Susan has recently suggested that I contribute to her blog to share a bit more about my relationship with Henry. I have never tried to write in a journal or share things about myself, so this is a huge challenge to me. But I thought I could give it a try and see how things go. I realize Susan has shared some things about Henry and me, but I thought it might be best if I start from the beginning.
I have to thank Susan for introducing me the the kinky life she and Barry enjoy. I would have never explored this area if were not for them. And, I would have never met Henry. I met him through a personal ad he placed in FetLife. It was totally unlike me to look or respond to something like this, but I'm very glad I did. Henry is in his early fifties and has never been married. But he has led a very interesting life and has a very kind and gentle spirit about him. He is also very kinky and submissive, which are two traits I have come to appreciate in a man since my husband passed away at too early an age.
I ended up meeting Henry for coffee at a local Starbucks one afternoon. We ended up spending three hours over coffee. It was amazing how much we had in common. After two vanilla dates, we were still enjoying each other, and Henry asked me if I would consider exploring his kinky side with him. When I agreed, we decided that he would come to my home and explore a simple role play. I asked him what he would like it to be. Without hesitation he shared that he would like to play the role of an older teenage boy (17 or 18) and have me play the role of his new stepmother. He suggested that our role play begin with his stepmother confronting him with evidence that he has been peeping on his teenage stepsister and has been borrowing her panties and using them to masturbate. He indicated that I could punish him in anyway I thought appropriate, and even indicated that I could make him masturbate in front of me if I so desired. (That was my first clue that Henry might be overly attracted to masturbation.)
We set up a date and time and I suggested to Henry that he could bring a long a few of his favorite spanking toys for me to consider using to punish him. I also planned to borrow a few things from Susan. Henry arrived on the designated evening dressed appropriately casually for a teenaged boy. I was dressed appropriately maturely. After some normal small talk, including Henry showing me the three spanking implements he brought along, I suggested that we start in the family room where Henry would be watching a sports event on TV. Henry made himself comfortable with the TV turned on. I shortly appeared and began to confront him about his behavior. I informed him that his step-sister (Molly) had told me that he had walked in on her in the bathroom without knocking on two separate occasions and that several pair of her panties had recently gone missing. Henry, of course denied everything, but didn't have much to say when I produced three pair of Molly's panties that I had found under his bed. He also had no good answer when I asked him to explain what appeared to be cum stains on the panties. His sole response was that he didn't understand what I was talking about.
I finally got to the point where I informed him that it was very clear to me what he had done and that I planned to punish him appropriately. I then proceeded with requiring him to remove his shirt and trousers and come stand before me. I then slowly lowered his underwear as I continued to scold him about his behavior. I also talked about how I was going to spank him. As I did this, Henry became quite aroused. I used this as a reason to justify that he needed to be punished.
I ended up turning Henry over my knee and giving him a very prolonged spanking with the implements he brought (a ruler, hairbrush, and a small wooden paddle). I decided not to use the items I had selected ... because by the time I used his selections at a moderate level, his bottom was nicely red. I also wanted to keep this first meeting at a moderate level and made a conscious decision to not make him masturbate. There will be time for that later.
I was also very much aware of the fact that Henry still had an erection when we finished.