by D. L. Savage
“Oh come on,” she hissed, laughing cruelly at me, “a horny little slut like you? I thought you’d be begging for more! You’ve only sucked nineteen cocks, Penny. There’s still five more to go before you’ve paid off your debt ...”
I couldn’t help it. I began to sob, my body shaking softly, my mind at breaking point. Sure, it had been fun – I had enjoyed myself, up to a point, but it seemed like even a sissy slut like me had her limits.
I took a deep breath, my heart pounding, as I realized I was going to have to face up to my cruel mistress, to tell her that I had to stop now, and if that meant I lost my job, then so be it. She could take out the remaining five hundred dollars from my wages ...
But before I could speak, there came a knock at the door, and we both turned around, startled.
“Yes?” Mistress Cartwright said, puzzled. “Who’s there?”
“It’s me, Becky,” came the gentle reply. “May I come in?”
Mistress Cartwright rolled her eyes, as if to say what now, but replied, “If you must ...”
The door opened and in walked Becky, looking just and fresh and pretty as she always did, her beautiful blonde hair tied up in a neat ponytail and her slim body shown off perfectly by her cute-but-sensible white blouse and smart grey skit.
“I hope you don’t mind,” she said with a shy smile, “but I kinda heard what was going on down here and, well, I think I’d like to help. I’ve had Dawn cover on reception ...”
“Help?” Mistress Cartwright interrupted in total disbelief. “Why on earth would you want to help?”
“Well,” Becky continued, “I think it’s partly my fault that Penny’s down here in the first place. You see, it was me that took her out on that shopping spree – so if anyone should be punished for spending all that money, I think I should be the one.”
As Mistress Cartwright looked over at me, from behind her shoulder Becky shot me a cheeky little wink, then quickly made her face serious again.
“If that really is the case, then yes, I suppose you should also be held accountable,” Mistress Cartwright said quietly.
Just then, all three of us fell silent – at the sound of the door to the basement opening and closing, and what sounded like two guys approaching the cubicle, laughing and muttering amongst themselves. I recognized those voices – it was the two bro dudes from the office. Becky rubbed her hands together with glee and quickly got down on her knees in front of the glory hole, while Mistress and I watched on.
“You go first dude, this is probably some hoax,” the first murmured.
“No you go, bro, what if it’s a dude back there!”
Then, to my surprise, Becky spoke in a sexy voice, “Your loss, gentlemen ...”
At that, there was a scramble, and soon a thick white fleshy cock flopped through the hole. With total relish, Becky fell on it, stuffing it quickly into her mouth and sucking on it like her life depended on it, working it up to full hardness in a matter of seconds, her lips sliding up and down the glistening shaft while she pumped it in her fist too, her eyes closed and soft little groaning sounds coming from the back of her throat. Her groans got louder as she sucked at a steady rhythm, and then with a sudden muffled whimper, I was sure she’d started cumming, her body quaking and shuddering as she continued to suck like her life depended on it.
All of a sudden, we all heard a low groan from behind the wall, and then watched in awe as the cock started pumping and pulsing, while Becky kept her lips wrapped tight around it. Finally, she pulled it from her mouth with a pop, then opened her lips to show us both the fresh white load sitting on her tongue, before swallowing it all in a loud gulp, then licking her lips and smiling happily.
“Well I never,” Mistress Cartwright whispered coldly, shaking her head. “You are rather good at that, aren’t you?”
“Sure am!” Becky grinned back proudly. “It’s my favorite thing in the world.”
And what’s more, even though just a moment ago I’d been complaining and pleading to Mistress that I was exhausted, watching Becky suck so eagerly on that big hard cock had ... well, got me kind of horny again.
“Dude that was awesome, you won’t regret it,” one of the guys said outside, and a moment later, another cock came sliding through the hole and Becky got to work on it. And this time, as I watched her, well, I couldn’t quite help myself. Before I even knew what I was doing, I’d joined her, reaching out to toy with its big swollen balls while she continued to suck.
