Dear Journal,

Well Crook stayed with me for a few days. His visit was... enlightening. There’s... a lot going on in my head right now. It’s sort of hard to try and deal with everything at once. There’s just so much to get down on paper. It’s taking a good amount of self-control not to start frantically scribbling everything.

I think the best thing to do would be to just start where I left off...

The exhaustion of Lyra and Bon Bon’s session had set in (a fact I believe I sufficiently hammered home), but the moment I realized who was knocking on my door I was adrenaline kicked in, and I was on full alert. I slammed my journal shut and practically sprinted to my front door. I almost tripped over myself running down the stairs.

As I approached he knocked again. It was his knock. The knock he always used. The knock that let me know it was him on the other side. Two soft knocks, and then two hard knocks. When I was a kid that sound got me more excited than anything.

I threw the door open, and there he was. I barely noticed the blast of air that accompanied him. His mane was iced over from the blizzard. His teeth were chattering. His knees were knocking together. I could see his breath.

“Fuckin’ let me in!” he insisted, glaring at me.

I had just been staring at him. I was just… blown away. I was awestruck; my mouth was agape. I mean… Crook was here. Crook was here.

I hastily ushered him in, my mind abuzz with questions. How are things? How’s the stable? Did you get my letter? Are you still seeing that accountant? How were the last two years or your life? In my haste I just sort of blurted the first thing that come to my mind.

“What the fuck are you doing here?!”

Classy, Guilty. Real Classy.

Crook quickly made his way over to the embers of the once blazing fire across the room. “Fuck... throw on another log, Guilty. I can’t feel my hooves.” He said, ignoring my question entirely.

“Crook.” I deadpanned.

“Shit, Guilty, I’m freezing my ass off over here.” He shivered as he hurried out of his frosted-over sweater. “Does this town not have a fuckin’ weather team, or what?”

“Yeah, just... I dunno... it’s a fucking mess right now apparently.” I sighed heavily. As eager as I was to get some answers out of him, I knew arguing with Crook was a waste of time. He’ll argue just to argue. “… do you want a cup of tea or something, then?”

“Whiskey would be great.” He suggested as he lay down by the fire.

“I’m…" I let out a long sigh and walked to the kitchen. "I’m gonna bring you some tea.”

“With whiskey in it?” He asked.

I ran a hoof down my face. The adrenaline shock of his presence was wearing off, and I was suddenly feeling very tired again. “Fine. Sure.” I grunted back to him.

Now, normally I’d be pissed if somepony showed up at my front door in the middle of the night, unannounced and immediately started asking for booze. But… it was Crook. Crook and I grew up together. We lived in the same neighborhood.

Back then, I used to… I used to live with my father... in the apartment above his bakery. I spent a lot of time in that bakery. Sweeping or putting things on display or whatever my father barked at me to do.

I still remember the first time I saw Crook. I was sweeping the dead leaves away from the entrance and he was sitting against the bakery window, looking hungrily at the various breads on display. I noticed him staring longingly at this big loaf of cornbread that had just come out of the oven.

I was young... and stupid. I was a little colt, and he was a big kid. I wanted to be his friend. So... I snuck a piece of it out to him. My father caught me, of course, and… whooped me good. Crook ran away, though. The moment my old man came out the front door he was practically down the street already, eating his cornbread as he ran. I remember thinking… ‘He’s so fast!’ Even as my father pulled me inside. I couldn’t help but watch him run. The next time I saw Crook was about 2 years after I started going to school.

School was… real real tough. I think I’ve explained before that I was a lanky kid. Well, that made me an easy target for ridicule. I got picked on, I got bullied, I got pushed around, and I got beat up. A lot. One day, though, while I was getting kicked around on the bathroom floor, Crook showed up. I don’t really remember what happened, I just remember him. His Ivory coat… his crow black mane… but I remember his glare most of all. I remember all the anger and fury in those dark brown eyes. The next thing I remember I was waking up in the nurse’s office. When I asked how I got there, the school nurse said that an older kid had brought me in, but she didn’t know his name.

I looked for him for a while. Tried to find him base on what little I knew. Who was this kid who saved me? I looked everywhere I could think for him. I searched every classroom, every table at lunch. He was never anywhere I checked.

Well, as it turned out he never really showed up at school. He only came in once a month or so, when the school made him. It had something to do with school funding, I don’t remember exactly how it worked.

When I did find him, he was fucking around the dumpster behind the bakery. I was throwing away some day-olds, and he breaking bottles in the alley for kicks.

The first thing I said to him was “thank you”. Ever since that day, the bullies had let up a little bit.

I still remember what he said in response. “You don’t have to thank me. I was thanking you.”

And with that I had realized who he was. He was that kid. That hungry kid that ran so fast.

Then, he asked what was wrong with the bread I was throwing out. Nothing was wrong with it, I said. It was just old. He asked if he could have it. I handed him the bag, and... we were friends.

After that, Crook started going to school, and I got picked on a lot less. Whenever some dumbass thug kid tried to shake me down for money or food or whatever, Crook was always just minutes away with a can of whoop-ass. He was like my bodyguard and my best pal all rolled into one. He didn’t always save me, mind you. I still got my shit kicked in quite a few times, but he would still always make sure I got to the nurses office.

The two of us were honestly just a couple of delinquents. When school was out we’d pull all kinds of stupid shit. We’d shoplift, we’d tag shit, we’d break windows. We were dumb-ass little kids. We barely ever got caught, though. Crook was so fast, and I was so good at lying and playing innocent that the two of us almost always got away scot-free.

