Crossdressing Stories - Your Girlfriend Dolls You Up For Halloween Party

Published on Oct 15, 2023 by Tohka Crow

Your Girlfriend Dolls You Up For Halloween Party

The Invitation

"Hey there, love. I still can't believe you agreed to go with me to Derek's Halloween party. You know how much it means to me, right?"

"Aww, I know these kind of events aren't your thing. That's why I love you even more for it."

The Costume Dilemma

"Have you thought about what you're going to dress up as? Maybe Superman? You definitely have the charm for it."

"Oh wait, I've got an even better idea! What about... a pretty, pretty princess?"

"No, seriously! Imagine how cute you'd look in a dress, with all those ruffles, lace, and maybe even a tiara on top?"

"Oh, come on! Don't give me that face. I bet you'd be the belle of the ball. And I promise, I'd be right there by your side, making sure no other prince or princess steals you away."

"You know, it's all in good fun. And besides, there’s something incredibly charming about a guy who's confident enough to step out of his comfort zone for a night."

"Think of it as our little secret. Just between you and me. A night where we let go and just have fun together."

"Alright, alright, I won't push it too much. But admit it, the thought made you smile a bit."

"I just love the idea of us both diving into the spirit of things, having fun, and maybe being someone else for a night."

"But you know, whatever you decide to wear, I’m sure you'll look amazing. And I'm just super happy you're coming with me, even just being you, is more than enough."

"But hey, whatever you decide, just remember I'm so grateful you're coming with me. You in any costume, or heck, even just being you, is more than enough."

"Was that the doorbell? Sounds like my package is here."

"I'll be right back, I've got to grab it."

"Here it is! I've been waiting for this. It's my costume for the party."

"You're going to laugh, but I ordered a bunny bodysuit. Yes, I'm going full bunny this Halloween! Can't wait to try it on."

"Oh, what's this? Hold on... They didn’t!"

A Twist of Fate

"They've sent two bunny bodysuits instead of one! Can you believe it?"

"Now, this has got to be fate, don't you think? Maybe it's the universe’s way of suggesting a couple's costume?"

"You know, as tempting as it might be to send it back, the thought of us both in matching outfits is just too good. Picture us hopping into Derek's party, turning heads left and right!"

"Come on, admit it. It would be a riot, and quite the statement. Plus, with me by your side, what's there to lose?"

"Don't you think it could be fun? Just this once, let's be those 'matchy-matchy' partners everyone talks about."

"Okay, so imagine this: You, in that bunny bodysuit, and wait for it... paired with some sleek fishnet stockings. Oh, the thought!"

"And we can't forget about the shoes. What about high heels? I know they might be a challenge, but think about how they'd accentuate your... curves."

"Speaking of which, this bodysuit is pretty snug, you know? It'll definitely highlight some features you might not even know you had."

"And the cherry on top? A cute little bunny tail and those adorable ears. Oh my gosh, you'd look irresistibly cute and maybe even a bit sassy!"

"You never know, love. This might just be your breakout fashion moment. Ready to hop into this adventure with me?"

"You know, now that I think about it, I might be making a huge mistake here. With you in that bodysuit, accentuated by those fishnets and heels, someone might just swoop in and try to steal my bunny away!"

"Imagine the stir you'd cause. All eyes on you, admiring every curve, every playful hop. Those ears? They might just be your secret weapon, making hearts skip beats."

"And that tail? It won't just be cute; it might be your most flirtatious asset. A little wiggle here, a little shake there, and who knows? Some handsome guy might just get completely enchanted."

"I'm starting to second guess this. Do I really want to risk showcasing you like that? You, in all your adorable, sassy glory?"

"But then again, the idea of us, side by side, as the most unforgettable pair at the party... It's tempting. So, the real question is: Are you ready to be the talk of the night, even if it means I'll have to keep a close eye on you all evening?"

"Okay, mister, enough of this back and forth. For once, I need you to fully dive into one of my playful ideas. You do love a challenge, right?"

"Look, we don’t have any wild plans tonight, and honestly? A pre-Halloween dress rehearsal sounds just like the fun we need."

The Transformation Begins

"But if we're doing this, let's do it right. First step? I need you to go and get rid of that rugged beard and all that body hair. Picture it: your smooth skin against the soft fabric of the bodysuit... It’s all about the details."

"While you're in there, transforming into my smooth and suave bunny man, I'll be here slipping into my own bunny getup. And just wait until you see how everything looks when it's all put together."

"And just imagine, the two of us, hopping around the house, being absolutely ridiculous and adorable at the same time. You might even find that you enjoy this more than you thought!"

"So, what do you say? Ready to embark on this journey with me? Go on, get to shaving! I'll be here, prepping our looks for the most epic evening in."

