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Chapter 38
by
Obedient Lorelei
How does Skylark fare pleasing you sexually?
Very satisfactorily
Taking a firm grip of one delectable earlobe, you drag the elfin beauty up the stairs. From past experience, you know that reemerging into the real world from the dungeon of your cellar can cause psychological trauma as your trainees realize that their ordeal is not some nightmare to be pushed into the darkest recesses of their memory, but rather a taste of what their future holds if their behaviour falls short of the required standard. It's while Skylark is still processing this unwelcome fact that you lounge back on your sofa and order her to show you what she's learned about pleasing a man.
Skylark immediately kneels, kissing your feet and begging to be allowed to take your manhood into her mouth. As soon as you give permission, the young beauty engulfs the head of your dick with her pouting pink lips, swirling her tongue across its surface before smoothly sliding it down her unresisting throat until her nose is buried in your pubic hair. You groan and throb with arousal. The training you've been giving her is certainly paying off and you don't expect to last much longer, but she seems to sense this and slips back off your prick with an audible pop to ask how you want to use her.
"I'll have your bum next," you tell the attentive girl, who responds instantaneously, straddling you and guiding you into her rear. The expression of utter agony on her pretty face as your meaty prick stretches her well-punished back passage is immensely gratifying, but no more so than the sensations of being massaged to the brink of climax by that skilled tunnel.
Skylark bobs up and down in your lap until you need another break and gently signal her to resume her oral ministrations. A few hours ago, this request would have produced a moue of disgust, but now the only emotion she demonstrates is her desperation to satisfy you, which is quite understandable, since she has no doubt guessed that failing in her duties will mean a return to the cellar. You soon need to swap ends again to avoid cumming too soon, but following the brutal beating of her genitals you administered so recently, you order her to fuck you in the more traditional manner.
The weeping resumes when she mounts your hips and impales her excruciatingly sore cunt on your rampant cock. You're sure this is not a sign of discontent at the instruction to pleasure you, but rather an indication that that chastisement you've administered is fearsomely effective. Personally, you find the flowing tears both attractive and stimulating, but you acknowledge that others may feel differently and resolve to mention this to her when she's finished. Then, you're too preoccupied by the sensations in your pampered prick to think about much of anything else.
A stunningly beautiful girl with an exquisite figure **** to bring you to orgasm is far from unusual nowadays, but the suffering blonde riding you manages to surpass even your jaded expectations. She gazes into your eyes as soulfully as a lover might, applying every inch of her tortured body to enhancing your enjoyment of her. She's a quick learner and her experiences with you, coupled with a few lessons from Bethany, have given her skills many women never achieve, so it's little surprise that she soon has you quivering as you spend your lust into her burning core.
You hug the agonized eighteen year old to you, caressing her welts and weals cruelly and listen to her profuse thanks for allowing her to show her gratitude for the latest thrashing you gave her, then give her a few more pointers concerning how to satisfy other men—she may have mastered your desires, but there's no reason to let her get complacent.
There's another test in store when you order her to help you shower and dress, but she manages to do so with no slips or mistakes. You're slightly disappointed to have no more reasons to punish her, but on the other hand, you're still feeling drained from your earlier exploits, so maybe it's for the best. Besides, there'll be another innocent nymph for you to torment next week.
You have Skylark get dressed, ready for her parents to collect, whilst you sign the report Bethany has written about your guest. The last six months has taught you to trust your grad-students' abilities, just as you rely on their help training the young lovelies sent to you, so you don't even bother reading it first. She'll also send a copy by email, after the parents have spoken to you and picked up their daughter.
In fact, you're cutting things a bit fine today, because it's not long before they arrive with a firm knock on the door. You answer it yourself (the personal touch is part of why you're so sought after as a daughter trainer and helps you charge more money for the service) and invite them in to your drawing room for tea and a discussion of Skylark's progress.
The parents seem a little anxious, maybe because it's the first time they've let their precious little girl stay out without calling; you're strict about having no contact during the course you offer. Their demeanour is not unusual, although you've encountered completely different reactions in the past, so you try to keep an open mind. Anxiety aside, they're both as you remember them from when they dropped Skylark off, a pair of very attractive and smartly dressed professionals in their late thirties. You hand over the report and start to go over your observations concerning their daughter.
A few minutes later, she enters with tea (prepared by Bethany) on a tray, placing it on the coffee table and then standing silent and submissive, eyes downcast, waiting for acknowledgement. There's no way to predict how these reunions will go, but today mother and father both continue to focus their attention on you, with no interruption to greet their offspring. Privately, this is what you prefer, but since they're paying you handsomely, you'd not complain even if they jumped up for hugs and all sorts of fuss in the middle of a sentence.
Still, it's time to wrap things up, so you finish your account with a speech you've practised many times over the past few months.
"As we discussed when you booked, the discipline I provide is just the start. It's important that you continue in the same vein if Skylark is to get the most out of her experiences here."
"Absolutely," her father replies, enthusiastically. "We've discussed it at length and decided that it would be appropriate for us to give her double the punishment she's received from you after we get her home." Mother nods in confirmation and from the corner of your eye, you see fresh tears flowing down their daughter's face, although she's disciplined enough that she doesn't make a sound.
"Excellent! You'll find details of all the chastisements I've administered in the report, there. I'll also see to it that you get a copy via email. Now, do you have any questions?"
It turns out they do not and soon the trio are on their way home. You wave them off at the front door, but unlike some families, they don't give you the satisfaction of seeing them start discussing recent events, instead sitting demurely in the car until they're out of sight. You have no doubt that such discussions will be happening soon, however, nor that they will be very painful and humiliating for the youngster.
"Are you ready, Professor?" Bethany comes up behind you, having ordered a taxi, as usual. You nod and exit the house, memories of the beautiful blonde already being replaced by thought about the students you'll be tutoring today. This early in the year, there are bound to be opportunities for vicious punishments and degrading tips, just the way you like it.
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The Rulebook
You find a Rulebook that lets you rewrite the rules any organization has to follow
A lucky protagonist stumbles across a magic book that lets them rewrite the rules.
Updated on Jun 10, 2026
by Ggnt
Created on Jul 27, 2017
by ashes2ashes
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