I had an interesting day today; it was sort of full of surprises. Derpy’s session was today and… well, I’ll just get into it.

This morning was hectic, and I’m still not exactly sure why. I’d had the whole night before to clean and tidy and yadda yadda yadda, and I’d gotten everything done, but that morning nothing seemed… done. The dishes had water spots. The bed sheets weren’t quite straight. The floor had gotten dusty. The downstairs clock was running fast. The fireplace needed cleaning out.

Oh, and note to self, that plastic ivy on the fireplace is starting to show its age; it’s a bit melted and frayed, so I took it down. I need to buy some more, soon.

To sum up, though, it just felt like nothing had been done quite right. I fretted about for a couple hours, just… fussing... perfecting.

When the knock came I had a miniature heart attack. I wasn’t done. Nothing was ready. Everything wasn’t up to par. My whole house was…

...fine. My home was immaculate. Dumbfounded, I searched my surroundings for all the errors I had been convinced existed only a moment ago, only to find my little cottage as clean as it had ever been.

As I stood there, somewhat stunned, the knock came again, followed by Derpy’s voice. “Guiltyyyyy! I’m heeeeeere!” In that moment I realized what had been happening. I was panicking. I was panicking because It was the first time I’d seen Derpy since…well… since I figured out how I feel. “Helloooo?! Guilty?!”

‘Derpy’s still waiting for you, buddy.’

I almost slapped myself as I immediately stepped to my front door. I opened it, admittedly, a bit too fast. Derpy recoiled in surprise. “Sorry, I was in the bathroom,” I lied, reflexively. Why did I do that? Why did I feel the need to make an excuse?

Ugh… I’m second guessing everything right now.

Derpy didn’t mention anything about my obvious haste. I’m not sure if she was being polite, or just didn’t think anything of it.

Right there. Second guessing everything.

“That’s okay!” sung Derpy with a warm smile. “Come on, it’s time for sex!” She marched happily inside, picnic basket of heavenly baked goods in tow. She almost forgot to put down the muffins as she eagerly trotted to the bedroom. She stopped short, though, when she realized I was still standing at the front door. She smiled at me with a cocked head. “Come on, Guilty.”

I snapped out of my… daze, I suppose, and made a quick recovery. “Sorry, I just got distracted by that brilliant rear-end of yours.”

Not my best work, but she giggled, nonetheless. “You’re so silly, Guilty. It’s not that great.”

I scoffed. “I think you’re underestimating just how lovely it is.” She blushed at my compliment. I don’t normally bother with flattery when it comes to Derpy. She may not have been expecting it. I usually use it with newcomers or mares who need a little buttering up, and Derpy is anything but.

Still, I think she appreciated it. “Thanks, I guess. Now, come on! Let’s put this butt to good use!” She wiggled her ass at me. I couldn’t help but smile.

I was kind of expecting to… get nervous. Part of me thought I wouldn’t be able to go through with our session with all of my… inner turmoil. I didn’t, though. Things were going… smooth… like they always do. Muffins on the table, Derpy in the bedroom… everything was going swimmingly.

She propped herself on the bed as I quickly grabbed a potion and wriggled out of my jeans. Legs spread, tail up, already raring to go. It was enough to get any healthy stallion fired up. She’s really very sexy, and I’m not just saying that.

Well, I’m writing it… but I’m not just writing it, either.

I moved to mount her. “So how are things? Dinky okay and all that?”

She giggled. “Oh, I think Dinky’s got a little bit of a CRUSH!” She almost lost control of her speech as I made a gentle tap on her entrance. She was just as sensitive as always.

“Oh? That’s quite the development.” I made gentle motions up and down her lips. Here hips hungrily tried to press themselves onto me, but I teased away from her. “Your first love is an important part of growing up.”

“Oh, it’s just puppy love. She’s still a little… girl.” She was getting heated, but I continued to deny her pleasure as we conversed. Her body writhed under mine, quivering in anticipation.

“So, who’s the lucky colt? Not that I’d know, I guess. Not a lot of kids come out here, as you’d imagine.”

She giggled again. “You’re not gonna… believe it. I think it’s the boy whose… mmmmm… tooth she broke.” She was having trouble getting through her sentences. That meant it was time to take the proverbial (and literal) plunge. “OOOOoooooh, that’s nice,” she commented as I entered her. What can be said about Derpy’s cunt that I haven’t said already: warm, wet, soft. It’s everything a mare’s entrance ought to be. I suppose it’s a little loose, but she’s given birth, so…

Wow, that’s kinda trippy now that I think about it. Dinky came out of that fucking thing. Pussy is just so… very different in my line of work. At least, it feels that way.

Tangents aside, Derpy and I were just getting into the swing of things. “Didn’t you say that kid was making fun of you?” I began to gyrate my hips ever so slowly as I spoke. I fell back into our usual routine: casual conversation and standard sex. Derpy’s pretty vanilla, all told. Just… sex… a little oral… that’s all. I kind of appreciate it, it makes the session… easy. It gives me a chance to enjoy it a little.

