Feminized for the Very First Time: 8 Books Feminization Anthology

by D. L. Savage

  There between her legs was a strap on dildo – pearly pink, totally realistic, with big full balls and a darker pink bulbous head. It even bobbed a little, just like a real cock would, as she strode towards me, coming to a stop right next to me on the bed, so the dildo was up near my a face.

  “So, what do you think?” she said, gazing down at me. “You like it? I thought tonight I could take your virginity.”

  I felt heart start to boom, gazing at that huge cock before me, wondering if I could really fit something so big inside my ass. I mean sure, Jenny’s fingers and tongue had felt amazing, but this was on a whole different level.

  “You really think it’ll fit?” I murmured shyly, feeling so totally feminine and submissive, already knowing that I was at least going to try and take it all, a naughty shiver of excitement running through me at the thought.

  “Why don’t you try fitting your pretty lips around it first as a test run?” she replied, pushing it closer to my face.

  It was so crazy. I’d never had any gay or bisexual thoughts before in my life, but right now, staring at that cock, I did want to try sucking on it, and again I found myself just giving in to her, doing whatever she asked of me. She was in charge, and I was her submissive little slut.

  So I took the cock in my hand, wrapping my fingers timidly around it as I guided it towards my mouth, first stretching out my tongue and giving it a tentative little lick before finally taking it right between my lips, feeling it fill up my mouth completely.

  Jenny actually groaned as I began to suck on it. I don’t know if she was just acting, getting carried away in playing the part of the guy, or maybe she actually felt some charge of desire, just from how damn kinky this brand new game of ours was.

  For my own part, I was getting more and more turned on by the second, making soft little moans and sighs of my own, the same way Jenny sometimes made when she sucked my dick, as I tried to take it as deep as I could into my mouth, working my lips eagerly up and down the hard shaft, my own cock how rock hard and straining at the tight snug confines of my thong.

  “That’s it baby,” Jenny growled, “take it nice and deep.”

  I felt her hands move to my head, holding it in place as she actually began to fuck my mouth, and I let out a series of muffled moans as she plundered my lips and throat with her cock before pulling it out, leaving me gasping and shuddering on the bed, feeling like a total fucking slut, my panties already starting to soak through with the pre-cum that was pulsing from my cock.

  I watched, my whole body trembling in anticipation, as Jenny moved over to a side table, grabbing a bottle of lube and squirting some onto her glistening cock, pumping it in her fist as she slicked it up and down. Then she climbed onto the bed, positioning herself over me.

  She reached between my legs and tugged my thong over to one side of my ass cheeks, then reached down and started working some of the excess lube into my hole, already sending delicious waves of pleasure through me just from that slight touch.

  “Are you ready, baby?” she said quietly.

  I nodded, my eyes locked onto hers, my body poised, watching as she guided the head of her cock right between my cheeks.

  I felt it press against my hole and for a moment, I worried that it wouldn’t even go in – that it was just too big. But I took a few deep breaths, and tried to relax all the muscles in my body, and all of a sudden it happened. I felt my ass yielding for her, spreading wide and open as Jenny slid the first thick inch inside me, a long low moan spilling from my lips.

  “I can’t wait to see you cum on this big dick,” she teased, her voice tight with lust, as she slid another inch inside me, another sharp thrill rocketing around my body.

  I groaned again as she fed even more of that big hard cock deep into my ass, until I felt like it might split me right in two. It felt so fucking deep, filling me completely, and just at the point where my pleasure seemed to tip over into pain, I felt her sliding out again, then back in, slam, causing a fresh wave of intense, white hot ecstasy to flash around my body.

  “Jesus,” I gasped, as Jenny began to fuck my ass, not taking any mercy on me whatsoever, pumping her hips fast and rough as she thrust her big glistening cock in and out of my tight little hole, each motion creating yet more delicious waves of pleasure to rise up inside my trembling body, until I was totally lost in the sensation, sighing and writhing and moaning beneath her, only faintly aware that she was sighing and moaning too.

