Today was a day. Events happened and things took place. I saw ponies and said things and engaged in conversation.

There. I’m done. Time for sleep.

*sigh*

I’m not going to get away with that, am I?

Honestly, I’m just… still kind of in shock. I’m letting everything sink in. Today was...

Well, I’ll start with last night.

After I dozed off, I had an incredibly vivid dream. I was back in the stable, in one of the upstairs bedrooms. The red drapes on the windows, the faux-gold bedframes, it was just like it always was. The air was thick with sex and perfumes. Candles adorned every corner of the room, illuminating it with an orange glow. It so was warm. It was always warm in the stable, there was a hearth in every room and a dozen fires kept this building glowing with heat even in the dead of winter.

I was in ecstasy. Derpy was on top of me, riding me with passionate vigor. Her mane was ragged from our combined fervor and, for some reason, her eyes weren’t crooked. Her gaze bore into mine. I couldn’t stop staring into those sunset colored eyes. Entranced, I reached up,wrapped my hooves around her, and pulled her soft body into mine. She was so hot and sweaty and hungry. Her hips continued to gyrate tirelessly, engulfing my member. As our bodies thrashed in satisfaction, she leaned in…

… and she kissed me…

...on the lips.

Our tongues wrestled and our lips clashed in soft, wet passion. She tasted so salty.

It lasted… seemingly hours.

It was… nice… incredibly, amazingly, impossibly nice.

My climax was… peerless. Emptying my testes into her filled every inch of my body with pleasure. When my climax began to fade, so did the dream. I never got to see Derpy come.

Not that I haven’t seen that plenty of times.

When I woke up it was almost noon, and my sheets were absolutely coated in spunk. The remains of my fantastic (literally) orgasm. It made me feel… kind of childish, honestly, and maybe a little ashamed. I hadn’t done that in my sleep for years, not since before I was an escort. That said, waking up with a crusty coat and dirty sheets isn’t the worst thing in the world. It’s easy enough to fix: laundry and a shower. They solve so many of life’s problems.

Anyways, it was a pretty empty day until the date. I spent the better part of my morning deciding on an outfit. I briefly considered going in a dress shirt before coming to my senses and realizing how absolutely ridiculous of an idea that was. A dress shirt and jeans is just… awful. So I went with a polo shirt. I’ve got a pink one. It goes well with my mane, I feel. Jeans, as usual. I really wouldn’t feel right leaving home without them. And a nice warm overcoat. Not remotely fancy, but wonderously warm. I figured I could get away with it, since we’d almost certainly be eating inside. If there were any outdoor events, I would go with a dress coat, but I knew I’d be able to take it off once the date got going.

Having decided my outfit a full six hours in advance, I was left with little to do other than dither. My magazines were all read, my house was pristine, and my walk was appropriately shoveled. There was nothing for me to do… until the mail came.

There was a loud knock at the door. “Guilty! You have so many magazines!” shouted Derpy from beyond the confines of my home.

‘Derpy’s here. Derpy’s here now. I’m not mentally prepared for this. I forgot she delivers my mail now. Oh, my gosh. Why didn’t I plan for this?’ I didn’t lose my beat, like the day before. I answered the door properly. ‘Be calm, be natural, smile.’ “Hey, Derpy.”

There she was. The same mare I’d been literally dreaming about. “How do you read all these?” she asked as she hoofed me a sizable stack of print and paper.

I almost lost my balance as she hoofed me my subscriptions to Equestria Outside and Fashion Now and Cosmarepolitan and everything I read for the sake of clients. (Well, not EO, that one’s for me.) “*Unf* I don’t. I just read the ones I need to.” I placed my magazines on the table. I would deal with them later. “So, this is your new route?”

“Uh-huh! You’re my last stop, too.” She was panting. She must’ve been flying around for hours with my fat stack of mail. Part of me wanted to apologize. I mean, it was sort of my fault. But, I mean that’s her job, right? She glanced at the pile I’d placed on the table. “So how do you know which ones you have to read?” she inquired.

“It depends on the client. Some clients like to talk and I need to know a lot about what they like.”

