BDSM: Trial And Error
By Ernest Winchester
Copyright: 2010 By Ernest Winchester
Let me tell you right up front, this isn’t going to be your normal, hackneyed BDSM or D/s story. I wish to hell it was, as you’ll see shortly. Okay, it started out as if it would be, but—well I’m getting ahead of myself.
I met Sylvia on one of the usual BDSM sites and we exchanged messages for several weeks, growing ever more intense with our chats. I should also say that I’m not new to this lifestyle. I’ve had a couple of subs a year and more ago but like many intense relationships, well, things just cooled, and they both left to find someone else. Maybe it was me or maybe not, I don’t know. If a sub doesn’t want to stay, if she is unwilling to submit, then it’s over. I know it’s hard to believe if you’re not into the scene, but the sub has the ultimate control. Anything beyond what the sub surrenders to is just brutality.
Now, to get back to Sylvia; the messages led to cybersex rather quickly and within a few weeks we were talking each other into masturbation orgasms, which is, as you probably know, rather hard to accomplish with one hand on the keyboard and the other elsewhere. I had her pinching her nipples very hard to give her some idea how a little pain made them more sensitive and intensified the orgasms that followed. From there, I introduced her to clothespins, instructing her how to start by taking large ‘bites’ of flesh so that the pressure was spread out and not too painful. I had her attach the pins to her nipples as well as her labia. Later, I had her take progressively small bites of flesh to increase the pain as she became accustom to the feeling.
I directed her in detail how she should dress for each of our sessions. I would start each session asking her what she was wearing; making sure that she remembered what I had told her at the end of the previous exchange and that she was taking my orders to heart. If she had failed to comply, I would admonish her that a good sub was to be attuned to her master’s will and bow to what ever he said. I of course, had no way of punishing her through the keyboard but I wanted her to understand what a Dom/sub relationship entailed.
In one session, I ordered her to strip and stand before her computer and describe in detail what she looked like. Neither of us had cameras attached to our computers so I had no way of confirming her description: five foot three, one hundred thirty pounds, blue eyes with brown hair. I asked her bra size. Thirty-six C, she replied. I realized all that would make her a little on the heavy side and she agreed she was a little pudgy. I told her that was okay; it would give me a greater target to paddle once we met. She sent me a : ) face with the next exchange so I had to presume that she was agreeable to corporal punishment. I know I should have assumed that she would have been, considering the site we were on, but I needed to clarify it before moving on.
I gave her a description of me: six foot one, one-eighty, with brown eyes and brown hair, graying at the temples. We had already exchanged our ages. I’m forty-two. She said she was thirty-three.
She typed back that I must be very distinguished looking and we agreed to exchange pictures. The picture that I sent her was of me in my black leather Dom’s pants and bare-chested. I had my arms crossed and a paddle in my right hand. It was one of my favorite implements—big enough to cover a lot of square inches of ass, yet small enough to swing with force. It was red and stood out in sharp contrast against the black leather. If her ass cheeks were indeed large, then that paddle would be perfect.
The picture that she sent me was a group photo. She was standing between two men. One was her old boyfriend and the other was her brother, she explained after I received the image. I was a little disappointed that she didn’t have a better, sexier picture, but I fully expected to get many more with my digital camera once we were together. Also, in the picture, she looked to be a bit beefier that she had said, but I had to smile, thinking that that would give me a reason to punish her right away after making her get on a scale.
Soon after, we agreed to phone contacts. She said that she had a phone that cost her for long distance so we arranged a time to meet on the phone and I was to call her once a week. Though we didn’t live all that far apart, we were in different states that made the calls long distance. My phone was bundled and long distance free within the US.
On the first call, I had her exploring her body, describing the sensations she was getting as her fingers traced every inch of her body and not just her erogenous zones. In fact I deliberately made her ignore her nipples and pussy, telling her to trail her fingertips close to them without touching any of them. I wanted her to understand that the entire human body was a delicate organism, rampant with nerve endings. The human voice could be a most intense organ, eliciting as much pleasure as any well placed appliance.
The second week when I called, there was no answer and I knew I was building up punishment points that I would exact from her flesh once we met in person. I didn’t call again until the following week and stayed off the BDSM site as a form of punishment.
“Sylvia.”
“Yes, Bill?”
“Of course.”
“I’m sorry I wasn’t here last week. I had to…”
“I don’t want excuses!” I said, making my voice stern.
“But…”
“No buts. A sub must always make herself available for her Dom. Do you understand?”
“Well, yes, but…”
“The only butt I want is yours across my knee. I’m keeping track of the number of times you’re to be punished once we meet. Do you understand?”
“Yes.”
“I think it’s time for you to start calling me Master. Is that understood.” It wasn’t really a question.
“Yes…Master.” I thought I detected a slight giggle in her voice, but I let it pass.
“Good. Now what are you wearing?”
“Just the clothes that I wore to work. I was a little late getting home…”
“Again with the excuses! Take them off, now.”
“Okay, just a minute.”
