Welcome to the third chapter of this kinky tale of a career choice gone wrong. Please email me with any comments or reactions, and do think about donating to help support this wonderful site.
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MY NEW CAREER - PART 3
As I took the last, faltering steps to reach the sanctuary of my apartment, I reached into my trouser pocket for my keys. Only I didn't have a pocket ... and I wasn't wearing trousers. Swearing, I fumbled with the unfamiliar catch of the handbag slung over my shoulder. Digging inside, I found the keys, but as I pulled them out they slipped from my shaking fingers and fell to the floor. Reflexively, I reached down to grab them ... and very nearly toppled over head first, as I overbalanced on the unfamiliar heels I had been wearing now for the best part of the day.
Cursing both my own stupidity and the terrible turn of events that had seen me having to make my way in these impossible shoes, I straightened up, then sank down again, this time bending both knees as I had been taught. Scooping the keys up, I had to endure another bout of fumbling before I could get the door open.
For a moment I stood inside the darkened apartment, just trying to gather my wits. Then, flicking the light on I tottered on weary legs to the bathroom. It was a good few minutes before I could bear to look at my own reflection. And when I did, it seemed I was looking at some kind of screen, not a mirror. I simply couldn't associate myself with the figure I saw. Not wearing a school uniform, with hair in bunches and elaborate makeup marred only by smudges of red lipstick around the mouth.
Blinking at the strange sight, I sighed, then moved to the sink to try and rinse the taste of cum out of my mouth ...
Four hours or so previously I had been standing in the principals' office at Ceder College, still dazed from the transformation I had undergone and trying now to make what seemed an impossible choice. I could either become a plaything of Gordon Everett and be allowed afterwards to travel home without either makeup or (most of) the female clothing I had been forced to wear. Or I could take my chances with his sister Kristen instead, but remain fully feminised for the journey back to my apartment.
As I quickly thought about it, however, the decision didn't seem so hard after all. Notwithstanding my surprisingly erotic encounter that morning with Jason, the pretty student who had so memorably sucked me off, I had no desire whatsoever to put myself in the clutches of another man. I obviously didn't know what Miss Everett might do with me, but how bad could it be? And I thought I had enough cash in my wallet to afford a cab home, which would spare me a lot of public scrutiny.
There were no remonstrations from the two principals, just amused grins, when I announced my choice. "Told you", said Mr Everett to his sister, as he got up to leave, Pausing at the door, he gave me a searching look, then said: "Well, bye for now Katy, I'll look forward to seeing you tomorrow. And remember, a pleasure deferred is a pleasure increased ..." With a last wink to his sister, he left the room.
As the door closed, Miss Everett gave me a wicked smile. "Good decision Katy! Well, from my point of view anyway ... You may yet think otherwise though." Gesturing imperiously to a straight-backed chair, she ordered: "Take your jacket off and then sit down there, arms by your side." Her tone brooked no disobedience and I quickly complied. While I sat there, nervously wondering what she had in mind, I heard a rustling sound behind me, then silence.
Without warning, thee was a flash of green as something dropped over my head and into my lap, then another. Before I could react I felt the pressure of what was clearly some kind of rope or twine as it was pulled tight around my arms and upper body. More coils followed and in only seconds I was trussed to the chair.
"What the -", I started to exclaim as I tried to twist around, but a cuff to the head stopped me. "Speak when you're spoken to, Katy, remember?" hissed Miss Everett in my ear. "Yes ma'am", I said in a miserable tone.
"Good girl", she responded. "Just remember who's in charge here." I felt her hands rest lightly on my shoulders. Then with a sudden jerk she pulled back hard, overbalancing the chair and toppling it to the ground.
Helpless, I cried out with fear and waited for the back of my skull to crash against the floor. But then my progress slowed and I realised she must have caught the chair back and taken some of its weight. It still came down though with sufficient force, even on the plush carpet, to jar every bone in my body.
Gritting my teeth, I resisted the urge to ask Miss Everett what the hell she was doing, as that would clearly do me no good at all. As it was, I was left on my back, stocking-clad legs bent up in front me, skirt open to expose my black panties, and still firmly secured to the upended chair. I heard her move across the room and the click of the door, then silence.
