Auntie knows

Story Info
Who is Auntie and why does she dress you as her maid?
2.5k words
4.14
211.2k
50
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Tomsparty
Tomsparty
645 Followers

You are in a converted loft as a shiver ran through your skinny, hairless body. You survey the pretty maids outfit lying majestically on the guest bed. Made of a sensible black polyester with short, puffed sleeves trimmed with white lace, dainty yoke neck, tailored Basque type top, nipped waist with a bottom skimming short lacy skirt. Your pulse quickens as you finger the masses of stiff underskirts, knowing so well how they will make your skirt stick horizontally like a ballerinas tutu.

You loved staying the weekend at Aunties. She wasn't your real auntie but neither of you cared. This was unimportant. She understood your need. She enjoyed your help as much as you enjoyed helping. The pretty maids dress beckoned you closer. It called your name. Wear me, wear me the voices rang inside your head. The skylight open, the skirts fluttered gently in the morning breeze as if gesticulating towards you. Your tormented body awaits its fix you yearn to stretch it over your quivering body. Auntie is so kind. She's bought you new shoes since your last visit. You complained that they where too tight. But these had a different challenge. They where nearly 8cm high and the heel narrowed like a stiletto. A tiny bead of sweat runs down your back and your breathing becomes heavy and loud in the confined space. It was all too much! Your cock spasms and your balls feel heavy and full. You want to jerk yourself off but know Auntie expressly forbids wanking - but how you enjoyed Aunties comforting rough hands teasing you.

You're now undressed. She always insists you get out of your beastly (her words not yours) masculine clothes the moment you arrive. She can barely look at you in trousers. Excitement mounts as you smell floral perfume in the room. Your cock stiffens and you can't resist holding it lightly. As if in sympathy it seeps some precum onto your sweaty palm.

'Oh dearie-dearie me!' said Auntie, bustling into the bedroom, her heels clacking on the bare wooden floor. 'Can I never get a moments peace and quite?'

She hurries across the floor to you, unfolding a pretty pair of lace panties as she goes. A silky swish filling the room.

'Now, feed your legs in for Auntie,' she says calmly, 'and lets get you dressed pretty. We both have work to do. I have lots to write, deadlines to meet and I find you such a creative inspiration.'

You love Auntie, trust her implicitly, smile and step cautiously into the waist of the open panties. You squirm as girlish memories come flooding back and the materials coolness makes the tiny hairs on the back of your neck prickle expectantly. Oh! How you enjoyed being dressed by Auntie.

Like a well rehearsed actor in a play you know precisely what to do. Arms glide into the padded bra, turn as she clips you in. Stand stock still as she drops a delicate chemise over your head. Step one foot at a time into the maids dress and wiggle your hips as she pulls it over your tiny frame and slips your arms into the sleeves. You gasp as she hooks the eye into place. There's no turning back, the dye is cast. The sheer beauty and enormity of what you're doing takes hold as you slowly lose all elements of masculinity and become her submissive sissy.

A special surprise - Your delighted to be wearing stockings and suspenders rather than tights and the sexy sparkle in your eyes pleases Auntie as you step into the many netted underskirt. As predicted, as she pulls it high round your waist the maids skirt sticks out proudly and every slight moment sends your skirts swishing backwards and forwards like a heavy church bell. You bend demurely at the waist to slip your stocking feet into your new heels and revel in the wild sensual sensation as the bell tolls and your skirts chime sending the hems skywards exposing your fleshy thighs and pretty panties which now contain a cock so rampant it strains against the constraints of the flimsy silk.

'Sit for Auntie,' she says patting the bed, 'and lets fix your lovely hair and pretty face. Moments later she's stretched a long blond wig on your head, tied it up with pins and clips and topped it with a stiff white maids cap. Blondes do have more fun as being blonde makes you feel sunnier and sexier than ever before. Make-up followed. Brows are arched, lashes accentuated, eyelids highlighted, cheeks powdered and lips coated with a luscious pink lipstick. Auntie is proud of her work and soon you look amazing. A beautiful, sexy maid ready to serve. With long slender legs that seem to reach for the sky, heels that renovate your ankles and a dress that has transformed your figure into a perfect, sexy hourglass. You feel so young and slim and so feminine you want to cry. But Auntie has a surprise as instead of getting up and directing you to your duties she lifts your skirts and tugs your panties down slightly with one hand, dipping the other into a blue jar of homemade lubricant. A pungent whiff of eye-watering fish fills the air.

