tagMatureDesperate Ch. 01

Desperate Ch. 01

bybad_hobbit©

Chapter 1 – The end of the line?

I just couldn't stand it anymore. When I got the email from Leroy telling me he never wanted to see me again, I just fell apart. He was the only guy who'd contacted me from the dating site, and I'd really hoped that we would hit it off. After just one date, when I thought we'd gotten along fine, he just dumped me. Not even face-to-face, but by email.

You see, I've never had a boyfriend. When I was at school, my parents were so strict; I was never allowed to bring anyone home. The boys, and some of the other girls, made fun of me at school because of my geeky hair and big glasses. So I got more and more neurotic. My folks never had any money to send me to college, so I started as a secretary as soon as I left school.

I know I'm a good secretary. Mr Rogers, my boss, has employed me as his personal assistant for nearly four years. He's been kind and pleasant, and he relies on me for lots of things, but I don't think he ever really thought of me as a woman. It seems very few men do. But then, I suppose I wasn't really a woman at all.

You see, when Leroy dumped me, I was forty-six years old. Yeah, I knew I was overweight, that my hair was mousey, that my dress sense was poor. My self-esteem was about as low as it could get. No man had ever found me attractive enough to take out on more than three dates. And the thing that upset me the most was that at forty-six, I was still a virgin.

I'd tried speed-dating, Internet sites, agencies – nothing. Absolute nada. I didn't even have many girlfriends to turn to. I just went home every night, desperately seeking for someone, anyone, who would be nice to me. But no-one ever was.

As I sat there, sobbing at my desk, Mr Rogers walked in. He's a nice guy; not what you'd call classically handsome, maybe a little skinny, but not bad looking. He's around forty, has quite a few lines on his face from the worry he has at work, I suppose, and his hair is a sort of tight, curly iron grey, but I think it makes him look distinguished. Anyway, he's better looking than bald, fat Leroy. And Mr Rogers runs his own company, while Leroy drives a truck.

But I knew I'd get nowhere with Mr Rogers. See, he's married, and his wife's real pretty, and he has two nice kids. Their pictures are on his desk. But he's kind, sympathetic. I think he likes me as a person. Only, he's my boss, so I couldn't really confide in him.

Anyway, on this particular day, I was an emotional wreck. The fact that I got dumped by a fat jerk like Leroy was the final straw. I was seriously thinking of ending it all.

Mr. Rogers passed me a box of tissues, and asked me what was wrong, waited until I stopped sobbing and asked me again. I explained that my latest date had dumped me, and he got all sympathetic and said not to worry, there'd be other guys out there. That's when I really fell apart. When I realized where I was, I had my head on his chest and my tears had made his shirt wet. When I could speak, I just blurted it out; no boyfriend, ever; no likelihood of getting one; a very high likelihood of dying a virgin.

He took my glasses off me, dried my eyes, held my shoulders gently, and repeated my name several times until I finally looked into his face. "Look, Vicky," he said gently, "I think I can help you with your problem, but you're going to have to trust me and do what I tell you. Do you really want things to change?"

"Oh Mr. Rogers, I want to change everything about my life – except working for you. I just don't know where to start."

He smiled, kindly. "Vicky, I think I can help you make yourself more attractive to men, but you have to make some changes. Not all of them are gonna be easy. Look," he reached into his jacket pocket and pulled out his wallet. "Take the morning off, go to that hairdresser's across the street and tell them to restyle your hair and do your make up. And also, to show you how to do it yourself. This ought to cover it." He pulled out two hundred bucks. "Let them do whatever they suggest is best for your face shape and hair texture. Come back and show me when you're done."

"Mr. Rogers" I blurted out. "Thank you! Thank you so much!"

"Vicky, it's my pleasure. But before you get too carried away, this is just the start. Getting your hair and makeup done isn't going to change you into someone who's going to attract the guys overnight. But when you come back, I hope you'll feel better, and we can talk about a plan to make it work out better for you. What do you say?"

He smiled so nicely that I began to well up again. He gave me some more tissues and said "Vicky, just stop crying and get over there. See how much better you'll feel when you get back."

And I did. The looks I got when I went in were quite mortifying; like 'what's this that's just crawled in'. True, my hair was straggly and greying and all over the place, and I hadn't had it properly styled in maybe ten years, just cut back to how it was before. And I didn't really have a clue with makeup. I mean, not a clue. But the girl who came over to me looked kind, and she smiled and asked what she could do. I think she could see I'd been crying. I said I needed a complete makeover, someone to make me look a whole heap better than I did, and could she help. There was a fleeting look of 'well, I couldn't do any worse', before she ran her hand through my hair and looked at me closely from several directions.

"Sure, I can help a lot. You need to get this colored – I'd suggest some reds and mid-browns - and cut short around here. Then you need your eyebrows plucked and some work on your skin. It'll cost a couple of hundred. Is that OK?"

"Sure – er, what's your name?"

"Ashlyn. What's yours?" She smiled. She was young and pretty, and I envied her for it.

