First Time Femme

by D. L. Savage

  I pushed myself to my feet and headed over to it, snatching it up to examine the contents. At first it looked like it contained nothing more than a sheet of rumpled pink tissue paper, but when I pulled that aside, and pushed my hand right to the bottom, I felt my fingers grab hold of something small and slinky that felt like nothing more than a tangle of straps.

  I pulled it out into the light, holding it up to examine it.

  Goddamn.

  It was a tiny purple g-string.

  Alice had always refused to wear g-strings and thongs for my benefit. She knew just how hot I found that kind of underwear, but the last time I could remember her wearing one to turn me on had again been on our wedding night, when she’d come parading into the suite in a skimpy white lace thong with matching bra and white stockings to boot.

  But ever since then, no matter how much I’d pleaded, she’d said the same thing: that those panties weren’t comfortable, and her days of wearing such slutty underwear were over.

  So why the hell she bought a g-string now?

  The answer was obvious, and I felt my cock throbbing even harder as I imagined her putting on this tiny pair of panties, not for my benefit of course, but in the hope that Bradley Stark might get a glimpse of them.

  Just then I heard a soft thump through the ceiling of the den. Our bedroom was situated directly above, and she was obviously starting in on her workout routine, wanting to get her body in perfect shape, wanting to tone her booty so that it would look perfect in those slutty panties ...

  With a sigh a frustrated sigh I switched off the TV then slumped back on the couch, knowing I had two options: either let her go to the concert and confirm my status as a cuck, or …

  I snatched up my cellphone from the coffee table, opening it up on the last message conversation I’d had with my sister.

  I’ve changed my mind, I typed. Let’s do this ...

  5

  “Have fun, honey, and I’ll probably be back pretty late so don’t wait up!” Alice gushed.

  It was early the following evening, and she was about to head over to Laura’s apartment in the city to get ready before they both went to the concert. I’d told her that I was just planning to have a little time to myself – kick back, drink a few beers, watch some TV – and as we said goodbye at the door, I again found myself wrestling with the urge to just straight out ask her about whether she was really planning to sleep with Bradley Stark and getting this whole thing out in the open.

  Even now, before she’d got fully ready and made up, with her new haircut, her tan, and her toned bod, she looked super hot, and it didn’t seem totally implausible that it might happen.

  But I’d been gnawing on this for so long, letting it grow and fester inside me into something so fucked up in my head that I couldn’t even put it into words without it sounding totally insane - a tangled up ball of anger and horniness and confusion all at once.

  So instead, all I said was, “You have fun too, honey,” reaching out and giving her a hug and a lame peck on the lips, before watching her as she raced excitedly down the driveway to the taxi cab waiting at the curb.

  I let the door swing closed, then just stood in the hallway, listening until I was sure that the taxi had pulled away and driven out of sight. Then, once I was sure, I pulled my cell from my pocket and requested a cab of my own ...

  * * *

  “I can't believe we’re actually doing this,” Clara giggled as she led me inside her apartment. And as I made my way into her cluttered living room, I saw that she’d already been hard at work, sourcing a whole shit ton of items for my ‘makeover’.

  She’d already asked for my sizes over messenger, and I'd felt like such a fool, hidden away in the bedroom while Alice had been working out in the den, wrapping a measuring tape around my chest in order to work out my bust size. She’d also asked for my waist, height, shoe size, the works.

  “Holy shit,” I said as I surveyed the things laid out – everything from high heels and dress to a wig, plus some sort of padding and a few other packaged up items. “Looks like you’ve really been to town.”

  “I know right!” Clara replied excitedly. “I took a trip to that crossdressing store – you know the one right near the entrance to Chinatown … Transitions? The girls in there really helped me out ...”

  “I can’t say I’m familiar with it,” I deadpanned, feeling a strange prickle of nerves at the idea of getting all dolled up in this weird, feminine stuff. “So how much do I owe you for all this?” I added. After all, I knew that Clara was a broke college kid and this must have set her back a pretty penny.