'Aunties missed having a pretty sissy to help her round the house,' she sings as her rough fingers work the embrocation into your pallid ball sack and rigid cock. You immediately feel the magic of her medicine and instead of ejaculating in her hand as you would expect you feel your tortured cock being soothed. The spasms cease. Your cock wilts and becomes flaccid, shrinking back inside as if never there. You sit back on the bed as Auntie rearranged your uniform.

'That'll do you for now,' Auntie announced, pulling your skirts down and straightening the seams of your stockings. 'Now don't go getting yourself all excited again,' she chided you. 'You know I don't allow it. When in my house you're a pretty young maid during the day and a angelic young lady in the evening. Young girls do not have big cocks ruining the line of their dresses and they certainly do not have manly thoughts.'

You stand upright your legs slightly crossed, your hands bent limply at the elbow so as not to restrict your skirts billowing underskirts.

'How do you feel now that you're back?'

It's a familiar question but you always struggle with your reply. It takes a few enjoyable hours to fully enter into the girly sprit. But Auntie is impatient. 'Very feminine,' you mutter. 'The dress is flattering. My make-up impeccable and I feel incredibly submissive.'

'That's good my dear,' she says kindly, 'for its now time to work.'

'Tea,' you murmur, your eyes fluttering for a moment. 'I'd like some nice herb tea. I'm parched'

'Good idea,' said Auntie turning to leave. 'A little insolent – please don't forget your place. Aunties a bit busy at the moment. Besides dressed as my maid, tea making is your responsibility. ' You nod resignedly and shuffle towards the kitchen your skirts swishing loudly.

Downstairs you dutifully boil the kettle and arrange the cups and saucers on a tray. You glance out the window at the back garden relieved that the Aunties house is not heavily over looked. You catch your reflection in the window and marvel how young and elegant you look. Auntie has done a superb job. Had anyone see you mince about in the kitchen you doubt they would see through your disguise.

'Where's my tea,' Auntie calls impatiently.

'Coming Madam,' you cry knowing how Auntie is a stickler for the old fashioned form of address. Quickly grabbing the tray you totter in your heels into the study.

Auntie is hard at work. She barely looks up. 'Thank you sissy,' she says. You curtsey but she appears not to notice. Then all of a sudden as you wait to be dismissed. 'No biscuits!' she snaps, 'I don't take tea without biscuits. You stupid girl how many times?'

'S... S... Sorry,' you say apologetically and spin on your heels to return to the kitchen.

'Not so fast, sissy,' misdemeanors can't go uncorrected or you'll never learn.'

'I said I'm sorry,' you say. But this wasn't the required response.

'Don't talk back girl' she barks pushing her chair away from her desk letting it glide back on the castors. She eyes you angrily. 'Lift up your skirts and show me your pretty white panties.' Nervously you stoop and gather your skirt and the mass of stiff underskirts in both hands, Your beautifully painted nails highlighted wonderfully against the white skirts. You tremble as you raise them slowly exposing your legs, then your stocking tops, lily white flesh and finally your silky panties.

Auntie smiles cruelly relishing your humiliation. 'And how does your uniform feel my sweet?'

'O... O...OK,' you stutter.

'Only OK' she shouts sternly. 'That beautiful, black starched uniform, those frilly petticoats, soft panties and silky stockings. Is that the best you can do?'

You tremble slightly and hike your skirts slightly higher. 'It's beautiful,' you gush. 'I'm a very lucky boy.'

'Absolutely you are. Give me a pretty dress and I'll show you how every sissy wants to wear it. Yet you must learn.' She tuts like a schoolteacher and waggles a hooked finger at you as if a naughty child. 'Come towards me and bend over my knee.'

You shuffle forwards and lean over her careful not to crease your skirts or snag the lace on the corner of her desk. Auntie grabs the nape of your neck and drags you over her knee your skirts rustling and your stocking swooshing. She pushes your head down and you pivot on her lap like a seesaw your heels just off the ground. Your long hair unfurls from the plastic cap and flops over your eyes with a shimmer. She picks a twelve-inch ruler from the desk and raises it above her head. 'I take biscuits with tea in the morning and cake with my tea in the afternoon.' The words hardly out her mouth as the first blow smacks across your pantie covered bottom. You bite your pink soft lip as she raises her hand and brings the old fashioned wooden ruler down on to your plumb fleshy behind not once, not twice but three more times. Tears form in your eye but you sniff and try to conceal your discomfort. 'My Sissy's put on some weight since you where here last,' she says gently, her hand resting on your bottom, her fingers probing your crack teasingly. You've been working out as I taught you and you've been taking the special supplements.'

