I go to the gym to work out, not to meet women, but I got into discussion with an older woman, my age, who I had seen working out at my gym on several occasions. Her name is Molly. We talked about our workout goals and gave a little bit of background about ourselves. She asked if I was dating anyone and I told her I wasn't but was open to the possibility. She got more pointed and hinted at whether I was still interested in sex. "Of course I would like a friend with benefits," I said. "Who wouldn't? Everyone should have one."
She agreed and I told her that we might not be on the same page sexually. How so? "I'm not into vanilla sex anymore. I like a little kink in my sex life," I said.
"Like what?" she asked.
I told her I was into light bondage and spanking and sex toys. She agreed that she had wondered about that and was interested in trying it. I suggested we meet for coffee and discuss it further.
We met later that week at a Starbucks. I went ahead of time and took a room at a hotel and moved my gym bag full of implements to the room in the unlikely event that she showed enough interest to proceed immediately to participation. We had coffee and the more we talked, the spicier she got and I could tell she was very turned on as I explained the basics of the dom/sub dynamic. When I suggested we go to the hotel room, she readily accepted.
We got to the room and Molly was all bright and excited with anticipation. It was a plain hotel room and I had secured a room at the far end of the hotel where all the other rooms were vacant at this time of year. I sat on the edge of the bed and told her to come sit on my lap, that I was going to interview her. Molly was wearing a skirt, not too conservative, not too revealing. I told her to call me Daddy and asked if she understood.
"Yes," she replied.
I slapped her face lightly and said, "Yes Daddy."
She looked surprised at first, then smiled and repeated, "Yes, Daddy."
I asked if she was wearing underwear and told her to remove her panties. She stood up and reached under her dress and took out a pair of sexy panties which indicated she had been thinking of the possibility of sex on this first date as well.
I took her panties and set them aside on the bed and then told her she should have asked my permission to stand up and she would have to be punished for her mistake. I told her to separate her knees a little to allow me to put my hand up her dress. I then asked her when the last time she had sex with another man was and she said it had been several months.
"Did he play with your pussy," I asked and began to massage her between the legs.
"Yes Daddy," she replied, anxious to show me she was catching on.
"Did he lick your pussy?" I asked.
"No Daddy. That's why I didn't want to see him anymore."
"Did you suck his cock?"
"Yes Daddy."
"Did he come in your mouth?"
"No Daddy."
"Would you have liked that?"
"If it had been you, Daddy, I would have liked it," she answered.
I followed up with some questions about when she had first had sex, whether she had ever had sex with a woman, how often she masturbated, and whether she had ever been tied up or spanked before. By now I had inserted a finger into her cunt and she was responding with gushing wetness. I told her she was a perverted slut and would have to be punished. I told her to go into the bathroom and close the door and sit on the toilet and reflect on her punishment.
While Molly was anticipating what awaited her, I went to my gym bag and began extracting the implements which would make our session a success. There was a flogger, a leather strap and a short cane. I took out a rabbit, a flexible string of anal beads and a small, beginner size butt plug. I went to the bathroom door and opened it. She was sitting on the toilet and looked up at me expectantly. I told her to come out. She came up to me and I asked her if she had touched herself in the bathroom. "No Daddy."
"Good girl," I said.
I told her to lie across my lap with her legs and arms hanging down. She obeyed and I lifted her dress, revealing her bum. For an older woman, she had a well-formed ass, not too flabby, but not pert like a young woman's. I rubbed my hand across it. I squeezed it. I gave it a sharp slap, first one cheek, then the other, but not too hard. There was a sharp intake of breath, but otherwise she made no noise and said nothing.
"You are a very bad girl, a nasty girl, and you need to be punished. Do you understand?"
"Yes Daddy."
