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Requesting Looking for tasks to challenge me on my free weekend

jay_hom21

Active member
Joined
Jan 26, 2026
Gender
Male
Pride
Bisexual Bisexual
Heyy everyone. I've managed to get a mostly free weekend (and Monday) which I don't get often and I'm looking to push myself with some kinks I already have as well as maybe trying out some new ones to push myself a bit more and to build up my confidence doing some more difficult tasks.

Please could I have some creative tasks to complete that will challenge me and I will give a full, detailed report for all of them once I have done them. In these tasks you may use anything listed in my likes or dislikes and you can also give me a punishment to do if I am unable to complete the task you have set for me.
Unfortunately I don't have any toys at the moment so I won't be able to do tasks involving them but I can try to improvise in places with regular household objects (like using clothespins as nipple clamps).
For the duration of this, until Monday night, I will not be allowed to cum so please try to avoid this in your tasks. However if you would like to decide the way I cum once I have finished then you can and I will make sure to follow this.

I don't currently live alone but the people I live with will be out a lot over the weekend and will be out all of Monday. I can still do some things while they're in but I may delay completing some tasks until I am alone so that I can complete them properly and without fear of being interrupted. I will make sure to have completed them all by Monday night though.

If you see this thread after I have finished and you want to give me a task then please feel free to add one and I will complete it and give a full report as soon as possible.
If there is something that I haven't listed anywhere in my likes/dislikes/limits that you would like to do a task based on then please send me a message and I will let you know what it is and I'll update that page.
 
Since you like pet play, you could just do a simple on all fours, if possible in front of a mirror.

Take one rubberband, the ones that almost anyone has in their kitchen, and few clothing-clips/clamps. Please test first that its not sharp and try somewhere on your skin if the clip is too hard. If too hard make it lighter especially if its your first time.

Get on your knees, naked, dick on the floor, in front of a mirror, just to see yourself desperate and start first with putting a clothing-clip on your tongue and keep the tongue out until it feels uncomfortable. The drool that comes out should drip on your chest.

Then take the rubberband, stretch it on two fingers on one hand and hold it like that over your nipple. Now pull the upper side of the rubber band with your other hand and whip your nipple with it. Test the strength a bit and see what you like more. Try this on both nipples.

After few Minutes take the clamp from your tongue off, put one on each nipple and get on all fours and observe yourself like that in the mirror as a puppy for few minutes.

You could also hump a pillow while being like that. Have fun 🙂
 
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Thank you for the task :)

I luckily have quite a big mirror in my room so I started off by going there, getting naked and getting on my knees with my dick resting on the floor (pretty uncomfortable but I stuck with it lol).
I then got my clip and placed it on my tongue (i've used them a couple times before for similar things so I know they're not too sharp) and I sat in front of my mirror for probably about 8 minutes which was when it started to become pretty uncomfortable. I had quite a bit of drool on me at this point which was quite humiliating to look at and feel.
I then got my rubber band and started to whip my nipples with it. I struggled for a bit to get the whip to be strong enough but I figured out how to do it and I must admit I did enjoy the whipping sensation, even if it did hurt quite a bit. I did this for a couple more minutes and at this point I had a lot of drool on me and my tongue was starting to feel really uncomfortable so I decided to take the clip off my tongue. The clamp was covered in drool when I took it off.
After taking it off I put it on one of my nipples and I got another clamp to put on my other nipple. I sat there for a few minutes like this, looking at myself thinking how pathetic I am while I was humping my pillow. One of the most painful bits of the task was when I took the clips off my nipples, I don't know why but taking them off really hurts (I did quite like it though).

The task made me feel humiliated as well as putting me in a bit of pain which I really enjoyed. I think I'd definitely like to explore pet play a bit more and do some more similar things to this at some point. Thank you again for giving me this task and please let me know if there are any more details you would like to know that I haven't included in my report. ;)
 
Thank you for the wonderful update. It makes me happy that you enjoyed it. There are different kinds of styles and what people prefer. But this would be one of my favorite.
 
For the duration of the weekend you may only pee when the minute hand of the clock reads :13 or :14. If you need to pee at any other time you must wait, wet yourself, or drink it.
 
Thank you for the challenge :)
I think I might find it quite difficult at points but I will make sure to stick to it and I'll give you a report at the end of the weekend of how it went and when I ended up having to wait, wet myself or drink it (I think it will probably happen quite a few times lol)
 
To follow up on the pet play one from earlier: Grab a bowl and fill it with water. Put on a collar (improvise using a belt or similar, just make sure it isn't too tight! don't strangle yourself, please!). Get on all fours and lick the water out of the bowl.

Optional extra if privacy allows: Have a treat (think: fruit, chocolate - cereal, if you want to get a little messy) from your bowl in the same way, not using your hands.
 