“Yeah, but he… he apologiiiiiiiiiized!” Wings splayed and muscles clenched in climax. I’d barely started, but she was already beginning to have her orgasms. She’s so very sensitive.

“Well, that was nice of him.” Thrust. Plant kiss between wings. Thrust. Run hooves along flank.

“Yeah, he was really sorrryyyyyyyy!” Increase speed. Kisses along the wings.

“Oh, he apologized to you face-to-face?” Thrust. Nibble at ears.

“Y-yeah! Dinky apo… apologized t-tooooooooooooo!”

“On her own?” Increase speed.

“Yeah,” she gasped. “I… I didn’t… *huff*... maaaaaaaaake her!”

“Well that’s good.” Lay body firmly into hers. “So, when’s the wedding?”

She giggled. “Guilty, you’re so sillllllyyyyyyyyyyy!” The bedroom was beginning to reek of sex. I really do love that smell: the sour stench of sweat and pussy. It’s something I grew up with and it really… makes me comfortable, if that makes sense. “Oooh, by the way, e-everypony really liked you at… at… giiiiiiiiirl’s…” She took a few breaths before she could finish her sentence. “ … night.”

Kisses between the wings again. “Yeah?” Prop self up and thrust deeply. “I’m glad I made a good impression.” Increase pace. Make balls slap clit. “If I’m welcome, I’d love to come again.” Nuzzle from behind. “I’d hate to intrude on girl’s night too much, though.”

“It’s… hah… no prooooooblem!” She began to lose strength in her legs. She was bowing under my weight. It was time to guide us onto the bed. Lift her onto the mattress. Guide her onto her knees. Follow suit. Never let member exit her.

“Maybe I should sit poker out, though. I wouldn’t want to be ‘that guy.’”

She laughed out loud. “May… maybe.” Continue thrusting from upright position. Push her legs together. Place knees outside her legs. “Oh, and… and… I th-think you were riiiiiiiiiiiiight!”

I cocked my head. “About what?” Grip ass tightly. Pull vigorously onto member.

“G-G-Goldy. I think you make her... uncomfortable.” She was becoming incredibly warm and wet. The cold feeling of her juices ever so gently splashing on me was becoming immensely pleasurable.

I slowed down, and continued my movements at a steady pace. “Yeah? She say something?”

“N-n-no, when I… when I was taaaaaalking about that night, she said you were nice and she had fun, but… but she—” she failed to finish her sentence as her tongue lolled out of her mouth. She threw her head back in pleasure as she crested another wave.

“She just seemed uncomfortable?” I offered.

“Un-hun,” she grunted in affirmation. I stopped my thrusting, allowing her and myself to relish in her climax. Her walls clenched me as her wings flapped in spasm and every inch of her shivered. “That was a big one,” she commented with a tired laugh.

“Need to take a break?” I asked.

“Just a little one,” she replied. I removed myself from betwixt Derpy’s lovely legs and lay down next to her. The brisk air hit my member as I slid out of her.

I briefly pondered what to say next. I mean, I knew why Derpy talking about me would make Carrot Top uncomfortable, she doesn’t want to get found out. However, I wasn’t supposed to know that. I thought that the least conspicuous thing to do would be to spitball ideas off of Derpy. “Do you think she has a problem with what I do?”

Derpy pulled a hoof out from under herself and brought it to her chin. “Maybe. She did seem kind of upset when I told her I was seeing you. Remember? That day at the market?”

I did remember. “I guess… I dunno, maybe I just rub her the wrong way.”

“Well, don’t worry. I’m sure you two will be friends eventually.” ‘Heaven forbid.’ “Lily seemed to like you a lot though. She said you were awesome.”

Even in repose, an escort’s job is not done. Trace hoof delicately along side. Nuzzle affectionately. “Yeah?”

“Yeah, she said you were ‘such a gentlecolt.’” She responded to my cuddling in kind, allowing herself to sink into me. “I told her if she liked you so much she should make an appointment.”

My stomach churned at the notion. I honestly don’t think I can imagine a more awkward situation. “Does Lily even go for stallions?” I asked.

Realization seemed to dawn on her. “Oh, probably not, huh? I didn’t think about that.” She shrugged. “Oh, well. Her loss.”

I snickered. “Well, I’m sure she would say the same about you and mares. Or, do you go for mares too?” I’d never taken the time to ask her that. I was curious.

She shook her head. “Nah.” She pressed herself into me with renewed vigor. “This is all I need.” She proceded to press her behind onto my still erect stallionhood. “Well… maybe this too.”

“Ready for round two?” Whenever I ask Derpy that question , it’s… different. It’s not a sly suggestion. It’s not a seductive maneuver. It’s not a tactic. It’s just a question. I’m curious if she’s ready for more. It’s just simpler with her.

“Uh-huh!” she replied in that warm, mirthful voice of her. She raised a leg high. “Like this okay?”

