A Sissy Ensnared

by Sissy Billie

   

"These are rather nice, don't you think cherub?" Auntie asked, rather too loudly. We were in a rather exclusive lingerie store and she was holding out a pair of the sweetest french knickers in pale blue chiffon delicately covered in elegant embroidery and lace.

I felt my face turn a deeper shade of pink, but despite the excruciating embarrassment of the situation I was having the time of my life! I still couldn't quite believe it but somehow my beloved aunt and I were visiting one lingerie shop after another with the sole purpose of buying a collection of beautiful ladies panties – for me! I was already carrying four dainty carriers, all emblazoned with the names of the most luxurious lingerie shops in town. Inside the bags were tissue-wrapped treasures of satin, ribbon and lace

My heart beganto pound again as I remembered the traumatic events of this morning: my aunt confronting me with the overflowing box of underwear she had discovered on top of my wardrobe when she had been searching for a piece of misplaced luggage, her anger - justifiable anger - when she recognized some of her favourite items of lingerie that she thought had been 'lost', her eyes blazing with fury as she cursed me for betraying her trust and hospitality. And my feelings of utter dread and depression as I stammered out one feeble apology after another.

Eventually Auntie grabbed the box and stormed out of the room. I sat on my bed, staring blankly ahead, and once again cursing the irresistible fascination I always had for ladies underwear. I imagined the bleak future ahead of me if Auntie told my shameful secret to other family members. But the most appalling prospect was of being estranged from Auntie, who I had secretly admired and worshipped from childhood. Tears welled up in my eyes and then rolled down my cheeks and I did not try to stifle them.

A few minutes later Auntie called up the stairs. "Come down here at once!"

"This is it" I thought, visualising a scene in which my aunt escorted me to the door and threw my luggage into the street.

I was shaking uncontrollably as I entered the drawing room, my face still hot and red with the tears still drying on my cheeks. My aunt was sitting in her favourite chair – a high wing-backed chair in the bay window. With the sun streaming in behind her illuminating her beautiful golden hair I found it difficult to see her expression.

She pointed to the sofa, where the evidence of my crime – the open box of panties – had pride of place.

"Sit over there" she said curtly and I obeyed as quickly as I could. The two of us then sat in silence for what seemed like an age.

When Auntie spoke again her voice was surprisingly soft. She sighed.

"Well what are we to do with you, you strange boy?" Your aunt is extremely hurt and angry. Do you understand? There really is no excuse for stealing, is there?"

"No Auntie" I managed to mumble, not daring to meet her eyes.

"So you agree with me that some sort of punishment is in order?"

My heart leapt. Punishment? My mind raced. I would endure any punishment if it meant I could stay with my wonderful Auntie.

"Yes Auntie I think so" I replied cautiously.

"Good. Perhaps we're getting somewhere. Now you can tell me honestly what all this is about – why you like ladies panties so much. If you give me a good answer I might - just might - be able to forgive you. If I don't like your answer or I think you're not telling me the truth you can pack your bags and go. So think very carefully before you answer young man. What is it about the contents of that box that makes it worth stealing from me?

My heart continued to race. I knew that so much depended on what I said next. I took a deep breath and began.

"I-I like lots of things about them Auntie." I said. Instinctively I reached into the box with trembling hands and brought out pair of black lace panties. "These for instance" I said, holding them reverentially by the waistband. "They're made from such delicate wispy materials. They are almost not there – like they belong to another world. And I love all the frills and bows and ribbons because they are there just to look – no other reason. Boys' clothes are always so functional and durable – these panties are the complete opposite. They've been made to be beautiful objects like works of art. And they've been made to make the ladies who wear them feel beautiful too. So they've got a special power and I can feel that power…" Here I trailed off as I realised I was absent-mindedly stroking the panties against my cheek as I spoke.

"Well, well, well. I didn't relise you could be so poetic I must say. But I've got a feeling there's more to it than that. Is there anything else you want to tell me about your magical panties? Be honest now."

I took another deep breath. "You're right Auntie. I was just embarrassed to tell you…

I like the way they feel – when I put them on!" I blurted.

"I thought as much" Auntie said smiling grimly. "And what do you do when you've put on a pair of my panties. Come along - tell Auntie everything"

"Oh Auntie please don't make me …" I pleaded, but she continued to stare at me implacably. "Very well" I sighed, then swallowing deeply I confessed everything. "When I put the panties on it's like I've gone into a different world. I get very excited looking at myself in the mirror wearing such wonderful things and I – I touch myself"

"So now we're getting there. You're telling me you prance about in your room admiring yourself in my panties and then you wank yourself silly. Is that right?"

"I suppose so" I admitted.

