Feminized for the Very First Time: 8 Books Feminization Anthology Read online

  I lifted it off the floor, surprised at how light it felt, wondering for a moment if perhaps it might be empty inside. But as I moved it up onto the bed, I felt something shifting inside, my curiosity increasing as I started to search for the way to open it. There was no lock to decipher, no code to crack – just two simple clasps that held it shut.

  Was I really about to do this?

  Was I really about to lift the lid of some mysterious suitcase?

  I paused, looking all around me, even though I was totally alone in the room, my breath held in my chest as I listened for any signs of life nearby.

  And only then, when I was totally sure I wouldn’t get caught, I reached out and popped open the clasps, and lifted the lid ...

  4

  At first, stupid as it sounds, I thought I was staring at a dead animal. Because all I could see was a mass of dark black curls. But of course, a second later, I realized it was a wig. A glossy, curly black wig. I tentatively reached out to touch it, registering with a surprise just how real it felt – so real it must have been made for genuine human hair, my fingers stroking through the mass of silky black curls for a moment, before I reached in and lifted it onto the bed, wanting to know what else this weird suitcase contained.

  The next thing that caught my eye was what looked like a silver makeup bag, and I lifted it out and unzipped it. Sure enough, it contained a whole bunch of makeup – mascara, eyeliner, lip gloss, nail polish and the like.

  Next to the makeup bag was a black card box, and I lifted the lid to reveal two oval lumps of what looked like pink jelly or silicone, each with a pert little nipple molded onto the top. Fake breasts, I guessed.

  There was only one other item in the case, lying at the bottom. Some piece of black, shiny clothing. With hands that were now shaking a little, I reached in and lifted it out, holding it up before me to inspect it. It was a black one-piece swimming costume, that at first just seemed like any regular women’s one.

  It was only as I started to inspect it closer, turning it inside out, that the truth became clear. Because it had fitted pockets in the bust, obviously where the fake breasts slotted in to keep them in place. And at the crotch area, there was some kind of formed, molded padding, that I assumed was some kind of attempt to hide your junk and make it look smooth.

  I dropped the costume back in the case, feeling a weird mixture of curiosity and disgust running through my veins.

  What the hell had the previous occupant of this room been getting up to in here?! I thought, quickly slamming the lid of the case closed and clicking the clasps back into place .

  Again, I considered taking the case to reception, maybe even complaining. But what if it looked like the case was mine, and I was some kind of pervert who’d come here on a crossdressing holiday and then had second thoughts? What if the girls caught me as I was handing it in? I’d never hear the end of it from Ashley.

  So instead, I decided to put it back where it belonged, stuffing it deep under my bed once more, pushing it firmly out of my mind as I set about doing what I’d initially intended and finally plugging my laptop in to charge.

  But as I climbed back onto the bed and set the episode playing, I found I couldn’t get the thoughts of that suitcase and its previous owner out of my head.

  They’d no doubt brought all that gear as a way of trying to sneak onto the women’s only beach, probably to creep on all the girls. But would that really work? Would they actually look real enough to pass it off?

  Probably not.

  If anything, they probably got laughed off immediately, their creepy plan going so badly they’d left all their weird, kinky shit behind in disgust at themselves.

  But what if it had worked? I found myself thinking a moment later. What if they had actually got onto the beach? All those cute sexy girls in their bikinis – some probably even topless or fully nude ...

  Before long, I’d started getting horny, the image of Ashley and her friends tugging off their skimpy little bikinis flashing through my head. Sure, she was a stupid little brat, but she had such a hot body. And so did Becky and Kelly, too. Man what I’d give to see them all naked, fooling around together.

  Again, I paused, listening to the silence of the hotel, checking I was alone, and when I was sure nobody was about to burst in on me, I pushed the laptop off my lap once again and started unbuckling my jeans and tugging open my boxers, freeing my already-hard cock, my mind dancing with images of Ashley, Kelly and Becky – their toned little butts and cute perky tits – as I stroked my dick, closing my eyes, feeling the first rushes of my orgasm already building up inside me.

  But as I stroked my dick harder and faster, some other thought entered my mind. Because now in my fantasy, I was there with them on the beach – dressed in that weird swimsuit, the long silky hair of the wig tumbling over my shoulders and the fake breasts pushing out from my chest, my cock snug and tight, my face done in full makeup and my legs smooth and hairless, as I lay on a towel, watching my bratty stepsister and her friends frolicking naked in the sand before me.

  And it was this final image that stayed fixed in my mind as I came, my orgasm hitting me way more powerfully than I’d expected. I quickly tugged my shirt up around my pecs, just before my cock spurted out a series of thick creamy jets, high up onto my abs, my whole body shivering and quaking.

  The whole thing had taken me by surprise a little. Normally when I jacked off, it was to the same boring old girl-girl porn I tended towards, the actual moment of orgasm kind of dull and something of a let down. But this? This had been way more intense, way quicker and hotter than normal.

  I lay there reeling on my bed afterwards, the gooey load starting to cool on my chest, the image of me dressed up like that amongst the girls still whirling around my head, and even thought I knew it was probably wrong, and even though I’d just cum and it should be out of my system now, I felt my mind lingering on it afterwards, starting to toy around with a strange new idea. An idea I just couldn’t shake free no matter how hard I tried ...