One day in middle school our lives changed for the better. Crook said he’d found a way for us to make some money. That day he led me to the stable, and we both got jobs as errand boys. After that I was barely ever at the bakery. It was wonderful. During the day Crook and I would go to school or fuck around, but come sunset, the two of us were running potions and lotions and condoms and booze wherever they needed to be. We’d go home late… sleep and the cycle would begin again.

Those days… they were heaven. We could buy ourselves good food. We could sneak bottles of liquor out the stable. We had plenty of time to brew mayhem all over the streets of Manehattan. When I was fifteen, I lost my virginity to a sexy young unicorn who’d just started as an escort. She said she needed to practice sleeping with stallions she’d never met, and I was happy to oblige.

Good fucking times.

When I was sixteen Crook became a fully-fledged escort at the stable, and he became one hell of an escort. He was… and still is… just a drop dead sexy stallion. He’s never had anything short of an athletic figure. He’s a pretty tall guy; he’s always been taller than me. He’s got a perfectly chiseled jawline. His mane practically styles itself. I’ve never seen him brush it, but it always looks amazing. And, of course, he’s got an absolutely massive cock.

Now, for the record, I only know that because the two of us used to double-team mares all the time. Crook was always a fan of the spit-roast.

Two years later, I turned eighteen, and followed Crook’s hoofsteps into the world of the oldest profession. We shared a room for six years.

So yeah, he’s easily the most important stallion in my life, and I owe him a lot. I can forgive a little rudeness.

I fixed him his tea (with a kick), and brought it out to him.

“Warm enough?” I inquired.

“Yeah.” I offered him his mug and he took it. “Thanks, pal.” He took a sip. And a satisfied smirk graced his lips. “Now that’s what I’m talking about.” He chuckled slightly. “Well don’t just stand there. Get warm with me!” He motioned for me to lay down by the fire next to him.

I obliged. I curled my legs up and lay beside him as he bathed in the warmth of the fire.

“So… Crook… why are you here?” I asked delicately.

He took a gulp of his little concoction and gave a satisfied little 'aah'. “Whaddaya mean, ‘why am I here?’ You wrote me a letter.” He responded. I waited for him to finish, but he was done. He was perfectly happy with his response.

“Uh-huh… and?” Was that really all the justification he needed? “I was just checkin’ in. I wasn’t tellin’ you to come all the fuckin’ way out here.”

Talking to Crook was making my accent act up.

Crook just looked confused. “You put your fuckin’ address on the thing.” He explained, apparently convinced that that clearly indicated an open invitation.

“So you could fuckin’ write me back y’idiot!” I punched him the shoulder.

Crook snorted in laughter. “Fuck that.” He took another long sip of his swill. This time he gave it a scrutinizing glance. “For fuck’s sake Guilty, too much whiskey.”

“Oh fuck right off, Crook. I’m afraid I’m not privy to the nuances of puttin’ whiskey in fuckin’ everything.” I was acting offended, but it was just that... an act. It’s just… how we are together.

“Fuck you, Guilty.” He snarked.

“Fuck you too, Crook.” I snarked right back. Our gazes met and we just grinned at each other. “I fuckin’ missed you, Straight Arrow.” I confessed.

“I missed you too, Sour Dough.” He wrapped an affectionate hoof around my neck and pulled me in close.

I hate my real name, Crook is the only pony who calls me that. Likewise, I’m the only pony who gets to call him Straight Arrow. To his clients, he’s just… Crook. It’s a nickname he got because of his cutie mark, a bow notched with a bent arrow. (Irony!)

He’s always thrived by following his own code. Doing what he believed in. By proxy, he excelled at breaking the rules of others. After all, that’s his special talent… staying off the straight and narrow path, and learning all the crooked ones.

In his early life, it was very literal. He knew every back alley, every broken fence, every shortcut, and every hiding place in Manehattan. If he really needed to, he could get away from anypony in that city, and more than a few times he did. Of course, it helps that he could run faster than most ponies.

Later on, Crook just excelled at making a less than honest bit. Stealing, working the occasional shady job, gambling, that sort of thing. I always told him if he put his mind to it, he could probably become a criminal mastermind. He’s just that good at being bad.

We had a moment there, lying by the fire in the middle of a blizzard. We hadn’t seen each other since I left Manehattan, but in some ways it was like we hadn’t missed a beat. It just felt so right to see him again. I leaned into his embrace. “So… I really gotta get some sleep, Crook. I got a client tomorrow morning.”

“What? We gotta catch up, Guilty. I got a hundred questions!” He jostled me in the hug, attempting to shake the exhaustion from me.

“Fuck, Crook. I do too.” I was about to collapse. “But… in the morning…” I leaned into him more. “I’m fuckin' bushed.”

He chuckled at me. “Fine.... ya baby.” He pushed me off of him rather suddenly. “Off we go.”

I pulled myself onto my hooves and led my friend to the bedroom. Once inside I lit a few candles, and Crook’s eyes went wide. “Fuck me… Is that...?” His jaw dangled freely as he gaped at my mattress.

“Yup… enchanted Cumulus… King-sized.” I tiredly explained.

He shook his head in disbelief. “If business out here is this good… I might just have to join you.” He was joking, of course. Crook lives and breathes Manehattan. He could never really leave.

“It’s not.” I said tersely.

