How would one deal with being attracted to one’s friend?

That was the question on my mind ever since that night, while I was warmed by her embrace, electrified by her kiss. Eve had admitted her feelings to me, whispering it when she thought I was asleep, inebriated by good single-malt scotch.

The admission changed things. No, more accurately, it changed my perception of her. One day, she was just... Eve, my friend. Now, she’s Eve, my friend, who is also a very good-looking unicorn and has feelings for me.

Looking at her now, pink mane, vivid green eyes behind her cat-eye rimmed spectacles, white well-brushed coat, and beautiful hips and neck, she was a mare that could distract anyone passing by her. Human or stallion.

It wasn’t as if I didn’t think Eve was attractive before, though. It just wasn’t something I really focused on. For the longest time, she was my friend, my very best. She was the one that found me when I first got to Equestria, was the one who took me in when I struggled.

However, her confession had me thinking more about the nature of our relationship. Was it possible to expand our friendship, to become something more? We’d made each other laugh and we’d comforted each other on more than one occasion. I had been in a relationship that didn’t even start as solidly as that—all I saw was boobs and said yes.

So the question popped into my head: could Eve and I work?

I didn’t find the answer. Neither that night nor afterwards. When I had woken up the next day and saw her again, it was as if the status quo remained unchanged. She was my friend once more, slowly becoming my Handler as my leave expired. She never really brought up that night again.

Quite frankly, part of me didn’t want to, either. I mean, considering what had happened to me the past few days, could I say that I was ready for a relationship? And even if we ignored that, what would happen if that relationship... failed?

“Sometimes, you have the most fascinating facial expressions,” Eve said.

I blinked, then looked at the mare in front of me once more. I shook my head, trying to focus on the present.

“Something wrong?” she asked.

“No,” I replied. “A little nervous, maybe. First time on a job since my leave.”

A slight smile chinked the professional expression on Eve’s face. “Why? Its not like you’ve been gone that long. It’ll be like—what’s that human expression? Riding a bike?”

I grinned. “Yeah, like riding a bike. But it's not that. I mean, I know who my client is. And I’ve never entertained an Element before.”

“Yes, well, that’s no reason to be nervous,” Eve said. “I mean, yes, you are about to service an Equestrian Hero, and if she says anything about you, it’ll either make or break your reputation.”

“Well, that’s reassuring,” I replied, rolling my eyes. “I can already feel my nervousness fly away with your assurance.”

“Oh, shush,” Eve said. “What I’m trying to say is that she wanted you specifically. You shouldn’t be nervous at all! Get excited! Use your head, make her happy! Treat her like how you treat your regular customers! What?”

I regarded her for a moment. She was giving me a wide smile, blinking way faster than normal. “You’re nervous too,” I said.

Her mouth opened. “Wha—? No, I’m not. What gives you that idea?”

I raised an eyebrow as a reply. She stuck out her tongue at me in response.

“Fine, fine,” Eve muttered, crossing her forelegs. She pouted. Damn, she had a cute pout. “I have the right to be. You’re my Gentleman, so whatever happens, it’ll be on me too.”

“Yeah, well, I’ll try not to disappoint,” I replied, winking. “After all, can’t have you thrown out of your fancy apartment to starve in the streets, right?”

Eve lowered the tone of her voice, going full Audio Erotica. “That won’t happen because you’ll take care of me, won’t you Harry?”

I suddenly remembered her warm embrace and her electric kiss. I felt my stomach take a dive as I opened my mouth, then immediately closed it.

Eve must have sensed something wrong because she immediately frowned. “Harry, are you okay?” she asked in her normal voice.

I took a deep breath. Damn it, Harry. Calm down. Not trusting myself to speak yet, I just gave her a nod.

Eve looked at me. “Maybe it was too early to have you out there again,” she said. “Maybe we should cancel the appointment.”

I immediately shook my head. “No.”

Eve frowned. “You sure?”

“Yeah.” I nodded. “It’s just nerves. Plus, you know, stuff. Still reeling from the news on how Sal is now exclusive to that High Duchess.”

“High Duchess Gilded Spiral, yes,” Eve replied, nodding.

“I never thought that Exclusivity Clause would ever be used,” I muttered. “You know how expensive that is?”

“Well, when you’re in love,” Eve said with an odd tone.

“So, it’s true? Sal and Gilded Spiral?” I asked.

Eve nodded. “And it makes sense, too. If Sal broke his contract with Gentlemen for Mares, it would have cost the High Duchess a lot more. Now, she can have Sal all for herself while waiting for his contract to expire.”

“And here I thought Equestrian ponies were all about sharing.”

“When you’re rich enough, I guess,” she shrugged. “I mean, take a look at a certain Princess of the Crystal Empire. Plus there’s always that romantic notion of keeping a stallion for yourself. Or at least, be the First Mare, who gets most of a stallion’s attention.”

“Like The Knight and Stallion, right? Which reminds me, any chances I can borrow the books I haven’t read yet?”

“Sure, no problem,” Eve said. She paused for a moment. “Harry, do you remember our talk the night you stayed in?

“I wish I was the mare that would challenge you.”

I swallowed. “W-what talk was that?”

“The one about you leaving Gentlemen?” Eve replied.

I nodded. “Oh yeah. What about it?”

“If you’re going to leave, then maybe taking an Element as a customer would not be wise,” she said. “Especially this one. If she likes you, and if she talks about you, your already growing list of clients will most likely double. Maybe even triple. She has been known to set trends now and again. You could be that next trend.”

“Well, I’m not leaving in the near future,” I replied. “I honestly don’t know what else to do right now, other than being a Gentleman. I’ll be looking out for opportunities, but for now, I’m going to do my job.”

Eve looked at me for a moment before nodding. “Okay. Just... remember, Harry. I’m here whenever you need me.”

I smiled. “I couldn’t ask for more.”

“Of course you couldn’t,” Eve said. “I’m the only thing you’ll ever need.”

I swallowed once more, a bit uncomfortable. Another thing I’ve been noticing was the way Eve chose her words, which with her confession, opens up new kinds of interpretations. Sometimes, I even wondered if Eve was doing it on purpose.

Thankfully, she didn’t notice my discomfort. Instead, her attention was on the newspaper she was magically picking up. I guess that was the advantage of enclosed chariots: no roar of the wind to shout over or fear that it would grab your reading materials from your hands. Or hooves. Or magic, in Eve’s case.

I found myself wishing I’d brought my own reading material, but I made do by taking a look outside, through the chariot’s opening.

The sky was slowly taking on a red tinge, signifying the nearing end of the day. I was not to meet Rarity, my client, until after the sun had set, but this was going to be my first time in Hollow Shades. I wanted to scout the area first, see where to set up the dates, and maybe try and see what unique services were offered in town.

I looked at Eve, half-wondering if I should ask her if she was knowledgeable on anything in regards to Hollow Shades, when I noticed the front page talking about...

“Changelings,” I said.

Eve folded the newspaper, looked at me for a moment before she folded the paper to get a better look at the front page. She frowned. “Yes. Changelings.”

“Weren’t they that race that fed on emotion?” I asked. “Tried to conquer Equestria years before the portal was opened?”

“Yes on both questions,” Eve replied. Her frowned deepened. “We haven’t heard from them since then. And now, this was the second Changeling we found dead in Equestria within the week.”

“I’m assuming you guys aren’t the ones killing them,” I said.

Eve raised an eyebrow. I chuckled.

“Okay, so who’s killing them?”

Eve shrugged. “I don’t know, and it doesn’t matter.” She folded the newspaper. “Changeling news is causing old fears to resurface. Princess Celestia is now trying to raise awareness and I won’t be surprised if the company starts drafting new security procedures soon.”

“Heh, I wonder if it’ll be like the Dominion Wars,” I said.

Eve looked at me blankly. “What’s that?”

