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Sissy Maid story

 

 

I'd always known Roger was a cross-dresser - well, I'd known for the last twelve years, anyway. I wasn't impressed, to say the least, when I first found out, but over the years, it sort of faded into the background, and it became something I could accept without worrying about it. Once Roger understood that I had no real desire to see him in when he was all tarted up, he did it only when he had the house to himself. He did once try to persuade me to allow him to wear a nightdress in bed, but it didn't work for me, and he soon gave up on that notion.

 

Roger was a good husband in most ways, but it had always irked me that I was the one who had to do all the housework, in spite of the fact that we were both in full time jobs. A year ago, Roger was suddenly faced with retrenchment, which would have been a dreadful blow to him, but he managed to do a deal which saw him kept on for three days a week at a reduced salary. He tried to get consulting work to help make up the difference, but without much success. So he found himself with time to spare; he re-decorated the house, tidied up the garden, and dealt with several tasks he'd been putting off for years, but eventually, he often found himself at a loose end with nothing much to do.

 

Well, I guessed what he did do, of course - he spent more of his time dressed up, didn't he? As he did admit. So I put my foot down, and insisted that he did his share of the housework, now that he had the time. His share being most of it, naturally!

 

I should perhaps explain that Roger's wardrobe - his 'feminine' one - was very limited. As far as I knew, he only had three or four outfits of his own, all of which were definitely 'after-5'. Apart from them, he had a few of my old dresses and skirts, and it was these he wore every Wednesday, (his 'free' day), to do the housework. I wasn't overly concerned. As long as it kept him happy and he did the work, who was I to complain? And he did do very well. The place started to look much better kept, the laundry and ironing were always up to date, and my life was suddenly a good deal easier. I told him how pleased I was with my new housemaid, and he seemed terribly grateful.

 

This had been going on for several months, and as far as I knew, it had remained a private matter that nobody else knew about. I certainly hadn't told any of my friends. But one day, I accidentally let it slip out. Because it had become such a routine, I'd come to accept it as perfectly normal, and forgot myself. What happened was this. I was visiting Betty, an old friend of mine. Betty was a widow, who made a living as a dressmaker, and was very clever with handicrafts, making children's and doll's clothes. I was admiring some of her doll's costumes, and, seeing one doll in cap and pinafore dressed as a maid, remarked thoughtlessly something like, "Oh, Roger would love that !" As soon as the words were out, I realised I'd let the cat out of the bag, and tried to cover up, but Betty, raising her eyebrows, inquired, "What do you mean, Carol? I didn't know Roger collected dolls?"

 

Flustered, I couldn't reply immediately. But then, I thought, to hell with it, Betty and I are old friends, so I told her, explaining that now Roger was no longer working full time, he'd agreed to be my housemaid one day a week.

 

Betty certainly seemed surprised, but she took it in her stride. "How wonderful!" she exclaimed. "I suppose you make him wear a dress and apron?"

 

Jokingly said, and giving me a way out, in that I didn't have to admit that Roger was a habitual cross-dresser; I could simply have pretended that he merely did the housework, nothing more. But I had the feeling that she wouldn't have believed me! So I told her straight, that it was Roger's choice; he'd told me that if I insisted he do 'women's' work', then he'd wear a dress while doing it.

 

"Really? Oh, don't be embarrassed, my dear, it's not at all uncommon, you know! It seems that lots of men want to play at being maids!"

Roger had told me as much, so it wasn't news to me. "Well, maybe so, but how do you know?" I asked her.

 

"Well, this might surprise you, but Roger's not the first man I've met who likes women's clothes, you know. There was one gentleman, in fact, who got me to make several dresses for him, a couple of years ago. One of those was a maid's outfit, actually! It was a beautiful little dress, black moire taffeta, with a little frilly apron, and a frilled cap and cuffs. I never saw him in it, mind, but I'm sure he would have looked just cute!"

 

Coming from Betty, this was pretty surprising, I must say. But it was a relief to know that I could share Roger's secret with an understanding friend.

 

Betty didn't pursue the subject, and we went on to talk of other things, but as I was preparing to leave, she brought it up again.

 

"Carol, it's Roger's birthday next month, isn't it?"

"Yes, on the 23rd, why?"

"Well, as he seems to be doing so well in his housemaid role, don't you think he deserves a reward? Would you like me to make him a proper maid's outfit?"

"Oh, Betty, I don't know about that, I'm sure! Roger would be so embarrassed knowing that you knew his little secret........of course, I'd pay you for it, but..." What was I saying? Did I really want to see my husband all dolled up as a French maid?

"Oh, Carol, don't worry about paying me! It would be worth it, just to see him!"

"See him? You mean, you want to see him yourself?" I asked.