I was left for a good fifteen minutes to ponder my fate. If I'd struggled, I might have been able to get free ... but I didn't know how quickly she might be back. And besides, she and her brother had all the leverage they needed to secure my ongoing cooperation. Trying to run out wasn't going to solve that - especially as I hadn't seen any of my clothes or personal effects since the morning.
By the time Miss Everett had returned I'd been able to calm myself down a little. But any composure I'd regained quickly vanished when she came to stand over me. I looked up to see that she'd changed her clothing - and how. I dimly took in the black leather corset that now encased her upper body, but it was her bottom half that had my full attention. Rising up above me were black, thigh-high boots in the same material, with slender, spiked heels. And above them ... nothing. With a start, I realised that I was looking straight up at her naked, shaved pussy.
Her chuckle tugged my gaze up to her face. "Bet you weren't expecting that, were you?" she said, peering down at my helpless figure. She made a gesture and I saw that she was holding some kind of long stick - perhaps a riding crop? - with a silver tip on the end. As I watched in horrified fascination she moved the tip down so that it rested lightly on the barely noticeable bulge in my panties.
There was a click, a flash and I felt a jolt of pain surge through my genitals. More surprised than in agony, I yelled out and arched my back, almost lifting the chair off the floor in the process.
Miss Everett tutted reprovingly. "Perhaps next time you'll think twice before deciding that I'm your least worst option? I am so tempted to have some real fun with you ... But for today, as you're looking so attractive in that uniform, I think I'll settle for seeing you exactly where I like pretty girls to be."
She turned around and then knelt down, straddling me and shuffling forward until her naked quim was poised above my head. "Eat me", she commanded, and sat down on my face, thighs clamped around my head.
I had never been particularly fond of cunnilingus, although I had got a lot of practice with one particular girlfriend at university who had insisted - fairly enough as it seemed to me - that a good munch on her pussy was a reasonable exchange for the chance to put my unimpressively small cock inside of her.
So despite the distraction of having a rather sizeable woman pressing what seemed like her full weight down on my nose and mouth, with little regard for my capacity to breathe, I found it easy enough to bring Miss Everett to a shuddering orgasm ... and then another, and finally a third. By the end, I was actually enjoying my capacity to arouse her, especially with no hair to tickle me or stick in my mouth. Indeed I was not a little aroused myself by the time she finally rolled off me with a groan.
If she noticed this though, she did not say anything. She simply freed me from my bonds, then used the button on her desk to summon Grace, who was evidently both a PA and a receptionist. As before, the young woman betrayed no reaction at what she found when she came to the office, but simply handed me a handbag and left.
I looked inquiringly at Miss Everett, who was now reclining on a couch, her face still flushed with the effort of her last climax. "You can take that home with you", she said. "You'll find a purse inside with a rail ticket that will get you home and back here in the morning. Plus your keys of course."
She stifled a yawn and then laughed softly. "I'm afraid though that we've kept your phone. And your cash and credit card - just in case you were thinking of, I don't know, maybe getting a taxi or something?" She laughed again at my expression, then gestured to the door.
"Okay Katy, we're done for the day. Just make sure you're back here by nine tomorrow morning, dressed the same way and fully made up, are we clear? And remember that those lovely high-heeled shoes will have to stay on until at least eleven tonight, or there'll be trouble. Understood?"
I muttered "yes ma'am" as politely as I could muster, slipped on my jacket and made for the door. Before I could leave though, Miss Everett stopped me. "I nearly forgot", she said. "Two more things. You'll need to make a bathroom stop before you leave, to repair your lipstick. You'll find everything you need in the bag, along with all your instructions from Lily and Daniel. Also, you may have noticed we haven't given you any fake boobs. We don't really believe in them here. But we do have some, so if you'd like to look a little more, shall we say, feminine in the chest department, you're welcome to take some .. They can be as large as you like!"
Face burning at this latest humiliation, it again took a lot of restraint for me to issue a polite refusal. I could still hear her chuckling as I left her office and went to the nearest bathroom to reapply my lipstick. As quickly as I could in my new heels, I scurried out of the premises I had entered that same morning with high hopes of starting a career as a teacher.