“Then where did this beauty come from?” He inquired eagerly. As much as I really didn’t want to breach that subject, I was too tired to come up with a clever lie.

“Sunny.”

“Yeah? Well, she was fuckin’ loaded.” He didn’t pause for a moment. He knows most of what went down between Sunny and I, and how hard I took it. Some ponies might’ve frozen up at the mention of something like that, but not Crook. He just carried on like it was no big deal. He knew that that’s what I would have wanted.

Sometimes I think he knows me too well.

“Arright… I’m goin’ upstairs.” I yawned once more and made for the bedroom door.

“Whoa. Whoa. Where ya goin’?”

A memory rang through my head.

‘Crook can’t sleep alone.’

“I just need to grab a pillow.” I lied.

“There’s like, eight here. We got fuckin’ plenty.” He looked at me like I was crazy.

“I’m used to mine… can’t sleep without it.” I lied again.

“*Pffft* What a queer.” He teased.

“Yeah yeah, call your host a queer. That’ll end well.” I warned jokingly, and then left the bedroom.

As I treaded upstairs I scolded myself.

‘How do you forget something like this, Guilty? You don’t see him for two years, and suddenly you forget shit like this? Get it together.’

When Crook was a little kid, before I even met him, some... bad stuff happened to him. He told me what happened once… only once. He was drunk, and I don’t’ even know if he remembers telling me, but suffice it to say: Crook can’t sleep when he’s alone. Back when we shared a room, if I was ever busy and he was free, he would up wait up for me so we could sleep together.

Not like that.

Anyways, I fetched my pillow and returned to find Crook practically jumping on my bed. He was so… giddy. “Guilty… this thing is awesome.” Of all the things we escorts utilize, be it potions or oils or condoms, the thing that we tend to ‘geek out’ about the most is mattresses.

“Quit prancin’ around like a fairy… it’s fuckin’ lights out.” I began to blow out the candles. Each quick breath extinguished an orange light, and added an extra shade of black to the cozy room. Once the lights were all out, save the glow of the fire from under the door, I joined Crook on the bed, and the two of us tucked ourselves beneath the sheets. I unconsciously slid to the middle of the bed, placing my back firmly against his.

This is how we always slept. We used to share a bed quite often. Sometimes we were alone and sometimes we were accompanied by a mare (or several mares), but we always… had each other’s backs.

As I drifted off to sleep, I half expected my mind to drift once again to thoughts of stallions. Surprisingly, it never happened. For whatever reason, being around Crook didn’t bring up thoughts of my old gay sessions. If anything it kept me from thinking about it.

I can’t explain it.

I slept well… very well. Something about sleeping with Crook just feels… right. It feels like… home. I’ve lived in this cottage for two years now, but it never felt more like home than it did that night.

It makes sense, I suppose. The room we shared at the stable was the first real home I had.

I don’t… I don’t count the bakery.

Anyways, the next morning I was awakened a hoof poking at my shoulder.

“Hey Guilty… get up… I’m hungry… Guilty… hey… make me something.” Crook continued to poke and prod at me, attempting to rouse me.

“Mmmmwhat time izzit?” I mumbled, before bolting upright. “Oh fuck, what time is it?” My eyes quickly darted about for a clock. Eight a.m.. Still an hour to my appointment. “Oh, thank fuck. I did... *YAAWN*... I did not want to have to rush through this morning.” I sighed with relief.

“Fantastic, you’re awake… make me breakfast.” He insisted.

I was still getting my breath under control when I responded. “Just… have a bowl of cereal.”

“I would, but all you have is that kiddy sugar-shit. Make me a fuckin’ real breakfast.”

I crawled my way off of the bed. “Fine… grilled cheese okay?” I didn’t need to ask; it’s his favorite. I just wanted to see him excited.

And excited he was. “Fuck yeah! You got any tomaotes?” His face was stuck in a huge grin.

“Mmhmm. Good ones.” I began walking to the kitchen and crook joined me.

“Good because I want some right-“ Crook began.

I finished his sentence for him. “In the sandwich with a little bit of pepper, I remember.”

He chuckled and gave me a little punch on the shoulder. We do that to each other a lot, now that I think about it.

So I made him breakfast: grilled mozzarella and tomato on rye bread, with a glass of orange juice. I made myself the same.

Crook happily chewed away at his sandwich. “Mmh. Gvilty. Yoh fandwiches rre the bvest.” He garbled through his meal.

I swallowed a mouthful of cheesy goodness. “For fuck’s sake, Crook. Don’t talk with your mouth full.” I chastised. It was sort of a reflex. Crook used to come to me when he needed help with the non-sexual aspects of escorting; I’ve given him more than a few lessons in manners.

After that, the two of us spent a long while catching up. I told him about Ponyville. I told him about my friends, Derpy and Pinkie Pie. I told him about business, and how much I make. I told him about all the fun toys I’ve acquired since I got here.

He told me about the stable, and how everypony’s doing. He told me about some ridiculous new law about the size of soda restaurants can sell, that the mayor just issued. He told me (at great length) about how difficult his journey to my cottage was. In his defense he did sort of brave a blizzard to get here.

Eventually our conversation drifted to making a plan for the day. “Okay so… I have a client soon, I’m gonna need you either outta here, or squirreled away upstairs, your call. And after that… I dunno. You feel like helping me carry groceries?”

Crook just shrugged. “Sure. You can show me around town or whatever.”

