Part One is here 💋
I resumed my interview with her, Chapel - now back in place as cameraman - ensuring he got all the best angles of the imminent exposure of her body.
“So, Courtney, you were saying… You’re Courtney Bailey - of the New Hampshire Baileys. You’re nineteen, and so far, you don’t care very much for your time here. Do I have that right?”
“Yes, Headmaster,” she said, with another pout. I had to rearrange my fiendish prick in my trousers once again as I imagined her full, pillowy lips sucking along its length. Soon…
“And why are you removing your clothes for us today?”
A trace of defiance still remained, “Because you told me I had to.”
“Try again, Courtney. Why are you removing your clothes today.”
As she started to slowly lower her skirt down her narrow hips, she paused a moment and then said, “Because I want to show you and Mr Chapel what a good girl I can be.”
“Much better, yes. Are you a good girl, Courtney?”
“Ummmm… I guess… I don’t know, Sir.”
“Not many good girls get sent here, Courtney. Although plenty of good girls leave here, one way or another. What have you done to be such a bad girl, Courtney?”
Her skirt was at her feet by the time she answered. Stepping out of it on dainty feet, she said “I’m not sure, Sir.”
As she removed her socks, I said, “Let’s try this another way, shall we? Fold your clothes and put them on the chair here as you undress.”
She did as she was told, giving me the faintest glimpse of her pert arse cheeks beneath the hem of her shirt as she turned back to the camera.
“How many cocks have you sucked, Courtney?”
Her fingers stilled against the button of the shirt that she was unfastening.
“I’m sorry, Headmaster?”
“There’s no need to apologise for sucking cocks, Courtney. Unless you’ve been terribly, terribly bad at it.”
I allowed myself a wink at Mr Chapel as I said this. He chortled immoderately, his giant erection already visibly straining in his trousers.
Courtney flushed, her blush spreading prettily across her cheeks. “I don’t know, Sir.”
“Have you lost count, Courtney? That sounds as though you’ve sucked a great many cocks. Have you, Courtney? Are you a filthy little cocksucker?”
Tears were once more spilling steadily out of her eyes as she carried on unbuttoning her shirt, her regulation white bra now quite visible, her sweet tits peeking out at me from the opening.
“Do I need to ask Mr Chapel to encourage you to answer my questions, Courtney?”
Choking on her tears, she hurriedly said, “No Sir… I think…” I enjoyed her struggle as she desperately tried to work out what number would satisfy me without getting her into further trouble.
“Maybe, five, Headmaster?”
“Are you sure of that, Courtney? A lovely young woman like you, I’m sure you have almost limitless opportunities for fellatio.” How I relished saying that word!
“I think so, Headmaster.”
“Your parents took the liberty of downloading your phone’s contents and sending it to me before you arrived. Are you quite sure that you wouldn’t like to think more carefully about your answer, Courtney?”
I nearly laughed out loud at her crestfallen face. Chapel leered from behind the camera. I sometimes think that this is his favourite part of the disciplining process - the humiliation of our students before their willing, sometimes grateful, submission.
Pressing another button on the remote, we all started to watch the video that Chapel had put together of all of Courtney and her various partners’ footage of their amorous exploits. It had taken him days to sift through it all and he’d had quite the spring in his step for that entire week.
There she was, on the 100-inch screen, deep-throating that imbecile Jaxon as though her life depended on it. Then others, and more again. Yes, Courtney was a cut right off the old Bailey block, that much was obvious.
Courtney started sobbing again. “My fucking PARENTS did this? This is fucking INSANE. Those fucking ASSHOLES. FUUUCK.”
Her misery was like perfume to me, I breathed it in deeply, eyes closed, savouring her total devastation.
“You seem to have forgotten yourself, Miss Bailey. Shirt off and let’s try this question again, shall we?”
Courtney looked briefly mutinous, casting her eyes around the room once more, in a desperate search for an escape route. With a sigh of resigned despair - exactly the same sound that her sister Chelsea had made in her first session with me, a gratifying wave of nostalgia making my prick even harder than I thought possible - she shrugged her blouse off her shoulders.
Finally, those glorious tits were presented to me. We were only moments away from their full exposure. As Courtney went to drape it across a nearby chair, Chapel and I exchanged a look, united in our gratitude for our access to these nubile young bodies under our care.
When Courtney stood before me once again, now in just her regulation white underwear, I repeated my question, “How many cocks have you sucked, Courtney?”
“About a hundred, Sir. I guess.”
“A hundred cocks, Courtney. A full century of cum-guzzling. I must commend your industry.”
She flushed once again. I watched it bloom across her chest, her little nipples visible through her bra. They would be receiving my attentions very soon.
