Jasmine

Chapter 4: Ass Training

It's one thing to tie or chain a girl up and discipline her. It is another to try and get to the next level of control in a D/s relationship whereby the sub begins to give up sexual control even when she is not in the presence of the Dominant. I had been enjoying my encounters with Jasmine but I had always wanted to have more than just a sex toy. For me, the highest level of connection is attained when the sub gives herself unconditionally. Now how to get her to that point? That's the question.

Jasmine was not a big fan of ass play and she really had no desire to have her ass screwed. That seemed a mighty shame given that her ass is perfectly formed. It's perfect not just for spanking and whipping, but for penetration as well with a nicely wrinkled, pink rosebud. Given her less than enthusiastic thoughts on ass play, I needed to develop her most basic submissive tendencies in order for her to overcome her inhibitions. At the same time, I was hoping this exercise would help develop our D/s bond.

Ass training seemed the perfect answer. If I set it up correctly, I could slowly get her used to the idea of having her ass penetrated and have her submissiveness brought to an even higher level. At the end of a very nice weekend, with Jasmine kneeling properly on the floor in front of me, I gave her the following instructions:

"Jasmine, it is time for us to begin your ass training." She shifted slightly from knee to knee, no doubt wondering where this was leading. "If you want to continue with our relationship, then you are going to have to learn to give yourself completely to me. And that includes your ass. But I'm not going to rush this, and chances are you will feel only the slightest bit of physical discomfort. I'm guessing that this will be a far greater mental challenge than a physical one. Are you prepared to continue?"

"Yes Sir."

"Good. Since you've already had the medium size plug in your ass, I know that you can handle something that size. But we are still going to start with the smaller plug for the first week. It is 5 inches long with a maximum diameter of 1 inch. It will be a good start for a daily trainer." When I said "daily trainer" I noticed some more nervous shifting from knee to knee. "You will wear the plug every day this week for 1 hour each day. You will begin promptly every evening at 7:00 pm and wear your plug until 8:00 pm. You will dress in a garter belt and stockings, and nothing else. You will get on your elbows and knees on your bed (so your ass sticks up nicely), insert the butt plug, and remain in position until your hour of training is complete. Do you understand?"

"Yes Sir."

"Furthermore, you will take my camcorder and set it up at the end of the bed. Each day when you begin you will turn on the camcorder, state what day and time it is, get into position on your elbows and knees with your ass facing the camera and then insert the plug. You are allowed to use lubricant to help ease the plug into your ass. You are also allowed to pleasure yourself during your hour if desired. Do you understand?"

"Yes Sir."

"Since I am going out of town this week, I will review the tape when I see you next Saturday. By then you will have had 5 days of training and will be off to a good start. If you miss a day, or do not wear the plug for a complete hour, then you will be punished when I see you again. Enjoy your week."

"Yes Sir. Enjoy your trip."

During the week I didn't call Jasmine on the phone. I didn't want to have to remind her to continue her training, but rather expected that she would do it without any further instruction from me. When I saw her the following Saturday, she brought the camcorder tape with her for my review. With Jasmine kneeling properly on the floor beside me, wearing the red ball gag and blindfold, I watched the tape.

Monday's taping started off showing her looking somewhat anxious. I expect she's never taped herself doing anything remotely sexual before, and certainly not shoving a butt plug up her own ass. Her shyness made it even more erotic than it already was. The beginning of the tape showed her sitting on the edge of the bed wearing a garter belt and stockings. In a somewhat quiet, nervous voice she said it was Monday and almost 7:00 pm. She then picked up the butt plug and squirted some lubricant on it and spread it around thoroughly on the plug with her index finger.

I hadn't really anticipated how awkward it is to insert a plug into one's own ass, especially when you're not used to it, so it was intriguing to watch her try and insert the thing into her own tight bottom. After lubing the plug she turned around and got into the position that I had instructed, on her knees, ass facing the camera, supporting herself with her left elbow as she reached back with the plug with her right hand towards her ass. She started by trying to reach around the outside of her ass, but quickly realized that wouldn't work. Then she reached between her spread legs and found she could reach her sphincter with the tip of the plug in this position. She began to gently rub the plug over her ass crack, and slowly circled her rosebud with the tip. She then began to push it in. In short order she yelped a little girl's yelp and dropped the plug on the bed. I don't think she got it in more than a half inch on the first try. I couldn't help but smile, and I was beginning to swell inside my pants. I reached over and patted her on the head, then returned my gaze back to the surprisingly entertaining film.

It occurred to me almost immediately that she needed to start by relaxing her sphincter muscle with her index finger before working the plug inside. For some reason, she didn't go that route. It could be that she didn't want to fuck her own ass with her finger, but just wanted to insert the plug and get this disagreeable task over with as quickly as possible. So instead she picked up the plug, gave it a few rubs around her ass then attempted to insert it once again. By the sounds she was making, she wasn't enjoying it much. She managed to get it in about an inch the second time before she tensed up again, yelped and dropped the plug on the bed.

