I met Kelly in a Starbucks close to a hotel off Interstate 80. It was about an hour from where she lived, and four hours from my home. I was en route to a conference, so that made it convenient. This was our first face-to-face encounter after several weeks of correspondence via a BDSM website. She was married, and in her late thirties. Her hair was short and dark, with a slight curl to it. She had just come from her job as a legal secretary, and was dressed in a conservative blouse and skirt ensemble with black heels. She was attractive, and in the same marital position as myself. Perfect, since all I required was a little extra-curricular activity. Nothing beyond that.
She was nervous, much more so than I. I had fooled around quite a bit before getting married. Kelly had married early in college. Her sexual experience was scant, and that was now catching up with her. Sex with her husband was an occasionally boring routine at this point. She had fantasies that she didn't feel comfortable bringing up with him, and they were becoming an obsession with her. It's an old story.
Despite her nervousness, our chat went well. We didn't discuss anything of a sexual nature, although we had online. Instead, we just got acquainted. After finishing our decaf cappuccinos, the time had come to make a decision. We were leaving, either separately or together. Kelly took a moment to decide, and then walked across to the hotel with me.
We rode up the elevator in silence. Once we reached the door to our room, I stopped before opening it.
"We start as soon as we're inside" I said. "Do you understand?"
She nodded yes.
"You understand what we're about to do?"
"Yes", she answered.
"Select a safe-word."
"Chiffon."
I unlocked the door and ushered her in.
Kelly walked in ahead of me and turned around.
"What would you like...?"
"Don't ever speak unless you are spoken to."
She ceased to speak.
"You will be punished for that. Come here to the entrance, turn and face the wall."
Kelly did as she was told. She was now standing in front of the door facing the wall. I stood in back of her.
"Are you wearing what you were ordered to wear?"
She nodded yes.
"You are to answer yes or no to a yes or no question."
"Yes."
"And you are to address me correctly when you answer."
Yes...master."
"Strip down to what you were ordered to wear, then put your arms up against the wall, so that I may inspect you. Stare straight ahead at all times."
She just stood there.
"You're hesitating. You're very nervous, aren't you?"
"Yes...master" she answered back. Good, by answering me correctly, I knew she wasn't out of the game yet.
"Do you wish to use your safe word?"
She nodded no.
"The time for hesitation is over. Obey me, or we are done. The decision is yours."
Kelly stood there for another moment, and then started undoing the buttons of her blouse. She was fumbling out of nervousness, but finally succeeded in taking the blouse off.
"Let it fall to the floor" I instructed her. She complied.
"Continue."
She loosened her skirt, let it fall, and stepped out of it. She hesitated again.
"Finish as instructed. Now. I will be punishing you for taking too long."
Kelly took off her bra, and then her underpants. She put up her arms, and leaned against the wall. I looked her up and down. She was maybe a few pounds over her normal weight, but not by much. She clearly exercised. Her legs were in good shape. Her ass was round, but not out of proportion with the rest of her body. As instructed, she still had on a pair of black nylons, and black heels.
"Spread your legs so that your feet are approximately two feet apart."
Kelly spread her legs.
I left her there and went into the room. There was a couch with a coffee table in front of it. I took some items out of my suitcase and placed them on the table. I sat down on the couch to admire Kelly. She was still staring straight ahead as ordered, and couldn't see me. I imagined she was getting more anxious by the second.
After what passed for a reasonable amount of time (for me), I got up and walked over to her. Standing behind her, I could here her breathing. Her breaths were coming out in controlled, regular breaths. She was obviously working hard at trying to stay calm.
I stood as close as I could behind her without touching her while I counted to 60 in my head. I then reached down and lightly ran my finger along her inner thigh. She almost jumped out of her skin. But she remained in place, staring straight ahead.
I caressed her thighs some more, and then moved on to other parts of her body. I fondled and caressed up and down her legs, back, and abdomen for a while. Then I reached in and grabbed a breast. I fondled, and then squeezed it.
I let go and just stood there again, without touching her. Her breathing was extraordinarily heavy now. I counted to 60 again.
Next, I gripped the back of her neck with my left hand, and reached down between her legs with my right. My fingers went up above her cunt. I then drew them back slowly until I came to the top of the crack in her ass. She struggled to remain silent, and whimpered a little.
I squeezed her ass cheeks, and went back to giving her cunt some attention. She was fairly moist down there, and it didn't take long before I was fingering her. I revved her up for a minute. I think she could have come in a matter of seconds, if I'd let her.
I retracted my fingers, grabbed her hair with my other hand, and put my fingers in front of her mouth.
"Clean them" I ordered, "but leave them moist, so that I can inspect you "
Kelly licked and sucked on my fingers until I pulled them out of her mouth. While keeping my grip on her hair, I inserted my ring finger into her asshole, just the tip at first. I had to wait for her muscles to relax enough for me to push farther in. Once I was in all the way, I left it there, and silently counted to 60 again. I then retracted my finger and released her hair.
"Go to the table and kneel in front of it with your hands behind your head", I said. While Kelly obeyed, I went into the bathroom to wash my hands, then came out and sat on the couch on the other side of the table. She was kneeling as instructed, so we were facing each other.
"This is your position. When I order you to assume the position, this is what I expect."
I pointed to a piece of paper among the items on the table.
"This is your contract. Read it silently to yourself." She scanned it, and then looked up at me.
"Have you finished?"