  “Oh it wasn’t too bad actually,” she replied nonchalantly. “All in all I think it came to ... maybe three hundred dollars?”

  “Three hundred?” I gasped. “That’s twice what I paid for the goddamn ticket.”

  “Oh come on, Mike,” she shot back, staying maddeningly calm. “You wanted to do this, right? So let’s do it properly. I don’t wanna send you out looking like some awkward dude in drag. I want this to be realistic.”

  “Alright, alright,” I sighed, catching a glimpse of the retro wall clock over her shoulder, my stomach flashing with nerves all over again as I realized it was only four hours until the concert began. “Let’s get this over with.”

  “Don’t talk like that,” Clara grinned. “I promise, it’s gonna be fun.”

  “Yeah, right,” I muttered beneath my breath.

  “Okay, so first things first,” she continued, ignoring my negative vibes, “you’re gonna need to shave.”

  “Huh?” I said, my hand shooting up to my face to double check. Sure enough my fingers brushed against my freshly smooth cheeks; I’d shaved less than an hour ago. What was she talking about?

  “I’m not talking about your face, dumbass,” she grinned, waggling her eyebrows.

  I felt my stomach sink, as I realized that my sister’s idea of ‘fun’ was very different to mine ...

  * * *

  “So how’re you feeling?” Clara asked as I emerged from her tiny en-suite bathroom a short while later, tail between my legs and a towel wrapped around my body, a body which I’d just shaved smooth from head to toe – an experience I definitely didn’t want to repeat in a hurry.

  “Sore,” I grumbled.

  “You used the moisturizing lotion after, right?” she asked.

  “Yeah,” I replied, “but it stung like hell. Oh and I got through about six of your crappy disposable razors, too.”

  “Stop complaining,” she laughed. “I’m sure it was all worth it! And from what I can see,” she added, nodding to my bare calves and the tops of my thighs that were peeking out from the hem of her threadbare towel, “it looks like you have a pretty good set of pins, Mike!”

  I was about to tell her to shut the hell up, but before the words could spring from my mouth I fought them back, biting my lip and sucking in a deep breath instead, reminding myself that she was doing this for me as a favor.

  “Alright, let’s just do it,” I sighed instead, reaching out for the tiny silver dress that she’d laid out in preparation on the bed – a dress that looked so damn small I swore my masculine body would split it in two.

  “Not so fast!” she called out before I could grab it. “Don’t forget about underwear. And before we even get to that you’re going to need to get acquainted with this little beauty ...”

  I watched on in a mixture of horror and fascination as Clara began rummaging around in one of the plain bags that must have come from that crossdressing store, pulling out something that looked for all the world like a skin-colored rubber g-string. But as she held it out to show me, I felt my stomach flip in pure shock as I realized what it was: a super realistic prosthetic pussy, complete with a plump shaved lips and even a little dark brown landing strip of hair, just like Alice’s bikini wax.

  “It’s actually pretty awesome,” Clara continued as I stared on in open-mouthed horror, flipping it around to show me the underside. “The girls at th
e store showed me how it worked – you just put your dick in this tube part, and then your balls fit under here, where the lips are. It keeps all your junk tucked tight against your body, and there’s even a small hole so you can pee out of it ...”

  She paused, clocking my horrified reaction.

  “Oh come on,” she sighed, rolling her brown eyes at me and blowing at her bangs. “What? You wanna just go strutting in there with a big ugly bulge swinging around in the front of your dress? This is going to make all the difference when it comes to realism. Trust me.”

  “Couldn’t you just have picked me on outfit that was a little ... looser?” I queried, my voice barely more than a croak.

  “I guess,” she shrugged, “but with a body like yours, I thought you’d wanna show it off! And all the other girls at the concert are gonna be wearing stuff like this. Now c’mon, try it on at least ... I promise I won’t look.”

