• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Jennifer Comes Out Pt. 01

Jennifer Comes Out Pt. 01

Alright, alright, so picture this: it ain't exactly sunshine and daisies outside my apartment, but that ain't stoppin' tonight's plans. Tonight, David takes a backseat, and Jennifer, well, Jen for short, takes the wheel. My nerves are shot, all jittery and excited like a chihuahua on espresso, but hey, gotta look fly first, right?

I crack open my makeup case -- this ain't your grandma's bargain bin stuff, this is the good life, all that fancy foundation and stuff that smells like rich people candles. First things first, gotta banish the ol' David redness. You know that splotchy situation you get after a shave?

Yeah, not cute. So, I slap on this green-toned primer, like, BAM! Bye-bye Rudolph nose. Next up, foundation. Think two shades darker than my natural skin tone, gotta get that J.Lo glow, you feel me? Dab it on with this damp sponge, gotta get that even coverage, y'know?

Now, those pesky little shadow monsters gotta go. I hit them with this peachy concealer, blend it outwards like a boss -- gotta soften those harsh jawline angles, David ain't exactly built like J.Lo either. My eyes, those hazel suckers with the green and gold flakes? They're gonna be Jen's moneymakers tonight. Brown eyeliner goes on first, lining my waterline, top and bottom, gotta smudge it out a bit for that smoky effect, you know, like I woke up like this, but better. Eyeshadow? Think warm brown, gotta follow the natural crease of my eye, then I blend that out like a champ with this fluffy brush. And for a little somethin' somethin', I pop some shimmery champagne color on the inner corners, gotta make those peepers pop, ya dig?

Lashes are next, can't have Jen lookin' like a tired bunny. Individual lashes, that's the name of the game, a mix of short and long ones, gotta fan out at the corners for that cat-eye drama. Top it all off with two coats of that black mascara, gotta make those natural lashes stand out, you know, gotta hold their own against the falsies.

Eyebrows? Those bad boys need some work. They're kinda thick naturally, so gotta tame them a bit. I use this brow pencil, a shade lighter than my hair, to shape that arch and tail, gotta fill in those sparse areas so they ain't lookin' all patchy. A clear brow gel keeps everything in place, gotta hold those hairs down, ain't nobody got time for a rogue eyebrow situation.

Now, here comes the fun part -- gotta sculpt this mug into Jen territory. I grab this contour stick, a couple shades darker than my foundation, and bam! I line my cheekbones, jawline, and even my nose bridge to make it look sharper. You know that highlighter stuff? Yeah, that goes right on top of my cheekbones, bridge of my nose, and cupid's bow. This play of light and shadow is what's gonna take David's strong features and turn them into Jen's delicate ones. Makeup magic, baby!

Last but not least, the lips. Jen's lips are her trademark, full and pouty, always lookin' like a juicy fruit snack. I line them with this deep berry lip liner, gotta overdraw them just a smidge for that extra oomph. The final touch? A generous slathering of this high-shine, deep berry gloss with a hint of gold shimmer. It's bold, borderline outrageous, but that's the whole point, right?

I stare back at my reflection, a smirk playing on my lips. David? See ya later. Jen's here to play. This makeup, it's like a shield and a spotlight, all rolled into one. It lets me disappear and get noticed at the same time. But under all this mascara and contour, there's a sliver of fear, you know? Fear of getting caught, fear of rejection, fear of this whole thing going sideways. But hey, the thrill of becoming Jen, the excitement of the night ahead? That drowns out all those worries. Tonight, Jen's in charge.

Alright, makeup on point, let's build Jen from the ground up. Comfort? Irrelevant tonight. Transformation is the name of the game.

First things first -- gotta wrangle the downstairs situation. Forget frills and lace, tonight demands a barely-there high-cut brief. It offers zero wiggle room, but that's the point. Every inch needs to be held firmly in place. Sexy? Absolutely. Comfortable? Not a chance, but hey, who needs comfort when you're aiming for bombshell status?

Next up, tucking. This ain't a walk in the park, but a little discomfort is a small price to pay for a flawless silhouette. I meticulously guide everything south for the time being, using a high-performance tucking gaff designed for maximum hold with minimal bulk. It pinches, it digs, but beauty is pain, right? Practice makes perfect, and tonight, perfection is the only option.

Now for some padding. I grab my secret weapon -- silicone breast forms, the D-cup wonders that feel disturbingly natural in my hands. Size is key, and I choose a pair that pushes the boundaries without looking fake. Positioning them just right takes some effort, but with the help of a special bra designed for forms, they become one with me. It feels unnatural, sure, but the end result is a breathtaking plunge that David wouldn't dare dream of. D-cup cleavage, on full display.

