Feminized for the Very First Time: 8 Books Feminization Anthology

by D. L. Savage

  “Uh huh,” I nodded shyly, my whole body poised in nervous tension now.

  I watched, enthralled, as his eyes filled with a new kind of lust, burning down at me as he growled, “Let me see it.”

  I felt a new jolt of excitement, his gaze burning into me as, still as dainty and feminine as before, I slowly uncrossed my legs, spreading them wide apart, then slowly inching my dress up my thighs until I’d uncovered the prominent bulge of my cock in my panties.

  “Show me, Amy,” he growled, his voice so low and taut, his cock so hard it looked like it might explode.

  With shaky fingers, I reached between my legs, tugging the panties to one side, my own dick finally bursting free – jutting up, rock solid between my thighs, the head slicked and soaking wet with pre-cum.

  And then something happened that I totally wasn’t expecting.

  Michael actually fell to his knees before me, his head moving into my lap as, sure enough, I felt his lips envelop my cock, sucking it greedily, his hands exploring my body as he did so, first my balls, then my thighs, them moving up to cup my breasts, as all the while he continued to suck and slurp at my dick!

  I groaned, arching my back, my eyes closing and my body suffusing with fresh pleasure. From the way he sucked me, I guessed that perhaps this wasn’t the first time he’d given head, but then I’d been a natural and I’d never done it before ...

  Either way, Michael seemed to know just what to do, and before long I could feel the pleasure swarming up inside me, and I knew that if he continued on for much longer, I’d be the one cumming in his mouth.

  “Stop, stop!” I gasped in a breathy little giggle, as he finally pulled his mouth away from my throbbing, aching cock, my balls now feeling so full and swollen I knew I was going to blow a huge load, whenever I did finally let go.

  We locked eyes, both of us totally overcome by pure animal lust now, and the words seemed to come from my lips all on their own, rising up from some deep slutty place inside me as I sighed, “Fuck me, Michael. Please.”

  In seconds, he’d shrugged off his clothes, while I too pulled off my dress and panties, but kept on my heels, stockings and bra. And then, as I watched Michael grab a package of condoms and fit one over his big, hard cock, I lay on the bed on my back, waiting for him to join me.

  A moment later he was on top of me, our cocks brushing together as we fused together in a hungry passionate kiss, my hands raking over the broad muscles of his back, again sensing she sheer size and power of him compared to my own skinny, slender frame.

  He was just as built as I’d been imagining, maybe even more so – his body bronzed and taut, lean yet muscular, too, no doubt from many long hours at the gym. I let my hands explore his chest, teasing his little nipples, cupping his pecs, then trailing down over his washboard abs, before again my eager fingers took hold of his cock, guiding it now to the place between my spread legs, to that tight little opening between my ass cheeks.

  If I’m telling the truth, this wouldn’t be the first time I’d had something up my butt. As a curious teen, I’d always enjoyed touching myself there, fingering my hole as I jacked off. And as I’d got older, I’d become even more curious, a couple of times even sneaking a vibrator from Amy’s room, lubing it up and fucking my own ass until I writhed and moaned on the bathroom floor.

  But this was totally different to some stupid plastic toy.

  I spat in my fingers and reached down, working my spit into the opening to my ass, then tenderly guiding Michael’s cock there, feeling the hot crown of his dick touching deliciously against my butthole.

  I let out a sigh of pure pleasure, my legs spreading wider, my eyes closing as – sure enough – I felt him slip a little way inside me.

  “Fuck, Amy,” he growled, “you’re so tight.”

  I could feel my butt stretching wider and wider, the more of that big dick he fed inside me, and I tried to relax all my muscles at once as, with a final breathy groan, I felt him slide all the way inside me, right to the hilt.

  We both paused for a moment, locked together like that, Michael’s dick throbbing deep in my ass, my own aching and rock hard between my spread legs, as we joined together in another hungry, sloppy kiss.

