First Time Femme

by D. L. Savage

  Fuck, this was like an addiction.

  Once more I found myself gazing over at the cluttered dresser, chock full of all kinds of makeup, wondering what I might look like with lipstick, maybe a little eyeliner too …

  But my girly thoughts were shattered by a sound, a sound that made my stomach lurch in pure horror ...

  No fucking way. It couldn’t be …

  But it was. The soft thump of the door to the apartment and the muffled sound of Kelsey and Brandon’s voices, coming this way …

  With my heart booming in my ears, I quickly yanked off the bra and pulled off the panties, snatching my own clothes from the floor in a bundled heap as I raced butt naked out of Kelsey’s room.

  I’d just about made it to safety as they turned the corner in the hall, but I heard Kelsey whoop with laughter, no doubt at the sight of my lily white ass disappearing into my room.

  “Looking good, Nate!” she called after me and I heard Brandon let out a low chuckle, too.

  As I flopped down on my bed, the ice cold waves of relief washed over me as I realized what a close call that was and what a lucky escape I’d had.

  But at the same time, as my mind turned back toward the delicious feel of Kelsey’s panties and the sight of my pert ass in the mirror, I knew that something had truly awakened inside me: a hunger for more ...

  5

  After the crazy events of the weekend, my interest in lucid dreaming increased tenfold. After all, now that I’d had a taste of being a woman, I was desperate for more. But for some reason, no matter what I did, no matter how many damn reality checks I performed, I couldn’t wake up in my dreams again.

  And as I grew more and more hungry, I found myself reading about something else on the internet, too: crossdressing.

  Each night after I returned home from work I holed away in my room, searching online, lurking on forums, reading all about makeup techniques and padding and lingerie – all the many subtle, secret ways a guy could transform and feminize himself.

  And it was on one such night, as I was scrolling through Amazon looking at various wigs, that I heard a knock at my bedroom door. I quickly closed the browser before pushing myself up from my desk and heading over, opening my door to find Brandon standing there.

  I’d been avoiding him even more than usual, ever since I’d had that kinky dream about him. Kelsey, too - after all, I still felt pretty creepy about trying on her underwear. And as Brandon shot me a friendly smile, I felt my face flushing with heat as I remembered the feel of his big strong arms slipping around me, and his fingers toying expertly with my aching clit …

  “Hey man,” he said, “just thought I should let you know that Kels and I are gonna be away next weekend. She got us these super cheap last minute tickets to Fire Fest. We figured you wouldn’t wanna come, so ... yeah. You don’t mind looking after the fort without us, right?”

  “Hey, no, that’s totally cool,” I replied.

  Maybe a few weeks ago I might’ve been put out that they didn’t invite me, but now, the idea of having a whole weekend to myself – a weekend to explore my brand new feminine urges perhaps – seemed almost too good to be true.

  Already I could feel my brain starting to crackle with all kinds of new excited thoughts about how I could sneak into Kelsey’s room again, maybe try on some of her makeup, too ...

  “Just thought I should let you know, in case you were wondering where we’d gone,” Brandon added with a chuckle.

  “Yeah, thanks,” I replied. “Hope you have fun.”

  “Oh, we will,” he grinned, waggling his eyebrows suggestively.

  I closed the door and headed back to my computer, sitting down and reopening the browser, my head now spinning with excitement at the thought that I’d have a whole weekend to explore my newfound hobby.

  Spurred on, I clicked on my favorite wig – a long, glossy brown number – and added it to my basket ...

  * * *

  That night, I was woken by another knock at my door. I checked the time on my cell and it was a little after three in the morning.

  What the fuck? I thought. What could be so important as to wake me up in the middle of the night?

  It was only as I pushed myself out of bed, flipping back the covers to see that my legs were long and smooth, totally hairless, and that my vision was framed by long glossy auburn hair, that I realized.

  I must be dreaming again!

  As before, I felt things around me suddenly sharpen in clarity to the point where it really felt no different to real life. I could feel everything, every tiny sensation: the subtle weight of my breasts, the prickle of goose bumps on my skin, the cool night air, even the breath shivering past my plump lips ...

  I padded to the door, opening it, and once again there was Brandon. Only this time he didn’t speak, instead stepping forward and taking my chin in his hand, easing my face up to stare into his.

  I felt myself melting as he leant in to kiss me, pushing his sensuous lips against my own, a shiver running up and down my spine as I found myself enjoying the rough prickle of his stubble against my face, combined with feeling that I no longer need to be in control. There was something so fucking hot about giving myself up to him like that, of letting a big strong man take me in my arms …

  As his lips crushed against mine, I could feel my pussy throbbing as he pressed closer against me. I felt myself yielding, giving in to him, moaning into his mouth as his hand pushed once more between my legs. And this time, I slipped my hand between his thighs too, rubbing my fingertips over the hot hard bulk of his cock.

  Fuck … It felt so big …

  All I wanted in that moment was for Brandon to take me, to fuck me. And I let out a girly whimper of pure desire as I felt him roughly tugging my panties down around my thighs before easing his thick hard cock slow and deep into my aching wet pussy ...