  Again, I didn’t know whether she was just acting, or whether she was getting some kind of kick out of it, too – either mental, or maybe physical, from the way the harness was grinding against her pussy. But either way, she seemed to be enjoying herself just as much as me as she took my ass, hard and fast, until I started to feel that rising bubbling sensation of an orgasm fast approaching.

  “Oh shit, oh fuck,” I gasped, my eyes opening as I gazed down at my cock, which was jutting out from the top of my pretty white thong now, already leaking pools of pre-cum onto my taut belly as Jenny continued to fuck me, rock hard and throbbing, even though I hadn’t touched it this whole time. “I think I’m gonna cum!”

  Jenny gasped with delight as I said the words, fucking me even harder, both of us now gazing down at my cock, watching as, with a final cry, I arched my back, then started to squirt, my dick pumping out the biggest fucking load of my life, shooting high up onto my belly in a series of long creamy white streaks.

  And I watched in amazement as, between my legs, Jenny began to cum too, her thrusting stopping as her body bucked and shuddered, her eyes closing and her mouth opening in that expression I knew so well.

  She’d told me before that she came pretty easily – never needing to fake it – but holy shit, the idea that she’d cum too, just from fucking me drove me wild with happiness.

  It was like the two of us together had stumbled upon a whole new world of pleasure; a world which we had the rest of our married lives to explore.

  As she tugged off the harness, she flashed me a grin, one that seemed to tell me she was thinking the exact same thing. And as she joined me on the bed, both of us flushed and sweaty, cuddling together in our matching lingerie, our smooth legs rubbing together, I don’t think I’d ever felt happier in my entire life.

  “That was amazing,” I murmured, my voice still trembling a little.

  “It was, wasn’t it?” she sighed happily, her hand resting gently on my hip. “Oh and Mike?” she added with a giggle. “You know how it’s a private beach we’re going to on our honeymoon?”

  “Yeah?” I replied softly.

  “Well, I think I went a little overboard on bikinis in the end. So … would you mind wearing a few, too?”

  Business Class

  1

  “Adam, can we run through my presentation one last time?”

  I looked up at my sister, grinned, then shook my head. “Come on, Amy,” I laughed, “we’ve rehearsed it so many times already, even I know it off by heart! Good afternoon, before I begin my presentation, please let me introduce myself. My name is Amy Williams and ...”

  “Okay, okay,” she sighed, slumping down next to me on the couch.

  I tried to stay focused on the TV, but pretty soon her knee started to jiggle in that way that meant she was nervous and distracted – I knew this because as twins, the exact same thing happened to me whenever I felt that way.

  “You’ll be fine, just relax,” I urged. “Want a beer? It might calm your nerves?”

  “Thanks but no,” she smiled back, her knee still jiggling like crazy. “I really need to keep a clear head.”

  “Suit yourself,” I said, taking another big gulp of mine, then letting out a long, satisfying burp.

  “Adam!” she groaned, shaking her head and punching me in the arm. Then she pushed herself off the couch again and announced, “I’m gonna go to my room and do some last minute prep.”

  I couldn’t help but smile as she left; in a lot of ways Amy and I were similar, but in terms of organi
zation we couldn’t have been more different. I’d always been a ‘seat of the pants’ kind of guy, doing everything at the last minute, while she preferred to organize everything to the point where it drove her crazy.

  Take this business presentation she’d been practicing for. Sure, it was a pretty big deal – if it went well, she would get to design the new logo for some high-flying tech company – but she’d been rehearsing it for weeks, even roping me in to go over her speech with her, and on top of that, the small suitcase that was standing by the door ready for tomorrow morning had been packed weeks ago, too.

  But I guess that was probably also the reason that Amy was making amazing money as a freelance graphic designer, living in an awesome city center apartment, while I was still totally broke and out of work, couch surfing until I could find something more permanent.

  Now that she’d gone, I stretched out across the whole couch, resting my feet up on the arm and taking another big drink of beer, glad that I didn’t have anything to do tomorrow, other than search online for work.

