Feminized for the Very First Time: 8 Books Feminization Anthology

by D. L. Savage

  I nodded, totally at Blake’s will now, knowing I’d do anything he asked of me.

  “Adam, you get down on the floor here,” Blake instructed, and I watched opened mouthed as Adam lay down next to me, his cock jutting up towards me, the rest of the group making a circle around us.

  “Go on, baby. Ride him,” Blake said sternly, nodding down at Adam’s shiny, twitching cock, protruding straight upwards from between his thick muscular thighs.

  And I did just as I was told, straddling Adam, poised above him, my body trembling, my little sissy clit throbbing in my soaked through panties as I watched him spit onto his fingers, tug my thong to the side, then begin to work the wetness roughly into my tender little asshole.

  Can I really do this? I thought. Am I ready?

  I nervously lowered myself down onto him, offering up my tight little asshole as he confidently pushed the tip of his cock slowly inside me, causing a mixture of pleasure and pain to flash right through me. Fuck, it felt like he was going to split me right in two.

  “That’s it, baby,” Blake said, his black eyes flashing as he watched me. “Take him deep now. Good girl, good girl ...”

  I gasped and moaned as Adam began to feed even more of himself slowly inside me, stretching my butt wide open, his cock feeling impossibly long and thick as he gently slid it deep into my ass, while Brett came and stood in front of me, offering his identical cock to my gasping, open mouth.

  I took it eagerly, sucking on it like my life depended on it, feeling so totally filled by these two twin hunks, my body quaking in a way I’d never before known as they both began to fuck me, rhythmically, each of their deliciously long thick cocks sliding in and out of my mouth and ass in a beautiful rhythmic motion, while their hands explored my body, their fingers in my hair, on my neck, on my buttocks, even toying with my aching balls and caged up sissy clit. As I writhed between them, I looked around the room, catching eyes with all the other guys, some of whom were stroking their big hard cocks again, and through a small gap in the crowd I could see Mia, over on the bed, riding some guy just like I was doing now. She looked so fucking hot, totally naked now except for her black silk stockings, her breasts bouncing – and I felt a pang of envy when I saw them, because unlike mine they were real, small and pert with hard little nipples. And between her legs, her small soft cock jiggled and bounced, totally limp.

  I kept my eyes on her as, with each fresh thrust of these two cocks inside my ass and mouth, I felt new shivers of pleasures ricocheting out around my trembling body.

  Oh god, oh god, I thought as they pushed me right to my very limits, fucking me hard and rough in a way I’d quickly grown to crave.

  Just then, I heard Mia cry out in a long moan of her own, and I watched in awe as she arched her back, steadied herself on her guy’s muscular thighs, her still-limp cock suddenly starting to spray out a powerful series of thick white ropes of cum, her eyes closed and her mouth open, lost in her pleasure.

  And I could feel myself beginning to come again, too, partly from the sight of Mia and partly from the way these two twin studs were fucking me, hard and rough, without a care for me, just using my slim body and mouth for their own pleasure. And this time I totally let go, squealing and crying out in the loudest moan, as I came almost painfully hard on both their cocks at the same time, my pussy and mouth both clenching tight around them, my hips thrusting, my little sissy clit once again flooding my already soaked panties.

  Moments later, I felt Adam come too, unloading into my ass with a pure liquid heat, then I heard Brett growl and grunt, holding my head in place and driving his cock deep into my mouth as his hot come spurted into my throat.

  It was so crazy; I’d never even dreamed sex could be like that, so rough, so nasty, so fulfilling.

  Because all I felt in that moment was pure pleasure, coupled with the sweet ache of knowing that it was almost over, and that soon, very soon, I’d be craving it all over again ...

  Epilogue

  And so that was how I came to be Julia, a high-class sissy hostess, just like my best friend Mia. I’d enjoyed my first night on the job way more than I could have ever imagined – and when Mia gave me my cut of the earnings, as cool as it was to get the five grand I’d been so hungry for, I also couldn’t help but smile to myself, knowing deep down that I would have done that for free if I’d known how much I’d enjoy it.