  5

  I heard the girls return to their room at about seven o clock, their laughter and chatter filling the hall and reverberating through to my room. I felt a pang of embarrassment at the thought that I’d masturbated over them, only a few hours earlier, and when I heard a knock on my door, I actually got a weird rush of nervousness.

  I jumped up off my bed, glad I’d showered and changed as I answered the door, where Ashley was standing, still dressed in her bikini top and hot shorts, the waistband of her bright pink thong, poking out just a little.

  “Hey Paul,” she said, her blue eyes dancing with a teasing glee, almost like she wanted me to blow up at her about the shitty trick she’d pulled on me earlier on at the beach, “we had a look at the food in the hotel but it looks kinda gross. So I think we’re gonna go and check out the town, maybe eat something there?”

  I didn’t know if she was inviting me along or just telling me, but before I could say another word, she made her intentions perfectly clear.

  “Don’t worry, we won’t stay out late.”

  “Just be back by midnight,” I sighed, knowing there was no use in arguing with her. “And no alcohol.”

  “Yes, dad,” she grinned back, turning and skipping back to her room, slamming the door behind her.

  The truth was, I didn’t particularly want to hang out with them tonight anyway. For a start, it would be boring as hell, hearing them chatter on all evening. And on top of that, I still felt kind of awkward, after my jack-off session earlier on. So I was glad to be rid of them, laying down on my bed and fooling around on my laptop, all the while waiting until I finally heard them come bundling out of their room again, their voices echoing off down the hall until once again I was left with silence.

  I knew I should probably eat something from the hotel buffet, but I didn’t feel hungry. All I felt was this strange, excited anticipation as – once I was totally sure the coast was clear – I crouched down and pulled out that black su
itcase from beneath the bed again.

  What the hell am I even doing? I thought to myself, as I lifted it onto the bed, unclasped the mechanisms and opened the lid, staring once more at its contents.

  It was almost I like I was moving outside of my own control, like I was watching myself in a dream, as I double checked that the door to my room was locked and there were no sounds in the corridors, before lifting out the wig, letting my fingers again graze through the long silky curls, so much darker and more lustrous than my own short, fuzzy blonde hair.

  I laid it carefully on the bed, my heart beginning to pound as I next took out the card box of jelly breasts and the swimsuit, my fingers shaking a little as I began to tug off my t-shirt, then unbuckle my pants and push them, along with my boxer shorts, down over my thighs, stepping out of them hurriedly and then pulling off my socks too, leaving me completely naked.

  That strange excitement built even further in my stomach as I once again took the swimsuit and tentatively stepped into it, feeling the elasticated leg holes sliding up around my slim thighs, and the tightness of the stretchy shiny fabric as it hugged my belly. It was almost breathtakingly tight as I inched it up even further around my waist, feeding my arms through the arm holes too, the snug fabric cupping my balls and cock so damn tightly as I pulled the shoulder straps into place.

  I reached in through one of the leg holes, adjusting my cock a little inside the small padded area where, to my surprise, it seemed to fit just perfectly, the contoured padding and tightness of the suit really tucking it down beneath me, holding it so firmly and snugly in place it was crazy.

  I gazed down at my body in awe, unable to believe what a transformation the suit had made. There even seemed to be a kind of corset-like design to it, the glossy black fabric scooping me in around the waist and underneath, yet giving the slight illusion of curves too, as it became looser around my hips and butt.

  I longed to see myself in the large bathroom mirror, but I wasn’t quite finished yet. With trembling hands, I took out the two jelly breasts and fed them one by one into the sewn in cups at the front of the suit, again marveling at just how perfectly they seemed to fit, the silicone quickly molding to my pecs and filling out the front of the suit in what looked – at least from my own perspective – like two small, pert and very real breasts, the little nipple bumps adding an extra hint of realism.

  I let my eager hands stray up my own body, feeling the smoothness of my waist and stomach, then further upwards, until I was cupping the soft lumps of my breasts in both hands.

  Holy shit. They felt just like the real thing, as real as any tits I’d ever groped through clothing, anyway. And I felt a sharp pang of horniness charge through me, my cock starting to swell between my legs. I gazed down, expecting to see a telltale bulge appear, but to my surprise, the suit kept me so damn snug down there, it still looked totally flat and smooth!

  And as I took a few steps over to where the wig was laying, I felt my brand new breasts actually jiggle a little, the soft weight at my chest bouncing, the way I imagined real tits must.

  I was enjoying this way more than I thought I would, like some excited kid on Christmas morning, each new piece I added to my brand new feminine alter ego making me feel less and less like boring, geeky Paul and more like someone totally new.

  Next I took the wig, turning it over to inspect the inside, seeing that there was a stretchy fabric cap that fitted over my head. I pushed back my short blonde hair with one hand, then stretched the wig over my skull with the other, feeling the long dark silky curls dancing against my bare shoulders, just like in my fantasy. And once I was sure that I’d tucked away every last strand of my own hair, I finally made my way to the bathroom.

