Punishment and Errand

by Jan Poppy

  The story so far. Auntie Cassandra had trained me as a maid doing all the tasks of looking after a house. At the start of summer she had replaced all my clothes with a wardrobe of pastel rompers, dungarees and very short shorts. With the help of her sister Susannah she was taking my sissification to the next level.

I was propelled into the bathroom and ordered to strip off so I could shower and smell 'all sweet' before I was allowed to put on my new clothes. I stood there naked, hands covering my tiny clittie whilst my aunts inspected me. Auntie Susannah stepped forward and ran a fingernail down my chest and then lower, swatting my hands away from covering my sissy bits, making me shiver with delight at her touch but embarrassment at her penetrating gaze.

"My, My! Naughty girl you've wet your panties, what a baby you are. Cassandra, your herbal girling treatment is working wonders, he's completely hairless and his skin is so soft."
She ran her hands down my sides, pinching my bottom, "and starting to develop some really nice hips and botty cheeks too!" Her hands rose to my chest, squeezing my nipples, making me gasp with surprise at the pleasurable feeling. "Look at tiny little clittie and cherries, they're so small!" She burst out laughing. Her hands stroked my small breasts and enlarged nipples. I cringed at her insults and flushed bright red.

"Go and fetch the hairbrush and a towel," she ordered, "kneel down here and beg for the spanking you deserve." I jumped to obey her command. She sat down on a stool, spreading the towel over her long pleated skirt. "Settle yourself across my knees! Count every spank and thank me for each one! Little sissies like you must learn to obey their betters instantly."

With one hand she held my wrists together up my back. The first swat on my cheeks caught me by surprise making me yell out. The stinging sensation spread out across my buttocks but worse still the rubbing of the towel made me so stiff and I moaned with a mixture of delight and pain. Each blow and jerk of my body increased the pressure to spurt and I cried with pleasure. "Eight, nine, ten, eleven, twelve, thank you Auntie Thuthannah," I chanted. Then, it happened, wriggling desperately, I felt my warm sticky cum shoot into the towel.

"Well, well. Just as I thought, you're a pathetic little specimen. Admit it, you are just so excited at being dressed in such a sissy frilly dress and being spanked in it. Come on, say it out aloud. You should be ashamed of yourself."

Auntie Cassandra dragged her fingernails up the inside of my thighs and across my sore hot cheek, repeating the scratching again and again making me squirm and groan again in agony and delight. She separated my cheeks with her cool palms opening up my rosebud
to view whilst circling it with her long nails. "That sensation excites you doesn't it? I'll get you a present, perhaps a vibrating dildo, no, a large inflatable plug so we can stretch you nice and wide. Then when you wiggle your hips whilst wearing it you'll get such delicious feelings inside you, you won't want to stop. Oh! And a chastity lock too for that effeminate tiny lollipop." One last spank with her hand and she lifted me back to my feet.

Through gasping sobs I begged to please them, "Pweathe dweth me in the thithietht dweth, petticoat and bonnet you have." Auntie replied, "the pink dress with 'Sissy' emblazoned across it will be ideal for you as a working maid. Then you can spend all day in it doing your chores. Every time you see yourself in the mirror, answer the door or go out on an errand your dress will shout 'Sissy' to everyone who sees you. Go and get showered with that lovely scented gel and come into the dressing room so we can make you into the beautiful little sissy that you deserve to be. Then go downstairs to show everyone your rosy red bottom and we can take photos for the Ladies' Guild Sissy Page.

I cleared away the plates and cutlery after Auntie Cassandra's and Auntie Susannah's lunch, seeing my shaming pink sissy attire in the hall mirror, I set about the washing up. What a terrible pathetic sight I must be, I was so shocked to be dressed in such a girly way. I felt quite tired out by the morning's events and everything seemed to be totally out of my control. As soon as I finished my auntie had ordered me to reappear for a second spanking from both of them and so they could judge how well I performed curtseys.

"Hold your dress four inches in from the hem with your thumb and first finger and delicately point out your other pinkies. Left heel turned out and then place your right foot behind it in line turning it out too to form a tidy V shape. Now gently lower yourself with your back held straight and your eyes lowered in a truly subservient manner," auntie ordered. "That's just not good enough, you need to be punished for all this complaining. You are now a sexless feminine wimp who obviously enjoys wearing little girly sissy dresses. Don't you? Go and kneel in the corner facing the wall until we're satisfied you've learned your lesson".

"You know it's not all bad things that are happening to you. We are training you to have a truly feminine deportment and mannerisms so you won't stand out as being awkward and masculine," stated Auntie Susannah. "We have many friends who have successfully trained their charges as sissy maids or 'lickle baby girlies' and they can introduce you to the delights of sissyhood. You'll find you can't imagine living any other way. Come sit by me and rest." She had undone the top two buttons on her blouse and I caught a full sight of her beautiful swelling breasts. I sat down and she pulled me to her so my head rested against their softness whilst I drank in her musky perfume. "Now I know your dummy calms you down so snuggle in to me and imagine my nipple is your comfiter." She lifted her breast to my lips, tipping up my chin so I could latch on to her. I was just overwhelmed with pleasure at this honour. As I sucked and sucked on her nipple she gave out a soft sigh, her hands caressing my hair and I drifted away.

I came to, curled up on
the sofa. "Wake up sleepy head and go and freshen up, we're going on a little errand." I ran upstairs to freshen up my make-up and straighten my dress. The aunties appeared holding a sissy handbag and extra petticoat for me, just to complete my outfit!

I hesitated on the doorstep. Auntie took me firmly by the elbow and guided me to the backseat of her car. "Just a little trip to give you a breath of fresh air and convince you that you can go out," Auntie Susannah chortled, looking very pleased with herself. I feared what they had in store for me. A few streets away they pulled up by a postbox. "Just post this letter for us." I opened the door a crack, looking furtively around. "Come on hurry up, we haven't got all day," Auntie Susannah said crossly, getting out of the car and helping me out. "Look there's hardly anyone around and I want some photos of you in your sissiest pose, head tilted, wrists bent down, knees tucked in. Make sure I can see your face clearly" She clicked away, cars passed, someone tooted their horn, I was petrified. Whilst I was posting the letter auntie climbed back in and with a gentle wave called, "it's only a short walk home, enjoy!"

"There! That wasn't so bad. The World didn't open up and swallow you. So what if a few people laughed, pointed and stared. They'll get used to seeing you out and about", auntie said.

"Disobedience and complaining. It just won't do," Auntie Susannah retorted, "we need to enrol him in The Ladies' Guild Nursery. We'll ask Dominique Nurse if there are any vacancies. He needs to be taken back full babyhood with every decision made for him and having no control over his life just like when he was tiny. Feeding bottles, nappies, baby clothes and a new sissy hairstyle for him. He needs to learn to do everything he's told without hesitation or question and only speak when he's spoken to. No more male names, it's Poppy, she and hers from now on."