“There isn’t really much to show.” I pointed at the plates. “Now wash this shit, would you?”

“What? Just get your...” He paused with realization. “…Oh, right… no gofer.” He just shrugged, collected our dishes,and trotted to the kitchen. For a moment I just sat and enjoyed the sounds of someone else doing the dishes. It had been a long-ass time since somepony had been here who wasn’t a client.

And that somepony was Applejack. She stopped by when I first moved to town to yell at me.

That was not a good day.

Regardless, Crook finished up and opted to lock himself upstairs in my bedroom. It was a bit unorthodox, but I trusted him to keep his head down. After all, he understands the nature of the job. He knows that even the slightest thing being off can ruin a client’s experience.

So together the two of us prepared my home for a visitor. He helped me make the bed, helped me shovel the entrance. He helped me get candles and a fire lit. He even helped me pick out music. After the house was ready, he headed off upstairs, while I awaited my client, Junebug.

Junebug is an ‘every-now-and-then’ with a penchant for small talk. She’s a florist; she grows and sells flowers in the market. She’s pretty good too. I’ve walked by her stand a few times; there are some good looking bouquets there. I’ve always found flowers a little confusing… I can never decide if I wanted to eat them or put them on display. Still, they’re easy to talk about. I’ll usually bring up a few flowers and she’ll tell me a thing or two about them. Simple stuff. She’s very amiable, always happy to tell me anything I want to know.

Her knock came right when it should have. I double-checked my bedroom door, to make sure Crook was sequestered away, and I opened the door. Dressed in scarf and coat, she stood outside my little cottage. It was a chilly morning, but any traces of last night’s wind were long gone, making it somewhat… I want to say brisk is the word. It was a brisk morning.

Anyways...

I donned my dashing grin. “I hope the walk here wasn’t too nasty. We had quite the blizzard last night.” I said as I bid her entrance.

She cracked a smile as she came in. “No, it was just fine. Thank you for asking, though.” I gestured for her to hoof me her coat, which she did, and I promptly hung it.

“The snow wasn’t too deep?” Appearing concerned always makes a client feel like their needs are being catered to. It never hurts to double-check if everything is okay. After all, some ponies’ natural instinct is to forgo their own wants and desires. This can make catering to a pony’s needs… troublesome. So… always double check.

Never triple check though… then you just seem like a worry-wart.

She giggled somewhat merrily at the attention I was giving her. “The snow was just fine… I think the weather team cleared a lot of it this morning.” She made her way to the table in my foyer, and took her seat.

“Would you like some cocoa? Or tea?” I offered like a good little escort.

“No, I’m okay. It’s plenty warm in here.” She smiled. She has such a tender smile. “Thank you, though.”

“Well in that case…” I sat across from my client. “…How are you, Junebug?” I didn’t have to fake a smile, it came naturally.

“I’m well. Things are going fairly nicely right now. Business is always good in the winter.”

I cocked an eyebrow at that. “Oh? How’s that? I would’ve assumed you’d shut down for Winter.”

She shook her head. “Mmm-mmm. I have a green house. And in Winter, ponies can’t go around picking wildflowers.”

“So they have to go through you to get their precious flowers?” I joked.

“Exactly. Mwahaha!” She laughed mock-evilly.

I giggled.

“But as you know,” she continued “there are a few florists in Ponyville. I’m afraid I don’t have a monopoly like you do, Mr. ‘Ponyville’s Only Escort.’”

“It does have its perks.” I admitted. “I never have to worry about ‘healthy competition.’ Speaking of, is Roseluck still screwing with you?” I inquired. Apparently this one mare has a tendency to undercut Junebug’s prices fairly consistently.

“Ugh…” Her expression soured. “Every time I have a sale… so does she. Whenever I put up new prices… she puts up ones that are just a bit or two less. I don’t even think she’s trying to hide it anymore.”

Comforting smile. “Well… I’m sure she’s just desperate because she knows that she has an inferior product.”

Junebug snickered. “Thanks. That makes me feel better.” She quickly threw on a false ‘high society’ accent. “You should see her bouquets, though. Her use of Baby’s Breath? Just gaudy.”

I laughed, but not because I thought it was all that funny. I laughed because she sounded remarkably like Rarity. She always sounds like that whenever the topic turns to fashion.

A question occurred to me. “Okay, so… What is baby’s breath? I’ve heard ponies mention it, but I never really knew… what it was.”

“Oh, it’s the little teensy white flowers you see in bouquets sometimes. You usually use it to fill in gaps between bigger flowers.” She explained.

“Huh. Well, you learn something new every day.” I mused. I was rather enjoying myself. Junebug’s interesting, funny, witty, more than a little cute. It’s nice talking just to talk sometimes.

“So how are you, Guilty?” She asked. “Anything interesting going on?”

‘The librarian and her boyfriend got into and fight over me, and she broke his nose (maybe.) My best friend showed up unannounced at my doorstep and just barged into my life. He’s upstairs right now, hidden away. I screamed at a kid and made him cry, but it was an accident.’

“Nothing much… I’ve been thinking of ordering some snowshoes. That’s about exciting as it gets all the way out here.” I lied with a grin.

“Supposed to be lots of snow this year.” She said. “That probably means a lot of business for you, right?”

I tried to follow her logic to no avail. “What makes you think that?”

She shrugged. “I dunno. I figured ponies would all stop by to… you know… warm up a little.” She tried to be subtle about her implication. She was not. She could’ve done without the eyebrow wiggling and I still would have gotten her meaning.

