Mature Prudish Woman Blackmailed

As always I encourage all comments. I do take note of all opinions

My name is Julie, I am 50 years old. 5ft tall, black hair, with I suppose just an average figure. Although my friends say I am quite pretty, that's as far as it goes, otherwise I am rather nondescript.

I am also a thief.

Let me explain.

I had been married to the same man (Robert) for 30 years, when he tragically died and left me alone. Although I am over his death now, I struggled to cope financially on my own. We had a circle of friends on the same housing estate that we lived on, who were not mega rich, but they mostly had two incomes and could afford a new car every couple of years, always had a good annual holiday and the women always had enough disposable income to keep their wardrobe up-to-date and with the prevailing fashion of the time.

I didn't want to steal for the usual greedy reasons, I just felt that if suffering the death of a husband wasn't enough, to be condemned to live poor, always struggling to make ends meet as well, was unfair on me. I wasn't looking to steal for luxury, just for everyday nice things.

I work in the cash office of the local supermarket, this is a privately owned business not a large chain. One day I simply looked at all the money laid around after the tills had cashed in and thought,

"Look at all that money that is going to one person. I don't want it all, but why can't I have just a little of it?"

So I took some money and simply made the appropriate alteration in the ledger - it was so simple I couldn't believe it! The out-of-character stealing continued for a few months and I enjoyed the new found comfort it gave me.

There is a saying that if something seems too good to be true, then, it usually isn't.

I got caught.

.....................................

My name is Jack, I am 22 years old and my father owns the local supermarket in our small town. I didn't want to go into the family business but I failed to find a job anywhere else and due to my computer 'savvy' I was pushed into taking a junior I.T. role in the business. I had only been there a few weeks, when I discovered that someone was stealing from the office. The person was not very clever about it, as a simple audit trail showed the same person making adjustments in the computerized ledger at the same time and for the same amount every week.

I never came into contact with the staff and none of them knew who I was and vice versa. I decided that before taking my findings to my father, I would 'suss' out who it was first. I asked discrete questions and had the employee pointed out to me and which desk they worked at. I went down and had a stealthy look.

That's when all my plans came into my head, that's why, when I saw who the person concerned was, I knew I had to try and turn this to my advantage. This was so very exciting and rich with potential for me.

Like all guys my age I grew up in the era of the internet. I have accessed an absolute mountain of porn and had hundreds of gigs downloaded and stored on my HDD. Over the years looking at porn, I have developed what you might call an all consuming love of the mature woman. I have absolutely no idea why and I wouldn't try to rationalize it, simply we are all different and get turned on by different things. Although I can appreciate the 'hot teen' that is abundant online, I always found myself being drawn to the 'real woman', the mature woman attracted me 'warts and all'. I found myself being attracted to plainer, everyday natural women and even found their flaws and imperfections to be sexy. I found these women sexier even more so than the perfect, young, flawless, cheerleader teen that seemed so plastic and fake to me, that I was supposed to be into. Just one example to explain would be tits, believe it or not I actually find saggy tits more attractive than the harder uplifted ones. A mature woman's tits as they sag slightly and the nipples point downward a little are, in my opinion, a perfect example of a 'real woman'.

So that's why Julie was not only a woman to take advantage of, she was (to me) perfect wanking material. She was probably an old cock happy slut that had had more cock than most, but that didn't matter one bit.

........................

I was at home one evening, when I looked in my bag and saw that a typed note had been put inside by someone. Curiously I opened the folded paper.

That was when my world came crashing down and my life changed forever.

"I know that you are stealing from work, and I have all the documentary evidence ready to hand over to your employer and to the police.

The amount you have been stealing would certainly mean that you are facing a custodial sentence.

Think about this I will contact you in again in due course."

"Oh my God, I thought, prison?" I had never considered that possibility. I hardly sleep for two nights as I waited for whoever knew about me to contact me again.

.....................

I had no idea how Julie would respond to my plans for blackmailing her. I decided to start off very gently to enable me to slowly ease her into doing my bidding. I sent her a package and her instructions.