I heard a slight clunk as she placed the receiver down. Two minutes passed before she picked it up again.
“What took you so long?”
“I had to close the blinds. Sometime they stick.”
“Are you naked now?”
“Yes, ah Master.” Again I thought I could hear a little too much gaiety in her voice. I was sure that she still thought this was all a silly little game.
“Are you by your computer?”
“No, Master. I have only one phone and it is in the living room. That’s why I had to close the blinds.”
“Do you have your clothespins?”
“No Master. They are in the computer desk drawer.”
“Get them, at least eight.”
Again, moments passed before she returned to the phone. I had to remember that the last time I had instructed her to use the clothespins, she had only placed two on her nipples and two on her labia so she might have had to go else ware of get more.
“Are you near a couch?”
“Yes, Master.”
I instructed her to lie on her back and spread her legs. Then at my beckoning, she attached three of the pins to each side of her labia and one to each nipple. I also directed her to pinch only a small amount of her flesh within each wooden pin.
“Do they hurt?”
“Yes Master.” Her voice seemed to confirm that.
“Good. Now I want you to lie perfectly still and enjoy the pain. Keep the phone near your mouth. I want to hear your breathing.”
Her breathing started to come in short gasps, and I could hear slight groans.
“Please, Master…”
“Quiet! You’re not to speak until I tell you to.”
I waited for a full minute while her breaths continued in gasps, phasing into deeper moans.
“I want you to put your right hand down to your pussy and open your lips. Are your folds wet?”
“Ah, no Master.”
I was disappointed. A sub’s cunt should become aroused at the sound of her Master’s voice. Perhaps in time.
“I want you to slowly rub the area between your labia. Are the pins out of the way to allow you to do that?”
“Yes Master.” Her voice was coming in gasps just as her breathing was.
“Does that feel good?”
“Yes Master.”
“Good. In time you will be able to blend pain with pleasure to the point that you won’t be able to separate them.”
I had her continue until I could hear arousal in her voice. “Are you nearing an orgasm?”
“Yes Master.”
“You are not to come until I tell you to.”
“But Master, how…”
“You are not to question your Master. Your sole purpose in life is to please me. And right now it pleases me to make you wait. Now continue fingering your cunt, but you are not to come.”
As I listened to her breathing I could tell she was getting closer. It would do no good to let her come on her own in defiance of me, but I had no way of telling how soon she would cross over, so I allowed her to orgasm. Her cries of delight seemed genuine enough but I couldn’t be sure that she wasn’t acting. Only a face-to-face meeting would allow me to completely control our interaction.
I allowed her to remove the clothespins but directed her to place two side-by-side on her right breast, high enough for a bruise to be visible if she were to wear a low cut top. She was to leave them on long enough to produce the bruise and I told her she would need a top that would allow it to show when we met in person. I told her we should meet within a few days and I would be very disappointed if the bruise was not showing. I emphasized that it was only the first of many marks I would use to brand her as mine.
I arranged our first face-to-face at a small town about midway between our respective homes. It was to be only a brief encounter, public in nature, and only designed to allow a quick appraisal. In the middle of the small town was a diner right on the two-lane highway that bisected the burg and I had instructed her to be there at two in the afternoon, picking the time to hopefully find the dining room rather empty. I drove past the eatery well below the thirty-five mile an hour speed limit a little after two to see if her car was in the lot. She had given me a description of it, so I knew what to look for. It was there, so I drove around the small town for another twenty minutes before going in. A sub needs to learn that she is always at her Master’s beck and call. I had no reason to be punctual.
As I walked in I saw her immediately, sitting alone with no other patrons near her, I was glad to note. She was wearing all black as I had instructed and the low-slung top revealed ample cleavage, though from the distance, I couldn’t see the bruise. I could tell by the sparkle in her eyes that she recognized me instantly. I was dressed in black, jeans and a formfitting t-shirt. I’m egotistical enough to think I am pleasing to the eye and her concentrated look reinforced my sense of self. I could also read a great deal of hunger in her eyes and I wondered how long it had been since she had had a good fuck. I had never asked about her past life, telling her that from now on she was to be a blank slate for me. However, the gleam, along with the smirk that slowly spread across her lips did not display the proper attitude of a sub and I knew that we had a long way to go. As I stepped closer I could easily distinguish the dual marks on her right breast. She saw where my eyes were looking and she glanced down as if to confirm that the marks were showing.
Her face wasn’t all that beautiful and she definitely was on the pudgy side, but attitude and obedience more than looks mattered in a sub. I could easily envision her at my crotch doing her duty, those deep blue eyes showing intense pleasure at the taste of my cock. My cock started to swell at the thought, and bulged even more at the idea of her spread-eagled across any of the fixtures in a well-equipped dungeon. No amount of phone sex or BDSM videos could take the place of a well-trained sub kneeling at a Dom’s feet, hands manacled behind her back, ankles attached as well.
I was eager to have her filling the void that had existed for the many months since my last sub deserted me, but I knew that I had to go slow. A good sub took time to train.
“Sylvia.” I said, not smiling.