When i roll a 1 for Phase 5 i get so horny >:)

Ok so having completed anal hell and anal gaping sessions multiple times in the past, I decided to try this new challenge. Here are my rolls, the action, and the journey. I used a 9 inch long by 2.5 inch wide suction cup dildo

Phase 1- 5, naked
Phase 2- 6, nothing skip the step
Phase 3- 2, 2 fingers lube up well spreading lube around repeat 3 times, Pos. 4 over bed
Phase 4- 4, 2 fingers roughly for 3 min., Pos. 2
Phase 5- 5, Rough face fucking gag, deepthroat, and whack 2 min., Pos. 5 on stomach
Phase 6- 6, Slowly invade ass inch by inch while pleading no, take full length wait 10sec. and repeat 10 more times., Pos. 6 standing
Phase 7- 4, Half in, Most out at 50 Bpm. 3 min., Pos. 5 on stomach
Phase 8- 1, All in, Half out 58 Bpm. 3 min., Pos. 6 standing
Phase 9- 1, Insert 1 ice cube till melt. Relube, Remount
Phase 10- 2, All in, Most out 50 Bpm. 3 min., Pos. 1 All fours
Phase 11- 1, Clamps 1 per nipple(all I had) Re roll and Repeat Phase 10.
Phase 10- 2, All in, Most out 50 Bpm. 3 min., Pos. 2 on side
Phase 12- 3, Edge while continuing at own pace.
Phase 13- 5, Half in, Half out, Twist 160 Bpm., Pos. 6 standing
Phase 14- 6, All in, Most out 69 Bpm. 3 min., Pos. 1 all fours
Phase 15- 3, All in, 52 Bpm. Spank ass during, Pos. 4 bent over
Phase 16- 6, All in, Most out 100 Bpm. 4 min., Pos. 5 on stomach
Phase 17- 5, Coat with Icy hot re-insert All in, Most out, 100 Bpm. Pos 6 standing, must orgasm to stop.

I have successfully passed Anal reform school! It was one hell of a task however. I felt almost like it was unrelenting, and impossible at some points. I felt like my dice rolls got me in a lot of trouble with restarting Phase 10 and getting a few unlucky rolls. But thats just part of the game. Although I was feeling ok as Phase 8 started by the end of it my asshole was burning. The ice cube helped a little but, but redoing 10 pretty much the made it even sorer. The second time doing 10 I could feel my ass gaping and it was kinda staying like that. I did Phase 12 slowly as I could to give it a bit of rest. But Phase 13 is and was brutal. 160 Bpm. was very fast and with the twist I felt gaping again and going numb a minute in. It was only half way so that was good. I thought that the hardest part had passed. But the next one right after was full length on all fours just made the numbness spread deep. It was just burning and hurting, and I felt sore and tired. I really wanted to finish so I tried to ignore it. The spankings were actually really not bad because of the numbness. But I felt my poor hole throbbing loosely open. Phase 16 was tough and I felt the last few minutes dragging by just trying to stay up with the beat. I was relieved when it was done not thinking about 17. As soon as I heard the icy hot, that icy cringe developed. I managed to work it all the way down, but the pace made it feel like molten lava was burning inside me. I didn't think there were was any possible I would cum from it. But then the numbness returned and the burning turned to cooling. I got an erection and jerked my way to victory. I collapsed and just rested with the dildo still inside me. I can say that even after 3 hours and a good shower my ass still feels lose from the dare. This was truly a consuming process. But totally worth it. So thank you for the sore ass, it's been a while since I earned the hard way.

Thank You.
 

I'd like to thank you all (and the many yet to come) for participating in this challenging dare. It was very fun to write and more fun to read your responses.

My question to all of you is, "what would you like next?" I'm open to suggestions for my next tormenting instructions. Would you like me to stretch your delicate pussies? Wear out your cock through an evening of pleasure and pain? Milk your full round breasts?

Be sure, I will be posting more, but do let me know what you would like. Be warned... if you make the suggestion that I write, you MUST participate.

Regards,
Your friendly twisted Doctor.

Next event
 

Thanks for the fun. I am all for the " Wear out your cock through an evening of pleasure and pain?" see where you can take that. Also expand on what we have to do with the dildo.

Thanks again

Can someone roll for me for this, and be super nice and tell me the dares that correspond with the numbers??

