would be.... but I remembered there was a mare waiting for me in her room, and a promise I made.

I drank it.

When I opened Cheerilee’s door, I began to feel its effects. It had a similar effect to the warming potion, but it didn’t convey just one singular feeling throughout my body. I felt stronger, as if my muscles brimmed with combustive energy, springy and ready for action. The usual tiredness I usually felt near the end of the day began fading, as if I had gotten a good eight hours sleep for the past minute. And when I saw her, I felt a primal force of lust overriding my thoughts.

Cheerilee stood there, forelegs at the edge of the bed as she raised her hindquarters, elevating her flanks and hips invitingly in the air, her tail cleared out of the way to show me her wonderful wet lips. She turned her head a bit, looking at me, smiling.

I smiled back.

I knelt behind her. I kissed her. She moaned as I felt her pink feminine folds wink as more fluids began to excrete out, dribbling out and down towards my chin. I held her hips with both my arms as I licked, enjoying her walls trying to trap my tongue inside it.

Yeah, good luck with that.

I spanked her flank gently as I finished my kiss and heard her moan. I let my erection touch her slit. I didn't enter. Not yet. I just leaned forward and whispered near her ear, “Cheerilee, as promised. You’ve been a good filly and good fillies deserve a reward. I’m going to apply everything I learned, all the positions taught to me. I’m going to make sure that you. Will. Be. Satisfied.”

She whimpered. I couldn’t help but smile.

“Let’s start with something simple. You ponies call it missionary. I call this... level one.”

And I thrusted in. I grunted as her folds received me with enthusiasm and began to fold and twist around my manhood. I might have been imagining it, but this felt more intense than the first night with her. Cheerilee herself was now lost in her own moans as her front hooves began to grab on whatever it could to steady herself.

I didn’t pace myself. She wanted it – wanted it really badly. So, I went in as fast and as hard as I could, buckling as I felt myself explode inside her, filling her up as much as I could. She screamed with satisfaction.

I extracted myself and pulled her deeper in her bed’s embrace. I felt a bit of numbness around my hips, but my hands worked on her, touching her, massaging her gently. I let my lips kiss her coat, sides and shoulders. I whispered, truthfully, on how lovely she was.

I was ready again in a minute, the numbness fading from my manhood as it was erect once more. Just in time, too, as Cheerilee herself looked ready for another bout.

“This is called the cross,” I declared as positioned her on her back. I positioned myself perpendicular to her, lifting her legs over my hips, her welcoming walls at level with my hardness. At this position, I could see her face, the one filled with excitement and anticipation that transformed to lustful joy when I entered. I felt my hips increasing pace as her face scrunched with increasing pleasure of the actions I wrought.

Each time I ejaculated, I’d kiss her; remind her of everything wonderful I found within her. I licked and sucked her naked hooves and her swollen teats. I licked her neck, kissing her lips. I did everything I could to allow myself a few minutes to recover before I switched to another position.

I explored the many variations of the belly-to-belly (human missionary) positions, some manipulating her legs as much as possible to hit her at every angle as I could. Then, I began to explore the more exotic positions – The Scissors, The Wheelbarrow, and the like. At one point she became more active as she wanted me on my back.

Her mix of confidence and dominance made her a joy to watch as I taught her the more various positions for the Cowgirl (it was a little different from the human version, but the general positioning was the same). I watched her from below, as she looked down at my eyes as rode she me multiple times, her face transforming every time she made me orgasm.

It was one of the many highlights of the night. And there were many of those. Hours became nothing more than grunts, sloppy kisses, embraces and fighting tongues. Our throats increasingly tightened, notching our voices to a husky finish.

How many variants or positions did we do that night? Use your imagination. We certainly did.

The finish was slow and intimate. I sat, cross-legged, back on the headboard of Cheerilee’s bed as she positioned herself, facing me. Her forelegs rested easily on my shoulder as she straddled me, letting her hind legs encircle around my hips in a modified Lotus position as I entered her.

I kept kissing her as much as I could, whether her neck or lips or cheek. I would grunt with satisfaction with every upward thrust, signaling to her that she was rocking my world. She did. And she loved it.