"I want to be there when you give it to him! It will be a birthday surprise! I'd just love to see him dressed up as a maid!"

 

I shuddered to think what Roger's reaction would be to this. But Betty persuaded me that it would work out beautifully, explaining that while men like Roger profess that they'd prefer their dressing to be kept secret, they fantasize about being exposed and humiliated, which is apparently a big turn-on for them, so that springing the sort of surprise on him that she was proposing would be bound to thrill him, whatever he said at the time.

 

I couldn't help but wonder how she could be so sure that she understood 'men like Roger', but I said little to dissuade her. It was a nice idea, to give him a present of a proper outfit, in place of the rather tired old summer dress he was using, and I was sure he would love it, but letting Betty actually see him was another matter entirely. I hoped that when the time came, I'd think of some way to discourage her.

 

Over the next few weeks, Betty checked with me regarding Roger's size and measurements, assuring me that his outfit would be ready for his birthday. "What have you arranged for that weekend?" she asked me, "Anything special? Going out anywhere?"

"No," I replied, "we don't generally make much of birthdays. We'll just be at home, as usual".

"Well, how about I drop in on you on Saturday afternoon, for our little surprise?"

"Betty, I really don't think that would be wise", I said, "Roger might get really upset - angry, even - I just don't know how he'll take it....."

 

"Oh, Carol, relax darling! Trust me! We won't do anything to upset him! Look, what we'll do is this. I'll give you his outfit beforehand, and you can give it to him in the morning, as a gift from you - which, of course, it is. If he asks where you got it, you can tell him I made it - no harm in that, surely? We're good friends - Roger knows it'll go no further. If he really blows his top, you can phone me, and I won't come. But remember - he might well put on a show of being embarrassed, but secretly, he will be thrilled, I assure you! He'll be so grateful to you, you see!"

 

"Well, I hope so," I said, not at all sure.

"He'll be just dying to get into it, I tell you. But either way, whether he does or not, I'll turn up early afternoon - if that's all right? - and if he's not already dressed in it, I'll see if I can persuade him to model it for me! How about that? He'll know already that I made it, so he can hardly object, can he? The worst he can do, is refuse - but I think we might be able to overcome any reluctance, don't you?"

"I'm not at all sure about that - Roger can be infuriatingly stubborn", I said.

"We'll see, then. Like to make a bet?"

I laughed. "No, I don't think so! But I'll be fascinated to see how you make him do what you want!"

Betty winked. "You'll see! Oh, I can't wait!"

 

Roger's birthday finally arrived. I gave him the usual token gifts that we marked our birthdays with - aftershave, a smart shirt, a bottle of single malt scotch (ouch! what a price that stuff is!). And then, with some degree of trepidation, I handed him the large, soft parcel containing his new outfit. "For you, darling", I said, "as a reward for doing the housework so diligently for me!"

 

Giving me a searching look, Roger slowly unwrapped the parcel, revealing the shiny black taffeta dress, and the snowy white apron, cuffs and cap, trimmed with black ribboned eyelet lace. And a full slip as well - with several layers of stiff taffeta and net, belling out like a tutu. I do believe he was blushing. "It's - beautiful! How did you know - but of course, not hard to guess, I suppose - but where on earth did you get it? It's so well made", he said, carefully inspecting it all.

 

"Actually," I said, heart in mouth, "I got Betty to make it for you".

"Betty!" he exclaimed, You mean - you told Betty!....."

"Oh, don't be angry, Roger", I pleaded, "I didn't exactly tell her - I just accidentally let it drop that you were doing the housework for me, and she - well - it was her idea - to make you a dress, that is - she won't tell anyone, believe me - "

Roger groaned, "Oh, lord, I suppose everyone and his dog will know all about me before long..."

"No, Roger, they won"t. How long have we known Betty? Twelve years at least? She won't let it get out, she promised ..."

"Oh, well, nothing to be done about it now, anyway", he said, "And it's a lovely thought. thank you, darling! Almost too good to wear for working!"

Relieved, I hugged him and we kissed. "Yes", I said, "Too smart for everyday. You'll have to keep it for best", - jokingly - "for when we have visitors!"

He gave me a playful slap. "That'll be the day", was all he said to that.

So - first hurdle overcome. No need, then, to put Betty off.

 

The morning passed in the usual way - some shopping, cleaning the car - but I could tell that Roger was itching to try on his new outfit. So, after lunch. I suggested he do just that. "Go on", I said, "I'm longing to see how you will look as a proper maid!"

He feigned reluctance, for form's sake, but made only token resistance. I sent him off to the bathroom to shower, shave and do his make up. As I'd hoped, Betty arrived while he was still in there.

