Who’s The Boss?

I found her. I seduced her. I made her explore her submissive side. I enslaved her. And now I was losing her. I do not like that idea.

Let me begin at the beginning. I am Dave, a teacher in an exclusive private school with more than 15 years of seniority. I am in my early 40's, 6 ft. tall and slightly overweight. Deidre just got her teaching license and was starting her first year at our school. I was asked to mentor her, to guide her through the early trials of teaching. This couldn’t have worked out any better.

Deidre was 5ft 2inches, blonde and blue eyed. She was a small, 32 inch hips, 22 inch waist but was a little top heavy, she was a 34c. She was cute, young enough to be my daughter. I would do my best to teach her all my experience, as Yogi Berra once said, and I was looking forward to getting very well rewarded for my efforts.

It did not take long for my mentoring to move outside the school and into restaurants and nite clubs. I kept my moves very subtle, and soon I found myself invited into her apartment for the proverbial “cup of coffee.”  As we were enjoying our conversation, I excused myself and went to the men’s room to take a piss. I had a feeling that I would need my cock for other things before too long. 

I reviewed what I knew about Diedre. I planned to make her my slave, everything about her made her a great candidate. She was not very experienced, and did not particularly enjoy the experience that she had. She had been with a few young men, who did not know how to satisfy her, and were awkward and came too soon. Her father was very strict and had spanked her until he died in a car accident when she was 12. She did not masturbate very often, and felt very guilty when she did. She was a case book example of repressed sexuality. I would use my age, experience and fatherly role to bring her into my web.

When I came out, she had changed into some thing “more comfortable”.  I could see that she had removed her bra and was wearing a “Hostess gown” that was flattered her figure. I could see her nipples stand out like small cherries. I knew that she wanted to see if she would be able to enjoy sex, as I had told her the problem was with her young partners, not with her. We did some necking and petting in the living room but I soon took her into her bedroom, where she still slept with stuffed animals. I was determined to give her such an experience as to insure her at least two orgasms and thereby begin her journey down the path toward being my total sex slave.

I unbuttoned her gown and started to kiss her beautiful tits, alternating between them, kissing, licking and sucking on those hard nipples, feeling them grow bigger and harder under my lips.  I often moved my mouth to her neck and lips, but I never ignored her tits. I played with them with my hands, rolling her nipples gently between my fingers, as they grew bigger and harder. I could hear the change in her breathing as she became excited. I took my time. I did not move below her waist until she was primed and ready. Finally I felt her body tense and her breathing became very labored. While sucking on one nipple and playing with the other, I gently ran my right hand down her body, lightly teasing her pussy hairs, until my fingers reached her clit. I started to rub it, very gently, but she bucked her hips against my hand. I made a note that I would have to train her in the future to remain quiet, to wait for my orders, but for now, this was most satisfactory.  I pushed and rubbed on her clit until I heard her scream with her first orgasm of the night.

She fell back, catching her breath from her first cum. I gave her a minute to relax while I got undressed myself. Then I spread her legs as I licked and sucked on her cunt. She started to climb the ladder once again, as my mouth on her clit was soon joined by two, and then three fingers up her cunt. She had never felt anything like this before. As I suspected, her boy friends knew nothing about satisfying a woman and were only interested in coming themselves. That was my goal too, of course, but, as they say, you catch more flies with honey than you do with vinegar. I would make Diedre want to please me. I would make her want to be my slave.

It did not take too much longer for Diedre to reach her peak again. Her hips were bucking against my mouth and fingers. I could feel her cunt muscles grabbing and clenching against my fingers. Once again I heard her screams as she came for a second time.

