Desperate Ch. 05

Apologies to my loyal readers - Chapters 4 and 5 needed a little rework to correct timelines, and I've had a couple of other stories to progress, as well as life getting in the way. Anyway, Vicky's journey is nearing completion. Chapters 6 and 7 should, I hope, complete the 'caterpillar to butterfly' transformation. And then she stretches her wings...

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Chapter 5 - Branching Out

On Monday morning, I arrived at the office before 7. I'd gotten there as early as I could, to prepare for Mr. Rogers' return. I'd made sure that work-wise, there was nothing for him to spend much time on; I'd already handled most of it myself. I'd even managed to answer a lot of his emails, as they seemed routine. There were two enquiries about potential large orders, which he just needed to look over as I'd already answered the questions that the customers had. I know the business pretty well by now, and it's only when we need an important decision that Mr. Rogers really has to be involved in the day-to-day stuff.

But as for the non-work stuff -- well, so much had changed, and I was eager to show Mr. Rogers exactly how much. That morning, I'd prepared carefully before leaving home. I'd showered, done my hair and makeup, and moisturized my pussy lips, relishing the smoothness. I put on a nice lacy corset-style garment I'd bought at the weekend -- it felt so naughty, just buying it - which lifted and held up my (slightly saggy) boobies and pulled in my (still rather rounded) tummy. Then I put on a low-cut blouse and my new suit, which looks smart and a little sexy at the same time. I'd gotten used to going around without panties now, and I really liked the feel of the air against my pussy. So as not to attract attention in my new, sexier outfit, I put on my old raincoat over the top, and a pair of flat shoes, picked up my bag with my 'other items' and headed for the bus.

When I got to the office, I hung up my raincoat, put on the new pair of lacy-topped hold-ups with seams that I'd also just bought - carefully adjusting them so the seams were straight - then I climbed into my sexy heels. The feel of the skirt lining against my butt cheeks and the air circulating around my bare pussy, plus the constant thought of what was going to happen today, had all made me very wet. I was dying to get my little vibrator out and buzz myself into ecstasy under my desk, but instead I set the coffee going, started up Mr. Rogers' PC and then sat patiently, reading one of my favorite stories from Literotica until Mr. Rogers arrived, while getting even hotter.

I think Mr. Rogers had had the same idea as me, because he was in the office around 7:15. He said 'hi Vicky' in the usual way and headed into his office. First thing in the morning, I usually take him his coffee, then we discuss anything that has to be done that day. When I went in -- making sure to close the door behind me - he was just scanning his emails. I told him I'd already dealt with most of them, and that there were two folders, one with a couple of non-urgent items requiring his attention, the other just showing the work I'd completed while he was away, in case he wanted to check.

I could tell by the way he kept looking at me that he wasn't thinking too much about work at that moment. "Vicky, you look very nice today. I love the new outfit. Turn around." I slowly turned so that he could admire me from all sides. "Excellent. I think you've really lost a lot of weight. Have you been following the regime I set for you?"

"Oh, yes, Mr. Rogers. I've done everything you asked of me - and more. I'm sure you'll be very pleased."

"How much weight have you lost?"

"Ooh, around fourteen pounds. I've dropped a dress size. I'm really pleased, and I feel a lot fitter -- and tighter."

"Excellent. What about the other things. Have you practiced those?"

"Oh yes, Mr. Rogers. I've used the vibrator a heck of a lot lately on my pussy and my clit. Oh, and I've used my initiative a little. Do you like this?"

I slid the tight skirt up my thighs until it was around my waist. (I'd practised that move many times in the mirror to get it right). The look on his face said it all.

"Hey, Vicky, that's amazing. Your pussy looks really pretty without the hair. And very sexy, with the stockings. Very sexy."

My pussy was tingling fit to burst, my pulse was thumping in my ears. I was really taking control of my sexuality for the first time in my life. It was terrifying -- and exhilarating at the same time.

"Mr. Rogers, I think I've changed a lot, and I'd like to change my name to reflect that, if you don't mind? Could you please call me Tori from now on? I think it sounds sexier and younger than Vicky, and I feel sort of sexier and younger."

"I think that's a great idea, - er, Tori. So what else have you done?"

"Oh Mr. Rogers," I said, letting the skirt fall back into place, "I've read a lot of the stories on Literotica. Some of them were a little gross, but some were really sexy. I needed to use the vibrator a lot -- a real lot!"