She nodded. “That makes sense. Well, I’m gonna get going. See you tonight, Guilty!” Off she flew.

“Y-yeah! See you!” I called after her. The encounter was sort of surreal. I’d been preparing to see her on a date all day long, and when she shows up it’s unannounced and totally casual. Not only that but it lasted all of thirty seconds. If it weren’t for the sudden appearance of my monthly delivery, I would’ve almost believed that she’d never stopped by at all. It was as though she were only a dream.

No, the humor of that statement is not lost on me.

The anticipation was excruciating. I waited for hours with nothing to do. I mean, I have a lot of days like that. But when I know there’s something that I have to go and do later, it just makes the idle time so much more… idle.

Okay, that sounded kind of dumb, but my point is in there somewhere.

I tried to flip through some of the magazines, but my head wasn’t doing its job. Eventually, I just gave up.

The hours passed and passed, until finally it was time to go.

So, ready or not, I made my way to Derpy’s place. The majority of the trip was easy; there was snow on the ground but the sun was out, and it wasn’t too chilly. The last few steps though… they were kinda hard. When I got to Derpy’s home the sun had just set. There was smoke billowing out of the chimney, firelight in the windows. It was a happy, warm, little cottage.

‘Okay, Guilty, relax. It’s just a date. Not even a real date, it’s just practice. You’re good at dates. You’ve been on plenty of dates, and most of those were fake, too. Besides, all you’re trying to do is help Derpy. You like helping Derpy. Just relax, let it happen, and enjoy it.’

“Fuck it,” I whispered to myself, opening the front gate and rushing to the door. I swallowed all my anxiety. I reached out and knocked before I lost my spine. It opened with a creak, putting face-to-face with… no one?

I looked down. ‘A tiny unicorn…’ I’d been so concerned with what I was going to say to Derpy, I hadn’t considered the possibility of someone else answering. I blinked as realization dawned on me. ‘Holy balls, this must be Dinky!’ She was a darling little thing, the spitting image of her mother, messy blond mane and all. ‘Say something, Guilty. It’s first impression time.’ “Hi, there.” Gentle smile. Eye contact. “You must be Dinky.”

Her reaction wasn’t what I was expecting, but wasn’t to be unexpected. (That made sense, shut up.) She frowned and rolled her eyes at me. “Mooooom!” she called in a half-annoyed tone before retreating inside. It made sense; I’m sure she’s had to meet plenty of the stallions that Derpy’s tried to date. Anypony could get fed up with that. As she retreated into her home, she left the door open, which I took as an invitation to, at the very least, shelter myself from the cold.

“Hang on, I’m getting dressed!” came a familiar voice from beyond a closed door. Derpy’s home was pretty much the same as the last time I’d seen it. It was cluttered, cramped and a tad messy, but still very warm and cozy. Dinky was lying on the floor, making a crayon drawing that would no doubt wind up pinned on the refrigerator.

Terror began to dawn on me, as the nature of my situation became clear. ‘Okay, Guilty, don’t freak out, but you’re all alone with Dinky for an unknown amount of time. You can risk saying nothing and hope that Derpy comes downstairs before things get unbearably awkward, or you can attempt to hold a conversation with a child until her mother comes downstairs. You don’t have the greatest track record with kids, but at the same time, the stakes are pretty high. If you don’t get Dinky to like you, things are going to be rough.’

I decided not to be a total pussy about my situation and attempted casual conversation with a grade-schooler.

The most dangerous game!

“So… what’s that you’re drawing?” Nice and simple. A very safe play.

“Tank,” she responded, still slightly annoyed.

I wasn’t going to be rude, but her drawing didn’t really look at all like a tank. It was more like a helicopter, to be honest. “Well… alright then.” ‘Nice job. You got one word out of her. Try something a little more engaging.’ “So, um… how are you?” ‘Really? That’s engaging?’

“Fine,” she said as she grabbed a green crayon. Well, at least the color was right. ‘Well, we’re up to two words now. Another five minutes and you might have yourself a sentence.’

I rubbed my temple. Fucking kids. “So, you like art?” I asked, determined to get more than a single word in response.

