Dear Red Shoes,

Ponies are very risk-averse creatures. Whether it's courting another pony, buying groceries at market, or even deciding whether to go out in the rain, we like to play it safe. Well, most of us, anyway. Me? Let's just say that risk comes with the line of work I keep - both official and otherwise. In the right situation though, even this risk-taker will step outside of her limits... Especially if it's the last thing I thought I'd ever do.

"Hey! I said, hey! Meathead!"

Heh, he's trying to ignore me. What a louse.

"Hello! Anyone home out there? Sleeping on the job again, Meathead?"

I could hear the tapping of a hoof a few feet behind me. I knew she was getting impatient; probably wanted me to just shut up and sit back down. No, wait, that's not her 'impatient' tap, that's her 'I'm just waiting to see how this blows up in your face' tap. And when does Rainbow Dash let her Captain down?

"Oh, I see, you just can't hear me, right?" I began tapping my hoof loudly against the iron bars that caged us. "Well, can you hear me now? Or are those ears as small as whatever that is hanging from your fat gut?"

I heard a chair scrape across the floor and a set of keys jingle against the lock to the outer door. Ha, that got his attention.

The door opened with a cringe-inducing squeal and the rather rotund guard stormed right over to the cell door. "Oh, my sincerest apologies, ladies. I'm so sorry for the slow response time. That's certainly not the type of service that you deserve from the Hotel Revolution."

"Hotel Revolution? Really?" I asked with a laugh that quickly turned into a cackle. "You guys can't even think of a cool name for your makeshift prisons, much less your little revolution." I glared at him again as anger rose in my throat for what felt like the millionth time since our capture. "What do you think you're going to do, huh? Overthrow Celestia? Ha! You couldn't take over Dodge Junction, much less an entire kingdom."

He struck his club against the bars hard enough to make my ears hurt. "We must not be that bad; after all, we did capture two of Equestria's best spies at the same time."

"I told you, we're not spies-"

"Save it, rainbow-mane. We know what the Wonderbolts do when the curtain goes down. While you're busy wowing the stupid crowds with your air shows, you're sneaking around behind their backs, doing the dirty work that Miss Goody-Four Hooves Celestia doesn't want anypony to know about." The unicorn guard sneered at us, his ugly yellow teeth showing themselves again. "Well, everypony's going to know, now that we have you two."

I turned that over in my head for a second before I realized what he was referring to. "Oh, so the grand plan is to ransom us to Celestia? You know she's not going to pay you, right? She'll burn this place to the ground before she gives you idiots one rusty bit for trying to usurp the throne."

"You fool," he retorted as he leaned his nose to the bars. "You think we want money? Ha, we have no need of it, not with our mole in your Treasury laundering bits to us every month. No, we just need you to make a point; to send a message."

"If you wanted a mouthpiece, you could have just hired a spokespony with all of those funds you're supposedly taking from us."

"Oh, we won't need words to send the message we have planned for Dear Celestia. The only thing we'll be sending her are your wings." He unsheathed a long knife from the holster on his foreleg and ran it up one of the iron bars; the sound was like hooves on a chalkboard, only much, much worse. "Right after we cut them off, that is."

I wanted to blanch in horror at the very idea, but I was seeing too much red to care. I turned and bucked the cell door, the bars stopping my hind legs just inches from his ugly face. "Go ahead, do it! You'll never escape Celestia after that. She'll hunt you to the ends of the world."

"That's just what we're counting on, feather-brain. We're counting on both Princesses leaving their posh castle to chase us... And by the time they realize what's really happened, we'll have already changed the locks on the castle doors."

I flared my wings and snarled at him in response, but he smiled all the more as he backed away from the cell. "Have a good night, ladies. And do try to get some rest. We don't want you falling asleep right before we hack you to bits... It won't look nearly as good in the pictures we'll be sending to every newspaper in Equestria."

