by D. L. Savage
As he came prowling towards me, his big brown eyes locking onto mine for a moment, I felt myself tightening up with anticipation, my heart beginning to boom, as I realized that if I didn’t give in to my urges now, I’d regret it forever. He was just so gorgeous – and this was the perfect opportunity. I just had to let go.
As he shook his hips, his cock swinging towards me, he shot me a playful wink, as if daring me to give in to my most private desires, and before I even knew what I was doing, sure enough I’d fallen to my knees in front of him, my trembling hands running over the toned flesh of his body, then curling around the hot thick shaft of his swelling cock as I guided it towards my mouth.
A cheer erupted from the crowd as I closed my glossy lips around his cock, giving in to my desires, feeling him swell in my mouth, the heavy heat of him on my tingling tongue, as I began to bob my head in time to the beat, feeling my own cock growing hard and hot in my panties.
I closed my eyes, shivering in ecstasy, as I began to slide my lips up and down his rock-hard shaft, savoring every second his cock was in my mouth, his hands cupping my face and holding it in place as he began to fuck me like that, each thrust of his hips causing my own sissy cock to tingle and twitch too, even though I wasn’t even touching it. I groaned as much as I was able, knowing that if he kept on fucking my face like this, I was gonna cream my panties, right here in front of Candy and Jenny and all the other sissies!
Just then I felt a second set of hands, taking my hair and holding it away from my face in a ponytail. I opened my eyes to see who they belonged to, and there was Jenny, knelt down right next to me, that sexy naughty expression on her pretty face.
“Hey, let me have a little taste of that!” she whispered, her voice trembling a little, and with a final sigh I pulled the slick wet cock free from my glossy lips with a pop and offered it to Jenny.
A moment later her lips were wrapped around it, and she was sucking madly. I reached out to hold back her hair, just like she’d done for me, and it felt so slutty to be knelt there next to her, watching her suck, my own cock throbbing madly in my panties, ready to spurt at any second.
“Having fun, ladies?” Candy’s voice whispered in my ear.
I looked over my shoulder and there she was, watching us with glee.
“Say, Hailey, you look like you need something to fill those pretty lips,” she added, as Jenny moaned and sucked away right next to me. “Am I right?”
I nodded shyly. It was true; I’d give just about anything to have another cock to suck on.
“Well, today might just be your lucky day,” she purred, taking another step towards me, so my head was level with her waist. I watched in surprise as she began tugging her black skirt right up around her thighs, uncovering a pair of silky black panties beneath. She hooked a glossy nail beneath the elastic at one side of her crotch and tugged the panties open, and I gasped in shock.
I don’t know why, but I’d always assumed Candy was a woman. But to my total surprise – and delight – I realized she was a sissy, just like me. And a rather well-endowed one at that. There before me was Candy’s bright pink, juicy-looking cock, a set of cute, low-slung balls hanging beneath it.
She sighed with pleasure as I began to stroke it, watching with delight as it grew bigger in my fingers, and as it swelled and hardened, I realized it was a slightly different shape – curved downwards, with a bright pink head that I just had to feel in my mouth.
As I closed my eyes and guided Candy’s cock towards my open mouth, I could feel my heart beating hard, my whole body shivering with pleasure as I felt her hot thickness finally push between my lips. I groaned as I began to suck her, trying to hold off my own orgasm as long as I could, but with each bob of my head, I felt my own little sissy cock twitching and aching, ready to explode any second.
“God, that’s good,” Candy moaned, as I slid my lips up and down her shaft, and I felt her cock growing even harder in my mouth, swelling against my tongue.
With a muffled moan, I couldn’t hold off any longer. My whole body shivered as I let go, feeling my cock start to cum in my panties, flooding them with hot sticky warmth as I continued to work on Candy’s thick curving cock, sucking and moaning, stroking it with both hands, my chin wet with saliva and my own little sissy dick still twitching in my soaked wet thong, all hot and slick with my sissy cum.
