The Haberdasher Ch. 02

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In which I discover how domineering older ladies can be.
5.2k words
4.26
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Part 2 of the 2 part series

Updated 09/22/2022
Created 05/25/2013
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Warning this story was written in England by an Englishman. It utilises English vocabulary, spelling and grammatical conventions; some readers find these disturbing.

*

Annabelle, a woman almost twice my age, had finally managed to seduce me at a dinner party. Once circumstances permitted us to slip away to her home, she had revealed just how unbridled her lust really was. That night her desires were apparently insatiable, her fires unquenchable. I could, of course, tell you about the rest of our weekend. The party was on the Friday evening, we woke up in bed together on the Saturday morning. Following some utterly delightful oral sex, as pledged the previous evening, Annabelle made it abundantly apparent the she knew that my diary was completely clear until the Monday morning and so was hers. She had arranged the almost impossible, a Saturday off work for herself: revealing that the little minx had pre-planned her assault. A recounting of what followed between us that weekend would be lewd and crude to the point of indecency but would also be repetitive, predictable and ultimately, dull.

As a compromise I'll précis. She took me on a tour of her house and we exploited the various features found in the different rooms to explore the pleasures of an extensive variety of sexual positions. You know! You liar! Oh yes you do. Coffee tables are really good for doggy. Kitchen worktops are the perfect height for her sitting, you standing. Easy chairs; she splays her legs over the arms, you kneel and... And well; finger, lick, screw and try combinations thereof. Bathrooms, we spent a long time in the bathroom, well: shower, bath, bidet; I ask you, the possibilities are and were endless.

The cellar was a bit creepy but it's quite amazing what you can do with a saw horse and a woollen blanket for padding! We also spent a prodigious amount of time exploring the many possibilities for a man and a woman to couple when supplied with a well padded saw horse. Naturally bed was best and she owned, at the very least, three of them. We allowed ourselves, at the least, one different position in each, most of them two; no I tell a lie, all of them at the very least two. My favourite was reversed cow girl. Annabelle's favourite was on her back, knees to her chest. For a woman in her forties Annabelle was amazingly flexible, unbelievably fit and improbably inventive: what I had failed to take into account, at that point, was that she was also very, very practised.

It was the following Wednesday evening, when Annabelle had suggested that I should return and, once again screw her silly, that our relationship evolved dramatically. I arrived all youth, eagerness and enthusiasm. In contrast, she was reserved and hesitant, almost shy. As we passed the open door of her dining room I noticed that the huge dining table was, quite literally, covered in papers. She intercepted the direction of my glance. "I was doing the books. I'm a bit down tonight; actually I'm bloody well depressed. Sorry but no matter how I work it, slowly but surely I'm going to go under. I'll last a half a year, perhaps a little more, but after that..."

"I can profile your accounts on the computer." I interrupted, rudely. "You can make savings; that's what I do! Everything will be alright," I chirruped, all upbeat and assured.

"It won't," she snapped back. She was trying not to cry and the effort of restraining herself was causing her to lose her temper.

"Tell me!" I was far too abrupt with her.

"You think you can do anything?" She snarled back.

"I can't if I don't know what the problem is." I softened my tone and took a deep breath, "maybe I can't, even if I do know what the problem is but at least I can listen."

"You must go. You must go right now. You can leave with the satisfaction of knowing that you have given me my best memory ever and that I'll never ever forget you." Her shoulders began to heave. She was sobbing quietly, yet trying her very best to suppress her all too evident distress."

"For God's sakes tell me!" I railed at her. "It's no skin off my bloody nose and you should realise I'm not stupid either. Take a break, spill the beans, open some wine and get it off your chest." I had lost it, "It would be best if I went wouldn't it?"

"Yes you damn well ought." My heart sank. "But only after I've opened the wine and we've drunk a stupid toast: I don't love you but I do want you, I desire you, I need you." I knew exactly how she felt. So whilst I sat, she shrugged and slunk off dejectedly to the kitchen. I was in despair. All my previous relationships had been fun and frolics, sex, light-hearted and fancy free. Full of meaningless decisions. Go out and screw later or to stay in and screw now? A weekend in Bath, or dinner for two somewhere really posh? The biggest crisis was when a girlfriend had skipped a period after she had gone on the pill. Not unusual, but at the time it appeared to the pair of us monumental. A potentially life changing concern, enduring an enforced marriage in wildest suburbia. But none of these experiences had prepared me, a lad of three and twenty, for coping with real life intruding upon sensual pleasure, sexual or otherwise: previously the two had always been easy to keep in their own, individual, isolated bins.

