I do love a good sissy training tale :)
“Please what Nick? Or is it Jessica right now?”
“God. Please…I need….to cum.”
Ms Brigitte laughed, softly at first, and then louder, knowing what that would do to him. It excited him almost as much as it did when she called him names. Names like Jessica.
“Right now? Does my little slut Jessica need to cum right….this….instant?”
“Please…please. Now…and…I just…I need to cum MORE.”
Now she REALLY laughed. She knew this was coming (and she laughed at her own pun), but just hearing that from Nick’s lips, from his painted red lips…it filled her with a warmth that she savored.
“What ever do you mean, sweetie?”
“I…I…I’m just all tense and frustrated all the time. I just can’t concentrate. Please, can I PLEASE cum more often?”
“Ooooh. That is a VERY big request for a sweet little girl. But you know I do love when you ask me things. That pleases me very much.”
“Please…PLEASE. I just need to cum more often. Please. Will you please let me?”
“Hmmm. I suppose we could work something out. And I’m even feeling generous. What if I even offered to let you wear boxers again?”
Nick blushed visibly. “For real?”
“Yes Nick…I mean Jessica.” Did he just blush even harder? It was so freaking delicious.
“What do I need to do? Please…PLEASE.”
It almost sounded like his voice was getting higher…this was intoxicating.
“Well Jessica…I have been thinking. You’ve been pretty good whenever you’re my sweet little girl. And you’ve been learning do to SUCH slutty things when I make you be my whore….but…well..there’s a difference between learning…and training, isn’t there?”
He couldn’t answer. It was too much. Just too much.
She went on. “You see Jessica, I’ve been thinking. You wear panties for me every day. You are…used to it. But I don’t want that. I want you to CRAVE it.”
“Actually Jessica – I want you to crave more than that.”
“So…here is what I am going to offer you. You can cum…any time you want. And I mean that – you can spend all day in your princess bed and just touch your little clitty all day long if you want, and I KNOW you want to.”
Nick/Jessica couldn’t hide it. He blushed…but nodded.
Ms Brigitte smiled. He was too precious. “You can cum any time you want. BUT…and pay attention to this – you will ONLY cum if you are wearing panties.”
She wasn’t finished. “Panties…and heels.”
“I…I don’t understand.”
“What’s to understand sweetness? You can cum every time your little heart desires, but you will put on clean panties…and pretty shoes, before you do.”
“I….I can do that,” Nick stammered.
“Shhh….shhh….hold on. It’s very important for me that you understand this. And that’s because I want to enjoy this gift you’re about to give me as much as possible.”
She stroked his face. “Oh yes. Because you’re going to agree to this. We both know you are. But you’re going to agree to it with full knowledge and acceptance of what you’re doing.”
“You see…Jessica. I am going to train you. I am going to train you to YEARN to wear panties. I am going to train you that every time those sissy panties touch your little clit, and every time you walk around in slutty heels that make your feet ache to deliciously….that you will feel pleasure.”
“I am going to TRAIN you to associate panties…and heels…with cumming. I am going to train you, so that every time you touch your little clit, you go further and further down that rabbit hole. You can fight it all you want, but we both know it will be inevitable. One day you will wake up, and you will simply want to wear panties and heels for me. And I am betting that day is very, very soon.”
“Put simply Jessica – I am training you to have a women’s shoe fetish. Among other things.”
“Three other parts to our little deal, before you go up to your little canopy bed. You can cum whenever you want, but after you do you will send me a picture of your pretty little feet in whatever heels you are wearing. And after you cum 10 times….I expect you to buy a new pair of heels. I cannot WAIT to see how big your shoe collection gets in the next 3 months.”
“Three months? Why 3 months?”
“Because, Jessica – in 3 months…you’ll only get to cum if you’re wearing panties and heels….and a skirt.”
I just love dressing up my sweetheart sissy girl, Jessica. Besides, the transformations that stick are the ones that start out subtly and work their way in.
Have you ever found yourself being transformed into a sissy through sexy lingerie and tease and denial?”
It could only have been about fifteen minutes, but she couldn’t check her watch as she had her hands on her head, facing the wall, outside the headmistress, Miss Brigitte’s, office. Fifteen minutes, but it felt like an eternity.
She had started out fourth in a line of miscreants, and now it was down to her. Two girls had already come and gone, dispatched from the office in varying states of distress. Now it was the turn of the third girl, Roberta Jamison, and she had been in there an age. Sissy Miranda was musing on why this might be when, suddenly, the heavy mahogany door of Miss Brigitte’s study swung open, and out stepped Roberta. ‘Your turn now,’ mumbled the girl to Sissy Miranda, ‘she wants you in straightaway.’ Sissy Miranda turned round, managing to raise a brief half-smile to her tear-stained fellow, before knocking on the dreaded door herself.
Miss Brigitte was sitting behind her desk, a fine, crook-handled cane prominently on display before her. This was a weapon Sissy Miranda had become familiar with over the past few years – that and, of course, the strap. She did not know which she hated the most, but having tasted the bite of both, she was at least prepared for their sting: Miss Brigitte couldn’t really hurt her.
‘Well Sissy Miranda, I haven’t seen you in my office for a while,’ began Miss Brigitte. Sissy Miranda remained silent.
‘I assume you have a note?’ continued Miss Brigitte.
Sissy Miranda stepped forward and held out the note she had placed in the top pocket of her blazer.
‘Cat still got you tongue I see,’ went on the Head, as she picked up her glasses and read through the missive.
Sissy Miranda said nothing.
‘Well, this sounds like a very childish offence,’ asserted Miss Brigitte at last, surveying the tall fifth-former before her.
‘Go and fetch me that chair,’ she suddenly instructed, indicating a low wooden chair near the window, ‘and put it in front of the desk.’
Sissy Miranda didn’t move.
‘Do it, right now!’ commanded the Head.
Sissy Miranda’s feet obeyed, despite her mind reeling in confusion: this was not how she took the cane, or the strap for that matter.
Miss Brigitte stood up, waited for the chair to be settled, then sat down.
‘Come here and bend over my lap.’
Again, Sissy Miranda didn’t move.
‘Come here at once,’ continued Miss Brigitte, her voice rising to a crescendo, ‘or I will spank you harder and longer.’
Spank? Sissy Miranda was horrified: she had never been spanked before; never had to lie across the lap of the head mistress – this was too much.
‘Come here!’ ordered Miss Brigitte, and this time the girl did move, approaching the Head and then lowering herself carefully over her lap as indicated.
Before she could do anything else, Miss Brigitte had pulled back her skirt, pulled down her pink frilly panties and slammed her hand down hard on her behind.
‘Ow…ouch!’ issued from Sissy Miranda’s lips in shock, as another blow, and another rained down.
‘Be quiet!’ ordered Miss Brigitte, Sissy Miranda gritting her teeth as the blows increased in intensity; ‘This is not your place to speak!’