"I see" said Auntie, "Well I've had enough dealings with the male sex to know they can develop some very strange ideas when it comes to sex. Believe me, I could tell you some stories! But your love of ladies panties is sort of understandable I suppose. As you must know from rummaging about in my room I love beautiful lingerie too – so that's something we've got in common. But I will NOT have you sneaking round the house and stealing from me! You say you agree you deserve some sort of punishment for that and I'm glad to hear it. But we can talk about that later…"

Auntie was silent again for a while. Then she spoke, calmly and deliberately. I hung on her every word; she had obviously made a decision

"You know I've always had a soft spot for you poppet– that's why I offered you the chance to stay with me while you did your college course. So – what I'm thinking is that if you really do love panties as much as you say the best thing Auntie can do for you is –" she paused dramatically to take you on a shopping trip and buy you some panties of your own! What do you say to that?"

My jaw dropped. I couldn't believe my ears! From thinking my world was coming to an end a few moments ago to hearing my aunt's wonderful proposal was too much to take in.

"Yes. Oh yes please Auntie. Yes yes yes! I would really love that. I mean if you're sure. Thank you Auntie, thank you so much. You're incredible you really are! I think that's the most wonderful thing anyone has ever said to me! I'm so grateful…"

"Calm down sweetie! Now come here and give Auntie a hug. Let's be friends again."

I obediently got to my shaky feet and went over to my aunt and gave her a heartfelt squeeze. Tears, this time of joy, ran down my face. I whispered hoarsely in auntie's ear, "Thank you Auntie. You'll never regret this I promise"

"Steady young man - all we're going to do is a little shopping expedition. Now go upstairs and wash your face and brush your hair. Then change into your smart suit and put a tie on. If you're coming out with me I want you to look your best. I think I'll change into something a little more dressy too. Now off you go!"

 

* * *

"Darling, do you want these french knickers or not?"

My attention came back to the present with a jolt. Auntie was still holding the beautiful panties, waving them on their padded hanger a few inches from my face. I looked around and noticed that three or four of the other customers and the two sales assistants were taking a close interest in the proceedings.

My face coloured again. "Yes please Auntie" I whispered.

"Are you sure?" Auntie said loudly. "You haven't looked at them properly yet. Feel that gorgeous lace frill round the leg". She dropped the panties into my tentatively extended hands. "Aren't they just heavenly?"

As always I felt the electric tingle through my fingertips as I touched the exquisite gossamer lace. "Oh Auntie, they are really lovely!" I cried, momentarily forgetting the audience of amused ladies.

"So they should be at that price my dear. But don't you worry about that. This is Auntie's treat!" she said, extracting her credit card from her purse and shepherding me over to the cash till where the two assistants waited.

"Well?" Auntie prompted me, raising her eyebrows. I cleared my throat then said as calmly as I could, "I'll take these please" as I laid the panties on the counter.

"Certainly sir" said the younger of the two assistants, obviously enjoying my discomfort. "These are a medium – is that the size you wanted?"

"I'd say he was a medium wouldn't you?" Auntie said to the older assistant with a conspiratorial smile.

"I'm not sure" the woman replied, narrowing her eyes as assessed me. "If I measured his waist we would know for sure. Would you like me to do that sir?"

I opened my mouth to tell the assistant not to bother when my aunt interrupted. "That's an excellent idea. Come along take your jacket off young man. Don't keep the lady waiting"

I meekly did as I was told and the assistant slipped a tape measure round my waist. I looked round the shop and realised that the other customers had gathered round, no longer even pretending not to be watching.

"Hmm – 28 inches. You've got a very slim waist for a gentleman sir. I'd say a medium would fit you nicely. And I think you're very lucky to have an aunt who is prepared to buy you such lovely panties. These are some of the most expensive items in the shop. I hope you appreciate them and that you'll thank your aunt properly."

The other customers murmured their agreement. I could only nod dumbly and smile as the young assistant, smirking broadly, folded the panties and wrapped the carefully in tissue paper and placed them in yet another carrier bag which prominently displayed the name of the shop – 'Frou-frou'.

Once we were outside I clutched the bags to my chest. "Thank you Auntie. Thank you so much. This is a wonderful thing you're doing for me." I impulsively kissed Auntie on the cheek.

"But we've only just started my angel!" said Auntie looking a little flustered herself. "Our next stop is the department store around the corner - they have a very good lingerie section. Come along now – don't dawdle!"

* * *

When Auntie and I returned home we were both in a state of good humoured excitement. Auntie sent me straight upstairs. "Take your bags into my room and lay out your panties on the bed. I'll join you in a second."

I raced up the stairs and entered my aunt's room. I stepped on to the sumptuous cream carpet and looked around at the extravagantly swagged four-poster bed and the lacy draped curtains. The elaborate dressing table was .covered in mysterious cosmetics and perfume bottles. One wall was taken up entirely by a row of mirror-fronted wardrobes, which reflected the sparkling central chandelier and he feather trimmed bedside lights.

