First Time Femme

by D. L. Savage

I nodded, stunned.

  “Well, before you go,” she added with a gentle smile, “you want me to help you with your makeup? No offence, sweetie, but it looks like you could use a helping hand ...”

  8

  “I’m not some crazy woman who always wanted a daughter, if that’s what you’re thinking,” Aunt Kate said as she carefully dragged the thin nib of the eyeliner pen around the edges of my eyelids. “I just always let Alex be himself ... or should I say herself.”

  She took a step back to assess her handiwork, nodding to herself, then moving on to some kind of pink powder in a pot which she began to brush against my cheeks.

  “I guess these days you’d call it gender fluid,” she continued, talking away happily as I sat there on the chair in her bedroom, my head still spinning about the fact that she was acting so damn cool about all this, “but back then, there wasn’t a word for it, other than crossdressing I suppose” she explained. “But to me, I just saw it as another expression of his personality. Sometimes Alex was a he, and sometimes a she. And who was I to get in the way of that ... You want lipstick too, honey?”

  I nodded shyly, watching on as she grabbed a stick of lipstick and pulled off the top, twisting the bottom as the bright red stick emerged from within.

  “Part your lips a little,” she explained, and I did as she asked, opening my mouth and holding as still as I could while she drew the stick across my lips, first the top one, then the bottom. “Now suck your finger, like so,” she added, placing her index finger into her mouth and closing her lips around it then drawing it out.

  I felt a little silly but I did as she suggested.

  “It’s to get rid of the excess,” she explained. “And that’s it, you’re all done. And my, don’t you look pretty! Why don’t you go take a look at yourself?”

  I felt my body prickling with nervous excitement as I pushed myself up off the chair, my black skirt swishing deliciously around my bare thighs as I padded towards the mirror in Kate’s room, my heart rushing with pure delight as I finally set eyes on my reflection.

  “Not bad if I do say so myself!” she chuckled as I stared in shocked amazement at the pretty girl staring back at me.

  It was so totally amazing what a little makeup could do – because now I looked truly feminine, my face just as girly as my body, my delicate features accentuated by Kate’s expert makeup skills, my face framed by my silky blonde hair.

  And dressed like this and made up to perfection, I no longer felt quite so terrified about the thought of making my appearance at Jody’s solstice party. Sure I was still nervous, the way anybody might be when going to a party alone, but I felt excited too …

  * * *

  As I weaved through the trees, following the soft sound of music and laughter, occasionally glimpsing flashes of the orange glow of a campfire, I felt more like I was in a dream than real life, and I was kinda relieved that the first time I actually went out dressed like this, it was dark.

  But as the memory of my own reflection flashed back into my head, I knew for sure that I was pretty too, which gave me the confidence I needed to continue down the path, willing myself not to chicken out and turn back.

  Finally I reached the clearing where the party was obviously in full swing, with a gathering of maybe twenty or thirty college-age kids, some girls, some guys, all of them with crazy face paints and outlandish clothes, holding beers, passing joints, dancing to the music that was pumping out of a nearby sound system. Some guys were made up pretty and wearing cute girly clothes, while others were going for a totally over-the-top drag kinda look. And I found myself standing at the edge of the clearing for a little while, hidden in the shadows, watching on.

  “You came ...”

  The familiar drawl of Jody’s voice broke me out of my trance and I turned to see that he’d come to join me. But as I stared back at him, at his flawless makeup, his long black hair, his big blue eyes and his slim body, encased in that tight black dress, I realized there was very little ‘he’ left in him at all.

  It got me thinking about what Aunt Kate had said, about how sometimes Alex was a he and sometimes a she, and that’s how I found myself thinking about Jody that night at the party – as a she.

  “Beer?” she said, holding out a can toward me.

  “Thanks,” I replied, my voice barely more than a whisper as I took it from her, my nervous fingers shaking a little as I cracked it then lifted it to my mouth, glad for some alcohol to hopefully take away my pounding nerves.

