Christine’s sister goes solo

A wonderful account from Christine M including her sister spending time alone with DAVID and making him very miserable.

Easter 

My sister is truly vicious and heartless in her treatment of David. When they first met, they never ‘clicked’ and my sister is 20-years older than him which didn’t help.

David had been told to take time-off for Easter since I had booked in to learn gliding at the local Aerodrome, which is about ½ an hour from here. I had not shared that my sister was coming over! 

On the Thursday before Good Friday, he came home from work and was curtly told to change into his sissy frock, rather than his maid’s attire. (The sissy frock was from PDQ’s online store.) He looked at me aghast as he abhors wearing this ridiculous attire. I still didn’t let on that she was coming over so, dressed in his humiliating attire, he looked at me in absolute despair, completely mortified, when he saw her car coming up the driveway. It was a look to behold, and he immediately started trembling uncontrollably. My sister loves the added humiliation his frock delivers, so he knew he was in for a rough evening! My sister was staying until the Tuesday, so he was in for a great deal more misery than he realised. 

 As has been requested, I should describe his frock.

When choosing this I wanted something that would be dreadfully humiliating for him and make him feel acutely ridiculous when wearing it. It also needed to be practical, in the sense he would still need to be able to do his chores when dressed as a prissy sissy. 

We love to tease him about how adorably sweet he looks and fuss over the details of his dress. It is beautifully made of soft shiny satin of the palest blue, with a high ruffle collar that is trimmed with lace and has an enormous pink satin bow at the centre. The figure-hugging bodice has a white satin lace sash which is also tied in a large bow at the rear. 

Huge puff-sleeves are elasticated at the hem of the sleeves with wide pleated lace trim. The skirt is full and falls over a bouffant petticoat, flaring it out. It is adorned with large matching pink satin bows all around the skirt, and hemmed in beautiful shiny frilly glass-silk.

An over-sized, pink hair bow is clasped in his hair, and the outfit is completed by white, frilly lace ankle socks, each with a pink bow on the outer side; pink ballet slippers; and matching panties made of soft, shiny satin, with an elasticated waist and leg openings, also trimmed with dainty glass-silk lace and cute dainty pink rose buds. The panties are on full display as the skirt only falls down to just below his buttock line, leaving his long, shaved, thighs exposed too. 

A large pink dummy is also pinned to the bodice with a pink ribbon. The dummy is of course dabbed with a foul product designed to prevent people biting their nails. This he has to suck on when not required to speak. 

  Following Mistress Scarlet’s lead, he also has three ‘dollies’. A pink teddy, Lickel Pwetty Pinky Winky Teddy Weddy Pinkitikins, came first. My sister and I thought of nice long names to be much harder for him to cope with! Then came a rather old and worn rag doll, who he calls My Vewy Vewy Best, Most Favowite Dolly Wolly. And finally, a large plastic dolly that had seen better days with her painted eyes and lips chipped, Bubby Wubby sookie wookie babykins. 

After my sister arrived and the usual ridiculing of David was done, including him introducing his dollies to much merriment, with my sister shaking her head contemptuously, making him feel even more stupid; she sternly turned to him, popped his dummy in his mouth, and with David looking more anxious than ever, told him that she had a surprise for him and I would be leaving him in her care for a little while. The dummy was quavering in his mouth, and he pleaded with wide eyes for me not to leave. I simply laughed contemptuously at him, as I nonchalantly left the room, advising my sister, I would be in the lounge if she needed me. His face continued to beseech me not to leave him alone with my sister, and my last view of him, saw him trembling like a frightened rabbit caught in a spotlight, his eyes opened wide in fear.  

I could tell it was all too much for him to believe. He doesn’t find my sister attractive in any way, and he knew he was in for an evening of wretchedness, as he stood quaking before a very imposing, ‘authority figure’, who he knew held him in heartless contempt. 

Needless to say, my sister was very cold in dealing with him. I watched using the camera in the kitchen, on the big screen through my Apple TV. Leaving him alone was so that it would leave him feeling more fearful and ever so rejected. My sister coldly laid down her rules. “You DO NOT speak unless I ask you a direct question. I don’t want to hear a peep out of you otherwise. You do as your told, without comment or complaint. DO I MAKE MYSELF CLEAR?” He nervily nodded his head.  