He chuckled like the ass that he was while slamming the outer door in my face. My rage got the better of me and I screamed out after him - only for my voice to bounce right back at me, dropping me back to my haunches. "Ow! What the-"

"Standard silencing spell. Guard fat-flank cast it on the door as he left; you'd have noticed, if weren't trying to needle him all night."

I whirled around with a bit of anger still in my vision. "What was I supposed to do, huh Spitfire? Bat my eyes, play nice, and hope he lets us go because we're so charming?" A second later, my mind caught up to my tongue and I realized to whom I had just lashed out. Oh, buck. "Um, m'am."

Spitfire - or I should say Captain Spitfire - sat against the back wall of the barren cell, her half-broken sunglasses twirling in her right hoof. She looked at me for a moment before laughing a bit. "All these years later, and you still didn't mellow out much, did you? I mean, you just talked to me the same way you did when you stood in my office and berated me for making you wing pony instead of lead pony." She stood and smoothed her torn, dirt-stained uniform as best she could. "If you were anypony else, Dash, I'd bust you down to Private for that outburst; heck, I'd have done it long ago to be honest, but you're too good at what you do."

I smiled at that, but it was short lived. I huffed in frustration before moving to the seriously uncomfortable bed that was the cell's only furnishing. "Yeah, well good didn't cut it, did it? Princess Celestia sent us to gather intelligence on this group of crack-pots, not get caught and sentenced to an early grave." My shoulders sagged as I leaned back against the cold brick wall. "We're really screwed, aren't we?"

I looked over to Spitfire, who just stared ahead for a second. I could tell she was lost in thought, but managed to hold my tongue for a second. "Hate to say it, but you might be right on that." She sighed as she ran a hoof through her orange mane. "Only Celestia knew about this covert op, and by the time we miss our next scheduled report, it'll be too late anyway."

"Don't remind me," I muttered as I pushed off the useless bed and paced the cell in a small circle. After a moment, I turned back to Spitfire and offered her a small salute. "I'll just say it now. It's been a pleasure and an honor, Captain."

She returned my salute with a smile. "Likewise, Commander Dash, likewise."

I was racking my brain for something else to say when she beat me to the punch. "So, any regrets?"

That was an odd question, especially coming from the always straight-laced Spitfire. "Regrets, m'am?"

"You can drop the rank now, Rainbow; I think we're well past titles at this point. But, yes, regrets; things you wish you had done before kicking the bucket." She idly waved a hoof in my direction. "Or did you manage to manage to check off your life to-do list in ten seconds flat as well?"

"Hmm..." I made a show of mulling that over, but in truth, I was torn. Do I make something up, or tell her the truth? I knew what I really wanted to say in response, but how would she react? Would she laugh at me? Or laugh at me before doing the executioner's job for them? That's when it hit me like a sack of apples. I was a dead pony come morning. We came in alone, and any backup or rescue would never get here in time. Got nothing to lose now...

"Actually, I do." I turned to Spitfire as I let my deepest, and probably longest-held secret spill out. "I wish I would have tried to kiss you."

I just stood there and looked at her, studying her face for any sign of a reaction. I had spilled the beans big time, and for a moment, the air felt like a hundred pound weight on my head. Finally, Spitfire stood up, tucked her glasses into her shirt pocket, and walked over to me. I shuffled back a bit but quickly hit my rump against the wall, leaving me nowhere to go. She stepped right up to me, leaving less than a foot between us, and stared at me for a moment. "Is that so?"

Words failed me then, and I could only nod my head in response. Every part of my body tensed as I braced myself for the tirade - and the slap - that I was sure was coming any second. Then, out of nowhere, a wicked grin crossed her face. "Well, it's a pity then that we won't make it back to base."

"W-why's that?"

She leaned in close enough for me to feel her breath across my nose. "Because Soarin owes me a hundred bits now." Before I could even process what she said, her lips were on mine. My mind froze for one second in shock, then quickly melted into a delirious haze. Spitfire wasn't just kissing me, she was kissing me; and Celestia help me it felt so good.

