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MATURE SEX

A Sissy Of My Very Own

A Sissy Of My Very Own

by lunadoggy
20 min read
4.63 (13200 views)
adultfiction

A SISSY OF MY VERY OWN.

As soon as clapped eyes upon my daughter's latest 'conquest,' I knew that THIS was the male whom I'd been looking for ever since the tragic death of my husband, some two years ago now. And possibly before even that, although I never would have betrayed him.

My Jeff had a been thoroughly decent, completely honest and really hard-working husband, our life together had featured many an outstanding 'high,' contrasting with very few 'lows,' which we'd got over very swiftly. A truly happy marriage, unusual these days I admit, tragically cut short, as some idiot unfortunately believed he could still drive having consumed a large number of alcoholic beverages during a company Christmas bash. Finding out that he couldn't, having slaughtered my husband in the meantime.

There was, however, one aspect of life that was beginning to prove problematic though, just showing that not everything was a 'bed of roses' within our, seeming idyllic relationship, sex. Jeff was very much a 'man's man' when it came to the pleasures of the flesh, ironically just how I wanted him at the beginning of our time together. He was highly skilled in between the sheets, strong, manly and passionate, every girl's dream or so it seemed. However, not long before our time together was so dramatically ended, I'd began to fancy being the dominant one in bed, I wanted to take charge and be the one setting the agenda.

I completely accepted Jeff for who he was, never once trying to change him. I married him entirely of my own free will, actually wanting him to be precisely what he was at first, but I'd began to read stories of dominant women on the internet and started to fancy a piece of that sort of action for myself. Although I did manage to suppress those feelings, my Jeff would never play the submissive I knew, and as for the idea of him wearing female lingerie, which by now I quite desired, well there'd be more chance of Accrington Stanley winning the Premier League than that occurring. But then, all of a sudden, he was gone.

A massive loss, as you can all imagine, and quite some time sex, whether in the form of what I believe is called 'femdom,' or otherwise was the very least of my concerns. As well as all the emotional aspects caused by the sudden dis-appearance of a loving spouse, whether we like it or not this world revolves around money, so there was a huge financial issue to resolve too.

Fortunately, matters in this regard soon became settled very much in my favour. Jeff had held a very lucrative life assurance policy, which paid out substantially, hardly surprising as he'd died so young and not by the actions of his own hand. And the very competent solicitor that I engaged, managed to obtain a huge pay-out from the guilty party's insurers. Meaning the mortgage upon the former marital home was redeemed totally, leaving a rather large sum with which I was able to obtain a very generous annuity. With then result being that I don't have to work for a living, and although I do still have a job, it is through choice rather than necessity.

This then, being my position in life the first time that my Joan brought Simon through my door. One look is all it took to see firstly that he was quite effeminate, and that here was a male who almost certainly was just what I was looking for, a male to dominate and control, just like in those stories that had so amused and entertained me.

Although there was one small problem, he had stepped into my home with my daughter's, Joan being the only child resulting out of my relationship with Jeff, hand firmly clasping his.

However, I know my daughter, and in many ways, she takes after her late father, rather than myself. Fiercely independent, although she'd yet to reach her twenty-fifth birthday, she'd, with her good job helping tremendously, moved out of my home and bought her own property, a small two bedroomed house. Just like her dad, she knows how to work hard.

And here's the point, she also follows Jeff's lead in the bedroom stakes too. I was quite amazed just how she'd picked Simon as her new boyfriend, sensing that their relationship wouldn't last too long. Like her dad, she seemed to believe that the man should control the bedroom, and this Simon appeared to have no idea of how to just do that.

So, I resolved to take no action yet, I might have got this wrong after all, but I did seek as much information as I could about this young man, in case I was correct about him. Like where he lived, his job but more importantly his habits, naturally if I did want to contact him on the event of him and Joan splitting up.

An event that happened even quicker that I'd anticipated, because only about three weeks later, as a furious Joan stormed through my door, slamming it HARD after her! Responding to my enquiry as to the whereabouts of Simon, with a terse "don't talk to me about that utter wimp!"

"Why? What's gone so wrong, Darling?" Trying my very best, successfully I might add, to conceal the absolute joy that her revelation had triggered inside of me.