You nod vigorously though you doubt she can see. You've no idea what you've been popping the past few months but you've noticed the dramatic effect on your body. Your skin is softer and clear like a babies. Your waist narrower, your hips wider and you're convinced your legs are longer and your cock smaller.

She pulls you off her knee and you struggle to arrange your mass of hair.

'I will be requiring my evening meal at six precisely. I want salmon and new potatoes with greens... Perhaps a few sprigs of asparagus. Fix yourself something and after you've cleared away the things you may change and join me in the lounge for a game of cribbage.'

A bolt of fear runs through you as you struggle to remember the rules of play. Auntie hates to repeat things twice. You curtsey and are about to leave when...

'Just one thing dearie. I took the usual liberty of locking all your normal clothes in the shed. The ones you bought with you.' She smirks. 'I'm always flabbergasted as to why you bring so much stuff when you quite clearly don't wear any of it. You can have them back after the weekend. If you want to...' she smirks again and her bright blue eyes wander up and down your feminised body hungrily. You've been here before, many times, yet her piercing blue eyes cease to send shivers through your bones.

'And tonight, dearie, I want you to select something suitably pretty from your new sissy wardrobe. I've updated it since you last came with some extra special things for good little girls.' She pauses and grins wickedly, 'and for girls that aren't so good.' She stares at you for a moment to let the words sink in and though your cock is paralyised and incapable of an erection you feel your panties dampen with excitement.

She can tell and smiles. 'Don't look now. Hold your excitement, if you can. I'm sure you can help Auntie by doing my washing, vacuuming, dusting and watering my beloved houseplants and greenhouse. Poor old auntie isn't as active as I used to be. Now run along.'

You turn and mince back downstairs wincing as your spanked bum smarts in the cool panties wafted by the air billowing round your legs with every downward step.

'Oh dearie,' she shouts like a foghorn, don't forget my custard creams for my tea. And don't bother with a plate you can carry them in your panties. And I don't want crumbs up the stairs or my biscuits all broken.'

What pretty new things has auntie bought you in her wardrobe? You can hardly control yourself as you wrap a pretty heart shaped pinafore round your waist and carefully place three biscuits down the front of your panties. Auntie always surprises you with some odd request but you are her maid and you're happy to serve.

Navigating the stairs was predictably difficult but with tiny steps you managed to deliver Aunties treasured biscuits without any breakages. Back in her study you lift your skirts and she dips her fingers into your panties like a kangaroo tending its pouched baby. 'Well done,' she says reaching for her tea. You may leave me now.'

You step back, rearrange your skirts again and curtsey.

Down the hall you carefully pick up the odd biscuit crumb off the carpet before searching for the feather duster in the kitchen.

Minutes later you're waltzing round the house like a seasoned ballerina dusting daintily like a fairy with a sparkly wand. You're elated despite the custard cream crumbs in your panties. Your mind off with the fairies dreaming of the mystery wardrobe contents. Was it a tight skirt and fitted blouse or a shockingly short mini dress?. Stockings or tights. French knickers or thong, panties or briefs! Sandals, sling-backs or towering high heels. Whatever girlish delights it contained you where assured that it would be adorned with ribbon and lace and incredibly feminine. For Auntie had impeccable taste.

What joys did the wardrobe contain? Who saw you skip up the garden path to water Aunties greenhouse. Did she administer any more corrective punishment? Who did auntie invite to join in the game of cribbage that evening and did you ever get to release your tortured cock. You decide!

The end.... Maybe

Tomsparty
Tomsparty
645 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
6 Comments
AnonymousAnonymousover 1 year ago

I have several aunts, on my mom's side, as they be my mom's sisters. One is a school teacher in an all girl's school. Another a seamstress and the other a nurse. I have spent a holiday at each of their houses in a summer, and thanks to my mom, mom told them all about my desire too dress as a girl. Aunt Hilda the school teacher would have me in a schoolgirl uniform and spank me over her lap, with my gymslip up and my schoolgirl regulation knickers down. My aunt Beryl many a time had me dressed in a dress she was making for a girl, to finish off the hem. Aunt Joan loved playing hospitals with me, having me dressed in a nightdress and pretending I had to go into the women's ward, as there was no room in the men's ward. Each aunt would shave off my pubic hair when I arrived there at their home. The reason being all said the same, that it would emasculate me. Each aunt had daughters and each daughter knew of my cross dressing. I would have to stand stark naked in the middle of the lounge with my hands behind my head. fingers locked together and feet astride, while all commented on my penis and how it would have been much kinder if I had been born a girl.