We sat in her spacious sitting room. Large glasses of fine wine in our hands, not white, nor red nor even rose; a dry (trocken), orange coloured wine from Germany; a wine with a happy sunshine on the label. At least something was happy, even if was only a cartoon. "What shall we toast? What ough't we cheer 'afore we pair of hapless lovers submit ourselves to the cruel and pitiless jests of the cruel fates."

A smile played upon Annabelle's quivering lips. She paused as she considered a rejoinder. "Prithee, good sir. Tarry a while longer; sup deeply and mayhaps join me in a second cup? And I? At thy command I will attempt to reveal the roots of my despairs."

It was my turn to laugh. By far she was the more accomplished of us at delivering cod Shakespeare; more conversant in its pleasantries and strictures. More ominously, I failed to realise, far quicker thinking than I could ever hope to be. This exchange also exposed the fact that, despite the disparity of our ages, we shared a common educational background: she at the beginning of its era - at least for girls - me near its end. Best of all, the ice had been broken. Annabelle was, once more, calm, composed and relaxed.

"My shop doesn't really make any profit these days. No one makes their own clothes now. We make our money selling wool and knitting patterns and women are now giving that up too! And it's getting worse. Things cost less and less and your staff request more and more. It's cheaper to buy ready made in a big store, from India, than make it yourself! Made in Hong Kong, made in Japan, I simply can't compete. I've been running the shop to keep my staff in a job for two years now. Two of the girls; well, their husbands are out of work, it would be a body blow if they lost their jobs."

Just to set things in context, 'her girls' were mostly in their forties and fifties, one in her sixties. 'The new girl' had been there for two years and would remain the new, idle girl till a new 'new girl' was hired. At that point the old 'new girl' would be promoted to the position of 'that lazy fat trollop' and all the other girls would shift up the ladder one rung. It also made me laugh because the current 'lazy fat trollop' was as skinny as a bean pole and a real grafter.

"It'll be the same for you soon, either Briggs and daughter will be the biggest distributors in the country or you and your boss will be looking for work yourselves! Why do I go to those shitty evenings that culminate in sordid wife swapping? I'll tell you why! It's because I'm as subjugated as you are. You have to humour Maurine and I have to humour those bastards because those are the bastards who prop my shop up. They order kinky stuff, occasionally for their wives, but more generally their lovers. I design and sew it and they pay for through the nose for it. Don't get me wrong. I'm grateful to you in ways that have nothing to do with last weekend. If it hadn't been so fulfilling, I would wish that last weekend had never happened so we could carry on like before. Don't fret, it was my best sex ever, you little donkey.

Anyway, when you appeared regularly upon the scene all the leering suggestions of threesomes vanished, thank God. No. 'I'll design and manufacture kinky costumes for you and your downtrodden wife or lover, Mr. ghastly-wife-swapper. And yes the costumes are outrageously expensive: but even so you don't get to fuck me as part your squalid little deal.' Customers like that, they think they are someone, they don't like to hear that. And their wives. Many of those poor dears begin to find 'girl on girl' is a delightful luxury! They're not even real lesbians, they just fancy pleasure that's pure, unsullied and, above all, considerate of their needs and wants."

"I asked, you explained to me." I gulped my wine, which was a travesty because it was truly excellent and deserved to be sipped slowly and with due appreciation.

"The girls in my shop, they used to sit. Now they sit and sew, sometimes crochet; the most able are learning to make lace. But I cannot obtain enough orders to keep us going for ever. I need to branch out."

Dejectedly, I realised that I could not really help Annabelle. What did I know of kinky knickers, wife swaps and stuff like that? Wryly, I reflected that I didn't even have a wife to swap, and even supposing that I qualified for a driving licence, it did not sound like Annabelle would be even vaguely interested.

"Is there any good news?"