He grinned. "Excellent. And did you bring the zucchini and honey to show me how far you've got with that?"

"Well, no Mr. Rogers. You see, the zucchini got a bit skuzzy, so I've gotten rid of them. But I thought I might -- you know -- demonstrate on the real thing. Would you like that?"

I could see from his face that he was getting turned on by what we'd been saying. So I sashayed over to where he was sitting, moving round behind his desk as he swiveled his chair round to face me. I took off my jacket and laid it down on his desk, then unbuttoned my blouse so he could see the tops of my boobies, pushed up and out by the corset. Then I lifted my skirt again so that I could squat down in front of him. I moved into a kneeling position on the carpet behind his desk, reached out and unzipped his pants. As I suspected, he was already hard, and it was quite difficult to pull his cock free from the tangle of clothes.

For a moment, I was a little apprehensive about what I was about to do. I knew that he had said that the biggest zucchini was the same size, maybe a little bigger than his cock, but all the same, when I saw it again, that cock did look awfully big. My practice sessions with all three generations of Mr. Zucchini hadn't been easy, but I'd persevered, preparing for -- well, for this moment. So I smiled at him, as confidently as I could.

"Are you ready for me, Mr. Rogers?"

"His voice was a little husky. "Sure, Tori. Give it your best shot. Show me what you can do."

I licked the tip, tasting the salty pre-cum. Then I took the head inside my mouth, and Mr. Rogers let out a sigh. I licked it, swirled my tongue around, traced the contours. This was a lot more fun than Mr. Zucchini. The tip was firm but with a sort of soft, velvety feel, and when the large head slipped past my teeth, I realized the shaft was a little slimmer, so the stretch in my mouth wasn't so much. I slowly bobbed my head up and down, each time moving a little further down the shaft, until the tip of Mr. Rogers' cock pressed against the back of my mouth. Then I held it there for a few moments, breathing, sucking gently, swirling my tongue as best I could.

I looked up to see whether Mr. Rogers was enjoying it. The look on his face told me I was definitely on the right track. When I felt like my jaw really needed a rest, I slowly pulled back, letting him slide out of my mouth.

"Wow, Tori! You've sure learned fast. That was great. It felt really good."

He went to put his cock away, but I stopped him.

"No, Mr. Rogers, that was just to show you I could take your cock in my mouth. I want to give you a proper blowjob. I want to make you come. You can -- you can fuck my mouth if you like. Try to be gentle with me until I'm used to it. Please?"

Before he could react, I slipped my mouth back over his cock, and starting sliding it up and down, trying to mimic the in and out motion I guessed happened when a man fucks a woman. "Lips, tongue, no teeth" I kept repeating in my head. "Lots of saliva, deep, no teeth."

After about a minute of this, Mr. Rogers placed his hands on my head, and I could feel him starting to thrust, moving a little faster, pushing a little harder. Fantastic. I was really turning him on now, I could tell. I'd practiced hard, several times a night for the last few weeks, training my jaw to stay open, training my teeth to stay clear, working up the wetness, circling the tongue. This was what it was all for, pleasing my boss, sucking off the man who had showed me I could enjoy sex. I felt so wet and tingly between my legs, I had to slide a finger into my pussy. Ooh, it felt so good to rub my clit while Mr. Rogers' cock thrust deeper and harder into my mouth.

The head of his cock was pounding against my throat. It felt a little uncomfortable, but not as bad as Mr. Zucchini. A cock head is softer and more flexible than a vegetable, and anyway, this was much sexier, so my mind felt I was enjoying it -- even the ache in my jaw.

Then Mr. Rogers thrust quite hard, groaned and started to pull back. The next thing I knew, there was this thick, salty, slightly bitter fluid, filling my mouth. He held my head still and moaned louder as more spurts gushed out. I spluttered as some went down the wrong way. I gulped and tried to swallow. As he finally pulled out, the rounded head slipping past my lips, another spurt splashed over my cheek.

I was still coughing and spluttering, and Mr. Rogers was breathing heavily. His face looked flushed and his eyes were closed, but I thought he looked even more handsome than ever. Finally, he opened his eyes and looked down at me, then started laughing. I was a bit upset.

"Oh, Mr. Rogers! What did I do wrong?"

"Wrong? Tori -- you did nothing wrong. You gave me a fantastic blowjob, I came in your mouth and you seem to have swallowed most of my cum. That's an amazingly sexy thing to do for a guy, and I had a really strong orgasm -- that you gave me. You've got cum dribbling down your chin and onto your tits -- your breasts."