My hands trembled as I put the bags on the white purple bedspread and then emptied out their precious contents. I counted out ten pairs of exquisite panties! All bought for me by my beloved aunt – my heart filled with love and gratitude for her and I felt tears well up in my eyes. I could hear Auntie busying herself downstairs so I amused myself by laying out my panties on the bed in a neat row, picking them up in turn to examine them more closely, and then fussily rearranging them in a pleasing order.

Auntie entered the room carrying two glasses of champagne.

"I think we should celebrate the start of your new collection" she said proffering him a glass.

"The start?" I echoed.

"Why yes. Seeing how much you love panties I've been thinking that if you were a good boy for your Auntie I would buy you some new frillies every now and then - as a reward. What do you think of that idea?"

"Oh Auntie! That is the best reward I could ever imagine. I promise you'll have one perfectly behaved nephew from now on!"

My aunt was silent for a moment, looked coolly at me, then said:

"STRIP!"

"What? Take my clothes off? Now? Oh no Auntie I couldn't!" I gasped.

"So much for your promise" Maybe I should take those" – she nodded at the line of panties on the bed – "back to the shops. I still have all the receipts. After spending all that money on you I would have thought I was entitled to see what you look like in these magical panties of yours." said Auntie moodily.

"No don't take them back, Auntie! Of course I'll show you. I-I was just surprised, that's all" I said, trying to placate her. And with that I began to undress in front of my aunt for the first time. I took off my shirt and trousers, and then sat on the bed to take off my shoes and socks.

With a deep breath I pushed down my shorts and stepped out of them to stand totally naked in front of her as she sat at her dressing table sipping champagne.

She looked at me in an appraising way, her head on one side. "That lady at Frou-frou was right – you do have a small waist for a boy. In fact you've got quite a girlish figure, don't you my poppet?"

I did not answer staring at the floor in embarrassment, both hands struggling to cover my growing erection.

"Come along sweetie. Hands down by your sides – let Auntie have a proper look at you" she ordered. I reluctantly obeyed and my erect penis jutted forward enthusiastically.

"Hmm. A little on the small side for my taste, but I can see that when you say you love ladies panties, you're not exaggerating!"

"I think we need to get him covered up in satin and lace, don't you?"

I nodded my agreement, excitement causing my penis to bob about alarmingly.

"That's not good enough I'm afraid, darling. I want you to choose a pair of panties from your collection and bring them over to me and say 'Please put these panties on me Auntie'. Do you understand?"

"Yes Auntie"

I walked over to the bed and picked up a pair of cute white silk pantied, smothered in rows of lace frills, then put them down again. Next I picked up the pair of black lace panties that had sent me into such raptures that morning. But no - they weren't the right pair for this special occasion. This was such a difficult decision! Finally I settled on a pale pink satin pair with cream lace edging. I held them out in front of me and went over to my aunt who was watching with amusement.

"An excellent choice" said Auntie, suddenly serious. She prised the panties out of my fingers and raised her eyebrows expectantly.

"Oh yes. Please put these panties on me Auntie" I croaked.

She leaned forward and held the waistband open. "Climb in my sweet little sissy boy" she whispered softly. I stepped first one foot then the other into the froth of lace and ribbons and Auntie slowly pulled the panties up my legs. I groaned as thrilling shivers raced all over my body. Then the waistband reached the very solid obstruction of my erect penis.

"My word! We're going to have to stretch these panties a little more to get this little chap tucked away and out of mischief!"

With that she snapped the waistband over my penis and tugged the panties up to my slender waist.

"Now let's take a look at you. Go over to the big mirror, cherub. Show me how you admire yourself when you've got your frilly panties on"

I walked unsteadily over to the wardrobe mirror and looked at my reflection: naked but for the beautiful panties and with a very obvious protuberance at the front. I could feel my penis jiggling deliciously against the cool smooth satin with every movement.

"Oh darling!" Auntie drawled appreciatively. "You look positively scrumptious! Such milky white skin... and such lovely legs! Oh my dear, you're just perfect! Now walk across the room and give me a little turn – and be sure to wiggle that luscious little bottom for me darling! Yes, that's it. That's lovely"

She got up from her chair and came over, standing just behind me. She stroked my hip through its satin covering.

"You look gorgeous" she whispered in my ear. Her hands moved on to tug at the lacy scalloped hem that swished against my thigh, pretending to fuss over arranging the lace just so. I could hear her breathing loudly as she rested her head over my shoulder. Her perfume added to my already overloaded senses. I began to feel that I might faint.I groaned as she smoothed the material over my pantie-clad buttocks.