“Its from a TV show, Star Trek,” I explained. “They used blood screening to make sure everyone was who they said they were. Was wondering if you guys were going to do something similar.”

Eve giggled. “Yeah, except instead of extracting blood, we’ll use magic to detect Changeling mimicry. Far less needles.”

“But the needles is the exciting part!”

“Well, if you insist, I can always tell Platinum that you rather prefer getting stabbed by needles to prove your identity,” Eve said. She wiggled her eyebrows. “Is that a thing for you? Like Jonas?”

I blinked. “Are you seriously comparing me to the guy who wanted to use ‘Caligula’ as a call name?”

“Well, if the horseshoe fits...”

I replied by sticking my tongue out at her. Her giggles became louder.

“Seriously, though, you shouldn’t worry about this,” Eve said. “You should just concentrate on your client. I mean, do you have a plan ready?”

“I’m forming one.” I looked at Eve. “Are you familiar with the sights of Hollow Shades?”

She took a moment before shaking her head. “Hollow Shades isn’t exactly a big city or a prime tourist spot. It has an interesting history, though. It was formed by a few ponies that were dedicated to Princess Luna before she was overtaken by the Nightmare. They wanted to build a city where the night lasted longer and did it by building the town inside Shady Forest, which itself was unique because the Forest seems to naturally block or absorb sunlight.”

“Any other unique facts about it?” I asked.

“Well, during Nightmare Night, it reaches its peak number of visitors,” Eve answered. “Oh, and the locals favor traditional captured fireflies compared to magical bulbs as far as lighting goes. I mean, they do have bulbs and some modern Equestrian conveniences, but they are very particular in using fireflies as a source of light.”

“That is unique,” I admitted. “But completely useless.”

Eve chuckled. “You’ll get by.”

I wish I had such strong faith in me. In truth, Rarity stumped me as far as mare customers go. Even if I disregard her status as an Element, she seemed to be pretty knowledgeable about Gentlemen.

I mean, even new clients who were recommended to me by my regulars still showed some gap of knowledge and harbored presumptions. Rarity knew how our call names were designed to roll with Pony name-theming, which in itself was not something we advertised.

If something so subtle was known to her, what else did she know?

Of course, I took that as a positive. After what had happened in Neighagra, I’d rather deal with a pony who knew what she was getting into, who knew what I was, and who still accepted me enough to hire for the night.

Then again, her knowledge would make it harder for me to entertain her. Plus, she was an Element of Harmony, a national hero; and considering how sophisticated she carried herself, she was probably quite experienced in the high life. And with nothing much to go on in Hollow Shades, I’d have to rely on my skills on sweeping mares off their hooves.

Still, I was confident I’d pull through. I was a great believer in the school of thought that entertaining a mare was nothing more than finding a connection with her. The fact that I had the advantage of meeting her before and having talked in a capacity meant I wasn’t going in cold. She carried herself as a proper lady—at least, proper in terms of Equestrian culture, and would most likely expect the best, whether during the date or after.

It was time to bring the A-Game, Wingman.

“We’re here,” Eve said.

I looked outside the window. The chariot was slowly descending, and the first thing I noticed was the immediate darkening of the area. The sky was still red, but for some reason, the intensity of the sun was muted to just barely visible.

The chariot pegasi were good at their jobs; I barely felt the wheels hit the ground. As we finally came to a full stop, I felt for the door handle and opened it, revealing the town to me for the first time. Houses were seemingly carved out of trees, lit by soft-glowing lights. The cobblestone roads were rich with street lamps that contained fireflies inside. They glowed with an intense yellow light before dimming at certain intervals, then brightening again. The rest of the lighting came from the numerous fireflies that flew around town, landing on grass or trees, or even by hitching a ride from other ponies that walked around.

I spotted a few modern establishments, judging by the use of modern signs and light bulbs, but they still tried to fit in with the rustic aesthetics, using soft glow yellow lights and well-dressed maitre d’s. Still, the lighting looked a bit artificial, but considering the number of patrons inside, it seemed that the locals didn’t mind.

I heard a familiar clip-clop sound and spotted a pony-pulled open-roof carriage passing by the chariot. It was well made, polished and gleaming with dark shades of red and black. The earth pony pulling it had a pair of prop bat wings attached around his barrel.

I stepped out the chariot, drinking in the sights before me. I even took a deep breath, the smell of wet earth dominant in the verisimilitude of scents: freshly baked bread from a nearby bakery, crushed basil with a nutty, buttery tinge, and a familiar honey-floral scent.

The last bit caused me to look to my left. Eve was leaning forward, her snout almost touching my cheek as she too took a look outside. I just... stared at her for a moment as she scanned the town, whistling afterwards.

“Wow,” she muttered. “It’s like Nightmare Night. Did you see that carriage-puller’s bat wings?” She pointed her forelegs towards the one that passed by. She smiled. “This town seems fun to visit!”

I couldn't keep my eyes off her, so I settled on smiling as well. “We can always come here again once we have free time.”

Eve looked at me for a moment, confusion evident in her face. That’s when it hit me that my statement wasn’t as innocent as I had initially thought. Part of me wondered if I had opened Pandora's Box, and if I had thrust myself into something I wasn’t ready for.

Yet as much trepidation as I felt, a part of me felt... curious on her reply. So, I held my breath for a moment, keeping my face neutral as Eve slowly smiled and nodded. “Why not. I could use a break too.”

I breathed a little easier. “Thinking of getting ‘suspended’?” I joked. I received a gentle bop to my head for my troubles.

“I thought we were over that, Harry?” Eve mock complained, raising the pitch of her a voice just a bit to give that ‘whiny’ flavor. “You’re never going to let me live that down, are you? I misspoke, Harry. Misspoke!”

“You scared the crap out of me, that’s what you did,” I replied. I tried to be deadpan, but I couldn’t help but chuckle. Eve joined in as well.

“Fine, Harry. I’ll get ‘suspended’ too, if it’ll make you happy.” She looked at the town again. “Okay, if we’re going to visit this town again, you need to find any good places where we can eat. And maybe something fun to do here.”

“Well, I’m going to do that anyway,” I replied, looking at the town again. I took a breath. “Well, yonder I go, stepping to and fro.”

“Where did you get that?” Eve asked.

I looked back at her with a smile. “My brain.”

“No wonder it sounded stupid.”

I stuck my tongue out at her. “My genius is never appreciated.”

“Well, Starswirl, get your unappreciated-genius rear out there and earn your pay,” Eve replied, giggling. “Good luck.”

I turned around, waving my hand. “Never needed it!” I declared. I heard her giggle one last time before the chariot door slammed shut. By the time I walked a good moment away, a whoosh of air blew around me and I spotted the chariot take off towards the muted red skies.

I watched the chariot disappear before I moved forward, wasting no time. A good chunk of the next hour was spent on scouting restaurants, reading menus, and taking a close look at the ambiance. The rest, I spent on finding a few more things I could use on my date, and spreading a few more bits around to make sure everything went smoothly.

There was nothing more off-putting than when a date gets delayed because someone forgot to pay the bill. And I would know. It happened to me—only once, though.

After I went over my date plans and checked the pegasi weather schedule to make sure there wouldn’t be any problems there, and I made my way towards the Amaris Inn.

It was a rather fashionably built building that chose to forgo the local aesthetics. Instead of looking like a building carved from a tree, it was a solidly-built rectangular establishment made of wood and stone. While the design wasn’t as grandiose as the ones from Manehattan, it looked luxurious compared to its surroundings, with its smoothed walls, smart color scheme of blue and white, and bright bulbs that lit the area. Yet, as different as it looked, it somehow still blended well with the town’s image. Maybe it was the trees that seemed to surround it, or maybe the numerous fireflies that roamed the area. Whatever it was, Amaris Inn looked like a good place for any visitor to stay as they enjoyed the local sights.