“Actually, Summer sees the best business.” I explained. “When the night is so hot you can’t sleep. When you spend all day sweating. When the heat gets under your coat. That’s when ponies… need it.”

“Makes sense.” Junebug began to half-lid her eyes at me. “Well, I’m not sure about other ponies. But I think that I need it. Right now.”

Clumsy and obvious as Junebug was, she made her point. It was time for sex.

‘So soon? Oh well, it was nice while it lasted.’

“Well then… to the bedroom.” I smiled falsely. I hid any trace of disappointment from my voice. Never appear discouraged; it tends to hurt the client’s feelings.

Now… I really enjoy the small talk I usually share with Junebug, as I’ve said. But sex with her is… a chore for me. Not that there’s anything wrong with her. I’m sure there are plenty of ponies who would fully enjoy providing this service to Junebug. I’m just not one of them.

See, Junebug likes to be dominated.

I’ve never really understood the whole BDSM… thing. Honestly I’ve always found it rather silly. Now I don’t have an issue with taking a particularly active or a passive role in sex, but this is different. The whole premise of pretending one pony is at the mercy of another is just weird to me. It makes sense to the ponies who do it I imagine, and I’m sure as shit not one to judge. It just doesn’t float my boat.

As we went to the bedroom, I prepared myself for the act. It’s not easy for me to be so dominating so naturally, it takes a bit of forethought. I have to appear controlling. I have to appear merciless. I have to appear sadistic.

I am none of these things.

“So… on the bed… let’s get you tied up.” I delayed slipping into the act for as long as I could. I was still just… Guilty.

“O-okay.” She was already so hungry for it. Her whole body was shaking from excitement. I get the feeling that she doesn’t masturbate. She always seems so… backed up. She’s not seeing anypony either, as far as I know. I might just be her sole source of orgasm.

I pulled a length of rope from one of my many trunks. “Lay still.” I instructed. She instantly complied, ever eager. And with that, I began the lengthy task of binding a mare.

Now, if I may split hairs. I don’t bear any particular disdain for bondage itself. The sensation of ropes or cuffs or whatever can be very enjoyable in moderation. Bondage isn’t inherently about control. Sometimes cuffs just feel good because they do. I only take issue with the whole… mind game that comes along with sadomasochism.

I’ve actually gotten pretty darn good at tying up mares. I never had a knack for it when I was starting, but I improved with time. Knots and ropes came as second nature anymore. An intricate pattern across her torso. Her flesh bulging around each line of rope. Her tail tied into a permanent lift. He fore hooves bound to her hind hooves, and placed flat under her. Her rear end stuck high in the air. Her hind legs spread far, opening the lips of her marehood. It was all so easy now. I decided to top it all off with a blindfold. She dug it, thankfully.

Oh for the record, I use a nylon rope. Regular rope takes a lot of preparation, otherwise it just fucking hurts. Trust me.

With the deed done, I had only one thing to do before I had to begin. I guzzled a blue flask down and began my act.

“Tell me Junebug. Have you been a bad pony?” It was an obvious line, but I couldn’t help it. Honestly I feel restricted creatively when I have to do this.

“N-n-no.” She whimpered, already completely dedicated to the act.

I opened a nearby trunk, making extra sure to do so loudly. Unexplained noises can add to the tention. “Don’t lie to me Junebug. You know what happens when you lie to me.” My voice became deep and raspy. I don’t think I’m very good at sounding mean. I feel like I sound comically sinister. Still, Junebug seems to enjoy it.

“N-no! I swear! I’ve been good!” She’s actually quite the actress. She sounded genuinely distressed. I suppose that’s part of what makes this so hard for me; I don’t like hurting ponies. In the end, this whole thing is her idea but… still. On some deeper level it just feels so… wrong.

“You’re lying.” I hissed. I produced a paddle from my crate. Her favorite.

She began to plead. “No… it’s… it’s the truth. I swear, Guilt-”

*WHAP!*

Despite my every inclination I struck her on the behind, silencing her completely. My teeth dug into the grip. The wood tasted sour in my mouth.

“GUH!” She bellowed.

“That’s ‘Sir.’” Ugh… It felt so stupid. Such… needless animosity.

“S-s-s-sorry.” She whimpered.

*WHAP!*

“MMMF!” She drowned he scream into the cloud beneath her.

“Sorry, what?” I asked

“S-Sorry Sir!” She quickly responded.

“Gooooood.” I crooned as I ran a delicate hoof across her tender backside. “Now… tell the truth… you’ve been a bad pony haven’t you?” I took up my paddle once more, ready for more swings.

“No, sir. I haven’t!”

*WHAP!*

“AAAH!” She cried.

I brought my voice to just above a whisper. “You. Are. Lying.” I find that speaking softly can be just as intimidating as shouting. It’s also much easier on your throat.

“I swear, sir. I’ve been a good pony! I’ve been a-”

*WHAP! WHAP!*

I put two swift strikes across her cheeks, which were beginning to get swollen and red.

“Okay! Okay!” She was wheezing, voice shaking like a leaf. “I-I’ve been a b-b-bad p-p-p-pony! I’ve been a baAAHAAHAAD PONYYYYYYY!”

And then came the waterworks. She was bawling.

‘Why does she like this? Why does she want me to make her cry? Who wants to cry?’