But even though I was shivering from my own orgasm, I knew I had to keep sucking on Candy’s delicious cock. I could tell that she was getting close too, the way she was pumping away my mouth, not to mention how damn hard her cock felt. I kept on sucking, excited to taste her cum, stroking her shaft and teasing the underside of her cock head with my tongue, and all of a sudden she gasped, her body tensing and the head of her pretty cock swelling in my mouth for a moment, before I felt the first in a series of surprisingly powerful jets of fresh hot cum, pumping right into the back of my throat. I swallowed and swallowed, but Candy just kept on cumming, filling up my mouth so much that a little even spilled past my lips and dribbled down my chin.
Just then, to my left, I heard Jenny make a muffled groan and I looked over to see that the sexy stripper was coming in her mouth, too. She kept her lips clamped tight around his pulsing shaft, but I could tell by the way her eyes widened that he must be giving her a pretty huge load.
As soon as he’d finished, I knew I just had to kiss her. My own mouth was still full of Candy’s cum, and I drew Jenny’s sweaty face towards mine, our tongues flicking together in a sexy kiss, as we passed our creamy treats back and forth, the fresh cum smeared on our lips and dripping from our chins.
“I love you, baby,” I said, smiling happily.
“I love you too!” she giggled back, before pulling me towards her in another delicious kiss.
* * *
“That was so much fun!” Jenny giggled a little while later, as the party was finally winding to a close.
“Glad you girls had a good time,” Candy laughed, catching my eye for a moment and giving me a knowing wink.
“It was wonderful, thank you,” I said, but suddenly feeling a pang of sadness.
Jenny must have been able to sense this change in me, too, because she took my hand and gently said, “Hey, what’s wrong?”
“I guess I just wish I could stay like this a while longer,” I explained, gesturing down to my slutty little outfit, knowing that soon I’d just be regular old Henry again, dressed in boring, ill-fitting jeans and a t-shirt.
“Well, why don’t you?” Jenny asked, a puzzled look on her face.
“Sure, sweetie,” Candy said, putting her arm around my shoulders. “A lot of our clients will leave, still dressed up.”
“But, I mean ...” I stammered, as I realized that sure enough there was no reason why I couldn’t stay dressed in my sexy sissy outfit just a little while longer. After all, tomorrow was Sunday, wasn’t it?
“Okay then, I will!” I giggled happily.
* * *
So that night, Jenny and I drove home in our matching outfits and I didn’t even feel ashamed getting out of the car and walking back into our house. You see, I knew I looked so good that if any neighbors were watching, they wouldn’t even recognize that it was me.
I kicked off my heels and then fell into bed, happy and content, snuggling up to Jenny, glad to be able to enjoy my new girly self just a little while longer.
And as I drifted off into a deep contented sleep, I felt so glad to have someone to share this new exciting part of my life. Because I knew that my journey as a true sissy had only just begun.
3
She’s the Boss
“So, how do I look?” I asked, taking a step away from the mirror.
“Pretty good!” Alex laughed.
“Hey, what’s so funny?” I asked, honestly puzzled at his laughter.
“I guess I’ve just never seen you actually looking smart before,” he explained with a grin.
I turned back to the mirror to take another look at myself. I guess h
e did have a point. In all my twenty-one years, I’d only ever really worn scruffy jeans and sneakers, and now here I was dressed in a suit and tie. Okay, so what if the suit had cost me ten bucks from a thrift store? It was still a step up! I just hoped I looked good enough to get this damn job, otherwise I’d be asking Alex for another extension on the rent.
“So what time’s your interview again?” he said.
I glanced up at the clock on the wall and felt a sudden flash of panic.
“Oh shit,” I groaned.
“Let me guess. You’re late,” he chuckled. “Why doesn’t that surprise me?”