I entered, greeted by quite a large group of ponies that looked at me in surprise. A few moved quickly away as I made my way towards the stairs, and slowly climbed to the second level, going to room twenty-three.

Before I knocked on the door, I took a moment to look at myself using a nearby wall-mirror and made sure there weren’t any creases on my black suit and pants, both made by Rarity herself.

They were simple yet elegantly designed pieces of clothing that not only blended well with my collared white shirt, but were also comfortable to wear. I adjusted the silver-gemmed cufflinks, something she also included in the package when the clothes were delivered to me. I was pretty sure I did not commission her to include that.

She wasn’t kidding when she had said she was generous. And I think I finally got the joke.

Once I was ready, I knocked on the door thrice, took a deep breath, and closed my eyes for a few seconds. When I heard the metallic click, I opened my eyes.

I was about to greet her, only for the words to be taken right out of my mouth. My brain suddenly shut down as I stared at the pony in front of me. It was definitely Rarity, judging by her off-white coat and styled long purple mane. But I guess I was expecting her to look like she did back when I met her in Ponyville.

Boy, was I wrong.

Rarity wore a very tight-fitting dress. It wasn’t of pony design, however, but a bit of amalgamation of the human style with a pony body. The collar was bare, almost absent, which exposed a healthy amount of her beautiful neck. There were barely any foreleg sleeves. Most of the layers were concentrated on the barrel, which complemented a lot of her features, ending with a loose skirt towards her rear, with a high cut slit that barely exposed the bottom gem of her cutie mark.

“Good evening, Mister Wingman,” Rarity greeted, moving just slightly towards the side. Her actions emphasized the curves of her rear, and with the way the dress was cut, it affected me more than if she were unclothed.

I could only stare. “I, uh...”

I heard Rarity giggle, and that snapped me back to reality.

“Darling, are you okay?” Rarity asked. “You seem to be quite... distracted.”

My eyes took one last look at her well-curved rear before going towards her face. That’s when I noticed that she also worked on her make-up and mane. She sparkled. And no, I wasn’t being metaphorical. I didn’t know what she put around her eyes or in her mane, but she shone like stardust. I also noticed that her collar was actually a necklace made of red gemstones. To finish it off, she wore green gemmed earrings.

If anyone else wore something like this, I’d have called it extravagant. Not Rarity, though. Maybe it was because she carried herself so naturally that the gems, the make up, all complimented her, rather than detracting from her beauty.

“Good evening, Miss Rarity,” I finally said. I knelt on one knee, offered my hand, palm up. She easily placed her hoof on top of it, and let me kiss it gently. “I’m quite sorry for being a bit distracted. It tends to happen when there’s such a beautiful mare in front of me.”

Rarity blushed but remained composed. “You are quite forgiven, Mister Wingman. Though please, call me Rarity.”

“Then if it would please the lady, call me Wingman,” I replied back, smiling. I stood up, and motioned towards the hall. “Shall we?”

“Verily.”

I led Rarity down the stairs. Once I was at the foot of the stairway, I tried to keep my eyes away from her. I failed. All I could focus on was towards her well-formed rump that moved emphatically with every step she took. I have no idea if she was doing this on purpose, but I was quite sure that she knew I was looking. Every moment I looked at her, she had that small smile, as if celebrating a small victory, but didn’t say anything to dissuade or encourage me.

As I led her outside, her eyes widened a bit as she saw the carriage waiting for her. The puller had already opened the door and set up a small ramp, ready to receive us.

“Very nice,” Rarity declared, scanning the carriage and its interior. She looked at me, smiling. “Are we going far?”

I shook my head. “Not quite. But I felt that, since I'm new here, I’d rather have someone who knew their way around town take us around.”

“A wonderful idea,” Rarity replied, trotting up the short ramp. “I, myself, am quite new in town as well.” Before she fully entered though, her tail gently caressed my hand, just quick enough to tickle.

I looked up, noticing her tail was lifted. My brain translated that as she was exposing herself to me, interested, but the fact that she was covered had me reacting even stronger than when she wasn’t clothed.

She knew. Oh, she knew, giving that wink as she settled down in one of the seats. “I cannot imagine how the night will go if both of us get lost.”

“It would definitely be a novel experience,” I replied, my voice getting a bit ragged. I followed afterwards, gently closing the door behind me before sitting down, opposite her. The carriage-puller immediately removed the ramp and shortly afterwards, we were moving.

“I have never been on a carriage before,” Rarity said after a moment. When I looked at her, she was staring at me a bit, her eyes conveying some sensuality without being overt. “Well, at least not with a Gentleman.” She blinked, slowly, just enough to emphasise her long eyelashes.

I smiled. “I’m quite glad you’re enjoying the ride, Rarity. Though, I have a confession to make.”

She blinked. “Oh? And what would that be, Wingman?”

“The carriage ride is only so I could enjoy your beauty that much longer.”

The mare smiled. “Now, now. No need to exaggerate.”

I offered my palm again, and after a moment, she obliged. I encapsulated her hoof with my fingers, slowly bowing to kiss them. Twice. I looked at her again, giving her hoof an emphasizing squeeze. “I am not exaggerating. You, Rarity, are a breathtaking creature.”

Rarity’s cheeks reddened. And once again, I noticed that satisfied expression lingering on her face. It only lasted a few seconds, though, before she schooled it to a more neutral look. “It is quite a pleasure to have somepony who is most appreciative of beauty.”

“No, my lady. The pleasure is mine.”

Rarity covered her snout daintily with her hoof, giggling gently. “Do behave, Mister Wingman. There’s time for that later.”

“As you wish,” I replied, winking. “Though forgive me if I lapse once more. You are quite... irresistable.”

“And you are quite incorrigible,” Rarity declared, shaking her head. “Are you going to have a hard time keeping your hands off me, Wingman?”

“Maybe,” I said. “But for you, I’ll try my hardest to keep them to myself for the time being.” I winked. “Well, unless you say otherwise.”

Rarity shook her head once more, trying her hardest not to smile. She failed. “Miss Cheerilee was quite right about you, Wingman.”

“How is she?” I asked, curious.

“She is still quite the same, though she is starting to move with more purpose. It is quite enjoyable to watch a mare finally walk with more confidence.” Rarity looked at me. “And she has you to thank, I believe.”

I shook my head. “She could have found her confidence elsewhere.”

“I think not,” Rarity replied. “When a mare faces off against three other mares to defend you, it is pretty obvious.”

I blinked. “Defend me?”

Rarity nodded. “There was a reason why I set up our date here in Hollow Shades. I did not want you to face the brunt of anger that has been spreading around Ponyville. Sad to say, it would probably be better if you avoided the town for a while. Just some friendly advice.”

I looked at her for a moment, contemplating what she said. It took me a moment before I realized what had changed.

“Sea Swirl,” I said.

“Well, not only her,” Rarity huffed. “It started out innocent enough, I suppose. I had finally convinced Miss Cheerilee to talk about you when Applejack and Rainbow Dash, my other friend, joined in the conversation.”

“Wait a moment... Rainbow Dash? The Wonderbolt?” I asked.

“Yes,” Rarity nodded. “I believe she is quite famous among you humans. She was the first one to cross the portal, which scared Twilight senseless.”

Wait, what? “I’m sorry, Rarity... but this Twilight... is she Princess Sparkle? The Princess of Friendship?”

The unicorn nodded again. “Quite right. Twilight is another friend of ours. I wasn’t joking when I said Applejack and I share quite a familiar circle of friends.”

I blinked for a moment. Maybe it was my overactive imagination, but I felt a shiver run down my back. It seemed like every new discovery uncovered some more depressing consequences. It was fine when one Wonderbolt didn’t like me, but now that Wonderbolt had a friend who personally knew the leader of Equestria?

