Chapter XXI: Redress (Part 2, Judgement Day)
Mum and I were so excited when we heard that Sue had recruited Billy. She’s pretty cute, that one, getting him signed up like that right in front of Simon. And what better initiation could he have than a visit to Rebecca Strickland? People who don’t know her think she’s a very straight, virtuous individual, but we know she actually extremely naughty! I’ve been to her house once, and I can vouch for the fact it’s full of interesting things. The boys didn’t get to see half of them – she didn’t even introduce them to her dungeon – but I’m sure she was only saving such pleasures for a later date. Simon takes up the story.
Thursday 4 August. Billy and I cycled over to Miss Strickland’s house in plenty of time. We wouldn’t have dared be late. On the way Billy asked me about our host.
“I don’t really know anything about her, except she’s an expert on horses and riding. I guess she’s about forty. Bits of grey in her hair, very keen blue eyes, would have made a good interrogator, I should think.”
“When you say interrogator, do you mean torturer?” laughed Billy.
“No, I don’t. Except there’s something about her that makes you feel she’s not someone to be messed with. You’ll see.”
“She sounds scary.”
“Not exactly scary. But I admit you do feel there’s some sort of potential threat if you were to defy her. I can’t explain it.”
We found the house just on the far side of the village. A biggish, red-brick Victorian place with bay windows and turrets and a gravelled forecourt just off the road, surrounded by big trees full of cawing crows. There were three cars parked outside, two nondescript ones and a little bright pink Mini.
“I wonder who that belongs to?” said Billy.
“I bet it’s one of her guests,” I said, “it doesn’t look like the sort of thing she’d drive.”
It was a stupid remark to make, but it turned out to be true. I got the impression Miss Strickland liked to be seen as a very mature, upright pillar of the equestrian world.
We parked our bikes next to the front steps and climbed up to the door. I gave two raps with the big polished brass knockers. Miss Strickland answered the door.
“Boys! Lovely to see you. Come in, come in. Yours bikes will be fine down there. Would you mind leaving your shoes by the coat rack? Thank you so much.”
We found ourselves in a dimly-lit corridor. I was beginning to get used to these big country houses, I thought. Miss Strickland led us into the back room, lit by a sparkling chandelier, and furnished with a polished dining table, very luxurious-looking armchairs and sofas, and even a big grand piano. In two of these were seated two young women, with their heads turned towards us, awaiting our entry.
“Ladies, allow me to introduce you to our two Holly End lads. That’s right, isn’t it, Billy? I’m told you’ve been signed up as well.”
“Yes, Miss. I’m going to be working with Simon now.”
“Madam, please. You may call these ladies “Miss”. They are two of my best friends.” The girls stood up, smiling. “This is Carmelita Ashford-Jones,” she said, indicating a pretty girl of nineteen or twenty of medium height with a mass of frizzy ginger hair and a scattering of faint freckles. “She is young but already an accomplished rider. I hope she will come to excel in the dressage ring. And this,” indicating a taller woman a few years older, darker and more muscular, and also more serious-looking, “this is Tamsin Stratford. I’ve known Tamsin since she was a child. In fact, I taught her to ride. She is already a qualified judge and often sits with me on show panels.”
We all shook hands, rather formally, but that was all right with me. I was wary of shows of affection. As far as I was concerned, this was work, though Carmelita gave the impression of being very pleasant and vivacious. Tamsin, in appearance at least, seemed the opposite. I thought it would be a good idea to appear relaxed and nonchalant, to show I was, in my own way, as professional as them.
“Nice to meet you, Miss.” Carmelita smiled brightly.
“And you, Miss Tamsin. Billy and I have been friends for a long time. We…”
She held up her hand. “‘Miss’ is quite sufficient, thank you. Please don’t waste your breath telling us what we already know. We’ve read Mrs Dawson’s report. You’re here for one reason and one only - to serve us. It’s better that you keep that uppermost in your minds.” I reddened slightly and shut up.
Billy asked about the Mini. It was Carmelita’s, as we would have guessed. The girls resumed their seats and Billy and I were offered the sofa, where we sat close together defensively. We had the feeling we were being subject to the closest scrutiny by all three of them. Tamsin, after staring at us for a while, actually leant over and whispered something to Rebecca behind her hand, which I though very rude, and to which Rebecca returned a grim smile.