“I guess.” Two words at once! Victory! Conversation achieved… sort of.

“I never liked art,” I admitted. “Never had a knack for it.”

She just hummed in response. My head fell. I am so bad with kids. It’s pathetic.

A savior came in the form of a bundled-up Derpy. “Hi, Guilty! Sorry I took so long.” She looked adorable. I was half-expecting makeup and a dress, but a giant puffy coat was fine too. “You ready?”

I smiled. Not a calculated polite smile, not an artificial hunky smile, not a practiced seductive smile, just a smile. All that dread that I’d had, all that fear and anxiety of how much it was going to hurt being on a fake date was just... gone. Out of mind. I was just excited.

“I’m ready when you are,” I responded a tad energetically.

She smiled back. “Alright!” She turned to her daughter. “I shouldn’t be gone too long. Dinner’s in the fridge.” She gave her a big noisy kiss on the head. “Say goodbye, Dinky.”

“Byyyye,” she droned, solely out of obligation.

Derpy looked up at me with eyes full of anticipation and a smile that was ready for anything. “Let’s go.”

We took our leave. Thankfully, it wasn’t snowing that night. The air was cold, but not in a “chill you to your bones” sort of way. The two of us walked side by side down the dark streets of Ponyville under an ever-dimming sky. “It’s not too bad out tonight,” I commented. Conversation rule number one: you can always talk about the weather.

“Yeah, it could be a lot worse,” she responded with a nod. “So how’ve you been, Guilty?”

I chuckled. “You saw me just yesterday, Derpy, and this morning. Not a whole lot has happened.”

“Yeah, well, I gotta brush up on my date questions. Just pretend you’ve got something to say,” she said, sticking out her tongue a bit.

“But what if he really doesn’t have anything to say?” I teased.

“Well… uh… I hadn’t planned that far ahead.” Her head sank. “Ugh… I’m so bad at this.” So hard on herself.

I felt kind of bad. Here I was, already enjoying myself, and Derpy was a ball of stress. This was the exact opposite of how I pictured this going. “Hey, relax. Just focus on having fun. Don’t sweat the small stuff.”

“Easy for you to say,” she whined. “I’m trying to get better at this. Go easy on me.”

“Alright, alright. Start over.”

“Okay… *ahem*… So how are you, Guilty?”

“I’m okay, Derpy. Business is okay. What about you?”

“I’m doing good. Mister Crate hasn’t yelled at me in a while.”

I scoffed. “Wow, that’s a downer.”

“Huh?” She looked up at me, perplexed.

“When you say it like that, you make it sound like he yells at you a lot,” I explained.

“But, he does.”

“And that’s a downer,” I pointed out.

Derpy brought a hoof to her chin and hummed. “I guess so. Thanks, Guilty.”

“Any time.” I took a moment to examine our surroundings. It occurred to me I didn’t know where Derpy was taking me. “So, where are we headed?” I asked.

“Huh?” Her eyes bulged slightly. “But, I was following you!”

I blinked. “Whoa whoa whoa, you asked me out. You gotta have a date prepared,” I teased her once more.

“Oh… uh… okay… um…” Her gaze shot around for a moment as she searched the streets for a proper venue. “Okay… I know a restaurant. It’s, um…” she spun around once before determining a direction. “… this way.”

I chuckled. “My gosh, you are too cute,” I said, entranced by her adorable little confused twirl.

She blushed. “W-why are you saying that?” She hid her reddening cheeks behind a foreleg.

To be clear, those were the cheeks on her face…
.

… Okay no more sex humor, I’m getting bored of it.

I giggled. “I’m complimenting my date. You did something cute, and I commented.”

“But… I didn’t… I’m not cute!” she insisted with a stamp.

“Yes, you are.” My words were equal parts sincerity and whimsy. “Learn to take a compliment. Dates tend to try and flatter you.”

Her face scrunched angrily, but she nodded.

I continued to follow her down Ponyville’s streets until we reached a small restaurant. It was a cute little place; a few snow-covered tables sat outside, but the inside was pretty packed.