Great, Harry. What’s next, that all of them were the Elements of Harmony?

Rarity continued, unaware of my train of thought. “So, I was talking to Cheerilee, to get more information about you when your name was recognized by Rainbow Dash. She suddenly started talking about how she met you in Neighagra and how much she distrusts you. Then, Miss Sea Swirl appeared, asking if we were talking about a Harry Wingman.”

I winced. I tried to hide it well, but Rarity saw it. She gently patted my knee.

“I am guessing Harry is your name,” she said, softly.

“Yes. But Miss Rarity, I would prefer if—”

“If I refer to you as Wingman,” Rarity finished, nodding. “I understand.”

“Thank you,” I whispered. I sighed afterwards, rubbing my chin. “I am guessing the conversation turned... unpleasant.”

“Quite an understatement,” Rarity said harshly. “Miss Sea Swirl was saying... unfavorable things about you. Rainbow Dash and Applejack seemed quite convinced, the former talking about how she ‘should have known’. I guess it was too much for Miss Cheerilee. She shouted at the three, and Miss Sea Swirl shouted back. My friends and I tried to reason with the two, but the turnout was so bad that Mayor Mare had to intervene.”

I squirmed in my seat with every word. Oh, man. Did Rarity just tell me that my work name caused a small riot? I needed a drink.

“I’m sorry,” I said, shaking my head. “It seems I have a knack for causing you trouble.”

“Not your fault,” Rarity replied.

“I’m not too sure,” I said. “Honestly, I’m surprised you still want to have anything to do with me, really. Maybe it would be much better if you distanced yourself from me, make it easier on your friends.”

“Please, darling, I am a grown mare,” Rarity replied. “I know about Sea Swirl’s situation. And I know my friends well enough to know that they are only acting like this because one is playing matchmaker and the other... well, I should not say more. Plus, I like you. So, that is that.”

I looked at the unicorn for a moment, who stared at me firmly, daring me to counter her. Equestrian mares: they were something else. I conceded with a nod and said, “You are too kind, Rarity.”

“Yes, well I do have my moments,” she replied with a wink. “Though if you do not mind, let us move the conversation to something more positive. Like that delightful suit you are wearing.”

I chuckled. “Do you like it? It was made by quite a generous and special mare.”

Her eyes slyly narrowed as she placed her hoof on the side of her cheek. “Oh, really?”

“Not to mention, quite beautiful,” I added.

She giggled. “She must have been quite somepony.”

“One of these days, I shall endeavor to pay her back for such generosity,” I said, a bit of huskiness escaping my voice.

“Why, do tell.”

“Hmm, better yet, let me show you.”

The carriage began to slow as we arrived in front of the restaurant where I had placed my reservation. Helping Rarity down, I led her through the doors, making sure I held them for her. As we made our way to our table, I moved the seating-pad and waited for her to be seated, ensuring she was comfortable. All the while, my eyes never left her.

Not that it was hard, with both the way she dressed and the way she moved.

I kept my hands busy, lest they go somewhere untowards. I limited myself to her hooves and fetlocks, once touching her mane, tucking it behind her ear. I thought I was overdoing the hoof touching, and I made sure to ask if Rarity felt comfortable with it.

“Oh, quite,” she replied. “Your hands feel absolutely nice, warm and soft. I find it quite amazing how nimble they are.”

“Thank you,” I said, feeling through the hard parts to find it smooth and almost without any rough edges. “Let me pay the compliment back as well. I find your hooves quite immaculate.”

“Thank you, kind sir,” she replied, smiling. “I am a firm believer that a mare should always take pride in their appearance. Though I must confess, I was quite tempted to ask Twilight to cast that spell on me to give me those fabulous wings again.”

I blinked. “Huh. Is there such a spell?” I asked.

“Yes,” Rarity replied, smiling a bit wistfully. “Well, not pegasus wings. Which I guess makes the point moot.” She looked at my hands. “Though if I was a pegasus, I would be quite tempted to feel your hands on them. After all, with a name such as Wingman, it should feel quite divine.”

I chuckled, shaking my head. “You aren’t missing much, Rarity. My name isn’t actually an indication of my skills in handling wings.”

“Oh? Then how did you get your work name? Was it picked at random?”

“Not exactly,” I replied. “And you don’t want to hear it. It’s a story filled with much sighing and embarrassment.”

“Now you have me curious,” Rarity said, grabbing my hand with her free hoof. “Do tell, Wingman. How did you get your name?”

I looked around for a moment before nodding. I leaned forward, conspiratorially, and Rarity followed suit. “Well, it has to do with one of my teach—uh, with a pegasus mare. She wasn’t a particularly nice mare, constantly berating me on how poorly I... performed. Then one day, she offered to just lie still, daring me to make her, uh, scream.”

“Oh, this sounds like a naughty story.”

“Not quite,” I replied, smiling. “I was... well, I was a little frustrated, so I made her scream.”

“Oh-hoh!”

“By biting her wing.”

The unicorn’s eyes widened, her mouth slackened for just a second before she shook her head disbelievingly. She gently bopped my arm with her hoof. “Mister Wingman, I believe I said this to you once, but it is quite rude to tease a lady.”

“My apologies then,” I said, raising the said hoof to kiss it.

Yet another one who couldn’t believe how it had happened. I guess truth was stranger than fiction.

Dinner was wonderful. I talked a bit about myself, about my life back on Earth, while she told me how she began on her adventures as an Element. It was nothing grandiose, and honestly, it felt more like an exploration of the deepening of friendship between her and the other Elements. She refrained from saying names, of course, but I didn’t mind.

A few patrons seemed to recognize her, some pointing in our direction. However, I guess the respect they had towards Rarity was the reason why nopony gave us the stink-eye.

After dinner, we took another carriage ride, this time towards a flower shop, where I had reserved a small bouquet of undyed flowers. Presenting that to Rarity really seemed to please her, even moreso when I asked her if she’d give me the honor of allowing me to feed her.

“This night is quite wonderful,” Rarity whispered with her head in my lap as she stared up at the sky.

“I’m glad you’re enjoying it so far,” I replied, separating another stem and flower. I offered it to her, and she gently nibbled it, licking my palm in the process.

She chewed for a moment before swallowing. She licked my hand again. “I have never experienced being flower-fed. Not even like this. Quite frankly, I am surprised a human knew about it. The practice is quite... antiquated.” She looked at me. “Wingman, how did you know about it?”

“I got it from reading The Knight and Stallion,” I replied. “I found it weird, until Eve explained the finer details, of why it is considered romantic, to me. She was particularly thorough.”

Rarity looked at me. “Eve?”

“A friend,” I replied quickly. Maybe too quickly, as the unicorn pondered over that for a moment. After a moment, she just nodded.

“So she taught you a bit of Equestrian culture?”

“Yeah, quite a bit,” I said with a chuckle. “She taught me that a mare would give a flower to the stallion she was interested in. Apparently, it was a common practice done by earth ponies which was adopted by the unicorns and pegasi. Though I think giving vials of magic and primary feathers are trending again.

“Anyway, she told me that, symbolically, the sweetest thing a stallion could do was offer a flower back to her, which she would eat. He’d either use his hooves or his mouth to feed her.”

Rarity nodded. “That is quite correct. Though the mouth is a bit more... intimate because it can easily lead to kissing, which in turn can lead to something more.”

I nipped another flower out of its stem. “She mentioned that too.”

Rarity looked a bit unsure for the first time, her eyes turned away from me. I could see her cheeks slowly reddening.

“I don’t want to be presumptuous, Wingman, and Celestia knows the night has been wonderful so far, but I was wondering if—”

I silenced her by gently grabbing both her cheeks with my hands, slowly nudging her to look at me. Her expression was confused at first, her mouth opening to ask what I was doing, until she spotted the newly-nipped flower dangling from my lips.