Shapewear is crucial for tonight's ultra-short, high-waisted miniskirt. Comfort? A distant memory. I squeeze into a high-compression bodysuit that feels like a second skin, sucking everything in and sculpting a figure that would make J.Lo jealous. It restricts my breathing, sure, but looking snatched is worth a little hyperventilation, right? This one comes with a built-in waist cincher -- a godsend tonight. It squeezes my midsection like a vice, guaranteeing an hourglass figure and posture so fierce I could probably pierce diamonds with my stare. Shallow breaths be damned, tonight I'm a statuesque goddess.

Here's a secret weapon -- double-sided fashion tape. Strategic application along the hem of the bodysuit keeps it from rolling up my thighs -- wardrobe malfunctions are a cardinal sin tonight. Every detail matters.

Lingerie? Forget practicality, tonight's about feeling like a million bucks. I reach for a demi-cup bra, a delicate wisp of mesh and lace that offers minimal coverage but maximum lift for the D-cup forms. The matching panty is just as skimpy, a cheeky cut that accentuates the curves the shapewear sculpted. It might offer zero support, but the way it caresses my new silhouette... pure confidence in a whisper of lace. Discomfort is a forgotten foe. As I slip into the lingerie, I can't help but admire the reflection staring back at me in the mirror. My body feels transformed, held in tight but undeniably sexy. It's a canvas, ready to be painted with the finishing touches.

With the foundation laid, a thrill shoots through me. This isn't David's body staring back -- it's Jen's. Every curve, every accentuated line -- it's all her. Now, for the rest of the outfit...

With the foundation laid -- my body a sculpted canvas -- it's time to paint the masterpiece that is Jen. Tonight, comfort is a distant memory replaced by the thrill of transformation. Let's get dressed.

First up, the top. I pull on the Soly Hux Women's Mesh Bodysuit. The black mesh material practically disappears against my skin, offering just a hint of coverage but clinging to every curve the shapewear molded. The long sleeves add a touch of sophistication, but the plunging sweetheart neckline dips low enough to showcase the impressive cleavage the D-cup forms created. It's a balancing act -- sophisticated seduction, and I'm here for it.

Next, the skirt. The Lunivop Women's Fashion PU Leather Pleated Skirt. The moment I take it out of the bag, a wave of nervous excitement washes over me. This bad boy is short. Like, ridiculously, provocatively short. It stops just at the top of my thighs, and the red screams "look at me!" It's a little too much, even for Jen, but in a way, that's the point. It screams confidence, a challenge, and a silent promise of what lies beneath.

As I slip it on, the soft faux leather caresses my legs, accenting the curves the shapewear sculpted. It hugs my hips perfectly, the A-line silhouette flaring out slightly at the hem. This might be a short skirt, but it's surprisingly flattering. Glancing in the mirror, a smirk plays on my lips. Maybe a little too much? Absolutely. But undeniably Jen? Absolutely.

Now for the nails. A quick coat of fire engine red -- to match the skirt, of course -- completes the look. Every detail matters.

The wig is next. I reach for my favorite, a long cascade of dark brown waves with subtle highlights that shimmer like spun gold in the light. It reaches down to my newly cinched waist, framing my face and adding a touch of glamour. As I secure it on my head, I can't help but admire my reflection. This isn't me, Jennifer, the girl next door. This is Jen, a vision of confidence and heat.

Accessories are the cherry on top. A chunky gold choker wraps around my neck, catching the light and jingling with every move. A pair of oversized gold hoop earrings dangle from my lobes, clinking softly against each other. They're loud, flashy, impossible to miss. But that's the point, right? To grab attention, to be seen. Nestled amongst the gold hangs a single, delicate pendant -- a tiny letter J. A subtle reminder, a secret whispered against my skin.

The shoes. The five-inch black stilettos. The moment I lay eyes on them this morning, a part of me knows they're a bad idea. They're gorgeous, all sleek lines and sky-high heels, but walking in Oaxaca's cobblestone streets with these things is a recipe for disaster. But then again, looking like a million bucks often comes with a price, and tonight, that price is a potential ankle sprain.

Being an experienced player in this game, though, has its perks. I can handle the pain, the wobble, the inevitable death grip I'll have on my clutch bag for dear life. Because that clutch bag? It's the Gucci GG Black Marmont Small Shoulder Bag. Pure luxury, and the perfect finishing touch to this carefully curated look.