  But little did I know, things were about to take a very different turn ...

  I woke around ten the next morning, still lying on the couch and dressed in all my clothes, my head fuzzy from one two many beers and the TV still blaring away into the room. But something felt different. For a start, the shutters were still drawn – Amy always opened them first thing, which was what usually woke me up. And on top of that, I craned my head to see that her suitcase was still standing by the door, even though her flight was only a few hours away and it was never like her to rush to the airport last thing.

  “Hey, Amy?” I called out. “You still here?”

  There was a pause, and then I heard a muffled groan from her bedroom.

  What the hell?

  I pushed myself up off the couch and knocked on the door.

  “Hey,” I called, “you okay in there? Shouldn’t you be heading to the airport soon?”

  Again, I heard a groan, and I pushed open the door to see her still in bed, the covers pulled up so just her head was poking out, her eyes red and puffy and her face all sweaty, her blonde hair mussed up and her nose streaming with snot. Sure, she normally looked kinda different in the mornings without her makeup and her hair extensions in, but today I had to admit: she looked like total crap.

  “What the hell, Amy?” I said. “Are you okay?”

  “I don’t know,” she murmured, her voice barely more than a croak. “I ... think I have flu.”

  “Oh shit,” I gasped, knowing just how important this trip was, “you think you’re going to have to cancel the presentation?”

  “I can’t ...” she muttered, shaking her head defiantly, even as she let out another woozy groan. I watched as she tried to push herself out of bed but then flopped back again, her flushed brow beaded with sweat.

  “I think you’d better stay in bed,” I said gently. “There’s no way in hell you’re going to be able to present anything like that.”

  “But the presentation itself isn’t until tomorrow,” she murmured, this time actually forcing herself up into a sitting position, then swinging her feet over the side of the bed. “I just need to fly today, that’s all. If I can get onto the plane, I can sleep it off tonight in the hotel. What time is it anyway?”

  “A little after ten,” I replied.

  “Oh shit, I’d better go,” she murmured, obviously still groggy and dizzy, as she pushed herself up to her feet then stumbled toward me in her pyjamas like some kind of zombie, trying to make it past me to the bathroom but only getting a few feet before she crumpled again.

  I quickly leapt forwards, catching her before she totally fell to the floor, then I led her back to bed, sitting her down and tucking her under the sheets again.

  “Amy, you’re sick,” I insisted, resting my hand on her sweaty brow and assessing her temperature – sure enough she was burning up like crazy. “You’re not going to make that flight. And anyway, they’d never even let you board. You’ll just have to rearrange the presentation. I’m sure they won’t mind if ...”

  “No Adam!” she practically screamed, her voice hoarse and ragged. “If I don’t make that presentation I’ll lose the contract for sure. That’s all there is to it. I have to go ...”

  But as the truth about her situation finally seemed to dawn on her, I watched as her face crumpled and she burst into tears, her body shaking with the sheer force of her sobs.

  “Hey, hey, it’s okay,” I tried to soothe her, but it was no use.

  She was obviously heartbroken.

  “It’s all fucked,” she moaned between sobs. “And there’s nothing I can do. I just wish ...”

  But then all of a sudden her eyes widened and a strange new expression flashed onto her face. In a heartbeat, her tears had stopped and instead she was smiling.

  Smiling at me.

  “What?” I asked, puzzled. “What is it?”

  “I’ve just had the most amazing idea,” she said with a grin.

  2

  “Fuck no!” I exclaimed.

  It was the craziest idea I’d ever heard in my life.

  “Come on, Adam. Please?” she pleaded, giving me those big puppy dog eyes. “People are always saying how similar we look. It would be easy, you’d just have to ...”

  “No way!” I interrupted, shaking my head for good measure. “You’ve gone totally crazy!”