"I did have lots of orders for Christmas presents and they're just about all done so I can carry on until February. After that, unless we find lots of men looking for Valentine's gifts, I'll have to start letting staff go. I've worked so hard for all this," Annabelle cast her eyes round the luxurious room. "Unless something happens, in a year or two, it'll be back to flatland for me and no jobs for my staff. I can live in flatland but I'm not some shitty male executive, I care about my staff!"

I was flummoxed. "Branch out. Do new stuff. These bored, kept women and even more, the even more bored hapless wives of the men who want threesomes. You make kinky costumes for them and they wear them; perhaps they even get some pleasure from wearing them. What do these women really want? Cater for that!"

Annabelle came over, squeezed my cheeks between her hands and kissed me hard upon the lips. I relaxed, I had got something right. Tonight my lusts an desirers would be more than satisfied after all. I responded in kind. Annabelle was just so sexy and she now considered that I might just have hit the jackpot: my prize? A night of expectation fulfilled. I had missed the point utterly; I was planning the fate of my, by then. very stiff member in a seriously sexy lady for that evening alone. Annabelle had visualised a future: a future that offered financial security, financial safety and encompassed being able to sate her many lusts and diverse desires in perpetuity. I had yet to acknowledge that I was infatuated with a total siren.

"Shower and wash their bodies, wash their hair, manicure, pedicure, massage, deep massage," I did not like they way she eyed me as she said, 'deep massage,' but missed the point. "Hot baths, oils, perfumes, flowers, candles, we could offer all that."

"Champagne, chocolates, real tea, real coffee, rich butter shortbread," I intoned; a little clueless of what was happening but adding my perceptions of female susceptibility.

"Flowers; lots of flowers. We could charge a small fortune. Come I'll show you where." Annabelle led me to her cellar. The saw horse was still there, with the blanket still draped over it. The cellar had three obvious rooms one with two windows stood either side of a door that led to the garden and two spacious but windowless rooms behind. One with a big hole at the back. "That's the old coal hole, don't go in there tonight it's absolutely filthy. The other back room had a butlers sink and an ancient boiler on one wall and a drain in the middle. "This will be the shower and bath room," declared Annabelle. "The front I'll divide into a reception area and a sitting room. The other room will be the massage area and pamper space.

"You are brilliant," she enthused at me, "and you must help with other good ideas, that is if you want to."

I opened my mouth.

"No don't tell me now. Tell me later after we have played a little game together. If you want to keep on seeing me after I've had my fun tonight then you can help too. I'm a very demanding woman and not easy to please. But first you must go to the bedroom and I will go and put one of my costumes on before we play my little game.

When Annabelle entered her spacious bedroom she was modelling a broad green choker, a tight, leather and satin waist cincher or waspie and green high heels. The foundation of the waspie was constructed of dark brown leather, the panels, they were covered in dark green satin. The edges of her overtly sexual creation. were trimmed with dark green lace. The cups pushed her breasts up to make her cleavage seem vast, yet left her tightly puckered, dark red, teats bare and very ripe for sucking. The waist was ridiculously tight, apparently she had a little machine to help with that. The bottom was cut so that the entire length of her slot, from the top of her pubis to the beginnings of her tail bone, was wholly accessible. Occasionally, little strips of braided leather were worked into the main strips; from one of these, set low and round the back, dangled a thin black leather covered rod that ended in a short leather strap.

I was transfixed by the outfit. "This is mine. I use it to explain my talents to potential clients. Don't worry the cups are usually adjusted so that they are a little less revealing and I have some green lacy panties. briefs to die for, to go with the costume. I nearly put them on; their gusset is cut and shaped perfectly so that you always think you're going to see just a little more as I bend but actually you never do. For outdoor use, under clothes of course, I have a similar pair of panties but with a built in dildo which really makes sure they stay in place. The choker I leave off outdoors but here" and she strutted across and raised her chin so I could see the solid gold strip that ran along the fabric. It was engraved with a single word, "Mistress."

"There's hours of work and I can sell them for:" here's a problem, the sum she named would, today, sound trivial, but then it was a fortune. Annabelle could charge the equivalent of the salary of a middle manager for about a week and a half's work but then, it took about that long to make them. She didn't do all the work herself, naturally. She sub-contracted and took a good profit but it gives you an idea.

