by D. L. Savage
But even as I was speaking, my mind was flashing again with the image of her perfect ass, the way I’d eased down her black thong, the way her slender fingers had parted her buttocks, the quick sexy glimpse of her pussy and asshole and then of course, the rich sweet scent of her ass.
“Anyway,” I continued, “I’d better put these things safely in my room. She’s kind of a bitch, and she’d give me hell if anything happened to them.”
“Sure man,” Alex said from his seat on the sofa, as I began gathering up the shopping bags. “You want to play some Call of Duty later?”
“Maybe,” I lied, “but ... ah, actually, I think I’d better get a good night’s sleep, so that I can be in first thing with this shopping.”
“Okay, sure,” he said, as I scurried off to my room, closing the door behind me.
Once I was alone in my room, I began taking the clothes out of the bags and laying them on the bed, looking at the silky sexy fabrics of the blouse and underwear, and the deep black shine of the stilettos. These clothes seemed a world away from anything I normally wore – nothing at all like the rumpled, threadbare, over-washed cotton of my t-shirts and boxer shorts – almost as if they had come from some kind of alien planet.
And as I looked at them, I felt a tingling excitement coming over me, as I wondered what it might actually be like to dress up in them; to feel that silky, sexy fabric against my skin.
I glanced back towards the door to my room. In the whole time I’d been sharing with Alex, he’d never barged in and had always respected my privacy. So even though there was no lock, I knew that I was safe in here, safe to at the very least try on the clothes, even if I still thought the idea of coming into work tomorrow wearing them was totally insane.
So I began to undress, watching myself in the long mirror that had been standing in the room since the day I moved in, watching as I stripped off my rumpled work clothes, my t-shirt and boxer shorts, until I was standing there, totally naked: my pale skinny body on full display, totally lacking in any muscle or definition, my puny little cock dangling between my legs. Even my balls were pathetic – just as small and dainty looking as my dick.
I shot a glance over at the clothes laid out on the bed again, my eyes now lingering on the black thong panties. I padded over and picked them up, holding them up to really examine them for a moment, looking at the thin strap that would slip between my buttocks. It seemed like a whole world away from the kind of baggy, loose-fitting underwear I normally wore, and it seemed crazy that women actually wore things like this – women like Mistress Cartwright.
Before I changed my mind, I bent down and stepped into the panties, sliding them up over my thighs, then further still, feeling the silky fabric of the crotch stretching slightly to snugly cup my cock and balls, and then the strap at the back sliding between my butt cheeks. As I walked back over to the mirror to check what it looked like, I found I actually kind of enjoyed the tight, snug feeling and the ever-so-subtle sensation of the fabric against my ass.
I looked at myself in the mirror, and – wow. It actually looked pretty good! Okay, so there was a small bulge in the front of the panties, but it wasn’t even that noticeable, and the black color kind of hid it. And when I turned to inspect my ass, I was even more surprised. I guess I’d never even really thought about it, but dressed in the panties, my ass actually looked, well, great. My buttocks were round and pert, and apart from a fuzz of black hair, it could totally have passed for a girl’s butt.
Next I grabbed the bra and put that on too. I don’t even remember where I’d picked it up from but I knew that the easiest way to put it on was to fasten it around my waist like a belt, then turn it around and pull the straps over my arms. And again, what I saw kind of took me by surprise. Because my slightly flabby pecs, that formless puppy fat that I’d always hated on my chest until this moment, now actually looked like two – admittedly small – breasts, just about filling out the cups of the bra. And if I sucked in my slight gut, and held myself a certain way, well, apart from trail of hair that led up from my groin to my belly button, and the slight black fuzz that grew on my chest between my pecs, again you could be mistaken for thinking that this wasn’t even my body any more – but instead just a slim girl with small tits and a cute, pert butt.