"My – my name's Vicky. Look, Ashlyn, just do what you need. I trust you to cut and color my hair and do my face and whatever. I just want to change how I look for the better. Can you really do that?"

"Sure. Just take a seat over here."

So Ashlyn set about changing my look. She cut and colored my hair, like she said. She plucked my eyebrows, exfoliated and cleansed and moisturized and God knows what else. When I finally looked in the mirror, I definitely looked heaps better, maybe at least five years younger. "You know, I think you'd look better without the glasses, Vicky" Ashlyn added as I paid her – and tipped her generously. "I got my eyes lasered, but my sister wears contacts and they work fine for her."

I thanked her for her advice, and she smiled at me – a sort of buddy smile, rather different from the one she gave me when I arrived. I went back to the office – it was now nearly one pm – and presented myself for Mr. Rogers to inspect.

He seemed very pleased. "Hey Vicky, you look so different! You're not the woman who was soaking my shirt this morning; much more attractive, I'd say. How do you feel?"

"I feel – I feel much better, Mr. Rogers. But – do you think it's going to be enough to get me – to get men interested in me?"

Now that was one of those questions that, once I'd said it, I knew I should never have asked. There was no right answer. If he said yes, and all I'd ever needed was a haircut and some make-up, I would probably have been devastated for everything I'd missed. If he said no, then I'd feel like there was no hope.

"Vicky, it's a great step in the right direction, but like I said earlier, there's more you need to do. Even if you do everything right, there's no guarantee you'll find the right guy, or even any guy. I'm only one man, and if I shape you to how I think you need to look, it's only my view. But I'll do my best. I really want to help you. Will you trust me and do what I say?"

"Oh yes, thank you so much, Mr. Rogers!" I thought at that moment that I couldn't have a better boss.

"Vicky, I think the next stage will be harder. You need to get in shape and get some new clothes. If I get you a trial membership of my gym, will you commit to going there at least three times a week?"

"I – well I think I have to, Mr. Rogers. How much – how much will it cost?"

"Membership costs around fifteen hundred a year. But the first month is free."

"Fifteen hundred! Mr. Rogers, I don't think I can afford that."

"Vicky, you need to lose weight and get fitter if you want a guy. I can get you the first month as an introduction, but you have to keep it up. And that's both the money and the commitment. Can you do that?"

"I – I'm really not sure. I want to do it, but fifteen hundred bucks is a lot of extra cash for me to find with everything else."

He stopped for a moment, looked long and hard at me, then said "OK Vicky, here's the deal. I think you may like it. You go to the gym, do it at least five times a week for the first month. If you do that, and keep up the diet I'm going to get them to give you, I'll give you a raise to cover the gym fees."

"But that's so generous, Mr. Rogers. And do you think that all I have to do is lose weight and get more attractive?"

"That's part of it. But," he paused. "This is rather delicate. You said – excuse me for asking, but you did say - that you're still a virgin, is that right?"

I was suddenly flushed with embarrassment, and looked down at the carpet. "Y-yes, Mr. Rogers. I - I'm not proud of it, but it's the truth."

"So have you ever had any sexual contact with a man? Ever given a blowjob, or have a guy feel you up? Ever had your pussy licked?"

I was rather disgusted by what he was saying. What I most dearly wanted in the world was to have a good-looking man make love to me, to caress me and kiss me and make me wet, and then put his penis into my vagina and give me the sort of pleasure that I'd heard about in romantic fiction. That was how it was meant to be, wasn't it? As for the rest, my mom had always said it was dirty, and people shouldn't have anything to do with it. (She and my dad slept in separate beds most of the time I knew them anyways, so I guess not a lot went on between them in that department.)

I was a little breathless. True, Karl, this guy I was dating six years earlier had asked me to give him a blow-job. When I asked him what that was, he was surprised, but told me he wanted me to suck his penis – I think he called in his 'dick'. I was really rather shocked, and I ran out on him. Later, I realized that maybe that's why he never called me again.

"Mr. Rogers." I suddenly felt very foolish. "I just want to – you know, have... have sex, with a guy. Someone... someone who'll make me feel good. Someone who'll like doing it... to me."

"OK, Vicky. I think you need to understand what you're asking here. Maybe fifty years ago you could have expected to be a virgin on your wedding night, to have a guy who in truth was probably no more experienced than you were, who would make love to you – probably in a fairly inept fashion, but neither of you would know any better. But we're in a very different world now. Not worse, not better – well, possibly better, because I expect more people enjoy better sex nowadays – but definitely different. So do you really have no idea about sex?"

"Sure, Mr. Rogers." I looked around furtively. There was no-one else in the office. "It's just that the guy puts..." I was blushing madly by this stage, "...puts his... his penis... in a girl's vag... vagina, and sort of... moves it about..." I trailed off.

Mr. Rogers got up off his chair, walked over to the door and checked there was no-one else within earshot. Then he closed the door, and walked back to his desk, eyeing me closely.

"Vicky, look. Sex is about lots of things, not just simply... what you just described. There are many ways that men and women can give and receive pleasure, and that's just one. Look, maybe we could find you an escort to take you through the basics. What do you say?"