  “That’s a very pretty outfit,” Jody continued, looking me up and down, before adding, “Let me guess, it was Alex’s?”

  I felt my eyes widening. “So you knew about his ... uh ... I mean her secret?” I murmured.

  “C’mon,” Jody smiled taking my arm in hers. “The party can wait just a little while. Let’s go for a walk and I’ll tell you all about it ...”

  * * *

  “You know I had a thing with Alex,” Jody said as we made our way through the woods, the laughter and music from the party gently fading behind us.

  “You did?” I replied, a little taken aback by this new information.

  “Yeah, she was my first,” Jody laughed. “Alex taught me all about this lifestyle,” Jody said, pausing then adding, “How old are you now?”

  “Eighteen,” I admitted, hoping that didn’t make me sound too young or whatever.

  “That’s how old I was when I first met Alex,” Jody explained with gentle, wistful smile, before adding, “and she was the age that I am now. Huh, I guess what comes around goes around ...”

  “I guess so,” I muttered, realizing that we’d come to a standstill in another small clearing, the faint sound of the party still drifting over and blue slivers of moonlight shining down on us through the branches.

  For something to do with my hands, I lifted the beer to my lips, taking a noisy gulp, feeling Jody’s striking blue eyes watching me the whole time. And while I wasn’t totally sure, I was starting to get the vague feeling that maybe she was thinking about making a move on me, my whole body tingling with a strange nervous excitement – both dreading it and hoping for it all at once.

  “Hold still for a second,” she said just then.

  I froze in place, the beer can clutched tightly in my clammy palm, wondering if a bug had landed on me or something.

  “What is it?” I asked, my voice trembling a little.

  “You just look so pretty,” she smiled, her big blue eyes flashing, “I wanted to make sure I remembered this moment ...” She took a couple steps closer towards me, my senses filling with the deliciously sweet scent of her perfume as she added with a whisper, “the moment before I kiss you ...”

  I felt such a rush of intense excitement as she leant in it almost knocked the air from my lungs, my eyes closing and my lips parting as her mouth pressed against mine. There was no question that Jody was the one in control, pushing herself against me, taking the lead, one hand moving into my hair while the other slipped around my waist, pulling me tight against her as our lips crushed and our tongues flicked together.

  The kiss was so sensual it was crazy, nothing at all like the awkward fumbled encounters I’d had with girls back at high school. Nope, this was a whole different world – slow and delicious, with Jody taking full control of the situation, and soon I could feel my cock starting to throb and ache within the tight confines of my panties as I trembled in her arms.

  A moment later I moaned into her mouth, my stomach flashing with surprise as I actually felt her hand slip between my thighs, her long fingers cupping and stroking the hard bulge of my cock through the flimsy black fabric of my thong.

  Spurred on by how eager Jody was being, I decided to let my hands wander too, first slipping around her slim waist and then grabbing her round toned butt through the flimsy black fabric of her dress.

  She made a soft purring sound, obviously wanting even more and so I gingerly pushed one shaky hand down and between her legs from the front, my fingers slipp
ing under her dress. I’d never actually gone this far with anyone before, and my heart was thudding deafeningly as my fingertips grazed the unmistakable bulk of Jody’s cock.

  Of course that shouldn’t have been a surprise, but I’d gotten so used to her new feminine persona that it did kinda shock me a little. But I found my curiosity winning out as I gingerly began to stroke her dick through her panties, just like she was doing to me, both of us moaning and sighing now, our lips still locked together in a hungry kiss.

  Finally Jody broke away from me, her lipstick a little smudged and a mischievous glint in her blue eyes as she breathlessly murmured, “You want to go back to the party?” she whispered. “Or d’you want to maybe take this to my trailer?”

  I felt my stomach spike with nervous excitement.

  “I’d like to go to your trailer,” I replied in a shy whisper, my breath shivering past my lips, my heart slamming against my ribcage as she took hold of my hand in hers and began to lead me through the trees and into the darkness ...