Then, suddenly, she stepped back.

"This is all very well young man," Auntie said severely. "But there is the small matter of your punishment – for stealing. Had you forgotten our little talk this morning?"

I always found Auntie's changes in mood disorientating - one minute soft and intimate, the next harsh and cruel. Suddenly I felt totally vulnerable, standing in front of this fearsome lady, naked except for the wispy confection that covered my straining erection.

"I suggest I put you over my knee right now and give you – oh let's say ten hard spanks. Then we'll say no more about it - on the understanding that you NEVER do anything like that again. Do you agree?"

I didn't know what to say. My life had been turned upside down in the course of a single day. Now nothing seemed strange or outlandish to my bewildered mind.

"Yes Auntie, that seems fair" I managed to say.

"Good! Now tear yourself away from that mirror you vain creature and come over to the bed." Auntie sat on the edge of the bed, arranging her pleated crepe silk skirt over her lap.

"Over you go!" She indicated with one imperious finger.

I stood by her side and carefully lowered myself over her thighs, so that my feet stayed on the floor and my face was squashed into the satin bedspread.

And so began the first of what was to be many, many spankings for me, stretched over my aunt's knee. This first was relatively mild and short and Auntie used only her bare hand – her hairbrush was to be introduced very soon - but I did not know this as I wriggled about, my penis inside the satin panties pressed against Auntie's generous thighs.

"Hold still you wicked boy!" Auntie shouted at me. Then the spanking began with blow after blow raining down on my pantied bottom. I pushed my face deeper into the bedspread as I squealed and yelped at each blow.

By the time the ten spanks had been administered Auntie and I were both breathing heavily. She pushed me off her lap and I collapsed in a heap at her feet...

After a moment or two Auntie spoke again. "Now my darling I want you to pick up all your pretty panties and follow me." She said. And without waiting to see whether I would obey she swept out of the room. My head was spinning but eventually I registered Auntie's command and jumped up and raced over to the bed, unceremoniously scooping up the other panties in one frothy armful. I ran to the door just in time to see Auntie disappearing into my own room. I rushed down the corridor. Auntie went over to the chest of drawers, stopping only to pick up the waste paper basket by my desk.

"Right!" she said briskly as she pulled open the top drawer where I kept my shorts. "This lot can go straight in here", she said disdainfully, scooping up my underwear and dumping it into the bin. "You won't be needing these again, will you?"

Being rather slow at the best of times I didn't immediately understand what she meant.

"Why do you say that Auntie? I asked.

"Listen sweetie, you now have a fabulous collection of your very own frilly panties, courtesy of your kind Auntie. I paid a great deal for those frillies, not that I regret it for a second – not at all. But I expect you to wear them EVERY day from now on. Do you understand? Underneath your scratchy boy clothes you'll be wearing little lacy panties - and no-one will know except you and me. It'll be our little secret, won't it?"

I gulped, worried at the speed at which my life was being taken over by my domineering aunt, but also wildly excited at each new command.

"Now bring your treasures over here and put them away. There should be enough room in this drawer for now."

So still naked apart from my lacy panties, and with my bottom still tingling from my recent spanking, it felt the most natural thing n the world to put the beautiful lingerie - my beautiful lingerie - into the drawer.

"Arrange them nicely, you untidy creature" Auntie ordered, so I meekly spent a few minutes folding each pair and placing them neatly in the drawer.

"And while we're on the subject of tidiness" she said, gazing round the room at the piles of clothes, books and CD's that took up most of the floor space, "I expect to see a big improvement in the state of your room. And I expect you to be much, much more helpful around the house from now on. I'm going to start to give you a list of housework to do every day, and every day I will inspect your work. If it's not up to standard then you'll be in for another spanking, but if you've done a good job you'll be in line for some more lovely new frillies at the end of the week. Does that sound like a good idea to you?"

When I nodded my assent I did not appreciate that I was taking the first step in my transformation into what I have become today – Auntie's full-time sissy maid, totally devoted to serving her in every way imaginable. At some point during the day my shrewd aunt had realised that by playing on my weakness for frilly ladies underwear she could mould me into the perfect servant and plaything for her amusement.

Auntie laughed. "Now get some clothes on – over your lovely panties of course - and come downstairs. We'll make a special supper together and finish off that bottle of champagne while we discuss my plans for you"

"And after supper we could go back up to my room and play some more dress-up games if you like. I've got some stunning nighties I think you should try on – and a rather gorgeous corset which is a bit too tight for me these days, but I think it would fit you just fine. I can't wait to lace you into it. Does that sound like fun to you?"

"I can see we're going to have lots of girlie fun together. Sissy Billie and his naughty Auntie!"

 

The End

  

  

  

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