“Good god, Penny,” Mistress Cartwright sighed, “You really can’t get enough, can you?”
And this time, when Becky got the second to blow his load – again in record time – she turned and kissed me, our tongues flicking as we passed his creamy, salty load back and forth, while those guys ambled back to the office.
And that was how we finished the day – Becky and I both sucking away on the last few mystery cocks, watched over by Mistress Cartwright, until finally at around five o’ clock, we hit our target.
“Very good girls,” Mistress Cartwright admitted. “I suppose you can go now.”
“Whew!” giggled Becky, mopping at her brow with the back of her hand. “That sure is thirsty work! You wanna come for a drink, Penny?”
And I was about to say yes, when I remembered Alex – back at the apartment, and I felt this weird flash of ... well, excitement, I guess. Crazy, isn’t it? In all that time we’d lived together as guys, I’d never considered him anything other than a friend, never looked twice at him. But now, as Penny ... it was quickly turning into something more.
“Anyone home?” I called out as I stepped back into the apartment. But again, I found I was alone. I couldn’t help feeling a little sad; I’d been looking forward to seeing Alex again. But at the same time, I was kinda relieved that at least I’d have a little time to get ready and freshen up before he got home. After all, a quick look in the mirror told me I’d certainly looked better.
My hair was all mussed up, my eye makeup was running in streaks down my face and I if I looked closely, my silk blouse was dotted with dried cum – not to mention my totally drenched panties, too. Yeah, time to clean up!
So I headed through to my room and quickly set about picking out a new outfit – a cute pink mini dress, and matching underwear, with white stockings and white heels, too. As I laid out the girly items on my bed, I felt a shiver of anticipation and excitement about how I’d look in this sexy new getup, but first ... a shower.
I slipped out of my dirty clothes, and reluctantly pulled off my wig, feeling pathetic and ashamed as I transformed once more into scrawny ugly Peter. It was so strange, turning back into my old self felt so wrong now, so weird and unnatural, and I longed to be Penny once more.
I quickly wrapped a towel around myself and scooted to the bathroom, closing the door behind me and turning on the shower, glad to be under the hot water, soaping my body – which was still freshly shaved and waxed. As I ran my hands over my chest, I longed for real breasts, and my mind even started to turn toward the subject of real implants, instead of simply padding my bra. Yes, I would get a pair of titties of my very own – small but pert and cute – and I’d even start looking into hormone replacement therapy, too, just as soon as I got paid.
As these new thoughts swam through my head, I felt a growing excitement in my tummy, as I realized that I really could be Penny all the time ...
I jumped out of the shower and towelled off, eager to get back to my room to start searching for more information about my new plan on my laptop. But as I pushed open the door, I saw something I wasn’t expecting. Because there was Alex, once again settled on the couch. He turned to look up at me, the smile dropping from his face when he saw me.
“Oh ... hey,” he said, puzzled. “I thought you were ... Wait, what happened to Penny. Has she gone home already?”
“Oh, um, yeah,” I stammered, heart pounding, face flushing with heat, hoping to god that Alex didn’t figure it all out.
“That’s too bad,”
he said with a sigh. “She was pretty cute.”
“Oh really,” I said, forcing a laugh. “I thought you two might hit it off.”
“So, do you have her number?” he added hopefully.
“Yeah, sure, I’ll go grab it for you once I’m dressed,” I said quietly, quickly turning and heading back to the safety of my room, slamming the door behind me.
Wow, that was a close shave, I thought, sinking down onto my bed, my heart still drumming and all sorts of mixed emotions running through me. A part of me was relieved that I hadn’t been caught, while another part was ... well, annoyed that the fun was over. I would have loved to spend another night with Alex, dressed as Penny – to maybe take things even further.
I guessed I could give him a fake number or something – maybe buy a second cellphone, and then arrange a date with him somewhere. But no, the whole thing seemed so risky now – if I kept it up, I would surely be caught out sooner or later.