"Oh, sorry Mr. Rogers. I'll go and clean up." I started to get up, but he put his hand on my shoulder and stopped me.

"No, Tori. Please. It looks sexy, and naughty, and -- and beautiful. Guys love to squirt their cum all over girls. It's some sort of animal power thing, like showing you've claimed an attractive female, I guess. Watching my cum dribble down your pretty, made-up face is very horny. Tori, baby, you've come a very, very long way. Thank you -- thank you so much."

I was in ecstasy. He'd called me horny, sexy, pretty; words that I'd never heard associated with me. And he'd called me baby. That was -- that was something else entirely, a real term of affection.

"Hey, have you been playing with your pussy?"

I blushed. "Well, yes, Mr. Rogers. I sorta had to. I was so wet and turned on by having your big cock in my mouth at last."

"Hey Tori. Stop apologizing. Stand up -- no, keep your skirt around your waist. Here -- up on the desk."

"Mr. Rogers. I -- I'd really like you to fuck me, but -- but not here, not right now, please. It just wouldn't feel right for like, my first time."

"Don't worry, Tori. I do really want to fuck that sweet little pussy -- get my cock into that juicy little cunt -- but you've just sucked all of my juices out of me. And I agree, I want it to be in a nicer place than across my desk -- at least the first time. Just sit back against the edge of my desk for now and spread your legs nice and wide."

I guessed he was talking dirty to get me even more turned on, but I wasn't sure if I could get any hornier. As I settled on the desk edge and opened my legs, I found I was leaving a slick of juices on the smooth wood. If I was this wet at home -- normally after reading several stories and using my vibrator for a while -- I'd feel the need for good old dependable Mr. Zucchini to be introduced again to my dripping hole. This time, however, though half of me ached for Mr. Rogers to just shove his cock into me, I still felt that my first time needed to be more special. So I was really pleased when Mr. Rogers slipped first one, then two fingers into me -- into my cunt -- and then knelt down and started licking my pussy.

His tongue slid up and down between the front of my cunt and just short of my clit. Then he pulled back a little and teased my butt-hole with his tongue, which felt weird and very, very naughty. Then his strokes zigzagged up, across my pussy lips, while his fingers seemed to find most of the sensitive spots inside me that Mr. Zucchini had help me identify.

And then he found my clit. Actually, he didn't so much find it as own it. He swirled around it, lapped it, nibbled it, pulled the hood back and gave it the full treatment, with the flat of his tongue and then buzzing the tip against it. In less than a minute, I came. It was so strong, my knees gave way and I almost collapsed off the edge of the desk. I wondered whether anyone else was in the office and may have heard me -- I hadn't exactly been quiet.

He got up off his knees, put his arms around me and kissed me. It was so lovely, I started to cry. Less than three weeks earlier, I had been sobbing on his shoulder because stupid, fat, ignorant, ugly Leroy had dumped me. Now I was a different woman -- a new name, a whole new life. I had orgasms. I dressed sexily. I had my pussy waxed. I gave blowjobs -- well, a blowjob. And I got my pussy licked. All the kind of things that a normal, sexy, mature woman might do. I was no longer a freak.

But I was still a virgin. OK, so I'd lost my hymen and Mr. Zucchini had given me an orgasm, but I'd still never had, like, a man between my legs. And I really, really wanted that.

Mr. Rogers looked at me and smiled. The tears were running down my face, but I smiled back. "Thank you. Thank you so much. That was -- amazing!"

"Vicky -- I mean, Tori. You were amazing. That was a very hot blowjob you gave me. Some girls won't let a guy come in their mouth like that, and a lot won't swallow. You did everything - and you acted in a very sexy way. You've come a hell of a way in just a few weeks!"

"Gee, thanks Mr. Rogers!" My face must have looked a picture. My mascara had run, I had semen spattered on my cheeks and dribbling down my chin, my hair was mussed up -- but I couldn't stop smiling.