Finally, my brain caught up with my pulse, and my lips began to return the favor. For as hard-edged as Spitfire was normally, in that moment she was as soft and pliable as a cloud. I could feel a gentle heat behind her kiss, and it was incredible. My wings were jittering at my sides, threatening to unfurl in a very obvious manner. Then she broke the kiss with a flourish, swiping the tip of her tongue against my lips as she pulled back.

"W-wow, that was... I mean-"

"Heh, of all things to finally leave you speechless..." Spitfire smirked a bit as she looked me over. It was only one kiss, but I was already a panting mess. My pulse was racing, my entire body was tingling from surprise and more than a bit of adrenaline, and my wings were barely staying close to my sides. Finally, my voice found its way back.

"Y-you had a bet?"

"More like a friendly wager," Spirfire replied. "Plenty of cadets and Bolts have given me more than a passing glance over the years, but none of them ever had the guts to act on it. That is, until you came along."

"Me?"

"Soarin figured that the only pony to ever walk into my office, berate me, and quit would show a similar lack of compunction in making a pass at me. I told him he was joking, and we decided to make a friendly wager." She licked her lips in satisfaction. "And I must say, I'm very glad that I won."

My heart skipped a beat. She wasn't just okay with it, she enjoyed it! And if the look in her eyes was any indication, she might not mind another kiss, either. Before I could second-guess myself, I stepped closer to Spitfire and looked right into her bright orange eyes. "Permission to speak freely?"

"Granted." The husky tone in her voice was unmistakable, and it spurred me to continue.

"You know," I said quietly, "fraternizing with other Wonderbolts, especially junior officers, is clearly against the rules."

"Hmm, you make a point there, Rainbow. In this case though," She turned her head and whispered in my ear. "I'll allow it."

The next thing I knew, my back was against the wall, Spitfire's lips were plastered against mine...

...and I was in heaven.

Where her first kiss was smooth to the point of gentle, this one was hard and passionate. Her lips felt like hot coals against me, and I melted into her without hesitation. She paused for a half-breath and I took full advantage of the opening, wrapping a hoof around her head and pulling her lips back to me. Our tongues seemed to meet in the middle as I kissed her as deeply and passionately as I could. My heart was racing, my mind a haze of delirious joy.

Yes, Spitfire was my commanding officer, but damn it all she was gorgeous. I had pined for her since my first day in the Academy. I thought it was just a celebrity crush at first, but as time went on, all I saw in my dreams was her. Not Spitfire the Captain, not Spitfire the Wonderbolt, just Spitfire the pony. The beautiful, graceful pony that occupied my every fantasy.

In the back of my mind, I knew we were both doomed come morning, and maybe, just maybe, this was an act of mutual recklessness. But at that moment, with the mare of my dreams crushed against my chest, her scent in my nostrils, and her tongue entwined with my own, I couldn't have cared less.

"Oh, wow..." I panted like crazy as the need for air finally overcame my desire to not stop. "You're too good."

Spitfire ran a hoof through my mane, her eyes as smokey as I had ever seen them. "That? Heh, we're just getting started, Dash."

I opened my mouth to respond, but all that came out was a low groan as Spitfire's lips snaked through my mane to the base of my neck. If not for her weight against my chest, I'd have collapsed onto the floor from the sensory overload. Her lips left a trail of fire down my neck, while her hooves began tracing down my primaries. We pegasi have pretty obvious hot buttons, if you know what I mean, and she was hitting them all at once it seemed. My wings went stiff as a board under her expert touch, and I could already feel the heat building in my haunches. "P-please, don't stop- Oh!"

Spitfire's lips crossed the hollow of my throat and began a slow but steady trail of kisses and nibbles down my chest. I dropped my hooves onto her shoulders and shuffled my hind legs out from the wall for more stability. My back arched out on its own, as if inviting, no begging her to continue. My eyes were glazed with lust as I watched Spitfire work her way down my barrel, nipping, kissing, and licking nearly every inch of my belly. Her hooves finally left my wings and traced down and around my sides before brushing my already rock-hard nipples. Desire, lust, passion... They all mixed together to send me into overdrive. Sweat was dampening my coat, arousal was dripping from my haunches, and all I wanted was more. "Oh, yes! Don't stop, please!"