“Of course,” I responded. I slid myself into posiiton. The Sensual Spoon, as it was introduced to me, is fun position. It’s sort of a sideways half-mount. It’s not very easy, but worth it, in my experience. It’s more of a position for the mare’s benefit, to be fair, but that’s all that matters in a session.

And in general, in my opinion.

I thrust into her again, her insides as welcoming as ever. “I like this one, it’s fun,” said Derpy as she did her best to hold her leg high. “It’s kinda hard, though.”

“Well, it never takes very long to make you feel good, so it shouldn’t be an issue,” I teased as I began to pump slowly.

“Hey, shut uuuuuuuuuup!” she said in ecstasy, proving my point perfectly.

“I’m not even gonna say ‘I told you so.’” Increase pace.

“You… you just diiiiiiiiiid!” Orgasm upon orgasm took hold of her body. Juices spilled out of her and breath became labored. Sweat soaked her coat, and and she struggled to keep her form.

“I suppose I did.” Assault the spot between the wings with tender kisses.

“You’re... so… silly.” He words were coming in sputters and and grunts and my further attempts at conversation were met only with vague moans of pleasure. After several minutes of raucous fucking I blew my load inside her, and the two of us collapsed in a heap. As I pulled myself out of her, my jism dripped from her lips, staining my sheets. “That was fun,” she said. “Wanna lick me now?”

‘Yes, please.’ “Sure thing.” Before I could grab hold of Derpy’s hips and dive into her sweet folds, she stopped me.

“Hang on. Lie on your back, I want to try a thing Lyra told me about.” I eagerly obliged, fairly sure I knew where this was going. Sure enough, Derpy climbed on top of me and thrust her hips into my face. Just as I began to lick with vigor, I felt Derpy lean forward and wrap her lips around my firm stallionhood.

Bliss.

She’s gotten so good at that since she started coming to me. When she started out her technique was… well… not bad, but… lacking. Over the course of two years she’s gotten pretty good at working the pole, so to speak. I’ve never coached her, or told her ways to improve, she just… learned. I like to think that means I’m having a positive influence of sorts.

I let out a low moan. Derpy had apparently never heard of a sixty-nine before. Needless to say, I could not be more pleased. Her mouth enveloped my member. My tongue plunged into her depths. I reached up and grabbed her haunches. I pulled her firmly onto my face as I vigorously licked at her with fervent intensity.

I indulged deeply of her flavor and her scent and her movements, and she delighted herself with my rod and my tongue. There’s a reason it’s called “eating” somepony; you are partaking of their very body for your own pleasure and gain.

But it’s also called “giving head”, because you give just as much pleasure as you take. Truthfully, I like to think I give more than my fair share. This was evidenced by Derpy’s biggest climax yet.

Her legs fought against the bed, wrenching her from my grasp. Without so much as thinking, my muzzle chased after Derpy’s delicious slit . As I connected with her once again, I could feel myself reaching my own climax. I basked in pleasure as I continued to eat my way through Derpy’s uncountable orgasms.

All at once Derpy’s back arched and her wings flared. She stopped her eager sucking just in time for me to spill myself all over her face as she withdrew. She clambered off of me, and crawled onto the sheets, writhing. Her limbs pressed into the sheets, as she scrambled about in what appeared to be panic.

I was suddenly rather concerned. “Are you okay!?” Okay, perhaps very concerned.

“C-c-coming! So m-much comiiiiiiiiiing!” she cried. Several seconds passed as I debated taking some course of action. Unfortunately, all I could really think to do was ask if she was okay again. Thankfully, Derpy’s…well… fit subsided in due time. Eventually all her flailing and spasming died down, and Derpy melted into a puddle of very exhausted mare. “I… that… tired,” she groaned.

I managed to swallow my worry, and put a semblance of an act back onto my face. “Need a nap?” Smile.

She nodded and proceeded to curl herself into a ball. “Nap,” she parroted with a yawn. Positively adorable. Within moments she was snoring quietly. This wasn’t the first time this has happened. Sometimes Derpy needs to knock out after a mind-shattering orgasm.

So, I decided I’d do what I always do when Derpy sleeps. I’d shower quickly and cook her something to eat. Yes, we had muffins, but I could turn a midday snack into a meal with relative ease. Derpy thinks I’m a good cook, apparently. She told Carrot Top as much.

I cleaned up quickly, and took stock of my kitchen. I had a rather poor selection of fruits and veggies, actually, which was unfortunate. I did, however, have quite a few flowers, so I decided to make a nice little bouquet salad.

I steamed some tulips and what remained of my carnations. I figured something light would help to balance out the heavy banana muffins Derpy had promised. That and the savory carnations would nicely compliment the sweetness of the banana.

I tend to overthink things, don’t I?

I really like cooking for Derpy. She’s always so appreciative of whatever I make. She tells me how delicious it is with a great big smile and she means every word. I wonder if Dinky would like my cooking.

Why am I thinking about Dinky?

