Pretty Little Pony

by CrazyIvan

Rating: mature
Tags: My Little Pony: Friendship is Magic, Soarin, Romance, Sex, Shining Armor
Length: 3939

Shining Armor decides to take a chance on something his friend Soarin pushes on him during a one-night stand: Cross-dressing.

When Shining Armor bumps into Soarin during a visit to the local bar, he knew it was going to end in a one-night stand. What he didn't expect was that his friend would push him into something he never did before: cross-dressing.

Or, how he would come to love it.

Published 2013-08-12 14:30:02 UTC
Last updated 2013-08-12 14:30:02 UTC

Satin and Frills

My wife Cadance and I have what most would consider an incredibly open marriage, even by Equestria’s relaxed standards on sex. We both openly shared our bed with other ponies, stallions and mares, and apart from each other. We were both comfortable with the others bisexuality, and we both enjoyed taking time to share the memories of our experience with magic later.

Sometimes, having a wife whose special talent involves love in all its forms is a blessing.

After a rough week at the castle, I seized the chance to hook up with some random pony to relieve some stress, and share the experience with my wife when I got home. What I didn’t expect was to meet my long-time friend and former lover Soarin and have a few drinks with him.

It eventually got hot and heavy, as we made our way back to his room. Despite my advances, Soarin kept me at bay before we finally got to his room. Unlocking the door and walking in, he said he had a special present for me. But I wasn’t expecting this.

“Come on Shining!”

Here I was, standing before my old friend Soarin, staring at the mare lingerie placed on the bed.

“Oh please, it’s not the kinkiest thing we’ve ever done. Remember that one time when we lost that carrot?”

A blush sprung to my face, the memory of having to sneak out of my barracks and take Soarin to that emergency room unicorn doctor springing to mind.

“That was embarrassing enough Soarin, and it was bad enough Cadance found out about that.” I stomped my hoof, driving the point home. “She actually passed out from laughing the first time I shared that memory. She keeps bugging me to let her see it again!”

“Well, you shouldn’t have jammed it in so hard. It wasn’t fun for me either.”

“Says you, Mr. ‘It’s not enough’ ”

“Well, hindsight is 20/20.” A snigger escaped him before he continued. “Well, what about that time you and your guard buddies ran a train on me.” He ran a hoof against his flank, as he reminisced. “I swear, you all fucked me so hard, I could hardly walk, let alone fly for my exams the next day.”

“Hey, that was your idea. And besides, you did awesome on your exams, I mean come on; you’re on the team now.”

“Also, some of those guards still ask about you.”

“I’m flattered. Now put on the panties.”

“But-“

Soarin bit his lip, a sure sign he was going to hit me with his ultimate weapon. Oh sweet Aunt of my wife, he’s going to do it. I couldn’t look away; it was like watching an adorable train wreck. His lips began to quiver. His eyes began to widen. And then he gave me the big puppy dog eyed stare. But I shall not bend this time! I can resist, I can remain strong!

“No, I’m not going to Soarin.”

And then he whimpered.

My will was crushed immediately, annihilated by the adorable act. Throwing up my hooves, I sighed.

“Fine, fine, just stop looking at me like that!”

I reached over, scooping the items from the bed, before making my way to the bathroom.

“Ah! Hold it right there mister. You’re gonna need these!”

Reaching over he, opened a drawer, before pulling out what looked to be some make-up and perfume.

“Dammit Soarin, I-“

He started quivering his lip again, before letting out another whimper. Sighing in defeat, a spark of magic lit up my horn as I levitated the basket towards me and entered the bathroom.

Sitting down, I pulled everything apart and took stock of what I had. Frilly stockings for all of my legs, a pair of delicate, tight looking panties, a skirt that looked way too small and worse of all, a lacey little saddle, all made of some soft looking material colored a rich, deep purple. Letting loose another sigh, I levitated the panties towards me trying to fight my disbelief that Soarin had convinced me to do something I didn’t want to do once more. Looking at the panties, I tried calling to mind the times I’d seen Cadance put a pair on.

I stood up slipping my legs one at a time through the holes in the floating article of clothing before sliding them up to my flanks. Letting the magic go, I reached back with a hoof and began to slip them across my ass, a small gasp escaping my lips as the material engulfed my balls and shaft, pressing them close to my body. I stood there just savoring the feeling of the material on my body. It was one of the most sensual pieces of clothing I had ever worn, almost guiltily so.