"Oh, and one more thing. If you think you're going to be the only showstopper in those fishnets, think again. I've got my own pair ready. We're going to be the cutest matching pair."

"And those heels I mentioned earlier? They might be a challenge, but I believe in you. They'll add that extra flair, making you look even more fabulous."

"But don't dawdle in there too long. The anticipation is honestly too much! I'm so excited to see you transformed, emerging with a mix of grace and cheeky confidence."

"After we're all dolled up, what about a mini photoshoot? Just us, capturing the fun. It'll be our little keepsake of the time we went all out."

"Alright, hurry up in there! I'm already getting into my costume. Can't wait to see you, Miss Bunny!"

Embracing the New Persona

"Wow, look at you! All smooth and fresh-faced. I hardly recognize this dapper person in front of me."

"It's funny how just a shave can make such a difference. You look... younger, more innocent. It's kind of adorable, honestly."

"Now, with that canvas prepped, imagine how stunning you're going to look in the bodysuit. The smooth fabric hugging all the right places. You'll practically be runway-ready."

"Oh, and those legs! Now that they're all smooth, the fishnets are going to pop even more. It's almost unfair how good you're going to look."

"But before you get too ahead of yourself, remember it's all in the details. The tail, the ears, the heels... Oh, the heels! I can't wait to see you trying to strut in them."

"Okay, time for the big reveal. Let's get you dressed and see the transformation. Prepare to be amazed at how fabulous you're about to look!"

"Oh, hold up! Before we dive into the costume, we've got another fun step first: makeup! Yes, you heard me right."

"Now, don't look so surprised. Makeup is the magic wand that's going to elevate the whole look. Trust me, a little eyeliner, some mascara, and maybe a touch of lipstick... you're going to see a whole new side of yourself."

"Have you ever felt the soft brush of a makeup brush against your skin? It's a treat, really. Relaxing, even. And just think about those eyes of yours, accentuated, making them pop."

"And don’t even get me started on the lips. A shade that complements the outfit, and suddenly, your pout becomes the centerpiece."

"Don't worry, I promise I won't go overboard. Just a touch here and there, to enhance that beautiful face of yours."

"Ready for your first makeup session? Let's bring out the inner diva, Miss Bunny, one brush stroke at a time."

"Alright, missy, let's embark on this delightful transformation. You might be squirming now, but just you wait."

"First, some foundation. We've got to cover up that rugged exterior of yours. Smooth, even, flawless - words I bet you never thought would describe you."

"Now, let's brighten up those tired-looking eyes with a bit of highlighter. Oh, what a difference that makes! It’s almost as if you had a full night's sleep for once."

"Contouring is next. Don’t worry, with a little magic, we’ll find those cheekbones. They've got to be hiding somewhere under there. And... there they are! Who knew?"

"A hint of blush to give you that just-embarrassed look. Oh wait, you're already blushing! Well, let's make it a tad more obvious, shall we?"

"Eyeliner time! I know, I know, this might feel strange, but those eyes of yours could use some drama. Bear with me. A little flick here, and a little there. Look at that, almost feline!"

"And now for my favorite part – false lashes. This will give those lashes of yours some much-needed volume and length. Bat those eyes for me. There you go! Fluttering like a damsel in distress."

"Finally, the crowning touch – lipstick. Let's find a shade that screams, 'I didn't choose this life, it chose me.' Pucker up, darling! That's a pout that's just begging for attention."

"Now, take a look. From rugged to ravishing. Quite the transformation, wouldn't you say? How does it feel to be the belle of the ball... or at least the living room?"

"Oh, just look at you! I can't believe that under all that gruff was such a... delicate flower waiting to bloom. Who would've thought?"

"Do a little twirl for me. Go on. It’s not every day I get to see you like this, all dolled up, lashes fluttering and lips all glossy. Makes me want to ask you out on a date!"

"Is it weird that I’m a bit envious? With those contoured cheeks and plump lips, you might just be outdoing me at my own game."

"You know, if I didn’t know any better, I’d think you’ve done this before. Look at that grace, that elegance! Has my rugged partner been hiding a secret femme side all along?"

"And those eyes! I swear, I could get lost in them. The way that liner brings out the spark, and those lashes? They're practically casting shadows! Are you sure you haven’t been sneaking into my makeup stash when I'm not around?"

"I almost feel bad for when we step out. People won’t know where to look - your beautifully made-up face, or the confused wonder on mine."

"But wait, our transformation journey isn't over. The final touch is still waiting – that bunny suit. I can't even begin to imagine the level of fabulous you'll hit once you slip into it."

The Reveal

"Ready to complete the look? I can hardly wait!"

"Alright, sweetie, before we get to the fun part, those drab male clothes of yours? Off they go. Honestly, with your petite frame, you never did them any justice. It's like you were swimming in a sea of fabric meant for someone twice your size. Kind of embarrassing, really."