  I woke again in the darkness, my heart pounding, my body shivering and my cock throbbing, right on the point of orgasm.

  But somehow, this time I could actually still hear the noise of Brandon and I fucking - his low manly grunts and my high girly sighs …

  Then it dawned on me. That wasn’t me making those breathy moans. That was Kelsey ...

  6

  “Alright, have fun you guys,” I said, as I helped carry the last of Kelsey and Brandon’s bags down to the waiting Uber.

  It seemed like they had a whole shit ton of stuff for just two nights at a festival, but I reminded myself that they’d probably want about five costume changes a piece. Also, from the weight of the bag in my hand and the suspicious clinking sound it made as I set it down on the driveway, it seemed as if they were taking a year’s supply of alcohol away with them too.

  “See you on the other side buddy,” Brandon replied, throwing me a peace sign.

  “Yeah, peace in the Middle East and we’ll see you on Monday night,” Kelsey grinned in her sexy husky drawl as the two of them both hauled the last of their stuff into the trunk of the cab then jumped inside, slamming the doors behind them.

  I waved them off, then headed back up the stairs to the apartment, feeling a tingling excitement of my own building inside me.

  I had the whole place to myself all weekend.

  It felt so exciting to finally have some time to myself, and once I was totally sure their cab had driven away, I quickly set about drawing all the curtains even though it was a bright sunny Saturday outside.

  Then I dashed through to my bedroom, kneeling down and reaching under my bed in order to retrieve the whole slew of packages that’d been arriving for me over the last few days from my online shopping spree – packages which I hadn’t even dared open until now.

  I felt like a kid on Christmas morning as I spread them out across the covers of my bed, looking at them eagerly.

  Then with shaky fingers I snatched up the first one, a soft grey plastic bag from a mail order company, tearing it open and reaching inside to slowly pull out its contents, my heart fluttering with excitement as I
set eyes on the silky black bra and matching skimpy g-string, which seemed so flimsy and tiny, so feminine, it was crazy. I could already feeling myself aching to try my new sexy lingerie on. But I didn’t want to hurry this.

  I set it down, before tearing open the next of the packages, this time slipping out another clear plastic bag within, containing the glossy chestnut wig from Amazon. I only hoped it looked (and felt) as good in real life as it did in my imagination.

  Next was a small paper envelope containing a pair of black hold-up stockings. The fabric felt so silky as I rubbed it between my thumb and forefinger and I couldn’t wait to try them on.

  The last package was from the mail order department of a drugstore. I tore it open and shook the contents out onto the sheets: a foundation in what I hoped was my pale white skin shade and a container of hair removal cream ...

  * * *

  I made sure not to hurry anything. I had all weekend after all. And I discovered that the longer I took, teasing out each stage on my journey to transformation, the more eager and excited I became.

  So after making sure to scrub myself thoroughly beneath the shower, I set about applying the hair removal cream, working it up into a thick lather all over my thighs, calves and belly. The bottle said not to apply it to any ‘intimate areas’ so I planned to shave those next (along with my face, of course).

  Once the cream had done it’s magic, I jumped back beneath the steaming shower to wash it off, and even though I didn’t have the hairiest legs to begin with, I was still pretty damn amazed by what a difference it made. Because seeing my legs like that, totally baby soft and smooth, I felt such a rush of girl excitement it took me by surprise. They suddenly looked so much longer, so much more shapely, and I found myself more eager than ever to try on the stockings.

  Next up was shaving. My face was easy enough, but I’d never really tried shaving my junk before, and it was kinda scary to be taking a blade so close to my nut sack, as well as my butt cheeks and under my arms. I just made sure to really take my time, reminding myself that I had all weekend and there really was no hurry.

  After what felt like an eternity of crouching and contorting my body as I scraped away at my most private areas with the razor, I was finally done, and after a last rinse under the shower for good measure, I began to pat down my body with a fresh towel, again amazed at what a difference being hairless made. It was so strange, but I actually felt like I wanted to move differently - like I was becoming more graceful and girly by the second.

  And while part of me wanted to wipe away the steam from the small mirror on the wall in the bathroom to check out the results of my handiwork, I resisted the urge, knowing it would be more fun to wait until I was all dressed up.

  I headed back to my bedroom, letting my hips swing playfully as I walked, my body wrapped in nothing more than a towel, excited to try on my very own lingerie and just hoping that the bra fitted me better than Kelsey’s (I’d bought it in a 32A).

  First I snatched up the panties from my bed, my stomach swarming with eager anticipation as I stepped into them, easing the delicate black waistband up over my hairless legs and into place, feeling the thin string slide so tightly between my ass cheeks while the soft black triangle of fabric tightly hugged my cock and balls, creating a smooth mound between my skinny pale legs.

  My hands were actually trembling a little as I took the matching bra from the bed, and this time, I remembered a trick I’d seen somewhere, maybe on TV – clasping it around my waist like a belt before I tried to inch it into place. To my relief, it seemed like I’d picked the right size as the clasp hooked just perfectly, and I found I was able to shimmy it up so that the cups sat tightly over my pecs. When I hitched the straps over my shoulders, I couldn’t help but grin. Because it felt so right it was crazy, and with the generous extra padding of the cups, it felt for all the world like I really did have a pair of small pert titties of my own!

