[willingmale]

Punishment time - I have to do this tomorrow for failing a previous task and have been ordered to post our conversation about it for everyone else's amusement, so here it is (I did not roll/flip, they were assigned to me)


[22:15:44] willingmale: just wanted you to know that after tomorrow, my arse won't be the same for ages


[22:16:13] willingmale: I know a deals a deal but its way more than you did and you said you've not recovered yet


[22:16:22] willingmale: how long ago was yours?


[22:18:04] Submissive9: Oh it was only this morning.


[22:18:13] Submissive9: Thats why I haven't recovered


[22:18:31] willingmale: was your dildo bigger than mine? (the one i'm going to use)


[22:18:51] Submissive9: Way bigger


[22:20:08] Submissive9: So suck it up and do the task


[22:20:13] willingmale: so lets sum up my fate - first set up webcam to video it all


[22:20:19] willingmale: next strip naked


[22:20:50] Submissive9: Yes


[22:21:01] willingmale: then roll a 6 - no lube!


[22:21:11] Submissive9: Yes


[22:22:14] willingmale: then a 2 - Forcefully ram it in as far as it can go - that's really going to hurt given its size and no lube


[22:23:21] willingmale: next roll is a 1 - so i need to fuck my arse slowly and deeply 200 times


[22:23:36] Submissive9: Yes


[22:25:09] willingmale: lube's running dry now, time to roll again, and its a 6 - still no lube allowed


[22:25:37] Submissive9: Correct


[22:26:24] willingmale: Now its time for the real fucking to begin, lets roll to see which positions I'm going to be fucked in


[22:27:45] Submissive9: Yes


[22:28:36] willingmale: its a 6 again! that means I am going to be fucked On my back legs in the air AND On my belly AND On top humping down on it AND On my side in the foetal position AND On my hands and knees


[22:29:10] Submissive9: Yes


[22:29:20] willingmale: Jesus, lets hope I don't have to do it much, time to roll again


[22:30:09] Submissive9: Yes


[22:30:51] willingmale: 3 this time, so for each position I need 600 moderately deep, moderately fast pumps - damn


[22:31:48] willingmale: That's 3000 pumps, and I've already done 200 - this will take quite some time to recover from


[22:32:43] Submissive9: Yes I can't wait to see this. It will be excruciating in the moment but it won't take as long as you think to recover


[22:32:45] willingmale: but when its over, it'll be time to toss a coin


[22:33:37] willingmale: and lets see what it is .... its..... Heads


[22:33:46] Submissive9: Haha yes


[22:35:23] willingmale: that means get fucked again! So I roll for the position I roll a 1 - On my back legs in the air


[22:36:38] Submissive9: You will be in so much pain. By the way I think I forgot a number. If I did it will be a one ok?


[22:39:40] willingmale: looks like I misread it! after flipping heads, I only re-roll the previous dice for the number of additional fuckings, not for the position


[22:40:22] Submissive9: Yes that's correct. Continue


[22:41:41] willingmale: that means the 1 I rolled means 400 fast deep pumps in every one of the five different positions. I'm now up to a total of 5200 pumps - will my arse ever be the same again/


[22:42:46] willingmale: and now to the finish - I roll a 6 which means...


[22:43:16] willingmale: ...keep it in for another hour, then roll again


[22:43:33] willingmale: Will this heinous task ever finish?


[22:43:55] Submissive9: Yes it will end soon


[22:45:18] willingmale: an hour later I roll again and get a 4 - I have to keep it in for a min, then take it out and suck it clean, then return it to my ass for 5 more mins of fucking, then bring it out and cum on it, and suck it clean again


[22:45:31] willingmale: and then I can relax!


[22:45:51] Submissive9: I told you yesterday before you failed a task that the punishment would be far worse. Well I wasn't lying was I?


[22:46:56] willingmale: no you certainly weren't - shall I add this conversation to Sexdemon's Anal Hell thread for other people's amusement


[22:48:00] Submissive9: Yes do that now

Wish me luck people...