Keeping my head down and avoiding all eye contact, I was soon outside in the late afternoon sunshine. I took a quick look around, then crossed the road to a shopping centre. Scanning for a sign indicating toilets, I found what I was looking for and headed off to the facilities. I was just about to enter the men's room when I pulled up with a start and, after a brief hesitation, entered the ladies instead. Fortunately, nobody seemed to have noticed my indecision.
Finding a cubicle, I began a long and miserable wait for the sun to go down. I had decided that night would be my best cover to get home without attracting undue attention. There was nothing I could do about the artificial lights at the station or on the train, but there would also be fewer passengers by that time.
When I finally emerged, the shopping centre was virtually deserted. By sticking largely to dark backstreets, I was able to make it to the train station with minimal contact - though it was a little scary walking down some of those alleys dressed as a schoolgirl, of all things. By then I'd resolved to do two things: to walk steadily rather than to rush, which would not only attract attention but risk a fall in those damnable heels; and to keep my head down and avoid looking anyone in the eye. I'd reasoned that I couldn't stop other people seeing me, especially once on the train. But if I didn't look at them, then I wouldn't see their reaction - and there was less chance anyone would talk to me.
It was scary as all hell, and took a lot of concentration, but I somehow managed to stick to my plan all the way back to my apartment block. As I entered the lobby, I was just congratulating myself on making it back unscathed, when the lift doors opened and a figure emerged. Without thinking, I looked to see who it was and with a shock recognised my landlord, who lived in a ground floor apartment in the same block.
He glanced at me and walked towards the exit. For a moment I thought I'd escaped, but then with a cry of recognition he swung back to face me, grabbing me by the arm. "Hey, Martin - that is you, isn't it? What on earth are you doing looking like that???"
For one wild moment I thought about claiming to be my sister, but I couldn't recall if I'd ever told him about being an orphan - and besides, my voice would give it away immediately. So instead, I stammered an answer. "Oh, er, hi Mr Stokes... I was just, er, you know, getting ready for a, er, fancy dress party ..."
Inwardly cursing myself for not having prepared some kind of story - anything would have been better than the lame excuse I'd just given for being dressed as a schoolgirl, especially on a Monday evening - I saw the sceptical look that crossed his face. It was quickly replaced though by another expression that I couldn't quite read. It was not as if I knew him that well. He was a retiree in his sixties, a big bear of a man who worked out regularly and as far as I knew lived on his own. Our most common conversations involved me making excuses for being late with the rent. He'd been pretty reasonable, but the arrears had started to build up ...
It seemed like this was the topic he wanted to address now, because he told me he'd just been up to my apartment looking for me. "It's time we had a chat about the rent, Martin ... or should I call you Martina?" he said with what I thought was a slightly forced laugh. "Come on, let's go to my apartment, it won't take long, then you can head off to your ... party."
It was the last thing I wanted to do, but I was terrified of making a scene. So I followed him out of the lobby and round to the side entrance that led to his place. As we went he complimented me on how well I was walking in my heels, and how "hot" I looked.
Once inside his neatly furnished if somewhat spartan apartment, he led me into the living room and asked me to sit down. As I sank into an armchair, the still novel feel of the clothes I was wearing reminded me to cross my legs as I'd been trained, rather than sitting with them open. Demurely, I tugged the skirt down so that there was no sign of my stocking-tops.
When Mr Stokes offered me a glass of wine, I hesitated. But I didn't want to offend him, especially given my financial situation. He fetched a bottle and two glasses from the kitchen, poured us both a drink, then sat down opposite me. He then proceeded to chat about all kinds of things for the next twenty minutes. Since I didn't want to bring up the matter of the rent and neither, apparently, did he, the conversation dragged on. I was desperate to get out, but couldn't see any way. And all the while I was conscious of his eyes on me, roaming over every inch of my body.
Finally, and with a note of regret in his voice, he said: "Martin, we need to talk about the rent you owe. It's not that I'm desperate for the money, but it's the principle, see, and I've got other potential tenants who I reckon might be a bit more, well, reliable ..." He ran a hand over his balding pate and sighed.
