Holy shit… it’s morning. I actually passed out while writing.

How far did I get? I need to check.

Oh… so, yeah… that…

It would appear that I have… well… developed feelings for Derpy. Real feelings. Love feelings.

Once I realized what I had said, once my brain caught up with my mouth, I was… understandably distressed.

‘Wait… wait wait wait wait wait wait… what? What?! WHAT?!’

Suddenly that still night didn’t seem so still, and that frozen moment seemed like it was moving at the speed of sound, and I noticed that I was actually sweating out in the snow, and that for the past minute I’d just been staring at a dark house, out in the wind and cold.

And then… I freaked the fuck out.

“Oh no… Oh nonononononononono,” I chanted to myself. ‘This is not happening. This is not happening again. Time to leave Guilty! Time to get out of here! You’re just staring at her house. Time to go, Guilty! Walk, damn you, walk!’

I forced myself out of my trance. I hadn’t noticed that the wind had started to pick up. I needed to get home, fast, or else I’d be caught out in another blizzard. I walked. I walked and walked and walked, chattering to myself all the way, and before I’d even thought I was out of the town proper, I was opening my front door.

I fumbled with my lock; my hooves were shivering, or maybe they were just shaking. I was planning on running upstairs and writing. I wanted to get feelings on paper right then and there. I was so far into my own head right then. I needed to write all the feelings down; I needed to take them out of my head and look at them all. I needed to assess things, badly.

However, something pulled me, rather violently, out of my head. As I rather hurriedly threw open my front door, I was greeted by the fire-lit scene of a certain pink mare’s jiggling backside being impaled by a certain white stallion’s gargantuan rod.

“SOOO BIIIIIIIIIIG!” Pinkie cried as Crook continued to ram himself into her. His chest writhed against her back as each vigorous thrust slapped flesh against flesh in a din of cacophonous sex. Whatever turbulence and confusion had been brewing inside me had been blown the fuck out of my skull by this enthusiastic display of raucous fucking. I was now far too distracted to be having a melt-down.

“Hey, Guilty,” Crook panted without missing a beat. “Is that cheese?”

‘What the fuck is he— oh yeah… the cheese… I forgot all about that.’ “Um… yeah… crackers too. Just gonna… put it in the fridge.” ‘Geez, it fucking reeks in here.’

Pinkie turned her tired face over to see me. Her mane was a frazzled mess, and she was struggling to support the weight of Crook’s massive frame. “*huff*…*gasp*… Hey there… *pant*… Guilty…*huff*… what’s… *gasp*…. shakin’?”

“Uh…” ‘Well this is awkward.’ “...not much. Just… coming back from a poker game. Hehe.” I was face to face with a mare being plowed by my best friend. I’d been in this situation before, but never had a mare tried to exchange mid-coital pleasantries. Crook hadn’t even slowed down, he was still fucking her stupid. She was even drooling a little. The whole fucking thing was impossibly surreal.

“Oh, f-fun…*pant*… I b-b-bet you’re suuuuper DUUUUUUUUUPERRRRRAAAAAAAHH!” Pinkie’s sentence got away from her as she climaxed rather suddenly. Crook neither stopped nor slowed as Pinkie came, he just kept on keeping on. Seeing as Pinkie looked like she’d forgotten what precisely she was talking about, and even that I had been talking to her at all, I opted to quickly slip away and deposit my cheese in my fridge. The kitchen, I noticed, had about a dozen empty beer bottles littered across the counters. No big deal. I’d worry about it in the morning.

“So Guilty!” Crook called from the living room. “You want in?”

“Wooo yeah!” Pinkie cried in agreement. “Let’s make a… *huff*… Pinkie Sandwich!”

I stared at them from over the little bar that separates my kitchen from my living room. I could see Crook’s massive member penetrating her blushing genitals over and over and over.

For whatever reason, something about it just seemed so… clinical.

My penis certainly seemed game, but my heart wasn’t really in it.

“I’ll… pass.”

“S’cool,” responded Crook, still fucking away. “Goin’ to bed?”

“Yeah. Pinkie staying over?”

“S-sure! Sleepover…*huff*… wooooo!” she yelled happily.

“Okay.” I yawned. I hadn’t realized how beat I was. “You guys can take the cloud. I’ll be upstairs.” I started towards my bedroom.

“A’right,” said Crook.

“Good night…*huff*… Guilty!” Pinkie called after me. The sounds of their fucking followed me all the way upstairs. Even in my room, I could hear them faintly. I briefly tried to write but… I was just too distracted. Even thinking about anything was difficult. My mind was just filled with sex. I couldn’t focus properly on the task at hoof.

After several attempts to write a paragraph or two, I gave up. The noise from downstairs was preventing me from processing anything meaningful. So, I took a swig of the whiskey Crook had left in my room, pleasured myself quickly, and went to sleep. It wasn’t even a good bate, I just needed my erection to go away.