  With that, she thrust the prosthetic pussy toward me. It looked so weird, dangling from her hand, and I pushed myself to my feet and snatched it roughly from her, shaking my head at the fucked up situation I found myself in.

  As I held it in my fingers, I realized that it was actually made out of some kind of silicone substance instead of regular rubber – it actually felt eerily real and spongy. And as strange as it might sound, a small fucked up part of me felt a teensy bit curious to see what it might feel like to wear, and whether it really would hide my junk like Clara had suggested ...

  “Alright, turn away and don’t look until I tell you,” I sighed.

  “That’s my girl!” she giggled, turning her back to me.

  I sucked in a final breath, then pulled open the towel, letting it drop to the floor at my feet. After fumbling a little with the pussy, I finally found the part Clara had mentioned, a small stretchy tube that I pushed my tiny flaccid dick into until it was buried right to the hilt inside.

  The pussy lips really did seem to have two hollowed out areas at the back too, which snugly fit my balls as I pulled the pussy tight around my under carriage by the thin clear string part at the back that slipped tight between my ass cheeks like a g-string.

  It seemed like the string at the back and the ones at each side all clasped together at the back somehow, but obviously I couldn’t quite work it out, and with a frustrated sigh I knew it was time to ask Clara to help.

  It seemed so fucked up to ask my own kid sister when I was practically buck naked, but I tried to remind myself that we’d see each other in the altogether many times before (alright it’d been when we were just tiny kids, bathing in the tub at our parent's house, but still) …

  “Hey, I might need some help over here,” I said through gritted teeth, willing her not to make some joke or other.

  But less than a second later I heard her let out a loud whoop of laughter and I felt my face flush beet red as she called out, “Oh my god, Mike, you actually have a really cute ass!”

  “Please just shut up and help me out,” I sighed.

  “Alright, alright,” she giggled, racing over and pulling the strings from my hands. “Now breathe in!” she laughed, and I let out a yelp of surprise as I felt her tug them way tighter than I was expecting, in what felt like the mother of all wedgies – smushing my dick and balls so damn snugly against my body that I wondered if it might be causing some kind of permanent damage.

  “Does it really have to be quite that tight?” I winced, eyes watering.

  “That’s what the girls at Transitions said,” Clara replied as she clipped the straps together. “There, all done. Now turn around and let me see ...”

  I swallowed back my embarrassment and turned to face her, both of us staring down at my crotch, which was now totally covered by that weirdly realistic synthetic skin. It was the strangest sensation, gazing down between my legs and no longer seeing my cock and balls – or even the fuzz of brown hair that grew on my thighs and calves – the whole thing eerily convincing.

  It seemed as if Clara felt the same way: “Holy shit,” she muttered, her eyes widening. “That thing is crazy good. How does it feel?”

  I thought about it, adjusting my weight a little from foot to foot. Sure it was snug, but actually, now that I’d got more acclimatized to it, it didn’t feel too painful anymore. “Alright, I guess,” I sighed.

  “That’s good enough for me,” she grinned. “And it’s going to make this look so much better!” she added, dashing back to the bed and picking a scrap of clothing from it, which I realized with a lurch of shock was a tiny black thong.

  “Seriously?” I asked.

  “I mean, yes,” she shot back, rolling her eyes. “Visible panty lines are a total no-no in a dress like that. C’mon, I bet it’ll make your ass look super hot, too!”

  I snatched the panties from her without a word, stepping into them and tugging them up around my waist. To be honest, what with the straps of the synthetic pussy already wedged tight between my ass crack, the thong made little difference. But when I stared down again at myself, I saw with an odd tingle of curiosity that the pussy really had done as intended – beneath the silky black fabric of the panties, the soft plump lips of the pussy really looked like cameltoe.