"I've often thought, looking at you, that maybe, just maybe, you were born for something a little more... refined. Dresses, skirts, something that flatters rather than swallows you up."

"Now that you're free of that boring attire, let's introduce my little secret weapon. Ta-da! A petite corset."

"You've always had such a dainty build, not an ounce of macho bulk. This corset will only emphasize that, cinching in your waist and sculpting a truly delicate silhouette."

"Ready to be laced up? Oh, just the transformation I'm seeing already! It's like you're shedding that bland exterior and stepping into your true self. From 'barely noticeable' in those drab clothes to 'undeniably adorable' in a matter of moments."

"Just a bit tighter... Perfect! Look at that tiny waist. Who knew you had it in you? Or rather, who knew what was hiding under those ill-fitting male clothes?"

"Now, stand there and marvel for a moment. You're not the same person you were a few minutes ago, are you? Perhaps, underneath it all, you've always been destined for a skirt rather than slacks. Don't you think, Miss Delicate?"

"Oh, but we're not done yet, darling. The next little treat? These gorgeous fishnets. They’re not just stockings; they’re pure transformation magic."

"Stretch them out, slide your feet in. Feel the snug fit? They have this way of making legs look even more enticing. Those natural lines and curves of yours? They’re about to be ten times more noticeable."

"Work them up, slowly. It's like a caress, isn’t it? The gentle tug and pull of the netting against your skin. And as they reach your thighs, look at that contrast! The tight corset, the delicate fishnets... You're becoming a masterpiece of contrasts."

"And just look at those legs now! Long, sculpted, wrapped in that intricate web. The fishnets add that touch of allure, a hint of mischief. Never thought your legs could be a highlight, huh? Well, think again."

"Now, take a step. Feel how they move with you? Every stride you take, every little movement, just accentuated. You're not just dressing up; you're becoming art. How’s it feel to be wrapped in allure from waist to toe?"

"Alright, darling, now to address the elephant in the room... or should I say, the sad state of affairs on your head. But don't worry, I have the perfect remedy."

"Feast your eyes on this – a luxurious wig. Can you even remember the last time your hair looked this silky and voluminous? Oh wait, it never did!"

"Lean down; let’s fit this on you. There! Instantly better, don’t you think? Those dull strands you had? They’re history now. Replaced by cascading waves that, quite frankly, suit you better than I imagined."

"Give it a little toss. Feel how it dances around your shoulders? That’s the feeling of a full, beautiful mane. You know, the kind you've never had the privilege of sporting until now."

"I bet you never realized how much the right hair could elevate your entire look. It's like the drab guy who walked in here is disappearing strand by strand, replaced by someone far more captivating."

"Ah, seeing you now, it's becoming clear: beneath that unassuming exterior, there's always been a diva begging to be let out. And with every tweak and addition, she's getting bolder. Enjoying the transformation so far, darling?"

"Look at you! Almost there, but we're missing a crucial element, darling: the shoes. A good pair of heels can transform a walk into a sashay, a stand into a pose."

"Take a look at these beauties. High, but not too high. A challenge, but I think you're up for it, don't you think, Miss Soon-To-Be-Stunning?"

"Slide your feet in. Careful, careful. It’s like stepping into a new level of finesse. Feeling tall, are we? Elevated in more ways than one."

"Oh, don’t wobble; heels are all about confidence. Stand tall, push your chest out. There you go. Look at those calves, instantly more toned and tempting. It’s like you’ve been doing squats for years."

"And how does it feel, looking down and seeing not the flat, uninspiring shoes of everyday but these sleek, challenging heels? Like you’ve been dared to be extraordinary."

"Take a step. Another. Feel the sway? That's allure in motion, honey. Every step is a small seduction. Not so easy, is it? But oh, look at the reward."

"See yourself in the mirror. From head to toe, who is this enchanting creature? I barely recognize you. Are you ready to meet the world, and maybe yourself, for the first time, sweetie?"

"Aw, look at you in those heels, teetering just a bit. It’s such a shift from those clunky shoes you usually wear. Tell me, how does it feel to be elevated, quite literally, into the world of the feminine?"

"Take a few steps. Feel that? That’s not just the floor beneath those heels; it's a whole new perspective. Bet you never realized how much a simple pair of shoes could change the way you move, the way you feel."

"I must admit, there's a certain charm in watching you navigate this new terrain. It’s like watching a baby deer learn to walk – all shaky legs and unsure steps. But, my dear, with every step, you're evolving from clumsy to cute."

"Now, be honest, how does it feel to be a cute girl, even just for this moment? To feel the weight of those locks on your shoulders, the cinch of that corset, the height of those heels? A world away from the plainness you're used to, isn't it?"