Once I knocked out I had no dreams. I simply laid down, sat up, and found it to be morning. That was the first time that happened to me, it was pretty neat. I had the faintest trace of a hangover from the wine and whiskey, but not enough of one to bother me. I picked myself and stretched, taking a nice deep breath and discovering that the air smelled like… syrup?

I pulled myself out of bed and forced my hooves to carry me downstairs. I didn’t feel particularly rested, what with my sleep not feeling like sleep. I found Pinkie working away in the kitchen. By the looks of thing she’d made breakfast for the three of us. There were three little plates of waffles, complete with butter and maple syrup sitting on my table.

“Hey… Pinkie.” I shook my head to try and knock the weariness from it.

“Rise and shine, Guilty! Have some breakfast! I made chocolate chip waffles!” she proclaimed.

I cringed at her outburst. There was the hangover. “Thanks… *ahem*… Pinkie. I take it your date went well.”

“Yes indeedy! Oh my gosh! Crook is so big! I was a cream-filled Pinkie last night, that’s for sure!”

‘Fuck me… her voice is so loud… and high… and it’s soooo early’ “Well that’s…” I suppressed a groan. “... swell, Pinkie.”

“Yepperuni!” she responded far too cheerily. I decided to take a seat and get a good look at the breakfast in front of me. ‘Yes, those are in fact waffles. Hey look, that’s a shot glass filled with syrup, how cute. Oooh, the butter’s even been whipped. Pinkie sure went all out with this—’

My eyes shot open as something very troubling occurred to me.

‘I do not own a waffle iron.’

“Hey uh… Pinkie?”

“What’s up, Guilty? Is the waffle too hot? Is the syrup too cold? Oh, I know! I forgot the orange juice! Wait right there!” She was so full of energy. It was kind of painful.

“No Pinkie, I… well actually some orange juice would be great, but… how did you make these?” I asked.

“Well… first you take some flour, and some salt, and baking powder, and—”

“No… not that… I mean…”

“Oh, you mean the waffle iron.” She reached back into the kitchen and produced the appliance in question. “I never leave home without it.”

I blinked. “You never leave home without a waffle iron?”

She shrugged. “Well, not always never. Just sometimes never.”

I nodded so as to feign understanding. The puzzle of what she had just said was a little too complex for my tired state. Regardless, the waffles were pretty good. I’m not much of a chocolate-chip-guy, to be honest, but they were certainly palatable.

“Do you want whipped cream or jelly beans on yours?” she asked, producing both a bag of jelly beans and a can of whipped cream. I waved a hoof dismissively, trying not to gag at the thought such a flavor combination. Pinkie quickly joined me at the table. The moment she tried to sit down, however, she bolted back upright with a gasp.

“You okay?” I asked through a mouthful of waffle.

“Owie wowie. I don’t think I’m gonna be able to sit down today. Owie-ow-ow.” I noticed she was standing a little bowlegged. ‘Ah… sore pussy.’ “I’m super ouchie down there. Crook is really rough.”

“Did I hear my name?” asked Crook as he emerged from the bedroom.

“Yes, we were just calling you a sexual dynamo of unsurpassed stamina and power,” I snarked.

“Sounds about right,” he said as he made his way over to Pinkie. “Hey, you,” he crooned in a sultry voice. ‘Are they going to start kissi— yes, yes they are.’ Without a second’s hesitation, the two of them began noisily sucking on each other’s faces. They were pretty fucking obnoxious about it, too; they were almost making it hard to eat.

Crook doesn’t have the same hang-ups about kissing that I do. He’s happy to tongue wrestle mares whenever. To be honest quite a few whores don’t mind it at all, but I digress.

“So, Crook, you ready for that manecut?” I asked. Anything to get them to fucking stop.

Thankfully Crook did pry himself off of the party pony. “What?” he asked, clearly confused.

“Remember? Yesterday? Close Shave?”

He just stared blankly at me.

“The old guy?”

“Oh, him,” he said, finally taking a seat. “That guy was serious?” He stared gleefully at the breakfast in front of him.

“Yes… he was… we should go. I don’t want to deal with his shit later.”

“Oh, I love Close Shave!” interjected Pinkie. “He’s super duper nice. Whenever he cuts my mane, he gives me a lollipop!” She made a single effort to bounce on her hooves but immediately regretted it. She winced in pain again and took a bow-legged stance again. “Ow,” she stated simply.

“Nice? That guy?” Crook scoffed. I’ll admit, I was a tad doubtful as well.

Pinkie nodded. “Yes indeedy! Okay, well, he kind of acts like a meanie-pants but he’s really really really nice once you get to know him.”

“I’ll believe it when I see it,” said Crook as he brought the shot glass in front of him to his lips.

I reacted too slowly. “Crook that’s not—!” Crook began coughing as the sweet sticky liquid filled his mouth.

“Oooh! You like to drink syrup too!? I like to put on my cereal.” I just stared at her for a second.

