by D. L. Savage
“Well,” she said eventually, “stand up straight so I can get a proper look at you.”
I did as she asked, lifting my head and once more pushing my shoulders back, sucking in my stomach, and making my back as straight as possible.
“My, my,” she said, pushing herself up from her desk and striding out into the middle of the room. “You’re actually rather a pretty little sissy, aren’t you, Peter? Or would you prefer me to call you by a more girly name from now on?”
I sucked in a deep breath then whispered, “Penny.”
“What’s that?” Mistress Cartwright hissed.
“I’d like to be called Penny from now on,” I repeated.
“Oh, is that right?” There was a mocking tone to her voice, and for a moment I wondered if I had perhaps gone too far. After all, she was the one calling the shots, not me. What right had a pathetic worm like me got to tell her what name to call me by?
But to my surprise she nodded and said, “Very well, Penny, if that’s what you’d like to be called from now on, then so be it. And I have to say, you’re looking a lot better than I’d expected.
“Thank you, Mistress,” I said quietly.
And then I waited as she slowly circled me, her own stiletto heels clicking, as she looked me up and down.
“Are you wearing the panties, too?” she asked.
“Yes, Mistress,” I replied.
“Very good, very good. Well, Penny, your first job of the morning is to fetch me an iced latte. Think you can handle that?”
“Yes, Mistress,” I said again, trying to fight back my nerves at the thought of actually going outside dressed like this. What if I bumped into someone I knew? What if some group of teenage boys saw through my outfit and started calling attention to me in the middle of the street? What if I simply tripped over in my heels?
“Well, get to it then,” she snapped, and I quickly turned and headed out of her office, breathing a sigh of relief as I closed the door behind me.
I glanced up the corridor to the reception desk, where Becky was just finishing up a phone call. As she was finishing, I walked over to her, slowly but steadily, one foot at a time. It felt like I was on stilts, and on top of that, I had to ignore the severe pain in my toes, which were all crushed together.
“Looking good,” Becky grinned when I reached her desk.
“Thanks,” I said, blushing a little, figuring she was probably just being kind. “Hey,” I added. “I’m just going out to get Miss Cartwright a coffee. You want anything?”
“Oh yeah, that’d be awesome actually,” Becky grinned back. “I’ll have a skinny macchiato please!”
“Sure thing,” I smiled, glad to have at least one friend in this place.
It was the strangest thing. From the moment she’d caught me in the washrooms, dressed in my girly clothes, it was like she’d totally opened up. I knew there was no way in hell she liked me like that. No this was something else. It was more the feeling of being in on something together – just us girls – and I realized in that moment that I’d always felt envious of the kinds of close, conspiratorial friendships that women seemed to have, but how here I was actually involved in one myself!
“I’ll be right back,” I grinned, and with a newfound confidence I turned and headed towards the elevators ....
Don’t trip, don’t trip, don’t trip, I repeated to myself as I strode down the busy street in the direction of the coffee shop. I was trying my hardest to walk the way I’d seen fashion models do: on foot in front of the other, back straight, shoulders back, and it seemed to be just about working. Apart from the pain in my toes, the rest of my body actually felt kind of good too.
I could taste the subtle sugary sweetness of the lipstick Becky had applied to my lips, and I could feel the strange snug tightness of my thong panties, and I could even feel the soft tingle of the air against the bare skin at the tops of my stockings, coming in through the bottom of my skirt.
I had almost reached the coffee shop when I heard a voice calling from somewhere behind or above me. “Hey baby!” the gruff male voice called.
For some reason I knew it was directed at me, and I turned around to see where it was coming from. There was a construction site on the opposite side of the block and there, in a line, were four dirty sweaty guys all leering back at me.
“Nice ass!” one called.
“You want a piece of this,” called another, grabbing his crotch in one hand and shaking it at me.
Without even thinking, I gave them the finger, then turned and strode off towards the coffee shop, the adrenaline pumping through my veins, every nerve in my body suddenly blazing bright. And the weirdest part about it was, even though there was no way in hell I would ever give those guys a second look, a little secret part of me had got kind of turned on at the idea – the idea that guys now found me hot. I’d spent my whole life as boring, invisible Peter, someone who never stood out from the crowd. But now, less than an hour in my new life as Penny, I’d had all sorts of attention.
As I entered the coffee shop, I was so busy thinking about these things that I wasn’t even paying attention to where I was going, and I stepped right into the path of a guy in a business suit who was just leaving the store with a whole tray of coffees.
There was a split second when I thought I would crash right into him, knocking boiling hot coffee everywhere, but luckily he stepped aside just in time.
“Close call,” he smiled at me.
“I’m so sorry,” I said in my smallest, most feminine voice, hoping to God he didn’t immediately recognize me as a guy.
As I looked up into his eyes, I felt something flash inside me and – wow – I actually found him kind of ... hot. Weird. He was tall and dark haired, with tanned skin and bright white teeth, and his black tailored suit showed off what I guessed was some body beneath.
“Don’t worry about it,” he smiled back at me.