"Did dad ever ask you if he could wear some of your stockings? Because that pansy sure asked me. Can you Adam and Eve it? Bloody stockings, I ask you?" ( English rhyming slang for 'believe.' )

"No, he never did in all the time that we were together, Darling." Secretly feeling completely delighted of course. After all, I WANTED him in stockings myself. But I couldn't tell Joan this.

"Are you sure, Darling? You may have just misheard him, or simply misunderstood."

"There was NO misunderstanding, mum! There I was putting on some myself, and he came straight out with it. 'Can I try some of those, I always fancied finding out just have good my legs would feel in sheer nylon?' What an effing", we'd always hated unnecessary swearing, both Jeff and I, "PERVERT! Anyway, him and I are DONE!"

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"Yes, I can see that, Darling. Clearly, he wasn't for you. But don't be too hard on him, ok so he's not your cup of tea, and I take it that you've made that clear to him. However, he struck me as decent and honest, after all he WAS straight with you, and didn't try to hide his fantasies, being up front and truthful, not trying to deceive you or act behind your back. Sure, you don't agree with what he wanted, but because of his cravings he's now lost you. Isn't that punishment enough?"

Joan seemed to calm down, reflecting upon my words. Of course, she had no idea of my desires, that I wanted to move in upon this, how had she put it, pansy. And what she clearly didn't want, or not yet, I'd have probably reacted in the same way at her age, I most certainly did. "Thanks mum, the fountain of knowledge, yet again. Yes, you're right, there's no need to slag him off publicly, as I was going to. I'm not with him anymore, and now I'll simply settle for that. Onwards and upwards, eh?"

"Precisely, Darling." Cue a long mother and daughter cuddle. And then, after a good and strong cup of coffee, Joan left to go to her own home.

Well, that was one problem solved then. I could now make my move without betraying my own daughter. But that left another. How would I contact him, and in such a way as to not arouse suspicion in his mind? It had to appear to be purely accidental, a total coincidence, not at all planned or actually wanted, Cue that 'homework' I'd done on him, once I'd decided he WAS for me, if not my Joan.

Just like me, the company he worked for was one of those whose working week ended at Friday lunchtime, and by now I knew that Simon nearly always chose to eat lunch in a café located just around the corner from where his employment was situated. And it was quite handy that for my employer lunch commenced at half past twelve, whereas for his it started at one o'clock. Meaning I had a 'head start' on him timewise.

It was also fortunate that said café was housed within a block containing several other shops, one of which was a rather special butchers, who had a reputation for making some, utterly delicious and very high quality, if a bit pricy, 'home-made' meat pies. Giving me the perfect excuse to be in the area, I could pretend that I wanted one of these for my dinner tonight.

Having parked up, I was able to see him enter the café before I entered the butchers, I mean these pies were expensive and no, I wasn't in the business of wasting money despite my advantageous financial position in life. But with my prey 'in sight' as it were, making such a purchase was the perfect excuse, so I entered the premises, and selected a steak and kidney variety of the many types available. Oh, and some 'home-made' scotch eggs too.

Duly purchased, I made my way to the café, clocking Simon sitting alone at a table, reading a book while he waited for his order to be cooked and brought to him. Pretending not to have noticed him at all until I'd ordered and been presented with a simple coffee. Turning around, this was the moment, as I suddenly exclaimed, "Simon. What a pleasant surprise!"

He almost seemed embarrassed at the sight of me, remember he'd recently split up with my daughter, for a reason that many people would consider perverse. He, quite naturally, tried to avoid my gaze, as he responded, no doubt hoping I'd simply go away, "good afternoon, Mrs Johnson."

But I was in no mood to let this 'fish' off the hook. "May I join you, believe me I'm in NO mood to judge." Nodding his, reluctant, assent as opposed to issuing an oral reply. So, I sat down in the chair opposite him, and took his hands in mine, an action with, no doubt, greatly surprised him. I guess that he expected me to be angry with him.