"I know it might be overwhelming, maybe even a touch humiliating, realizing that all these little additions – the makeup, the wig, the corset, and now the heels – have turned you into quite the fetching young lady. Do you feel out of your depth, or is there a part of you that’s curious to explore this side even more?"

"Come on, Miss Adorable, share your feelings. Is it a mix of embarrassment and excitement? How does it feel to step into a world you’ve only observed from afar?"

"Now that you're all dolled up, it's only right we immortalize this moment. How about some selfies? Oh, come on, don't be shy now; you look too good to not have some photos."

"Here, take my phone. Or, wait, let's take it together. Arm up, angle it just right... Ah, there we go! Smile or pout – whatever feels right, Miss Photogenic."

"Oh, look at that shot! The light hitting your contoured cheeks, those lashes casting a shadow, and those lips – so kissable. Bet you never imagined you'd look this glamorous in a photo."

"Let's take a few more. Play with your hair a bit, give me a playful smirk. Oh, and let’s get one with those heels in view. Show off those legs! Who knew you had such model potential?"

"And one last one, a fun one. Make a silly face, let loose. This is all in good fun after all."

"Okay, let's scroll through these. Seriously, if I didn't know better, I'd think you do this regularly. Some of these shots are genuinely stunning. Feel proud, feel a bit bashful, but most of all, remember this playful adventure we've embarked on together."

"So, Miss Selfie Queen, should we keep these just for us or brave the world of social media? Your call!"

"Ooh, I have a daring idea! How about we get some feedback on your look? You know, to test the waters before the big night."

"Let's send a couple of these pictures to the Derek's Halloween party group chat. It'll be a fun teaser for everyone, and we can gauge their reactions."

"I personally think you look fabulous, but I'm curious to see what everyone else will say. Ready for a little sneak peek to our friends?"

"Alright, selecting the best ones... and sent! Now we wait. I bet in a minute the compliments will start pouring in."

Stepping Out

"Feeling a tad nervous? It's completely natural. But believe me, everyone's going to be stunned and they'll definitely appreciate the effort and creativity you've put into this. Prepare for the reactions!"

"Aww, look at that blush deepening on your rosy cheeks. Why so flustered? Afraid of what our friends might say? Or is it the sudden realization that you might just steal the show at Derek's party?"

"I mean, it's quite a journey you've been on today. From your everyday, nondescript self to this... alluring vision. It’s enough to make anyone a little self-conscious."

"Is it the thought of everyone seeing you like this? All glammed up, heels and all? Or maybe it's the idea that deep down, you're enjoying this transformation a bit more than you'd like to admit."

"Don't fret too much. Embrace the moment, embrace the blush. After all, it's not every day you get to experience life from such a different perspective. And who knows? Maybe our friends will be so impressed, they'll want makeovers next."

"But for now, enjoy the limelight, even if it's making you squirm a bit. After all, what's a little embarrassment in the name of fun and fashion?"

"Oh, here come the notifications! Let's see what our dear friends have to say, shall we?"

"Look at this! Sarah says, 'Who's this stunner? Can't be the same guy we know!' Ouch, seems like someone’s been outshined by their own glammed-up self."

"And here's one from Mike, 'Is that really you?! Almost didn't recognize without the usual drab attire!' Ha! Seems your previous fashion choices left quite the impression."

"Oh, and this one's golden. Derek says, 'Hope you’re bringing her to the party!' Seems like someone's intrigued! Who'd have thought your transformation would turn so many heads?"

"Jamie’s comment is hilarious, 'Always knew there was a diva hiding behind those bland shirts!' Well, the secret's out now!"

"Feeling a bit overwhelmed? It's okay. Deep breaths. It's a lot to take in. The attention, the teasing... But look on the bright side: you're the talk of the town, and for all the right reasons. Embrace the moment, even if it makes your cheeks turn a deeper shade of red. Everyone's just having a bit of fun, and honestly, they’re probably just a little jealous of how good you look!"

"Well, well, after all that excitement and fun, I can't help but think... Maybe this shouldn't be a one-time thing. The way you embraced the wig, heels, and all the attention? I'd say it suits you more than you'd care to admit."

"You know, with the way you've been rocking this look, I’m contemplating keeping you this way. Perhaps it's time to expand the wardrobe? I mean, Halloween will come and go, but we have the entire year ahead of us. Have you ever thought about a maid outfit? I bet you'd look absolutely precious bustling around in a little apron."

"I can already picture it. You, attending to the house, a feather duster in hand, all while teetering on those heels. Doesn't it paint quite the fetching picture?"

"But for now, let’s take a breather. How about we order in? Imagine answering the door like this. The delivery person’s face would be priceless! But don't worry, I won't make you do that... yet."

"Relax, take it all in stride. Today was just the beginning of our playful adventures. Who knows what tomorrow will bring? Maybe a package with a cute little maid outfit? Time will tell."