* * *
I arrived at the large office block around twenty minutes later, totally out of breath, face dripping with sweat, freshly washed shirt now rumpled and my tie flapping ridiculously over my left shoulder.
“Can I help you?” the receptionist asked, wrinkling her nose in what I hoped wasn’t disgust as she looked me up and down.
“I’m uh, I’m here for the interview,” I offered, once I’d finally caught my breath enough to speak.
“And your name is?”
“Peter,” I said. “Peter Smith.”
I winced inwardly a little as I said it. Just like everything else in my life, my name was totally dull and boring. Sometimes I even got to wondering how different my life might have turned out if I’d had a more interesting name. But even then, I suspected that things would just be kind of unremarkable for a guy like me. After all, it wasn’t only my name that was the problem. It was also my totally forgettable face, too, and my scrawny body and – if we’re being totally honest here – my below-average size dick.
I mean, sure I’d had a few casual relationships, but they never lasted very long, and I always got the feeling that girls were kind of underwhelmed by my gifts, or lack thereof.
“Okay Mr Smith,” the receptionist said, busting me out of my negative thoughts, “Miss Cartwright is already waiting for you. Her office is up on the seventeenth floor. The elevators are in the corner of the lobby over there.”
“Thanks,” I said, turning and walking towards the door to the elevators.
Miss Cartwright? I thought as I pushed the button and waited for the elevator to arrive. For some reason, when I’d applied for this job – a Personal Assistant position – I’d imagined that the head of Cartwright Inc. was going to be a guy. In fact, I’d been kind of surprised to even be offered an interview in the first place. I’d been frantically applying for work left, right and centre – just sending off email applications to anything at all that I could find on the net – but this was one of the few places that had actually got back in touch with me and offered me an interview.
I just hoped I was about to make a good impression.
Finally the elevator doors swished open and I stepped inside and punched the button for floor seventeen. As I zoomed upwards, I took a few deep breaths, hoping I would come across as calm and confident in the interview.
The elevator juddered to a halt a few moments later, the doors swishing open again to reveal a plush-looking corridor and a small reception desk.
I made my way nervously towards the desk, trying to ignore the pounding of my heart and the annoying trickles of sweat running down my back. I just felt so out of place and awkward in fancy corporate places like this. I hoped I didn’t look as pathetic as I felt.
“Hi,” I said to the cute, friendly looking young blonde girl at the desk, I’m here to see ... Miss Cartright?”
Just then I heard a voice behind me. “Peter?” it said in a cold, clear English accent.
I spun around to see who this mysterious person calling to me was, and when I finally set eyes on her, I felt a strange charge of excitement pulse right the way through me. Because whoever this woman was, she was stunning. I figured she must be a few years older than me – maybe late twenties – and everything about her was simply flawless; from her glossy black hair to her porcelain skin to her perfectly applied makeup to her sexy-as-hell, figure-hugging trouser suit, just as black as her hair and eyeliner.
“I’m Miss Cartright,” the woman announced sternly, in that striking English accent of hers, looking me up and down, a flicker of surprise or perhaps even disgust flashing across her beautiful features for a moment. “And you’re Peter, I assume?”
I tried to open my lips to speak, but by now I could feel all the moisture leaving my mouth, the words caught in my throat, and so instead I just ventured a timid little nod.
“Well if you’ll follow me to my office,” she said in that prim English accent – the kind of accent I’d only ever heard on TV shows before now.
And as she turned and strode off towards a door at the end of the corridor, I couldn’t help but check out her ass, shown off so perfectly by the tight black fabric of her suit pants. I felt my cock swelling a little as I watched her buttocks move as if teasing me, and my own walk was made somewhat awkward by my boner as I followed her into the interview room.
By the time I entered the room, Miss Cartwright had already taken the large leather chair that sat behind the desk. She watched me impassively as I made my way towards the seat opposite her – just a regular grey office chair. I could smell her perfume now, some kind of delicious spicy scent. And I swore that just for a half-second, her eyes flitted down towards the prominent bulge of my dick and her face wrinkled up in what looked like disgust.