She looked back over her shoulder at the camcorder with a look of annoyance. I half expected this to be the end of the tape and that I'd be thrashing Jasmine's ass shortly for not following orders. Then she lowered her head down onto the bed, reached up between her legs, and began to slowly circle her anus with her index finger. In her more relaxed position, with the gentle stimulation, she had her finger inserted in less than a minute and began to slowly finger fuck her own ass. The sporadic moaning sounds she was making made it seem she was getting used to the feeling, and might even be beginning to enjoy it, or at least finding it tolerable.

After about two minutes of fingering her ass, it was visible looser. She picked up the plug and brought it to her rosebud one more time. She managed to get it almost half way in when she lost leverage. She raised herself up off the bed so that she was sitting up on her knees, reached back with both hands, and shoved the plug home. The loud grunt she let out when it was inserted made Jasmine jump slightly beside me on the floor. Apparently she remembered that first day well, and recognized the sound of her self imposed plugging. I was very proud of her at that moment.

The rest of Monday's tape just showed her kneeling on her elbows and knees with her plugged ass prominently displayed on the screen. Very enticing. She had chosen not to masturbate even though I had allowed that option. Judging by the periodic grunts, she wasn't in a particularly horny mood that day anyway. I did note that she did not wear the plug for a complete hour that first day. Since it took her nine minutes to get it in, she made the mistake of only wearing it until 8:00 pm when she, all to eagerly, removed it. That was going to cost her nine strokes of an apple branch switch. One stroke for each minute not worn seemed appropriate.

The rest of the week went pretty much the same, except that she had learned to start off by finger fucking her ass to loosen it pry to inserting the butt plug. Unfortunately for Jasmine, even though she got much more efficient at inserting her trainer, she still didn't get 60 minutes of training time in for each day. Due to her lack of diligence she had accumulated 16 stripes of the switch. She was going to have a sore ass yet again this weekend.

I fast-forwarded through most of the week's tape. She never did masturbate herself to orgasm while in training. I could see that her slit was visibly wet, and she periodically rubbed herself a bit more than necessary once the plug was in place. But for the most part, she endured her training stoically. I couldn't help but wonder what she did with her wet slit after the plug was removed and the camcorder was turned off.

The shear erotic overload of witnessing this had, of course, given me a hard-on. When the tape was complete I turned to Jasmine, removed her gag, and had her give me a very satisfying blow job.

On Sunday when it was time for Jasmine to return back to her place, I decided to modify the weekly orders to make it more interesting. But first, I needed some answers.

"Jasmine, did you masturbate last week while I was gone?"

After a moments hesitation, "Yes Sir."

"I noticed that you did not masturbate during your training even though I had given you permission. Why not?"

"It was somewhat awkward and embarrassing to be in that position. Also, no one has ever seen me masturbate before Sir."

"This week you are only allowed to masturbate during your training sessions. If you pleasure yourself at any other time you will be punished, and I will be very disappointed in you. It's important that your sexual pleasure is associated with my pleasure. It will please me to see you masturbating during your training session. If you do not want to, that is OK, but you can't do it at any other time. Do you understand?"

"Yes Sir."

This would be an interesting week. Jasmine was an extremely horny girl and could cum with multiple gusto as I'd seen for myself many times. I was looking forward to seeing what her choice would be. Even though I did not go out of town this week, I again did not call her during the week since I wanted her to make her own choices.

The following Saturday she came to my house and presented me with the camcorder tape. Once things were properly set up (Jasmine in position with gag and blindfold), I eagerly ran the tape.

Monday, Tuesday, and Wednesday showed that she had become proficient at inserting a butt plug (I need to go to the medium size for the following week), and that she had learned to keep time properly (no punishment switching for less than 60 minutes of training this week). I also noticed that even though her slit was wet, she did not unduly touch herself for the first three days.

Thursday began very much the same, but she did seem a bit more fidgety than normal. Lots of low moaning and subtle ass swaying from side to side. Then, after about 10 minutes, her right hand found its way to her moist pussy. I had been fast-forwarding through and quickly had to stop and back up the tape. Upon touching her lips gingerly with her hand, she let out a long sensuous moan. It was highly arousing watching her rub her pussy while her plugged ass swayed slowly from side to side. Then she stopped.

I could hear that her breathing had quickened and could see that her pretty ass was still swaying from side to side. She was struggling with the need for sexual release versus the embarrassing reality of knowing I would see the tape later. As I expected, sexual tension won the day and she began furiously rubbing her pussy. In less than a minute she had a very loud orgasm. To her credit, she did stay in position. After a few moments of rest she began to thoroughly finger fuck her pussy, and again had a very loud orgasm. I was not surprised that she had many multiple orgasms (I lost count after a bit), but I was surprised that she stayed in position playing with herself for at least an hour and a half, butt plug and all. I guess time fly's when you're having fun.

While watching Jasmine enjoy her Thursday training on the tape, I looked over at her kneeling beside the couch and noticed that she was blushing furiously. She could clearly hear the sound of her own orgasms playing on the tape.

"Your secret is out Jasmine. You are a horny slut to be able to cum that many times with a butt plug in your ass."

She's becoming a better submissive with every passing week. I'm very pleased.