21 pig requesting humiliation

[whoisit]

for this dare you only lube will be toothpaste. Plug yourself with your small plug and apply tooth paste on all your sensitive parts. Change to your medium plug and do a squeaky clean wedgie. To end you must put your large plug an edge with toothpaste. when almost cumming masturbate with an ice, you may only stop if you cum or it melts. If you are unable to cum, no orgasm for you today. Only then you may remove your plug

[DiffidentDifference]

His excellency redcamel has great ideas there - you'll continue to parade naked in front of a mirror masturbating with the dildo in your hand, teasing your clit with its base as if you were a man stroking his cock; but you'll now step that up by looking yourself in the eye and telling yourself out loud* that you do this because strangers on the internet told you to, and you're a filthy pig who's turned on by it.

Anytime asshole is plugged (which should by now be frequently & often) you'll thank your plugs for their time in you; each time you put them in, take them out, or re-lube them.

(*If it's not safe to be actively vocal, then you'll say it innternally - but you must think it in fully formed actual words & sentences.)

[filthypig]

I continued my pattern of daily walks with my large buttplug today. Thanks to my new dare from DiffidentDifference I gave my buttplug a small kiss and said “Thank you for filling my ass”. I’m not quite sure if this is what you wanted me to do, but I was humiliated doing it. Thank you sir.
I stepped outside for my usual walk through a park. The weather is especially nice which meant lots of people out and enjoying it, I was especially aware of the plug invading my asshole as I walked past everyone. When I got back to my own room I immediately stripped nude. I was going to just masturbate but figured I may as well finally try double penetration just to prove it is impossible...
I grabbed my dildo and plenty of lube as I lay down. I pushed the large plug out of me, and thanked it for being in my ass. I then used the dildo to loosen myself up and relax more. Once I had the dildo in me fully I tried to push in the plug but the small tip felt sharp against my sphincter. I swapped and inserted the plug again. I pushed it out just enough that I could lign up the dildo with the small stem above the crystal. I pushed the dildo and, to my shock, it went in. I kept pushing and moving and it slid inside me, the large buttplug and my dildo side by side in my asshole. I was shocked and have never felt so stuffed in my life... As I moved the toys around and fucked myself I felt myself stretch so far. I’m a bit ashamed of how loose my ass was but I managed to fit the dildo balls deep next to my plug.
Thank you very much master RedCamel for instructing me to try double penetration. This pig has been opened up and stuffed properly sir. I may have to pause on anal tasks for a day to recover from this!

[DiffidentDifference]

Originally Posted by filthypig

Thanks to my new dare from DiffidentDifference I gave my buttplug a small kiss and said “Thank you for filling my ass”. I’m not quite sure if this is what you wanted me to do, but I was humiliated doing it. Thank you sir.

Yup, that's the right idea. You want humiliation - you have to be subservient to an inanimate metal blob you stuff up your asshole.

It's time for you to look your reflection in the eye as you masturbate now, though.

(Also, not a "sir"; gender neutral terms & pronouns in use please. I appreciate there's not many great options outside the binary, but "Your Excellency" is kind of pleasing.)

[filthypig]

Yes your excellency, sorry about that.
Today I did another public walk with my plug in. I thanked my plug and gave it a sensual kiss and lick before lubing and inserting it. I was going to wear a medium plug after the abuse my hole suffered yesterday but wanted to be a good pig and forced in the large plug. I’ve become much more accustomed to being a plugged toy in public but today I had a new humiliation, some lube leaked out of my hole into my undies giving me a wet sticky spot...
After I finished my 20 minutes I went to my room and stripped nude. I held the dildo on my clit and jerked myself off, looking into my eyes as I whispered “I’m doing this because strangers on the internet told me to, and I’m a filthy pig who gets off on this”. As the pleasure heightened I was struggling to keep my eyes open to look at myself, squinting in pleasure. It took me a while because I was actually too wet to get any friction from the dildo but I eventually came in my mirror. Thank you for the tasks and for making me humiliate myself to an orgasm.

[redcamel]

Well pig, what I was meaning with "double penetration" wasn't two toys in ass, but one in ass one in cunt. This because you said you're trying to become anal only, not that you already are anal only (well, since the hole is there, isn't it enough degrading using it when you're said to?). Anyway it's great what you did, and I'm glad I pushed you beyond what you thought was your limits (even if unintentionally).

Thanks to DifferentDifference to have made you masturbate in front of the mirror staring into your eyes, I would have asked you the same.

Do you think you could make a walk with your dildo inserted instead of the plug? Maybe it's easier to slide in, but probably a lot more uncomfortable to have it in while walking... Try at home before going out.

[filthypig]

Originally Posted by redcamel

Well pig, what I was meaning with "double penetration" wasn't two toys in ass, but one in ass one in cunt. This because you said you're trying to become anal only, not that you already are anal only (well, since the hole is there, isn't it enough degrading using it when you're said to?). Anyway it's great what you did, and I'm glad I pushed you beyond what you thought was your limits (even if unintentionally).

Thanks to DifferentDifference to have made you masturbate in front of the mirror staring into your eyes, I would have asked you the same.

Do you think you could make a walk with your dildo inserted instead of the plug? Maybe it's easier to slide in, but probably a lot more uncomfortable to have it in while walking... Try at home before going out.