Anyways...

I was looking through my cabinets for plates when Derpy stumbled out of the bedroom. Her face was still caked in seed; her hair was a turbulent mess. “Morning,” she mumbled, eyes still closed.

I chuckled. “It’s not really morning, Derpy. It’s almost noon.”

She brought a hoof up to rub her eyelids, which really only served to smear the semen into her coat. “Noon?” Her eyes shot open. “Ohmigosh, I’m late!” she cried. Before I knew what was happening, she was running full tilt for the front door.

Derpy’s lucky my reflexes are as good as they are, otherwise she might have flown through town with a face covered in… well… me. “Sunday! Derpy, it’s Sunday!”

She tried to stop when I shouted, but momentum carried her forward into my door.

Head first.

*THUNK!*

“Derpy!” I almost dropped the plates as I rushed to her aid. “Are you okay?!” She hadn’t fallen, or anything, but her head made a pretty nasty noise against that hard wood. I just wanted to make sure she was okay.

She held a hoof firmly on the top of her skull. “Ow…” she groaned, before voicing a cheery “I’m okay.” She smiled up at me. Truthfully, she was sort of a mess: wincing in pain, hair like a homeless person, a face coated in juices. If anyone were to walk in right then, things might not look so great for me.

“Are you sure?” I was really worried about her. She might have been bleeding, after all.

“Yeah, I run into stuff all the time. It’s no big.” She casually waved a hoof as she sniffed the air. “Oooh, what smells good?” she asked hungrily.

I was mentally debating if I should insist that I examine her head, so my response was a bit delayed. “Just steaming some flowers. I figured they’d be good with the muffins.” Not this time, she seemed fine, at least.

“Smells delicious,” she hummed with a lick of her lips. She paused before licking again, seemingly confused. “Do I have semen on my face?” she asked, totally candid.

I couldn’t help but giggle. “Yes, Derpy. You have semen on your face. You may want to take a quick shower.”

She nodded in agreement. “Okay, but don’t eat without me.”

“I won’t,” I assured her as she trotted up the stairs.

I poured us some tea and finished the flowers while she was showering. I made everything look nice pretty, as an escort should: set the table, arranged the dish everything nicely, cut the stems off...

Yes, I cut the stems off of my flowers. No, I am not a child. I know it’s kind of like cutting the crusts off of sandwiches, but…

… fuck stems.

Everything looked lovely by the time Derpy came down the stairs. Her transformation was astounding; she was glowing compared to before. Her dripping wet mane, her powerful smile, it was enough to put me at attention again.

And, that fucking smile; her glee is almost infectious.

Oh, who am I kidding? It is infectious.

“Wow! That looks really good, Guilty” ‘Not half as good as you do.’ I actually thought that. When did I become so corny?

I shook the kernels from my head (Ha.) “Well, dig in. There’s plenty to go around.”

We both took our seats and feasted. The flowers with nice and tender; they all but fell apart in my mouth. The tea was perfect and piping hot. It was a wonderful little hot meal on such a cold day.

I am going to make a point of not describing Derpy’s muffins.

It does things to me. When all was said and done, the two of us were thoroughly satisfied. “How were the flowers?”

“They were yummy! I love steamed carnations! You’re such a good cook, Guilty.”

It felt… really good to hear that. It sort of perked me up just hearing her say it. She says that every time, but… I dunno… it seemed different. Logic denotes that it’s because I’ve discovered feelings for her. Such feelings would surely make a compliment such as hers especially moving. Yes. Quite.

Ugh… feelings.

I started thinking again. I still haven’t decided whether or not I’m going to attempt to pursue a relationship with Derpy and I was wondering if… if this is what our days would just be like. Waking up to casual sex and a hot meal, smiling at each other from across the dinner table? Would I cook for her every day? Is that what a relationship would be like? Of course, it would be more than that, and not all good. What would our fights be like? Would she just slug me like she had Applejack? That was a terrifying thought. I’d fall like a house of cards. Oh, geez, would I be a battered stallion? No, that was ridiculous. Derpy’s not like that. Would the sex change? I imagine not, it already pleases both of us quite wonderfully.

“So, Guilty, I was wondering if you’d want to go on a date with me.”

Would…

Wait, what?

If I was holding something I would’ve dropped it. I just sort of… stared at her. She had the same innocent smile she always does. That same gleeful expression adorned her face, as though what she’d said was perfectly normal.

‘But then again, isn’t it? I mean it makes sense. I’ve been seeing her for a while now; we’re pretty close. I mean if she’s asked her hairdresser out, asking me out isn’t too far removed from that, right? This is happening. This is actually happening. I guess it’s my turn to—’ I stopped. I stopped my train of thought before my little fantasy got any bigger. I kept my hopes from rising any higher as one very simple fact occurred to me.

‘My luck’s not this good.’

I kept my smile from cracking as I asked her to clarify. “How do you mean?”

