Thanks for the additions so far! I've summarized all the dares/tasks/rules given here, on GetDare, via PM and through Kik. It's become quite a nice list, so I combined and changed some tasks to make everything hard but still doable. This is my planning for now:
General rules
- I must wear a buttplug 24x7, can only be removed when I have to fuck my ass/use the toilet/do an enema. Must also be worn outside the house!
- Start each day with enema's until my ass is 100% clean. No more cleaning my ass after that, so A2M might get a bit messy later in the day.
- The only clothes allowed are female clothes belonging to the owner of the house. If I go outside I can wear my own clothes, but must wear her panties and a bra underneath, and a button-down shirt. If I'm traveling more than 10 minutes I have to unbutton the shirt. Punishment for buttoning up is 20 spanks for every time.
- Wear a ball stretcher and gag while awake. Can remove the gag to eat/when going outside, except on Friday.
- I must wear nipple clamps at least 30 minutes of every hour I'm awake. The choice of clamps is up to me, except when eating/drinking. Every time I want to eat or drink I must apply the pumps to my nipples and leave those on for 2 minutes. Then I have to attach the clover clamps and roll a single die. That is the combined amount of weights to attach to the clamps, which must stay on until I finished eating/drinking.
- All days except Friday I'm only allowed to eat and drink from a bowl on the floor like a dog, and I must crawl around instead of walking.
- I have to place a dildo in every room of the house. Every day except Friday, when I enter that room I have to remove my buttplug and fuck myself with that dildo for a full minute, as deep as I can get it in. When I leave the room I have to clean the dildo by trying to deepthroat it 20 times.
- Every two hours I'm awake I have to edge myself with a vibrator.
- I can only use the toilet sitting down, on the brim instead of the seat.
- I'll leave my Kik running 24x7 (@wingman1978), tasks given there take priority over the rules here if they conflict with each other. If I'm unable to finish a task because of that I'll leave it on my todo-list for the next time I'm housesitting/have lots of free time.
Thursday April 28
I'll be dropping off my friends at the airport around noon. I'll try to bring a bag with a button-down shirt, ball stretcher and a bra, and before I pick them up I'll put on female panties and a buttplug. I'll change into the button-down shirt and bra in a toilet stall at the airport once I've dropped them off and attach the ball stretcher, and then unbutton my shirt so my bra is showing on the drive back home since that will take way more than 10 minutes.
Once at their house I'll do some enema's to clean out my ass and start to comply with the other rules (gag in, clamps on, replace my own bra and panties for hers and put on one of her dresses, and place dildo's in every room). After that I'll do AlwaysLucky's dare: I'll crawl around the house to find a nice pair of her boots, pick it up with my teeth and carry it to the middle of a large room. Then I'll kiss it all over and thank it for allowing me to cum. I'll bind my hands behind my back and try to cum by humping and straddling the boot without using my hands, wearing just her panties and a bra.
For dinner I'll do the Candlelight Dinner ordered by JarOfAce: I'll prepare dinner, then get on my back against a wall. Then I'll put my legs over my head so my asshole is facing straight up. I'll remove my buttplug and insert a candle coated in hot sauce into my hole. After lighting the candle I'll coat my cock and balls in toothpaste. Then I'll eat my dinner like that, while stroking my cock. If I can eat my entire dinner without edging/having to stop stroking I can cum and eat my cum as a dessert. If I didn't I have to bust my balls 50 times, then ruin an orgasm into a cup of pee. That drink will be my dessert instead.
Finally after dinner I have an e-stim dare from HappyDares. Since I'm already ordered to wear nipple clamps half of the time I'll make this a bit harder by pumping my nipples and applying a drop of hot sauce to them beforehand to make them more sensitive:
I want you to get your E-Stim on your cock and set it on level 5. Wait until you reach the first edge and turn it of. Now add one clamp to one of your nipples.
Next round: set the stim one level higher until you edge. Turn it off and add a clamp to your other nipple.
3rd round. One level higher to the edge and tie up your balls after that.
Keep going until you edged once on every level. Now that your nipples and balls are busy start working with your butt for every edge. 1st small plug in until next edge, then medium plug until next edge then big plug. If you have to keep going after that: keep the big plug in for the next edge and then take a little break. Start fucking your ass with a small dildo for 3 minutes, then medium, then large. If you are still not done keep using the medium dildo while edging for the next levels until you reached the last one. Now you can cum however you want.
Once that's done I expect that I'll be completely wasted, so I'll write up my reports for that day and head to bed.
Friday April 29
This is the "long dare day". I'll try to complete the following ones:
1.
This full-day pee dare. I'll start the day by filling a large bottle with water. This bottle is the only thing I can drink from, and the only way to re-fill it is by peeing into it. That will get me started with drinking just water, progressing to stronger and stronger piss throughout the day.
2. The gag for today is the one with the feeding hole. Anything I eat or drink will have to go through this, so solid food will go in the blender first, as suggested by DareFiend.
3. Anal stretching ring task from DoeEyedGoddess:
From the moment you get up put on the medium stretching ring and harness. Wear it from sunrise to sunset. Every half hour, so :30 and :00 attempt to put in the largest stretching ring. If unable give yourself 30 swats on each cheek with the paint stirrer.Then put on the Clover clamps and do 20 jumping jacks.
If able to insert the largest one then keep it in until you have cum 3 times using the Hitachi Magic Wand on the medium setting while wearing your spring clamps.
If unable to get the larger plug in by sunset, Cover your balls in icy/hot and edge 5 times before cumming.
Saturday April 30
This day is reserved for punishments so far, and if the votes on my
spanking poll don't change I'll spend the last 8 hours of this day creating a thread on GetDare requesting spanks. The full rules for the thread will depend on how my previous days went; the worse I do the more spanks everyone will be able to give me.
I'll probably need to do some shopping for groceries too, which according to my rules will be done wearing his GF's panties and bra underneath my clothes. If Thursday and Friday's dares go really bad one of the pre-assigned punishments is to do
this ass smoothie after my morning's enema's, and keep that in while shopping, then expel into my dog bowl and lap it up. I'll do my very best to prevent that
Sunday April 31
I'll probably sleep until late in the morning to recover a bit, and then clean the house and pick my friends up at the airport late in the afternoon. Afterwards we'll have dinner and I'll head back home.
Other dares!
I doubt I'll be bored
But if you have additions to this list feel free. I'm thinking of these areas in particular:
- Something to spice up the trip from the airport to their house (about 90 minutes) might be fun.
- Additionally small tasks to do on Friday between trying to fit my large stretching ring every half our and edging every two hours would be welcome
- Additional punishments for failure on one of my tasks. Make them really harsh and do request a form of proof so I'm properly motivated not to have to do these!
- Finally, any way to make cleaning their house more interesting/challenging is nice too.