  And then, very slowly and tenderly, he began to fuck me, bucking his hips in such a sexy, slow motion that he had me gasping and writhing in seconds. I could hear the sounds I was making as he took my ass – the soft feminine moans that were spilling from my glossy lips – and they sounded so genuine, so real.

  Because they were real. In that moment, I wasn’t pretending any more. I was a woman, and this hot hunky stud was fucking me, his motions growing faster and more forceful as he began to take me, plundering my tight little hole with his thick, meaty dick, his full shaven balls slapping against my ass and his hands grabbing my thighs, holding them up in the air, so that I could see my own feminine, stockinged legs and heels as he fucked me.

  Pretty soon, I could feel my orgasm rising up inside me, even though I wasn’t even touching my cock. It felt like a whole different kind of orgasm to jacking off, too – more sensory, more of a full-body experience, whooshing around every single atom of my body, swarming and multiplying with each fresh thrust of Michael’s dick, until all of a sudden I gasped and moaned, tensing and stiffening, gazing down between my spread legs just in time to see my cock pulse out splash after splash of pure white cum, high up onto my tummy, flooding my stomach with warm liquid heat.

  “Oh fuck,” Michael gasped, as he watched me cum and felt the spasming of my ass as it clenched around his cock obviously sending him over the edge too. A moment later, with a final deep manly cry I felt his dick too begin to cum, jerking and pulsing deep inside me, his whole body shuddering, as the last flashes of my orgasm still fluttered through me.

  As we both collapsed onto the bed, flushed and sweaty, I let out a long contented sigh. Never had I felt happier or more content. Never had I felt more like me.

  “I guess you probably have to go soon,” he murmured, as we snuggled together on the bed a short while later, sipping our wine, which tasted so delicious, as if all my senses had been heightened by the amazing experience we’d just shared.

  “I don’t know,” I smiled back. “I guess I could stay a little longer ...”

  I felt my hand once more slipping between his legs, almost as if it had a mind of its own, a flash of excitement rushing through me as his hot meaty cock once again grew hard in my grip ...

  13

  “Oh shit!” I gasped, as my eyes flashed awake. “What time is it?”

  “Hngh?” Michael murmured sleepily, his gorgeous naked body slumbering next to mine, the hotel room now bathed in bright white morning light.

  My eyes darted to the clock on the wall and my stomach flipped over on itself in pure horror. It was almost nine o’clock already, and Amy’s presentation was at eleven. My head felt fuzzy from the wine and when I touched my hand to my face, I could feel the soft prickle of stubble, a sensation that now disgusted me.

  “Michael, Michael,” I murmured leaning over him. “I have to go ...”

  “Call me sometime,” he murmured back, still half asleep.

  “Oh don’t you worry, baby, I will!” I giggled, glad that he still felt the same way about me, now we were in the cold light of day.

  But I had no time to feel excited. I had to get ready.

  As I padded back to my room a short while later, still wearing last night’s panties, stockings and dress, my hair mussed up and my makeup no doubt smudged across my face, I could see why girls called it the walk of shame.

  Luckily, I only had to make it two floors down to my room and thank God, I didn’t bump into any other guests or staff on the way.

  Closing the door behind me with a sigh of relief, I quickly got undressed, then raced to the bathroom to shower and shave – my face and my legs. And as I did so, I ran through the presentation script in my head, as much as I was able, trying once again to call it to the forefront of my fuzzy, hung
-over brain.

  I just hoped to hell I didn’t make a total freaking mess of it ...

  A few hours later, I stepped out of the lobby of Inteltech, Inc, where I’d just spent the last forty five minutes sweating my way through the pitch.

  It was such a relief to step out onto the coolness of the sidewalk again, and I took a big refreshing gulp of air, feeling the wind ruffle my long blonde hair, hearing the click of my heels as I walked, my body now encased in much more sensible clothing that the slutty outfit I’d worn last night: silk blouse, pencil skirt, black tights, and a sporty thong.

