First Time Femme Read online

  First Time Femme

  Feminization Anthology

  D.L. Savage

  Contents

  Copyright

  In Her Shoes

  Chapter 1

  Chapter 2

  Chapter 3

  Chapter 4

  Chapter 5

  Chapter 6

  Chapter 7

  Chapter 8

  Chapter 9

  Chapter 10

  Epilogue

  Pink Box

  Chapter 1

  Chapter 2

  Chapter 3

  Chapter 4

  Chapter 5

  Chapter 6

  Chapter 7

  Chapter 8

  Chapter 9

  Chapter 10

  Chapter 11

  Trans-Form

  Chapter 1

  Chapter 2

  Chapter 3

  Chapter 4

  Chapter 5

  Chapter 6

  Chapter 7

  Chapter 8

  Chapter 9

  Chapter 10

  Epilogue

  Mr Big

  Chapter 1

  Chapter 2

  Chapter 3

  Chapter 4

  Chapter 5

  Chapter 6

  Chapter 7

  Chapter 8

  Dream Girl

  Chapter 1

  Chapter 2

  Chapter 3

  Chapter 4

  Chapter 5

  Chapter 6

  Chapter 7

  Chapter 8

  Free Pass

  Chapter 1

  Chapter 2

  Chapter 3

  Chapter 4

  Chapter 5

  Chapter 6

  Chapter 7

  Chapter 8

  Chapter 9

  Secret Summer

  Chapter 1

  Chapter 2

  Chapter 3

  Chapter 4

  Chapter 5

  Chapter 6

  Chapter 7

  Chapter 8

  Bully

  Chapter 1

  Chapter 2

  Chapter 3

  Chapter 4

  Chapter 5

  Chapter 6

  Chapter 7

  Chapter 8

  A Note from Dana

  Also by D.L. Savage

  © 2019 Dana Louise Savage

  Cover image © 2019 - FlexDreams - Depositphotos.com

  In Her Shoes

  1

  “I can’t believe you just said that!” Tawna screamed, her voice cutting through the din of the bar, her brown eyes widening as she picked up her glass of wine menacingly, like she was about to toss it over me.

  “What?” I laughed, throwing up my hands. “It’s just a fact. Girls have it easier than guys.”

  To be honest, I suspected the opposite was true, but it was so damn fun to annoy her – to watch her pretty face grow angry at whatever stupid claim I was making. And on top of that, pissing off Tawna was about the only way I knew to make a classy girl like her pay attention to me.

  I scanned the bar, this place where I’d spent almost every Friday night for the last few years relaxing after a hard week at work, looking from Dave the bartender, to Miguel, to Jimmy – hoping one of the other regulars would back me up. But none of them seemed willing to throw their hat into the ring, instead just watching on eagerly to see what Tawna would do next.

  “You carry on talking like that,” she threatened, “and I might ask Henry here for a pair of scissors so that I can cut off that stupid top knot of yours.”

  At her words, everyone burst into laughter, and I found myself having to force a smile onto my face, even though her little jibe about my fashion sense cut to the quick. I guess deep down I knew that they thought my hipster affectations were a little ridiculous, but even so I still found my hands flashing up to my head protectively, covering the long twist of chestnut blonde hair that had taken me over six months to grow, if not longer.

  “Stand up,” Tawna said a moment later, urging me to my feet with her hands.

  “Huh?” I said.

  “You heard,” she growled, her pretty face growing totally serious now.

  A little confused, I eased myself up off my bar stool and onto my feet.

  “Turn around,” she continued, swirling a long perfectly-manicured finger in the air.

  Again I did as she said, slowly shuffling around in a circle as everybody watched on, all of us wondering what point she was making now.

  “And what is it you do again, Leo?” she asked.

  “I’m a software developer,” I replied.

  “And you work in an office right?” she persisted. “They actually let you come into work dressed like that?”