"That excited already, are we?" Spitfire cooed as her hooves continued to trace lines through my fur and down my sides. "Too bad it took getting captured to get to this point." A debilitating shudder raced up my spine as her hoof ventured crossed the crease of my inner thigh and towards my haunches. "Tell me, Rainbow..." The tip of her hoof grazed my soaked outer lips. "Any last requests?"

I looked down at Spitfire with nothing but lust in my eyes. "Make me cum, please."

"Well, don't say I never did anything for you." Spitfire planted her tongue into my haunches, and my heart nearly exploded. She went straight for my marehood, parting my soaked outer lips in one smooth motion. If I was on the verge of overload before, this sent me flying over the edge in an instant.

"Aahn, yes! D-don't stop, y- Oh!" The rush of adrenaline and raw arousal racing through me was beyond intense. I cried out all the louder as the mare I lusted after for years explored every inch of my center, and all the while, her hooves never stopped caressing my nipples or massaging my cutie marks. My nerves were on fire, every feather on my body was standing on edge, and as I felt Spitfire's tongue dart past my inner lips, I nearly crumbled into her hooves.

"I... I'm so close- Oh, yes, don't stop!"

"Hmm..." She only hummed contentedly as she pressed deeper into my core, lapping up my juices like it was her last drink. I could feel an orgasm racing through me, building and building like a runaway train, and there was no way in Tartarus I was going to even try to stop it. I simply cried and moaned all the more, arching my back to give Spitfire's eager tongue as much access to my dripping center as possible. Finally, her tongue found my clit, and the orgasm ripped through me in an instant.

"Aahn, YES!" My whole body tensed as wave after wave of pleasure shot through me like lightning. I don't remember if that silencing spell was still active, but I didn't care. All my lust-crazed mind could focus on was riding that orgasm as far as I could take it.

Finally, Spitfire stood up, and I nearly collapsed into her hooves. "Oh... O-oh my, I, just... Wow."

Spitfire kissed me again and smiled. "I'd say you owe me one, Dash, but I think under the circumstances, I'm willing to give you a rain check."

We sat back against the wall and held each other after that. Little more was said, and at some point we must have drifted off to sleep, because the next thing I remember after sitting down with her was awaking to the sounds of somepony shouting.

The shouting was coming from the outside hallway, where the fat, snobbish guard was supposed to be. More shouting, then some banging sounds, and for a second, the small light coming from beneath the door turned a neon green. A moment later, the outer door was ripped right off its hinges as if it were nothing. The room filled with smoke and the distinct smell of spent magic, and despite the sudden lack of relatively clean air, instinct kicked in and we adopted defensive stances.

A figure emerged through the haze, and while I couldn't make out the face, the bright blue and gold of the Wonderbolts flight suit was unmistakable.

"Sorry, ladies," Soarin's voice called out, along with the jingle of a set of keys. "But we're checking out early."

I looked over to Spitfire, who returned my relieved smile with one of her own. "When we get back," I said with a wink, "I'm cashing in that rain check."

We got home safe and sound, much to everyone's relief, and I cashed in that rain check as soon as possible. That extra hundred bits bought the two of us a nice dinner too... To celebrate a successful rescue, of course.

Author's Note

Credit for this particular scenario goes to RatedPonystar, who originally presented this pairing to me in the form of a short writing challenge. I really liked the idea, and with his permission, I turned it into this latest edition of Red Shoes. I hope I've done the idea justice. ;)

For the next two chapters, there will be a bit of a twist on the usual format of Red Shoes. Specifically, the next couple of 'episodes' will be directly linked, and two characters will each take a turn revealing a particularly sultry series of events through their own eyes. Who's involved here? Well, don't ask me. Ask Lyra - she's up next.

Also, coming soon is our first guest chapter, courtesy of my good friend, Loyal!