Chapter 1 here
Pleasure and Pain
(The story so far: maid ruby has been suitably dressed by Mistress and maid vikki. They are left alone and start misbehaving. Mistress catches them at it and declares that they will be punished.)
“Stand over there” says Mistress, and we obey. “Facing each other, not touching, but keeping eye - contact. Stand with your feet eighteen inches apart, with your bottoms stuck out as far as they can go while still standing up straight” Once again we obey and I see the hint of a smile in vikki’s eyes. Mistress walks towards us, Her heels clacking on the hard floor. “Reach round each other – NO touching - and lift up the back of each other’s skirts and petticoats.”
I tremble as vikki slowly lifts the hem of my dress and my seven layers of chiffon pettis. I reciprocate, feeling a wave of desire flood over me. Mistress circles around us, inspecting our panties, or in my case, bloomers. “Approved” She says as she marches across the room to the wall of punishment instruments. We can’t see what She picks, as we are constantly keeping eye-contact.
“I am going to start today with the wooden paddle: the mildest of my many punishments. You will receive twelve spanks each, this time, through your panties, which is very lenient given your gross misconduct.” She circles us again, stroking our bottoms through our panties and bloomers. I notice vikki’s eyes grow dreamy as Mistress circles us with the paddle. I hear a loud “Smack” and see vikki wince. “Thank You Mistress for the first stroke. Please may maid vikki have another?” I hear Mistress walk around us then ‘Smack’ as the paddle lands on my chiffon-clad bottom. The pain kicks in and I sense vikki smiling. “Ouch!” I cry. “So what do you say, apart from ‘Ouch’”. I whisper back “Th-thank you Mistress, for that first stroke – p-please may this sissy have another?”
“Oh yes, sissies, you may both have another – in fact eleven more!” says Mistress in a tone denoting pleasure. ‘Whackkk’ on vikki’s rump. I see vikki flinch again then it’s my turn. ‘Whackkk!’ I start to feel tears well up. Vikki’s eyes are dreamily smiling as I gaze into them. As the punishment continues, the strokes get harder, and I feel tears welling up, but I am determined not to weep and blink back the tears.
“Ruby – keep eye contact or you will receive another twelve.” I concentrate as fully as I can on gazing into vikki’s dreamily smiling eyes, trying not to close my eyes as each painful stroke lands searingly on my buttocks through the thin, loose, pink glass-silk bloomers. By the sixth stroke I am trembling all over – my knees feel weak and it’s all I can do to maintain my position.
To demonstrate her supreme skill and devastating aim, Mistress lands the seventh stroke squarely on top of the first smarting blow. I think my bottom will explode with pain as I squirm but I manage to keep eye contact and hold back the tears. I do, however, cry out. A small scream, but loud enough for them both to hear. I see vikki smile as Mistress orders me to stay silent. The eighth stroke is similarly planted on top of the second, and so it continues. By the tenth, although the pain is exquisitely agonizing, I begin to feel a strange sense of calm, and the urge to cry recedes.
Somehow I survive the twelve – I could feel my bottom burning as I managed to hold back my tears.. “You may rub your bottoms.” I rub through the chiffon, trying to soothe the hot pain. “Ruby – kneel down in front of vikki and pull down her panties – slowly.” I get to my knees, reach up under vikki’s dress and pull her panties down to her ankles – slowly as instructed.
“Now stroke vikki’s sore bare bottom and make it all better.“ I do this feeling the tenderness and beauty of her flaming cheeks. I feel myself getting turned on.
“Get up – now your turn vikki.” She kneels before me and I feel her sweet hands slide up my legs, over my oh-so-sore bottom and hook her fingers into the top of my bloomers. She slides them down to my ankles, and starts to caress my oh-so-sore bottom. I feel myself getting even more turned on, and too my intense shame I have a fully visible erection.
“You won’t be needing THAT!” says Mistress, forcefully. “Unless you really want further chastisement.” I feel my erection subside from sheer terror, as vikki pulls my bloomers back up.