I love the din of a full restaurant. Clacking silverware, low conversations, it all forms a very comforting background. When we stepped inside, the air was warm and inviting. It was no wonder it was so crowded; it was the perfect respite from the weather outside. “Table for two,” said Derpy to the hostess.

We were crammed into a little couple’s booth. I tried not to focus on everypony else as I read the menu, but it wasn’t exactly easy. More than a few townsfolk couldn’t help but gape at the whore out in public… with a mare… on a date.

“That poor dear,” somepony whispered. “Is she paying for this?” another voice inquired.

Ugh… gossip gossip gossip. Derpy didn’t seem to notice; the menu had her full attention. I felt so bad. Even if Derpy was determined not to let it get to her, this date was affecting her public image. ‘Just leave, Guilty. Excuse yourself. You’re making her look bad. Just see her in private, at your place or together with her friends. This is too open. Too exposed.’

“Whatcha gonna get, Guilty?” I hadn’t actually taken a look at the menu; I’d just been using it to shield myself from the judging gaze of others.

“Uh…” There was a decent selection. Sandwiches, pastas, soups salads, all the staples were there. “That second spaghetti dish looks pretty good.”

Derpy glanced back at her menu. “Bleh… eggplant. I’ll pass. I think I’m just gonna get some soup. The tomato soup’s really good here.”

“Yeah, it’s soup weather, all right.” I folded up my menu and put it down. I needed to come up with some “date things” to say to Derpy if I was going to help her out. “So, what do you do?” I asked her.

“Huh? I’m a mailmare, you know that,” she said, slightly confused.

“Practice, Derpy. It’s for practice.”

“Oh, right… um… ask me again.”

I nodded. “So, what do you do, Derpy?”

“I’m a mailmare here in town. What about you?” Not at all bad. A fairly natural delivery. She’s not as rusty as she thinks.

“I repair watches. I have a little shop in town,” I lied.

“Buh?” Flabbergasted.

“You never know what your date will say. You have to be ready for anything.” I stuck a tongue out at her.

Derpy’s eye’s narrowed. “You’re having fun with this aren’t you?”

I smirked. “Maybe a little.”

Her stern gaze vanished as she giggled at my playfulness. “You’re so silly, Guilty.”

When the waitress came to the table, she did her best not to stare. She wasn’t a client, but she knew who I was. “M-may I take your order?” She tried her damnedest to be polite, and she succeeded for the most part. She failed to make eye-contact, but hey, no big.

“I’ll have the House Pomodoro and a glass of red. Derpy?”

“Can I get a bowl of tomato soup?” she asked eagerly.

“Of course.” She swallowed nervously. “Anything to drink?”

“Oh, just water,” she responded.

“Great.” She turned to leave before doubling back. “Oh! Let me just get those, uh… those menus for you.”

I almost shook my head as I hoofed them to her. ‘Don’t stress yourself, we’re barely paying attention to you.’

“So, what’s it like being a watch-repair pony?” Derpy asked with a roll of her eyes. I guess she decided to play along.

“Well, it’s kind of nice. I make my own hours, work from home. There’s not a lot of time outdoors, though. I spend a lot of time at home… alone.” Exaggerated sigh.

“Now who’s being a downer?” she accused. “Lemme guess… ‘you never know when your date is going to be a downer?’”

“Something along those lines,” I admitted with a giggle. “That, and it’s fun to role-play.”

“I guess.”

“So what about being a mailmare? That’s got to be tough.”

She shrugged. “It’s not so tough. Mostly it’s fun, ‘cause I get to say hi to everypony all day long.” Her features all lit up. She really does love her work.

“You’re just too darling, aren’t you?”

She blushed again. “Stop complimenting me, it’s embarrassing.” Protest as she might, she still smiled at my flattery.

“Get used to it. It’s not gonna end any time soon.” I cradled my chin on my hooves. I was taking such delight in my own impishness.

She groaned in response. “You just like watching me suffer, don’t you?”

“I’m not going to lie, it’s actually kind of fun. You look so cute when you’re embarrassed.”

“Oh… cram it.” She laughed despite herself. “It’s actually kind of nice… I don’t get that a whole lot.”

“Downer,” I chided.