AnonymousAnonymousover 7 years ago
2nd person is bad

Couldn't get past first paragraph. 2nd person is extremely difficult to write effectively. More practice is needed.

AnonymousAnonymousabout 11 years ago

i want to read more ,i dream of being a maid full time ,

AnonymousAnonymousabout 15 years ago
Newspaper ad

I placed an ad in the Sydney Daily Telegraph, male likes pantyhose, keen to meet same.Two days, i got a text that interested me,interested same call me, i did David spoke ,said why dont i come to his place as he has other clothes i could try if i wanted.O.K. ,lower North Shore, pulled up outside the house,rang bell, he answered dressed in a short dress and black pantyhose.Went inside, offered me a drink, sat down opposite me,legs a bit apart, so i could see his pantyhose covered cock, i looked, like what you see, i said yes.Well show me ,so i stood up , dropped the jeans, to show him my sheer pantyhose covered legs and arse.Turn around, i did, nice he said and grabbed my hand and took me to his bedroom, opened the wardrobe, pick some clothes and come out.Inside were various dresses and skirts, blouses and 4 wigs.I chose a black maids skirt,very short and flared and a brown wig.I looked in the mirror,not bad, my cock was hard, and i walked out.David looked at me, smiled and said get me a drink,i looked puzzled, well your the maid, get me a drink.I brought it back to him,and as i did he ran his hand up my hosed legs, brushing my balls. I stood as he fondled me, then he pushed a newspaper onto the floor, pick that up, so i bent down to get it, he stood and levelled his hosed cock at my face.He grabbed my head and said lick me, so i licked his hosed cock, my head under his dress.He pulled back, turned, lick my hosed arse, so i did my tongue trying to push into his pantyhosed crack.He turned back around, this time his cock out of the pantyhose, suck it,so i put his cock into my mouth and sucked on it.He grabbed my head, fucking my mouth,come on slut suck me, i did so.Then he pulled out, get on the lounge, so i stood up , not like that as he pushed me over the thick padded arm.He lifted my dress up,then i felt his tongue on my arse, licking at the nyloned crack.Stay like that, as i heard him move away then return.He pulled the back of my pantyhose down, a lubed finger was pushed into my crack and moved in and out and around.Then i felt the head of his cock positioned at my hole, push forward but it did not go in, no i said, i think your too big.My arse was slapped, shutup slut, youll take all ive got, with that he positioned his cock and pushed harder, the head entered me and he held still, pulled a little way out then pushed back in, more went in, he did the same again about 5 more times and the whole length was in me.Sure, it hurt but i was enjoying the scene, then he grabbed my hips and started to fuck me, slowly, then faster, faster until he got into a steady rhythym.I was enjoying it, being fucked like a slut, when he slapped my arse,push back, so i did as he went forward, i pushed back meeting his thrusts. He went very deep into me, my cock now going hard.He kept fucking telling me to cumm into the front of my pantyhose as he fucked me, i was about to anyway, but he went faster and my cock let loose into my pantyhose and kept cumming, cumming, clenching my hole around his hard thrusting cock until with one big thrust he burst into me, fucking me as cumm filled my hole.Still hard he collapsed on top of me, cock still in me, until he pulled out, cumm leaking out of my hole.I stoodup, he asked for my cumm filled pantyhose, so i gave them to him and he licked my cumm out of them.We get together many times,once i was blindfolded and made to service what i found out later was 5 guys.I remember the last guy, he was huge,after the others had filled me he still had difficulty fitting his huge cock into my hole, but when he did, he gave me the best fuck i have ever had, when he came so far up inside me, i blacked out as i orgasmed, and i heard the other guys cheering.I was very sore for a couple of days, but i got his phone number and he fucks me once a week, i pass out nearly every time he cumms in me.A film was taken of him fucking me , it is on the net.I love it.

AnonymousAnonymousover 16 years ago
Sissys love

I love sissy stories. Especially sissymaid stories. I have a pink sissymaids dress and just love wearing it every chance I get. I love it when my wife teases me and hulimates me about being a sissy.

Show More
Share this Story

Similar Stories

Feminized by My Girlfriend The start of how she changed my life.in Transgender & Crossdressers
Feminized By My Mother Ch. 01 Shemale mother makes son a sissy.in Transgender & Crossdressers
Her Presents She had a number of surprises for him.in Fetish
Double Wedding Dress as the bride but your wife's got a surprise.in Transgender & Crossdressers
Turning Him Into A Whore She turns him into a trick turning whore.in Transgender & Crossdressers
More Stories