  And pretty soon, I was living a life similar to Mia’s, too – renting my own apartment in the same block as hers, with more money than I knew quite what to do with.

  What’s more I’m even transitioning , growing my very own breasts, just like Mia’s. And I’ve even learnt how to stay limp when I cum, too! The trick is not to focus on your dick – or your clit, as I’ve come to think of it these days – just to treat your orgasm as a full-body experience, just like any real woman would.

  In fact, I know so much more now, about myself, about life, than I’d ever dreamed I would. I’m happier, too. Happier than I ever was as Jacob.

  Because I’m Julia now.

  Now and for forever.

  Ladies Night

  1

  “Oh my god,” Lisa, my sister-in-law announced one evening, her dark eyes sparkling and her glossy lips curling into a big grin, “I heard about this amazing club from the girl in the hair salon today and we just have to go!”

  “What, like a nightclub?” my wife Joanie laughed, shaking her head. “Aren’t we a little old for that?”

  I remained silent while their conversation played out, just sipping my beer and trying to keep focussed on the TV. But the more they talked, the more intrigued I became.

  “Come on, you only turned thirty last year, big sis!” Lisa insisted. “You’re still young. We both are. And we should be out having fun. Don’t you think so, Dave?”

  As the two women turned to me, I mulled it over in my head. It did seem kinda silly for us to be going out to a nightclub, but at the same time Lisa was right, we weren’t that old. I had just turned thirty-one, Joanie was thirty, and Lisa was still in her mid-twenties.

  “I guess a club might be fun,” I ventured, trying to cast my mind back to the last time I’d set foot in one, back when I was single in College, desperately trying to find a girl who’d be interested in someone like me – a plain, skinny guy without much confidence. “Maybe we could all check it out this weekend?” I offered. But secretly I hoped we wouldn’t actually have to go. After all, I wasn’t much of a dancer and I suspected I’d feel even more out of place in a club now than I had done back in my twenties.

  “Actually,” Lisa replied with an apologetic smile, “the night I’m talking about is ladies only.”

  “Like a lesbian night?” Joanie laughed. “Since when were you into that?!”

  “Oh no,” Lisa replied with a strange smile, before leaning in and whispering something in her sister’s ear, obviously making sure I didn’t catch a word of what she was saying. And as Lisa whispered, I watched my wife’s pretty blue eyes widen in disbelief as a blush crept across her cheeks.

  “No way!” she laughed.

  “Yes way,” Lisa insisted. “So, you wanna come with?”

  “I don’t know,” Joanie sighed, casting an embarrassed glance in my direction. “Would you mind honey?”

  There was something about the way Joanie said this – not to mention something about the way Lisa had leant in and whispered in her ear – that told me this was no ordinary club ... That there was something odd about it.

  But if I’m honest, while a part of me certainly felt concerned at the idea of my wife going to some strange, secretive ‘ladies only’ night, another bit of me simply got excited at the idea of grabbing some time to myself since Lisa had begun staying with us. It was only ever supposed to be for a few weeks – just while she found her feet after her break up with her last boyfriend, Greg – but weeks had turned into months, and it felt like I’d had no damn time to myself.

  So instead of asking the women what happened at this s
trange nightclub, I simply smiled and said, “Sure, honey. You girls should go out and have fun.”

  Again, I watched as something strange and secretive passed between them – all in a flicker of eye contact – before Lisa announced, “In that case, we’ll go tomorrow night!”

  And so that’s exactly what happened. The following night, which was a Friday, the two sisters got ready to go out, both taking long showers, then getting dressed up, sharing makeup, giggling and laughing as they primped and preened in the large dressing mirror in the room I shared with Joanie.

  I kept out of the way, sitting downstairs in the lounge with a cold beer and my feet up in front of the TV, but I could hear their excited voices murmuring away upstairs, and when they finally came down the staircase to say goodbye, holy shit, they both looked amazing.