“Oh, Cheerilee,” I moaned as I felt the building pressure. “You wonderful, beautiful, bewitching, lustful, magnificent mare,” I almost shouted, each adjective coming out breathless as I pumped faster.

“Oh, Celestia yes! Yes!” she screamed, moving her hips faster as well.

I let my left hand cup her cheek and I made sure I let her watch me as I came. Half my eyelids covered my sight as I grunted loudly, thrusting my hips upwards. I wanted her to see her effect on me. I wanted her to see what she has done to me.

I wanted her to see the beauty of her work.

Her marehood swallowed my whole length and I jerked uncontrollably as her walls began to squeeze out anything I could offer at this point. I finally felt drained. I collapsed and would have been on my back had it not been for the headboard supporting me up as I let my arms fall at my side, lightly caressing her flanks.

The last thing I felt before I blacked out was a gentle kiss, and a whisper of thanks.

I woke up, feeling the warm light of Celestia’s sun on my skin, and immediately grunted with pain as I felt like my head was being squeezed in a vice that was carrying a bowling ball in the tow. I was also surprised by the numbing soreness of my muscles, aching as if I had run a marathon.

Well, thinking about last night, I guess I probably did.

I blearily looked at my side and saw Cheerilee sleeping peacefully on my side, her forelegs embracing my left arm, her face glowing with satisfaction and pleasure. I couldn’t help but smile. I tried to extract my arm, but her grip on me was a bit too strong. I sighed and added some more effort in disentangling myself from her, only to feel the grip increase, making me realize something.

She was awake.

“Don’t leave,” she said. Her eyelids opened, revealing her green eyes as she held onto me tightly. “Please don’t leave.”

I frowned. “Are you in another phase?”

She shook her head. “My heat phase is gone. But I don’t want you to go,” she choked out.

I smiled gently and remained with her. I let my free arm caress her foreleg and neck. “I’m sorry, Cheerilee. But I have to.”

“You made me so happy,” she cried, her eyes moistening. “You made me feel... beautiful.”

“I didn’t make you feel anything. You were beautiful all along,” I replied. I carefully wiped the tears from her eyes with my thumb. “Never, ever, let anyone tell you differently. You are a strong mare. And you’ll be alright even without me.”

“You sound just like him,” Cheerilee sighed.

That was the second time she said that. I got curious.

“Who?” I asked.

“Sturdy Will,” she replied. “My teacher.” She paused. “My first love.”

I raised an eyebrow.

“I was... quite a silly filly. It was during the time when most of the teachers were still unicorns. He was the first Earth Pony teacher I met. He was”—she blushed—“big, muscular, strong, and carried himself with absolute confidence. But what made him special was how gentle he was. He made sure everyone had fun, and even joined us when we played.”

She sighed.

“One day, before our class graduated, I met with him alone. I poured my heart out to him, confessed my love.”

“He rejected you, didn’t he?” I asked, as gently as I could.

“Of course he did!” Cheerilee replied. “He had to! I was his student, and far too young for him! But...”

I saw where it was going. The first flag for a bad ending, huh? The first domino to fall.

“You doubted yourself that day,” I finished for her. “And it stayed with you.”

“It shouldn’t have!” the earth pony muttered. “I grew up, I moved on! But it was always there, that nagging feeling that kept saying I wasn’t... good enough.”

“You are,” I growled, surprising her with my anger. “Cheerilee, remember what I said yesterday. Remember the night we had. Do not doubt yourself, not after that.”

Cheerilee smiled a sad smile. “What if I forget?”

I grinned, showing little teeth. She shivered a bit as I made sure she heard every word of my reply.

“I’ll. Remind. You.”

Cheerilee then smiled. She closed her eyes. “Yes. Yes you will.”

We stayed there for a moment, enjoying each other’s embrace. Then, I remembered I was supposed to meet Eve at the edge of Ponyville. I also remembered something else.

“Um, Cheerilee, can you help me with my clothes? I think I left them all over the place.”

By the time I finally found my underwear and pants, I heard very hard knocking in the front door. It echoed violently inside my head, sounding like a stack of thick books dropping from a high place. For some reason, my head was feeling heavier and heavier. The numbness on my limbs didn’t fade either, with the pressing feeling of fatigue.