When he finally turned to my face I started. "Look I know that you and my Joan haven't worked out, and yes, I've heard her version of just why. I'm not going to interfere, and I accept that situation. But, as I said to her, you acted with total honesty towards her, not trying to deceive her or lie to her. In short you respected her enough to be completely straight with her, and so you've earned MY respect. Ok, so she didn't react in the manner that you'd hoped for, and to be perfectly honest I'd have probably done the same as her when I was her age. But I'm far older and wiser now, believe me I have NO problem with you." Smiling at him in the most welcoming way that I could.

"Besides," lifting up my skirt so he could quite clearly see that I was suspender clad myself, quite deliberately as you can all imagine, "wearing stockings and suspenders is utterly delicious. I can FULLY understand just why you feel the way you do about them, and anyway, why should it just be us girls who can delight in their pleasures?"

His eyes virtually bulged out of their sockets at the sight of my stockings, and his lips moved into a very revealing smile as I took one of his hands, placing it upon the sheer nylon covering my own pins. "I know Joan sees things differently, but, believe me, so far as I am concerned there's nothing wrong with you, and nothing for you to be ashamed of by wanting to taste the utterly beautiful feel of nylon on your own legs."

However, for now my seduction plans needed to be put on hold, as a waitress arrived with his food, which I allowed him to eat the majority of in silence, just gently sipping on my coffee in the meantime.

And then, as had been my intention all along, but giving the impression that it has just occurred to me, I beamed a welcoming, warm smile in his direction, and simply asked, "are you busy this afternoon?" It was time to get serious, time for the business of this day.

"No, not at all, Mrs Johnson. Have you anything in mind?" From my point of view, the perfect reply. Game ON, it appeared.

"Well, whilst I am busy, but that isn't until another hour or so," mustn't appear to be TOO keen. "Time enough for you to come around to my home and for you to try on some of MY stockings. Up for it?"

The look of sheer and utter delight upon his face told me all that I needed to know, I'd hit the jackpot alright! "Really? You're not playing some sort of game here, Mrs Johnson?"

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"No, Darling I don't play games with other people's feelings. I'm serious, if you wish you're welcome to come to my place and see for yourself how wonderful sheer nylon can feel against the skin of your legs. Oh, and don't worry, I'll be telling NOBODY, particularly Joan. It will be strictly between us; you CAN fully trust me here. One more thing though, less of the 'Mrs Johnson' please. My name is Elsie, I'd like you address me as such, especially if you're going to accept my genuine offer. Which comes with NO strings attached, by the way, I'm not demanding or expecting anything from you in return. Just the satisfaction that comes from helping another human being."

Come on, was there the slightest chance that he was going to refuse? Not a hope in hell! The look that I received in return for my offer was purely and simply a total joy to behold. "Yes please, Mrs John.. sorry I mean Elsie. I'd love to come back to your place with you."

He didn't even bother to finish his meal, rising to his feet and following me to my car. Nor did we really speak at all during the ten minutes, or so, journey to my home. Nor when we reached our destination, wherein I took his hand in mine, as I led into my house, guiding him up the stairs and into my bedroom.

Going over to my, quite extensive it must be said, lingerie collection, soon I selected a suitable satin suspender belt, and then a set of sheer nylon stockings. And a set of my, very skimpy, satin panties. Handing them out to him, "do you want me to leave in order for you to have some privacy? Or would you like me to stay and help you get into these? Don't worry, I was a married woman, and so I've seen it all before!"

I wasn't sure just what to make of his reply that he'd like me to stay. Sure, it meant I'd earnt his trust, but I guess that it also signified that sex with me, although clearly not my aim today, wasn't on the agenda. I was his ex-girlfriend's mother, obviously old enough to be his own.

That actually suited my purposes, as I was playing the 'long game' here. I'd completely lied to him about the need to be somewhere else this afternoon, not putting any pressure to go to bed with me at all on him this day. Although, that was exactly what I wanted, and with him not just ON it, by the way, I knew I had to take things steady, for the aforementioned reason, if nothing else. I had to entice him, break down his resistance, bit by bit. And that would take time, I fully accepted that. And, although those internet 'women' made things look so easy, remember I hadn't played the seduction game for quite some time now. Well over twenty years in fact.

So, apart from removing my leather jacket, and that action was purely down to the relatively high temperature inside of my house, I made no move whatsoever to take off any of my clothing, no doubt reassuring my target, that if sex was off his aims for the day, it was absent from mine too.