She just glared at me. “Anyways, thanks again for this, Guilty. Practice or no, it’s nice to get out of the house.”

“Agreed. It’s been a while since I had dinner at a proper restaurant.” I pondered briefly. “Actually, I didn’t know Ponyville had any proper restaurants.”

Derpy emitted a charming giggle. “Only a couple. They’re just some family run places. The food’s super good, though. I bring Dinky here all the time.”

“Who’s Dinky?” I asked pointedly.

“Ah.” Derpy caught on to my meaning. At some point in her date she is going to have to explain that she’s a single mother. “But I mean, everypony in town knows about me anyways, it’s not like I’m going to have to tell them.”

“That’s true. I forget how small towns work, sometimes. Everypony knows everypony.”

“Yeah, well...” Derpy just shrugged. “... it’s not all good.”

I chuckled. “I never said that that was good, Derpy.”

She waved a hoof at me. “Oh you… but I’m serious, everypony knows all about… well everything.” Her meaning was clear.

“I don’t.” I spoke before I realized what I was saying. I’d caught bits and pieces about it from Derpy, but she never really talked about him. I caught myself. “I’m sorry, I didn’t mean to—”

Derpy shook her head. “It’s fine. I mean, it’s kind of…”

“A downer?”

She nodded. “But, it’s not like it’s a secret or anything. Everypony knows.”

“I’m sure, but that’s not why we’re here. You don’t have to—”

“I don’t mind,” she interjected. “Really, I don’t. If you’re curious…”

“Well…” I mean… it’s something that would’ve come up eventually, right? She already tells me just about everything. And if everypony already knows, there’s nothing weird about talking about it public, I guess. “... sure. Tell me about him.” I’d always wondered, honestly, about Dinky’s father. I’d just thought it wasn’t appropriate conversation for, well, Derpy’s and my relationship. But if she was offering, so… why not?

“Well,” she began. “His name was Dusty. He was from Canterlot, and he was an archaeologist for the Royal Historical Society. He came to Ponyville to study the old castle in the Everfree Forest.”

I didn’t know there was a castle in that forest, but I wasn’t really paying attention to that at the time. I am curious about that though. I’ll have to ask somepony about that at some point.

“I was just out of school, and had started working as a mailmare. I was making a delivery to the hotel he was staying at and we met in the lobby, and… four months later we were married. Ten months after that, Dinky came along.”

‘Only ten?’ I would’ve joked about a shotgun wedding if I could’ve brought myself to speak. I was just in awe, this story it was just so… real. I’ve said before, I primarily deal in the artificial, so when a story this… true was being told to me, I couldn’t do anything but absorb it.

“For a while I was a stay-at-home mom. I lived with my parents and raised my little girl. Dusty would disappear for weeks to go investigate some new ruin or another. He always came back, though… until he didn’t. This was years later, I’d moved out of my Parent’s place and they’d moved down South and we had a nice little house that we lived in. I got a knock at my door and some very bad news. There… there had been a cave-in, and Dusty…” she swallowed hard. “... didn’t make it.” She fought back her tears with ease, but there were certainly tears to be fought. “Sorry, I *sniff* told you it was a downer.” She looked up at me and her face became one of concern. “Oh, don’t cry, Guilty.”

‘Am I crying?’ I reach a hoof to my face in shock, and sure enough it was moist. I’ve heard plenty of sob stories in my day, but I’d never really been moved to tears. This, though… apparently it was too much. “I-I’m not…” I wiped furiously. “Okay, yes I am.” Ponies were staring. I was emoting. I needed to leave.

“I’m sorry, Guilty. I wasn’t trying to…” Her head fell once more. “I’m a terrible date,” she lamented.

“N-no, Derpy. It’s fine, it was just…” ‘Get out. Collect yourself.’ “...a lot to take in.” I grabbed a napkin and wiped away my tears. “I’m just going to use the bathroom.” I swiftly retreated, doing my best to hide my face from the eyes of the townsponies.

I needed a mirror. I had to assess the damage. I found the bathroom and, with a nervous spring in my step, trotted to the mirror.

