Yesterday:

I was ordered to go out in public with the biggest plug possible.  I warmed myself up for about forty-five minutes fucking myself with all of my toys, including my 3.5 inch diameter dildo (picture below).  I also pumped my hole for a while, trying to make my hole as fucked up and destroyed as possible.  Unfortunately, I had an accident I was getting dressed to leave with it in, and wasn't able to fulfill your orders.  

Today:

As punishment on myself, I destroyed my ass when my ass was still sore from yesterdays hardcore stretching.  I went extra hard on myself today, including fucking my huge dildo very hard and fast, and letting it sit and stretch me out for a while, which was hard to do, but I knew I deserved it.  I fucked myself good today, and I'm hoping my ass will be clean tomorrow for another day of anal fucking, and hopefully to go out in public.  I have many more pictures if mistress would want them.

very cool thread!

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Dear Mistress
I have found a store that sells POM, but only the big bottles. I've tried putting it in my bum in private but it is far to big and hard even for my greedy hole. I even tried empting it and part filling with water but it still won't fit. I have one last thing to try. I have some soft silicone so I'll use the bottle as a mold to make a dildo.

This will put me over your 14 day deadline so I might have to take your punishment after all.

Best Regards, your obedient slave 

So i was all plugged up waiting to go to bed.  Maybe it was the abrupt design or the nature in which I inserted it, but it was feeling like I had a walnut stuck in my ass.  I decided to sit on it at the computer and try and relax.  I avoided the usual hadrcore porn and viewed my favorite live webcam girl.  She just sits at the computer, drinks her coffee and dances around a little bit but she is so unbelievably hot that it is beyond sexy.  The internet feed was weak so every now and then it would freeze while she was shaking her ass, which was just fine with me.  I mean this girl is just beyond perfect.  Beautiful perfect and perky B cup boobies.  Although she was relaxing my eyes, my ass was still protesting the plug wedged inside.  It strained my walls and pushed hard on the inside of my sphincter gripping the base.  I kept thinking once I got used to it I would be able to sleep soundly but that feeling never came.  After nearly three hours I decided my hole had had enough punishment and there was no way I could sleep stuffed tonight.  Usually removing a toy makes me sad but tonight it was a relief.  My ass still ached like I'd had a walnut stuck in it.  I finally went to sleep with my smarting butthole reminding me of my punishment, which proved to be effective if not fully carried out.  If I had done what I was told earlier in the week, I wouldn't be sore now.  In that way, my mission was accomplished.

ah, my home circumstances wouldn't permit it, so i'll masturbate from the sidelines. for now!

Yes Mistress, I'm sorry Mistress.  I used my smallest plug but it just wouldn't settle.  But I think the 3 hours of craziness is just as good as 8 hours unconcious.  I did sleep with it once a while ago, but that was after an all day ass banging session so my hole was quite comfortable by bed time.  I couldn't really do any prep for this so I couldn't ease into it.  I'll try better next time.  I really felt like an average nonassplaying person who somehow got a walnut stuck up their ass.