Stepping into the heels, I wobble for a moment, the balls of my feet screaming in protest. But a deep breath and a quick mental transformation -- gazelle, not baby giraffe -- and I find my balance. It's a performance, every step a calculated sway that accentuates the curves of the skirt and the confidence I desperately want to exude.

As I walk out the door, I can practically feel eyes on me. The men stare, a mix of admiration and something more primal in their gazes. Women eye me with a mix of curiosity and judgment. I hold my head high, a predator disguised in a seductive disguise. They might see a slut, an expensive one at that, but that's just the mask. Beneath the red leather and gold jewelry, Jen, the predator, waits for the right moment to strike.

With the foundation laid -- my body a sculpted canvas -- it's finally happening. Tonight, I get to unleash Jen on the world. Comfort? A distant memory compared to the thrill of transformation. Let's get dressed.

First things first, the top. I pull on the Soly Hux Women's Mesh Bodysuit. The black mesh practically disappears against my mixed-race skin, offering just a hint of coverage but clinging to every curve the shapewear molded. The long sleeves add a touch of sophistication, but the plunging sweetheart neckline dips low enough to showcase the impressive cleavage the D-cup forms created. It's a balancing act -- sophisticated seduction, and I'm here for it.

Next, the skirt. The Lunivop Women's Fashion PU Leather Pleated Skirt. The moment I lift it out of the bag, a wave of nervous excitement washes over me. This number is audacious. Like, ridiculously, provocatively short. It stops just at the top of my thighs, and the fire engine red screams "look at me!" It's a little out there, even for Jen, but in a way, that's the point. It screams confidence, a challenge, and a silent promise of what lies beneath.

As I slip it on, the soft faux leather caresses my legs, accenting the curves the shapewear sculpted. It hugs my hips perfectly, the A-line silhouette flaring out slightly at the hem. This might be a short skirt, but it's surprisingly flattering. Glancing in the mirror, a smirk plays on my lips. Maybe a little daring? Absolutely. But undeniably Jen? Absolutely.

Now for the nails. To perfectly complement the fire engine red of the skirt, I reach for a shade called "Crimson Flame." It's a bold, high-gloss red that practically pops against my skin. I go for a medium length, somewhere around a quarter of an inch past the fingertip. It's long enough to be noticeable but short enough to be practical -- especially for a night of navigating Chicago's streets. Every detail matters, and tonight, that includes nails that are both fierce and functional.

The wig is next. I grab my favorite, a long cascade of dark brown waves with subtle highlights that shimmer like spun gold in the light. It reaches down to my newly cinched waist, framing my face and adding a touch of glamour. As I secure it on my head, I can't help but admire my reflection. This isn't me, Jennifer, the girl next door. This is Jen, a vision of confidence and heat.

Accessories are the cherry on top. A chunky gold choker wraps around my neck, catching the light and jingling with every move. A pair of oversized gold hoop earrings dangle from my lobes, clinking softly against each other. They're loud, flashy, impossible to miss. But that's the point, right? To grab attention, to be seen. Nestled amongst the gold hangs a single, delicate pendant -- a tiny letter J. A subtle reminder, a secret whispered against my skin.

The shoes. The five-inch black stilettos. The moment I laid eyes on them this morning, a part of me knows they're a gamble. They're gorgeous, all sleek lines and sky-high heels, but navigating Chicago's bustling streets with these things is uncharted territory. Weeks of practicing on my apartment floor -- much to the amusement, or maybe annoyance, of the downstairs neighbors -- have helped, but this is the real deal. But then again, looking like a million bucks often comes with a price, and tonight, that price might be a few wobbly steps and a death grip on my clutch bag. Because that clutch bag? It's the Gucci GG Black Marmont Small Shoulder Bag. Pure luxury, and the perfect finishing touch to this carefully curated look.

Stepping into the heels, I wobble for a moment, the balls of my feet threatening to mutiny. But a deep breath and a quick mental transformation -- gazelle, not baby giraffe -- and I find my balance. It's a performance, every step a calculated sway that accentuates the curves of the skirt and the confidence I desperately want to exude.

Okay, maybe a few practice laps around the apartment first. Just to be sure. I don't want to meet my demise on the first step out the door. Tonight is about Jen, the predator, not Jen, the human pretzel on stilettos. A quick strut around the living room, wobbling slightly but not falling -- progress! With a final check in the mirror, I take a deep breath and head for the door. The world awaits, and Jen is ready to conquer it, one perfectly balanced step at a time.

  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Jennifer Comes Out Pt. 01

All contents © Copyright 1996-2024. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+1f1b862.6126173⁩

We are testing a new version of this page. It was made in 56 milliseconds