“Stand up now.” I do. “Turn around and face me.” I obey, noticing Mistress’s face flushed with effort – and pleasure. “Now, as vikki will confirm, sissy maid ruby, a maid’s life is not all satin and frills. Tomorrow you will start work, cleaning, washing, cooking and generally keeping this house in an immaculate condition. I am a very demanding Mistress where cleanliness and order are concerned, so woe betide you should your work be sloppy. You will be punished for sloppiness in work and appearance, and this time it won’t be just a light tickle through your panties with the paddle. Do you understand?”
“Yes Mistress,” I say, curtseying rather clumsily. “Sissy understands completely.” If that was just a ‘light tickle’ I dread to think what the next punishment would be like, and I vow to behave myself absolutely in future.
“You will wear traditional maids’ uniforms whilst carrying out your duties and going to the shops. Vikki’s is a black, button through dress, cut four inches below the knee, with white collar and cuffs, worn with a starched white pinafore and matching cap. Yours, ruby, will be in pink, as befits a trainee maid. With these uniforms you will each wear black stockings – the seams of which will be kept absolutely straight at all times - flat black lace-up shoes – which must be kept spotless and shined – and underwear that I deem suitable. In your case, sissy ruby, this will consist of a white long-line bra, a white open-bottomed girdle with six suspender straps, white mylesta directoire knickers and a silky white slip.”
Apart from silky – and lace-trimmed – slips, I had never worn that kind of underwear before, though I have to confess I have always wondered what it would be like. Well, tomorrow I would find out.
“On Wednesdays, after your morning chores, you have the rest of the day off. You can go out, do whatever you wish, and wear whatever you like – as long as it’s feminine, of course. You will be back by 10 p.m., or else.”
“Right, sissies, it’s bed time. You will be sharing a room, but needless to say there will be NO misbehaviour. Remember I have closed circuit cameras in every room, and will be keeping a close eye on you. In addition there is a further precaution I am going to take.”
She walked over to the chest of drawers, and took out two stainless-steel chastity cages. I had never seen one before – let alone worn one – and was filled with trepidation. Would I be able to pee? Would it hurt? Would I be released from it in the morning?
“Now these, my little sissies are state-of-the art, tamper proof chastity devices. Your pathetic penises go in the cage, and an opening ring passes under your wimpy testicles. The cage is then locked with a small – but very secure – stainless steel padlock. The cage has an opening at the end so you will be able to urinate, but you will certainly be unable to masturbate and in any case, any attempt at erection will be very painful. So keep your demeanour pure and chaste. Vikki – come here and take your panties down.”
Vikki obeys, and Mistress slides vikki’s sissy penis into the cage, fastens the ring around the back of her scrotum and locks it in place. Vikki pulls her knickers up and then it is my turn. I approach Mistress Zara and drop my bloomers. She slips the cage on – the steel feels cold – and locks it firmly in place. She then unlocks our dresses and shoes.
“Now, off to bed the pair of you. Vikki will show you where the bathroom is and provide you with a toothbrush and toiletries.”
I follow vikki up the stone stairs of the dungeon, and through the sturdy oak door. We walk up two more flights of stairs, and vikki opens the door to our room. Two narrow beds with pink covers and pillows await. I turn back my cover, and there, lying on the bed is an exquisite pink baby doll nightie set. I quickly divest myself of all my clothing, hanging up my beautiful dress in the cupboard, arranging my shoes neatly below and putting my undies in the laundry basket. Shivering, I slip on the panties. They are layered and lacy, the inner layer being satiny nylon and the outer chiffon. The top, which reaches just down to the crotch of the panties is similarly layered. Under the bed is a pair of pink fluffy slippers which I put on, and vikki hands me a pink satin robe that was hanging on the back of the door. I slip my arms in and tie the sash in bow, before going down the narrow corridor to the bathroom. Sadly I remove my gorgeous makeup, have a pee – which I do sitting down – wash my hands and face and clean my teeth. When I return to our room, vikki is wearing a black baby doll like mine and takes a black satin robe from the door before she disappears for her turn in the bathroom.
When vikki returns I am in bed, lying on my side. I can’t lie on my front because the chastity cage becomes too uncomfortable, and lying face-up is obviously out of the question. Vikki sheds her gown – she looks so beautiful. She blows me a chaste kiss, and I blow her one back. I turn out my bedside light and immediately fall into a deep, exhausted sleep.
© sissymaidruby 2020