  * * *

  “Well, here we are,” Jody drawled, “home sweet home. Sorry if it’s kinda a dump …”

  “It’s really nice,” I replied truthfully, my vision flitting around the small, neat interior of the trailer, which was lit only by a colorful string of fairy lights, my gaze finally resting on the built in bed, covered by white rumpled sheets, the fact slowly dawning on me that the bed would be the only place for us to sit.

  “Please, have a seat,” she said just then, sure enough nodding towards the bed.

  And as I perched nervously on the end of the mattress, my knees pressed tightly together, I felt it again: that strange dreamlike feeling. Because right now I was about as far away from my old life as I could possibly get.

  I watched on as Jody plucked a half smoked joint from an ashtray on a nearby counter and lit it, the flame of her lighter dancing for a moment, illuminating her pale beautiful face, before she sucked in then exhaled in a thick white plume of smoke, her eyes closing a satisfied smile. “You want some?” she asked a moment later, offering it to me.

  “Uh, sure,” I muttered, even though I’d never actually smoked a joint or even a cigarette before.

  My blood spiked in my veins as she walked toward me, taking a seat next to me on the bed, so close that our knees were practically touching, then handed me the joint and I lifted it to my lips, taking a small pull on it before immediately coughing and hacking my lungs out.

  “Let me guess,” she smiled, taking the joint from me then resting it back in the ashtray, “you never smoked before.”

  I shook my head shyly.

  “I wonder what else you haven't done,” she teased. How about this?” she purred, her fingers sliding beneath my dress and running up my thigh as I sat there frozen, my heart in my throat. “Have you done this before?”

  Again I shook my head, her fingertips now grazing right up the sensitive flesh of my inner thighs.

  “And how about this?”

  I gasped as her fingers touched my cock, stroking it through my panties.

  “Or this,” she continued, obviously enjoying her little game as she gracefully slid from the bed and positioned herself between my legs, her blue eyes staring back at me, a naughty grin etched on her pretty face as she slowly spread my legs then pushed my skirt up around my hips uncovering the hard bulge in my panties. “I bet you haven’t done this before,” she whispered teasingly, reaching out and tugging down the waistband of my panties, exposing my small hard cock and full tight balls.

  I watched on, frozen in place as she brought her head forward, her glossy lips parting and her eyes closing just moments before her mouth enveloped my cock with its warmth.

  I let out an involuntary gasp as she began to work her plump lips slowly and sensuously up and down my shaft, her tongue performing some kind of magic on the head of my dick, and before I knew it, I was gripping hold of the sheets, my muscles tensing and my teeth clenching, as I tried to fight back a fast-approaching orgasm.

  “W-wait ...” I gasped as I felt it rising up inside me, “stop ...”

  “Huh?” she said confused, pulling her mouth from my cock and staring up from between my legs in confusion.

  But it was too late. Despite myself, I felt the pleasure bursting inside me, and with a broken whimper I began to cum, a spurt of bright white cum splashing up from the swollen head of my cock.

  Jody’s eyes widened in surprise and quick as a flash she was back between my thighs, once again taking my cock into her mouth, her lips wrapping tight around my pulsing cock as she sucked up my load, making sure to keep her mouth around my cock until I’d totally finished cumming, swallowing my load with a soft gulp before pulling her face away, a satisfied smile on her sticky lips.

  “You taste really good,” she grinned, like this was all no big deal, “and you have a really pretty cock, too.”

  There was that word again – pretty – and I felt myself flushing with pride, my whole body still tingling and my heart hammering in a post-orgasm daze.

  “By the way,” she added, still in that same playful drawl, “I don’t expect anything in return, but if you did want to explore a little more ...”

  As she spoke, she pushed herself to her feet before me, slowly tugging up the hem of her dress, and I watched on from my seat on the edge of the bed, transfixed as she uncovered first her slim pale legs beneath and then a pair of black lace panties, through which I could make out what looked like a pretty huge cock.

  “... then this is all yours.”

  She jiggled her hips, the meaty bulge of her cock right there in front of my face.