She blushed a little, clearly embarrassed for some reason. “Well, it’s been a while since I’ve actually succeeded in asking somepony out. I figured I could use the practice. Would that be okay?” Big happy smile. Ears up and full of joy. Darling mismatched eyes.

A smile that pretty should not have been making me feel so... empty. ‘Answer the question, Guilty. You can’t just leave her hanging.’

I tried to answer. I really did, but the words literally died in my throat.

‘Just… just answer okay? It’s not gonna be fun, but you gotta fuckin’ do it.’

I found my tongue a bit later than I would’ve liked, but not so late as to arouse suspicion. I almost gave my default answer of “that falls outside the purview of our relationship,” but… but where would that get me? I gave her a half-baked excuse.

“Well, I’m not opposed to the idea, Derpy, but I’d hate to cause that much trouble for you.”

‘Nice try, but that’s not gonna satisfy her and you know it.’

She cocked her head. “Trouble?”

“Well…” I was still constructing my excuse. “… I mean if it was in a public place, it might look bad.”

She scoffed. “I don’t care who sees me with you, Guilty. You’re my friend.”

I was sweating. I’m not sure why I was so desperate to get out of this, I just was. “Well, I mean with Applejack and all that—”

“Fuck Applejack!” ‘She’s been saying that a lot lately.’ “I don’t care what she thinks.”

“Well, I guess….” ‘I’ve got nothin’. You’re gonna have to go. Sorry, buddy.’ “…how’s tomorrow night?”

“Works for me! Pick me up at seven?”

“Sure thing.” ‘Don’t let that smile fall, Guilty. That’s lesson one.’ “How should I dress?”

She shrugged as she searched through her little picnic basket for her bits. “I dunno. Something handsome.” Out came the bits, and onto the table they went. “I should get going, though. See you tomorrow, Guilty!”

‘Only a few more seconds, keep smiling.’ “See you tomorrow, Derpy.” Out my door she went. Twenty paces. Turned back. Waved. Kept walking.

I closed my door. I needed to clean. I needed to keep my mind occupied, anything to keep myself from thinking. I wasn’t totally successful. Even with all the dishwashing and bed-making and dusting I managed to do I couldn’t help but come to two very annoying realizations.

First, going on this date knowing that it won’t actually mean anything is going to suck.

Second, the fact that it’s going to suck so much probably meant I’d fallen for Derpy pretty hard.

‘Ugh… why do I do this?

‘Why do I just fall for ponies like this? Granted, it’s only really happened twice, but that doesn’t make it any less…

‘Annoying? Troublesome? Stressful?

‘I don’t know. Maybe I just… over-worry things. Maybe I don’t actually fall for ponies, maybe I worry that I’m falling and that makes me think about the pony in question and that makes me think I’m falling because I can’t get them off my mind.

‘Does that count as a vicious cycle?

‘I think too much, don’t I?’

A knock at my door ended my internal monologue.

As a side note: why does that keep happening? Is this normal in a small town? Do ponies just come and knock on your door? Is that a neighborly thing? Well… I don’t really have any neighbors I don’t think. Townmates, then? Is it townmately?

Regardless, I answered the door with a smile. Appearances, appearances.

Corded red muscles bulged under a thick red coat. If not for the color I would’ve thought Crook had come back to town already. I swallowed as Big Macintosh’s frame cast a literal shadow over me. “Um…” ‘Don’t think about him. Don’t think about his powerful weight on your back. Don’t think about his fat, thick member penetrating you. Don’t think about his hot breath on the nape of your neck. Don’t think about the taste of his cock. Don’t think about the smell of his sweat. Don’t think about it.’ Images assaulted my mind. In panic I said the safest words I could think to. “… I don’t… I don’t take stallions.”

The giant of pony blushed furiously, which, honestly, served to calm me down a little. “A-Ah Ain’t…” he stammered, his voice a bit higher than what I’d normally heard at his little apple stand. ‘Good. Nervous is good. Keep him in your pace.’ “Mah… Mah sister…” He stopped and shook his head. I began to notice him shivering. Escorting instinct told me invite him in out of the cold, but I decided against it. “Ah’m lookin’ fer yer friend,” he said finally.

“He’s gone,” I responded tersely. I had a good idea roughly what this was about, already: retribution in some form or another. “Back in Manehattan, he caught the train a few days ago.”

He sighed almost imperceptibly. “That so?” I could already see him beating himself up. He clicked his tongue. “Dangit.” His eyes spoke much more than his mouth. I could see that he did not want to be here. Was he here at Applejack’s behest? No, if she was going to send him to… do whatever he’s here to do, she would’ve done it right away. It had been almost a week at this point. So, he was here on his own. Against his better judgement, maybe. What did he want, then?

I pondered. I wanted to dismiss him, honestly. I was being so rude to him, looking back. I think I just wanted him and the graphic mental images the followed him to leave. I just wanted this little encounter to be over.

But then I realized how big of an opportunity this was. Presumably, Applejack’s brother was someone close to her. If I could… well… if I could get him on my side, that would be a powerful play.