That was two for her and none for me. It was now my turn. While she was still dazed, I rolled her over and raised her ass. I penetrated her dripping cunt doggie style, as hard as I could. I would take my pleasure in her, beginning to teach her that she was there for my pleasure. I took her doggie style, because she did not expect it, she only knew the missionary position. She was about to protest when I reached under her body and pinched her nipples. She gasped, a little from pleasure and a little from pain. She would learn that the two are frequently interchangeable. I kept fucking her, slow and hard. She was still excited from her two previous orgasms. I could feel her getting in to the rhythm, responding to my thrusts. I could feel her cunt squeezing my cock, trying to milk my sperm. My she was tight. It felt good. I was determined to take her to the peak one more time before I allowed myself the pleasure of cumming, but I was getting too excited to last much longer. I brought my hand from her tits and moved it to her clit as I speeded up my thrusting. As I shot my spunk into that hot cunt, I rubbed her clit hard and could feel her cum as her cunt squeezed my cock. She started to scream just like in the porno movies, “YES, YES,  YES!!!” Then she said the words that I was waiting to hear. “Thank you, Thank you, How can I thank you? I cannot thank you enough!!”

I was waiting for that, and took the first step to making her my slave. I told her that when a woman wants to thank a man for a good fuck, and wants him to fuck her again, she takes his cock gently in her mouth and cleans it with her tongue, sucking and swallowing all his juices. Now you may not think much of this, but Deidre had never had a man’s cock in her mouth before. I don’t think she ever considered the possibility. She looked at me and asked me if I were joking. I told her that I guess she didn’t mean it when she asked what she could do to thank me and started to get up out of bed. I said I would see her in school. She panicked. She quickly apologized. I was not placated. I continued to get up. She started to cry. “Forgive me, please, I beg you, let me suck and clean your cock.” I hesitated, while I thought it over, crying, begging to suck my cock. Finally, I agreed to let her, but as I was already out of bed, she must get on her knees while she cleaned me off.

The road ahead would be long, but she had taken the first step. I don’t want to go through all the details of her progression from girl friend to submissive to slave. Very briefly, I started with lite bondage and blindfolds, keeping things very mild and making sure Deidre enjoyed the sex that I allowed her. I trained her to masturbate at my order while I watched. I ordered to Masturbate 3, 4, 5 times a day at home, or in public rest rooms. I forbade her from wearing underwear so she would always feel her juices dripping down her thighs. She got used to constant  climaxes. Then I forbade her all orgasms, but ordered her to continue masturbation. She was in a continuous state of arousal. Gradually, I demanded a price for granting her permission to climax. She became a wonderful cocksucker. She begged to be fucked in the ass. She drank my piss. She licked my ass. And she thanked me for granting her these privileges. I put her on toilet restraint, allowing her three set times to piss and requiring her to ask for permission for any other time. All was well until I introduced her to the paddle, the whip and the cane.

It is not that she objected. Oh yes, at first she screamed and balked but that ended very quickly. Her tolerance increased quickly and it would take a severe paddling to get her to scream although the cane could reduce her to tears very quickly. The problem was that she grew to like it to much. Rather than encouraging obedience to my desires, Deidre seemed to want to be punished. She seemed to go out of her way to disobey me. She did not treat me with the respect I demanded. I did not understand what was happening. I used the cane more and more as her conduct got worse and worse. Then I solved the mystery.

The school year was over and I invited some friends for an end of year party. Deidre acted like a spoiled child. She ate much more than I permitted her, she drank alcoholic beverages against my standing orders, she went to the bathroom without asking permission, and what was worse, she used the bathroom to masturbate to climax in what she thought was the privacy of my bathroom. When the party was over, I had her strip and hung her by the wrists with her ankles spread. As I started to warm her up with the paddle, I noticed that she seemed to becoming more and more sexually excited. As I switched to the cane, I ran my fingers through her cunt and felt her wetness. I determined to cane her harder than ever, and as I did, I heard her cum from my whipping. She was a pain slut. She got off on pain. She was disobeying me deliberately because she enjoyed being punished.

I enjoy whipping a slave occasionally. It is meant for my pleasure not for the pleasure of the slave. What I want from a slave is obedience. I do not want a constant battle of wills and I definitely do not want deliberate disobedience, topping from the bottom, behavior deliberately designed to provoke a whipping. I have used the whip and cane as a training motivator. The slave would obey to avoid the whip. How could I train a slave to obey when the slave wanted to be whipped? If I could not find a method of training Deidre to obey, I would have to give her up. I would not allow a relationship where the slave would have her own agenda, where the slave would not obey me automatically and without question.  I stayed up all night mulling over the problem. In the morning I had an idea. I made a phone call and  woke up Deidre. It was time for a new approach.