  Now I love my wife dearly, don’t get me wrong, but any guy will tell you that it’s hard to stay attracted to the same person you see every day, especially when more often than not she’s dressed in baggy sweatpants and a sweater. But that night, Lisa had worked wonders on Joanie – coaxing her strawberry blonde hair into a glossy mass of curls, accentuating her blue eyes with expertly applied eyeliner and mascara and bringing out her full lips with bright red lipstick. I could tell she’d leant her a dress too, because it was the kind of thing Joanie never normally wore – tight and short and black – paired with a set of simple black heels.

  For the first time in years, it was clear to me again that these two girls were sisters – both made up like that they looked so alike it was crazy.

  Lisa meanwhile looked as smoking hot as ever. I’d had something of a secret crush on my sister-in-law ever since I first met her – one that I made sure never to let on about, and one which of course I intended to do nothing about either, even if the situation were ever to arise.

  Not that it would. Lisa was way out of my league; sexy in a full-on, flirty way, unlike homely, shy Joanie who was much more my usual type. But there was something about Lisa that got me hot – maybe because she reminded me of those mean, sexy girls from my teenage years – the ones I’d secretly lusted over all through high school but knew I never had a chance with.

  And tonight she looked smoking: dressed in a similarly tight dress as her sister’s, only in bright, dazzling white, her slim toned body on full display, her dark hair tied up in a high sexy ponytail that swung teasingly whenever she moved her head. As a final little reminder of how naughty she was, as she turned around to grab her purse from the floor by the staircase, I found my eyes glued to her perfect butt – shown off by that criminally tight white dress – and the clear outline of a skimpy white thong beneath.

  I felt my cock hardening despite myself. Joanie never wore those kinds of panties – always shrugging the idea away as impractical and uncomfortable.

  Why would I want to put on something that flossed my butt all day? she’d laughed, shaking her head, the one and only time I ever brought up the idea of her wearing them.

  “Well, have fun sweetie,” she said just then, breaking me out of my thoughts about her sister, and I felt a blush of shame flush my face.

  “You too,” I said, leaning in and kissing her, before turning to smile at Lisa, hoping to hell my dirty thoughts about her sexy underwear didn’t show on my face.

  “From what I’ve heard, this place can get pretty wild, so we’ll probably be back late,” Lisa added with a knowing smile.

  Just at that moment, we all heard the sound of their taxicab beeping its horn from out front of the house.

  “Okay, have fun ladies,” I said, catching one final glimpse of Lisa’s perfect ass as the two women grabbed their purses then raced out to the taxi.

  And once the door had closed behind them and I was finally left in the house alone, I felt my thoughts wandering once again to the idea of a ladies only night. From what I gathered, it wasn’t some lesbian place, yet Lisa said it got ‘pretty wild’. But even so, what exactly was it they’d be doing? Probably just dancing to all the kinds of corny, trashy pop music they loved in their youth …

  I shrugged off my uneasy thoughts and made my way back toward the couch. I’d been looking forward to a night of TV and getting gently buzzed – watching the kinds of shows that Joanie never wanted to watch – ever since they’d first mentioned their night out, but now, as I eased myself back down onto the leather couch, cracked the lid of my can of craft IPA and took my first slow pull, I found myself unable to concentrate on Ice Road Truckers, even though it was one of my favorite shows.

  Instead, I found my mind wandering back again and again to the sexy image of Lisa’s ass and before long I just knew that I would have to jack off if I was going to get through the rest of my night the way I’d planned. Because right now, the sensations of horniness were growing like a swarm in my stomach and fogging my thoughts to the point of total distraction.

  With a frustrated sigh, I set my beer can down on the side table and pushed myself back up off the couch, planning to head up to the bathroom, blow a quick load, and then carry on with my night of TV and beer as planned.

  But as I headed up the stairs and strolled past the open door to the guest room, where Lisa’s suitcase lay open on the floor, spilling its brightly colored contents over the carpet – no doubt from the many outfits she’d tried on and discarded before choosing that sexy white dress tonight – a strange new idea began playing around in my mind.