“Oh...! Oh, my,” was all she said. As I lowered my head to meet her lips, her mouth opening daintily, just enough to devour the flower I offered, before sealing her lips with mine. We gave each other a simple kiss, just one, before she slowly moved away from my lap.

She settled on sitting opposite me, laying down on all fours. She stretched her neck, moved her shoulders slightly as she crossed her forelegs, back arching which made me, once more, aware of her tantalizing curves that were barely covered by her dress. She made me watch as she slowly chewed her prize with an easy and sensual smile. Holy crap did that put a fire in me. I could only stare at her whole being, maybe unconsciously licking my lips, waiting for her to swallow. And she took her time. She knew what she was doing to me, and she enjoyed every second of it.

When she did, I wasted no time. As much as space could afford me, I knelt beside her, grabbing her cheeks, feeling the finely brushed hair of her coat with my fingers. “Forgive me for being a bit forward,” I said, before attacking her mouth with mine.

Her lips parted easily, and our tongues met, slithering to meet each other. I felt one of her forelegs snake behind my head, keeping me in place as we shared a long fiery kiss that promised a lot of things. My hands roved over her neck, gently rubbing it in a circular manner. Her kiss suddenly felt hungrier, her lips and tongue now moving at a faster pace. I obliged, meeting her speed with mine until I felt wetness on my cheeks.

I stopped, reluctantly, and slowly moved away from Rarity, who was now sporting a few tears in her eyes. I gently wiped them away with my thumb.

“Did I hurt you?” I asked gently.

“No,” Rarity replied, shaking her head. “I... I guess I was just a little bit too happy. Oh, this will ruin my make-up. There goes my perfect image.”

I kissed her on the cheek. “Make-up doesn’t make the mare. Without it, you’re still perfect in my eyes.”

“Oh, you are the worst, Wingman,” Rarity declared, embracing my neck with her forelegs. “The worst to make such a mare so happy, even if it is for such a short time.”

“And you—” I pecked her right cheek “—are quite the seductress.”

“Oh, whatever do you mean?” she asked with mock innocence.

I replied by kissing her on the lips, “I mean—” again “—the dress—” and again “—and the teasing.” I separated myself from her. “You really didn’t think I wouldn’t figure it out? You did some research.”

A satisfied groan escaped her throat. “Oh no, darling, not research. That’s Twilight’s specialty. No, I acted on a few theories.”

“Hmm, educate me, Rarity,” I whispered in her ear. I felt her shiver.

“Oh, I like that,” she replied throatily. “We really should do this more later. Where was I?”

I nibbled her ear. “You were about to enlighten me.”

A giggle escaped her lips. “I know humans are predators, and I have met quite a few of our predatory neighbors. They always find the thrill of the hunt so exciting. I am also inclined to believe that none of your customers wear any clothes on your dates. And considering your culture of reverse gender roles and in regards to clothing, I wondered if by covering myself up and being a bit less... aggressive, you would be more... enticed than normal.” She smiled widely. “I think I was right. You could not keep your eyes off me.”

“Nor my hands,” I added.

“Nor your hands,” Rarity agreed. “You have been wanting to take me since you saw me in my room.”

“Yes I have,” I admitted. “Though Rarity, you didn’t need to go through all that to make yourself enticing. You are very easy on the eyes.”

“I believe you,” Rarity replied. “However, I am a bit of a stubborn mare. I wanted your complete attention. I wanted to be the only thing in your mind tonight. That is a bit of a dream for me, you see. To have somepony, someone, special. And only for me.”

“You have no need to worry then, Rarity. I am all yours tonight.”

She reluctantly let go of her embrace, slowly sitting on her haunches. I motioned to sit beside her, and she nodded, shivering a bit. “Oh my, is it me or is getting a bit chilly?”

“Hold on,” I said, automatically removing my jacket, wrapping it around her. She practically glowed as I tightened my embrace a bit, motioning her to come closer. I tried to keep balanced as much as I could, since she towered over me a bit in this position. In the end, she settled down on my lap once more as my hand gently caressed her neck.

A groan of pleasure escaped her lips. “Hmmm, I wish—oh, that was nice, would you—ah! Thank you.”

I continued to massage the spot, smiling at her. “You are very welcome.”

Rarity closed her eyes as she groaned once more. “Why can't they make stallions like you?”

“Because then I’d be out of a job,” I replied good-naturedly. “And you wouldn’t wish that against me, would you, Miss Rarity?” I gently licked her lips, which opened readily for me. My tongue met hers as we both explored each other just briefly before I separated from her. “Would you?”

Rarity giggled. “Of course not,” she replied, before letting out a sigh. “It’s just... there are days I would wish that stallions acted differently. More like you. Attentive.” She frowned. “Interested.”

I kissed her on the forehead, gently around the base of her horn. I felt her shiver from the contact, and when I came back up, saw the blush of her cheeks brightening. “It seems to be an ongoing theme here in Equestria. Miss Cheerilee, and now, you,” I said quietly. “You’d think that being an Element would at least ensure no shortage of interest. Surely you could capture the attention of many stallions.”

“Being an Element is actually part of the problem,” Rarity replied. “Though if I have to be honest, it is me. Or at least, my reputation.”

“What do you mean?”

Rarity looked at me for a moment, lips turned down in a frown. I immediately caressed her foreleg and shoulders reassuringly.

“You don’t need to answer that, Rarity,” I added.

“Maybe,” she said. “However, it is nice to have someone with a sympathetic ear. Would you mind terribly lending one to me?”

When I nodded, she smiled.

“I guess it starts with my family. Have you heard of the term Matched Pair?”

I nodded. “That’s when the family is basically just one mare, one stallion. A monogamous relationship. Very rare. And very polarizing. I think the most famous example is the one of Princess Cadance and Prince Shining Armor.”

“Correct,” Rarity replied. “There are more, less well-known, examples. Like Mr. and Mrs. Cake in Ponyville.” She paused. “And my parents.

“Growing up in a Matched Pair family was... difficult to say the least. Especially when you reach the age of social interaction. You are quite right saying the nature of Matched Pairs is quite polarizing. There is a bit of a romantic notion of one mare not sharing her stallion, where all his attention was on her. But there is also the reviled aspect of it, as a Matching Pair is not as practical or ‘harmonious’ as the traditional practice of herd bonding.

“I never really quite fit in. Unlike misborns, I was still considered raised ‘right’, but the fact that I only have two parents made me seem... less equipped than ponies raised in a herd. It came to the point that once I got my Cutie Mark, I changed my name and distanced myself from my family. I wanted, no, needed more friends, ponies that would not judge me because of my parents. So, I comported myself as a lady who would not be amiss in the Court of Canterlot. I even joined a herd for a while, convincing myself that I had finally come into my own.”

She sighed. “However, it did not work out. I guess familial bonds are stronger than we would like to think. As much as I wanted to fit in the herd, I felt at a loss when the stallion was not paying as much attention to me as I wanted. After some time, I realized that I wanted a stallion of my own, not shared with anypony else.”

“Like your parents,” I realized.

Rarity nodded. “Of course, I realized how impractical and selfish it was for me to think that. So, I settled on being a stallion’s First Mare, the one whom he shall pay attention to most. I took even more care with my appearance, used my hobbies of dressmaking, and my talent of finding gems to start a shop. I wanted to show that I was a mare who can provide, and who is proper and responsible.

“Things were looking up, especially when I became one of the Elements of Harmony. Even more so when I was invited to the Grand Galloping Gala a few months later. I was so excited, especially when I realized I could meet the stallion of my dreams!”

“And who is this stallion that captured your heart, Rarity?” I asked, smiling. For some reason, her face became harsh, transforming into something just short of a scowl.

“Prince Blueblood,” she replied.

I blinked. “Oh,” was all I could say. “I’ve, uh, heard a bit about his reputation.”

