Maude Ch. 01

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Maude dresses him up.
4k words
4.43
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23

Part 1 of the 5 part series

Updated 10/30/2022
Created 04/22/2007
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I walked into the second-hand charity shop and there she stood, behind the desk.

I knew she was called Maude when I read the identification badge pinned to her cardigan. It was a dark blue, v-kneck cardigan, under which she wore a pale blue lacey-knit sweater. Her face - now I noticed - was smiling at me, looking at her. She was in her late forties, I guessed, with greyish hair cut short, and was what you would call well built with a large frame and an ample bosom, hidden under the soft wool of her sweaters.

I wandered into the empty shop, looking at second hand books and trinkets, until I saw the clothes racks further back in the shop. Walking past Maude I smiled at her, and she smiled back knowingly:

"Just looking or can I help you?" she asked, in a well-to-do accent.

"Just looking thank you," I smiled back, my eyes dwelling on her beautiful large breasts, nicely rounded under the tight wool of her sweater.

From closer up I could just about see through the lacey pattern, with tantalising glimpses of pink skin and white where her bra showed through. Then I carried on walking to the back of the shop.

There my eyes saw the double row of sweaters and cardigans amidst the other second hand clothes. My mind raced. I couldn't resist looking at some, as if I wanted to buy them. But why? Suddenly an idea came into my head - I could be going to a fancy dress party, where boys had to be in drag and girls in boys clothes. It sounded good enough to me, so I studied the sweaters more closely, stroking them as I passed along the rack. Thinking that they could be Maude's sweaters, and how soft it would feel to stroke her huge breasts. I hardened a little at the thought.

"Are you sure I can't help you at all?" enquired Maude, breaking into my silent appreciation. She'd walked out from behind the till, and was walking towards me.

"Well... " I began, "I've got to go to a fancy dress party, and all the boys have got to be dressed as girls, so I though I'd see what clothes I could find." I blurted out my new secret.

"Well you've come to the right place!" smiled Maude, looking me in the eyes with her brown eyes. "We've got lots of things that might do - but you wanted a sweater did you? Or a cardigan?"

"Well I don't really know which." I answered, "But I thought that something on these racks might do."

"Hmm," said Maude, looking me up and down: "you'd need a large size if its not going to get stretched too much. Let's see - what about this?" and she unhooked a hanger with a white v-knecked cardigan on it, and held it up to my chest.

"This might do..." she said. "You'd better try it on to make sure it fits - then we can have a look at some others if it doesn't. There's a changing room just here, so why don't you just slip it on inside. I'll make sure no-one else comes in while you're undressing!"

I stepped towards the changing room, aroused by holding the soft white cardigan, and surprised by Maude's enthusiasm. I watched as she got to the door and turned the 'open' sign round to 'closed' before locking the door. Then I went into the changing room. It was only tiny, with a mirror on one wall, and two hooks on the other, and a flimsy brown curtain across the door. I took off my sweat shirt and put it on the chair, then heard Maude outside.

"Now how are you getting on?" she asked, drawing back the curtain. "Oh," she sounded disappointed, "I thought you would have had your shirt off by now!"

"Do I need to?" I asked, "Can't I just try it on over my shirt?"

"Oh, no, that wouldn't do, dear!" replied Maude, smiling, "You can't be a proper girl if you've got your shirt on under your cardy! Now just you get along, and I'll look out some more clothes for you - this is quite exciting, isn't it!"

As she went away I pulled the curtain back, and unbuttoned my shirt, leaving it on the chair. Then I took the cardigan off the hanger, and slipped a bare arm into the sleeve. It felt so erotic - and so tight as the soft, hairy wool clung to my skin. I felt myself twitch again. Then I overcame my embarassment and pulled it on completely. It felt really arousing, to be wearing a strange woman's cardigan, here in the back of a charity shop. I pulled the front of the cardigan together, and felt the wool stretch over my chest. Then I slipped a hand down my trousers to ease myself erect - it was that good.

Just then, the curtain pulled back and Maude peered round.

"How are we doing?" she asked, then without waiting for an answer she continued: "Well that looks fine! - and it fits you well, doesn't it? Now let me see..." and she came closer, stroking my arms and then patting my waist. "And a very nice girl you'll make, too!" she smiled - "Now give me a twirl!"

So I turned away from her, catching sight of myself in the mirror. Her hands started stroking my shoulders, and the twitching in my pants was growing more.