Therefore, I simply sat on my bed, offering to help him in any way, but making it crystal clear that I wouldn't act unless he asked me to. Soon he was absolutely naked, and once he'd relieved his body of his own garments, it was time to adorn himself in mine. With me clocking but making no comment at all, his reasonably sized cock, about six inches, or one hundred and fifty millimetres for those who deal in such units, in length.

He went to grab the panties first, and now I did intervene, if only in the form of words and not actions. "Put the suspender belt on first, Darling, it's best to feed the suspenders UNDER the panties." Lifting my skirt, leather to match my jacket incidentally, to show him that's precisely what I'd done myself. "You never know, you might well meet a woman who, unlike my Joan, accepts you in stockings and wants the panties removed!" Winking at him, who took it that way it was NOT intended, as a joke and not a hint! Never mind, it was still early days, and he did indeed follow my advice, putting on the belt first, and then the panties.

As he grabbed one of the sheer stockings, it became abundantly obvious that he didn't have slightest clue of how to fit it correctly, forcing me, apparently reluctantly but in reality, nothing of the sort, to intercede. "Sit down on my bed, Sweetheart, and I'll show you how it's done."

I rolled the stocking upon itself, in the time-honoured way, putting over his toes, and then, in the normal, pulled it over his foot and ankle, gently up his leg, where I left him to attach the suspender clasps. This was a bright and intelligent lad, he'd paid attention and made a very fair job of fitting the second stocking himself, managing to do so without laddering it at all, and bear in mind Ladies and Gentlemen, that I do NOT purchase cheap stockings that are not sheer, ever. He was fully ready.

Simon's quite a good-looking lad at the best of times, and to both of us this was one of those occasions. Getting to his feet, delighting in the utterly delicious feel of sheer nylon on his legs for the very first time, I considered him to be an absolute joy for my eyes, and my wet pussy come to think of it. Oh, how I wanted to undress myself, and take him to bed, right there and then? But I managed to stop myself, just where the self-control came from, I've NO idea!

Instead, I had him pace up and down my bedroom, taking out my 'phone and taking a snap of him, dressed thus. But not before asking him if I could, having assured him that, completely honestly, said snap was for my own private viewing only. Also asking him for his own number, which I dialled immediately. Why, when he was in my own bedroom, about two feet away from me? So, he'd have my number in his possession, of course, I wanted him to be able to contact me in the foreseeable future.

Because now, after a period of roughly ten minutes, I lied to him, stating that I, untruthfully, needed to go out myself, making him remove my lingerie and put his own clothes back on. Whereas I could have simply allowed him to keep it on and place his own apparel over it. Why?

Because then if he wanted to taste the delicious sensation again, he'd be able to do himself, and wouldn't need to come into my 'parlour,' as it were, again. Whereas I wanted him to begin to associate ME with wearing stockings, accepting my home as the only place he could do so, and not be mocked, judged or any other negative reaction. Hopefully, at some stage in the future, be shagged instead! Shagged in the manner of MY choosing.

Why hadn't he simply purchased his own stockings and suspender belt, I hear you ask, a not unreasonable question, it must be said? I could only speculate here, but I guess he'd considered them as FEMALE items, only being allowed to be purchased by a woman, and he felt the need of a female partner when he indulged, as it were. Well, if that was the case here, then I wanted ME to be that female.

So, then I replaced my jacket over my form and ran him home, pretending to then depart, for my imaginary rendezvous. Instead, I returned to my bedroom, stripped down to my lingerie, and pleasured myself with my favourite vibrator. Would my 'fish' take to bait? Oh, and just to 'tie up the loose ends' as it were, I did have that steak and kidney pie for my evening meal that day. Utterly delicious it was too!

I began to wonder if my plans had been fruitless after all, as Simon kept me waiting until the Thursday evening of the following week, before his call came through. But as soon as it did, I knew that it was time to move on to the next stage of my planned seduction of him. I responded to his request to visit my home again, to be placed within my lingerie once more, by informing him to perform all of his necessary chores, BEFORE he came around to my house. Because, as I informed him, I had nowhere to go upon the following Saturday, and he could stay for a long time, even overnight if he so wished. Oh, he was going to, make NO mistake about that!

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