A small thrill of excitement ran through me, as I lifted one of the stockings into the air. I couldn’t believe this, some part of me liked this, and I couldn’t help but wonder how far this would go. I quickly slipped two of the stocking onto my front legs, before lifting each of my back legs and gliding the article of clothing onto my back legs. I felt my member stir, as the soft cloth rubbed against my inner thighs. I lifted the skirt, hastily donning it and slipping it over my flanks and shaking my rump to settle it into place. One thing was obvious to me, and that was how awkwardly high this ran against my tail. There was literally nowhere for it to go but up, as it was hiked in the air to help accommodate the clothing to ride up against my rump.

I eagerly eyed the saddle as the realization of how much I wanted to complete the get-up filling me.

I floated the piece into the air, placing it onto my back, before moving my magic onto the straps and buckling it. After a few adjustments, I turned to the mirror, taking a look at myself. I couldn’t believe it. Everything fitted sensuously, to the point I actually looked like a mare. I turned around, swishing my tail out of the way and grabbing the edge of the skirt with my magic. I lifted it into the air and revealed my toned flanks, shaking them at myself in the mirror. The sight of seeing my taint and balls pressed firmly against the fabric was one of the most erotic things I had ever seen, as I throbbed almost painfully against my stomach.

Now, it was time for the final touch. I made my way over to the basket Soarin had given me, selecting a tube of lipstick that matched the color of the lingerie. I spun towards the mirror, swinging the tube towards my face and puckering my lips. I ran the make-up across my lips, coating them in the deep purple color. And then I realized that I had no idea what I was doing. After a few hasty wipes of a washcloth, I lifted the basket towards me and picked a bottle of perfume out and spritzing myself a few times.

Taking one last glance at myself, I made a kissing motion at myself, reveling in just how, well, sexy I looked.

I pushed open the door, making my way into the room. Soarin had made himself comfortable on the bed it seemed, as he gave me an amused look before slipping of the bed and moving towards me.

“I knew you’d like it. Satin suits you so well.” I felt myself blushing again as he circled around me.

“S-shut up.”

“Aw, how cute. You even smell pretty.” I felt his hoof slap my ass as he inhaled deeply near my mane, making me jump in the air slightly.

“Such a cute little slutty looking colt, all dressed up and ready to trot.” He ran his fetlocks against my thighs before moving them over my throbbing length, rubbing against my length, contained in its satiny confines.

“But what’s this? I sure hope you didn’t think you could please a mare with this tiny little thing! Why, it’s positively adorable!” The truth was that Soarin had always been bigger, yet he preferred to be the bottom. He always said he felt it was more intimate that way, and he liked looking up into my eyes. But something was different, he seemed more aggressive now, and there was a hungry look in his eyes.

“Soarin, what has-,“ He didn’t let me finish, slapping me on the ass again before placing his muzzle against my own.

“Ah, ah, ah! Sissy little sluts like you don’t get to argue.” I felt embarrassment rise in me, as he kept circling around and looking at me like a hunk of meat.

“Now, enough talking, my pretty little pony…” He shoved me from behind, making me stumble before falling onto the bed face first. I rolled onto my back as Soarin floated down onto the bed on top of me, diving in and pulling me in to a passionate kiss. He wrestled with my tongue aggressively, pushing deeper into the kiss and slipping into my throat occasionally. I felt myself surrendering, letting him roughly fondle my mouth as I felt his hoof slip down and pull my throbbing length from its confines.

Breaking apart, he slid down to my length, breathing on it gently.

“It’s so cute; I think I have the perfect thing to complete the look.”

He reached over to a night stand sliding open one of the drawers before pulling out a small pink bow tie on a loop. Moving back to my length, he grabbed it before slithering the girly decoration down to the middle of my cock, tightening it as my rod bobbed back and forth.

“Perfect…” A throaty grunt escaped his lips as he stood up, thrusting his length in my face.

“Now, prove how much of a little slut you are. Suck me off.” I felt myself moan, opening my mouth and pulling him into my mouth, sucking lightly and moving my tongue across the head. It was very apparent to me now how huge he was. I could hardly fit his length in my mouth, feeling myself watering at the musky taste of his cock, feeling him thrust occasionally as I sucked and tried taking more of his length into my mouth.

I slipped more and more into my mouth, stopping once I reached half way before beginning to sliding up and down the wetted length, pursing my lips tightly and running my tongue across the underside of his cock. I pulled the length out, staring at the glistening length, before wrapping my lips around the head, swirling across the tip, feeling the flare of his cock run across my palette as his salty pre-cum splashed into my mouth profusely.

After a short while of this, I felt his hooves grab the sides of my head as he grunted, thrusting hard and deep into my mouth, gagging me as the flat ridge of his head hit the back of my throat.

“Come on you little whore, take it all, I know you can.”