If she didn’t have a safe word I would’ve ended everything right there. Normally when one of my clients breaks down into tears everything comes to a grinding fucking halt, but apparently she didn’t want me to stop yet. She wanted to keep playing.

“Sshsshsshssh, It’s okay.” I climbed up onto the bad and over to her face. I gazed at her messy face. Tears were wetting the blindfold, putting to dark eyespots in the fabric. Mucus was dripping from her nose. “Oooh… so pitiful.” I playfully flicked at her ear. “Don’t worry, dear. Your punishment won’t be too severe.” I like to always appear sympathetic. It makes me feel somehow better about the whole ordeal.

“M-m-mmmh-h-hmmmm” she whimpered. I pulled myself off the bed and took up my paddle once more. Her ass was swollen red now, and her lips glistening and pink. I bit into grip and swung my neck hard.

*WHAP!*

When spanking a mare, it’s always important to swing just hard enough to hurt, but not hard enough to harm. No client wants to end up walking around all day with scars on their ass.

*WHAP!*

A paddle works well for this. It will certainly make an ass red, but it won’t really cut them or anything. Ponies who use whips and such have to be extra careful.

*WHAP!*

There’s something else that’s important to keep in mind. Counterintuitive as it may seem, I cannot emphasize it enough. The sub is always in control.

*WHAP!*

The sub is the one putting themselves in a dangerous position. No matter what the dom wants to do, if it isn’t okay with the sub, they don’t do it. That’s why a safe word is important.

*WHAP!*

A dom has to be able to recognize when a sub is pretending to hate it, and when they actually hate it. A sub has to be able to make it clear that they want their dom to stop.

*WHAP!*

This can be difficult at times, particularly when the sub is gagged and bound. In these situations you still need a signal that can be picked up on by the dom: rapid blinking, a series of short grunts, anything.

*WHAP!*

The best thing a pony can do, however, is to always make sure they trust the pony they’re playing with. If your partner genuinely cares for you, they’ll be much less likely to go overboard.

*WHAP! WHAP! WHAP!*

After ten solid smacks her back end looked remarkably like a tomato. Her marehood was dripping onto the mattress. Her mouth was fixed in a silent scream, drool dribbling down her gaping lips. Even obscured by pain, I could still see the ecstasy on her face. She loved every second of this torment.

“Now… that wasn’t so bad, was it?” I sidled up against her again. “Are you sorry?” I petted her head affectionately.

“Y-y-y-yes.” She tried to hide the pleasure from her voice, but it was still evident in her tone.

“Say it.” I insisted.

“I-I’m sorry that I was a b-bad pony.” She said through her quivering.

I laughed. A big goofy evil chuckle. “No. Nonononono, stupid girl.” I think I hate berating her the most. The first time we did this I wasn’t degrading at all. Next time she asked me to insult her a lot more, so... it’s just part of the routine now. “That was for lying to me. I still have to punish you for being so…very…bad.”

I violently flipped her onto her back. She gasped in surprise, as she found her legs tied spread in the air. “Now… tell me Junebug.” I place a hoof sternly on her pussy. It was so very hot and wet. “Why are you a bad pony? What did you do that was so bad?”

She was still struggling with her new orientation when she answered. “I… I don’t want t-”

*Smack!* I give her crotch a delicate yet forceful little slap. “It’s not about what you want!” I seethed mock-angrily. “It’s about what you have to do!”

“N-n-n-no!” She pleaded.

*Smack!* “Tell me.” I insisted.

“I don’t wanna! I don’t waahaahaanna!” There were the tears again. Every drop and every sob ate at me. Everything about it just felt so… dirty.

An idea occurred to me. A strategy I hadn’t used in some time. “Oh… you don’t want to? Then I’ll make you want to.” I slid my face up to her crotch, letting my breath tickle her. I gave her a slow purposeful lick, relishing in her flavor. She squealed in surprise and delight. “Do you like that?”

“Y-yes…”

*Smack!*

“Yes, sir!” She quickly corrected.

“Good… then here’s what’s going to happen. You don’t get to come until you tell me alllllllll about the bad things you’ve done.” My words felt forced. My normally excellent dialogue skills were failing me.

This was fine. Good even. Delving into her moist folds, licking up her juices, I could focus on the task at hoof. Probing and tickling and sucking and kissing and lapping, it was very calming. I proceeded carefully, not to allowing her over the edge. She tasted so good. Eventually I pulled away from her, leaving an aching quivering pussy to suffer from deprivation.

“D-d-don’t stop!” She implored.

“How about now? Do you feel like talking?” I ignored her pleading entirely.

“Oh pleasepleaseplease don’t stop!” She didn’t just sound desperate, she really was. She craved release.

“Oh, but if I keep going, you’ll finish right now… and we can’t have that, now can we?” I ran a hoof across her lips delicately: just enough stimulation to keep her on the precipice.

Her whole body shook in frustration. She gyrated her hips within her bindings in a vain attempt to eke more pleasure out of my hoof.

“Well go on… tell me all the bad things you’ve been doing.” I taunted her.

She listed off a number of apparent misdeeds she’d performed over the past week or so. Lying to a friend to get out of a favor. Sneaking extra snacks from the fridge. That sort of thing. Finally, though, she said something that was rather interesting.

“I… I… I… I had naughty thoughts!” She blurted.

“Oh?” I was actually kind of curious about that. “Do tell.”

“There’s a stallion… his n-n-name is Baritone.” She shakily explained.

“And?”