Eventually Crook broke the silence. “Guilty, *cough* is that whiskey still upstairs?”

“As far as I know.”

Wordlessly, Crook stood up and walked toward the stairs. Pinkie and I watched him go.

“Crook drinks a lot, huh?” asked Pinkie, voice showing a hint of concern.

“Yeah, he does,” I said.

I didn’t really have anything else to add.

After that, breakfast proceeded normally. We all ate. Pinkie said goodbye. Crook and she kissed for several minutes before she actually left. I washed dishes. I cleaned up all the beer bottles from the night before. I changed the sheets on the bed. Crook decided to have a beer. I mopped the floor in front of the fireplace… thoroughly. I gave my bathroom a quick scrub. Crook started whining that he had his date with Applejack soon, which I had honestly forgotten about. I told him we still needed to go to Close’s. We decided we’d visit him later in the day. And Crook made his way off to...

Oh, wow, it just occurred to me that he was meeting Applejack at Pinkie’s bakery. That must’ve been awkward.

Wait… not Pinkie’s… she just works there.

Anyways, Crook left for his date. He promised he wouldn’t be long so I decided I’d just wait for him.

And then I was alone again.

And it came flooding back.

There was nopony to put on a face for, nopony to hide my unpleasant emotions from, no audience for my act, and that brought everything bubbling to the surface. It was as though my train of thought from the night before had been frozen in time, and Crook leaving had thawed it.

Now, to clarify, this wasn’t one of my breakdowns. I wasn’t freaking out. Okay, well, yes I was, but it was different. I wasn’t having a physical panic attack, though, I was just worrying like there was no tomorrow.

‘Am I… am I really falling for Derpy? Oh Celestia, this is Sunny all over again. I’m going to want more than her, and it’s going to drive her away.’

‘But what if she feels the same way? Maybe we could actually be together.’

‘And what if it makes her hate me? What if she starts sympathizing with Applejack.’

‘She stood up for me, she at least likes me as a friend.’

‘Or maybe she’s like Pinkie Pie. Maybe she’s just that nice to everypony.’

‘But maybe I’m special. Maybe she actually does have feelings for me.’

“And maybe I’m going to make a fool of myself, and everypony in town will hate me, and I’ll feel uncomfortable just walking the streets of Ponyville, and maybe I’ll have to MOVE ALL OVER AGAIN!” My voice rang through the halls of my empty home, reverberating a shrill echo of my impotent rage. At some point my internal struggle had found voice; apparently I’d been talking aloud to myself for at least a minute or two. My throat was raw from shouting.

“I need… *huff*… cereal,” I said to no one at all. That was just what I needed: something sweet and delicious and totally lacking in nutritional value. I poured myself a bowl of Waffle-Bitz (with a “z”).

It’s basically just little maple-flavored waffle-shaped sugar cakes and it’s amazing.

A bowl, a spoon, some ice-cold milk, and I was ready to chow down. I took a bite. It was nirvana, pure sucrose-laden bliss. “Oh, my Celestia, this is just what I needed.” Apparently talking to myself was a new hobby I had taken up.

So, I munched and crunched and chomped and chewed all the delicious tiny waffles. I daresay they were better than the actual waffles I’d just eaten. Not to discredit Pinkie, it’s just that… well… tiny crunchy waffles are amazing. Actually, in their own way, they’re kind of soul-nourishing. I felt much better after that.

As I washed the bowl from my second breakfast, I heard a knock at the door.

‘Oh, hell, Crook’s back. I really hope he didn’t do something stupid… or evil… or both.’

I answered the door, expecting to find my jackass friend with a big shit-eating grin plastered on his face. “Please tell me you didn’t do something that I’m going to regr— oh…” I found myself blindsided by the arrival of a former client. “Twilight,” I said rather dumbly. I wasn’t expecting her at all. The little lavender mare was standing nervously at my door, blushing all the way up to her ears, as per usual.

“Oh, is… is this a bad time?” she almost whispered. She looked almost ashamed to be here.

And just like that, I was completely in the act. Big friendly smile. Comforting tone. “Unfortunately, Twilight, I’m expecting somepony shortly. I don’t really have time for a session.” Sexy chuckle. “I’m free this afternoon, though. Would you like to make an appointment?”

“Oh I’m… I wasn’t really… I don’t want a… I’m just… Would it be okay if...can just come in for a minute?” she asked, finally.

An escort always has to be careful with this sort of thing. A client asking if they can “just come in” might end up trying to squeeze a session out of you. If that happens it’s best to just firmly ask the client to leave, and to come back another time.

That said, I didn’t think that’s really what Twilight was after. So, with only a tiny bit of caution, I let Twilight into my home. Luckily, thanks to my obsessive desire to clean all messes immediately, any of the mess from Crook and Pinkie’s night was already gone, and my home was perfectly presentable. Now, to be fair, Twilight wasn’t truly a client right then, but she was still a guest, and as such, deserved the same treatment. “Would you like some tea?”