With a frustrated sigh, I pushed myself back up to my feet and began folding away the cute pink outfit I’d picked out to surprise him with, my mood sinking lower and lower. But all of a sudden, I stopped stock still.
My hands began to tremble, as I slowly shrugged off the towel, then began to pull on first the panties, then the bra, then the stockings, and then that sexy pink, figure-hugging dress. Next I took the wig cap and carefully placed it back over my hair, tucking away any loose strands, before once again pulling on that gorgeous black wig.
And then I did my makeup, just the way Becky had shown me – slowly and carefully applying the foundation, eye shadow and eyeliner, blusher, lipstick, and lip liner.
I took a step back to take in my full reflection in the mirror, and a wave of excitement flashed through me.
Penny was back!
Here goes nothing, I thought, as I turned and pushed open the door to my room ...
“Hi Alex!” I said, in my softest most feminine voice. “I’m back.”
I watched as he span around on the couch in surprise, his mouth dropping open and the XBox controller falling from his hands as he set eyes on me.
“What the fuck?” he murmured. “I ... I don’t understand.”
“I think you do,” I said softly, my eyes locking onto his.
“Oh my god,” he said slowly, his eyes widening. “No, dude. Is that ... Is that you?”
I nodded my head, my whole body trembling. It felt good to finally tell him the truth, to finally own up, because I knew in that moment that I wasn’t ever going to be Peter again, and one by one, I would have to go through this experience with everyone in my life: telling them about the new me. So who better to start with than my best friend?
But at the same time, I felt scared too. After all, I’d deceived him, hadn’t I? I’d tricked him into thinking I was someone else ... Hell, I’d sucked his dick. He had every right to hate me now, to tell me to fuck off out of his life forever.
“But we ...” he stammered. “You ...”
“That’s right, Alex,” I said softly. “I remember exactly what we did. And I understand if you never want to speak to me again because of it. This is all so crazy for me, too. I don’t even really know what’s happening. All I know is, I’m Penny now. And that’s how I’m going to stay. From this moment on. I’m so sorry if you feel I tricked you, but that was never my intention. It just happened so naturally ...”
I could hear my voice trembling as I spoke, and I had no idea how Alex was taking all this. His eyes stayed fixed on mine and his face didn’t give away any trace of emotion. But I knew I needed to just say everything – to confess every damn thing I’d been thinking and feeling since this whole crazy ride started.
“The thing is, Alex, this has been pretty weird for me, too,” I continued softly. “I only started changing recently, and up until then I didn’t think of you as anything but a friend, I promise. But now .... Well, now I guess I could say I have feelings for you.”
I stopped again, wondering if I’d gone to far. But no, I needed to say this, if only for my own sanity.
“If you don’t feel the same way, that’s totally fine. But I want you to understand. I’m Penny now. Always will be. I want to make these changes permanent.”
There was a long pause, and I wondered if Alex would even say another word to me. It felt like forever before he finally spoke.
“Wow, that’s a lot to take in,” he muttered, shaking his head.
“Sure is,” I replied, my whole body shaking. “For me too. Anyway, I’ll be in my room. I don’t want to make you feel any more uncomfortable than you already are ...”
I turned to leave, but then I heard his voice behind me.
“Penny, wait.”
I span back to face him, my heart leaping at the simple fact that he’d used my new feminine name. He was actually taking this seriously!
“Okay, I’ve thought about it,” he continued shyly, not quite meeting my eye now, “and ... well, I think I have feelings for you, too.”
A small smile tugged at the corners of my mouth as he spoke. Was this really happening? Because this was a way better outcome that I could have ever imagined.
“Let’s just take things slow, and see what happens?” he continued. “Does that sound okay to you?”
“That sounds amazing,” I gushed, still unable to believe my ears. “Mind if I sit down?”
“Sure,” he smiled, patting the empty seat on the couch next to him.
As I strode over, I could feel it again – that crazy tension between us, just like last time. He was checking me out, I was sure of it. I could feel his eyes moving over my slim petite body. And as I sat down next to him on the couch, I felt so small, so feminine, compared to his strong masculine frame.