“And he c-c-came by to buy some daisies for p-p-picnic… w-when he left, he s-smiled at me.”

“And?”

“And I when I got home I k-kept thinking about him…”She continued.

“About him how?”

“About him…. on me… touching me… holding me…”

“Fucking you?” I offered.

Fighting back a sob, she nodded.

I chuckled. “You know something Junebug?”

“W-w-what?” She asked nervously.

“You are a bad bad pony.” With that I dove into her legs with renewed vigor, my tongue slithering into her. Within a moment she was already screaming in pleasure. She came quickly. The ropes stretched as her muscles tensed, orgasm pulsing through her body. A splash of hot liquid hit my tongue. She came so hard she wet herself. This is a thing that happens sometimes. It’s called stre-

I’ve already explained this haven’t I?

Anyways…

I removed my head for betwixt her hips. I couldn’t help but gaze on as she continued to leak onto the bed. Her liquid flowed onto the sheets, staining them. There were tears streaming down her face, but her lips were bent into a smile.

“Oh… look at that. You made such a mess.” I observed.

“I’m sorry, sir.” She was floating on a cloud of ecstasy.

“I suppose I’ll have to punish you for that too.”

“Okay!” She said eagerly. She could no longer even pretend she was not enjoying herself.

I rolled her off of her mess and flipped her over onto her back. Her ass once more propped into the air, I mounted her. “Since you’ve been such a messy pony, I think I’m going to fuck you.” I said as I wriggled out of my jeans. I sounded so corny.

“Okay, Sir!” Her ass twitched in anticipation.

I thrust into violently. She usually asks me to be rougher, so I figured I’d go all out from the get go. She was more than ready for it. Her body accepted me quite easily. She was moist and loose and so very hot.

I’ll say this. A lot of guys will speak ill of girl who is ‘loose’ in the literal sense. Honestly it doesn’t make sex any more or less enjoyable. Tight or loose, the experience almost always feels good.

I pressed as much of my weight onto her as I could. Any sort of pressure served to heighten her experience. I fucked her hard and fast, and she enjoyed it thoroughly. Each thrust punctuated by the wet slapping noise of flesh on flesh. I rattled off insults when they occurred to me. I called her a slut and a whore and a bitch, much to her satisfaction.

Now, there’s a very important thing that one must do both as a dominator and as an escort.

One must never make it personal.

I don’t know why... but when I was fucking Junebug and insulting her and everything. My false anger… started to turn real.

Now part of the problem was Junebug herself. She didn’t do anything to make me angry it’s just…

She kind of looked like Carrot Top. Especially with that blindfold hiding her face. Her colors aren’t quite right, and her mane is styled a little differently but... the similarity is there.

For a few seconds I was… furious. I’m not even all that mad at Carrot Top, it was just… with the role-playing and that hike we had and Crook showing up and the whole Spike-Twilight incident... I had a lot of emotions all bubbling near the surface and…

I dunno.

I caught myself though. For a few moments I was as mad as I’ve ever been, but it didn’t last. I just reminded myself that I was with a client and I just… swallowed all my anger.

Once I calmed myself I proceeded to fuck my client with good, old-fashioned, fake fury. Through the insults and thrusting and sweating I managed to make her come again. She wet herself again as well, splashing my testes. It honestly didn’t bother me. It was just pee.

Her climax begat mine. I emptied myself deep inside her as her hot walls clenched me. She likes me to finish inside her. Mares often do.

For several seconds we just enjoyed the moment. I felt myself slowly soften within her as she shivered in delight. Regardless of the session itself, I can always appreciate a job well done. Eventually I dismounted her, and lay myself down beside her.

Another thing to keep in mind when being a dominator, is when it is okay to break character. Breaking character can ruin a pony’s whole experience if done too early, so try to get a feel for when the sub is finished.

She was definitely finished.

“How was that?” I asked, allow my voice back into its normal cadence.

“Amaaaaaaaaaaaaaaazing.” She responded drunkenly. I removed her blindfold to meet her gaze. Her eyes were puffy and her face was still covered in tears and mucus, but she looked… grateful. I may never understand exactly what pleasure she gets out of her session, but I’ll always be happy to provide it. “Thanks again, Guilty.” She chuckled somewhat ashamedly. “I…I think…shower…”

“Of course.” I untied her carefully, the ropes had worn into her skin a bit, but they marks they’d left would fade soon enough. Junebug likes to shower alone, so while she trotted upstairs I washed my face in the kitchen sink. I was still going to shower afterwards, but it let me wash the smell of pussy and urine off of my face.

She finished up and met me back downstairs. I’d prepared some tea, just in case she felt like some. She did not.

“So… hehe… thanks again.” She’s always embarrassed once the session is over. She was blushing hard.

“Not at all, Junebug. Your business is always appreciated.” Sexy grin.

“O-okay. Here’s *ahem* forty.” She produced a small pouch of coins from her hanging coat, which she then put on. She’d only just broken into her second hour, but she still saw fit to pay for it.

I wasn’t going to argue.

“Thank you so much, Junebug. Do come back.” I gracefully took her pouch.

She began to make for the door. “I-I will. See you then.”

“Of course. Bye now.”

She nodded, and with that she left. She often leaves rather quickly after her shower, but lots of clients are like that. Some are ashamed, some are embarrassed and some just want to go home. Either way, it’s no big deal. Honestly part of me was glad she left so quickly. I really needed a shower.