Skip the edging and orgasming, and no clamps :P

Phase 1 For Dress = 3 - Shirt and underwear/panties only
Phase 2 Punishment = 2 - Stand with a penny between your nose and a wall for 4 minutes
Phase 2b Position = 3 - On your back with your knees pulled up you your chest
Phase 3 Preparation = 5 - Use the finger and thumb of one hand to spread your anus and drizzle lubet into yourself.
Phase 4 Stretch = 2 - Use two fingers gently for 3 minutes.
Phase 5 Your dildo = 4 - Face-fuck yourself. Hold your head still and press the dildo into your mouth. Start slow and work your way up to deepthroating it. This will happen for two minutes.
Phase 6 Beginning = 6 - You are most unlucky. Press the tip against your anus and moan aloud "please, no..." then slowly, inch by inch, completely impale your ass. Wait 10 seconds and them completely remove it. Repeat 10 times.
Phase 7 Fucking = 1 - Thrust the dildo half way in, and almost all of the way out. 3 minutes at 40 bpm
Phase 8 More = (position 2 on side) 2 - All of the way in, most of the way out, 50 bpm, 3 minutes
Phase 9 Cool down = 1 - Insert 1 ice cube until it melts
Phase 10 Dildo again=(position 4 on bed ) 1 - All of the way in, half way out, 58 bpm, 3 minutes
Phase 11 Punishment (skip per your request no clamps) I rolled a 5 on this one
Phase 12 Pleasure (skip per you request on no edging) - I rolled a 3 on this one
Phase 13 Drilling with dildo (position 3 on back like you started)= 5 - Halfway. Twist at 160 bpm, two minutes
Phase 14 Sore check = 6 - Unlucky. All of the way in, most of the way out. 69 bpm, 3 minutes.
Phase 15 More Pain (skip per your request no clamps) I rolled a 2 on this one
Phase 16 More Fucking = 5 - All of the way in, half way out, 92 bpm, 4 minutes
Phase 17 The end (skip at your request because of no orgasm) I rolled a 2 on this

Good luck…was your roller broke? Just checking on why you could not roll yourself 

So, how did your fun evening go, Ms. Stockton?

Phase 1: Dress
5 - Completely naked

Phase 2: Introductory punishment
6 - You are lucky. You escape punishment
1 - On your hands and knees

Phase 3: Preparation
5 - Use the finger and thumb of one hand to spread your anus and drizzle it into yourself.
1 - On your hands and knees

Phase 4: Stretching
5 - Gently insert one finger for 1 minute, then two fingers for 1 minutes, and then three fingers for 1 minute.
5 - On your stomach with your legs together and a pillow under your hips

Phase 5: Your dildo
6 - You are lucky. Skip this phase.
4 - Bent over your bed (or chair, table, desk, etc)

Phase 6: It begins
4 - In one motion, slowly insert it two inches. Wait 10 seconds and then quickly pull it out. Repeat this 20 times.
6 - Standing

Phase 7: Fucking
5 - All the way in, half way out. 3 minutes at 50 bpm
2 - On your side with your knees pulled up to your chest

Phase 8: More
6 - Unlucky. All of the way in, most of the way out. 69 bpm, 3 minutes.
6 - Standing

Phase 9: Cool off your ass for a bit
1 - Insert 1 ice cube until it melts
2 - On your side with your knees pulled up to your chest

Phase 10: Back to the dildo
2 - All of the way in, most of the way out, 50 bpm, 3 minutes
3 - On your back with your knees pulled up your chest

Phase 11: Punishment
6 - More ice. Insert one ice cube and then reroll phase 10, fucking yourself while the cube melts.
3 - On your back with your knees pulled up your chest

Reroll Phase 10: Back to the dildo
5 - All of the way in, half way out, 69 bpm, 3 minutes
6 - Standing

Phase 12: Pleasure
4 - Edge yourself twice.
1 - On your hands and knees

Phase 13: Drilling
4 - Insert the dildo one inch and leave it there. Twist it 180 degrees each time the beats hits at 160 bpm. Two minutes of this.
5 - On your stomach with your legs together and a pillow under your hips

Phase 14: Are you sore yet?
2 - All of the way in, most of the way out, 50 bpm, 3 minutes
3 - On your back with your knees pulled up you your chest

Phase 15: More pain
5 - Coat your cock or vulva with toothpaste, insert the dildo completely and stand in the corner for two minutes. Clean it off afterward.
6 - Standing

Phase 16: More fucking
6 - Unlucky. All of the way in, most of the way out. 100 bpm, 4 minutes.
1 - On your hands and knees

Phase 17: The end
5 - Coat the dildo in toothpaste and insert it completely. Bring yourself to orgasm.
1 - On your hands and knees

Hello

I am new to this but want to do this dare.
Can you suggest the size of a dildo for me please, I fingered myself with 2 fingers and it already hurt.
Please advise.

