She liked an idea I had that was inspired by something she had me do years ago when I was her houseboy. I had lots of chores as her houseboy, including checking her Post Office box when she was expecting a gift from a distant slave. She couldn't be bothered to waste her valuable time at the post office. It's too bad I can't do this for her anymore, since I am now a long distance slave myself. The inspiration for my punishment was the time she had me put the key to the PO box in a condom, and insert it in my ass, leaving the condom hanging out so I could retrieve the key. Luckily a key isn't very big, but she still found it amusing.
So I offered to write out "I will follow Mistress Madeline's rules" 100 times, fold it up, put it in a small container, put that in a condom, and put it in my ass for as long as she wanted. Writing that out gave me time to really think about how bad I had been. I am supposed to follow her rules. What's the point of being a slave if I don't? I was tired of disappointing her, and this was a reminder, 100 times, to do better. My purpose is to amuse her and to serve her, not to be a nuisance that can't follow orders. I will follow Mistress Madeline's rules. I WILL follow Mistress Madeline's rules.
So I folded the paper, seen here, and tried to put it into the small container I had. But I hadn't anticipated how big the folded paper would be. It wasn't going to fit in the small container, so I decided to just put the paper in the condom and stick that in my ass. I folded it as small as I could, and put some lotion on it for lube, but I had a little trouble getting it in. I finally got it inserted, leaving most of the condom out so I could grab it and pull the paper out later, and attempted to get some work done. Sitting with this paper in my ass was very distracting. It was impossible to get anything done. I could only think of my Mistress, which was the point.
After about forty minutes the phone rang. I had somewhere to be later that afternoon, but plans had changed and had to leave now. The problem was that Mistress told me to keep the paper in my ass for an hour. I couldn't stall my appointment, so I had to leave with it still in my ass.
Twenty minutes later I was about halfway to my destination, but since the hour was up I decided to take the paper out. Otherwise I would have to leave it in for a lot longer once I got to my destination. So I stopped in a fast food restroom stall and tried to get it out of my ass.....tried is the key word. In the last hour the paper had moved pretty far up my ass. The condom was still sticking out, but barely. There wasn't much to grab onto. When I did pull on it, the paper didn't budge. The condom was really stretching but nothing was coming out. It felt like the condom was going to break. What happened was the paper had unfolded some while it was in my ass, and wasn't going to come out as easily as it went it. I kept pulling on the condom, but it kept stretching and stretching. The paper was not moving.
At this point I started to panic. This was taking too long. I had an appointment to get to. But even worse was the fear that the condom was going to break and the paper would be stuck in my ass. I thought I was going to become a funny story for an ER nurse to tell her friends....the dumbass with paper stuck in his butt. I was freaking out.
I kept pulling, and pushing, and moaning in pain, and eventually it started to move. I am pretty sure other people came into the bathroom while I was in the stall making a lot of noise, but I didn't care. All I could think about was getting that paper out of my ass.
Eventually I got it out, and after washing my hands I rushed off to my appointment with a sore asshole. I think after all that I have definitely learned my lesson....I will follow Mistress Madeline's rules.
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