First, though, I had to let Crook out of my room. I figured he’d be going stir crazy up there all alone. He’s not the sort of stallion who can really sit still. I trotted upstairs and went to my door, and when I opened it I found him lying on my bed, taking a belt of whiskey.

“Wha- Where did you get that?” I asked, knowing full well the answer to my question.

He coughed loudly. “Liquor cabinet.”

I threw him a look.

“Oh relax, I’m not even down to the label.” He snickered and handed me the bottle. I just put it on the floor.

“Crook… it’s ten-fifteen.” I chided.

“Hair o’ the dog, Guilty. Hair o’ the dog.” He hopped out of bed. If nothing else he appeared sober. He looked me up and down. “You gonna shower?” He asked.

“Yeah”

“I’ll join you… I smell like fuck.” He ran a hoof over his face.

“You smell like whiskey.” I chided him again.

He just rolled his eyes.

“When did you even grab this?” I began to wonder if he hadn’t snuck out during my appointment. As good as escort as he is... he’s still Crook. I wouldn’t put it past him.

“I stowed it up here while you were fuckin’ with the phonograph.” He explained.

“For fuck’s sake, Crook.” Still, it was better than the alternative.

“Yeah yeah yeah...” He said. And then the little confrontation was over.

So, the two of us hopped into the shower. We used to shower together all the time. Crook eyed my collection of soaps and shampoos. “You use all of those?” He asked.

“Nah, I use this vanilla peach stuff mostly.” I pulled the bottle off of the shelf.

Crook snorted. “You’re such a queer.”

This time I rolled my eyes.

The water in the pipes was still warm from Junebug’s shower, which was a good thing because those pipes get really cold in the winter. Crook grabbed the cheapest shampoo he could find and proceeded to wash himself sloppily. I offered him a loofa, be he declined. I opted to use one myself. The loofa felt good on my skin. It was so rough and cleansing. It felt like it was cleaning everything off of me… everything out of me. It felt so good to scrub scrub scrub get clean clean clean.

‘Oh no…’

I could feel it coming. I was going to have a fit. I was going to scrub and clean and wash and cleanse and brush and scrape until my skin was raw. I was going to freak out. I had to stop. I had to stop myself.

I violently threw the loofa on the shower floor. My breath had become labored, and Crook took notice. I tried not to look at him… I was… I was too embarrassed. I was so ashamed… perhaps as ashamed as Junebug.

He understood right away what was going on. The next thing I knew I felt the loofa on my back. “Nice and slow, Guilty.” Crooks voice came so gently. Gentle didn’t suit him, but I was grateful for it. “One scrub at a time. Deep breaths. Just like Mama taught us.”

I cringed slightly. I honestly didn’t want to think about her.

Crook continued to clean me, scrubbing my neck and beck. “This happen a lot? I haven’t seen you like this in years.”

“Ju-ust...” my voice was cracking; I cleared my throat. “Just a couple times.”

There was a long pause before he spoke again. He finished up with my back and began washing my ears and mane. “Y’alright?”

“Yeah…yeah I’m fine.” I didn’t sound entirely sure of myself. I wasn’t. It felt really good to have someone wash me. When I was starting out I used to get cleaned by other escorts every now and then. If I was freaking out in the shower and someone saw me, they’d always offer to wash me. Better than having me scrape of a layer of skin. When I got a little older and a little more jaded, I’d sometimes do the same thing for the kids starting out. It’s just sort of… a thing amongst us escorts.

As I pondered on my time in the stable Crook continued to clean me. When he was done he put down the loofa, capped my fragrant shower gel, and turned off the nozzle. The din of the shower died to a quiet trickle, as water drained from the pipes. I was feeling better, but still somehow on the verge of tears.

I felt a hoof wrap around my shoulder. “You’re okay, Guilty. You’re okay.” I looked up at my friend, to find a friendly smile looking down at me. I’m not sure why but that smile made the tears flow.

So, I cried. Soaking wet, and being held by my best friend, I cried my eyes out. I bawled until snot ran down my face and my eyes grew red and puffy. I cried like Junebug cried when I paddled her. I cried like I cried on that night not too long ago, all alone. I bawled and cried and howled and wept and wailed into Crook’s shoulder.

There was just… so much emotion in me. So much raw fucking emotion. Happiness and sadness and anger and misery and fear and hate and love and just fucking everything. So much inside me that just needed out.

It just felt… it just felt like it was okay when Crook was there. It felt okay to feel all of these emotions that had been stewing inside of me. Crook was always there for me when I needed him, and it would appear he still is. Fuck, I missed him.

As my wails began to give way to hushed sobs, he said it again. “You’re okay, Guilty.”

“Y-yeah.” I whimpered before pulling myself together. “Yeah, I’m okay.”

Crook snickered and removed his hoof from my shoulder. “What… no ‘thank you’? You’re welcome, asshole.” He punched me in the shoulder again.

I love him for that. He just, moves on and pretends like nothing happened… but in a good way.

“Thanks.”

“Damn straight. Now… what’s the plan? I’m thinkin’ lunch soon, we gonna head into town?”

“Lemme... *ahem*... lemme clean up, and we’ll get going.” I responded, removing any leftover sadness from my voice.

Wow… fuck. It’s late. There’s a lot more to write, but I have to get to bed. I’ll write more tomorrow.

Author's Notes:

Hope you enjoyed! Thanks again for reading. Don't forget to tell your friends about Guilty's Exploits.