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Most of that week, I found ways to do something sexy with Mr. Rogers. I'd go into his office, and ask him something innocent, and then while he was answering, slowly hitch up my skirt and show him my pussy. I'd stand there, as if nothing strange was happening, and then a few moments later I'd pull the skirt back down, thank him and walk out. One evening - Thursday, I think - I was wearing a more-floaty skirt rather than my normal tight business suit. Late afternoon, after everyone else had gone home, I went in to see him. I kept playing with the hem of my skirt kinda nervously as we were talking, lifting it up high enough that he could see my stocking tops and get glimpses of my bare pussy. He told me to close the door and to come over to where he was sitting. Without a word, he slid his hand up under my skirt, straight into my slit, and a moment later, into my vagina. I was panting within a few moments.

"Tori, you're being very naughty. You shouldn't tease me like that. Where's my finger?"

"In my cunt, sir," I replied.

"And what else should we putting in your cunt, Tori?"

"Oooh - your - your cock, sir." He was teasing all the sensitive areas.

"Do you want that, Tori?"

"Oh yes! Yes, please, Mr. Rogers."

"Good. Because you're driving me crazy with all this teasing." He stroked my pussy, running that finger in and out of my cunt and across my clit, until I was fizzing. Then he dropped to his knees and ate me again. It didn't take long until I came.

"Tori, I have to get home. I can't stay late tonight; we have visitors arriving for the weekend. Tomorrow, as you know, I'm in all-day meetings with the guys at Brightwell. If I could stick around, I don't think your virginity would last another hour. I can't get away until Monday. How about we do it then?"

"Oh yes, Mr. Rogers, that would be wonderful. I'll make it extra special for you. But Mr. Rogers, do you have maybe ten minutes - right now?"

I dropped to my knees and kinda engulfed his cock in my mouth. I took him as deep as I could go, keeping everything as wet and soft as I could, slowly slurping him up and down. We didn't need ten minutes; he filled my mouth with cum after less than two.

We both cleaned up, then we locked up and he gave me a ride part-way home. I walked the last four blocks in my heels, feeling the cool air on my bare, still-wet pussy, and felt as horny as Hell.

For the first time in nearly two weeks, I skipped gym. I just cleaned up, taking care to reapply my makeup that way that Ashlyn had shown me, and took a cab about ten blocks to a little bar that I'd been to a couple of times. It was quite pleasant -- the sort of place where a woman could sit on her own and not be molested by sleazeballs -- and they were advertising live music. I admit I had to pluck up courage to go in. I almost never went into bars on my own. The last time I'd been there was with Leroy -- he'd worn a jacket and tie, which was an effort for him -- and I'd felt self-conscious. So I hung around outside for several minutes, telling myself that I was a confident, attractive woman who was out for a pleasant evening, a couple of drinks and some music. And the glamorous little black dress with the wrap-over skirt I was wearing -- my second major purchase from the boutique earlier? Well, that was just because I had nothing else to wear. Honest!

Finally I took a deep breath, put on a smile, and sashayed in. It was the heels that did it. They totally changed the way I walked, and it added a sort of wiggle. To my surprise, I noticed a few guys look up and check me out. Me! And by the time I'd reached the bar, this guy had spotted me and arrived alongside of me. Then the guy to my left turned, and I realized it was Leroy! I quickly turned away, instead smiling a little nervously at the tall man who now stood to my right. He smiled back. I thought he had a nice smile. I also thought he had a nice butt; the new me noticed things like that.

"Hey baby, you're new here, aren't you? Can I buy you a drink?"

"Sure I'll have..." What should I drink? What would appear sophisticated?

I glanced up at the drinks list behind the bar. "A -- a Margarita, please."

"Sure. Hey Jerry? A Margarita for the lady and another whisky sour for me, please?"

"Coming right up, Jake," the barman replied.

"So - so you're Jake are you? My name's Tori." I held out my hand and he shook it - a gentle but firm handshake. Inside I was so nervous I was trembling, but I kept smiling as best I could. Jake was, I guess, a little younger than me; maybe late thirties, early forties. He was quite tall, had a nice smile, big blue eyes that I really liked, broad shoulders and looked good in his soft white shirt and tight jeans. Oh, and like I said, he had a cute, tight butt. I glanced in the mirror and realized that Leroy, sitting on the stool to my left, hadn't recognized me. He looked pissed that he hadn't even gotten to speak to me before his much-better-looking rival. When I saw his reflection, he looked even more unattractive than he had just a few weeks ago when he'd dumped me by email. I felt sudden a surge of confidence; I'd improved so much that the guy who'd dumped me not only didn't recognize me, but wasn't even making a play, as he could see I was out of his league!

"So what brings such a pretty lady out here on a Thursday evening?"