  I came to a stop a little way from the building, pulling the cellphone from my purse and bringing up Amy’s number from my contacts, hitting call with a shaky finger.

  “So?” she practically screamed in my ear, the moment she answered the call. “I’ve been on edge all fucking morning. How’d it go?”

  She sounded so much better than the last time I’d spoken to her; her voice wasn’t hoarse anymore and she seemed back to her usual self.

  “Amy, I’m really sorry ...” I began, hearing the line fall silent as she hung on my every word.

  I left a long pause, before adding, “I’m really sorry to tell you that you got the contract!”

  I heard her scream on the other end of the line, so loud I had to hold the cell away from my ear until she’d calmed down again.

  “You bastard!” she laughed. “Don’t you ever do that to me again! So it really went okay?”

  “Of course it did,” I laughed back, deciding to omit the part where I’d fumbled and stammered at the beginning until, all of a sudden, the words we’d rehearsed came flooding back and the rest of it went off without a hitch, the CEO so impressed by the end that he offered me the contract on the spot. “You got the job, Amy. We did it!”

  “Thank you so much, Adam,” she gushed. “I know this must have been hard for you, I really do appreciate what you did for me.”

  In a moment of madness, I almost replied by saying, No, thank you. After all, I’d had one of the best experiences of my life.

  But instead, all I said was, “Don’t mention it. I actually kind of enjoyed myself in a weird way.”

  I could hear her chuckling on the other end of the line. But what she didn’t know yet – what I planned to tell her when I got home, in my own way, in my own time – was that this certainly wasn’t the last time I’d be dressing up like this.

  I finished the call, then strolled happily back towards the hotel, glad to be able to just enjoy myself now that the stress of the pitch meeting was well and truly over.

  And who knows?

  Maybe once I got back to Chicago, I’d give Michael another call, just like he’d asked me to.

  Yes, this really didn’t feel like I’d come to the end of my adventure at all.

  If anything, it felt more like I was right at the start of it.

  Virtually Allie

  Prologue

  I’d had a crush on my best friend Allie for as long as I could remember – ever since she moved into the big house at the end of my street, back when we were both just kids. Even back then, I’d thought she was awesome. She was a real tomboy, and we became fast friends, hanging out almost every day during the long summer break, and even going to the same school together in the Fall.

  As puberty hit, we couldn’t have changed in more different ways. I became a spotty, gawky, nervous teenage boy, while Allie blossomed into a beautiful young woman, the kind of girl every horny young guy would have a crush on.

  She never stopped being my friend though, even then, even though she was totally gorgeous. We had so much shared history, so much we still enjoyed doing together – she was just as into video games and sci-fi movies as me, perhaps even more so – and my secret crush just grew even bigger, the older we got and the more beautiful and wonderful Allie became.

  But did I ever tell her — tell her how I felt about her?

  Of course not! I was painfully secretive and shy back then, still am in fact, always second guessing myself, and deep down I just knew that it would fuck up our friendship, a thought which scared me more than anything in the world. Physically, she was totally out of my league; I knew that from the guys she dated during our teenage years – always going for the handsome, sporty guys who she had nothing in common with, always getting her heart broken when they turned out to be assholes, and always turning back to me when she needed shoulder to cry on.

  We stayed firm friends, right up until college, when it seemed like our paths began to diverge. Allie was always more science and technology focussed, and got accepted at Harvard where she majored in Computer Science, while I stayed on in our small town for a year, still deciding what to do with my life and my future.

  Pretty soon, one year turned into three, and it took me almost until my thirties to finally move out of my mom’s house, getting some boring-ass office job in the nearest big city, finally living on my own, renting a crummy apartment, occasionally catching up over the phone with Allie, and following her many adventures over Facebook.

  As we grew older, we did lose touch a little, but never completely. She always sent me a long chatty email on my birthday, called me up out of the blue once every few months, and last summer, she invited me to her wedding.