....................

A few days after the initial contact was made, there was a knock at the door. I was given a small parcel by the delivery guy and took it inside to open it. I had no idea who it was from.

I opened the packet and took out the contents. It took my brain a few seconds to actually register what I held in my hands. I was holding a black lacy suspender belt, a packet of black stockings and a pair of high heel shoes.

In a daze I read the note and digested my instructions - my God I was being blackmailed!

........................

I had to know, before trying to force the woman into extremes of sexual activity, that she would actually do as I said and submit to me. She could decide to run headlong to the police or my father confessing all, rather than subjecting herself to what I had planned for her. To this end, tonight was a simple taster. It was aimed at getting her used to being blackmailed and for me to find out her reactions. I had Julie wear her stockings and suspenders, heels and not-too-short (easy does it I thought) skirt and to take a tour around several pubs and clubs of the town. I knew where I could observe the places I had instructed her to be and armed with an expensive camera I set off to observe.

I was in the corner of a room in the pub she was to visit first. I was sat where I knew I would be able to see whatever was to happen. I had waited ages and was just about to give up hope, when the door to the lounge bar opened and in walked a rather plain looking mature woman.

"My God she is actually here! I thought, she is actually going to go through with it."

I was surprised and not a little excited, Julie wore a knee length black skirt and I knew what else was underneath, because I instantly recognized the shoes that I had sent her. I watched her get a drink from the bar and very, very unsteadily, in unfamiliar (although I didn't know this) heels she walked across the room and sat herself down. This was the crucial moment, this was when I would truly find out if I was going to be in business or not. After what seemed like an eternity, Julie took a drink like she needed it then, looking round to make sure no one was watching, she hitched her skirt up her thigh.

I had a semi hard on already just purely on anticipation. When she crossed her legs and revealed a glimpse of her stocking top and her suspender clasp as it tugged the nylon upwards, my cock lurched a little more. When I saw her white milky thigh just above her stocking, it looked so alluring in contrast to the black, it became a full erection.

I won't describe each and every time she did this, but she toured the bars as instructed, sitting on bar stools, chairs and benches giving the same show. She obviously attracted the leering looks of some males. This wasn't all men because she was incredibly subtle about it, but the seasoned lechers who were constantly on the look out for things like this, got a treat.

And I got plenty photographs.

Julie decided that her loathsome ordeal was over, drank up and left the last bar. I couldn't believe my fucking luck, boy, was I going to enjoy this.

..................

I got home and wasted no time in rushing upstairs to my bedroom. I took off the disgusting clothing that I had been forced to show myself in and immediately got in the shower. I needed to cleanse myself.

At this point I think you need to understand who and what I am. Like I said I am 50 years old and quite pretty but otherwise plain. The reason I had found this little show of mine so disgusting, was simply my upbringing. I had puritanical parents, who had equally puritanical friends. This was not a great recipe for a marriage between the two couple's offspring. I found myself married to an equally (actually more) shy man as I was. My husband was a good, caring, loving man and I cannot fault him in anyway. Unfortunately the only thing I learned in the bedroom from such a man was duty.

He had sexual intercourse with me at irregular intervals. It was not exciting or even that pleasurable in fact. He would take his pleasure of me when his body needed it, always done in the same place/time/manner. The orgasms that I did manage to achieve over the years, owed more to my husband sometimes taking longer to finish than usual, therefore lasting long enough for me to take my own pleasure, than it did to any exciting sex.

Sexual intercourse was a grunting, rutting duty I had to endure as a wife, my husband neither wanted nor demanded anything more of me. The clothes I wore were functional, bland and drab, therefore when that package arrived I was shocked at their lewdness.

..............