“If you don’t understand something, raise your hand and await my permission. If it is anything other than a question seeking clarification of what I have just told you to do, YOU WILL DEEPLY REGRET IT! I have no interest in anything you might want to say and if I want your opinion… I WILL TELL YOU WHAT IT IS! ARE WE VERY CLEAR?” He struggled to nod his agreement, he was so overwhelmed!  

I enjoy hearing him beg and plead so, even though his pleas always fall on deaf ears, this was going to be a new and frightening experience for him! 

She then told him that when she does ask him questions, he had better respond in his most simpering little girl voice, making sure to lisp and giggle as he has been taught and to express his most sissy desires… OR ELSE! Please read Mistress Scarlet’s books for how he has been trained in all his little sissy mannerisms and how he has to play with his dollies. He rightly feels like a total ‘prick’ when he is treated like this, and don’t we remind him of this! My sister is particularly nasty and cutting in her remarks. 

He was then seated in a chair with arm rests, and securely strapped in place, with his legs spread wide apart and his frock pulled out of the way. He was whimpering by now but knew better than to ask what was going on. I don’t think I have ever seen him look more scared, he was so exposed, so trapped, so alone. I wasn’t there and my sister, who he finds so malicious towards him, was in total control. 

Once he was securely strapped in place, a pink hairdressers cape was placed over his dress as my sister grimly advised him, “Now that you’ve grown your lock-down hair longer, and since you love to dress up as a little sissy, I promised Chrissie, I would give you a nice girlie perm with lots of tight curls.” He looked horrified and I could see him flexing against his bonds, in panic, hoping to escape. 

He was really getting panicky when she then picked up and flexed a really nasty looking rattan cane of mine, showing him how bendy and whippy it was, despite being as thick as her little finger. She flexed it so the two ends almost met, before swishing it loudly through the air. She then lightly tapped it along the length of his exposed inner thighs as she ominously warned him that, if he so much as whispered a word of complaint, even under his breath; showed the slightest signs of disobedience; or failed to lisp and show his enthusiasm for being a little sissy; she would be bringing the cane down on his tender inner thighs.  

Smiling wickedly, she noted he would get three strokes on each leg, but if there was a next time, it would be four strokes… then five…” He was petrified and wincing as she kept tapping his inner thighs. There was no doubt he knew she was not making an idle threat, and the pain would be horrendous. I must share the dialogue as it was quite hilarious. 

She took his dummy out of his mouth and coldly asked “Daisy, are you looking forward to getting your hair permed?”. He was too alarmed to reply and was given a stern warning and reminder, with the cane tapped harder on his inner thigh, prompting him to ever so fretfully lisp, “Yeth, pwease, I weally weally want a perm. Thank you (XXXXX).” He even tried to smile as he knew he was required to be enthusiastic in his role, he didn’t want to taste her cane, that was for sure.  

Whilst he looked totally distraught and crushed, I know that deep down he felt she would not give him a real perm. She then started on his hair, mocking his lack of manliness, laughing at his plight, and really scaring him. She started by reassuring him that the perm wouldn’t last for ever, that it would soon wash out… then, seeing his cautious look of relief, she smiled, “… after three to four months!” This left him teary eyed and ever so upset. 

His hair was washed and conditioned and then, ever so slowly, wrapped very tightly around small spiky plastic rollers, as he squirmed uncomfortably, while she dispassionately mocked him. She told him how sissies couldn’t go gliding, but they would be finding lots of fun things for him to do, while she went with me each day to watch. 

“Your whole situation is quite laughable really… Isn’t it?” ….  

Then in a mocking tone, “I remember you used to be ever so brash, going on and on about your ‘daring adventures’.” She used her fingers to mockingly indicate ‘daring adventures’ in inverted commas… Then, as if speaking to a simpleton, “You don’t do anything that might be ‘unsafe’ now do you?” she smirked.  

“You prefer to stay at home and do chores, write lines and play silly games, don’t you?”  

“You really are a silly twit, aren’t you?” 

I might note here, her questions are NOT rhetorical. He has to answer her in full sentences, or else. This piled on the humiliation, while she kept wrapping his hair in rollers. Imagine being asked if you feel like a silly twit and having to advise, ‘Yeth, (XXXXX), I weally feel like a thilly thwit.”  