Conniving won out over uncomfortable, and I changed my tactic as well as my attitude. “Well, come in. It’s fifty below out here.” I suppressed a swallow. Something about being all alone, so far away from anypony that could help. When I’m with a mare I worry less, I suppose. It’s just… if he wanted to kill me… he fucking could. No clients. No Crook. Nopony for a literal mile.

Back in the stable, we had ponies for that. Security. There was a bell in every room. We only rang them when we were in trouble. I never had to use one, but the knowledge of their existence was comforting.

I kept it together, though. I put on a friendly smile, adopted a positive demeanor. “Take a seat. You want something warm?”

“Coffee,” he responded after a moment’s hesitation. This was good. He clearly had qualms about accepting my hospitality. Having him out of his comfort zone put me at an advantage.

Well, I guess I was out of my comfort zone as well, but whatever.

“I hope instant’s okay!” I called from my kitchen.

“S’fine,” he called back. I put the kettle on and fetched the (frankly wretched) instant coffee out of my freezer, as well as some black tea for myself. I peeked in on Big Mac briefly before I walked back. He was taking in the surroundings, looking at my quaint little living room.

“Not what you were expecting?” I made a very pointed effort not to use any voice that could in any way be construed as sexy or seductive. “Kettle’s on, it’ll be a bit.” Big Mac was very out of his element. He was stoic, to be sure, but the telltale signs of discomfort couldn’t hide from me. Poor eye contact. A subtle swallow. The silent stallion spoke volumes.

His gaze shot away defensively. “Ah weren’t expectin’ nothin’.” Nervous shifting. He was as bad a liar as his sister.

“I’m sure.” Cocky smile. I decided to go on the offensive. Any conversation can benefit from my training, really. So long as I kept Big Mac, I could all but dictate the outcome of this encounter. I took my seat. “So, Mister Apple… or do you prefer Big Macintosh?”

He shrugged. “Anything’s fahn.” His accent was a bit thicker than his sister’s.

“Big Mac, then. I don’t think it takes a genius to know what this is about.”

Just a nod.

I rested my chin on my hooves, dissecting his every twitch and movement. ‘What’s the play, Guilty? Ambivalent? Apologetic? Flat-out ingratiatory? Play the victim?’ I cracked my neck as a dozen strategic conversational techniques occured to me. ‘ Hmm… let’s just feel it out for now.’ “So what was your plan, Big Mac? What were you going to do once you confronted Crook?”

Eyes downcast. “Ah ain’t exactly sure.” A pang of guilt.

“Hmm…” This was turning out to be a little more difficult than I would’ve liked. Big Mac was proving a hard read. Emotions are easy, but motives? Those are tricky. For the moment, he seemed content to answer my questions, so I took advantage of the opportunity. “Where do you even stand on this issue, Big Mac?”

He snorted, clearly irked. “Tweren’t raht, what yer friend did.”

“Agreed,” I lied. I felt that what Crook did was a textbook example of giving somepony a taste of her own medicine, but Big Mac didn’t need to know that.

I’m a bit of a bastard, aren’t I?

Big Mac’s eyes went wide for a moment; he wasn’t expecting that response. “But not what I meant,” I continued. “I meant on the issue of me. I don’t think it’s a secret that Applejack wants me out of Ponyville entirely. She hassles me in the streets. She refuses to sell me anything on market day. She tells everypony what an evil, wicked stallion I am.” He showed only the faintest trace of surprise. “You, on the other hoof, are decent to me. You’ve never turned me away from your cart, you’ve never said a single word against me. So where do you stand?”

Visible swallow. Twitch of the ear. Evasion of eye contact. “Ah ain’t thought much about it.” A lie.

“Well, you’ve at least decided that my bits are still good,” I joked. I wasn’t going to press him on this. It wasn’t getting me anywhere.

Before I could explore another avenue, he spoke up. “Look, ah didn’t come here to talk about all that. I was just… thinkin’ maybe Ah could talk some sense into yer friend. But he ain’t here, so—”

“I am sorry about that,” I interjected. I had to keep him talking. He could leave at any moment. “Crook can be a bit… overzealous.”

“Overzealous in tryin’ ta sully mah sister’s good name in front everypony?” Anger crept into his voice.

‘Calm, Guilty. Keep calm. He’s not mad at you, he’s mad at Crook.’ “Overzealous in trying to protect my name. While I disagree with his means, his ends are not as sinister as you make them out to be.”

Big Mac just narrowed his eyes a bit. Truthfully, it was incredibly menacing. “How’sat?” he asked.

Easy enough to explain. “Your sister has pull with the townsponies. Crook was trying to make her appear… more reproachable, so that Ponyville wouldn’t take her outcries against myself as gospel.” I actually think that I sugar-coated that quite nicely.

That said, his reaction was even better than I was expecting. “Ah suppose ah can see where he’s comin’ from,” he admitted. ‘He can?’ Where was this coming from? Prior to that explanation he was ready to rumble. What about that had made Crook seem—

Epiphany. “He’s a lot like you, you know?” I had an angle.