As I looked at the photographs of Julie, I couldn't help but stroke my cock. As I said before I have a massive thing for the mature woman. I had trawled the net on mature sites for years and collected thousands of clips. If I was on the street and a mother and daughter came towards me, of course I would look at the daughter to see if there was any camel toe on show, nipple pokies etc, but the real object of my attention was always the mother. I was not into the forward, aggressive confident type, the sort who tried to compete with their daughters, wearing clothes too tight for them or 20 years too young. The older woman who made a show of herself trying to be attractive was quite simply UN-attractive.

When you are young, you somehow get the impression that old women (40+!!) dried up, that somehow their tits shriveled and the pussy dried up and that somehow their bodies just gave in. I had gathered a library full of the homemade, amateur, type of clips from the net that taught me differently and educated my naive, inexperienced mind into understanding just how beautiful a woman remained through middle age.

So when I saw a woman such as Julie or any other lady like her, dressed conservatively and more demurely than some of their counterparts, I found it sexy and yearned for what I knew lay hidden beneath that woman-next-door facade.

I knew Julie was just a slut-whore like the rest and I was determined to use the old cum-slut for my own gratification.

................

A few days after my ordeal I was starting to feel more relaxed, my ordeal was over. Whoever was blackmailing me had had their fun and I had paid my dues (as humiliating as it was.) The memory of several men trying to look up my skirt, whilst knowing what they could see was revolting, but at least it was over now.

...............

I had a friend who worked at the local cinema who was to provide me with the next stage of my plan. There was a suspended walkway from the ceiling that was used for access to the stage when it had been a theatre. This walkway was covered in and the glass painted black. You never noticed this from the auditorium, but I had been along the walkway and knew that with a little square scratched from the paint, I would have my perfect vantage point.

...............

I got home from work one day and entered through the front door. I bent down for the post and noticed an unstamped envelope. I opened the letter and read the contents.

"Oh God no".

I thought my ordeal was over, yet here on a printed sheet were more instructions that I had to follow, if I wanted to stay out of prison. I was instructed to go to a local cinema at a certain time and sit in a specific seat and to see what would happen. A man would sit by me and I was to engage in whatever activity was asked of me.

The inference was clear.

"Never, never, never." I spoke aloud through gritted teeth. I would not lower myself to this filth and degradation.

Just then my mobile phone gave a little ping to say I had received a message. I opened my messages and saw the text.

"Have you got my next little task yet? I await your acceptance."

That was all it said. I realized I had to call this person's bluff, I could not in all conscience allow myself to do whatever it was they had planned, so I replied.

"Go to hell you nasty blackmailer, I will not lower myself to this level, do your worst."

I shut my phone off and was determined to bluff my way out of my predicament.

I didn't turn my phone back on until I was in the office the following day. That morning I watched the boy from the post room walk down the office handing out the correspondence. Just as he was entering Mr. Grove the owner's office I heard the familiar ping of my phone again.

"Good morning my little playmate, I hope you slept well and are in good health today."

I wanted to shut the phone there and then but the message went on.

"Did you see young Tom the post room boy enter Mr. Grove's office? Well I suggest you hurry on in there, because there is a buff envelope on the top of his incoming mail you might be interested in. Good luck sweetie," it finished.

"Oh God no, he wouldn't would he?" (The sexual angle to all this had led me to assume a male was involved) I thought. I ran for the office and just blundered in.

"Oh sorry Mr. Grove, but there is a letter for me, that has got mixed up in your post. Ah here it is I will take it back with me."

Mr. Grove just grunted as he was on the phone and just muttered something like,

"Oh, ok Julie fine."

I could not wait until I had a break to look in the envelope, so I hurried of to the ladies to open it. I sat on the toilet and tore the letter open and took out the contents.

"My God, I thought he is deadly serious."

In the package was a covering letter to the company and computer printouts of all the incriminating transactions. I had called his bluff and lost, he had actually gone ahead and sent all the evidence against me to my employer. I now realized that this was someone playing for keeps and I had decisions to make. He would not hesitate in denouncing me. As if I needed one last push, the high resolution photographs of me sat in different pubs, alone, skirt high on my thighs, with stocking tops and suspenders on view to anyone who cared to look closely enough, simply closed the deal.