“I really like you, Alex,” I said, turning to face him, my eyes locking onto his.
“I really like you too, Penny,” he replied in barely more than a whisper. “I haven’t been able to stop thinking about you, if you want to know the truth.”
“Same here,” I whispered back, leaning in a little towards him.
Alex leant in too, and I closed my eyes, my body shivering with anticipation. And as our lips met in a tender kiss, I felt a powerful wave of emotion flow through me. This felt so good, so right. And quickly the kiss got hotter, his hands moving into my hair, and my own starting to explore his manly body, my fingers grazing over the bare skin of his arms, then tugging at his t-shirt – as if with a mind of their own.
He broke the kiss just long enough to pull off his shirt, uncovering his upper body, and then once again we were kissing madly on the couch, our bodies pushing into each other hard now, both of us getting more and more turned on and breathless with each passing second.
I sighed softly as Alex started to run his hands up and down my body too, his fingers tugging my dress eagerly further and further up my thighs, uncovering the cute pink thong beneath, containing the small yet aching bulge of my sissy prick.
“Wait,” I gasped, my hand moving to his wrist to stop him.
“What is it?” he murmured, his voice tight with lust now, his eyes blazing at me, clearly only one thing on his mind.
“I feel shy,” I admitted, scared that if I showed off too much of my body to him he might suddenly get turned off – after all, while I looked like a girl, my bra was still padded (for now) and I wanted to stay dressed up and girly for him, at least until I’d made some more permanent changes to my physique.
“Sorry, sure,” he murmured, “I don’t want to do anything you’re not comfortable with ...”
“Thanks,” I smiled back, feeling glad all over again that he was so totally understanding. “And don’t get me wrong, Alex. I want this, I really do. But can we take things slowly, at least for now?”
“Of course,” he smiled back. “So ... what do you want to do?”
And then I felt another powerful wave of excitement rush through me, as I decided to say exactly what I wanted from this experience.
“Well, what I want
,” I began shyly, “is to do everything. With you. Right now. But I just want to keep my clothes on. Does that make sense?”
“Sure, baby,” he smiled back, his hand brushing my cheek, his eyes still burning at me. “You just lead the way.”
Oh god, it all felt so perfect – like a dream. The way he’d called me baby, told me he was really taking this seriously – he really did think of me as a cute, sexy girl. My whole body was trembling with anticipation as I pushed back into him in a hungry kiss, my hands this time moving to his belt, eager to unbuckle it again, to once more be stroking and sucking on that gorgeous dick of his.
He quickly helped me in my mission, fumbling open his pants, and when my eager fingers finally wrapped around him, I realized with excitement that he was already totally hard for me – hot and hard and throbbing.
I fell to my knees, eagerly taking him in my mouth with a breathy sigh, and oh my god, it was like heaven. I felt like I was finally exactly where I wanted to be: a sissy slut, on her knees, sucking cock like her life depended on it, while her own little dick throbbed with pleasure without her even touching it!
But after only a little while, I felt his hands gently cup my head, drawing me away from his now-glistening dick.
“Hey,” he murmured with a shy smile, “you keep going like that and I’m not gonna last very long!”
“Sorry,” I grinned back, resting my hands on his knees as I pushed myself back to my feet, ready to carry out the next part of my naughty plan. “Maybe we could try something ... else. You have any, uh, condoms?”
At this his eyes widened, and he quickly nodded and fumbled around in the back pocket of his rumpled pants, pulling out his wallet and opening it.
I watched him as he quickly took out a roll of condoms and tore one open, then slid it over his still rock-hard cock. “I thought you wanted to take things slow,” he grinned, as I watched him fitting the condom carefully down over his thick shaft.
“I changed my mind,” I replied in a naughty, girly giggle, batting my lashes at him, as I straddled him on the couch now, placing my hands on his shoulders to steady myself, my knees spread wide apart, either side of his muscular thighs, my dress hitching up around my waist, giving him a flash of the small bulge in my panties.