"Now does little doggy want to play with mistress?"

"Oh, yes please, woof, woof." I pretended to wag a non-existent tail.

"Bad doggy. It's yes please mistress, it's always mistress." She unhooked the rod from her costume and slapped against her palm, ominously. "Now, do doggies wear clothes?"

"No mistress," my already stiff member pulsed with blood and anticipation.

"Well get undressed and, puppy and be quick about it unless you wish to incur my wrath."

"Yes mistress," I said as I began to unbutton my shirt. As I removed the rest of my clothes Annabelle strutted over to the door and picked up a small box I vaguely remembered her bringing it in with her. She carried it over to me and opened it. Inside was large dog collar and a leash.

"Good doggies wear a collar. Here's yours. Read the inscription then put it on."

The tag was engraved on both sides: one said 'sex toy' and the other 'property of Annabelle Jenkins.' I donned the collar and intoned, "thank you mistress."

"Now what's this? Bad doggy." She grabbed my stiff penis and rolled my foreskin back as far as it would go.

"Oh mistress," I gasped with obvious pleasure.

"Never mind, 'Oh mistress,' how dare you point your pathetic little piddle stick at your mistress and then allow it to bob up and down like a cork. On your knees you impudent puppy. You must be taught a lesson. Listen puppy, at all times I demand respect. I'm not some common little mongrel bitch who's fanny you can sniff at. Near me you will look at the floor puppy. Can't you read? You're a sex toy: your only justification for existing is to give me pleasure. Lot's and lot's of pleasure. So don't you dare presume to admire my figure like that."

"No mistress. Sorry mistress."

"No your not, that cock's still bobbing. How's anything that excited going to give me a long slow sensuous spearing. It'll spurt and spew its smelly secretions in a second leaving my swollen slot slavering and unsatisfied."

There was a strange swish, liquid fire raced across my buttocks. I sprang up, "fucking hell Annabelle that really hurt," I rubbed the affected area. "Jesus that was not funny, that really fucking stings. Shit!" it hurt like hell.

"Get back down you bad puppy. Down boy. Down, right this instant!"

I considered storming off right there and then, but yet again my cock was really aching with lust and my bum was already a little less sore. I dropped to my knees, resumed my doggy stance on all fours and gave Annabelle a second chance.

"Bad puppy. You were only supposed to get one of those. Just so's my little puppy wuppy would know what happens to disobedient puppies. Now potty mouth puppy will have to take a second stripe and this time 'thank you mistress' will be all puppykins will say."

That fearful swish sounded once more.

"Thank you mistress," but I could not stop a fat tear running down one cheek and I resolved that if she attempted a third blow I would, indeed, be off.

"Well my sex toy is a broken one. It's obviously totally useless as a phallus. It'll come so quick it'll tease me rather than pleasure me. Then I'll have to wait until it gets hard again. Then it might not be a lot better the second time around. Third time it probably won't be stiff enough to be a proper sex toy. Bloody useless puppy." All the while mistress strutted round and round my prostrate form but, much as I wanted to watch her magnificent figure in her leather and green waspie, I looked at the floor as instructed. Every time she passed my anal crack she gently tapped my scrotal sack with the leather thong of her switch. True this made my penis twitch with anticipation but I was terrified that she might increase the savagery of the blow leaving me doubled over with agony.

"That's a better puppy, at least you do trust me." Another tap to the balls, another twitch. "So puppy what's in working order?"

"Please mistress you could enjoy my tongue, that's fully functional. Good puppies love to lick their mistress."

"So I do hear." She tapped my dangling testicles just a little harder this time, sufficient to make me suck air in but still light enough to make my penis twitch in response. My poor balls were literally aching with lust, in the whole of my life I had never been more desperate to come than I was at that moment. Worse, Annabelle was cleverly blurring the distinction between pleasure and pain. That last flick should have simply hurt, not hurt a little but a lot. And, indeed, it had been painful yet it had also rendered me stiffer than ever.

"I suppose I could allow my little pet to pleasure me that way but, gosh, it will take ever so long. I hope my little puppy has a strong, tenacious tongue!"

I considered poking it out and panting but my buttocks were still on fire. Good little puppy had certainly learnt obedience.

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