Rarity nodded. “Yes, well, he had a bit of a reputation back then as well, but I was naive. I felt that someone from Canterlot, someone with such a title, would be appreciative of the traditional aspects of... well, romance.”

“I am guessing he wasn’t,” I ventured.

Rarity huffed. “Not in the slightest. The whole night I spent with him was a complete and utter disaster of untold proportions!” She raised a foreleg to her forehead, near the horn. “The night ended with me calling him an uncharming royal pain.”

“Oh, I bet he loved that,” I said, chuckling. Rarity joined in as well.

“He was more bothered by the cake frosting I smeared on his coat,” she replied. “To be fair, Prince Blueblood and I met afterwards, and it was on better terms. He even invited me to the launching of his new airship, asking me to break the bottle. However, what happened at the Grand Galloping Gala gave me quite a fearsome reputation that hasn’t changed much since.”

“And what reputation is that?” I asked.

“A traditionalist mare, the one that stallions nowadays avoid like a disease.”

I made a show of looking at her from horn to tail. “I don’t quite see it, Rarity.”

“Except that you are not from here, Wingman,” Rarity countered. “I do not know if you could understand why I am quite an intimidating figure to stallions.” She smiled sadly. “And maybe that’s your advantage.

“You do not see me as a figure of power or translate my romanticism of tradition as me being an old-fashioned mare.” She looked away. “However, they do. To them, I am a horror of a mare who would only use them as a means to raise my station, for their comforts, and as a convenience.”

“That is quite presumptuous of them,” I replied. “Honestly, Rarity, they are doing both you and themselves a great disservice.”

Rarity relaxed, leaning even closer to me, closing her eyes. She had a satisfied smile on her face. “Oh, I am not quite sure. Lest we forget, I hired you as a convenience.”

“You hired me because you were in need of companionship,” I countered.

“And how does that discount the fact that I am using you to fulfill my own needs?”

“Everyone has needs,” I replied, softly kissing her mane, moving my hand lightly down her side. “And everyone has the right to be happy. Now, hush. I won’t stand for anyone talking badly about you. Not even yourself.”

Rarity let out a throaty growl of satisfaction. “I would have said that you were a perfect gentlecolt, Mister Wingman, if it was not for the fact that your hand is caressing my hip.”

I chuckled. “Ah, but I did apologize in advance.”

“Hrm-hmm. Yes, you did.”

My hand never left its place until we reached the hotel, and by that time, both of us were just barely controlling ourselves. Rarity was already patting my thighs, nuzzling my arm, tail swishing about. On my end, I was already tempted to take her right there in the carriage, especially when I smelled a strong musk that mingled with her scent—floral with a hint of rosemary.

I think the carriage-puller knew. He quickly had the ramp set up by the time we were in front of the hotel. I gave him a small extra bag of bits for his troubles. Rarity and I made our way towards the stairs, not quite running, yet not quite walking, until we reached her room.

It was quite modest, lit with multiple firefly lamps scattered around the room. It had quite a spacious bed, a few closets, a vanity mirror, and a balcony that had a clear view of the night's velvet sky, glowing moon hanging in the air. Any other details of the room were lost from the soft lighting. I wouldn't have noticed them anyway since my eyes rarely roamed away from Rarity’s magnificent form for less than a minute.

The unicorn strutted slowly towards the closet, her hips swaying hypnotically with every step. She looked back at me with sensual eyes as she motioned for me to approach with her hoof.

“Mister Wingman, would you mind assisting me in removing such constrictive clothing?” she asked.

“It would be my greatest pleasure,” I said rather huskily.

I let her magically guide my hands over on the right side of her barrel, where I found a small zipper. Zipping it open was also quite an interesting experience, like unwrapping a present. Her white coat, contrast with the red dress, seemed to glow in the semi-darkness, which only got me breathing harder.

I suddenly realized why Trixie loved undressing me.

As the zipper reached her hips, I noticed a black line going around her stomach. I realized what it was a moment later. I was kneeling down right behind her when I finally removed the dress, carefully making sure her tail wasn’t tangled, when I saw it.

Rarity was wearing panties, a light-blue pair with a dark slit in the middle. Again, it had quite a profound affect on me. The evidence of her arousal along with the very strong sense of musk overwhelmed me. I touched the moist fabric with my lips, enjoying her wetness, her taste. I felt her shudder at my kiss, letting me linger there until she moved away, shaking her head as I tried to stop her.

“Mister Wingman, behave,” she declared with a dangerous smile. “A lady has to ready herself.”

“You look quite ready, Miss Rarity,” I countered, breathing a little too much harder than normal.

“I shall be the judge of that,” she declared, moving towards the bed. “You may watch. Plus, I believe you are awfully well-dressed. Why don’t you slip into something more comfortable?”

I was already unbuttoning my shirt when she slid on top of the bed, magically removing her unmentionables. Her eyes were on me, smiling as I kept staring at her as I fumbled on my shirt. She slowly spread her hind legs, her marehood covered in shadows as she used her hooves to massage them.

Oh, wow.

She softly groaned as she touched herself. There was nothing vulgar with the way she spoke out, or the way she moved. It was a beautiful scene, like watching the sun rise of the very first time. Her eyes were half-closed, watching me as I finally unbuttoned my pants, cooing in a way that really drove me wild. Even with the limited light, I could see liquid glisten around her hooves as she moved a bit faster with her panting.

When I removed my boxers, I didn’t walk as much as sprinted towards the bed. Rarity’s smile widened as I looked at her completely, from her twitching forelegs, her wet hoof, her swollen teats, long neck, and to her beautiful cerulean eyes.

“Yes, darling?” she asked with a heated tone.

“I want you,” I said, almost growling out the words. Rarity’s hoof moved faster.

“Oh! Oh, yes!”

“I want to have you badly.”

A groan of pleasure escaped her lips, her eyes closed as she moved her hips along with her hoof.

“Let me have you, Rarity. Let me worship you.”

Her hoof lifted from her marehood, displaying itself for the first time in front of me. It was a beautiful sight, its pink lips swollen, as well as the clit sitting on top of it. It was spurting out clear liquid, quivering as it waited for its release.

I gave it to her.

All it took was one kiss—just one kiss to her swollen nub. Her hind legs immediately hugged my head, trying to pull me deeper inside her. My tongue moved, lapping her up as she exploded into an orgasm. Viscous fluid dribbled out in droves, leaving my senses with nothing but of her—her white coat, her warmth, her musky smell, her taste, and her muffled screams.

I didn’t know how long I stayed kissing her marehood, enjoying her shiver with each lick. Once she had settled down, she finally released the hold on my head, and I slowly climbed upwards, kissing her still-swollen teats, to her stomach, to her chest, and to her neck. I rubbed my swollen member at her lower lips as my eyes made contact with hers.

No other words were spoken. I kissed her deeply, enjoying the taste of her mouth as I slowly entered her, my aching member becoming more agitated by her moist, moving walls. I thrusted slowly, trying my best to ignore the loud part of me screaming to take her fast and hard. I made sure I kept my eyes on hers, my lips, if not kissing, telling her how much I wanted her. How much I needed her.

Rarity’s only response was moans, which was beginning to get louder with every second. Her walls enclosed around me, almost twisting in ways that had me swimming in pleasure. In the end, my louder voice won out as I began to build speed. The pressure inside me mounted up to something almost unbearable, until I screamed out as the threshold burst.

I tirely collapsed into Rarity’s ready embrace, her hind legs trapping me inside her. She licked my shoulders, which only added to the sensation as I shuddered with every burst; my vision turned completely white; my nose smelled rosemary; I could barely hear my groans, muffled by her chest.

I finally extracted myself from her lips, but not from her embrace. I didn’t mind. I enjoyed every bit of her warmth and floral-honey scent as I slowly recovered. I extracted myself from her embrace, watching her green eyes sparkle with joy as my hand slowly combed through her pink mane.