‘Yup! That’s the face of a grown-ass stallion crying, alright.’ I took deep breaths. ‘I just need a moment. I need to breath. In. Out. In. Out.’ Even steady breaths didn’t come as easy as I would’ve liked. My lungs wavered as tears were denied existence. I tried not to think about Derpy. I didn’t want to think about that… that sadness she must carry with her every day. I’d seen her a bawling mess of tears, but this was a heavier sadness, and engulfing sadness. I hoped… I prayed, that I’d never have to see what her face looked like when she got that news. I hoped she’d never have to wear an expression like that again. I just… couldn’t comprehend a Derpy that was that sad.

Smiling is her special talent. A face like that wouldn’t suit her.

Fuck, I’m crying again.

So, I proceeded to clean myself up. I’d managed to swallow most of my tears, but my eyes still showed a the telltale signs of crying. I silently cursed myself for not bringing any makeup. When I returned from the bathroom, our food had arrived. Derpy was already happily slurping away at her soup.

‘Well, time to be charming again.’ “Sorry about that.” ‘That was charming?’

Derpy put down her spoon and twiddled her hooves. “No, I’m sorry. I didn’t mean to make you cry.”

“You didn’t, you just…” ‘Change the subject.’ “...started eating without me.” I managed to smirk, as I forced myself to be playful. “How rude.” I stuck my tongue out a tiny bit.

Derpy’s brow furrowed. “Oh, right.” She shrugged and continued to… eat… drink… whichever… her soup. “That one’s not so bad, right?”

“Indeed it’s not.” I took my seat and sized up the meal before me. It was a positively massive portion, easily two meals. I would be taking some home for certain. It was a nice looking dish, too. The veggies and the pasta and the sauce, it all looked simply scrumptious. I took a bite. It was good, very good. With all of Ponyville’s quality ingredients it’s to be expected, but still, I was impressed.

The wine was okay, less than stellar.

Soon my tears were forgotten and our date continued. As we ate I continued to tease and flatter Derpy in equal measure. Whether or not she would admit, I think she enjoyed both. The meal carried on splendidly. We ate, we laughed, I ended up drinking a couple glasses of wine. It was…

Heaven…

…and then it ended.

When the check came and I could feel the evening coming to a close, the high began to wear off. I was becoming painfully aware that this was all just… pretend… again. After our meals were gone, and the check came… I suddenly found myself not enjoying the evening.

I paid, of course, and we took our leave. As I escorted Derpy back home, snowflakes began to fall ever so gently onto Ponyville’s streets and rooftops. Derpy must’ve thanked me a dozen times on the way back. She said that she had fun, and felt much less worried about going on proper dates again.

I just smiled as best I could, and assured her I was happy to help.

When we got back to her place, I could feel… I could feel my heart breaking. Another session was coming to an end, and I didn’t want it to. The little fantasy Derpy and I had indulged in was coming to a close, and it was time for us to return to our respective realities. The fun was... expended… used up… consumed, and Derpy had gotten everything out of me that she needed, as she always does.

Downer.

“Well, thanks again, Guilty. I really appreciate it.”

‘Be strong.’ “Yeah, it was no trouble. I had a blast.”

“Me too. See you Sunday?”

‘Be Strong.’ “Of course”

She nodded. “Mmkay!” We arrived at her front gate. “Here we are!” she announced proudly.

‘Be strong. It’s almost over. You can go home and have yourself a good cry.’ “That’s right… well, uh… I’m looking forward to your next visit.” It was truer than she knew.

She smiled warmly. “Okay. Good night, Guilty.”

“Right…”

I was about to say goodnight. I was about to march home with my head hung low, crawl into my shower, and weep until passed out. I was about to go throw my own private pity party as the pain of unrequited love coursed through me; It’s a pain I’m not a stranger to. I was about to go and let my metaphorical dam burst. I was about to let my feelings continue on, unrequited, as Derpy went out to date stallions and have a whole life of her own. I was about to do a hundred hundred cowardly, lonely, safe things all alone in my big, chilly cabin on the edge of the woods.

But then I did something fucking crazy.

‘Ah, fuck it!’ some voice within me chimed.