As I checked out my body in the mirror, the tingling excited feeling increased inside me, mixing with a growing horniness too, and I could feel my cock swelling and my balls tightening, straining against the snug silky crotch of the thong. But to my delight, my cock was so small it didn’t even pop out of the top of the panties. Instead all that happened was that the bulge between my legs grew bigger, but stayed within the confines of the panties.
By now, I was actually pretty excited to try on the rest of the clothes, just to see what I might look like in the full outfit. First I pulled on the stockings, which had special elasticated tops to keep them held in place. Then I picked out the larger sizes of the skirt and blouse, and put those on too, marvelling at the way the bra accentuated my feminine figure, and the way the skirt hugged my hips and thighs. And then finally I turned to the shoes. There were three pairs, the largest a size smaller than my own feet. I sat on the edge of the bed and pushed my feet inside, worried for a moment that they’d just be too small. But after a little pressure, my feet actually slipped in, my toes squashing slightly painfully together. Standing up, the pain got worse but I ignored it, taking a few wobbly steps back towards the mirror, the click of the heels echoing loudly around my room.
And what I saw in the mirror was so strange. From the waist down, I was truly feminine. It was the craziest thing. I actually had a woman’s figure! Suddenly my slim body made some sense. For the first time, I actually looked hot. Well, almost all of me. Because as my eyes moved back up to my face, which was still just the face of a plain boring guy, I felt a deep pang of frustration, wishing that part of me too could be feminine – wishing my hair was long and luxurious and my face was pretty and cute instead of boring as hell.
So what the hell am I going to do? I thought. Am I really going to leave the house and go into work tomorrow like this?
It was either that or lose my job. But it was more than that too, way more. Because I had to admit that while the idea terrified me, the sheer humiliation of something like that – going out into the world dressed like this – turned me on like crazy.
I hardly slept that night, tossing and turning, worrying and fretting, wondering what the hell I was going to do on Friday morning. But in the end, I formulated a plan. I was going to do it – but I would leave the house in my regular guy clothes, and take my girly outfit to change into once I arrived.
So bright and early the following morning, way before Alex even woke up, I started getting prepared, packing my feminine outfit into a small rucksack, ready to put on at the office. And as I showered, I decided to shave my chest hair and as much of the hair on my ass as I could too, which I realize was kind of pointless. After all, no one would see it. But even so, I liked the idea of being as feminine as I could, even beneath my clothes.
And that morning, as I walked to work, I’d never felt so nervous – nervous and excited.
I arrived at the office a full half hour early, just as the cleaners were leaving, and I was thankful to have time to prepare. The main office was completely deserted and I headed towards the washrooms, pausing as I reached the doors – undecided whether or not to go into the male or female bathroom.
After a split second, I chose the small women’s washroom, quickly making my way inside and closing myself off into the only stall.
I felt a flash of panic, wondering if perhaps I was making some kind of mistake. If this was just the worst idea in the world. But another part of me felt like this was beyond my own control – that I was fully at the mercy of my cruel mistress, and that if she wanted me to do this, as humiliating as it was, then who was I to argue with her. And another part of me still felt excited, excited to once again put on my sexy, feminine clothes �
�� to feel the soft silk against my flesh, to feel the tight thong panties cupping my cock and balls and fitting snugly between my ass cheeks.
So, with trembling hands, I began to undress, unbuttoning my shirt and unbuckling my belt, taking off each item of clothing and folding them in turn, placing the toilet seat. And then, when I was totally nude, I once again got dressed in my brand new feminine outfit – panties, bra, stockings, skirt and blouse.
But as soon as I’d finished dressing, I had no time to even enjoy the feel of my new outfit, because I quickly began to hear noises in the office – the soft murmur of voices – and a fresh pang of worry flashed through me. I checked the time on my cell phone. It was almost nine o’ clock. By now the main office would be full of people, and was I really about to walk out there, dressed like this? I could just picture those two macho guys looking at me in total disgust, laughing and whispering about me, and while I wanted to please my cruel Mistress, I just didn’t know whether I could go through with it.