She shook her head. “No, thank you. I’m fine.” She cleared her throat. “Can we… talk?” she asked cautiously.

“Of course. Here, sit.” I motioned for her to join me at my table. She took a seat, and so did I. It felt just like a session, to be honest. “So, what’s up, Twilight?”

There was that blush again. “I just… I wanted to…” She took a deep breath. “… I’m sorry.”

‘Interesting.’ I put on a confused smile. “For what?”

“For… running out on you yesterday. It was… really very rude of me, I was just…” she trailed off.

“Out of it?” I offered.

She chuckled nervously. “Kind of.” She proceeded to stare at my table with a rather dour look on her face.

I felt I had to speak up. “Something’s troubling you.” It wasn’t a question.

“… Is it that obvious?” she asked almost pathetically.

“A little bit,” I admitted.

She just sighed in response.

“If I may venture a guess… I take it this has something to do with that stallion you were talking about last time?”

She nodded sullenly.

“Would you like to talk about it?” I’m not sure why I asked that. Normally something like this would fall under the territory of an actual session but… well… I’m gonna blame it on Crook. I’m sure it was somehow his fault I was drawing the line a bit too far back. Things are usually his fault. That was it.

She sighed again. “I kind of… broke his nose.”

‘Oh shit, that wasn’t just a rumor?’ My eyes must’ve widened, since Twilight was instantly trying to play it down.

“It was a complete accident! I swear!” That wasn’t exactly reassuring, to be honest. If she can break somepony’s nose accidentally, I’d hate to see what she could do if she was trying to hurt somepony. "We were fighting and… and… and one thing led to another… we started tug-of-warring over this… stupid flower pot and then I let go of it and…”

“And he pulled it right into his face?”

“…yeah…”

I laughed slightly, which served to calm her down. Making light of a client’s worries is Escort 101. “And so… you’re in a fight right now?”

“I guess…” She cradled her head in her hooves. “I don’t know. He said he never wanted to see me again, but… he’s said that before.” And there was the sobbing again. “He just… *sniff*… he makes me so upset sometimes.” Okay, this was really something I should’ve been charging for. Stupid Crook. How dare he somehow make me not realize this fact at the time? “I don’t… *sniff*… I don’t know what to do. Part of me… *sniff*… part of me wants to break up with him.” The tears in her eyes were kind of heartbreaking.

“But, part of you wants to hold on to what you have.” She nodded. It was the age old problem: Do I stay or do I go? I’ve have helped literally dozens of mares with this conundrum before. I’ve helped mares realize that they really love their partner despite their flaws. I’ve helped mares realize that they were in a toxic relationships and given them the courage they need to walk out the door. I’ve aided more mares than I care to remember with this exact life-changing dilemma.

And then came the question that always comes.

“What…*sniff*… what do you think I should do?” she asked, eyes filled with desperation.

‘Do I go with a pep-talk approach? She might appreciate that. Do I tell her she has to figure it out for herself? She seems smart, she might just need a bit of confidence. Maybe I could just go the old listen to your heart route. It works more than it should.’ For a few moments I debated which of my many techniques I should use.

Ultimately, however, I just… couldn’t think of anything that seemed worthwhile. I racked my brain trying to come up with the best solution I could for Twilight. For whatever reason (Derpy), I just.. didn’t feel qualified to help.

I sighed heavily and just stared into the air. “I don’t know, Twilight.”

It sure as fuck was not the answer she was expecting. Hell, it wasn’t the answer I was expecting. “*Sniff*… wh-what? What do you mean… *sniff*… you don’t know?”

Now… normally this is not something I would ever do. Maybe it was because part of my brain remembered that this wasn’t a “real” session, or maybe just the whole Derpy thing was getting to me, but… I was just frank with her. Only the barest semblance of an act.

“Twilight… can I be honest?” I asked.

Considering the way she looked, I think she was expecting me to mock her or something, but she responded anyways. “I… I guess so.”

I looked her dead-on. “I don’t know a damn thing about real relationships.”

She looked, understandably, confused. “Wh-what?” She cocked a half smile. She wasn’t sure if I was joking or not.

I continued unabated. “I’m totally serious. I’ve never actually been in a real romantic relationship.”

She kind of gawked at me. Her face quickly became a mask of disbelief. “That can’t… that can’t be right. You’re so… good at this.”

“Yeah well… lots of tutelage and years of practice have made me good at helping ponies with their problems. But… I don’t actually know how to deal with any of it.” I physically relaxed. I leaned back on my fore hooves and stared at my ceiling. “I’ve never actually had to handle any of those problems. I’ve never been in a fight with a lover. I’ve never had to lose a fight on purpose just to stop somepony from shouting. I’ve never had to figure out just how much I love somepony. I’ve never had to break somepony’s heart.” I could’ve kept going since I have a literal decade of experience with other ponies’ problems. “So, I could feed you lines about finding yourself, and figuring out what you want out of a relationship and a dozen other things. But, in all honesty… I am the wrong pony to ask about love.”