"An escort, Mr. Rogers? You mean like – like a male – a male, prostitute?" My voice must have betrayed the disgust I felt at being touched by someone who did things like that for a living.

"Vicky, I think you need to change your views on a few things. How do you masturbate?"

I must have gone bright red. "I... I don't think that's a suitable topic of conversation, Mr. Rogers."

His face suddenly changed. "Vicky, I'm trying to help you here. You're a valued employee and I like you as a person, but you really don't seem to understand. Now I've paid for you to have your hair and makeup done. You need to get some more flattering clothes and either lose the glasses or get better ones. You need to shed about twenty pounds and keep the weight off. And you need to think differently about sex. Now I'm going to give you an advance on your wages so you can hire an escort to show you the basics. Then we'll see where you go from there."

"Mr. Rogers, please. I – can't do it for the first time with an escort. It would just feel so – so wrong and dirty. I'd much rather do it with..."

"With whom, Vicky? I thought we were doing this because your recent track record was so poor and you couldn't find a guy to help you with your sex life."

I was suddenly really dejected again. Mr. Rogers, in his methodical way, had shown me a plan to make myself more attractive. But I couldn't have sex with just anyone – at least, not the first time.

"Mr. Rogers, it's just that... I don't want it to be a stranger who'll only be there for the sex and then leave again afterwards, never to see me again."

"Vicky, I'm sorry to say that's how most sex is conducted these days. But who would you like to be the one?"

"Mr. Rogers, couldn't... couldn't..." I blurted it out "Couldn't it be you... please?"

He looked at me with a strange expression. "Vicky, you know I'm married. I can't – just have sex with you because – well, because you want me."

"But Mr. Rogers, it would be a special favor to me. I'd never tell a soul, I swear! It's just that I want it to be someone who I know wouldn't hurt me or degrade me or – or tell everyone about what we did"

My stomach gave a sudden lurch. I'd said it now, and any moment I'd get fired, and I'd not only have lost the job I loved doing for someone who I liked and respected, but all of his plans for me would evaporate, and he'd probably want back his two hundred bucks for the hair and makeup session.

But he looked at me strangely. "Vicky..." his voice trailed off.

"Vicky, you've given me an idea. I've never really thought of you in a sexual way before. To be truthful, as you've probably guessed, I haven't really found you attractive in that way. But if you do as I say, take up the training program and the diet, get some better clothes and glasses – well, then I'll agree to teach you, Vicky. Do you understand what that means?"

"I – I think so, Mr. Rogers, and I'm so grateful..." my smile must have scared him, because he stopped me short.

"Vicky, stop! I said 'teach you'. It won't be like you described to me – at least, not to start with. You need to learn a lot more about sex than just the theory of intercourse. All those things I told you about – and more; you're going to have to learn how to do them. I promise you'll enjoy them – maybe not at first, but more as you get used to them. And ultimately, it will make you more attractive to men and you'll have a lot more fun. But if I'm going to teach you, rather than a professional escort, you'll have to follow my rules. Understood?"

I think I was trembling. On the one hand, here was someone I liked and respected agreeing to relieve me of my virginity. On the other hand, he was going to make me do lots of things I'd always thought of as disgusting. But when he looked at me, I could see that he wouldn't really hurt me, and he daren't tell anyone about our agreement, because of his wife.

It was as if his thoughts were headed in the same direction, because he said "Vicky, don't forget, this is my special favor to you. Don't abuse it. Don't get the idea into your head that if we do have sex, I'm going to fall in love with you. If anyone ever finds out what we do, you'll be fired with no references. Also, I'm going to organize the payroll so that the money is a six-months rolling loan. If you ever let me down, the loan will come due and I'll take it straight out of your wages and come after you for anything that's left. Understood?"

I was certain that I'd never breathe a word about this, but it sounded so scary that I also knew he was deadly serious. "I totally understand and agree, Mr. Rogers. You can count on me."

He gave me another look. "Oh, and by the way. If I tell you to do something for me, you do it, without question, understood? No telling me that something is disgusting, or it hurts, or you don't want to do it, OK? Everything I tell you to do is for your own good, so you learn how to please a man and also to get pleasure yourself. If you don't like it, you just smile and say 'yes, Mr. Rogers', and you go ahead and do it like I tell you. Understood? If not, the deal's off."

"Understood, Mr. Rogers." I had no idea what I was getting myself into, but I knew that if I wanted to stop being a dowdy old maid and start to enjoy this thing called sex, I had nowhere else to go. "Where do we start?"

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by Anonymous

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by Anonymous08/09/18

Too bad you had to make this a boss as predator plot.

If this woman agrees to become the boss's sex student I hope she also learns how to file a sexual harassment claim.

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by Anonymous08/07/18

Mr Rogers myst gave a first name

What qorkplace today has pwople called by their surname?
Surely nobody is as timid as her?

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by AnnaValley1108/06/18

Great start - more please

Very well written with great characters
Looking forward to Ch 2

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