Surprisingly well (but then the punishment is mild)

It is your turn to help someone onto the machine and cuff them in. Lorelei is clearly terrified, but also fully compliant and you can sense a degree of anticipation too. It is almost as if she expects a part of her will feel better after the ordeal is over, which may well be true. Like you, she has an itch to be scratched and seemingly even in this world circumstances are so she does not get enough of it. Well, that much is about to change now that she met a certain paddle-happy someone. You and Diana move around the frame, fastening and securing the straps, making sure they are tight but not overly so. With an “ah!” of someone who just remembered something, Mr Brown stops typing, returns from his desk back to the AutoSpanker and replaces the single arm with a large paddle with two smaller ones each holding a shorter paddle and positioned on both sides. A moment later the reason becomes clear, as he adjusts the dildo too and guides it between the redhead’s open pussy lips. It is to remain inside her (if only just) even when stationary, providing extra restraint and making sure it will find its target even if the poor victim moves. The paddles can work on either side of it undisturbed.

“Ms Cho, please check the parameters and start the programme.” Mr Brown asks you to your surprise as he finishes fiddling with the artificial arms and presses a remote identical to the ones you and Diana held earlier into Lorelei’s hand. “Ms Hart, unlike in the earlier punishment, this will not be secured and if you drop it, the machine will simply continue in the same mode until the end.” he informs her. You shudder at the prospect and start making your way to your colleague’s and disciplinarian’s desk, still unsure why would he ask you to start the machine in his place and especially check the parameters of the punishment. Your best guess is that in this world being naked and freshly spanked to tears is not a reason to be dismissed as a colleague, and a knowledgeable one at that. The main part of your punishment is over and you are back to being colleagues, some paperwork and clothes return aside.

You tilt the screen upwards so you can see it clearly without lowering your bruised bottom onto the chair. The punishment is set for ten minutes with medium power strokes every six seconds and a high setting for the dildo. You do the maths quickly in your head; if Lorelei can hold out without orgasming for over seven minutes she’ll get off easier than you did, and by some margin too. That sounds doable, given the level of pain she will be in. You are quite happy for the girl, even though a part of you wants to see her properly squirm for being so eager to end up here in the first place. The punishment is set to start with a spanking and you are happy to leave that switch there.

You look up at Mr Brown again and seeing him nod, press “enter”. The screen changes to leave the message that the machine starts to speak out and a huge “ABORT” button. After describing the punishment again in dry HR terms, the AutoSpanker starts the countdown. Lorelei is trying to brace yourself and with a mix of pity and amusement you realise she does not actually know what will happen first, the mechanised voice only gave the two punishments’ names, not their order. You decide to stay behind the computer, something (perhaps the Rulebook, perhaps common sense) suggesting that if there is an abort button for a machine with parts moving at a high velocity and striking a person secured on it, someone should stand ready to press the said button. Also here you can give your bottom a quick and careful rub without attracting anyone’s attention needlessly.

Lorelei lets a little squeal of anticipation as the countdown ends and seems to shift herself to let the lubricated dildo slide in painlessly... but it stays still as you knew it would and instead the two smaller paddles strike together, turning the squeal into a little yelp. The paddles do not hit as hard as the large one did for you and Diana but full ten minutes on it would still be impossible to bear. You only see a half of one of Lorelei’s bum cheeks from where you stand but it is enough to see the immediate redness. Amazingly six seconds give Lorelei enough time to recover from the initial surprise and she takes the next stroke is dignified silence. Well, dignified for someone with her breasts and bottom sticking out in a most revealing position in front of three near-strangers. She clearly meant it when she said she genuinely is seeking discipline though, as she continues to stay still and present the same spot to the merciless paddles. You know she cannot last long like that - nobody can - but the effort is impressive nonetheless.

The the redness grows deeper and gives way to something closer to burgundy, the punished redhead finally yelps again and does not manage to return to being quiet this time, soft moans alternating with more vocal reactions every time the paddles strike. And yet she does not press the button, presumably wanting to push herself to her limit before switching to the less painful but potentially disastrously-ending mode.

Finally, just over three minutes and thirty-something strokes into her ordeal, Lorelei does it. After a particularly pitiful squeal you can see her muscles straining and mouth gulping for air and although you cannot see her hand on the button, the paddles draw back and freeze there. Instead a new whirring sound begins and the dildo positioned at the entrance to the exposed pussy starts sliding in. Lorelei gasps but you feel it is mostly the change in sensation rather than pleasure that causes it. Indeed, she manages to subdue her reaction and stays limp on the frame, allowing the device to penetrate her, probably enjoying the (likely temporary) end of the spanking more than the fucking itself.

The effects cannot be ignored forever and even from where you stand you can see Lorelei’s muscles starting to get tense and her expression change from that of relative relieve to strain. Marginally at first but then more and more as far as the straps allow her hips start to move to meet the penetrating device. She catches herself and strains to stop but soon finds herself unable to stay still again. You glance at the timer having lost the track of time somewhat and discover roughly another third of the punishment has already passed and Lorelei used the switch only once. You can tell the second time is nearing though, as the redhead’s face grows progressively redder too and her thighs squeeze the frame despite her presumably best effort. If you know anything about girls’ faces while nearing an orgasm (and you like to think you do), she is either deliberately risking holding out until the last possible moment or actually forgot about the rules overwhelmed by the immediate sensations.

It turns out to be the former as the dildo suddenly stops; Lorelei’s bound body tries to still reach after it but the paddles come back into action, making the girl howl with frustration and pain (you know from experience how bad spankings on an already sore target are). Still, the sensation in her pussy must distract her enough as she takes the resumed paddling far better than you would have expected under the circumstances and the time of her sentence is ticking away fast, even if she won’t feel it that way. Not that she knows how long the timer was set for anyway.

Lorelei holds out for another portion of the spanking, similar to the first. You can see fear and despair joining the expression of pain on her teary face as she realises she is nearing her reasonable limit again and she must switch into the risky dildo encounter anew. When she finally does, however, it turns out she need not have worried; the dildo moves only twice under her battered raw cheeks before the machine stops, its voice announcing competition. Mr Brown helps her out himself after allowing a minute to sob limply into the cushion.

Once Lorelei is up he asks the three of you without further delay to take seats on one side of the conference table which you do to your immense discomfort. Normally you would be very interested in taking a more detailed look at the forms in front of you (Lorelei’s is slightly different presumably on the account of her being a visitor rather than an employee) but now, anxious to be out of the chair again, you just fill in your details and tick whatever boxes feel right as quickly as you can. Other ladies seem to share your approach as the forms get filled and put into the cabinet in no time. Mr Brown tells you and Diana you can collect your clothes from him tomorrow morning (he does not need to mention you must arrive nude) and wishes you a good afternoon; he asks Lorelei (whose clothes are still secured out of place) to stay behind to explain to her how disciplinary arrangements for non-employees can be made. Before you know it, you and Diana are back in the hallway, strangely feeling perfectly fine by now with your entire attires consisting of shoes and handbags.

“Our evening is still on, right?” Diana asks. Instead of replying, you throw your arms around your naked friend.