Twilight was just flabbergasted. Maybe she was expecting a long winded speech about sticking things out, or a deep intellectual conversation about standing up for oneself. But, whatever she was expecting, it was not this. This was Guilty acting like kind of a dick, and maybe feeling a little sorry for himself. This was not quality escorting. I kind of realized that a moment too late.

She seemed to be at an utter loss for words, and figured that I needed to apologize for that. “Sorry.” I scratched nervously at my neck. It was real nervous, not the fake nervous I’d given her last time. “I’m just… trying to figure some stuff out right now. I didn’t mean to… rant.”

“Nonono, that’s perfectly fine, I just... I didn’t even think…” She wasn’t crying anymore; it looked like I’d distracted her from her own problems for the time being. “How can you be bad at relationships? I mean, you must’ve had plenty of them.”

I nodded. “Yeah… lots and lots of fake relationships. False lovers. Timed temporary trysts. No real girlfriends. No real love. Just… acts.”

GAH! Looking back on it now I was so annoying. I sounded like such an annoying little kid. I was throwing a fucking pity party. I hate that shit. Just the thought of it is giving me an ulcer. I can’t believe Twilight put up with me.

Hell, she actually wanted to help me.

She looked concerned. “Do you… want to talk about it?”

I scoffed. “No, I… I couldn’t.”

“Are you sure?”

I opened my mouth to respond, but… I wasn’t sure. Maybe I did want to talk about it. I was silent for a time. I racked my brain trying to find a course of action that made sense to me. I was already uncomfortable with how much I’d been talking about myself, and I’d barely said anything.

An idea occurred to me. “Tell you what, Twilight. How about we… barter?”

Her eyebrow rose.

“I’ll help you figure out your relationship, and you help me work through my dilemma. How does that sound?”

“That sounds… perfectly acceptable.” She smiled.

My mind was screaming at me that this was a bad idea. I don’t talk… to ponies. ‘Guilty, you could always just talk this over with Croo— Okay, nevermind, that’s a bad idea. Save that for an occasion where you desperately need to be called a homo.’

“Okay then…” I cleared my throat. This was wrong. It was so wrooooooong. “You’re trying to figure out if your relationship is falling apart or not, correct?”

Her ears flattened on her head. All her emotions were back. The worry, the stress, the almost-crying.

I think Twilight and I are kind of similar. We can compartmentalize. As long as something else is on our minds we can kind of push our emotions off to the side.

Seemed like it, anyways.

She wasn’t as teary this time, but equally sulky. “I… I just don’t know.”

“Well why don’t we start with what the problem is? What specifically does he do that make you upset?”

She sighed, still staring at the table. “A lot of things, actually. He picks fights sometimes. He gets upset when I talk to other stallions; he’s really jealous.” She began to scowl. “He never picks up after himself. He shouts… all the time. He wants to go out all the time, but whenever I recommend a place he shoots it down. And then when I ask him where he wants to go he just says, ‘You pick.’ And I’ll say, ‘I’ve been trying to pick, you’re just saying no to everything!’” She actually began to yell.

“Okay, Twilight, rein it in. No need to shout.” She instantly blanched. She looked mortified. I got the feeling she wasn’t terribly used to feeling this frustrated with somepony.

“S-s-sorry.” ‘Aw… she’s so cute when she’s freaking out.’

“Don’t worry about it. Now… what about some upsides? Why do you like him? What makes you want to stay with him?”

It was like I’d flipped a switch. She immediately started beaming, whether she knew it or not. “He’s…*hehe*… he’s really funny; he can always make me laugh. He’s handsome. He likes to read; I love just sitting and reading with him. He likes to stargaze; that’s actually how we met. And he’s smart, very smart.” She’d painted quite the picture.

Clearly, Twilight really cared for this stallion. Now, one might think that’s all it takes to make a relationship work, but honestly, that’s just one of many things you need. Ultimately, I could not make this decision for Twilight, only she could really know if this stallion is right for her. All I could do was help her... discover her feelings.

“How’s the sex?” I asked straightforward.

There was that heartbreakingly cute blush again, all the way up to her ears. ‘Celestia, she is precious.’ “H-he’s very… gentle.” She sounded happy about that. That might be a turn off for some mares, but clearly it was what Twilight was looking for.

“So he makes you feel good? Physically, I mean. He manages to bring you to climax?”

She nodded, eyes dead set on looking at anything but me. “M-most of the time.”

“Okay.” I cogitated for a moment. The next step is a tricky one. Getting a client to figure out precisely what it is they want can get messy. It’s all too easy to accidentally set somepony’s standards far too high. After some internal debate, I decided that with Twilight the best way to go about it was to be as objective and methodical as possible.