  I nodded, feeling my face flush with heat as Tawna’s point slowly sank in. It was true; I’d spent all day (hell, all week) working at the office in the very same scruffy jeans and plaid shirt that I was now wearing to the bar.

  “Now take a look at me,” she continued, doing just as I had done and spinning in a slow circle so that everybody could get a good look at her outfit.

  As she turned around, I couldn’t help but sneak a hungry look at her perfect bod. Like me, Tawna lived in the neighborhood, which meant she always dropped into the bar straight after work. Therefore she was usually wearing thje kind of classy business outfits – pantsuits, tight skirts, heels – that I found super sexy. Tonight was no exception; her cream white pantsuit hugged the curves of her ass so tightly it looked like a second skin. Tawna was obviously someone who kept herself in shape, her expensively tailored outfit showing off what looked like a toned, athletic bod beneath.

  “This is what I have to wear every day to work,” she explained, gesturing down at her trim figure.

  “You don’t have to,” I replied with a shrug.

  “Oh don’t I??” she exclaimed. “So you really think that if I rocked up to the office on Monday in a scruffy shirt and cum-stained jeans, my boss would be cool with it?”

  I paused, as all the regulars looked back to me, wondering if I’d have the nerve to keep up this stupid argument any longer. Truth was, I knew deep down that Tawna was right. But even so, four beers in I was simply enjoying the fact that she was paying attention to me, so like an idiot I decided to keep our sparring match going a little longer.

  I sucked in a deep breath and then said it, the statement that would change my life forever: “You girls make it sound like you go through agony every day, but seriously, how hard can it be?”

  “Oh you think this is easy do you?” Tawna shot back, her dark brown eyes flashing with fire.

  “Uh huh,” I replied, folding my arms across my chest, too stubborn and pig headed to back down

  “You reckon you could go through all the shit that I do day in day out without complaining do you?” she countered.

  “Absolutely,” I replied, still sticking to my guns.

  “Hundred dollars says you can’t spend a day in my shoes,” she announced, shoving her hand out toward me.

  “Huh?” I replied, stalling for time as I felt a tug of nerves in my stomach, wondered if perhaps I’d gotten a little out of my depth here, especially when I noticed that all the other regulars at the bar were looking at me excitedly now, waiting for me to take Tawna up on her bet.

  But I knew that I’d look like a total pussy if I lost face.

  Ah fuck it ...

  “Alright, it’s on,” I announced, reaching out and grabbing her slender hand tightly in mine, pumping it up and down as everyone around us laughed and cheered.

  And as she let go of my hand, I reached out and grabbed my beer, knocking it back in one. But as I turned to the bar to order another, I just hoped to god that this stupid bet would be
totally forgotten in the morning ...

  2

  The next morning I woke with the mother of all hangovers. It was a baking hot day outside, the sunlight blazing unforgivingly through the blinds and my skin was covered in a thin sheen of sweat, my thin cotton sheets tangled around my ankles where I must've kicked them off in the night.

  I winced as I felt a pounding headache throb at my temples. Shit. How many drinks did I end up having last night? Six? Seven? But then another memory struck me, causing me to wince even harder: that stupid bet I'd made to Tawna, the one where I’d claimed that girls had it easier than guys.

  Why the hell had I even said that?

  I knew deep down I’d just been mouthing off, the way I always did to try and attract female attention. Very occasionally it worked, but most of the time I went too far, and this was definitely one of those times. My only hope was that Tawna saw the whole situation the same way I did, as nothing more than a joke. She wasn't actually gonna see it through, was she?

  Nah, I thought as I pulled off the damp sheets from my body then climbed out of bed, wincing as my head throbbed even harder now that I was upright, the creak of my feet on the floorboards sounding almost deafeningly loud.

  At least it was Saturday, I reminded myself. The idea of a whole weekend just slobbing around the apartment in my boxer shorts, not even bothering to wash or shave, seemed like heaven. And despite my pounding skull I found myself grinning at the thought that in actual fact us guys did have it a lot easier than girls.