  By now I was feeling kinda turned on and I could sense my cock starting to throb. But when I stared down between my thighs to check, to my relief I saw that even though the bulge had certainly grown a little, the tightness of the g-string was holding everything firmly in place.

  Spurred on, I snatched up the stockings, feeling a fresh shiver of girly excitement as I began to roll their delicate black fabric up and over the silky white smoothness of my legs, unable to believe how great they felt, the soft material hugging my calves and thighs so tightly it was surprisingly comforting.

  Once that was done, I picked up the final package with the wig inside. But before I actually put it on, I wanted to try something else first.

  It was time for a little makeover ...

  * * *

  “Now what you want to do is use the side part of the nib as you drag the eyeliner across your upper eyelid in a swooping motion, like so ...”

  As the YouTube tutorial chattered away from the speaker of my cellphone, the girl on screen made it look so damn easy. But when I tried the exact same thing, I wasn’t nearly as graceful, creating a much thicker and wonkier line than I’d planned, forcing me to go back to my first eyelid to try and balance out the effect.

  With a sigh of frustration I guessed I was done, glad that that part of the makeover was complete.

  I’d attempted my whole face, with varying levels of success, using all manner of Kelsey’s vast array of makeup in the process: everything from contouring and concealing, all the way through to striking vampish lipstick, lip liner and glittering over-the-top eye shadow.

  And now all that was left was the wig.

  My heart was in my throat as I finally shook it free from its package, brushing out the silky auburn locks, both super excited and also crazily nervous to see what it looked like on me. Because I knew that this moment was make or break – either lived out my girly fantasy IRL or else I just looked like some awkward dude in drag.

  Most of all, I wanted to feel it again – that sensation from my dreams of being girly and confident. Of being sexy. And as I slipped the wig carefully over my head, I held my breath, my fists balled in anticipation as I approached the long mirror in the corner of Kelsey’s room.

  But when I finally set eyes on myself, the breath from my lungs raced past in a startled, excited gasp. Because standing there before me was a real life girl! I honestly couldn’t believe it was even me. All the little mistakes I’d made with the makeup faded into insignificance now that I was taking in the bigger picture, and the wig especially really suited me, the brown curls creating such a colorful striking contrast to my pale skin.

  The craziest thing of all was that all the parts of me I’d hated back when I was a guy suddenly made sense now: my skinniness, my paleness, my lack of muscle definition, even my height (or lack of it).

  The effect was just insane, and I found myself posing this way and that, wanting to see myself from all angles, again blown away by how fucking good my body looked. Hell, I even had curves – my ass in particular looked amazing, so plump and pert, not to mention hot as hell with that sexy little wisp of a black g-string disappearing between my tender cheeks, and just looking at my own body over my shoulder got me turned on all over again, my cock starting to ache and swell in my panties despite myself.

  Now that I’d seen myself in underwear, I wanted to know what I looked like in one of Kelsey’s sexy club girl outfits. After all, there were tons of choices scattered all over the floor of her room, and without even having to take a step I’d managed to pluck a tiny black mini skirt and a similarly miniscule white tube top from the floor by my feet.

  I pulled the skirt on first. It was crazy how short it was, barely even covering my butt, hardly more than a flimsy band of black spandex. But holy shit, it looked good – at least in a super slutty way.

  Next I pulled on the tube top, which wasn’t much bigger, loving the way it hugged against the cups of my bra, the sheer tightness of it adding to the illusion that I had a pair of small pert breasts.

  Again I began posing, working m
y body this way and that, feeling so sexy and feminine, so carefree and fun – so unlike my boring old self as Nate.

  But just as I was casting my gaze around her messy room to pick out my next outfit, I heard a sound. A sound that I simply couldn’t believe I was hearing.

  No ...

  It couldn’t be ....

  But it was. To my total horror, I heard Kelsey’s voice calling out: “Hello? Anybody home?”

  It made no fucking sense. Hadn’t they just gone away for the whole damn weekend?! So why the fuck had they come back so soon?

  I looked around me for somewhere to hide. If this was a stupid movie, I’d have dashed into the closet. But Kelsey’s simply wasn’t empty enough to fit me inside. And from the sound of her footsteps, clomping this way down the hall, I knew I wouldn’t even have time to make a dash back to the safety of my room either.

  Sure enough, a moment later the door flew open and in she strode, stopping in her tracks as she caught sight of me, her big dark eyes widening and her mouth falling open in pure shock.

  “Woah, Nate,” she gasped. “Is that ... you?”

  7

  “Please, Kelsey,” I replied, so embarrassed I could barely speak, my voice trembling, “I can explain ...”

  “What’s to explain?” she shot back, her tanned face breaking into a strange smile. “You like dressing up. So what? Actually, I think that’s pretty fucking cool.”

  “Y-you do?” I stammered, unable to believe what I was hearing.

  “Yeah,” she replied, her grin widening. “I have to be honest, when you took out the room with us, I thought you were pretty dull. But if I’d known about all this …”