“Alright, Twilight… I want you to answer a simple question for me. Why do ponies date?”

She brought a hoof to her chin. “What we would consider ‘dating’ is actually a fairly recent societal development, historically speaking. Modern dating can most likely be attributed to—”

I couldn’t help but chuckle. “I’m not looking for a term paper, Twilight. I mean what motivates ponies to date? Why do we seek companionship?”

She had to think a little more about that one. Once again, she had quite a wordy answer for me. “Ponies seek companionship so they can reproduce. Every species has to produce offspring; we’re attracted to other ponies so that we can mate and have children.”

I rolled my eyes jokingly before cracking a smile. “Well if you’re just determined to be academic about this...”

“It kind of makes this easier,” she admitted.

“Fair enough. In that case, I’ll just have to debunk your theory.” I cleared my throat meaningfully. “While I agree that that is the case, Twilight, what you are describing is sexual attraction. I am asking why ponies couple themselves. Why do many of us choose to spend their lives with one single pony?”

“I…” I could see the gears turning in her head. “There’s been lots of research on the subject of love. Some theories say that love is actually ‘healthy’ it promotes all kinds of biological—”

This was getting a little silly. “So you decided to start dating because it was ‘good for you’?”

“No, I…” She blushed again. “…I did it because I thought it would be… fun. I thought it would feel good to… to have somepony.”

“Exactly,” I explained. “You dated because you thought it would make you happy.”

“I…” She began to retort, but quickly lost momentum. “…Yes. I would say that... that is correct.” So far so good.

“Okay. So then, what can we assume is the ‘goal’ of a relationship? What should a relationship logically ‘do’ for you?”

She was beginning to catch on. She could see where I was leading her. “A relationship… should make you… happy,” she concluded.

I nodded. “That’s my belief. Would you agree?”

Once again the gears turned in Twilight’s head. “I think it’s safe to conclude that yes, ideally, a relationship should serve to improve your quality of life. In other words… it should make you happy.” Now she was on board, this was working fairly well.

“Okay then, now that we’ve justified that fact to ourselves, I think the next step would be to determine if your relationship does or does not ‘improve your quality of life’.”

Twilight did her best to maintain a professional air. She still groaned a bit. “That seems like the… *sigh*… most logical course of action.” All this fancy wordplay was really just to get Twilight to accept that she had to keep her own interests at heart. Getting a mare to believe that can be more challenging than one might think. Thankfully, Twilight was more than willing to accept a logical argument. “So, how would one… you know… assess that?”

“Well,” I began. “One thing ponies do is write out a list of the pros and cons of your relationship. Whichever list is longer gives you your answer.”

Twilight squinted. “That sounds woefully inaccurate.”

I chuckled. “Well, perhaps you can come up with a more… comprehensive analysis,” I offered.

She nodded. “I’ve got something roughly in mind. Some very basic calculus should give me a better idea of precisely how much my relationship improves my day-to-day life,” she explained.

“I’ll take your word for it.” I don’t have much of a mind for math; I wasn’t ready to talk calculus or whatever.

“Okay so… if I determine that this relationship isn’t making me happy… I should end it, right? Seems simple enough.”

“Well, let’s not get ahead of ourselves, Twilight.” No need to give a guy the axe without giving him a chance at redemption first. “Just because your relationship isn’t improving your quality of life, doesn’t mean that it has to end.”

She seemed confused. “Isn’t that exactly what we were discussing, though?”

“Well, there’s still another option to consider.”

Her ears perked up at that. “And that would be?”

“Improving the relationship itself,” I explained.

She mulled that over with a slight scowl. “That sounds… challenging.”

“Who told you love was easy?” I teased.

“A fair point.” She brought a hoof to her chin. “What exactly would you suggest? How would I improve my relationship?”

“Well, I can’t really speculate on that.”

“Oh?”

I brought my hooves together pensively. “There is no universal treatment for a bad relationship. What helps you and your boyfriend get along better is going to be specific to the two of you. Without a great deal of information, I can’t begin to form a hypothesis.” I was kind of getting into the whole ‘academic discourse’ thing we had going on. It was actually kind of fun.

“Understandable. And I do get your point. Just because a relationship might be faulty now…”

“...doesn’t mean it will always be,” I finished for her.

She grinned. “I think I actually have a plan as to how I’m going to deal with this,” Twilight said.

“Feel better?” I asked.

“Yes. Just having a plan makes things… a lot less stressful, *hehe*.” That lack of stress certainly showed; she’d visibly relaxed quite a bit.

“Okay, so… your turn?”

I groaned. Talking about this shit still just felt… wrong. “*sigh*… I guess so.”

“Well then… what’s going on, Guilty?” she asked.

‘You can always stop now, Guilty. No real reason to keep this up.’

I cringed. Everything about the whole ordeal telling me that what I was doing was just wrong. Should I back out now? Should I go through with it. There was so much I shouldn’t have done already. Was I past the point of no return? Or would this be the straw that broke the camel’s back?