I swallowed hard. “So, Derpy, do you want to do this again sometime?”

I could’ve sworn my heart had stopped. ‘Did I just say that? I just said that. Am I doing this? I’m doing this.’

Derpy seemed rather confused. “Why? Think I need more practice?”

I shook my head. The rest of me was shaking as well, and it had nothing to do with the cold. My hooves trembled, my chest literally shuddered, my mouth was dry and my tongue was paper. “No, I… I mean…”

‘Make something up, you’re not committed yet.’

“…I mean…”

‘You don’t have the guts!’

“I mean for real.”

That had just happened. That had actually just happened! I had gone balls deep on the first thrust. I had gone from accepting that a love could never be to pursuing it!

I honestly cannot say… why I did that. It was just so very… not me. It wasn’t self preservation, it wasn’t the path of least resistance, it wasn’t… Guilty.

Which I guess means that Sour Dough was the one that spoke up.

Maybe I’ve got balls I don’t know about out.

Regardless, at that moment I wasn’t pondering any of this. All I was doing was waiting for response. I’m not sure how long I was actually waiting, but it felt like minutes. Derpy’s face was stone still in a bewildered visage. When she finally spoke her voice was quiet. “Are… are you serious?”

‘Say no. You weren’t serious, you were just messing around. You can still get out of this.’ “Y-yeah.” My voice was wavering. “W-why not?”

Something new began to creep into her expression. Her lips curled and her brow furrowed. I did not like what I was seeing; a slow burning anger was building up in her. ‘Well, you’ve done it now.’ I was ready for her to shout at me. To scream and rant about… something. I’m not sure. I closed my eyes and waited for some inevitable tirade.

Instead she just punched me in the chest.

“Oof!” I reeled back from the blow. It hurt, but was by no means meant to harm me for real.

As I regained my composure, I found an accusing hoof thrust at my face. “You lied to me!”

“I…” I let her statement knock around my head as I tried to make sense of it. When my brain came back with nothing, I responded rather dumbly. “Huh?”

“You said…” She tapped me in the chest again. “… that escorts. Can’t. Date. Clients.” Each word was punctuated with another angry jab.

“Ow!” I rubbed what would surely be a bruise later. “I… I did? When?”

“Forever ago! You said it was a rule or something!” She was almost screaming at this point. I didn’t remember ever telling Derpy that, but apparently it had come up.

“W-well it is.” I could feel my heart beating in my chest. I mean really feel it. ‘I-I just—”

“That’s the only reason I didn’t ask you out, like, a year and a half ago!”

I took a moment for her words so sink in. “Hang on. What?”

Derpy shrugged angrily, if that’s possible. “I mean…” She stared at the ground, looking for her next words. “...I was kind of asking out everypony at the time. I would’ve asked you too if you hadn’t said that!” Jab.

“Ow!” I rubbed my chest. “You keep hitting me in the same spot.” Definitely gonna be a bruise. “And… um… okay, I’m not sure where that puts us.”

“Neither do I!” I’d failed to notice that Derpy appeared just as embarrassed as she was angry. Her anger, however, began to subside as she physically relaxed. A blushed filled her face as she realized how heated she’d gotten.

“Um… w-would… would it be okay?” Her voice was almost a whisper again.

“Y-yeah,” I replied weakly. My face felt hot. I’m sure the two of us must’ve been quite the sight. Just a couple of ponies, standing out in the snow, blushing up to our ears. Neither of us were making eye contact or speaking anymore I don’t think I’ve known a more awkward moment. So, we stood, neither of us knowing what to say.

I said something anyways. “I… I think I really like you.”

“O-okay.”

Silence again.

Everything was sort of up in the air. On the one hoof she seemed at least okay with the idea, but on the other hoof she wasn’t saying anything. ‘This is weird. This is so weird. What am I supposed to do?’

“I’ve made this very awkward, haven’t I?”

“Heh, maybe a little.” Our eyes met. “Actually, now that the shock’s wearing off, I feel a little better.”

“Well, that’s good. Um… so… do you wanna…” I swallowed. “...do this?” I asked, trying not to sound desperate.