Yes sir, I’m sorry for being such a stupid pig. Would you like me to do the task again filling both my holes sir? I really felt so good fucking my asshole with a plug and dildo sir it was so arousing.

I bought my dildo because it had been advertised as a buttplug. But when it doesn’t have a taper just the suction at the end, and when it’s lubed it just slides out of me. I found this out the hard way when I was told to walk with this dildo in and I felt it slide out of me with every step. I felt the suction base rubbing against my pants as I tried to keep going. I sat on a bench to try to discreetly reinsert the dildo. When I walked back I was waiting to cross a street when an older couple came to wait behind me, both men. When I crossed they passed me on the left, both looking at my face before turning to each other and laughing. I have to assume they saw my dildo poking out of my hole into my pants... I was mortified sir. If the wrong person had noticed me wearing a sex toy in public who knows what may have happened.
For a shorter answer: Yes, I have tried wearing my dildo when I walk and it is to public for my likes sir...

[redcamel]

Since you was so good to manage a double anal insertion, let's leave your cunt alone for now and save its use for more degrading purposes.

About the two men you met during your dildo walk, well, are you sure that they laughed because they saw the base poking into your pants or simply they saw what they thought a gay male walking in a strange way?

You say it's too public, but you forget I said you to try it at home before, isn't it? So now you'll make another test at home: keep your dildo inserted and do a crotchrope to keep it in place. The crotchrope will have a knot on your clit, to make it more interesting, wear and forget about it, go on with your normal life as long as you can and see how it works while making the normal movements of walking, sitting, bending etc. Do it only at home, for now, I'll say you if I want you try it in public again.

I anticipate that when the experiment with dildo and crotchrope will be finished, you'll have a no stretching time, a week or two, when you will use only the small plug. Now you're conscious of the stretching skills of your ass, but I don't want you risk to loosen it too much, it has to be trained but at the same time tight enough to satisfy the real cock(s) that will take possess of it.

[Sir Cap]

Considering scat is in your likes, I propose that you will no longer rinse your plugs and you will always lick them clean. If necessary you will brush your teeth after.

[filthypig]

Originally Posted by redcamel

Since you was so good to manage a double anal insertion, let's leave your cunt alone for now and save its use for more degrading purposes.

About the two men you met during your dildo walk, well, are you sure that they laughed because they saw the base poking into your pants or simply they saw what they thought a gay male walking in a strange way?

You say it's too public, but you forget I said you to try it at home before, isn't it? So now you'll make another test at home: keep your dildo inserted and do a crotchrope to keep it in place. The crotchrope will have a knot on your clit, to make it more interesting, wear and forget about it, go on with your normal life as long as you can and see how it works while making the normal movements of walking, sitting, bending etc. Do it only at home, for now, I'll say you if I want you try it in public again.

I anticipate that when the experiment with dildo and crotchrope will be finished, you'll have a no stretching time, a week or two, when you will use only the small plug. Now you're conscious of the stretching skills of your ass, but I don't want you risk to loosen it too much, it has to be trained but at the same time tight enough to satisfy the real cock(s) that will take possess of it.

Yes sir thank you for sparing my pussy sir.

I think it was both reasons sir. Getting back to my room I checked in the mirror and saw the circle of the dildo base poking into my pants sir. If they noticed my walking strange it would be because of that...

Yes sir thank you sir. I will have to purchase some rope for this task but will take it on soon sir thank you.

And yes sir thank you sir for keeping my hole tight. I want to be a good toy to use I love stretching myself but I fear loosing my tightness before I can service a cock. Thank you sir.

Originally Posted by Sir Cap

Considering scat is in your likes, I propose that you will no longer rinse your plugs and you will always lick them clean. If necessary you will brush your teeth after.

Yes sir thank you for the task sir. I will admit I lick the plug most times but being forced to lick it no matter what the plug comes out like will be very degrading thank you sir.

[filthypig]

Originally Posted by whoisit

for this dare you only lube will be toothpaste. Plug yourself with your small plug and apply tooth paste on all your sensitive parts. Change to your medium plug and do a squeaky clean wedgie. To end you must put your large plug an edge with toothpaste. when almost cumming masturbate with an ice, you may only stop if you cum or it melts. If you are unable to cum, no orgasm for you today. Only then you may remove your plug

Thank you for the task sir. I’m sorry it took me a while, this pig doesn’t like toothpaste and tried to avoid it. But I need to be grateful and complete all tasks given to me so thank you sir.

I stripped naked and lay out my plugs and my toothpaste. I lubed up my smallest one and grimaced as it was completely coated in minty toothpaste. I slipped it in and surprisingly it didn’t feel to bad. I then smeared toothpaste on my nipples, clit, and pussy lips. My nipples tingled a little, but the pain and burning between my legs started immediately. I pushed out my small plug and thanked it before inserting my medium one. I put on a pair of dirty underwear and began pulling my underwear front and back giving myself a big wedgie. The wedgie forced more toothpaste into my cunt and the pain became so unbearable. I’m sorry sir but I gave up here as the pain was to much for the pig to continue.

Please, I need a punishment for failing your task sir. Please punish this stupid pig.