The Loser

This is the number one person I would want to session with. He is one of the only two people in the whole world who I have ever felt real sexual attraction for and, like the moron his is, he squandered it. In fact, he told me that we could not become involved because it would cut into his time playing on-line games too much, then proceeded to play then so much of the time that he failed out of school. See what I mean? Incredibly stupid. So what makes him sexually compelling? Other than the fact that he kept me in a constant state of being pissed off, I really can’t say. Maybe it was because he defied me and I wanted to break him, to prove my will was stronger.

I know I said my sessions aren’t sexual, but this would be the one exception. In essence, I would want to do a wide variety of things with him, and just completely immerse him in a range of BDSM activities. But it would be a very slow, sensual immersion. I imagine, because he’s rather closeted in his game world and also doesn’t get very much attention from women, that he would be ignorant, yet slightly curious about BDSM, his main image of a dominatrix the generic stereotype found in porn. My role would be as his teacher, his mentor, the one who initiates his into the dark side.

Of course, I would be all glamed up in my most extravagant fetish wear and most shocking make-up. I would be HOT and he would be so sorry he hadn’t seized the opportunity when he could have had me. I would start just by showing him some of the toys, letting him touch them and telling him about their uses while he wonders if I would use them on him and if he will be able to take it. Then, I would begin with some simple wrist bondage. I would gently drape the rope across his arms and execute the tie slowly, so he could follow each and every step.

Now, the corporal part of the session would begin. I would have him kneel on a raised surface like a bed or even just lie flat because it’s his first time and he probably can’t handle a real flogging. Perhaps I might tie his wrist binding to the front of the bed too, just to make sure he didn’t go anywhere. I would use at least four implements: a fur flogger, a flat leather one, a braided cat, and a crop. I would spend a long time running each one over his skin first, stroking him slowly with it while describing what it’s made of, how it works, and the sensations it will deliver. When I got to the braided cat, I would be sure to grind the tails hard against his skin so that he could feel the shape of the braids.

Starting very slowly and gently, I would gradually build up the intensity, my intention not necessarily to cause a great deal of pain but, definitely, to leave some mark. Not a visual one perhaps, but something he could feel with every movement to make him think of me always afterwards. In addition to the instruments themselves, I would have a bowl of ice cubes handy as well, to periodically run across his hot, reddened skin and I would take great enjoyment in watching them melt and seeing the beads of cold water trickle down his skin.

The next part would involve foot worship with him kneeling on the floor and I now seated comfortably on the bed. Again, my role would be as a trainer. “Now listen carefully because I know you are none too bright.” I would explain very slowly, using small words, how he should remove my shoes and stockings and give me a foot and leg massage. My attitude would be one of exaggerated patience and boredom, as if I was doing him a huge favor by showing him how to treat a lady, since he is far too dumb/lazy to figure it out himself (which is true enough). While he was worshiping one foot, I would take the other foot and play with his hair, letting the strands slide between my toes, then clamping them down hard and giving it a yank.

I’d show him some more things too, including a number of CBT toys. After all, he, obviously, doesn’t have the slightest clue about what to do with his penis, since he didn’t even attempt to please me with it before. So, I might as well use it to amuse myself. At least it serves some purpose that way and I would make this fact abundantly clear to him as I slowly and carefully threaded his anatomy through the ball stretcher or vice. Again, I would be very slow about my work, taking long pauses between each turn of the screw. As his bits and pieces became more stretched, flattened, distended, I would mock him for how ridiculous they look and how fitting this is since his use of them has been equally ridiculous. I might repeat the same procedure with a parachute, gradually hanging weights with the same slow languidness.

Of course, he would also have to be punished for his insult in abandoning me for a game. So, I would lock him up in a cage and make him watch as I went on line and deleted all his accounts. Or, even better, I could be like Guinevere and order him to “do his worst.” I would make him go online and act like a total fool in front of the other people he knows, deliberately sabotage any groups he joins and get himself kicked out of his guilds, until he would be so totally humiliated he would never WANT to play again. Now don’t get me wrong. There’s nothing inherently wrong with playing video games, even playing them a lot. I do it myself. But, when it reaches the point where you can’t sustain normal functions, like a job or a relationship, then it’s gone too far.

After that, he would have a lot of free time on his hands, that he had formerly spent playing games. Of course, I wouldn’t want him always sitting around doing nothing, so I would provide him with something to do and, being generous like I am, it would also be something that would make him a better person. I find some (very long) works of classic literature I could assign him to read. He would also have the honor of escorting me to the ballet, the opera, art museums, and other high culture events, all the while listening to me lecture him on the material we were viewing , liberally spiced with commentary about what a pathetic looser he would be without my generosity. Afterwards, there would be quizzes and, if he didn’t do well, it would be back to the dungeon for some “memory sharpening.”