Mac’s ears raised.

“Crook, I mean. I’m like a little brother to him. We’re family. He likes to fight my battles for me.” This was my best play. Big Mac is clearly a family pony. After all he was out here looking out for his sister. When he’d heard that Crook was looking out for me, it suddenly seemed okay. He’s protective of his family, and I was going to use that to win some points with the big guy.

He squinted. Big Mac was having trouble making sense of what I was getting at. “Ah don’t see how—”

“Just like you are right now.” A tiny flash of panic told me I was right. “Applejack doesn’t know you’re here.” He tried desperately to find something to look at. His guilt came back in force. “How would she react if she knew you were here right now?”

“That… that ain’t…”

“I bet she’d be upset that you were butting into her business.”

Big purposeful deep breath. “A’right, what’s yer point?”

“My point is that I have just as much control over Crook’s actions as Applejack has over yours.” Time for a slight pity play. “I just don’t want anypony thinking I ‘sicced’ Crook on Applejack.”

“Ah never thought—”

“You didn’t. But what does Applejack think?” I asked.

“Ah don’t know.” Scratch at back of neck. “She’s been all worked up lately.” This was good. This was very good.

“Just lately?” I teased.

He laughed at that before catching himself. “Maybe she’s been a mite upset for a time now,” he admitted with a trace of a smirk remaining. ‘Okay, so he’s starting to warm up to me. This is good.’

“And again, I’m sorry about that. I’m not going to sit here and pretend I didn’t have a hoof in that. I’ve done a few things I regret in the course of this… little feud.” That one wasn’t a lie. I did feel shitty about that rainy night at Sugarcube Corner where I verbally eviscerated her.

Big Mac nodded solemnly. “I heard all about that one.” Meaning he hadn’t heard about this one from Applejack. Every bit of information helps.

‘Maybe Applejack feels partly to blame for what happened with Crook. Still, it’s tough to say. Too many unknowns.’

“Look, ah’m… ah’m sorry,” he said. Unexpected, but not unwelcome.

“What for?” I inquired.

“I… I assumed ya’ll were… well… ya’ll were just what mah sister was sayin’.” ‘Oh, this is very VERY good.’ “But ya’ll ain’t half bad, uh… Ah’m sorry, I didn’t catch yer name.”

“Guilty… Guilty Pleasure,” I responded, extending a hoof.

“That so?” he asked, disbelieving, as he took my hoof and shook it.

“Well, no,” I admitted. “But it’s the only name I use anymore.”

“Huh… Y’all are a character ain’t ya?” As the hoofshake ended the kettle began to whistle.

“That’s the kettle. I’ll be right back.” Off to the kitchen I went once more. So far so good. Big Mac was being amiable and, so long as I was working on winning him over, his presence wasn’t niggling at me that much. I returned to living room with our beverages as well as a small dish of crudités. Exceeding expectations is never a bad move, and it’s not hard to put cucumber and celery on a plate.

Big Mac cleared his throat as I hoofed him the mug. “Thank you,” he said, still hesitant.

“Careful, it’s hot.” As I returned to my seat, I took stock of my… well he wasn’t a client. Mark? No. Don’t want to think about that. Hmm… guest. He was my guest. Yes, that’s it.

He cleared his throat. “Thank you,” he said purposefully. Taking a sip, his body visibly relaxed. His shoulders drooped ever so slightly, and his lips curled into a hint of a smile. “S’good.”

“Thank you.” I took a sip of my tea, even though it hadn’t properly steeped yet. Hot and caffeinated, it was all I really wanted. The warmth spread through my chest as I swallowed my swill. Just the thing for a day like this. We enjoyed our drinks in relative silence. Big Mac’s not a very talkative pony, and he seemed to appreciate the quiet. He never partook of the spread I’d laid out, but the sentiment was what really mattered anyways.

When our mugs were empty, I decided to make another play. “So, Big Mac, I hope you won’t think less of me for… asking you a favor.” Feign anxiety. Fiddle with hooves.

“That all depends…” he responded. Even incomplete his statement was clear.

“I’d like you to let your sister know… that I’m sorry… for Crook, and for all the things I’ve said.” Act sincere, but also uncomfortable. Make eye contact, but blink a lot.. The more it appears it’s hard for you to ask, the more genuine your plea appears. That and the more pathetic you appear the more likely people are to take pity.

Big Mac took a deep breath. “Ah’ll do what Ah can. Not sure what good it’ll do, though.” I really didn’t care how Applejack took it; this little show was all for Big Mac. I was making myself look like an honest pony with good morals.

Not that I’m all that dishonest or immoral it’s just… well…

You have to defy expectation if you want ponies to think differently about you. The more you defy, the more different ponies think.

Hmmm… that sounds a lot like an excuse, doesn’t it.

Somtimes, I really think I might be a bastard.

