I wondered if going deeper was the key to having an anal orgasm. The closest object to my two fingers I had was a large sized novelty tooth brush that...had a hard plastic handle. The handle was about a foot in length, so I figured that solved the depth issue. I lubed it up with spit and slowly slid it in. It was very interesting, like taking a shit in reverse, but not quite. You know that absolute relief feeling you get when the shit comes out? It was that as I slid it out, then a filling. I entered my office took the file and was almost out when I heard a faint noise that caught my attention… I stopped frozen and looked around, then I heard another noise, It was distinctly the moan of a woman having sex and it came from the adjacent office which belonged to my boss! My heart sped up. The guy was known to be a player but I never expected to find him red handed with a girl on his office. I knew it was wrong… but we shared a bathroom so I decided to take a closer look. It took me. More

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