I felt myself squirming under his harsh words as my own member throbbed uselessly. I had never felt so humiliated in my life, and yet, it was making me hornier then I had felt in years.

He kept thrusting harder against the back of my throat before I swallowed, feeling his length slide into my throat. He let out a load moan and loosened his grip, letting his length settle in my throat before continuing.

Minutes later, he gripped my face again before fucking my face in earnest. His cock slid along the length of my thrust, his balls slapping against my chin and ramming my snout into crotch. Over and over again, I felt his length gag me, as the scent of his sweat and musk overwhelmed me, as his balls slapped against my chin over and over. His aggressiveness and harsh words made me feel like less of a stallion then I ever had, and I loved every moment of it. Moans escaped my throat as he pulled his cock out before slamming it back home, as I heard myself whimpering as the wet slapping noises filled the room.

I felt him speed up, before he finally pulled his cock loose of my throat, before locking eyes with me.

“Swallow. Every. Fucking. Drop.”

And he came, hard.

His cum flooded hot and creamy into my mouth, the salty flavor overwhelming as it rushed across my mouth. I swallowed as fast as I could, feeling the slimy, sour-tasting mixture slide down my throat. Every few seconds his length would throb again, filling my mouth as I swallowed greedily, trying to lap up as much as I could. After what was eight mouthfuls, I felt a final throb in my mouth as a small amount dribbled into my mouth as I swallowed almost instinctively. With a rough yank, I felt his cock leave my mouth, air rushing into my lungs as I gasped, before running my tongue across my mouth trying to gather what little was left in my mouth.

“Such an eager little fucktoy you are. I think you deserve a treat.”

I felt his hoof slide under me before flexing and spinning me onto my back as his hooves snaked down to my flanks and lifting them into the air. I felt my hips wagging in the air instinctively as I laid facedown, my face hot as I acted like some horny little filly in her first heat. I suddenly felt his moist breath against my thighs, feeling his hooves slide across the fabric of the skirt and panties, sliding them down and releasing my balls, and pushing my arced tail to the side as he moved closer to my taint.

“I bet you wash yourself back here every night don’t you? I bet you keep your ass ready for any real stud that comes along and wants to fuck.”

I felt my own cock throb harder, his words washing over me, shame washing over me at over the harsh words he spoke about the simple fact of keeping myself ready for any kind of liaison. With a sudden movement, he leaned in and ran his tongue across my flanks, making me shiver. He moved lower, slathering my balls before moving up, grabbing my flanks harder and running his tongue across the tight ring of muscles. He moved slowly in a circle, washing the spot with his warm saliva and hot breath. I felt myself squirming as he moved slowly, taking his time and gently working the area.

A gasp escaped my lips as he slid into me, my breath seizing in my chest as it slithered around, probing deep and hard into me. I felt air rush past my sensitive rump as he inhaled, his tongue working slowly, sliding around as if he was savoring the flavor of my ass. He began to speed up, his tongue lashing around inside me. I felt him push even deeper as his lips brushed against my ass, a knot forming in my chest as I felt him brush past my prostate. He nudged it gently several time forcing gasp out of my mouth each time. After what felt like an eternity, Soarin pushed gently against my flanks, pulling his tongue out. I felt him exhale on my flanks as he gave me a parting lick, before standing up and hunching over me.

“Your cute little hole even tastes sweet, just like a fucktoy should.”

I felt his cock rub against my ass, grinding hard against my hips as he hot-dogged it between my cheeks.

“Now, how bad do you want it?”

“P-please!”

“You’re going to have to beg for it you slut.” He leaned down to my ear, breathing heavily as he made his point, grinding harder against my asshole. “I want you to beg for it. Tell me you want the thick cock of a real stallion in you.”

“I-I-I want your big hard cock in me!”

“You really need to convince me.”

“I want you to fuck me, I want you to fill me up.”

“More.”

“Please, I want you to rut me like a horny mare, I want to moan like some filly in heat, I want you to fill me up over and over until my stomach swells with your thick cum. Please, fuck me until I can’t stand! I WANT YOU IN ME!” I caught my breath, shouting the last line as he slowly slid his length up and down my quivering backside.

“If you want it so badly, then I’ll make you my cocksleeve.” And then he pulled away from me.

I groaned as his weight lifted from me, feeling as if he had cheated me after working me up so much. A soft whooshing sound filled the air as he lifted off the bed, before landing on the floor with a distinct clicking noise. A short silence filled the air as I laid there with my ass in the air, groaning eternally at being left high and dry, my cock still hugged close to my stomach bobbing up and down with its cute little bow, and my tail twitching, hanging on the side of my flank.