Man, it was a far cry from being the Energizer Bunny last night.

I heard Cheerilee opening the door as I finally found my shirt. I cringed when I heard a thunderous shout reverberate across the room, and worse, echo in my head like breaking china.

“Where is he!?”

Eve? Damn, girl needs to tone down the damn volume. I found my loafers, slipped them on, and made my way to the living room area.

“You better tell me right now, or I’ll—”

When I entered the living room, I saw her looming threateningly in front of a very confused Cheerilee, her horn glowing with a rather bright magenta aura, magic readily built up for release. When she saw me, her scowl in her face softened as the glow on her horn began to recede.

“What the hell?” I asked, raising my arms to my sides.

“You were damn late, that’s what!” Eve declared, with steel in her voice. “What took you!?”

“I lost my clothes,” I replied, putting on my cardigan.

Eve looked around, and saw the mess of the place. Her face stilled, and she grinned. She shook her head, and said, “I’m going out. Follow afterwards, or I’m coming back in and dragging you out.”

I watched her exit the house and rolled my eyes. I saw Cheerilee look apprehensively at the front door, and back at me.

“Who was that?” she asked, softly.

“My mother, apparently,” I replied with a snort. Ugh, damn, another headache coming. This day was starting to be irritating. “Don’t worry. She was just worried and she may have a busy schedule today. Don’t take it personally.”

“She was... very protective of you,” Cheerilee continued.

“She kinda is,” I chuckled as I made my way to the kitchen and made sure I grabbed the shoulder bag. I also produced my card from my pocket and began to sign my call name. Once I exited the kitchen, I saw Cheerilee now standing behind her front door, as if half-wanting to block my way out of the house.

Cute.

I approached her and handed her my card. She grabbed it with her hoof. “A reminder,” I said. And I gently kissed her forehead. She sighed and nodded. With a gentle kick, she opened the door, revealing the bright morning of Ponyville, with Eve and the chariot waiting for me.

“I’ll remember,” Cheerilee declared with confidence. “Goodbye, Wingman.”

“Take care, Cheerilee,” I replied, and began walking towards Eve. She met me halfway.

“I saw the house. Nice going stud,” Eve declared. “Do you leave all your customers’ houses in such a state? No wonder you’re climbing up the ladder.”

I chuckled. “That was her doing. But you should have seen her room.”

“Yeah, no. Don’t want to hear about it,” she replied. I only chuckled again, only to wince as another sharp pain registered in my head. I stopped half-a-step, wincing as my hand automatically went to my forehead.

“What’s wrong?” I heard Eve asked, worry evident on her tone.

“I drank two, maybe three boosters,” I advised.

“First time to drink that type of potion, right?”

I nodded.

“It could be manifestation of the side-effects. Let’s get you home then,” she said. I felt a hard nudge on my side as Eve began to walk with me, her warm body supporting my weight.

Climbing the chariot ramp was more difficult than expected, but once we got in, I sighed as I made my way to the chair. I closed my eyes and felt something touch my head. I glanced aside with one eye and saw Eve feeling my forehead with her hoof. I also felt the air stirring as I heard the telltale sound of wings flapping.

“Give Miss Cheerilee preferential rate status,” I said. I saw her blink.

“She’s a first time customer. That’s pretty rare, especially for you. Not only that, she was the mare that got you to drink a booster,” Eve advised, sounding a bit confused. “What, did she call you some weird nicknames you found oddly special? Like ‘shmoopy doopy sweetie weetie manly pie’?”

I snorted again, making my head hurt even more. Damn it, I should really stop doing that.

“Oh, God, no. That would be absolutely horrible,” I chuckled through the pain. My head may have hurt, but trying to imagine hearing Cheerilee say that to my face would have been...

Words can’t describe.

“So, what makes her special?”

I smiled. “Nothing really. She’s a teacher in Ponyville.”

And that made her special.

Author's Notes:

I wanted this one out for before the New Year. Consider it a Holiday Gift to all of you.

Thanks to coandco, murphy, grey conscience, and finally shira for going through this with me. If anyone comments on the quality of the fic, know that its because those guys really helped me along the way.

Happy New Year to you guys, and enjoy the story.