 

"Well? How's it going? Has he?...."

"Oh, yes, Betty, he loves it! In fact, he's in the bathroom now, getting ready!" But actually, all had gone quiet in the bathroom. Hearing a visitor, Roger was keeping quiet, as he always did to avoid being caught out. "It's all right, Roger", I called out, "It's only Betty!" Only! I could imagine Roger's face!

 

Silence from upstairs. "Give me a minute", I said to Betty, "I'll try to reassure him before he takes fright and undoes all his make up. Make yourself comfortable."

I went upstairs and tapped at the door. I found Roger, fully made up but looking decidedly nervous. I smiled. "Come on, dear, you might as well, now. Betty would so like to see you...."

"I bet she would," he replied, "Oh, heck! What are you doing to me? All this - It was supposed to be strictly between ourselves! You know that! Why did you have to let Betty know?"

 

"I swear, I didn't mean to", I said. Well, truly, I didn't. "But if I hadn't accidentally spilt the beans, you wouldn't have that cute little outfit, would you? Now come on, put your wig on, and that black robe you have, come down to the lounge and let's see you! Surely you're tired of having to hide yourself away, aren't you? Now's your chance to show us how nice you look, and we promise we'll be nice to you! It's your birthday, after all!"

 

It took a little more cajoling, but I sensed that what I'd said did have some truth - he was frustrated at having to keep hidden, he did want to be accepted in the role he'd chosen. So while he finished making himself decent, I went down to Betty, and gave her the 'thumbs up'. "You were right! He'll be ready very soon, then he'll be coming down!"

Betty was delighted. "What did I tell you? Oh, this will be fun!

 

 

 

 

 

Hesitantly, Roger made his entrance. Betty slowly appraised him, and with a wide smile, said, "Very nice, Roger! Make up a little bit overdone, perhaps......but I must say, I don't think I'd even recognise you unless I knew! But what should I call you? Surely I shouldn't be calling you Roger when you.... when you're a maid?"

 

Roger was so nervous he lost his voice at first. "Ahhh....I......haven't thought about it, actually", he finally came out with. "Hmmm - we'll have to remedy that! What do you think, Carol, have you got a name for him... I mean, her?"

" Come to think of it, yes, I have. For some reason, I think of him as 'Rosie' ".

"Rosie? Yes, that suits. Well, then, Rosie," she said, turning to Roger, "I've a little present of my own for you, sweetheart. But first, you must let me see what you're wearing under that gown!"

 

Roger looked uncertainly toward me. "I - I'm embarrassed", he said, surely you don't want me to...."

"Oh, come on, dear, just sit down on that stool and lift your skirts, there's a dear, we're all girls together now, aren't we?"

She gently steered him over to the stool, where he obediently sat, and raised the hem of his robe, to show his frilly black knickers.

 

"Wow", Betty said, "what nice legs you have! And I love those wedge heels. Much more practical than stilettos! And what gorgeous frilly knickers!"

 

Roger didn't know where to look, unsure whether Betty was being sarcastic, or genuinely nice. Come to that, I wasn't sure, either.

 

"Now, here's my little surprise for you!" Betty declared.

From a carrier bag she drew out what looked like a little doll's ballerina tutu, all fancy and frilly in white and pink. I was mystified as to quite what this was about, and I could see Roger was, also.

 

"See - a little dress for your willy!" she exclaimed, and before Roger could react, she pulled down the waistband of his knickers and grabbed his penis!

"Betty!" I shrieked, "What are you doing?" Roger's jaw had dropped, words had failed him. He tried to pull away, but Betty had a firm hold.

 

"Ssssh, now, it's quite all right" Betty said softly, "All I'm doing is dressing up your little willy in a pretty little dress of its own - see? Every sissy husband needs a willy dress! Don't worry, sweetheart, I've seen it all before! Now, let me help you put this on".

 

I was flabbergasted. I thought I knew Betty well, but I'd never in a million years imagined Betty would come up with something like this. "How on earth..." I started to ask her, but she cut me off. "Don't ask, dear, but believe me, this is exactly what Roger needs, to make his position clear - and I can see he really wants it too! Look at him!".

 

Roger was blushing crimson, certainly, but seemed bereft of speech, as Betty slipped the tiny garment over his member, pulling the head right through, and fastening it with ribbons that threaded through several pairs of eyelets, like a little corset. As she tightened the ribbon lacing, Roger's member was remorselessly squeezed smaller and smaller, until it was scarcely fatter than his thumb. How could Roger let Betty do this to him without protesting, I wondered? Did he secretly enjoy it? Surely, he must! Or he'd never let her get away with it.