  I felt a fucked up part of myself even getting a little turned on, and what was worse was that the feeling grew stronger the more I tried to ignore it. Before I knew what was happening, I felt my cock growing hard and my balls tightening and I sucked in a breath, hoping to god my brand new boner didn’t send the whole contraption bursting open, which of course would have been doubly embarrassment in front of my goddamn kid sister.

  To my surprise and relief, the pussy held everything so damn tightly in place that it seemed to the outside eye at least that nothing had changed – no visible bulge in the panties or anything.

  Wow, I thought, realizing that in a way, this was actually pretty damn cool.

  What’s more, as odd as it may sound, I started to enjoy the thought that it was actually like a real pussy in that respect too. Because unless you actually checked to see if a girl was wet, there was no way from the outside of knowing if she was turned on ...

  “Hey, no time for dawdling,” Clara said, busting me out of my thoughts as she punched me on the arm and I snapped back to reality, hoping that my expression hadn’t somehow betrayed my fucked up thoughts. “We’ve got work to do …”

  6

  “I’ve changed my mind,” I protested about an hour or so later as I stood awkwardly in Clara’s living room.

  By now my face was caked in what felt like an inch thick of makeup, my head was covered by the tight itchy cap of the wig, and the tight silver dress clung to my body like a second skin, accentuating the curves of my fake tits (courtesy of the bra and breast forms that Clara had picked up from that crossdressing store) yet still leaving practically all of my legs on full display, while my feet were crammed painfully into a pair of matching silver heels.

  “I look fucking hideous,” I sighed. “There’s no chance I'll pass.”

  “You wanna know the honest truth?” Clara replied, reaching out and grabbing my shoulders, a surprisingly fierce expression on her face.

  I nodded, waiting for the worst.

  “You actually look pretty… good.”

  “Bullshit,” I hissed.

  “It's true,” she insisted. “But what you need to understand right now is that it’s all about attitude. If you go in there with your negative vibe, not believing in yourself, then of course they won’t believe you're really a chick. But if you go strutting into the concert with your head held, your hips swinging and your booty shaking then honest to God, I think you’ll get away with it. C’mon, follow me ...”

  With that she grabbed my hand and led me back through to the living room then gestured toward the couch.

  “Sit,” she commanded.

  I did as she suggested, easing my butt awkwardly down onto the couch, super aware of the tiny dress that threatened to ride up any moment to expose my panties, quickly crossing my long ha
irless legs, one over the other.

  “This is you currently ...” she said, as she began to do an impression of some awkward dude, lolloping back and forth across the room, shoulders hunched, head hung, feet plodding heavily.

  “Now watch,” she continued, suddenly becoming straight backed, hands on hips, head held high, her small breasts pushed out proudly as she began to strut up and down the room like a catwalk model before pausing, hand on hip to shoot me a cheesy grin. “See?”

  I nodded, but a moment later I let out a loud sigh, my shoulders falling even further. “Yeah, I get it,” I murmured, “but I still don’t think I can actually move like that myself.”

  “Of course you can,” she announced, racing over to me and grabbing my hands, pulling me so quickly back onto my heels that I almost toppled over in the process. “Back when you were in college? You were a pretty good dancer. You could imitate all the moves you saw on TV, right?”

  I nodded.

  “Well just think of this as dancing, Mike,” she grinned. “It’s just a series of moves to follow. So want to give it another try?”

  “Alright,” I smiled back, for the first time feeling a small flash of hope ...

  * * *

  Before I knew it, it was time to go. As Clara gave me a final hug goodbye at the door to her apartment, my head was swirling with all the brand new ‘moves’ she’d taught me in the last half hour or so. And her little pep talk had really worked: I found that by thinking of this whole thing as some sort of fucked up dance routine, I could pull it off ... just.

  “I owe you one,” I said as I gave her a final squeeze, my heart lurching as I caught sight of the cab waiting for me just outside her apartment block.

  “Ha, ha, don’t mention it,” Clara replied. “Now remember what I taught you: attitude.”