Tamsin looked to mean business, I thought. She was wearing a loose white blouse tucked into some pretty heavy-duty blue lyra riding pants, and highly-polished rubber riding boots. Carmelita must have been the others’ acolyte. She wore a black leather skirt, red sweater and thigh-boots. She was pretty and vivacious-looking, and kept smiling at us encouragingly, unlike Tamsin who regarded us with an expression suggestive of critical appraisal. Miss Strickland addressed us:
“So, boys, I should explain the rules. We are alone in the house. My son has gone to stay with his friend. My son is fourteen. He’s been a difficult child, but I adopted a similar plan to your aunt, Simon, after I met you at the show, and it’s working wonders.” Billy looked at me, questioningly. “Rubber pants, Billy!” she explained, to his amazement. “So we are quite alone. I no longer have a husband. That’s why I am ‘Miss’ Strickland. The maid has the day off. We have decided to have a rare evening pampering ourselves. I am going to cook, which is a pleasure I rarely have time for these days, and you two are going to look after the service and our comforts. You will be waiting on us during dinner, and once you have loaded the dishwasher you will be expected to serve drinks and provide any entertainment we request. Understood?”
“Yes, Madam,” we chorused.
“Excellent. First things first. We have uniforms for you. Tamsin will take you upstairs to change.”
“Come,” said Tamsin shortly, indicating us to follow. We understood that this evening was to be a much more disciplined affair than Harriet’s party, and we jumped to obey. She led us to a bedroom. Two dresses were laid out on the bed.
“You are pink.” She said to Billy. “Dress and come down quickly, please.” And she left us.
We looked nervously at each other.
“She’s scary!” whispered Billy. “We’d better hurry.”
The two outfits were identical, though mine was turquoise and Billy’s pink. His was slightly smaller. They had clearly been chosen very carefully. Each consisted of a puff-sleeved satin maid’s dress with a very short skirt, all the edges trimmed with white lace, a stiff gauze underskirt, a little lace-trimmed apron, and white gloves. The panties that came with them looked familiar.
“Hey, these are the panties we wore last week, Billy!” I said.
“They are. I guess they’re okay without those horrible sheath things we had to wear before.”
“Yeah, I guess.”
There was also a white satin garter belt and a pair of long white stockings with lacy tops. We had to help each other with those, but eventually we had them on. We also had a little maid’s headdress, in white lace with a central bow matching our dresses. This was fitted on a plastic headband, so it was easy to put on. Our shoes, which were also colour-matched, had about three-inch heels and broad ankle-straps with padlocks. There were no keys but we guessed we were expected to lock them on, so we did. When we were finished, we looked at ourselves in the long mirror on the back of the wardrobe door.
“We look total sissies!” I exclaimed.
“Yeah, I suppose,” responded Billy, thoughtfully, smoothing down his skirt in an attempt to hide his shiny pink panties, “but they do fit well, Sim, and I sort of like the feel of the stockings. They’re so smooth, and the clip things feel nice on my legs.”
“You like it, don’t you?”
“Well, a little bit,” he admitted. “It’s the first grown-up girl’s outfit I’ve ever worn.”
I laughed. “You’re the best. You do look incredibly cute, I must admit. But we’d better get back.
We hobbled to the door and got downstairs with some difficulty, hanging onto the bannister at every step. With trepidation, we presented ourselves to Miss Strickland.
“Beautiful! Beautiful! Aren’t they, ladies?”
Carmelita looked genuinely impressed. “They’re so cute! They’re prettier than your usual maid, Rebecca!”
“Hmm, I think you’re right, Carmelita. Maybe I should keep them. But would you do the honours, please?”
“The honours” turned out to be a complete makeover. Carmelita told us she had trained as a beautician. I watched as Billy was being powdered and painted, and he made no attempt to hide the fact he was enjoying himself. He sat upright and still on the chair, his hands clasped prettily in his lap, unable to stop himself smiling and flashing frequent grateful glances at Carmelita as she worked, shutting his eyes obediently for the eye shadow. In coordination with his outfit, this and his lip gloss were pink. When she was finished, I actually heard him ask her in a whisper whether we were getting a squirt of perfume. She was only too happy to oblige. My thoughts were conflicted. There was an element of faint dismay at his eager readiness to be feminised, but it was overwhelmed by a powerful attraction. To see my friend who, up to recently, had been the archetypal boy, transformed into this beautiful creature, the personification of my desire, made my heart flutter with excitement.