  And before I even knew quite what I was doing, I’d changed course, turning away from the door to the bathroom and stepping instead into the guest bedroom ...

  2

  As I knelt down in front of the open suitcase, my heart began to pound as it dawned on me just what I was about to do: root around in my slutty sister in law’s suitcase. What I was actually searching for, I didn’t quite know. I just wanted to take a closer peek at her clothes, not to mention any other items she might have brought with her while she was staying here.

  And as I began to search through the kinds of things Lisa had brought with her, it further accentuated just how different she was to Joanie. Because the clothes that Lisa wore all seemed designed to flatter, rather than hide her figure – yoga pants, crop tops, and mini skirts so short they were just tiny straps of stretchy elasticated fabric.

  I pushed my hand deep into the mass of clothes and pulled out a handful of tangled, brightly colored strips of cloth which I knew immediately were panties. I felt my blood charging with fresh excitement as I brought them to my face to inspect them, looking one by one at the skimpy little thongs and g-strings – all so different to the kinds of boring, conservative granny panties that Joanie always chose.

  I couldn’t help but imagine what it might be like to actually wear something like that, too; if it really was as uncomfortable and floss-like as Joanie insisted, or whether perhaps there might actually be a weird pleasure from wearing something so snug and tight and slutty beneath your clothes.

  In a moment of madness, I even considered trying on one of them: a hot pink number from Victoria’s Secret that had caught my eye. But I shook my head, disgusted at the weird crazy thought, and instead resuming my search through the suitcase to see if it contained any other interesting items.

  Sure enough, a moment later my fingers brushed against something hard yet silky, too – almost like the feel of human skin. I felt my pulse increase even further as I brought it out from the bottom of the suitcase and into the light, revealing a totally realistic dildo, complete with a bulbous pink head, ridged veins running down the shaft and even a set of big round balls at the base.

  I found myself unable to tear my eyes away from it, feeling an odd mixture of excitement and also shame the more turned on I got. Damn, my own cock was nowhere near as big as this monster, which must have been eight inches long at least, not to mention way thicker and meatier than my own pathetic little five-inch prick.

  With a shaky hand, I brought the dildo right up to my face and sniffed it, sure enough breathing in the faint yet recognizable s
cent of pussy. Lisa’s pussy. The idea of my slutty sister-in-law plunging this big fat monster deep into her sopping wet pussy was almost too much to think about, and I could feel my own cock straining in my boxer shorts now, totally rock hard and desperate for release.

  But there was some kind of fresh, sensual pleasure in ignoring my own urges and instead continuing to examine this strange treasure chest of feminine secrets. I lifted out the pair of pink panties again, once more marveling at just how different they were from the rough cotton of my own plain white boxers, once again imagining my sister in law wearing them as she did all kinds of kinky slutty things.

  I imagined her dressed in these panties and one of her mini skirts and a pair of silky stockings, sucking a real dick just as big and fat as this dildo, her nipples growing hard and her pussy getting all gooey and wet as she worked the cock in her mouth until ...

  All of a sudden, imagining simply wasn’t enough anymore. I wanted to actually feel what it might be like to wear those clothes, to do those things, and so with a pounding heart I realized in that moment I had everything I needed right here in this suitcase to live out this fantasy.

  Before I could change my mind, I began tugging off my clothes, my whole body charging with a nervous excited energy. And once I was totally naked, I selected my outfit: the thong, the red miniskirt, and I even found a pair of white hold-up stockings, just like the ones I’d been picturing.

  And then, once everything was ready, with my heart booming in my chest, I began to dress ...

  3

  I pulled the stockings on first, feeling the silky material sliding up over my legs, savoring the sensation which was like nothing else I’d ever known. As my right leg became slowly yet surely encased in the white nylon, I almost couldn’t believe how feminine it looked, how much more shapely and sexy it seemed than my left. I quickly pulled on the second one too, again marvelling at the transformation. As a guy, my body had been on the slim side, nothing to write home about. But now, dressed like this, my legs actually looked good.