You, sir, are EVIL!! I had to put toothpaste on the dildo and it BURNED!! Even I, with my high pain tolerance and masochistic nature, could not handle it. :eek:

Holy crap.. heads still spinng... shall come back later :)

1 - Dress formally. Men should wear a shirt, tie, and slacks. Ladies shall be in a skirt and nice top.

6 - You are lucky. You escape punishment[/SPOILER]

4 - Bent over your bed (or chair, table, desk, etc)

1 - Place a small amount of lube on one finger and slowly spread it around and inside of your anus. Repeat this five times.

4 - Use two fingers roughly for 3 minutes.

4 - Face-fuck yourself. Hold your head still and press the dildo into your mouth. Start slow and work your way up to deepthroating it. This will happen for two minutes

6 - You are most unlucky. Press the tip against your anus and moan aloud "please, no..." then slowly, inch by inch, completely impale your ass. Wait 10 seconds and them completely remove it. Repeat 10 times.

5 - All the way in, half way out. 3 minutes at 50 bpm

3 - Half way in, all the way out (remove it), 50 bpm, 3 minutes (hands and knees)

1 - Insert 1 ice cube until it melts

2 - All of the way in, most of the way out, 50 bpm, 3 minutes (bend over bed)

2 - Insert the dildo completely, sit down on it. Now, use a spanking instrument (spatula, hairbrush, etc). and spank each nipple for one minute. It should be moderate strength and at 69 bpm.

2 - Insert the dildo completely and edge yourself once

3 - Insert it completely and leave it there. Twist at 126 bpm, two minutes.

4 - All of the way in, most of the way out, 58 bpm, 3 minutes (standing)

3 - Insert the dildo completely and spank your ass hard for two minutes. 52 bpm. Each spank should hurt and curl your toes. Clean it off.

6 - Unlucky. All of the way in, most of the way out. 100 bpm, 4 minutes.Phase

3 - Fuck yourself with the dildo, All of the way in, most of the way out, 92 bpm. Orgasm. (on back)

Although it was intense, i really enjoyed it. i shall probably be doing it again. :)

I am going to give this a go later does anybody want to roll for me

Rolling for lancssubslave :p Have FUN!!!

Phase 1: Dress
5 - Completely naked

Phase 2: Introductory punishment
1 - Stand in the corner for five minutes

Positions:
3 - On your back with your knees pulled up you your chest

Phase 3: Preparation
4 - Coat one finger in lubrication and quickly shove it into your anus. Repeat this five times.

Phase 4: Stretching
6 - You appreciation was not sincere enough. You are not allowed to stretch yourself with your fingers.

Phase 5: Your dildo
5 - Rough face-fucking. Immediately insert it as deeply as you can. Gag yourself on it. Take it out and slap your face with it. Pretend that the dildo is a real cock that wants to use your mouth abusively. Two minutes.

Phase 6: It begins
6 - You are most unlucky. Press the tip against your anus and moan aloud "please, no..." then slowly, inch by inch, completely impale your ass. Wait 10 seconds and them completely remove it. Repeat 10 times.

Phase 7: Fucking
6 - Unlucky. All the way in, most of the way out 56 bpm, 3 minutes

Phase 8: More
6 - Unlucky. All of the way in, most of the way out. 69 bpm, 3 minutes.

Phase 9: Cool off your ass for a bit
4 - Insert 4 ice cubes until they melt

Phase 10: Back to the dildo
4 - All of the way in, most of the way out, 58 bpm, 3 minutes

Phase 11: Punishment
4 - Insert the dildo completely, sit down on it. Now, use a spanking instrument (spatula, hairbrush, etc). and spank your genitals, but focused. Men should only swat their cockhead, ladies, spread your vulva and swat your clitoris. It should be moderate strength and at 69 bpm.

Phase 12: Pleasure
5 - Slowly, ever so slowly pleasure yourself for five minutes. Do not orgasm.

Phase 13: Drilling
3 - Insert it completely and leave it there. Twist at 126 bpm, two minutes.

Phase 14: Are you sore yet?
5 - All of the way in, half way out, 69 bpm, 3 minutes

Phase 15: More pain
1 - Coat you cock or vulva (be sure to get the head or clit) with toothpaste. Stand in the corner without touching yourself for two minutes. Afterward, clean it off.

Phase 16: More fucking
3 - Half way in, all the way out (remove it), 80 bpm, 4 minutes

Phase 17: The end
1 - Insert the dildo completely and bring yourself to orgasm however you choose.