  But just as I was padding out my room and down the hall to the bathroom, something stopped me in my tracks:

  Buzzzzz ... Buzzzzz ...

  The doorbell.

  But who the hell could it be? I wasn't waiting for any packages to be delivered, and I certainly didn't know anyone that would come over to my apartment at such an ungodly hour on a Saturday morning. Maybe whoever it was had just got the wrong address, and so I decided to ignore the sound and carry on down the hall to the bathroom.

  But another insistent buzzzzzz stopped me once again in my tracks, and this time I could hear banging, too.

  God damn it, I thought as I finally diverted course and headed to the front door. But when I finally yanked it open, my nerves jolted as I saw Tawna standing there, a mean grin etched on her perfectly made up face.

  “Surprise!” she said playfully.

  I’d never seen her like this, dressed not in office wear but instead in what I guess you’d call casual, weekend clothes (although her simple outfit of cream blouse, skinny blue jeans and nude heels still had an air of expensive luxury about it).

  “But how the hell did you even find out my address?” I blurted out.

  “Dave the bartender told me,” she replied with a wry grin. “What? You think I wasn't gonna see through our little bet?”

  “Maybe, yeah,” I admitted with a shrug.

  “Well bad news, bucko,” she grinned. “Because I know for a fact that I’m really gonna enjoy seeing you put your money where your big mouth is for once. And once I’m done with you, maybe you’ll have learnt a lesson or two about writing checks your ass can’t cash. Here take these,” she added, thrusting a package of aspirin and a bottle of mineral water toward me.

  “Thanks,” I replied, taking the items from her, genuinely grateful for the aspirin. “That’s actually really kind of you.”

  “Kind?” Tawna snorted, shaking her head. “Shit no, I’m not being kind. You’re gonna need that stuff after the hell I put you through today.”

  I couldn’t help but let out a groan of despair, wishing I'd never opened my big mouth.

  “So are you gonna invite me inside or what?” she snapped.

  “Oh sorry,” I murmured, turning and leading her back into the apartment. “Hey, you want some coffee?” I called over my shoulder, figuring I might as well try and sweeten her up a little. “I might start making breakfast too if you want some bacon and eggs?”

  “Uh, uh, uh,” Tawan replied sassily, shaking her head and wagging an expertly manicured fingernail at me. “You need to watch your figure.”

  “Watch my what?” I said, totally baffled and confused.

  “First rule of being a girl,” she shot back, hands on hips. “You’re on a strict diet of mineral water until at least lunchtime.”

  I let out another sigh of frustration. God damn it. This was gonna be even harder than I thought.

  “Well don’t just stand there,” she said, looking at me like I was a total idiot. “Go take a shower! Let’s get this show on the road. Oh and Leo?” she called after me as I started down the hall toward the bathroom. “Make sure to give your body a real good scrub, and shave your face baby smooth, too. After all, you see me with any stubble?”

  I shook my head, still hoping her stern expression might crack into a smile and she’d announce that this whole thing was just a practical joke.

  “And once you’re done, put these on beneath your clothes,” she added, reaching into her handbag and fishing around in it, before pulling out a scrap of neon pink cloth. For a half-second I innocently thought it might be a handkerchief, but as she tossed it to me the mysterious item unfurled in midair, revealing its true self: a thong.

  “You’ve got to be kidding me,” I muttered, shaking my head as I stared down at the panties in pure horror, my eyes latched onto the small tag at the back which read Victoria’s Secret.

  But when I ventured a timid glance in Tawna’s direction, her icy cold expression told me that she was deadly serious…

  3

  As we made our way along the busy sidewalk, right in the heart of downtown, weaving in and out of the crush of Saturday morning shoppers, my stomach let out a deafening rumble and I winced, daydreaming about bacon, eggs and pancakes. But it seemed like Tawna was being serious: I really wasn't allowed anything other than that puny bottle of mineral water, which was supposed to tide me over until lunchtime, seeing as I was 'watching my figure’.