I could smell his cologne – something spicy, no doubt expensive – and I could tell he was checking me out, just as much as I was him. For a half second I watched his eyes flit down towards my chest, and I made sure to suck in my tummy and ease back my shoulders, hoping my tiny ‘breasts’ would pass his inspection. Because the more I stood here, gazing up at this guy, the more hot I was getting. I could feel a tingling between my legs, and the swelling of my cock in my panties. I didn’t dare to glance down to check if there was any kind of bulge showing. I just held his burning gaze for a second longer than was normal, and said in my softest, sexiest voice, “Thank you for being so kind.”
Then before I totally blew it, I quickly turned and joined the short queue at the counter. As I waited to order my coffees, a little part of me felt disappointed that I’d not flirted even more with that guy. I found him attractive and he obviously felt the same way about me. But at the same time, I reminded myself that I wasn’t actually a girl – and what could really happen between us? No, it was just a little bit of fun and now it was over.
I ordered my coffees – iced latte and skinny macchiato – then picked up the cups and strode out of the store, turning and beginning the short walk back towards the office, wondering if those asshole construction workers would shout anything this time.
Sure enough, I heard a voice calling from behind me: “Miss? Miss?” and I span around, ready to give whoever it was a piece of my mind.
But to my surprise, this was no construction worker. No, this was the guy, the guy from the coffee shop, racing to catch me up.
What the hell?
“Um, hi,” he said when he’d reached me. “My name’s Marcus.”
“I’m Penny,” I said softly, wondering just where this exchange was going.
He was obviously somewhat confident – and I’m guessing this wasn’t the first time he’d pursued a girl he’d just met – but at the same time there was a disarming sweetness about him too, something warm and genuine.
“Listen,” he said, locking eyes with me, “I’ll cut to the chase. I’m
new to this city and I don’t really know that many people – that many girls – and, well, I was wondering if perhaps you’d like to go out for a drink with me sometime?”
I felt my mouth curling into a smile and it seemed like the decision had been made before I even opened my mouth.
“I’d like that,” I said, my heart pounding, as I stared into his handsome face.
What the hell am I doing?! I thought.
“Great,” he replied, holding his tray of coffees in one hand in order to reach into the pocket of his blazer and pull something out.
He handed it to me. It was a business card.
“That has my cell phone number on it,” he explained.
“Thanks, Marcus,” I said, hearing a strange sexiness entering my voice, almost like I was turning into somebody else. “I’ll give you a call sometime.”
And then, before I could somehow mess this encounter, I quickly turned and walked away, back towards the office, my cock tingling in my panties, my heart beating hard, my whole body pumping with adrenaline at what had just happened.
You know what? Perhaps, I could get used to this after all, I thought to myself with a naughty little smile.
“Thank you so much!” Becky said as I set the coffee down in front of her.
“No, thank you,” I smiled back. “I really appreciate everything you did for me this morning.”
“Don’t mention it,” she grinned. “So, I take it you’ve been enjoying your new look?” she added, once again dropping her voice to a conspiratorial whisper. “Any guys been checking you out?”
“Actually?” I giggled shyly, totally falling into the role of a gossiping girl. “I kinda got asked out on a date just now.”
“No way! That’s awesome!” Becky replied, her eyes lighting up. “So what did you say? Was he hot? Are you gonna meet him?”
I shrugged. “I don’t know. I mean, yeah, he was hot. But wouldn’t he freak out ... you know. If he found out?”
“Who says he has to!” Becky laughed. “There are plenty of ways to keep your little secret under wraps. Hey, why don’t you come back to my apartment this evening? I could help you out, show you a few makeup tips, maybe help you choose a few more outfits? That is, unless you’re busy?”
“No!” I gushed. “That would be amazing!”
And I was about to thank her again, when our conversation was interrupted by the icy cold tone of Mistress Cartwright, coming from her nearby office.
“Penny?”
“Oh god, she must have heard me gossiping,” I said, my heart suddenly pounding in my chest at the thought of once more displeasing my cruel mistress.
“See you later, girlfriend,” Becky whispered with a wink, picking up her coffee and taking a sip as I quickly grabbed the other cup, Mistress Cartwright’s iced latte, hoping to God that I hadn’t messed up her order this time around.
I headed over to the office and pushed open the door.
“Get in here, and close that door behind you,” she growled.
“Yes, Mistress,” I said, doing just as she said, as the now familiar cold tingles of anticipation and fear rushed around my body.
“Is that my coffee?” she said, nodding at the drink in my hand.
“Yes, Mistress, sorry, Mistress,” I said, quickly placing it on her desk then resuming my place in the middle of the room.
“So tell me, Penny,” she continued, “what exactly where you chattering away about out there with Becky? Seemed like you two were giggling about something ...”
I felt my cheeks beginning to radiate with heat, and I wondered what I could possibly say. I didn’t want to lie – I knew Mistress Cartwright would know in an instant.
“Just ... boys, I guess,” I mumbled, my face burning with heat.
“Oh, boys, eh?” she laughed, her voice loud and piercing. “Boys who get your cute little sissy panties wet. Is that right?”
I nodded, staying silent.