Thanks for the task!
For the collar I just decided to use a belt but wrapped around me very loosely to reduce the risk of doing any damage (I'll probably try get a collar at some point but I just used to belt for now because I knew I could make it loose enough to be safe). I then got a decent sized bowl and filled it with water. I got down on all fours and started to lick up the water. I also decided to do this in front of my mirror because I loved the humiliation of that earlier.
After a few minutes, I had managed to get a decent amount of the water up (even though a bit ended up spilling) and I decided that I'd try do the same with something else. I filled the same bowl with some granola and yoghurt (which I chose because I knew it would get messy) and then got down in the same position and began licking it up, making sure to keep my hands behind my back. This was so humiliating and really made me feel put in my place which I enjoyed. After a couple minutes I had finished the food and my face and nose were pretty messy from it, making me feel even more humiliated.

Thank you for the task, I loved getting the humiliation from the pet play task again and I think I'm going to spend more time trying out pet play because it's not something I've done loads of before today but I really enjoy how pathetic and submissive it makes me feel.
 
Appreciate the report. Sounds like you liked it.

Try if you can have your meals from that bowl, as much as possible.

And go for walkies! Get naked, put on your collar, get on all fours, grab your underwear with your teeth, and then visit every room of your house. If you see yourself in a mirror, make sure to either bark at or scratch your mirror-self (are you more of a doggo or a catto?). Once you visited all rooms, put your damp underwear back on and wear it as usual.
 
I did like it thank you. Whenever I'm eating alone I'll make sure my meals are all eaten out of the bowl without using my hands.
I've just been around my whole house in my collar with my underwear in my mouth, barking at myself everytime I passed a mirror (i'm definitely more of a doggo). I've now got my underwear back on which I'll keep on as normal for the rest of the day, they're pretty soaked though because I seem to have drooled loads while I had them in my mouth haha. The walk really made me feel put in my place again and I'm loving the humiliation of going up to the mirrors while I do it. ;)
I'll keep you updated on how my meals from the bowl are going, I'll try to do it for as many meals as possible.
 
For the duration of the weekend you may only pee when the minute hand of the clock reads :13 or :14. If you need to pee at any other time you must wait, wet yourself, or drink it.
Yesterday and most of this morning I didn't have too much of a problem, there were a couple times where I had to wait before I could pee but I never let it get that bad that I couldn't wait.
However, a couple hours ago I was really desperate (I had a lot to drink this morning so I really needed to go). I waited until :13 and then went to go to the bathroom, only to find there was someone else in there. It got to :14 and they were still in there and I wasn't able to get in until :16. At this point though I wasn't able to go ofc but I couldn't sit or stand still for how desperate I was. I knew now I had to decide if I was going to wet myself of drink it all.
In the end I decided to wet myself. As humiliating as it was to feel the pee running down my legs through my clothes, I decided that I would rather do this than drink it - because of how desperate I was I knew I'd have so much to drink that I didn't think it was worth it. Afterwards I went and got a shower and changed out of my pee covered clothes.

I'm hoping that I manage to avoid having to pee myself again but sometimes it can be really difficult for me to get in the bathroom and when I'm as desperate as I was earlier I don't have any other choice. Thank you for setting me this task, it's been difficult to stick to but I've really enjoyed it at the same time and I'll keep you updated on how it is going :)
 
Appreciate the report. Sounds like you liked it.

Try if you can have your meals from that bowl, as much as possible.

And go for walkies! Get naked, put on your collar, get on all fours, grab your underwear with your teeth, and then visit every room of your house. If you see yourself in a mirror, make sure to either bark at or scratch your mirror-self (are you more of a doggo or a catto?). Once you visited all rooms, put your damp underwear back on and wear it as usual.
Just thought I'd come back and give an update!
Yesterday I was alone when I was eating my lunch so I decided that I would have that from a bowl. I sat in front of my mirror again and started to eat. This time I was eating some egg and beans on toast. This was so so messy and also quite challenging to eat because I had to have the toast without my hands. It took me around 15 minutes to eat it and my face was covered by the end of it.
Unfortunately I wasn't alone for any of my other meals yesterday but I was this morning for my breakfast so I got in the same position in front of the mirror and repeated the same process with my bowl of cereal. This was again extremely messy and humiliating but not quite as bad as yesterday's lunch haha.
After this I decided to do your task of going for walkies again. This time I spent about 30 minutes doing it, making sure to spend quite a while barking at myself in each mirror. I am now sat in my wet underwear on and I will keep them on for the rest of the day (unless another challenge requires me to take them off in which case I will put them back on once I have finished).
 
thanks for your reports. glad you had some fun doing the meals and the walkies. :)

i'm not sure if you have any more time alone. if so, here's one more request. or well, two actually: don't pee for the next hour. and the next time you pee go into your underwear and then go for walkies one more time.

if you're already finished, feel free to ignore this. :)
 
I do have a bit of alone time this evening so I'll make sure to hold my pee for now and then I'll go for walkies one more time. Thank you for the tasks and helping me explore more things pet play related, I've really enjoyed it 🤭
 
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