  I held my breath as I stepped in front of the mirror, worried that I might be repulsed or just plain embarrassed by the sight that met me there. But instead, what I saw actually made me gasp out loud.

  Because I was startlingly convincing. I couldn’t quite believe what I was seeing, and stood for the longest time just checking out my own reflection, turning this way and that, marveling at how well the suit feminized my slim body, making my waist and tummy look trim and toned, while my butt actually looked pretty big! I’d never really paid any attention to my ass before, but now that it was in an outfit like this, I began to see it in a whole new light. It was round and firm, not crazy big, but certainly as nice as Ashley’s – the kind of ass I would totally find hot if I saw it in a thong bikini.

  And the wig looked so real, too, the dark curls tumbling down over my pale skinny shoulders, and framing my face. Even that kind of made more sense now. I knew I’d always looked a little androgynous, but now – with the suit, breasts and wig – I actually looked like a girl. I hadn’t even shaved, but my pale complexion and the blonde peach fuzz on my face and legs was only noticeable if you looked for it.

  I even started to have other crazy ideas – like taking my razor and shaving foam and actually shaving off my leg and underarm hair, as well as my face of course, to really complete the look.

  And I felt my mind straying too to that makeup bag, wondering if there were things inside it I could use to go even further – perhaps there was an eyebrow pencil, to shape and darken my blonde brows? And imagine if my lips were glossy and my eyes were rimmed with a little eyeliner or mascara, too ...

  But even as I was thinking all these things, another voice inside me was telling me that this was more than enough for now, that I’d had my fun and now I should just change out of this stupid outfit before I went totally crazy, or worse – that Ashley or one of the other girls might come back to their room for something and catch me.

  The thought of them seeing me like this sent an almost painful pang of embarrassment through me, and it was enough to make me quickly tug off the wig and step out of the swimsuit, going back through to the bedroom and throwing them hurriedly into the suitcase.

  What the hell had I been thinking? Was I going out of my mind? What I needed was a long, cold shower.

  Still naked, I walked back through to the bathroom and set the shower going, glad to be back to my old self once more. But even so, I couldn’t quite shake the thoughts I’d had, or the delicious feeling of being inside that suit, of how different I’d felt, almost like a whole new person.

  And as I stepped under the lukewarm shower and began to soap myself, I felt my gaze drifting around the bathroom until it landed on the disposable razor and can of shaving foam I’d unpacked by the washbasin ...

  6

  The sound of the girls returning to their room made me quickly slam the lid of my laptop shut; a reflex action, even though I knew that they couldn’t see what I’d just been looking at. I sat in bed, the thin sheets pulled up around my waist, listening to the murmur of their voices as they went into their room, slamming the door behind them, not a care for who they might wake up in the process.

  And only once I was positive that they weren’t gonna burst in on me, I tentatively opened the lid of my laptop again, the last website I’d been looking at flashing brightly onto the screen again.

  Eleven tips you need to know before wearing makeup to the beach, the headline of the article I’d just been reading pronounced. And on another tab in my browser was a YouTube video called How to Apply Makeup for Beginners.

  As I settled down a little further beneath the covers to carry on reading the beach makeup article, my now-shaven legs brushed together. It was such a strange feeling – to push my hand beneath the covers and trace my fingertips over my completely smooth skin, not a hint of the soft blonde fuzz that normally grew on my shins and thighs. I’d even shaved my ass and balls, leaving only a small neat rectangle of hair above my dick.

  Because tomorrow morning, I had a plan ...

  “Hey, Paul!”

  The voice came accompanied by a knocking on the door to my room, snapping me awake. Ashley, of course.

  “What?” I called back.

  It was kinda funny, I suppose. Just one day into our va
cation, and we’d managed to perfectly recreate the same dynamic we had whenever we were both at home – just shouting at each other through closed doors.

  “We’re going to that awesome beach again today. We’ll be back later.”

  At the mention of the beach, the last of my drowsiness evaporated and suddenly I was wide awake, my heart pounding as my devious plan once more flashed through my head.

  But could I really go through with it?

  “Okay, have fun,” I called back cheerily.

  I knew part of the reason Ashley wanted to go there was simply to piss me off, and I pictured her bratty face wrinkling up in annoyance at how cool and nonchalant I was being.

  “I think I’m just gonna hang out here at the resort,” I added.

  “Whatever,” I heard her mumble, before the slam of their door and the usual cackle of voices and laughter trailing off down the corridor told me that the coast was finally clear.

  My heart was beating like crazy as I realized that this was it. That I was actually about to start in on my plan – the plan I’d been cooking up all of last night. I knew I had everything I needed to see it through, all that was left was my own confidence.

  But first, a shower ...

  Keep your head held high, your shoulders back, your stomach tucked in and remember to swing your hips ...

  The voice of the instructor on the last YouTube video I watched, a tutorial on how to walk as a woman, was still buzzing around my head as stood by the door to my room, heart booming in my chest, every nerve in my body crackling with a mixture of anticipation and total fear.

  I couldn’t believe I was about to do this.

  What if it went wrong?

  What if I got laughed off the beach?

  What if Ashley and the girls saw through my disguise immediately?