Disable your Ad Blocker! Thanks :)
Chapter 39
by
Obedient Lorelei
What's your solution?
Call in a favour
You send a quick text to your teaching assistant, asking her to pick up the whip and bring it to you in Dr. Blake's room. She replies immediately right away, Professor, knowing from painful personal experience exactly which one you mean. While you're waiting for her to get here, you offer to take a turn with the paddle so Sharon can have a rest.
There seems not to be much point having Tilly change position, so you begin with ten swats, with her lying on her back, exactly as she is. Currently, her right cheek is much more bruised than the other, because her former tutor is right handed and naturally spanked forehand, meaning the buttock struck by the end of the paddle suffered worse than the one closer to the handle. You find that chastising one side of a girl more than the other is often particularly effective, so you decide to administer yours in the same orientation. It doesn't take long for you to be proved right, as the attractive young woman weeps piteously between every smack, nearly hysterical with pain. By the end, her right cheek swollen almost into a cone, a white blister at the tip. Dr. Blake looks impressed. Your paddling was slightly harder than hers, but you're not the least bit out of breath.
"Shall I take over for a bit, Jack?"
"If you like, but I thought you might want to save yourself for the whip."
"Oh, yes, maybe that would be best…"
Just then, you're interrupted by a knock at the door from Erin, the grad-student you sent for the whip. It startles both of you (Tilly is too distressed by her throbbing rump to notice), because you were expecting her to take a few minutes longer.
"Come in," Sharon opens the door and then closes it behind the smartly dressed brunette.
"Hello, Professor, Dr. Blake. Here's the whip you asked for." She proffers it in your general direction, unsure which of you actually needs it.
"I'll take it, thanks, Erin," you say. "Would you mind holding on for a bit. We might need your help later."
"Of course, Professor. Anything you need." She smiles warmly.
You take the lash and stand to the side of the tormented twenty-something. Instead of whipping downwards, you rotate your wrist, causing the flexible rubber cord to whirl in a lazy circle, which you bring steadily closer to Tilly's **** pudenda until the tip strikes her directly on the clitoris, where it seems to grip momentarily, dragging the sensitive nub upwards and causing quite exquisite agony.
The graduate chokes on her own breath, eyes wide with disbelief at the intensity of the sensations assailing her, but the curved path of the whip is barely disturbed by the impact and you're able to make it hit the same spot on the very next rotation. Tilly's entire body convulses, but you land a third direct hit and she loses all self control, thrashing helplessly on the table and blubbering in anguish.
"Hold still, girl," you admonish, irritated. "You were taught better than that."
However, it takes a few moments for her to come to her senses whilst you tut in dismay. Finally, she's ready to continue and whimpers an apology that you can barely understand.
"Spread yourself open so I can get at the entrance to your urethra," you order, remembering that she said her pee hole was particularly sensitive to pain. In response the young beauty mewls in terror, but still obeys and you resume the swishing of the lash.
Although your target is trembling uncontrollably, you still manage to get the tip of the whip exactly where it needs to be and Tilly retches from the pain searing into her core. Her whole body tenses and the next rotation hits her swelling purple clitoris again, making her jerk rigid, then on the next hit, she starts to writhe again. With a sigh, you wait for her to still again, all hope of getting an intelligible count out of her abandoned for the time being.
"Erin, would you mind holding Tilly in place?"
"Not at all, Professor." As a teaching assistant, she's used to helping out with chastisement, although usually of younger women, rather than those a few years her senior. She shows no curiosity as to why a young woman is being flogged so viciously. If you're involved, there must be a good reason.
The accommodating postdoc hops up onto the table spryly, sitting on top of the other girl and using her legs to pull Tilly's apart, then she delves deeply into her sex, spreading her even wider than before. The former student slumps back, apparently relieved that she can hand responsibility for staying in position over to another.
"Sharon, would you like a go?"
"Oh, yes, please, Jack. It looks most effective."
"Indeed and if your arm gets tired, I'm sure Erin would be happy to swap over for a while."
"Absolutely, Professor," she replies, although you can't really imagine the staid and respectable tutor taking her place to hold Tilly still. She might be afraid of getting her fingers whipped by mistake, but you know that Erin can be trusted with accuracy, which turns out to be more than can be said for the doctor, as her first attempt strikes both knuckles and cunt.
You wince, but your well-trained grad student shows no response, staying perfectly still and waiting for Dr. Blake to find her rhythm. Tilly, meanwhile is almost the opposite, trying to buck and twist, but too weak to dislodge the girl on top of her. She screams at a low volume, due to a combination of exhaustion and having a person sitting on her diaphragm.
You continue to watch until you're satisfied Sharon has the hang of it. You think the visitor is trying to say something, but there's no way to tell what. If she's ready to change her mind, she'll just have to wait until her former tutor is ready to hear it.
"I'm going to get lunch," you announce to nobody in particular. "I'll be back in about half an hour to see how you're getting on."
"Thanks, Jack," Sharon calls over her shoulder, whilst her target's shrieks get more animated. "I'm sure we'll be getting somewhere by then."
What's happening when you get back?
Disable your Ad Blocker! Thanks :)
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
You can customize this story. Simply enter the following details about the main characters.
- 140,892 Likes
- 58,910,292 Views
- 8,542 Favorites
- 31,656 Bookmarks
- 6,701 Chapters
- 71 Chapters Deep
- All Comments
- Chapter Comments