It was my turn next, and I received similar treatment, except difference being the shade of eye shadow and lip gloss, which matched my turquoise dress. After the makeover, we were fitted with colour-coded chokers in soft, padded leather, and matching wrist cuffs. That immediately put me on my guard – not that I could do a thing about it. We were then made to stand side by side while Rebecca fussed with our stockings and garter-belts. When she was satisfied she stood back to admire us.
“Adorable! Those little skirts don’t quite hide their panties, do they? Perfect!”
Tamsin relaxed in her armchair eyeing us with amusement.
“Little sluts!” she murmured. “Just begging to be groped. Aren’t you?”
“N-no, Miss,” stammered Billy. “I like my dress very much, that’s all.”
Tamsin gave a scornful laugh. “Hear that, Rebecca, he likes his dress! Oh my god! You chose well, my dear.”
“Boys or outfits, darling?”
“Both! I don’t know if I’m going to be able to keep my hands off them until after dinner.”
“Well do your best, Tamsin. If you start messing with them now, we’ll never get our dinner!”
“It’s your dinner party, Becca, so I’ll be good. For the time being.”
“Good girl, Tamsin. But the first course won’t be ready for half an hour or so. Do you remember what we were talking about earlier?”
“What, sex toys?”
“No! Not that, you bad girl! Gilbert and Sullivan!”
“Oh, that! Yes, I remember.”
“Why don’t we make them…?”
“Oh, yes!” cried Carmelita, “That’s a great idea!”
Rebecca turned to us. “Boys, do you know who Gilbert and Sullivan were?”
“Did they write operas, Miss?”
“Clever boy, Billy! Now, did you ever see ‘The Mikado’?”
We thought shook our heads.
“Carmy, can you get it up on Youtube again, please?”
Carmelita, skipped over to the laptop on the table, and soon we were watching a chorus from the opera – “operetta”, Rebecca called it – in which three ladies were singing a song about “little maids”. It was quite silly and funny.
“Do you think you could sing that?”
“Maybe,” I said, “but there’s only two of us.”
“Don’t worry. We can adapt the words. Tamsin, could you accompany them?”
“Sure. It would be a pleasure.”
“I have an idea. Boys, give us five minutes. Go into the kitchen – there – and help yourselves to what’s on the counter. You’ll find pizza and crisps and fruit, and there’s plenty to drink in the fridge. We’ll call you when we want you.
We retreated to the kitchen with relief. There was loads to eat, and we seated ourselves on stools and tucked in.
“Be careful not to get it on your dress,” Billy cautioned me. “I don’t think they’d be very happy, somehow.” So we found some napkins and covered ourselves with them.
“What do you reckon?” Billy asked.
“Ask me again later. It’s that Tamsin that I don’t like much. The other two seem fine.”
“Yeah. She looks tough, all right.”
“If we just do everything they ask we should be okay.”
“Depending what they ask,” said Billy, doubtfully.
After about ten minutes we heard the tune of “Three Little Maids” being played on the piano. We crept back to the door and peeped in. Tamsin was clearly an accomplished pianist, even though it seemed to us out of character. But she smiled at us as we watched her, and I began to modify my opinion of her.
“Come in, boys, if you’ve finished. I mean, girls, of course, said Rebecca. “Take your time – I know you’re a bit unsteady on those heels.”
We made our way carefully over to the piano. Rebecca handed us a sheet of paper.
“You heard the lyrics just now, but we’ve modified them slightly to suit the circ-umstances. There’s only three verses and I want you to learn the words so you can sing them without looking at the paper.”
We read the new lyrics together. Whenever I hear that tune, these are now the words I think of.
Two little maids from school are we,
Pert as a schoolgirl well can be,
Filled to the brim with girlish glee.
Two little maids from school.
Two little maids who all unwary,
Each dressed up as a little fairy,
Panties quite extraordinary.
Two little maids from school.
Two little boys turned into missies,
A fine little pair of proper sissies,
Longing to start exchanging kisses.
Don’t you think we’re so cool?
Don’t you think we’re so cooool?
We looked at her aghast.
“Here, I’ve made a copy so you can both have your own. You’ve got ten minutes. Then you’re on.”
Tamsin smiled at us sweetly, playing variations on the tune to pass the time.
“Well don’t just stand there, get learning. Repeat the words to each other till you have them perfectly. Any mistakes and you’ll be sorry,” said Tamsin, emphatically. She nodded towards Carmelita, who had acquired a dressage whip, which she swished threateningly.