Sneeringly she noted, “You’re so pathetic! I remember when Christine first told me about going out with you. She said she was shocked that you wanted to be with her, because you were so much younger,… dashing and wealthy… and were used to dating sexy young ladies and lots of sex no doubt.” 

“Well, you can’t wank-off anymore though, can you?” 

“Can you even get an erection, can you?”… 

“I didn’t think so. What a poor excuse for a man you are! Isn’t that right?” 

“No point you having a penis is there?” 

“Couldn’t please a woman with it if you tried, could you?” 

He squirmed in utter humiliation as he responded to each question. He is ever so upset that I have shared all these once ‘ever-so-private’ and intimate details with my sister. Humiliation had never been on my agenda until Mistress Scarlet coaxed me down the path, and now I just love it. This further upsets him, knowing that we have so much fun at his expense! 

“Do you remember what your mates used to say when you first went out with Christine?” 

“You all used to call her ‘old thunder thighs’?

“And didn’t Christine overhear your best mate comment how he couldn’t understand what you saw in her, reckoned she must really put out in bed! Didn’t they? Why else would you go out with her?” 

“But you don’t get anything at all do you? Not even a quick hand-job!” He squirmed going redder and redder as he kept answering her questions. 

“Did you ever tell them you got nothing?” 

“I didn’t think so! Too arrogant to tell them she put you in chastity! And what happened after all that?” He then had to tell her how he was grounded and forbidden to see his old friends. He had to resign from the sports clubs he was in and sell his share in the boat that four of them owned together. 

“They all had a good laugh at that I bet!” she mocked, “considered you were ‘totally under the thumb’. You would have been a right laughing stock at the rugby club wouldn’t you?” 

“Maybe we should track down a few of the sexy young ladies you used to date? Invite them over for a Saturday night dressed like this! They’d totally piss themselves laughing at you, wouldn’t they?” 

“Would you enjoy that?” 

“You could sing nursery rhymes and dance for them. Wouldn’t that be a lot of fun?” 

He was ever so mortified as she kept mercilessly on at him like this. He had to not only take her mockery, he had to respond that he would really like to do this! 

“Which nursery rhyme would you like to sing and dance to?” she continued relentlessly as he fidgeted teary-eyed.  

He was of course now on the verge of tears again, which brought more ridicule and caustic remarks as he advised which nursery rhyme he would like to sing for them! And she wasn’t letting him off the hook any time soon… she went on to make him answer why he picked that one, what he liked most about it, which was his favourite line and why! What other nursery rhymes did he like? 

“I suppose you want to sing one to me now?” 

“Beg me nicely and might let you …” she taunted. 

After he begged and pleaded, she dismissively derided him, “My goodness! You’re supposed to be a grown man, and here you are getting a perm, playing with dollies and begging to sing nursery rhymes!” then more irritably, “go on then, if you really must!” she snapped, “you can sing it if you really want to!” He blushed profusely as he sang his little nursery rhyme for her. As he finished she caustically remarked, “What a total prat you are! What are you?” 

She then switched tack, “Do you remember how you used to argue with me too?” 

“and how you once told Christine you thought I was ‘bossy bitch’?” He squirmed in extra fear as she reminded him of this, and he had to lisp that he did. I could also see he was particularly hurt that I had shared this too with my sister, it seemed it made him feel completely friendless. 

“Well, you are a lot more polite now, aren’t you?” 

“Now don’t worry Daisy, we have lots of fun things for you to do while we are out… you have all your chores… and you can wash my car… and I brought all my ironing over for you. You love ironing don’t you?”  

“And tomorrow… you’ll get to spend the day colouring in with your dollies. Then on Saturday you’ll be spending the day singing and dancing to your favourite nursery rhymes. Sunday is a full day of disciplinary ironing; (Scarlet, I must update you on how I have made this worse than ever for him)… and on Monday, you can play with your dollies again… Doesn’t that all sound like a lot of fun?” 

Finally, his worst fears eventuated when she took out the harsh smelling perming solution and started to liberally apply it to the rollers. This caused him to make the dreadful mistake of whimperingly begging and pleading for her to stop.  

There was an eerie silence broken only by his whining apologies as he saw the stern set of her face and the irritation in her eyes. She put the solution down and picked up the malevolent cane and lined it up along his left thigh, steadying her aim, her arm rose up high and behind her head. The cane swooshed down as promised, and struck down onto his inner thigh. This was instantly followed by an emotional squeal.

