Several days after that first play time, Henry and I met for coffee again. It didn't take him long to ask if I'd like to play again. When I agreed, he invited me to his home, if I was comfortable with coming there. By that time I was feeling OK about it, and I agreed.
Henry suggested we do another role play, this time using an office setting. He explained that he has a large home office with a large desk and sitting area that would provide a good setting. He also suggested that I be his boss who has discovered that he has a large amount of pornography on his work computer and has been masturbating in his office. Finally, she said that I could bring whatever toys and implements I'd like, but that he has a large collection from which I can pick things to use on him. It was at this time that I began to realize how deeply Henry was involved with spanking and kinky sexual activities.
When I arrived at Henry's home on the designated evening, we first sat in his sun room and had a cup of tea. I think he was trying to make sure I was comfortable being in his home. He then took me to his home office, which is located in the basement. He explained that the basement was designed as an in-law's apartment and contains a living area (which is now his office with a sitting area as part of it), a bedroom with attached bathroom and a small kitchenette.
I suggested that the setting for the role play be that I have called Henry into my office to discuss a serious matter. He would arrive, not knowing what issue was to be discussed. He was agreeable to this plan. I then asked him to show me where the pornography is located on his computer and where he keeps his spanking toys. After he dis so, I then asked Henry to leave the room and return in 15 minutes for his appointment with me. I thought that would give me sufficient time to review the type of pornography contained on his computer and make some decisions about spanking implements. Before he left, Henry shared with me that I could spank him harder than what I previously did. He told me that he actually enjoys quite a hard spanking. I thanked him for sharing that. I then asked him how he felt about being completely submissive to a woman. He provided the answer that I expected, which confirmed my preliminary plan to step things up a bit during this play time with Henry. My brief review of the porn folders on his PC also confirmed the extent of his kinky interests, especially spanking.
When Henry returned, I put on my stern and serious face and directed him to take a seat in the chair to the side of my desk. I then calmly, but sternly advised him that our IT office had discovered a serious amount of pornography on his computer and a history of him visiting pornographic websites while he was working. He first tried to deny everything, but quickly realized it wasn't working. I then told him that we have security cameras in everyone's office and asked him if he had been doing anything in his office that he wouldn't want anyone to see. He played the role quite well. He stammered and hemmed and hawed and eventually said "no". But he then asked why I brought that up. I just said "I think you know" and added that it was interesting to watch a man masturbate.
I then suggested to Henry that we needed to talk seriously about his situation. I explained that I should fire him. I quickly added that I really didn't want to do that because he was such a productive employee. I also added that I was willing to find an alternative solution. He was very open to that, so I explained that I also enjoy the kinky sexual aspects of life. I offered that, based upon the porn on his computer, he would like to be spanked by a woman. I suggested that I would not fire him if he was willing to submit to corporal punishment from me for this situation and any future work related performance issues. Henry quickly agreed.
I then informed Henry that I would start out with a prolonged spanking and asked him to tell me his favorite position. Since he had a folder labeled "spanking positions" on his PC, I suggested that he show me his favorite. This is what he selected. He then showed me a video of the same gentleman being spanked in this position. It was quite interesting. He bottom was thoroughly spanked, but so was the head of his penis and the tender areas around his anus and lower bottom. It was quite a spanking.
After making Henry strip, I placed him in this very position and thoroughly spanked him in the same way. I was amazed to see that he remained hard through out the entire spanking. That made me decide to give him a very hard spanking with an implement. I suggested that he provide me with his favorite spanking implement. I was a bit surprised when asked me to use a leather sandal that I was wearing (this was back in warmer weather). I quickly agreed. After turning him back over my knee, I proceeded to apply the heavy soled sandal quite vigorously to his bottom. This time his erection disappeared and he did a lot of squirming and begging me to stop.
We eventually retreated back to his sunroom for a glass of wine, which gave us time to discuss what had taken place and our budding relationship. We each agreed that we would like to continue. However, I suggested that our next play time should be a bit different. I shared with Henry that it should not be a role play, but something real. And I added that it should be completely controlled by me. (I wanted to see just how far he was willing to go with giving me control). Henry quickly agreed and we decided that I would get in touch with him when I had made some plans.
If Susan wants me to do so, I'll continue to share how our relationship developed.