‘Ah, fuck it!’

“Well, lately… in fact only since last night… I’ve sort of been feeling like… I’m… falling for somepony.” It just felt gross saying that. The words were like vinegar in my mouth, just… sour.

Twilight wasn’t following. “And the problem is…?”

“It’s a client.”

She winced. “I can see that being complicated.”

I nodded solemnly. “Yeah.”

“So you only just came to this conclusion, correct?” she asked to clarify.

I nodded. “I spent the evening with her and some friends of hers. When I dropped her off back at home… I realized that… I kind of loved her. I felt like… I missed her already and she’d only just left. I… I wanted to spend more time with her.” Difficult as this was I was doing pretty okay for myself. My breathing was slightly labored, but that was just me struggling with the whole “talking about my feelings” thing. “I still want to spend more time with her. I want to go see her right now. I just want to… be near her.” These facts were becoming evident to me just as fast I was saying them. I hadn’t really had all that much time to ponder this. Not even twenty-four hours.

“You said that you’d never been in a relationship, right? So this has never happened before?” Twilight, Celestia bless her, was putting up with my bullshit in stride. She was doing her best to actually help me.

“This would be the second time I’ve fallen for a client.” That wasn’t entirely true. Strictly speaking, Sunny wasn’t a “client.”

She looked curious about that. “What happened last time?” she asked curiously.

“I moved to Ponyville,” I said tersely. I was already talking about my current problem with her; I sure as fuck was not going to talk about Sunny.

She made an “oh” face. To be clear, that is different from an O-face.

Ha… sex humor again.

Twilight cleared her throat. “So then… what is an escort supposed to do when they fall for a client.”

“Stop falling.” That was usually the routine as I understood it. If you started falling for a client you stopped seeing them, better for a stable to lose a client than lose a whore.

“That seems… harsh,” said Twilight with a scowl.

I shrugged. “It is what it is.”

“So… that’s it? You’re just going to stop feeling that way?”

For a few moments I was silent. I didn’t have anything resembling a plan yet. I didn’t know what I really wanted. I was still adjusting to all this. “Honestly… I don’t know. Part of me feels like I should just tell her that I can’t see her anymore. Part of me wants to just keep it hidden away forever. But at the same time…” I swallowed. “…I’m my own boss now. I don’t work in a stable. I could… I could actually try. I could actually try to be with her.” Is this how I really felt? Is this what I wanted? Did I want to… go for it?

“Hmmmmm...” Twilight rubbed her chin. “That’s… that’s a multivariable problem if I ever saw one.”

“Again, I will take your word for it.”

Twilight giggled. “I just mean it’s complicated.”

I nodded. “That, it is.”

“Well, if you’re unsure as to whether or not you want to actually pursue a relationship. I think your best bet would be to run a standard risk-reward analysis,” Twilight eagerly explained.

I raised an eyebrow. “You say that like I know what it is… and that it’s a thing I can do.”

Twilight laughed and waved her hoof. “Oh, don’t worry. It’s really very basic math. You just assign a hypothetical ‘level of risk’ to each potential outcome, and—”

“Twilight, I dropped out of high school.”

She seemed shocked at that prospect. Ponies often are. I’m fairly well-spoken, but most of that can be attributed to all the training my Madame gave me. Math was never really a priority in the whore house.

“How... I don’t… oh my gosh.” Utterly shocked apparently. She was clearly having trouble wrapping her head around that one.

“Do you have any laypony’s terms for me?” I asked, so as to snap her out of her befuddlement.

“What? Oh… uh… maybe… gimme a second.” I could tell she was trying to come up with a way to explain her idea to me while simultaneously trying comprehend the fact that I had not finished school. “The basic concept,” she explained, “is to weigh each potential outcome from every possible course of action and determine the “best” possible course of action.”

“That honestly just sounds like thinking about it,” I admitted.

“Weeeeelllllll… without the math… I suppose that’s kind of all it is.” Her face fell. I got the feeling she didn’t think she was helping.

To be honest, though, she was helping. Telling me to think about it was good advice. I’d been so worked up because of everything I’d forgotten that… there was nothing actually happening. I had all the time in the world to think things over. I had time to weigh my options, and more importantly she kind of helped me realize that I wanted to. This wasn’t just some problem I had to solve, this was an opportunity.

Maybe… just maybe… Derpy and I could be happy together. Maybe that was… is... a thing that could happen.

“Thank you Twilight. I think I know what I need to do.”

I caught her by surprise. “Really? You have a plan?”

“Yes. I’m going to think about it,” I stated.

Twilight looked unsure. “I’m not going to lie. That doesn’t sound like much of a plan.”

I shrugged. “It’s more of a plan than I had an hour ago.” I actually grinned. “Thank you, Twilight.”

“B-but I didn’t do anything,” she insisted.