“Why have you stopped undressing, Courtney?” I asked.
Her tight, voluptuous body was shaking as she reached behind her back to unhook her bra. I heard Chapel’s sharp exhale as Courtney’s magnificent tits finally came into view.
She really was a work of art. Her tits stood out, full and proud, just begging to be whipped and sucked; tawny nipples already hard, despite the warmth of my study. Just another Bailey Sister who loved to display her body to the male gaze.
After she had placed her bra with her other clothes, I heard Chapel unzipping and watched, amused, as he pulled out his cock and started to stroke it nonchalantly. Courtney looked horrified and froze in shock.
“You’ve stopped again, Courtney. Remove your underwear for us, there’s a good girl. Slowly, though. Mr Chapel enjoys the thrill of anticipation.”
Visibly gritting her teeth, Courtney started to ease her knickers down her shapely hips, the elastic tracing its way along her thighs. As her heavenly cunt came into view, I briefly thanked Mrs Bailey for instilling such fastidious habits in each of her daughters. Courtney’s pussy was as smooth and delectable as each of her sisters’, her silky slit spreading invitingly as she slid her panties off her slender ankles.
Her knickers now also cast aside, Courtney was trying valiantly not to cry again, her shoulders softly shaking as she fought to maintain her composure, her naked body was exposed to us. She somehow knew not to try to cover herself - few of the pupils in my study realised the punishments that would ensue if they attempted to avoid my gaze. Had she been warned, or did Courtney actually enjoy displaying her perfect, sun-kissed body to predatory male eyes? Time would tell…
Chapel groaned as he contemplated this naked vision before us, his cock straining alarmingly in his fist as he continued to stroke it rhythmically.
I decided to give the old boy a treat. He could have first go at her, I would enjoy watching his molestation of her pert young curves.
“Chapel, why don’t you inspect Courtney’s tits and let me know how they feel?”
Courtney made a choking sound and looked at me imploringly as Chapel tottered over to her, trousers around his ankles, briefs at half-mast around his thighs as his cock jutted out impressively.
“Miss Bailey, what a pleasure to become better acquainted with you”, he leered, his pudgy fingers already stretching out towards the perfect contours of her firm, plump tits.
Courtney cringed but stayed in position as Chapel’s hands started to cup her tits, a plump mound filling each of his hands.
His hands roamed freely over her smooth skin, fondling the soft flesh between his fingers, feeling the orbs tighten beneath his hands as he groped her thoroughly.
“Pull your shoulders back, there’s a good girl,” he instructed.
Courtney responded beautifully, unhesitatingly, thrusting her tits out further into his roving hands, pressing against them.
“Very good, Miss Bailey. Hands behind your head, elbows out,” Chapel said, getting Courtney to adopt the pose he favoured for inspections.
She complied immediately, seamlessly entering into an entirely submissive state.
“Very, very good. Now spread your legs apart. Wide.”
Courtney shuffled her legs apart a little. Lightning fast, Chapel swiped his hand down and slapped her sharply against the insides of each of her thighs. Courtney squealed, in shock as much as pain, and planted her feet widely apart, spreading her cunt lips delightfully.
“Much better, Miss Bailey. No more half-hearted efforts, do you understand?” As ever, Chapel spoke surprisingly commandingly for a chubby man sporting such a pronounced erection.
Courtney nodded, “Yes Sir, I’m sorry, Sir.”
She really was responding most gratifyingly to instructions. My cock jolted again as I looked forward to subjugating her myself.
Chapel ran his thumbs over her pert little nipples encouraging them to get even harder. Taking them between his thumbs and middle fingers, he twisted them slightly, then tweaked the hard points, making her wince and then sigh. Just like her sisters, Courtney couldn’t resist the thrill of being molested and used by men.
I smiled as I saw her pussy juices starting to leak down her newly spread thighs.
“Mr Chapel, it seems Courtney may require some attention to her greedy little cunt. Would you care to take a look?”
Chapel dropped to his knees, his eyes level with Courtney’s gleaming pink pussy. Once settled between her legs, he pushed her thighs even further apart. They strained out either side of him, the muscles stretched taut under her creamy skin as he ran his hands slowly along their smooth curves.
Courtney closed her eyes, mortified.
“Look at me, Courtney,” I said. “Face the consequences of your depravity.”
She fixed her gaze on me, trying her best to maintain eye contact as Chapel thrust two fat fingers inside her cunt, lewdly pumping in and out of her, the evidence of her arousal unignorable as he probed her sticky depths, the sound of her pussy juices sloshing noisily filled the room.
“Take care of her Chapel. From behind. I want to watch her cum,” I ordered.
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