  “Feel free to say hello to her if you want,” she added with a wry smile. “She doesn’t bite ...”

  I fought back my nerves and shyness, giving in to the curiosity that was burning inside me now as I reached out a shaky hand and began to gently stroke Jody’s cock first through her panties, then easing them down to fully expose it.

  As I’d suspected, it was way bigger than mine. It wasn’t even totally hard yet and it must have been six inches at least, maybe more, thick and pale with a glistening pink head and full round balls, her whole crotch shaved baby smooth.

  I began to jack her cock, feeling its thick warm weight in my palm as I stroked it, burning like fire against my skin, and then I leant forward, parting my lips, as I slowly took her cock into my mouth.

  I didn’t know what to expect, but it felt weirdly right, throbbing powerfully against my tongue, my lips closing tight around her shaft and as I began to work my mouth up and down her shaft, a flush of pride shuddering through me as I felt her grow even harder and bigger in my mouth, as Jodi let out a soft purr of pleasure, her hands moving into my hair and her hips starting to buck.

  Soon we’d settled into a rhythm, with me stroking her dick with one hand, cupping her balls with the other, and jacking her cock in time to the movements of my lips, my tongue occasionally swirling and lapping at her velvety smooth cock head, my mouth filling with the sweet musky tang of her pre-cum as she gently rocked her hips.

  “You like that?” she murmured. “You like sucking on that big hard dick?”

  “Uh huh,” I murmured, nodding, my voice muffled and my own cock rock hard again, straining at my panties.

  “You know where it would feel even better?” she added, her voice tight with lust. “In your tight little pussy ...”

  I felt a powerful pang of horniness as she said the word. The idea of my ass being a pussy turned me on in a way I couldn’t quite comprehend, but as she continued to talk dirty I found myself getting more and more lost in her words ...

  “Want to see if you can take this big hard dick in your pussy, baby?” she purred, and I found myself nodding again, pulling my mouth away from her glistening cock with a breathy gasp.

  “Good girl,” Jody grinned. “Just wait right there ...”

  I watched, trembling, still perched on the end of the bed, my cock tingling and throbbing, as Jodi pulled out a p
ackage of condoms, fitted one over her huge hard cock, then grabbed a bottle of lube and squirted a generous measure into her palm, before jacking it all up and down her sheathed cock.

  “Take off your panties,” she commanded a moment later, and I found myself more turned on than ever, loving the way she was taking control like this, doing just as she asked, pushing myself obediently to my feet then reaching beneath my skirt and easing down my thong, letting it fall around my ankles before stepping out of it.

  “Now come over here,” she said, as she took a seat on the edge of the bed, beckoning for me to straddle her.

  I climbed unsteadily over her and she quickly took hold of my ass beneath my skirt, guiding me down until I could feel the head of her cock touching against my butthole.

  “Just relax,” she whispered, leaning in and planting a tender kiss on my lips, her blue eyes piercing me as she spread my ass wider and eased me gently downward onto her.

  I let out a gasp as I felt the hot hardness of her cock press a little ways inside me.

  “That’s it baby,” she said, “good girl ...”

  And at her words it was like my ass opened up even more, as with a soft groan I felt myself sliding down onto her, taking her big hot cock deep into my butt until it was filling me completely, throbbing deep inside me.

  “Your pussy feels so fucking good,” Jody whispered, taking hold of my butt cheeks and rocking her hips, showing me what to do.

  Soon I’d taken over, grinding my hips back and forth, working my ass up and down her cock, feeling it throb deep inside me. And as our mouths met in another hungry kiss I began to ride her faster, amazed at how good, how right this felt, until soon I was bouncing up and down on her dick like a total slut, my arms thrown tight around her shoulders, girly little moans falling from my lips as I rode her for all I was worth.

  “That’s it baby,” Jody encouraged as I grew wilder and wilder. “Cum for me ...”

  I felt a fresh pang of pure horniness at her words, my rock hard cock throbbing beneath my skirt even though I wasn’t even touching it.