“Well, yeah.” She chuckled nervously. “I mean, it’s worth a shot, right?” She smiled, before clearing her throat. “Sorry I punched you.”

“It’s okay. I was just worried that I’d made you upset,” I admitted.

“No, you… well… yeah, a little.” She giggled. Apparently she was giggling again. “More than anything I just wasn’t expecting it.”

“Sorry, it was... kind of a surprise to me, too.” My frantic heart rate was dropping, I’d stopped sweating, my breathing returned to normal. All the adrenaline was wearing off. “I can’t believe I actually said something.”

“You can’t believe it?! I thought that this could never happen!”

“Well, me too, a little.” We both giggled at that.

“So, um… you wanna talk about this tomorrow?”

“What’s to talk about?” she asked innocently.

I had a thousand responses. There were details to attend, wrinkles that needed ironing out. What gets told to Dinky and who tells her? How often do we go on dates right now? Do we even go on dates, is that a thing? I mean we’re dating now, right? Or trying to? Or starting to? Or… something? Do I keep charging you for sex? Do we still even have sex? Can we go hiking more? Can hiking be a date? I’d like hiking to be a date occasionally. Where is all of this going? What’s our endgame plan? Marriage? Children? There was so so much to talk about.

“Nothing, I guess. So um… just until Sunday?”

“Yeah sure, unless you get a letter.”

“O-okay, yeah… um… you could just stop by whenever, if you like. If I’m not with a client, you can come in. I can cook you something, or something.” I must’ve sounded so desperate, but Derpy smiled regardless.

“If I’ve got time.” She smiled.

“Okay.” She seemed… eager? ‘That’s good, right?’

“Um… Guilty?”

“Hmm?”

She shifted uncomfortably. “Do you wanna…? Can I…?” She took a breath. “Can we kiss?”

‘Oh…’ “Oh…”

“I mean… if not that’s fine, it’s just… never mind, it’s not—”

“Nonono, it’s… fine.” ‘Is it?’

“You don’t seem so sure.” She put a hoof on my shoulder. “Don’t push yourself, Guilty.”

“It’s not… no it’s fine, it’s just... um… I never… I’m not very—”

“It’s fine, Guilty, really. Don’t worry about it.”

“N-no, let’s do it. I’m just… not very good at it.” And there was all that nervousness again.

“If you’re sure.”

“I am.” I actually think I was.

So we… kissed… for about a minute. It wasn’t… quite what I was expecting. The kiss in my dream was just… perfect, a fusion of flesh and fluids. The reality, though? Our teeth kept knocking together. My tongue was kind of all over the place. I bit her a little bit too hard at one point. At the end of it, we were both feeling sufficiently awkward again. Derpy was the first to speak this time. “Guilty?”

“Yeah?”

“You’re a really bad kisser,” she said with a laugh.

“Sorry.” My head sank.

“It’s okay. It’s kinda cute actually,” she teased.

‘Cute?’ “I-I’m not cute,” I stammered.

She stuck her tongue out at me. “Now you know how I feel.” She opened her front gate and began to walk away. “Goodnight, Guilty.”

‘She’s leaving?’ “G-goodnight.” I watched her as she walked back into her home. Her hips seemed to sway a little more than usual as she strode. When she got to her door she turned, she waved, and she disappeared inside.

And I sprinted home.

I had to write right away. I couldn’t believe it. I couldn’t believe it! Nothing was a hundred percent certain yet, but we were going to give it a shot.

A shot, I have a shot!

I still can’t wipe the smile off my face.

And on that note, I’m going to go to sleep. I don’t think I can feel any better than I do right now, and I want to try and carry that into tomorrow.

Author's Notes:

So here's a chapter that I'm sure half of you have been waiting for since Chapter 3.

Once again, like, comment, follow, fave, all that jazz. It fuels my glorious golden ego!

Thanks to all my editors: BlackSkulls, aquapunkchick, coandco, and Jake The Army Guy.

Now listen here guys. Go ahead and check my blog for the potential to have your own OC appear in my story! I've done it once before and I've been considering doing it again. Check the link below for details!

http://www.fimfiction.net/blog/274985/new-chapter-and-news