“Harry, that was wonderful,” Eve said.

I looked at her blankly. Why was—?

“Harry, what’s wrong?” she asked.

I breathed a little harder, staring at her hard. I licked my lips, feeling for her hips. They were warm. They were real. I shook my head. “Nothing. Nothing’s wrong.”

I kissed her hard. Eve. Mine. A felt her tense a little, but slowly melted as I moved my hands around her body, my fingers feeling through her well brushed coat. I wanted to kiss her everywhere, lick every inch of her. My loins stirred, but I held off, wanting this to last.

Slowly and steadily, my fingers touched her swollen pink lips, feeling for her walls. She moaned, licking my arm as I brought her over the edge again. I watched shudder with every stroke until she bit her foreleg to muffle her scream. She wet my hand, moistened my fingers.

Eve. Mine.

I wrapped my arms around her, enjoying her warmth as I waited for her shaking to subside. I whispered sweet nothings to her ears, praising her beauty, describing aptly how soft was her coat, how immaculate was her hooves, and how irresistible she smelled. Then, we made love. We started with pony missionary, moving slow and deliberate. We grunted as we slowly shifted positions, having her lie sideways as I kissed her hind legs, before we faced each other once more.

Eve closed her eyes, her groans getting louder as I went faster. Oh God, we were so close. I could feel it. The air smelled of perfume and musk and sweat. There was no one in the world but us. I grabbed ahold of her pink mane as we rocked against each other faster and faster. She opened her eyes, green orbs looking at me with longing as her smile lit up my world.

“Faster, Harry. Please, go faster.”

I went faster. I couldn’t stop staring at her beautiful features, watch them twist in pleasure and ecstasy. Time seemed to slow down, which only increased my need for release as Eve whimpered in pleasure.

“Harry! Oh Harry!” she began.

I didn’t trust myself to speak. I only leaned forward, and she followed suit, her sparkling green eyes hinting playfulness as we kissed.

Eve. Mine.

We climaxed together.

I collapsed beside the unicorn, panting, spent. I could barely do anything except kiss her shoulders. Judging by the way she could barely move, she hadn’t the energy to do anything as well. I closed my eyes, enjoying the scent of rosemary.

“Oh, Wingman, that was wonderful,” Rarity whispered.

I opened my eyes. Eve was gone, and I was in bed with Rarity. I shuddered for a moment before hugging my client, the one I was supposed to spend the night with.

Holy shit. What the hell was wrong with me?

“Anything for you, Rarity,” I whispered back, snuggling a little closer to her.

I couldn’t sleep. I just stayed awake, enjoying the warmth of Rarity’s body as she slowly drifted to sleep, her snores coming out in gentle whispers. After an hour of hearing the rather comforting rhythm of her breathing, I slowly extracted myself from her, and went towards the balcony.

The night air hit me like ice as I made my way to the railing. I stared at the starry velvet sky, watching a quarter moon hang in the air. There was no one in the cobblestone streets below. No pony saw me in my all naked glory, except for the crickets that whistled softly and the fireflies that glowed around the area like specks of ember.

I closed my eyes and saw Eve, face in ecstasy. I shivered.

“You must be cold.”

I immediately turned around, hand clutching my chest as I watched a shadowed figure approach. The first thing that came to light, when the figure stepped out the balcony, was a white horn, followed by purple mane.

“Oh, my apologies, Wingman,” Rarity said. “I did not mean to frighten you.”

“And I didn’t mean to wake you, Rarity,” I replied with a soft smile.

“You have done no such thing, darling. I felt a bit thirsty, and when I saw you here, it piqued my interest. Quite underdressed, are you not?”

I looked down at myself. I forced a smile. “Maybe a bit.”

Rarity looked at me for a moment, then asked, “Wingman... is there something bothering you?”

I hesitated for a moment before shaking my head.

“Liar,” Rarity said, giggling.

“Oh, Miss Rarity, you wound me,” I replied, mock clutching my chest as if I’ve been pierced by an arrow. “What have I done to raise doubts?”

“Well, you called me Eve.”

W-what?

“Twice if I recall,” Rarity continued. “I think it was when you were rubbing my coat, whispering how soft it felt.”

“Oh. Oh God,” I muttered, covering my face with my hand. “Miss Rarity. I’m... I... oh God. I’m sorry. I’m so sorry.”

I felt a soft warm hoof touch my leg. I lowered my hands just enough to see the unicorn smile warmly at me. She motioned towards the balcony door.

“Come, Wingman,” Rarity said softly. “The night air is far too chilly for me.”

Hmph, I wasn’t the only liar in this room. However, I didn’t say anything and went inside, with Rarity following suit. She trotted, overtaking me, jumping over the bed. She sat on her haunches, relaxing a moment, then tapped her hoof on the bed, inviting me to sit with her.

I hesitated for a second before climbing up.

“So... your friend, Eve?” Rarity asked.

I sighed. “Miss Rarity, look, I want to apologize for that. Her name came out by accident. I’m—” I stopped, a groan escaping my lips. “It's...”

“Personal?” she ventured.

“Unprofessional,” I finished. I gritted my teeth, unwilling to look at her. “This was supposed to be a night for you. No one else’s. Not mine. Not...”

There was a moment of silence before I felt something warm touch my shoulder.

“Harry, what is bothering you?”

I looked up, expecting Eve to replace Rarity once more, but no. It was still the Element of Generosity, looking at me worriedly. I sighed. If she was calling me by name, I must look like a trainwreck.

“I can’t burden you with this, Miss Rarity.”

“After the good you have done for me tonight and, from what I have heard, what you have done for Miss Cheerilee, I disagree,” she replied, her tone turning a bit hard. “In good conscience, I cannot just turn deaf ear to someone like you.”

I said nothing.

Rarity slowly nodded, not asking anymore. Instead, she cupped my cheeks with her hooves, and kissed me in the forehead gently, before shrouding me with her embrace.

I began to talk. Slowly. Surely. I didn’t know what exactly went through my head, but I explained about Eve, my handler, about my friendship with her, and her admission during that drunken night. As I went on, Rarity slowly pulled me down towards the bed, nodding and not saying anything. By the time I finished my tale, I was returning her embrace.

“And she hasn’t said anything?” Rarity asked.

I shook my head. “Nothing, whatsoever.”

“Do you have any idea why?”

“I may have a few theories,” I replied. “Eve’s a paramount professional. She doesn’t follow the rule of ‘inspecting’ her Gentlemen and maintains professional interaction during work duty.”

“You think she doesn’t want the trouble of maintaining a professional relationship with you?” Rarity asked.

“Maybe,” I reasoned, “but our relationship is already less formal at most times. I think it’s something else.”

Rarity just nodded, and rubbed my shoulder reassuringly.

I continued, “That night, it was between friends. Nothing related to work, just us. And she only admitted it to me when she was inebriated and thought I had been asleep.” I sighed. “I think why she won’t say anymore is because she feels like me: that it would jeopardize our friendship.”

Rarity blinked. “Why would you say that?”

“Because I’ve seen friends who, after taking the step, were irreconcilable afterwards when it didn’t work out.”

“Has it happened to you?” she asked.

“I—well, no,” I admitted. “But... I know, first-hand, how to lose a friend. I will never forget that feeling when I lost her.”

“Her?”

I nodded, sighing. Cathy. Abandoned her when she needed me the most, all because all I had in my brain at that time was boobs. Shaking my head, I said, “Doesn’t matter. What matters is if the subject was broached, and she says yes... what happens when we don’t work out? Will it turn out like the friends I’ve seen, who won’t even talk to each other anymore?”

“Yet you are still willing to try,” Rarity said. Then she giggled. “Otherwise, you wouldn’t have been whispering her name instead of mine.”