With a worried sigh, I sat down on the toilet, wondering what the hell I was going to do. A part of me even considered just dressing again in my regular Peter clothes, marching into Mistress Cartwright’s office, and announcing that I just couldn’t do it. That she would have to fire me.
Just then I heard the door to the washroom open and the click of heels, and my stomach twisted up with worry and fear. I stayed totally still, my heart pounding, as the clicking of the heels came closer and closer.
“Hello? Someone in there?” the kindly voice came, and I realized who it was: Becky, the receptionist.
“Um, just a minute,” I called back, in the highest, most feminine-sounding voice I could.
But even so, her immediate answer was, “Peter? Is that you?”
I sighed with despair, knowing there was no way of hiding what I was doing.
“Yeah, it’s me,” I said, in my regular voice.
“What are you doing in here?” she replied with a giggle. “You know this is the girls’ washroom, right?”
“I, uh, yeah, sorry,” I mumbled, unable to even think up a valid excuse.
“Well, anyway, hurry up in there, I need to pee!” she replied.
I took a deep breath, then stood up.
It was time. Time to show myself.
With a trembling hand, I reached out and opened the door ...
“Oh my god, wow,” Becky said, taking a step back and covering her mouth with her hands.
I couldn’t tell quite what she was thinking as she set her big blue eyes on me, but at least she wasn’t just outright laughing at me.
“You gave me quite a shock,” she said, looking me up and down.
“Sorry,” I mumbled, feeling my face radiating heat, my whole body and mind wracked with shame. “I just ...”
But it was no use. There seemed to be no way for me to explain the weird, crazy sequence of events that had brought me to this point; standing here in the women’s washrooms in front of the pretty receptionist, dressed in a skirt, blouse and heels. I was just glad she wasn’t screaming the place down.
“You’ve actually got a pretty good figure, you know,” she said, giving me an admiring nod. “But I think your makeup could use a little work!”
At this, I let out a laugh, despite myself; maybe simply out of relief at how nicely Becky was acting with me.
“I bet I look like a total freak,” I replied, sitting back down on the toilet and hanging my head in my hands.
“Hey, hey,” she said kindly, stepping forward and laying a hand on my shoulder. “You honestly don’t look that bad, Peter. I think it’s kinda cool that you’ve chosen to express yourself this way. I just think ... well, if you wanted, I could give you some makeup tips? Make your face look a little better to match your outfit?”
At this, I felt a rush of tenderness towards Becky. Why the hell was she being so nice? And I quickly leapt at the opportunity – anything to make me look even a little better.
“Thank you so much, Becky. That would be really awesome,” I said.
“Okay, you wait there and I’ll be right back! Actually, do you mind if I use the toilet first?”
“Uh, sure,” I said, pulling myself up off the seat and making way for Becky to step inside the stall with me.
And maybe it was because of the nervous, worried look on my face that she said, “It’s okay, you can stay in here with me while I pee!” like it was the most normal, natural thing to do.
I averted my eyes as much as I could in the small stall as Becky pulled up her skirt, pushed down her panties (which looked bright purple from the very corner of my eye), and sat happily down on the seat and began to pee loudly.
“So how long have you been dressing like this?” she asked as she peed.
“Uh, not very long,” I mumbled.
“And what do I call you? Do you want me to just say Peter or ... do you have a different name now?”
In a split second, before I’d even thought about what I was saying, the name had leapt from my lips. “Penny,” I said, my voice shaking a little. “I’m called Penny.”
“What a pretty name,” Becky said, smiling up at me. “Oops!” she added with a giggle, as her peeing came to an end and she let out the tiniest little fart. “Okay, so you wait in here for me, Penny, and I’ll be right back to fix you up real good,” she said, as she got up and flushed the toilet.
Then she raced out of the stall and into the office, leaving me there, once more sat on the seat, head spinning, wondering what the hell was even happening.
Where the hell had Penny come from? I thought to myself, shaking my head, as I waited for Becky to return.
