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I grabbed it from the box under my bed and set it on the chair behind her. I grabbed her shoulders and led her backwards to the chair and told her to ...it down. She asked me why and I told her it was a surprise and as she started to sit down, her asshole hit the tip of the plug. She gave out an "oooh" and started sitting lower and pushing down harder. She was almost past the widest part when she told me "I don't think I can get it in on my own. Will you help me?" In which I grabbed her shoulders. I knew he spanked me a lot and noticed that my ass was a dark red when I was changing but did not realize how many days that my ass would be sore after that spanking.I had a female boss at where I worked at that time that called me into her office a couple days after I had the spanking and she told me to sit and I told her I would prefer to stand but she insisted on me sitting. Now keep in mind the boss and I were friends but did not know that I liked getting spanked. So after she insisted that. More

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