"Yes, that's fine," she smiled. "Now you take it off and I'll see if we can find some more for you."

As she left, I unbuttoned myself and slipped off the white cardigan. Soon Maude was back with a black mohair cardigan and a bright orange one in thin lambswool - witha tape measure in her hand.

"Right, well before you try on these, I'll just measure your chest to see what bra size you're going to need. You haven't got one already, have you?"

"Well, no." I blurted out.

"OK, err... I'm sorry, what was your name?"

"Andy."

"Oh that's nice - I know another Andy already, he's one of my favourite regular customers! Well just put your arms out and I'll run this tape around to get your chest measurement."

I did as I was told, enjoying the feeling of her warm hands against my skin, and the brushing of her soft cardigan as she move the tape to the right position.

"Well, just about here is under your boobs - and it's 38", just the same as me! You could wear my old bra's then, couldn't you? Which is very handy because I brought one into the shop only last week. I'll just go and get it for you."

So out she went, leaving me just enough time to ease my cock fully erect before she came back in again.

"Well here we are Andy - now just put your arms forward and I'll loop the straps on."

I did as she asked.

"Turn around now, please." she said, "and I'll see if it fastens properly. I'm sure you couldn't do this on your own!" She was so close behind me I could smell her perfume and her body, and felt a wave of arousal pass through me. She pulled the ends of the bra together and then did up the fastening. "That's good," she said, "It fits perfectly - fancy seeing you in my old bra! Now turn around for me."

So I turned to face her, as she slipped her fingers under the straps, next to my skin, to straighten the straps. The cups hung lifelessly to my chest.

"Yes, " she said, seeing my gaze, "We'll need some padding in there won't we, to get you looking like a lady." And with that she put her hands below her breasts and tugged down her bra, adjusting herself more comfortably under the wool of her sweater, pressing her breasts forward as she did. "This is what you need to look like, isn't it?" she said, and she folded her arms under her bosom, lifting herself up for me to see better.

I thought I should say something in reply.

"I don't think I could ever look as good as that!" I said, gazing at her breasts, then into her eyes. She had been watching my eyes on her chest, and smiled to herself.

"You flatterer!" she said, smiling and giving me a wink. "I know just what you need." And with that she went out of the changing room doorway, and rummaged amongst a display of tights. "Here." she said, after a moment, "Let's help make you a bosom!" So she walked back to me, and reached up to my bra strap.

Her warm fingers brushed my skin again as she began stuffing the tights and stockings into my right cup, until it began to fill up, then she moulded it carefully into shape.

"Mmm," she smiled, gently stroking my new breast, "That's getting better. Now for the finishing touch, then we'll do the other one." And she reached to the tip of my breast, and squeezing between finger and thumb, pulled out the bra and padding into a nipple shape. "There! How's that!"

"It's very life-like, I think." I replied, looking down on my amply proportioned breast. Maude returned to the display, and came back laden with more tights and stockings. Again her hand workd on my chest, pulling the strap out and filling the cup, before tugging and squeezing and pulling it into shape . Then she stood back to admire her handiwork.

"I think you've got one a bit bigger then the other!" she smiled, "but then again so have I, so I suppose that doesn't matter. Put your cardigan back on now, and button it up, so we can see if it all looks right."

I did as I was told, feeling yet more arousal as the wool again touched my skin, and more embarassment as she watched me buttoning up the cardigan over my well proportioned breasts.

"Well, look at yourself in the mirror, pet. I think you are looking quite the part!"

I looked and saw my face, transplanted onto a large woman's body. Then as I watched in the mirror, I saw Maude's blue wool covered arms reach out, and her hands stroked my breasts, carefully reshaping them as she did so. It looked just so arousing, and felt gorgeous too.

"That's about it, I think." she said, "Now, what are you planning to wear with it? A skirt? or slacks? or maybe leggings? No, but there again leggings wouldn't hide you enough now would they?"

I hadn't thought about the bottom half - only the cardigan.

"Well I could always sort that out later... " I said, "If you need to open the shop again."

"Nonsense, we can't leave you only half satisfied! and the shop can stay shut for ages yet - it's a very quiet day today. Now, I think that some sort of woollen skirt would look good, ideally with an elastic waistband - and come to think of it we've got just the thing! It's an old one of mine that I brought in last week. I'll just go and get it."