“You were twenty-two minutes late, Peter,” she said, the moment my ass touched the seat of the chair.
“I’m sorry,” I replied quickly, not quite daring to meet her cold dark eyes, instead directing my gaze at the dark blue carpet between my feet.
“Are you usually late?” she continued.
“No, Ma’am,” I lied, hoping I sounded convincing.
“Miss Cartwright, Peter, please,” she shot back quickly. “Or if you prefer, you can call me Mistress.”
For a moment I thought she must be joking. I mean, who the hell asks to be called Mistress? But from the icy look on her face, I knew she was deadly serious. In fact, everything about this woman seemed deadly. And as she began asking me the usual questions – about my employment history, how I’d heard of the job, what I felt I could bring to the role – I found myself shrinking and sweating beneath her piercing gaze, my heart pounding, my mouth chattering on nervously, while I had no clue what I was saying or if it even made sense.
By the end of the interview, I was a total nervous wreck.
“Thank you for your time,” Miss Cartwright said, with a dismissive wave of her slender hand, “we’ll be in touch.”
And she stayed sitting behind her desk, not even looking at me, as I eased myself up out of my chair and let myself out of the room, my heart sinking as I realized that there was no way in hell she’d hire a worthless loser like me.
* * *
That evening, Alex tried to cheer me up by ordering us a large pizza – his treat. But I hardly felt hungry and I retired to my room after just a couple of slices, telling him I’d decided to grab an early night in order to start my job search all over again, bright and early the following morning.
As I set my cell phone to charge on the beside table then pulled off my rumpled thrift store suit and shirt, I felt my mind returning once more to Miss Cartwright. I’d never met anyone quite like her before. I mean sure, I’d seen hot businesswomen from a distance, but I’d never met one who was quite so mean – so openly dismissive of me. And what’s more, in a totally weird way, I kind of found her disgust hot too, even though it also made me feel completely worthless and pathetic.
Once I’d pulled off my interview clothes, I got into bed in just my boxer shorts and lay on my back, letting my mind drift back to that image of Miss Cartwright’s amazing ass in that tight black business suit she wore – her perfect buttocks moving so tantalizingly as she strutted confidently away from me down the corridor. Before I even knew what I was doing, my hand had slid into my boxers and my fingers had curled around my swelling cock as I began to stroke m
yself, imagining that it was Miss Cartwright jacking me off, her glossy lips curling in a crude mocking smile as she jacked my puny little dick with her long slender fingers. Pretty soon, I could feel the rush of my orgasm flashing up inside me, but just before it hit, the spell was broken by the annoying buzz of my cell phone.
What the hell?
With a sigh of frustration, I pulled my hand out of my boxers and reached out to take the call, registering from a quick glance at the screen that it was a private number calling.
Who could be calling me at this time of night? I thought, hesitating for a brief moment before I answered the call.
“Hello?” I said timidly.
“Peter,” Miss Cartwright’s cold voice shot back. “I’m just calling to let you know you have the position.”
“That’s uh, that’s amazing,” I croaked, totally shocked. “Wow, thank you.”
“I’ll see you in my office, nine o’clock, tomorrow morning,” she continued.
And then, before I could even say anything else, I realized that she’d hung up the call.
Wow, she really doesn’t mess around, does she? I thought, as I lay there on my back in a total daze. Part of me wondered if that had really even happened, but a quick check of my call log told me that yes, I had definitely just received a call and wasn’t going crazy.
I could still hear her cold, stern voice echoing in my head, that sexy English accent burned into my brain, and I realized with a shiver that my cock was still rock hard too. But for some reason, even though I wanted nothing more in the whole world than to stroke it and squirt out my pathetic little load, I held back. Because now that Miss Cartwright was actually my boss, it was probably kinda unprofessional of me to jack off over her.