“Sorry about that,” I muttered, shifting uncomfortably, which only got Rarity to hug me a little harder.

“Like I already said, it is quite alright,” she replied firmly. She giggled again. “Besides, the story is worth listening to! Love blooming from friendship! Two sides, one who has been harbouring such feelings, and one just discovering them!” She shivered. “Romance! Trials! Tribulations! Oh, darling, this is divine!”

I smiled. I couldn’t help it. “Well, I am glad my suffering entertains you, Miss Rarity.”

“Oh, hush. So, what do you plan to do?”

I shrugged. “I don’t know. I’m not sure if she wants to even broach the subject itself as well. I think we’re both happy with what we have, you know.”

“Yet, clearly she wants more. And judging by earlier, you as well,” Rarity countered. “As a somewhat hopeless romantic, my advice is talk to her about it. It doesn’t have to necessarily end with the question of whether you remain as friends or become more, but at least be clear on where both of you stand.”

I looked at her unsurely.

“I really think it will be much better than what is happening now,” Rarity continued. “And someone told me earlier that everyone has the right to be happy. I think that someone has to practise what he preaches.” She winked at me. “Don’t you think so?”

It took me a moment before I pulled Rarity to me. She let out a cute ‘Ooh’ before she surrendered to me. I kissed her neck gently. “You are one generous mare, Miss Rarity,” I said. “These presumptuous stallions? They don’t know what they are missing.”

“Maybe, but you do, don’t you, Mister Wingman?” Rarity’s eyes roamed downwards. “Or else, I wouldn’t be feeling that. You are quite insatiable.”

“It is because I have a beautiful mare in my arms,” I replied. “And she is a generous, fashionable, kind, and very lovely.” I stared into her cerulean eyes. “Her name... is Rarity.”

I slowly pinned her in the bed, watching her glow with delight as I said her name, again.

I never misspoke it afterwards.

I woke up, feeling chilly air enter through the balcony door that had been left open last night, yet comforted by the warmth of the unicorn mare beside me, mumbling in her sleep. I spotted sunlight coming through the windows. Apparently, even with Hollow Shade’s reputation to block or absorb sunlight, it couldn’t completely stop it when the sun was raised for the new day.

With some regret, I extracted myself from the bed and made my way towards the vanity mirror, where my clothes still lay scattered. I dressed up slowly, watching Rarity continue to sleep. I wrote my call name in my card, and added ‘Thank You’ to it as well, leaving it on the bedside table. I gently kissed her cheek before exiting the room, closing the door softly behind me.

I made my way out of the Inn, noticing that the morning wasn’t as active as the night. I saw some sleepy looking carriage-pullers, taking a moment to pause to cover their yawns. The only active ponies around were fillies and colts, running around the area, shouting in glee. Some even pointed towards me as I passed, and I gave them a small smile in return.

Eve was outside the enclosed chariot, looking as professional as ever: brushed coat, combed pink mane, complete with red cat-eye rimmed spectacles perched on her snout. I took a deep breath, remembering the image of her in ecstasy, and my heart skipped a little beat. I immediately squashed the feeling down, though, and made my way to her.

“How was the date?” she asked, smiling.

“Hit a little snag at the end, but it worked out fine,” I replied.

“And Miss Rarity?”

“A wonderful companion,” was my immediate response.

“So, I’m guessing she liked you,” Eve said.

“Safe to say.” I looked at Eve for the moment, just admiring her features. She gave me a confused smile, then looked at her forelegs.

“What? Do I have something in my face?”

I shook my head. “Nothing. It’s just... you look good today, Eve.”

“Hah. Well, that’s new. But thanks, Harry.” She looked at me, head to toe. “You look like you could use a brush.”

“Hmm-hmm,” was all I said, my eyes not moving from place. After a moment, I looked away, sighing a bit.

“Harry,” Eve called, frowning, “is there something you want to talk about?”

I looked back at her, at her worried green eyes. I thought back on my conversation with Rarity. I took a deep breath, opened my mouth. I formulated on what to say. There were so many things to talk about...

Eve, I was awake that night.

Eve, I think you’re pretty.

Eve, we’ve been friends so long, and I may feel that I want more.

Eve, there was nopony else I could think of to be a better special somepony for me.

… and many more.

There were some I felt would work. Others felt too long. Even some that felt like something that only a television drama or a fictional character would say. And all I had was her in front of me. Eve. My friend. Eve, who may be someone more.

Everyone deserves to be happy.

But... wasn’t I happy with what we had now? Was I willing to risk that?

“Nothing,” I said, smiling at her. Shaking my head, I walked towards the chariot, hand going towards the door knob.

When the time was right, I decided. I looked at Eve, smiling. Maybe next time, when we’re both ready. When we’re both on the same page. And if that never comes... at least, I would still have her as a friend.

I sighed. Out loud, I just said, “Nothing at all.”

“Wingman!”

I blinked. I turned and spotted Rarity coming at me, unclothed. She had a playful smile on her face as she began to cross the cobblestone road. I looked at Eve, confused, who looked back at me with probably an equal expression.

She walked forward, professional smile on her face as she extended a hoof. “Miss Rarity? Hello, my name is Ever Ring, and I’m his hand—”

Rarity just brushed past her, eyes only on me. Eve’s eyes narrowed with annoyance, which widened a bit with surprise as Rarity stood on her hind legs, pinning my shoulders to the chariot and gave me a very deep kiss. I didn’t kiss back, but I still felt her tongue snake through my lips, unopposed.

When her tail rubbed up my leg, Eve’s eyes widened even more, if that was possible, threatening to pop from her sockets. Her jaw opened in disbelief, which remained open even when Rarity had finally separated from me a few seconds afterwards.

“Darling, last night was utterly amazing,” Rarity declared, in a bit too loud voice that felt... well, I couldn't quite place it. “You are everything I’ve been missing my whole life! Oh, I cannot wait until we can meet again!”

Rarity pushed herself away from me and trotted towards the still-shocked Eve, looking at her from head to toe.

“Dear, your mouth is open,” Rarity declared. Eve immediately closed her mouth. “Are you his handler?”

“Uh, yes, my name is Ever Ring.”

Rarity made a ‘hmm’ sound before saying, “Well, Ever Ring, you have quite a perfect Gentleman here. Worth keeping, I say. Does Gentleman for Mares operate like the other companies? Could I buy him off from you?”

“I, uh, that is—”

“Oh look at the time,” Rarity declared in an even louder voice. “I’m sorry, but I’m quite needed elsewhere. I shall call Gentleman for Mares, and see if we can work something out.”

She turned her around, and Eve’s eyes hardened as she stared at Rarity, who once more stood on her hind legs, forelegs on my shoulders, and gave me one simple peck on the cheeks before she winked.

“Good luck,” Rarity whispered. Then, she said, loudly once more, “Ta-ta, darling! I hope to see you soon!”

I could only stare as the purple-maned unicorn took her leave, gracefully crossing the cobblestone roads and back towards the hotel. I must have stood there for a few minutes, and I’d probably have stayed like that if it wasn’t for Eve, who roughly nudged my leg.

Coming back to my senses, I looked at my friend. Her eyes sparked with anger, but her expression remained neutral. She gave me a look, and motioned towards the chariot, raising an eyebrow. I immediately opened the chariot door, and we both climbed in.

The rest of the trip was spent in uncomfortable silence, with Eve staring outside the window, looking stiff and deep in thought.

Author's Notes:

The second to last chapter. Next, the end of Gentleman for Mares.

Thank you, shira, coandco, Permanent Temporary, Ponyboy245, grey_conscience for editing, pre-reading, and as general idea bouncer and general characterisation. I could not have done this without you guys.

EDIT: Thanks to AnonPonyDASHIE and TownCrier for the additional help.

Epilogue is coming. For the meantime, though, enjoy this chapter.