My mind was racing around the other aspects of wearing a skirt - like my huge erection. And how could I hide that with Maude so keen to help? Soon she was back, holding a plain mauve knitted skirt, which she held up in front of me.

"This will be just the job - then you'll be ready for anything at your party, won't you? Now, let's see it on. You'd better just strip off and leave your jeans on the chair. I'll draw the curtain for a minute."

So as Maude stood outside, I took off my shoes and socks, before slipping off my jeans and leaving them on the chair. I was wearing thin white stretch underpants, with my cock clearly visible as I pulled them up tightly. I tried to pull the cardigan down but I could see in the mirror that there was still a lot of me showing. As I was pulling the cardigan down, so Maude just pulled back the curtain. I must have quivered with surprise.

"No need to jump, dear, it's only me!" she smiled, then looked at me closely. "Oh you are a big boy aren't you? We might need to get a girdle to hold you all in... but for now let's just try this skirt on. I'll hold it out, and you step in. You can hold my shoulders to support yourself."

As I stepped forward into the skirt opening that Maude was holding for me, I put my hands on her shoulders and felt her body for the first time under the soft wool or her cardigan. Her head was down by my waist, I realised, and she was just staring at my cock, now throbbing under my pants. I quickly put my other leg in, and she pulled the wool of the skirt elastic up over my thighs, till it reached my balls and my bottom. It felt beautifully arousing, and as I looked down I could almost imagine her just sucking me off, her head was so close.

"Now one last tug and we will be there," she said, looking up at me, "You pull by your bottom and I'll pull at the front."

So as my arousal grew more, I put my hands behind my back to grab the waistband of the skirt, and watched as her hands did the same at the front, brushing against the top of my thighs as we both pulled the skirt up together. The skirt's waist band stroked over my shaft as she lifted it up, then she lifted my cardy up, staring at my cock until it was hidden by the skirt and the waistband was round my waist. I pulled the cardigan down, trying to hide the bulge at the front.

"That looks just lovely, dear," she smiled, "Now do me a twirl!"

So I turned aorund self-consciously in front of her, watching in the mirror as I did. The huge bulge of my erection was very obvious at the front of the skirt. And she had certainly noticed too.

"There's just one problem, "she said, looking ont my eyes, "and I think you know what that is, don't you. You just can't pretend to be a girl with one of those, now can you? I think we had just better get rid of this to keep your tummy nice and flat." And with that she rubbed her hand gently on my 'tummy' - the ridge of my arching cock. I nearly came on the spot, and gasped with pleasure.

"Oh I'm sorry, did I hurt you?" she asked.

"No, it wasn't pain," I reassured her, "just surprise, that's all."

"Oh, good," she continued. "Now, about this - " and this time she gently grabbed my erect shaft through the wool, "Are you going to make it go away on your own, or would you like some help?"

I must have looked amazed. "There's no need to look like that," she said, smiling coyly, "I know what you boys do in the changing rooms - I've seen the stains on the floor, and on the clothes too. Now if I help you, we can get rid of your swelling so your dress fits, without messing up anything. You just move to the back wall, and put your hands behind your head. You can watch in the mirror too, if you like." By now I could see she was quite flushed too.

"There's a good boy - or should I say girl!" she whispered, as I moved back as she had asked.

Her hands grasped the skirt waistband at each side, and she pulled the skirt down to my thighs, the front bouncing over my cock as she lowered it.

"Now let's see what the problem is..." and again she brushed her hand up the front of my underpants, along the length of my shaft, this time seeing clearly what she was doing.

I gasped in pleasure and she continued to rub her fingernails up and own my shaft, moving closer to me, then grabbing my balls firmly with her other hand.

"Oh look in the mirror!" she said, breathing a little faster too. "It looks just like we are two ladies if I hide your manhood with my arm - look!"

So I looked, and saw this amazing sight: me with a white cardigan stretched over my big boobs, tight white pants and a mauve skirt around my thighs. She with her dark blue cardigan now parted completely, her pale blue sweater pulling tightly over her breasts only inches away from mine.

"I think I should have a little peek inside these panties of yours, don't you, dear?" she asked, "I'll just help you off with them - you keep your arms behind your head like a good submissive girl!"

And saying that, she pulled at the waistband of my pants, easing it over my cock and lowering my underpants to my thighs too. Now my cock was free and fell forwards, pulsing upwards as I clenched my thighs. She looked at it and smiled, then looked up at me.

