This is a series of stories explaining how I met my Master, what I do to please him, and how he punishes me when I am bad.
This story describes the first time my Master used my ass. We had experimented a little previously. One time we had been on a business trip for a conference. Back at the hotel my Master and I had been laying on the bed and I had my back to him. I was grabbing and squeezing his cock and he slipped the tip in my ass while I kept squeezing him until he came. But that was just playing. This time my Master made clear he expected full access to use my ass as he wanted.
In preparation for the upcoming trip, my Master told me to order a butt plug. I was excited buying my new toy. I ordered a dark blue, slightly curved plug, that had a ring at the end for my Master to put his finger in to push, pull, or turn the plug. I also bought plenty of lubricant.
We got to the hotel before dinner and went to my Master's room. He took off all my clothes and told me to go get my toy. I went and got the butt plug and lubricant and handed them to my Master. He laid back on the bed and said "I want you to unzip my pants and pull out my cock. Get on your knees and suck me, but turn your ass around this way so I can play with you."
I did as he instructed. I got on my knees and put his cock in my mouth. While I sucked him and licked him, he put some of the lubricant on my toy. He then pushed it up to my opening. The lubricant felt cool and slick on my ass. He slowly started to push the plug in. It hurt at first, and made me catch my breath. But then he got past the tightest point and it slid right in.
I felt full and slightly ashamed, having the plug in my ass. While I licked and sucked my Master's cock he kept pushing and pulling the plug. It had one very wide spot, and when my Master pulled that out, I gasped and cried out. Then he shoved it right back in. This went on for a while, until eventually my Master decided to come in my mouth. He pushed my head down onto his cock, while he pushed the plug deep into my ass. I swallowed all of his come.
Then my Master said he was hungry, it was time for dinner. He got dressed and told me to put back on the work suit and skirt I was wearing earlier. He said, "I don't want you wearing any panties. I want you to keep in that butt plug. I want to go down to the nice hotel restaurant knowing you are completely mine, completely subservient to me."
I begged him to at least let me put on panties, I was so afraid the plug would fall out. But he said no.
We went to dinner and I felt so uncomfortable the whole time. My Master loves that, he loves making me squirm. Every time the waiter came by, I felt self conscious. Dinner seemed to last a long time. My Master was happy though, he enjoyed me feeling embarrassed. We finally went upstairs and I was about to follow my Master into his room. "Wait," he said, "you weren't good enough at dinner. I'm not letting you into my room until you show me how good you can be." Then he closed the door.
I knew what my Master wanted. I was sure he was watching through the keyhole. I looked around and hoped no one was coming. Then I started to take off my clothes. My jacket was easy, it wouldn't matter if someone saw me without that. Then I unbuttoned my shirt. I was scared, but I took it off. Then I took off my bra.
I knocked on the door then, hoping my Master would let me in. I got no response, so I realized I'd have to take off my skirt too. I kept looking back and forth down the long hall, praying no one would come. I finally unzipped my skirt. I stood there, in front of the door, standing up straight and not covering myself at all. My breasts were uncovered, and anyone who came by would see the plug in my ass. Finally, after what seemed like an eternity, my Master opened up and let me in.
Now was the time I'd been nervous about all night. I knew my Master wanted to use my ass. He told me to take out the plug, so I took it out and put it in the bathroom sink to wash it off. My ass felt strange and empty now without the plug. Then I went back to the bedroom. My Master told me to bend over and put my hands on the bed. My Master was rock hard by this time. He put lubricant on his cock and pushed it against my ass, which was still tight despite the plug. He slowly pushed it in. I felt the fullness as he entered past my tight muscle. It is hard to describe, it felt like a burning sensation, like when you stretch a muscle too far. I begged him to stop for a second. I started to stand up.
My Master pulled out, so I could rest a minute. After I caught my breath, he started pushing right back in. He pushed my face back down, by gently pressing on my back. "Shhh, relax my pet. I am going to do this and you will be fine. Just relax and open yourself to me. I am not leaving you again until I come."