Best not to dwell on it.

I don’t know. I really am sorry about what I said. That’s the truth. Crook’s little play, though? I rather enjoyed that. Maybe I don’t sympathize in the classic sense of the word. Maybe I just feel like I’m not responsible, so it’s okay. Maybe I’m not actually sorry, maybe I just feel guilty. Maybe I actually do delight in Applejack’s suffering.

Hmmmmmm…

I need a therapist.

Where was I? Ah, yes…

After his coffee Big Mac looked like he was ready to leave. I would’ve loved to try and grill him for information, but I’d rather win points than risk any with reconnaissance. “You should head out while that coffee is still keeping you warm.” I gathered up the mugs.

“Yup,” he responded, standing to his full height again. He’s pretty freaking enormous.

“Take care, now, Big Mac. Stay warm.”

He nodded, and left without a word.

Once the door was closed I couldn’t help but pump my hoof in triumph. ‘Score! That couldn’t have gone better! The brother thinks I’m an okay guy!’ I may have indulged in not-so-brief victory dance.

Could things actually be taking a turn for the better? I suppose only time will tell, to use a cliché.

That evening was one of introspection and drinking. After he was gone, the unpleasant mental images of Big Mac seemingly left with him. Interestingly enough, they sort of weren’t present once I had gotten into the swing of things. Again, I think I’m compartmentalizing. I had hopeful thoughts of a peaceful relationship with Applejack in the future. It’s a longshot, but hey, a stallion can dream.

And then came the inevitable. I began to worry about my upcoming… meeting.

Okay, date. It was a date.

I was doing what I always do when I have free time: preparing. I was running through possible conversations, debating wardrobe options, mentally prepping for possible faux-pas, running through magazines to brush up on anything I could think of topic-wise.

When the brain-racking worry became a little more than I could stand, I decided to exercise. Sit-ups and squats. The burn in my muscles was very cleansing. I’ve been slacking a little on my workout, so I was feeling more pain than usual. I need to go on a hike again soon, too. Gotta work on my cardio.

After exercise came a shower. After a teeth-chattering scrub down of the utmost thoroughness, I decided to pull a Derpy and just… meditate. Warm water is like a liquid blanket. Sitting there in the warm shower was almost enough to make me fall asleep. I didn’t, but I almost conked out. I don’t know why it’s so peaceful in the shower. I don’t think. I don’t worry. I just sort of… sit. Cheesy as it sounds, it sort of washes everything away. Maybe it’s the white noise. I need to test this theory somehow.

I almost shaved, but I decided I’d do it again before my… date.

So I wrote… well… all of this.

I…

I think I’m feeling pretty sad right now. It’s not like a… a tangible sadness, there’s no tears, no wrenching gut. It’s a sort of… low hum in the background. A song of woe playing in my life. Or, maybe it’s more like the sound of a fuse. A fizzle of depression building up to some greater unknown sadness. Further still, it might be more of a warning alarm. An internal alert of upcoming…

Heartbreak

That’s the word, isn’t it?

I… I don’t want to feel like that again. I don’t want to feel that… unwanted.

When I… I told Sunny how I felt, it was… it was instantly awful. I didn’t have to wait for her response to know what it was. The moment I’d opened my fat mouth, her face just…

Pity. It was the epitome of pity. She was looking down at me as I laid myself truly bare before her and… and she felt sorry for me. She was sorry for the feelings I had for her because she knew that they weren’t reciprocated. She pitied me…

… and I felt pitiful. I felt so small and weak and ineffectual and…

There must be a word. There must be word that means what I felt, because I felt like I was… nothing… like I didn’t exist. At that point in my life, I was aiming to capture the attention of one pony, and I had failed. It was as though the whole world couldn’t even see me.

She was so polite about it.

“I’m sorry, but I’m married. You know that, Guilty. This is fun, but… it’s not real.”

That’s all I was. Not real. I was imaginary.

She continued to see me after that. She gave me many a gift in that time. It pleased her to do so. Clothes, watches, expensive liquors, even gemstones, she gave me whatever she thought I might enjoy. She didn’t know that any gifts she gave me were sold off and the profits split between my madame and I. She didn’t know that every meeting, every date, every rendezvous was being captured on film.

I… I wanted to hurt her. I wanted her wits to fail her when the fateful letter was sent off. I wanted her to have to carry the fear that one day her unsuspecting husband to find out about her and my little tryst. I wanted her… to feel sad.

When I look back at that Guilty, I see… such a sad craven pony. I see a pony who just didn’t want to feel like he was suffering all alone, and was willing to hurt others, just to feel like he had some company at the bottom.

I don’t want to be that pony again. I don’t want to hurt Derpy the way I tried to hurt Sunny. I don’t want to hate her. I don’t want to be that small again. I don’t want…

...to write anymore.

I’m going to go to sleep.

Author's Notes:

Thanks to all the usual helpers. Aquapunkchick, JakeTheArmyGuy, coandco, and Blackskulls.

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