I put down the glass from which I'd been sipping. "Look Mr Stokes, I'm sorry, things have been a bit tough for me ... But I understand your position, of course I do. So how much do you need and when do you need it by?"
He sighed again. "Well that's the thing, I've already issued you a final demand. So unless you can come up with at least, say, eight weeks' rent by tomorrow morning, I'm going to have to evict you. I'm well within my rights", he concluded defensively.
I stared at him aghast. I had no cash, no way of getting any ... and even if the Everetts agreed to return my credit card, which seemed unlikely, I still didn't have enough in my account to cover the debt. I'd hoped to negotiate a loan with the bank, especially if I had a new job. But with only a vague promise that I'd eventually be earning good money to go on, that seemed out of the question - again, even if I were free to go there in my own clothes.
Desperately, I burst out, "I'm sorry Mr Stokes, but I can't get the money on time. And there's ... stuff going on that I can't really talk about. Look, isn't there anything else I can do for you to help pay my way?"
As soon as I saw his eyes light up, I realised I'd made a mistake. Quickly I tried to add, "You know, maybe I could clean for you ... or something?"
Slowly, as if trying to pluck up courage, he looked around the room, drew in a breath and then said: "Well, see, there is something, yes ..." He hesitated, then plunged on. "Only, I've noticed you don't seem to have a girlfriend, and then I see you tonight, looking so ... lovely, and well, I was wondering whether you might ... sort of ... be my girlfriend? You know, just every now and again?"
He took a long draught from his glass, then looked at me apprehensively. I closed my eyes, groaning inwardly. "When you say 'girlfriend', you don't mean go out on a date, do you? You know, to the movies, or a restaurant ..."
I opened my eyes again to find him slowly shaking his head. "You're looking for something more ... physical, right?" A nod. "Starting now, yes?" A second nod.
So there it was. I could say no - and wake up tomorrow with no place to live, nowhere even to leave my stuff, and no way of making or paying for any other arrangements. While still dressed as a schoolgirl, and with an appointment first thing that I couldn't break without risking any future career prospects I might have, not to say my liberty.
It had been a day of hard choices. "Okay", I said, "what do you want me to do?"
His face broke into a beaming smile, as if he couldn't believe his luck. "Oh, thank you! You could just ... come and sit on my lap and we could have a kiss and a cuddle and you could ... make me happy. All right?"
I breathed out. I suppose it could have been a lot worse ... I thought hard for a minute, and then said: "All right. But all you get is a handjob, right? And you keep your hands out of my pants, are we clear?" He nodded his assent.
Slowly, I stood up and moved over to him. "One more thing. This clears my debt, okay? As for any future rent, well, that's to be negotiated." He nodded again, smiled and patted his lap. Awkwardly, I lowered myself until I was sitting partly on his ample frame and partly on the padded arm of the chair.
For a moment we sat there motionless. He didn't seem to know what to do and I sure as hell wasn't going to make the first move. But then he put his arm around me and shifted in his seat so that he could look at me. He brought his free hand to my knee and then gently, tentatively began to caress my nylon-covered thigh. As he did so, he moved his face into my neck and began to nuzzle me gently.
Although his voice was muffled, I heard him say: "I suppose you think this is weird. But I've been so lonely since my wife left ... My friends say I should marry again, but, you see, I'm just not interested in women my own age. I've always had a thing for younger girls and, you know ... ladyboys ..." I could feel him blushing. "Only I've never been game to do anything about it. But then, I saw you dressed up like this, looking so sexy, and in that outfit an' all ..."
As he was saying this, his hand been moving under my skirt, working his way up my leg. But as he reached the smooth, bare flesh above my stocking, he stopped abruptly.
"Yes Mr Stokes", I said quietly. "I'm wearing stockings." Gently disengaging him from my neck, I turned for the first time to face him. "Do you want to see them?"
"Oh yes ..." he breathed, then watched in awe as I pulled up my skirt and stretched out my legs so that he could get a full view. Careful not to gouge him with my heels, I brought my legs back down, then gently placed his hand back on my stocking top. "No higher, remember?"