“You sat and listened. You offered advice. That’s usually all it takes.” It’s true. Being a good listener is about sixty percent of what I do.

That’s a rough estimate.

“I guess... Well, looks like we both have some homework to do, hehe.” She suddenly blanched. “You… You do know what homework is, right?”

“Oh for fuck— Yes, Twilight, I know what homework is,” I deadpanned.

“Right, right, *hehehe*.” She chuckled nervously again before standing up. “Well, thanks for everything. I should probably go, though. You’re expecting somepony?”

“Yes, that would be best, I think.” As I moved to stand, something suddenly occurred to me. “Oh! Before you go, there was something I’ve been meaning to ask you.”

“What about?”

I was glad I’d thought to ask her about it now. I would’ve been so upset later if I’d forgotten. “A while ago, I was hiking. I came across these… hovering manta rays flying through Ghastly Gorge. Do you have any idea what those might’ve been?”

Her face twisted in confusion. “Were they big grey things?”

“Yeah, that sounds right.”

She shook her head. “That can’t be it.”

“How so?”

“That sounds like mantle rays. But, Ghastly Gorge is not where you should be seeing them,” she explained.

“Mantle rays?” What a delightfully punny name.

“They only live in active volcanoes. They’re magma divers. The only volcano in Equestria is Smoky Mountain. I’ve never heard of them being spotted anywhere else. Maybe it’s an undiscovered migration pattern. It might even potentially be a new species!” Twilight seemed giddy with excitement. “I need to investigate! This could be a major biological discovery! Oh my gosh, I need to go. I have to prepare!” She hastily began making her way out the door. “Thanks again, Guilty. For everything.”

“You too. It, uh… It helped to have somepony to bounce things off of.” I’m not used to thanking clients. It felt weird. Not bad, just weird.

We said our goodbyes and Twilight left. The worry didn’t return when she took off, which was good. Realizing that there was no real deadline, no pressure, no risk of getting caught... it really helped.

So, there I was waiting for Crook to get back. I figured there was no time like the present to try and… well… think. So I thought. I considered. I contemplated. I meditated. It was very therapeutic.

That day I just thought about Derpy in general: what I liked about her, why I liked it, why it made me happy, why it made me want to be with her. There were many muffin related thoughts; those made me hungry… and slightly aroused.

Am I developing a muffin fetish?

A worrying prospect.

Eventually, Crook got home. “Your honor has been defended!” he proclaimed as he burst through the front door.

I could feel a headache coming on. “What did you do?” I asked, feeling an awful lot like a mother about to scold her child.

“Well,” he began, “the two of us had a lovely little lunch date. We ate. We talked. She’s actually pretty nice when she isn’t a fuckin’ bitch.”

“Crook… what did you do?” I intoned.

Crook smirked. “Well, what happened next was pretty fuckin’ great. She actually invited me to her place… to her barn… to the loft… where nopony would bother us.” Crook smiled luridly.

My jaw actually dropped. “She offered?”

“She offered,” he confirmed. I could not fucking believe it. For somepony who makes a point of being the avatar of classical values, she’s apparently pretty loose. I mean, offering an honest to goodness afternoon delight after one date? What a slut!

What a hypocrite!

‘Relish it later, Guilty, you still have something to establish.’

I quickly remembered myself. “So, Crook. What. Did. You. Do?”

“Well…” He could barely contain his smile. “…when she offered me this little afternoon fuck, I casually assured her that my prices were very reasonable. You know, I think I might’ve said it kinda loud. I kinda had to, though, the bakery was just so crowded.”

I was almost in awe. “Oh, Crook. You beautiful stallion, you. Please tell me the whole bakery heard you.”

“Even the big broad behind the register,” he assured me, a self-satisfied grin on his face. “You’re welcome, Guilty.”

I won’t lie; I was pretty satisfied with him, too. All the things he could’ve done? That was about exactly as far as I would’ve liked him to take it. “So what did she do?” I asked eagerly.

“Well first she just asked me to repeat myself. The look on her face was just so… so fuckin’ perfect. Then she just turned beat fuckin’ red and stammered angrily for about a minute. And then she just stormed off. Didn’t even pay for her pie. Oh that reminds me, I forgot my bits so I started a tab for you at the bakery.”

“They let you take out a tab? At a bakery? Do bakeries even keep tabs.”

Crook just laughed. “They do now.”

I rolled my eyes. Okay, not a hundred percent perfect on his part, but fuckin’ A! This was beautiful. Considering how many ponies were there, Applejack was going to get a taste of her own petty, gossipy, small-town, medicine. I couldn’t have asked for a better play on Crook’s part.

“Well Crook, I think you’ve earned a reward for your hard work.”

“Yeah?”

“Yeah… haircut’s on me,” I teased.

Author's Notes:

Well, there you have it.

Thanks as always to aquapunkchick, Blackskulls, coandco, and Jake the Army Guy.