  Because if you haven’t guessed yet, Amy’s ‘brilliant plan’ was for me to go on the trip in her place. After all, I already knew her presentation off by heart, and it was true – as identical twins we were pretty similar looking, with a few obvious differences of course. Namely, the fact that I had stubble, no tits and a dick.

  “People always say how similar we look, all you’d need is a little make up and ...”

  “No!” I cried again. “It’s insane.”

  “So what’s the alternative?” she sighed, the tears starting to brim in her big blue eyes once again. “If lose this contract, I’m going to find it difficult to make rent next month, and that means you don’t have a place to crash ... But if you help me out, if you get me the gig then I’ll have enough money to pay rent for a whole year. I’ll even have enough left over to set you up in a place of your own, too. C’mon, please?”

  I had no idea that things were quite so precarious with Amy’s finances, and maybe she was just saying it to try to convince me, but how the hell was I supposed to turn her down? And on top of that, the idea of her helping me get a place of my own was pretty attractive …

  “So what exactly are you suggesting again?” I said, slumping to a seat on the side of the bed as Amy once more ran through her crazy plan.

  “It’s easy,” she said. “You dress as me, take the flight as me, and check into the hotel room that the company have paid for as me. And then tomorrow, you give the pitch, just like we rehearsed, and then you fly home. That’s all there is to it. You’ll be back here by tomorrow night.”

  “You make it sound so simple,” I laughed, “but seriously, Amy? Is anyone really going to believe that I’m a girl?”

  “Look at my face now,” she said, staring at me head on.

  I looked closely at her – at her blue eyes, her slim nose, her lips, her chin.

  “Now tell me, like this, without makeup, is my face really so different to yours?”

  “I guess not ...” I murmured. “But what about the other stuff? The fact that you have tits for a start!”

  “Adam, I’m a B cup at best,” she grinned. “Ever heard of chicken fillets?”

  I shook my head, wondering what the hell she was even talking about.

  “Well, you’ll find out soon enough,” she said with a weird grin.

  “Okay, so I might look like you, but what about your voice?” I continued.

  “Remember when we were kids?” she shot back. “You were always doing impressions of me, answering the phone, pretending to be me ...”

  “Yeah, before my voice broke,” I cut
in.

  “I’m sure you’ve still got the knack,” she said.

  I felt a lurch of nerves in my stomach – we were seriously considering this now. It was the craziest idea in the fucking world, but at the same time I felt like it was too late to back out on her now. I simply couldn’t break her heart. And what’s more, I really didn’t want her to lose the job – or her apartment.

  “You’ve got just over an hour until you need to be at the airport,” she said. “I’ve laid out my flying outfit today on the chair by my dresser. You go put it on, then come back and I’ll do your makeup and put in the hair extensions.”

  “I can’t believe we’re actually doing this,” I groaned.

  “Hurry up, Adam!” she hissed. “We haven’t got much time!”

  Shaking my head at the craziness of what I was about to do, I headed over to the chair by her dresser where, sure enough, just like overly-organized Amy, she’d laid out a full set of simple comfy clothes to travel in – a sweater, a t-shirt, leggings, bra and ...

  “A thong?” I gasped. “You really expect me to put that thing on?”

  “C’mon, be a grown up about this,” she said sternly. “You seriously want to be seen with panty lines?”

  Again I shook my head, then picked up the bundle of clothes and turned to head to my room.

  “Oh, and you’ll need that box on the dresser too, the small black one,” she added.

  I picked it up, then left her room, hearing her sniff and splutter as a fresh coughing fit hit her.

  What the hell am I getting myself into? I thought to myself as I carried her clothes through to the living room, then dumped them in a pile on the couch.

  And then, with a frustrated sigh, I started to get undressed ...

  3

  The first thing that flashed through my mind as I pulled off my jeans – the same one’s I’d slept in – is that I should probably go for a shower first. And then a moment later, as I caught sight of my leg hair, I realised I should probably shave that off, too. This was getting crazier by the second, and I still didn’t know if Amy’s stupid plan would even work. But still, if I was going to do it, I figured I’d better do it right.