“Yes, boys,” she said, “I know how to use it. And it’ll be across the backs of your legs – both of your legs – if even one of you gets a word wrong.” This from the girl I had thought so nice and friendly.
Needless to say, we had the whole thing off pat well before time was up. Then we had a rehearsal, and though we were word perfect, we were also tone deaf. Until, that is, Carmelita applied the whip to the backs of out thighs. The pain was sudden, intense, and lasting. We dared not risk a second stroke in the same place. We both yelped, and Billy would have toppled over if I hadn’t grabbed him. But it made us sing, and somehow we got pretty near the right notes. When they had schooled us to their satisfaction, Rebecca made us stand next to the piano. Then she knelt down and carefully linked the padlocks on our ankle-straps together, so that we were close together. Then we were made to hold hands. The final indignities were, that when we sang “panties quite extraordinary”, we had to use our free hands to lift our skirts right up and show them. And after the final “cooool”, we had to turn to each other and kiss on the lips. “And hold the kiss till I say you can stop!” added Rebecca.
We did it. All of it. Several times. Rebecca filming on her phone, which she put on a tripod. When at last we were done, Rebecca separated us, and placed us a few metres apart. Then she padlocked our ankles firmly together. Neither of us could take even the tiniest step. We had to stand immobile, watching while the ladies picked the best take. At last they were agreed. They seemed delighted with the result.
“Well done, boys. This is absolutely fantastic.”
Rebecca plugged her phone into the laptop, and we got to watch our own performance. It was quite polished, but utterly, devastatingly, embarrassing. Totally humiliating. But they seemed so thrilled I almost felt proud of us! Until, that is, Tamsin said,
“Where shall we upload it, then?”
“Both their Facebook accounts. I have their details from the committee.”
“What?” I shouted. “No! You can’t! Please don’t! You f***ing can’t!”
The ladies looked at each other for a moment, then Tamsin strode over to me and slapped my face, hard. Tears welled up in my eyes, more from shock than pain.
“How dare you? How dare you speak to us like that! Carmelita, three strokes, please!”
Unhesitatingly, the pretty, sweet-natured Carmelita picked up her whip and approached me with an innocent smile playing on her lips. She stood at my left side, and with undisguised relish applied the thin whip to the backs of my legs. Three cuts, a few seconds apart, using its whole length. I nearly fainted with the pain, and was unable to stop myself sinking to my knees, sobbing. Tamsin stood over me.
“Well? What do you have to say for yourself?”
“I-I’m sorry, M-Miss,” I blubbered, “please forgive me. It won’t happen again… I promise.”
I was now on all fours, crouching at her feet. She seemed somewhat mollified. She looked down at me, regarding my tear-stained cheeks with an expression of triumphant satisfaction.
On a whim, it seemed, she went and sat in the nearest armchair, her feet on the floor,
“Come here, boy.” With my ankles still tethered, I had to almost drag myself over to where she sat.
“Kiss my boots,” she ordered, quietly. I looked up at her in mute entreaty.
“Do I have to tell you a second time?”
Obediently I began to kiss the shiny rubber.
“Lick them,” in the same quiet tone. “Lick them as if you’re licking up your friend’s sperm, which you like so much.”
I licked enthusiastically.
“Listen carefully. On that laptop there are now two episodes of your behaviour. One is your little performance today. The other is your performance at Harriet’s party last week. If you don’t want your friends to see what you did so prettily today, then we can easily substitute the other one. Make your choice now.” I didn’t hesitate.
“Please Miss, upload our performance this evening.”
“Are you sure, Simon? You’d really like to show it to all your friends from school? Oh, and all your fellow Scouts?”
“Absolutely. I beg you to upload it at once.”
“I thought you might. Go ahead, Carmy. Hit it!”
“Simon! How are we going to explain it?” wailed Billy.
“Well, Billy, I’ll tell you what. We’re going to allow you two to write whatever supporting text you like. You’re very inventive boys. I’m sure you’ll come up with an explanation. You can say it’s for Halloween, or it’s a satire on Gilbert and Sullivan – though I don’t suppose most of them have even heard of Gilbert and Sullivan. Or you can tell the truth – that you’re a pair of big sissies and you’re in love. We’ll be interested to see what you come up with.”
“Yes,” added Rebecca. “The videos live now, so you’d better hurry. You’ve got ten minutes before you need to start serving dinner.”
Betty Pearl's Sissy Stories 20.1
Topic: Simon (Read 40351 times)