Just as I began to give up hope, I heard the cap of a bottle snap open and something cold run down my cheeks, and dribbling down my balls. I felt my excitement rise as I felt the bed shift. Soon enough, Soarin’s hoof ran against my tender hole, spreading the lube around it, poking it inside and slathering it inside me. A sound of satisfaction came from Soarin as his hoof left me, and I heard the sound of more being squeezed out.

I felt his weight settle against me, his body pressing against mine as I felt his cock rub against my asshole in earnest. He leaned over me, his throbbing meat nuzzled gently against my opening and his legs to the side of my body. I could feel every ridge on his cock head as he laid it there.

And with a forceful push, the tip of his cock slipped into me.

I felt a shiver run through, feeling my insides spasm as the foreign object entered me. He moved slowly, pushing it in bit by bit, the lube letting him slip further and further in. A cry escaped my lips as he brushed past my prostate, the knot twisting tighter in my chest as I felt my own orgasm fast approaching, as my cock throbbed wildly underneath me.

Further and further he pushed, every inch working its way inside of me, stretching my hole open wide. I felt myself relaxing and the spasming stop as I started sucking him in instead, letting the feel of his thick cock fill me. Soon, I felt him stop; the ring of his cock pushed gently against my opening, and I could hear him breathing heavily as his damp breath hit the back of my neck. With a grunt, he thrusted sharply and placed the last of his length inside of me.

Feeling his balls slap against my ass, my body decided it was too much as the knot in my chest unwound, and I felt my own body and cock seize up, as an explosive orgasm rocked me. I felt own length throbbing, warm cum shot across me and landed on the front of my stomach over and over again, the thick mixture running down to my neck before pooling there. Eventually, my body began to loosen and my legs began shaking, the last bit of jizz dripping from my cock.

“You came already? I should have guessed a little bitch like you would cum after the first taste of cock from a real stallion.”

I couldn’t reply, trying to catch my breath as my senses, and the now familiar feeling of Soarin’s length throbbing in me returned. He made a dismissive noise as I felt his weight lift from my back, his hooves grabbing my flanks and squeezing them together, rubbing them slightly before he firmed his grip. My pulse skyrocketed, anticipation rising in my chest for what was to come.

Pulling against my flanks, I could feel his cock slipping out of me, every inch moving in me, before his ring popped out. A sharp grunt reached my ears, as I felt more pull out, before he slammed back home. A cry escaped my lips, but he gave me no time to recover, as his throbbing length left me again and slammed into me, over and over as he worked himself into a rhythm.

Again and again, his cock left me before slamming into me, as he fucked me harder. I savored the feeling, every inch, every throbbing vein pushing around inside of me as sharp slapping noises filled the room. I felt every thrust, as his balls slapped into my ass as his hips met my own. I inhaled the scent of his musk and sweat as it filled the room, the sound of his grunts as he took me like the slut I felt like.

I loved every minute of it, knowing it couldn’t last forever.

A short eternity later, I felt Soarin began to lose his pace; his thrusting become erratic and faster and his grip tighten as his body began to tense up. With a final push, his hips met mine against as I felt his cock throb harder in me. I felt my insides warming as his thick cum filled me, his balls tensing against my quivering asshole as he pumped more and more into me, stuffing me with more cum then I thought he had in him. Every spurt was a fresh wave of pleasure as my ass was filled. He began to pull out, spraying more into my bowels before the head of his cock pulled out with a light pop and a few weak burst sprayed across my ass and skirt.

I felt cum dripping down my backside as Soarin let go of my flanks, my legs giving out as I collapsed onto the bed and a mixture of our juices. I felt the bed move as Soarin lay down beside me, clearly as spent as I was, wrapping his legs around my body and pulling me close, his breathing heavy and uneven.

“So, Shining, was I right, or what?”

“Y-y-yeah.”

“Good. Keep the clothing. I want you to remember what it’s like to be fucked by a real stud.”

I didn’t respond, just lying there and feeling the warm cum slosh around inside me, basking in the afterglow of one of the best fucks of my life, and thinking to myself.

All I know is that Cadance is going to love this memory.

Author's Note

Well, if I haven't chased you away with the explicit porn of horses corn-holing each other while one cross-dressed, you might be wondering why this story is on hiatus.
Well, my dear reader, the answer is simple: Because I'm not done here.
This is but the first chapter in what I do believe at this point will be a three parter based around SA and Cadance feeding into his new found fetish.
Where will it go, what will happen?
I have an idea, but for now, I'm tapped out on writing for this.
If you liked this, stick around, next chapter will be about Cadance openly embracing her husband's new fetish.