I was beaten.

......................

I had engaged in brinksmanship, if she had not retrieved the letter it would have been all over. Now that she had reacted in the way she had, it meant I had proved that I would do as I threatened.

I had her.

I didn't want to expose myself to my little victim too early. Although I wanted to have the old slut myself, I thought patience was a virtue and my time would come. To test her resolve without revealing myself as her blackmailer, I needed a guy I could use. I had a mate called Paul who would fuck absolutely anything, we all used to joke that his own granny wasn't safe - and she was dead! I primed him with the story that was doing the rounds of an older woman who liked to do young lads 'favours' in the local cinema. Although Paul wasn't stupid, his cock ruled his head and he saw nothing of a set up when I told him the time she was said to attend the cinema and that she always sat in the same place.

I know it sounds corny, but a lad Paul's age, 'young, dumb and full of cum' had only one thing on his mind now.

I knew when the quietest time at the cinema was and after talking to my friend who worked there, I picked a mid afternoon slot where they were often virtually empty. I gave Julie her instructions and went to take up my spot in the cinema walkway. I had no idea if she would show.

....................

I could not believe that I was putting myself in such a position as this. Dressed the same way I had walked the town in the first night of my torment, I entered the cinema and sat where I had been instructed, right on the back row. I settled to watch the film but I couldn't concentrate, my senses were alive to every little movement around me. After a while the inevitable happened, a boy of about 20 or so came and sat right next to me.

I tried to ignore him but he started making rude and lewd comments and coming on to me. I knew I had to comply with my abuser and let this loathsome individual touch me. He began running his hand up my leg and tried to push his hand up my skirt. I grimaced as I allowed his hand access and felt his fingers reach my stocking tops.

"Fucking hell, he said, you have come ready for action haven't you!"

After several minutes of this groping, whilst trying to get past my defenses and put his fingers on the crotch of my panties, he leaned into me and said.

"Suck my cock girl."

I was mortified, it was disgusting and I was not going to stand for it. As he tried to pull me down to his groin area, I fought him off until my phone made the familiar ping of a message received. I used this as an excuse to untangle myself from his octopus like groping and read the message.

"DO IT."

I was shocked and suddenly looked around me in a panic. Where was he? How did he know what was happening? I felt all resistance leave me, my blackmailer was somewhere he could see us. I was not going to be able to get out of this without doing as he demanded.

Taking me for a loose woman, the boy lay back as he realized that he was about to get lucky. All the stories about the 'old slut' were true, here she was about to perform oral sex on him.

Without any finesse, he quickly fumbled in his trousers and took out his semi rigid penis. I don't know what he took my hesitation for (I think he thought I was impressed and wanted to savour the moment) but in a mocking tone he said,

"Come on darling, it won't bite you," and laughed.

As I lowered myself towards his groin, I saw his hard angry looking penis. It was about the same size as my late husbands. I encircled the girth with my fingers and felt the hot, powerful, pulsing, throbbing energy within the hard eager penis.

I smelled the musty aroma of him as I peeled back his smooth foreskin revealing a swollen, purple, angry head.

The last vestiges of my self esteem disappeared and I silently apologized to my late husband for the disgraceful act I was about to perform.

I opened my mouth and let my lips encircle the helmet.

I was useless.

I performed the task in a perfunctory manner. I had given my husband oral sex before on several occasions, however they were always as a precursor to penetration - I simply did it until he was hard enough to penetrate me. I had no technique whatsoever.

This horrible boy in the cinema had to tell me how to fellate him.

At his prompting, I ran my lips up and down his length, stopping to give the helmet of few sucks now and then, all the time slowly working my hand up and down the penis. He kept raising his hips and trying to push the throbbing pole into the back of my throat, making me gag.

As I said before I had only done this before as a way of getting my husband erect, so when this horrible boy grunted and started calling me filthy names, I had no idea what was about to happen. I was taken totally and absolutely by surprise, when his semen suddenly erupted and started filling my mouth.