  I can still feel the strange swirl of emotions that ran through me that day as I sat there in the church, watching the love of my life get married to someone else – to some slick, banker called Greg, who was everything I was not: tall, handsome, successful. Allie looked as beautiful as always, dressed in a pure white wedding gown, and as the ceremony took place, I felt something die inside me a little; knowing it was finally time to let go of the fantasy I’d been clinging onto all these years, that one day the two of us would end up together somehow.

  It was a real wake up call, and when I went back home to my apartment in Chicago, I decided to make some serious life changes. For the first time in my adult life, I started exercising, going to a local gym every morning before work and all day at weekends, even taking up a better diet and skin care regime, slowly but surely watching myself transform into a halfway decent looking guy.

  Sure, I was no Greg – never would be – but now that I had put my crush on Allie to bed once and for all, I even found myself going out on a few Tinder dates, too, my confidence growing by the day. It felt like I’d missed out on so much, had so much life to catch up on, and I was really starting to get myself on track.

  But then one night, I got a phone call from Allie.

  A phone call that changed everything.

  1

  “Hey! I hope I’m not interrupting anything?”

  Her voice sounded strange on the phone, both excited and nervous at the same time, like she was about to drop some big news on me.

  “Only Game of Thrones,” I laughed, the latest episode paused on my laptop screen, as I lay on my bed, alone as always in my apartment. A typical Wednesday night in the life of Steven Michaels, in other words.

  “Good, because I’ve got something to ask you,” Allie said, cutting straight to the chase. “Something kind of ... strange.”

  Again, I wondered what was up. Normally, our phone conversations were much more relaxed – she’d always ask how I was, what I was up to, checking in on me like a big sister might, even though I usually had nothing much interesting to report. But tonight seemed different. Urgent.

  “Shoot,” I said, my curiosity growing now too.

  Something strange?

  “How easy would it be for you to take a week of work at, like, super short notice?” she said.

  “How short notice are we talking?” I replied, still puzzled what all this was about.

  “Uh, as in next week?” she said tentatively, her voice full of hope.

  I sighed. Things had been pretty shitty at work, even more so than usual. My boss Adam was a total prick, loading more and more things onto my already towering work load, and I knew there was no way in hell he’d let me just take the
next week off if I asked him. But this was Allie asking me, and as always, I could just never say no to her.

  “It’d be tough,” I began, then added after a pause, “but yeah, I think I could find some way of getting out of it. How come?”

  “Awesome!” Allie squealed, her excitement telling me that I was committed to this now, whatever the fuck it was. “I can pay for your flight and your accommodation and ...”

  “Woah, woah, wait,” I cut in, “what exactly is it we’re doing anyway?”

  “Oh, sorry, yeah,” she giggled. “I should probably explain that part. Well, apart from hanging out and catching up with you, we’d also be taking part in an experiment. Now don’t worry! It won’t hurt or anything like that. It’s just something my lab is developing. This VR thing, and you’re the perfect candidate.”

  “Me?” I asked, wondering what the hell was so special about someone like me. “How come?”

  “Well, actually it’s you and me,” Allie continued. “We’d be doing the experiment together. I need to work on this with someone I trust, someone I know really well. And of course, you were the first person that sprung to mind!”

  I smiled, flattered as always that Allie considered me such a close friend still. Sure, deep down, some part of me would always be in love with her, just a little, but I’d managed to reframe my feelings, and I was just glad we were still good friends after all this time.

  “You sure it’s not going to hurt or fuck up my head or anything?” I asked, but even as I was saying it, I knew for sure I was going. Not only would it be awesome to hang out with Allie again in person, I’d been super curious about VR – following all the latest tech developments online, even though I could never afford a home setup myself.

  “It’s going to be fine,” she laughed. “It should be pretty fun, actually!”

  “Great,” I said. “I’m looking forward to it!”