He looked into my eyes, nodded, then suddenly brought his lips up to meet mine. For a second I froze, then tentatively returned the kiss, parting my lips gently to admit his questing tongue.
It was the strangest feeling, being kissed by a man. The usual softness wasn't there and I was initially very aware of the stubble around his mouth. But as it continued, I found it strangely easy to just lose myself in the interlocking of lips and the sinuous interplay of tongues. I was dimly aware of him pressing his body against mine, one hand caressing my cheek and neck and the other roaming over my legs and then around to squeeze my bottom.
Breaking the embrace, he held me away from him for a moment, looking at my face and then down at my body, as if wanting to reassure himself that this was really happening. "Oh Martin", he breathed.
Without knowing what prompted me to say it, I answered: "It's Katy ... I'm Katy when I look like this ..."
He smiled, nodded and said "Hello Katy ..." And then he was kissing me again. And I was kissing him back.
As our bodies pressed together, I felt him take one of my hands and move it slowly down until it was resting on his groin ... where a warm, hard lump was waiting. Shocked, I went completely still. Whatever illusion had allowed me to return his kisses had suddenly vanished and I realised I was making out with a man - very much of a man, if the lump was any guide.
Once again, he drew back and looked into my eyes, but this time with a worried expression. "Please, Katy?", he whispered. I blinked. A deal was a deal ...
Nodding, I slid down and off him until I was kneeling between his legs. Then with trembling fingers I undid his belt, unbuttoned his pants and tugged on the zip, struggling to get past the lump inside. Mr Stokes reached down and helped me to get the zip all the way down, then eased his stiff cock out through the slit in his boxers.
What a sight it was! Although not much longer than mine it was far thicker, with an enormous head. The skin was mottled and the shaft interlaced with veins. The landlord guided my hands to it and I felt it leap and twitch under my touch. Well, this at least I knew something about, even if it was from a different direction than usual ...
Spitting in the palm of my right hand to moisten it, I wrapped it around the shaft and began to pump it steadily, using my left to fondle the enormous ball sac that hung beneath it. Mr Stokes groaned in pleasure, but then gestured for me to get back up on the chair with him. So I repositioned myself so that I was half-lying across him again, allowing his hands to roam over my body while I wanked him with one hand.
As I picked up the pace, he started moaning. "Oh god Katy, yes, that's it, harder ... oh, you're so beautiful, and your hand feels so good ... oh please, harder!" I moved my hand faster still, grunting with the effort,mane his cries became more incoherent.
Suddenly he was stiffening and his mouth opened in a silent O. Just as I looked down, his big cock bucked in my hand and sent a stream of spunk straight at my face. I tried to duck, but simply managed to guide the jet straight into my mouth. With a startled yell that was cut off as I choked on the viscous fluid , I managed to redirect the remaining spurts away from me.
Letting go of the massive appendage, which was still twitching and dribbling cum, I would have leapt out of the chair, had its owner not grabbed me in a crushing embrace.
"Oh Katy, oh you beautiful schoolgirl, oh, I came so hard ..." he said as he stroked my head and squeezed my butt.
"Really", I said drily, "I hadn't noticed. Seriously Mr S, I had no idea cocks as old as yours could shoot that far! How long has it been, for god's sake?"
He chuckled then. "A while, Katy, a good while ... And listen, call me Graeme, okay?"
I gently disengaged myself and got up, twisting my face at the taste in my mouth - though I seemed to have involuntarily swallowed most of the cream he had deposited there. Turning round to face my landlord, I said: "Look, I'm sorry, I need to go - I've got to get ... cleaned up, okay? But thanks for ... letting me stay. I really appreciate it."
I paused, and then leant down to plant an awkward kiss on his cheek. "Bye Graeme."
He looked at me for a second, his gaze travelling up and down my body. The he shook his head, smiled and said: "Goodnight Katy - and thank you for making my fantasy come true. It was worth every cent. And I hope we can do it again some time."
I smiled noncommittally and let myself out, leaving him still slumped in the chair. As I went back up to my apartment I sincerely hoped that this was the last time I would have to do anything like that. But with the bizarre turn my life had taken in a span of just twelve hours or so, I feared there was more to come - a lot more ...
[to be continued]