"You just be quick please, and I want no mess on the carpet!"

And with that she put one hand under my balls and the other round my shaft. The feeling was just electric as her skin touched mine. Then she started a gentle pumping up and down my cock.

"But.." I began, "I'll cum if you do that!"

"Oh good," she replied, I was rather hoping you would - we can't have a girl with a big cock now can we? Now just you watch in the mirror!"

What I saw was just too amazing, as in one view it was two mature ladies, standing close with bosoms almost touching - and yet below the waist there was a woman's wool-clad arms caressing and exciting a vigorous erection. Her arms were moving rhythmically up and down my shaft, and she spoke purposefully.

"Well, I think you are taking this quite well young lady, but I'd like you to cum for me soon. And I'd like you to cum in my hand please - no mess on the carpet and certainly no mess on my nice clothes! Let me know when it's ready."

I looked down, to see her dark blue wool-covered arms reaching to my groin, her left hand now holding more loosely around the end of my cock, her right hand pumping strongly - and me in a white cardigan, hands behind my head, with well-filled boobs squirming, and mauve skirt around my knees. I began to pant as she kept up her motion, my mind swimming with ecstacy and embarrassment as this middle-aged woman gave me a hand job. And she was an expert with her fingers, squeezing and moving up and down in pure heaven.

"I can't stop now, I can feel it coming..." I panted.

"Good," she replied, "That's what I've been waiting for - now just make sure you spurt it all into my hand. That's right, come on!" she urged, her left hand getting slippery from my first juices as she kept up her pumping of my cock.

Then as she continued her insistent "Come on now." encouragements, I came. I spurted into her hand, letting out a moan of pleasure, then as she kept pumping me a splash of cum went right up her sleeve, wetting her cardigan.

"Oh, naughty!" she chided, "Now let's get it all out of you - till the last drop!" and her hand kept pumping me faster until she could feel no more coming out of me.

The feeling was just so gorgeous as she squeezed out the last drops of my cum. And the image of her hands on my cock was fixed in my mind as my coming subsided, and her hand-movements slowed. She smiled, and looked up at me:

"Now you can have a flat tummy in your skirt, can't you?" she said, pulling her cum-filled hand towards her.

"So what she will do with your excesses, then Andy? Would you like to lick them up for me?"

I was horrified at the thought, but could tell I had no choice as she raised her hand up towards my face.

"It's no good making a mess if you don't clear it up, my boy," she sounded like a school teacher now. "So just put out your tongue and lick it up for me, come on!"

I caught a glimpse or myself in the mirror as I lowered my head to hear hand, and put out my tongue as she'd ordered. Then suddenly she just pushed her hand into my face, forcing my head backwards so that all my cum slipped into my mouth, warm and salty and sticky.

"Mmmm!" she smiled, "Now swallow it all down, there's a pet... Good boy! Now just lick my hand clean for me!"

So I ended my humiliation my licking the palm of her hand, my naked cock now shrunken.

"Well there's no mess on the carpet, so that's a job well done." she smiled. "I'm just going back to open the shop, so I suggest you pull the curtain and get changed again. I'll sort out the price of your new clothes once you've got them off and brought them out to me."

And with that she left.

I slowly came down to earth, as my breathing came back to normal. I stripped off the skirt, and pulled my pants back up, helping my cock into a comfortable position. Unbuttoning the cardigan it seemed like it had all been a dream, but I knew it was true enough. Soon I'd undone the bra and left it on the chair, and was getting dressed as a man again. Checking I looked OK, I picked up the cardigan, skirt, bra and tights and took them all out towards the counter - glancing first to make sure the shop was still empty.

Maude was at the counter, looking business like and amazingly ordinary, considering what she'd just done.

"Now," she said, "You've decided to take these, have you sir? Do you need all these tights too?"

"Er, no." I replied.

"Well do you have any other padding you can use to get your bosom into shape?"

"Well, no I suppose not."

"Well in that case, sir, I'll have to charge you for these - let me see - seven pairs of tights and four stockings. So alltogether..." she rang the numbers into the till, "... That's one cardigan at £8, one skirt at £5, one bra at £3 and say another £3 for the tights and stockings." she rang up the total, "That's £19 for the clothes, and let's say another £10 for the donation."

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