“Pull up your skirt,” she commanded, and I quickly did as she said, reaching down and pulling my skirt up around my waist, exposing my panties. “I want to check for myself ...”
Quick as a flash, she strode towards me, until her face was right in line with mine. A second later, I gasped as I felt her hand slip right inside my thong, the coolness of her fingers cupping my cock and balls for a moment before pulling away again. She lifted her fingers to her face to inspect them, and sure enough the tips were covered in a thin sheen of pre-cum.
“So you are,” she said with a cruel smile. “Well, go on then. Lick your pussy juices off my fingers.”
I parted my lips and bent my head down towards her hand, gasping as she pushed her fingers into my mouth. I sucked and licked them as clean as I could, as Mistress Cartwright cackled with pleasure.
“Very good, very good indeed!” she laughed. “You really are a naughty little sissy!”
She was speaking so loud I was afraid the whole office might hear her, and my face burned even hotter with shame.
“Okay, that will be all, for now,” she continued, suddenly in a much more normal voice, like we’d been discussing some totally normal business matter. “If you head to the main office and find a spare desk, you can get started on these.”
And with that, she handed me the hugest pile of forms and printouts.
“I need them all typed up onto the system,” she smiled sweetly, no hint of her menace of just a few moments ago. “But there’s no hurry. Just a little thing to keep you busy.”
“Thank you, Mistress,” I said, quickly taking the huge stack of papers from her and heading back out of her office, the sweetly salty taste of my own pre-cum still strong in my mouth.
After all the craziness of the last few hours and days, I was actually kind of glad to just sit at an empty desk – nestled away in the far corner of the busy office – and actually lose myself in some work. Okay, so it was boring as hell, but even so, I think I just needed something mindless like that to help me relax. And the weirdest part of it all was that I was doing this work dressed as a woman and yet it felt so natural. Every now and again I’d realize all over again and marvel at the strange situation I found myself in.
Also, there were those two guys – those macho assholes, whose names I still didn’t even know, both giving me little smiles and winks whenever I so much as glanced in their direction. They were obviously just bored as hell and looking for any excuse to take their minds off their work. And to tell you the truth, a tiny part of me even enjoyed their attention – the way it made me feel. Sexy. Womanly. Happy.
Okay, so it was only my first day, but even so, crazy as it sounds, I felt more content in these few hours I’d spent as Penny than a whole lifetime trapped in the body of boring, plain old Peter.
I worked hard all through lunch and into the afternoon, and before I even knew it the people around me were finishing up at their desks and getting up to leave. I shot a glance at the clock. 5:30pm, the end of my working day.
As I got up to head out of the office, I noticed that Becky was waiting for me, standing by the reception desk, smiling.
“Hey you,” she said, as I reached her. And to my surprise she took my arm as we both walked on towards the elevators. “Are you still coming over to mine this evening?” she asked.
“That’d be great,” I smiled back.
“Awesome,” she grinned. “I think we’re going to have a lot of fun!”
* * *
Becky was so right. After a crash course in makeup and a few handy tips on how to walk confidently in heels, we moved onto clothes.
“No way, we’re the same size!” Becky exclaimed, as I fitted perfectly into a cute little purple dress she’d pulled out of her closet.
It was true. It seemed that Becky’s clothes fitted me perfectly. And she said I was welcome to borrow anything I liked – which I quickly took her up on, mainly so that I could have a few different outfits to wear into work.
“And I’d love to come shopping with you sometime, too,” she
grinned. “Maybe this weekend even?”
I grinned and nodded, full of happiness and contentment. I felt so at home here – here in Becky’s bedroom, sitting on the edge of her comfy bed, surrounded by all her colorful clothes and shoes.
“So Penny,” she continued, after taking a sip of her wine, “I still think it’s so cool that you’ve decided to express yourself this way. If you don’t mind me asking, how long exactly have you been ... uh ... transitioning?”
For a moment I didn’t know what to say. A part of me wanted to tell her the truth – that I had only even come to work dressed in women’s clothes because Mistress Cartwright had threatened to fire me, but then another part of me knew that if I told her that, she’d be disappointed, maybe even mad that I’d pretended to be more of a full-blown trans girl than I really was.
“Oh, I don’t know,” I said in the end, hiding my face a little, hoping it looked more like I was blushing than just ashamed of lying to her, “I guess I’ve always known I was kinda different ... But as for actually taking the first step and dressing up, today was it.”
“Wow,” she grinned. “I think that’s really brave. I mean, to actually come into work dressed that way. I think that’s amazing.”
“Thank you,” I replied, feeling a small sense of pride. She did have something of a point. It was pretty brave of me.
“So is this you now? Are you going to stay like this? As Penny?”
I picked up my own wine glass which was by my feet and lifted it to my lips, taking a small sip and savoring the cool crisp taste of the white wine, as I turned the idea over in my head. I certainly did have more fun as Penny. But to actually live like this from now on? Could I really do that?
“Maybe,” I replied, eventually. “But if I did, I’d need some help. I mean, I still have no clue about so many things. Would you help me, Becky?”