  What was even worse than my empty stomach though was the constant wedgie I was receiving from the tiny pink thong.

  Sure enough, she’d not left let me leave the apartment until I'd passed her panty inspection; Tawna circling me like a stern sergeant major before fishing a long glossy fingernail down the back of my jeans to tug out the bright pink strap at the back.

  And now I could feel it, the stretchy pink lace hugging my cock and balls so tightly it was crazy, while at the back the strap seemed intent on working its way deeper and deeper into my crack with each damn step I took.

  Eventually I couldn't take it any longer, and in a moment of frustration I found myself reaching around and unselfconsciously shoving my hand into the back of my jeans in order to try and pick the annoying butt floss from my crack. But before I could grab hold of it, I felt a sharp sting against my palm as Tawna swatted my hand away.

  “Leave it,” she hissed. “You see me picking at my thong right now?”

  “No,” I murmured, shamefaced.

  “Exactly,” she replied. “Because that’s one of the first things you need to realize, Leo. The things girls wear? They’re chosen to make us look good, not to make us feel comfortable. You want hideous panty lines? Then go ahead and put on a pair of huge, washed out granny panties. But if you want your ass to look smooth and round and hot in a pair of skinny jeans or a tight little miniskirt, then you’re simply gonna have to wear a thong.”

  Rant over, we continued strolling along the busy sidewalk in silence for a while, and I felt Tawna’s words slowly sinking in. I guess I’d never really paid too much thought to all the sacrifices to comfort girls made on a daily basis.

  What's more, I couldn't help but think about something else she’d said – that she was wearing a thong right now, too.

  I snuck a glance over at her lower half, feeling a strange flutter of horniness. But this wasn’t simply from checking her out, it was more from the odd knowlege that she and I were experience experiencing the exact same thing right now; that just like me,
Tawna was experiencing that subtle butt-flossing sensation as she walked, and soon I could feel my cock throbbing and tingling in my panties despite myself.

  “Well, here we are!” she announced just then, busting me out of my thoughts.

  “Huh?” I replied, looking around myself confused, wondering which of the nondescript buildings nearby she was taking us to.

  But as I caught sight of the large yellow sign right above us, the one that read Sweet Spot Tanning and Waxing Salon, I felt my stomach churn all over again.

  “You can't be serious,” I groaned.

  “Oh, Leo,” she replied, her big brown eyes flashing with glee, “I think if we’ve established one thing by now, it's that I’m not fucking around. By the end of the day, you’re to know exactly what it feels like to be a girl …”

  * * *

  “Please no more,” I begged an hour or so later, wringing my hands pathetically, begging like a worm.

  I felt so ashamed, lying there on the table, practically naked save from a pair of paper panties, my scrawny body on full display, my eyes watering, as I watched as Tawna's cruel gaze flick first to Clara, the cute blonde beauty assistant who could only have been eighteen or nineteen years old, then back to me again, a mean smirk dancing on her full, glossy lips.

  “What’s the matter?” she teased. “I thought a big strong guy like you could handle the pain! Anyway, were almost done,” she added. “Your legs, chest and back are all baby smooth. All that's left is your bikini line ...”

  “Is that really necessary?” I moaned.

  “Of course,” Tawna shot back, while the pretty young assistant watched our exchange in shocked disbelief. “So c’mon, Leo, turn onto your side and hug your legs up to your chest so that Clara here can set to work on your ass crack ...”

  I felt like I was trapped in some kind of nightmare, knowing there was nothing I could do but comply. So with a shameful sigh, I did as Tawna instructed, turning onto my left hand side and then hugging my knee to my chest, gritting my teeth as Clara began to tug the hem of the paper panties to one side, then smear the warm wax directly onto my ass crack and taint.