 

For that matter, what was keeping me silent? I was shocked to the core at Betty's extraordinary performance. She had finished lacing up the miniature corset now, and after passing the ends of the ribbon around Roger's stalk, tied them fiercely in a double knot.

 

"There - done! Isn't that pretty, Stephanie, sweetheart?" said Betty, as she rose. "That will keep you in order, now. No slipping away to excite yourself, when you should be hard at work! Now, tell me - how does it feel?"

 

Roger found his voice at last. "Tell the truth, I can hardly feel it at all," he said.

"Good! That's the idea! For the time being, you can forget you were ever a man. You're a sissy maid now, and that's the way you'll stay, until Carol decides she's had enough and cuts the ribbon to release you. You won't be able to untie it, as you can see. So you'll have to stay the way you are, neutered! You could cut the ribbon yourself, of course, but then Carol would know, wouldn't she? And you wouldn't dare do that without her permission, would you, my sweet? That's the way you want it to be, isn't it Rosie?"

 

"I suppose I must do" Roger mumbled.

"No, not good enough! This is what you should answer: 'Yes, madam'. Don't forget! Let's hear you!"

 

"Yes, madam", Roger repeated. I could hardly believe my ears. Roger had become a thoroughly cowed, obedient servant before my eyes!

"That's better! Now, let's get you properly dressed. Off with that robe, Rosie!"

 

Roger slipped off the robe over his head, revealing his padded corset, and a mound in his knickers where his member stuck out in front of him. He had also put on the white cuffs of his new maid's outfit.

"Right," said Betty, "Now, do you have a slip?"

"Yes, of course," Roger replied, and put on a brief black slip of his.

 

"Excellent, Rosie, and now if you put on your new petticoats, they'll cover that up that nasty little bulge nicely", Betty said, as she helped him into them.

 

They did indeed, being in fact a whole set of petticoats, stiffened taffeta and net layers alternating, which flared out widely from his waist, making them rustle loudly as he moved.

You could see that Roger really enjoyed them! He turned one way then another, admiring himself in the mirror over the mantelpiece.

 

"All right, then, Rosie, now for the dress itself. I know how much you're wanting to see yourself in this! So here we are - lift up your arms, please", and as he did so, Betty raised the dress over his head, and, guiding his arms into the sleeves, slowly let it settle down around his waist. Roger was quite overcome, I could tell. It was certainly a very fetching outfit, and while it may seem strange to say, I had to admit that somehow it really suited him!

 

Betty set to, and quickly completed his 'uniform', tying his apron in a neat little bow behind, and setting the frilled cap on his head. "There we are, madam", she said, addressing me,

"Your maid - to use entirely as you wish, to carry out your every command!" And turning to Roger, told him to curtsy, and promise to be obedient at all times and always to do as his mistress commanded.

 

"Rosie, you look just perfect", I said, "Don't you think Betty has made a marvelous job of that outfit? It fits you perfectly, doesn't it?"

"Well, yes, I must say it is beautiful", Roger replied, "A bit too good for actually working in, perhaps..."

"Oh, I'll find plenty for you to do that won't risk spoiling your dress, don't you worry! But I can't believe what Betty gave to you as her 'little surprise'!"

"Nor can I", said Roger, with feeling, "I'm absolutely shocked, Betty!"

"Don't be", she replied, bluntly. "I've learned a thing or two about men like you, believe me. And squeezing your willy into that little tutu is just the thing to keep you in your place while you're pretending to be a woman! Stops you from getting naughty ideas! Bring it out for us all to see, as a reminder!"

Roger stared at her. "Bring it out? What do you mean?"

"Show us your pathetic little willy, that's what I mean!", said Betty, mockingly.

"You mean....." said Roger, fumbling with the hem of his dress.

"Yes, that's right! Lift up your skirts, sissy maid, drop your drawers, and show us your little dolly!"

 

Slowly, awkwardly, Roger groped beneath his petticoats, found the waistband of his knickers, and drew out his preposterously befrilled member.

"That's right. Now, Rosie, tell us: what are you?"

"I'm a maid", he whispered.

"Not just a maid! A SISSY maid! Tell us!"

"I'm a sissy maid" he replied.

"Louder!"

"I'm a SISSY maid!"

"You certainly are, and no mistake! Anyway, you look just precious, darling," I said, "And now we'd like afternoon tea, Rosie, if you please?"

Roger looked blankly at me for a moment, before he realised what was expected of him.

"Yes, madam,", he replied, dropping a curtsy as he turned to leave the room.

Betty and I exchanged wide smiles.

 

It would have been lovely if Roger had remained as willingly obedient, but after only a few weeks, he began to complain, would you believe? After all the trouble we had gone to! See what happens when I told Betty that he was beginning to show signs of rebellion!

 

  

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