* * *
“Okay, hold still, we’re almost done,” Becky said a few minutes later, as she bent over me, brushing something against my eyelashes. She’d already applied some sort of cream to my face, as well as what I assumed was blusher, eyeliner, and either lipstick or lip gloss, but I was still to actually see the results of this last minute makeover, so for the moment I could only guess.
“There,” she said, taking a step back then nodding happily as she assessed her work. “And I have to say, that’s a pretty damn good job – if I do say so myself!”
With that she pushed open the door to the stall then beckoned me to come out too, so that I could take a look at myself in the large mirrors by the faucets.
So I pushed myself up to my feet again and took a few nervous, wobbling steps towards the mirror, my heels clicking loudly in the silence of the bathroom. And when I finally caught a glimpse of myself, I took in a sharp involuntary breath.
“Oh my god,” I said, quietly. “Becky, that’s amazing.”
“Thank you, sweetie,” she smiled happily, standing just behind me, both of us now looking at my reflection in the mirror.
It was true – she’d done wonders. Whatever magic she’d spun with that makeup bag of hers had transformed me into ... well, into a girl. It was so crazy. I mean, I knew it was me, but the person staring back at me looked totally unfamiliar. Like some cute cousin or sister of myself. She’d used powder to accentuate my cheekbones and the lipstick really brought out the plumpness of my lips – a feature I’d never really noticed before. And the eyeliner and mascara actually made my brown eyes look really big and cute, kind of cartoonish even. Even my shaggy hair now made sense; with my girly makeup, it looked like some sexy pixie cut.
I stared in total disbelief. If I’d seen this girl walking down the street, I would have totally wanted to bone her. But the girl in the mirror was me.
“Oh shit, look at the time,” Becky said, glancing down at her watch. “We’d both better get to work!”
She raced towards the door that led back to the main office, then paused, holding it open for me.
“Come on,” she said, giving me a reassuring smile. “You can’t hide in there forever!”
I took a big gulp then nodded. It was time. Time to show myself. Time to become Penny ...
As I pushed open the door to
the office, it felt like every eye in the room turned to stare at me. Maybe I was imagining it, but in that moment, I felt so utterly acutely aware of the fact that here I was – stepping out into the office dressed in make up, women’s clothes and high heels. As I walked, I tried my best to stay steady on my feet, tried to keep my back straight, my head up, my shoulders back – to project confidence even if deep down I felt totally embarrassed and humiliated. With each step I took, I willed myself not to trip over, and by some magic it worked. And what’s even better, it seemed as if, after that first glance in my direction, the majority of the staff actually turned back to their computers and got to work, obviously just thinking I was some girl they’d never seen before, perhaps another new starter.
In fact, the only eyes that were still trained on me now belonged to those gross macho guys I’d heard talking in the men’s bathrooms about Becky just a couple days ago, and the way they were looking at me, there was no doubt they thought I was a genuine chick.
It felt so strange, so unreal. As I walked, I expected their faces to wrinkle up in disgust at any moment, when they figured out who I was. But no. Instead all I could feel was sheer animal lust radiating from them as their eyes followed me as I walked in the direction of the corridor that led to Mistress Cartwright’s office.
And as I passed Becky’s desk on the way, she shot me a friendly smile and a little wink as if to say, Our little secret.
Standing outside Mistress Cartwright’s door, I reached out and knocked.
There was a pause, then her familiar cruel voice: “If that’s Peter, you’re fifteen minutes late.”
I pushed open the door and stepped inside, hanging my head as I said, “I’m so sorry, Mistress. It just took me a little longer than I’d planned to get ready.”
I kept my head hung low as I waited for her to speak and when she finally did, I could tell something had changed – that perhaps I had surprised her by my appearance. Perhaps she’d simply expected me to look the same as before, messy and unkempt, only in women’s clothing as opposed to men. I had to admit, it had certainly taken me by surprise just how good I looked in my new outfit – and Becky’s amazing makeup skills, of course.