He continued to squeal uncontrollably as the pain continued, his body taut against his bonds as he struggled to deal with the agony, his head shaking wildly in desperation. She waited about a minute between strokes, to drag out his misery. No pity was shown, and the cane bit home 5 more times as promised, leaving him a squealing, squirming wreck. 

She then continued as though nothing had happened, waiting until he calmed a little, though still clearly in great discomfort, before noting, “Let’s hope you don’t require a repeat dose Daisy!”  

With everything in place, she connected a hood to her hairdryer, which was then placed over his head. She then left the room to join me, leaving him squirming in fear. 

He was alone for about an hour before she returned to him. A hair net and a silk scarf were then put in place and he was released. He was ever so shaky, his inner thighs were clearly very sore still, and with bruising beginning. He then got to turn down our beds and get ready for bed himself. He didn’t sleep comfortably with a head full of curlers. My sister had wound them very tightly, so as his hair dried, they would have pulled on his scalp. Also the spikes would have made for further discomfort as he tried to sleep on his side to avoid the worst discomfort.  

He was allowed an early night, but told he had to be in my office with his colouring-in book, his egg-timer and his dollies, and to have started colouring-in BEFORE 5:00 am! Readers need to look at Mistress Scarlet’s books to see this procedure, but it is very humiliating for him, and it is all recorded on camera. 

I think this makes it even harder for him, and I love the way modern technology maximises my freedom and his humiliation. He is in the room all by himself, and he never knows if I am watching, if I will play the recording back, or if I will just totally ignore it and never open the file or even open the app!  

Yet he must assume he is always being watched, as the consequences of being caught out are so dire! He must therefore maximise his ‘enthusiasm’ and effort for hours on end; no matter how humiliating it feels, how abandoned and lonely he feels, how stupid he feels, or how tedious and monotonous and exhausting it is. There he is, colouring-in and talking to his dollies, or singing and dancing to nursery rhymes, dressed like a sissy prat, ALL BY HIMSELF! 

I might say he does also suffer the humiliation and cat calls of dancing and singing in front of us too, but once we get bored with him, he is dismissively sent off by himself. Imagine being snappily told, as he was, “You really are a stupid, boring prick prancing around like an idiot singing nursery rhymes! You are so annoying! Piss off out of here. Go sing and dance by yourself in the study where we can’t hear you! GET OUT NOW! We don’t want to be bothered by you! PISS OFF!” But the camera monitors him nonetheless.

It was gone eleven on the Friday morning before he was summoned to have his hair combed out. We had a hilarious time at his expense. His head was a mass of tight curls in which we secured his big hair bow as we mocked him. He was crimson and clearly very miserable indeed. Sadly, for him, he let a few ill-chosen, adult words slip out while expressing his concern with what we had done to him. 

He had to be secured again, in order to receive eight more strokes of the cane, which were again brought down hard, on his now even more tender inner thighs. He was again squealing in agony. Once he had recovered a little of his composure, we simply continued our harangue, quite unconcerned by his very evident distress. He got to spend the afternoon on chores, before being sent to do a few more hours of colouring in, before bed. 

A lovely point of embarrassment occurred when he asked me, in a private moment, about his weekly chastity release draw. I coldly advised him to ask again when my sister was with me the next morning.  

It was so amusing to watch him turn crimson, dressed as he was, and ask, ever so politely, “Pwease Chwistine, may I make my weekly dwaw for a welease?” I smilingly advised, ‘Of course, you may… But since it is most inappropriate for little sissies to cum, we will not be revealing your result, though it will of course be removed from the spreadsheet. So you had better hope it isn’t your last release option of the year.” He was so nervous now, knowing that he only has one release left for the year, and it might be lost without him knowing! Since he had already lost two ‘reveals’, for earning Linnex punishments, this could be his third lost release option, though he doesn’t know if they were. And nor do I! 

David was kept occupied as described above for the whole time my sister was with us. He also got to ‘enjoy’ some disgusting meals that my sister prepared for him. I must share these too but I think I have written more than enough!  

I might share that my sister and I didn’t actually go gliding; I was with David on the Wednesday through to the Saturday, when we spent the entire time in vanilla mode, though he still wore female lingerie and his curls. The Sunday was a catch-up day of chores though, before going back to work on the Monday. I also used heat tongs to straighten his hair before he went back to work.