Jenny trains Simon to take extreme anal abuse

Upon entering the house Mistress Jenny saw Simon using a moist towelette to clean the butt plug as he headed towards the parlor, she assumed to put it away in its proper place. She followed him into the parlor and handed him the remote control and she watched as he put her toys away. "Simon, watching you clean that butt plug has made me realize that you haven't had a good session of ass training for a while. I think we should do something about that right now."

Simon was obviously not expecting this, and his eyes looked around the room while he was looking for something to say that might get him out of what was coming. He knew that it was hopeless however, and he took a deep breath before answering. "Yes Mistress Jenny."

"I will want you to be clean inside, I don't want you stinking up on me while I am helping you practice your exercises. Go clean yourself well, outside and in, and then wait for me in at the Exam Table." Mistress Jenny's house had many rooms, and almost all of them had equipment for various purposes. One of the dungeons held medical equipment, one piece of which was a gynecological examination chair, but build with solid restraints, and various additions that make it a perfect place to torment a slave for hours on end. Today she just wanted Simon to feel his ass being seriously stretched, and to punish him severely when he failed the final test. She would make sure he failed, even if she had to cheat, which of course wasn't cheating if she did it. Sometimes always being right was fun.

Mistress Jenny didn't want to wear her street clothes for this, so she went into her dressing room to change. After dropping her current clothes into the laundry hamper, she walked over to where her leather outfits were kept. She felt like keeping it simple, so she donned a basic black leather bra, and a very short pair of leather shorts. She knew this simple outfit was the one that caused the most response from her slaves, they all liked how it covered her, but showed enough that they could think about being rewarded by her revealing even more. She thought about shoes, and decided that as this was only a training exercise it wouldn't matter if she went barefoot, which she wanted to do after being on her feet for nearly an hour during the shopping trip. She had only been a couple of minutes, and she knew that Simon would need a lot more time than that to clean himself properly. Additionally she wanted to have him wait for her. A slaves apprehension grew the longer he was forced to wait for her attention, and when he knew what was coming he would be thinking about the suffering that was to come, and if that was maintained for long enough, it would increase the sensation when he finally felt it. It was amazing how often doing nothing was exactly the right thing to do.

So she had some time to kill. Heading back into the parlor Mistress Jenny went to the intercom. "Patrick, collect my shopping and bring it into the parlor please." Mistress Jenny had seen a new intercom system that gave all her slaves earpieces they could wear when they were on call, so she could say their name and call them directly. Maybe that was a present one of her slaves could get her, after all, it would help them serve her better and they all wanted that. She was still thinking of this when Patrick entered the room with her packages. "Put the books on my side table, and then put all the candles away."

"Of course Mistress Jenny." She sat down as Patrick brought the books to her and then went back to open the box of candles.

When he got to the black candles she had bought to replace the ones of wax play, he sneaked a look at her, as he was one of the people who suffered their use the night before. He was obviously reminded of this as he put the candles that belonged in here away. Then he collected the rest of them back in the box and left the room to put them away properly.

Mistress Jenny told herself that she would just read one chapter before going and starting Simon's training, but she liked the book and she had read three before she felt she had to put it down and go and deal with him. He would be nervous that he she had forgotten him, which sometimes she did on purpose. She decided to sneak up to the room and open the door suddenly, just to see if he was waiting for her properly. An evil glint came into her eye as she slowly crept barefoot through the house.


Mistress Jenny opened the door in one swift movement, and saw Simon kneeling in the correct position. His hands were on his knees, and his bottom was held just a few inches above his heels, his back was straight and his head held upright. There had been no indication of movement when the door opened, and she was pleased that he had maintained this position even though he had no idea how long she was going to be. He smiled at her as he saw her approval.

"Ready for your training session?"

"Of course Mistress Jenny." There was no sound of apprehension in his voice, so either we was expecting to be able to please her, or he was really in the mood to suffer, either way it meant fun for the woman in charge.

"Then get into the chair." Mistress Jenny turned away from him grabbed the medical trolley that was kept in this room. As Simon climbed up into the chair she went to one of the cabinets in the room and took out a large pump pack of lubricant and put it in the holder on the side of the trolley which was specifically designed to hold it. Mistress Jenny often played these games. Then she grabbed a towel and placed it on top of the trolley to hold all the toys she was planning to use, but first she had to make sure Simon was securely in place.

Turning back to Simon he was just settling into position, which involved him climbing up onto the chair, and then reclining back in it. Then he had to lift his legs high to place them in the stirrups which would hold his legs up and out, giving her complete access to his ass and holding it at the perfect angle for her to put whatever she wanted in it. She approached the chair and started to fasten the leather restraints around his ankles. The chair was designed to ensure that even a strong slave couldn't move the stirrups when they were secured in place, and they both knew that with his ankles secured nothing he could do could prevent her doing whatever Mistress Jenny wanted to his ass, cock or balls. There was nothing he could do to cover or protect them at all. Then she went around the back of the chair and secured his hands out to the sides on either side of his head. This would give him the least possible leverage to move around in the chair.

"For this exam Simon, you will need to correctly identify size, texture and shape of items that I insert into you. So you will need to pay attention and wont be able to think about something else while I am raping your ass. Wont that be fun?" Mistress Jenny added a giggle to the question, to let Simon know that she was going to be especially brutal to him.

"That does sound like fun Mistress Jenny. Thank you." His words said yes, but his voice didn't sound so certain.

Mistress Jenny then retrieved a black leather blindfold that was padded with sheepskin. She didn't want any part of him to be drawing his attention away from what she was doing to his ass. He lifted his head when she approached with it to aid her in placing it over his eyes so he couldn't see. Mistress Jenny knew that he was doing everything he could to support her with whatever she wanted to do to him, and knew that Simon was a slave she was going to be very proud of for a long time, though she had no plans to be proud of him by the end of todays lesson.

Once the blindfold was in place Mistress Jenny went back and collected the trolley and wheeled it over to the beautiful wooden cupboard that she had made to hold her large selection of anal toys. Mistress Jenny loved abusing a slaves ass, and all of her slaves knew to expect special attention in that area. Many of them had given her toys for her to use on them, and she kept many of them here. At least once a week Mistress Jenny would send a slave in here to clean them all, often as a prelude to her using many of them on him, which was probably why Simon was so surprised at the sudden announcement of todays training. Inside the cupboard was a large number of shelves, each covered in a dark purple felt. These shelves were on draw mechanisms that allowed her to extend the shelf so better see the toys that were resting on it, each in their proper place. There were at least a hundred different anal toys on these shelves, varying from small finger sized ones all the way up to ones that only the most dedicated of anal slaves could take without damage, one of these was nearly a foot in diameter.

Mistress Jenny spent several minutes choosing the items she planned to rape Simon's ass with. She had told him he she was expecting him to be able to identify each one only by the feel of it inside him, and she wondered how well he remembered them all. She was going to find out, and this was going to be fun. She finally settled on 6 items for him to identify, and then the one for the final test. She placed all of these in order on the trolley, and then closed the cupboard. She then wheeled the trolley into a position where she would be able to reach it, and then placed a stool in front of the chair between Simon's feet for her to sit on.

"As I expect you to identify each item I wont be using a lot of lube, otherwise you wouldn't feel anything and that wouldn't be fair would it?" She asked the question knowing that there wasn't an answer that would not condemn him. Either he could agree and know that this ass raping was going to hurt more than normal, or try to convince her otherwise knowing that if he did so, then he was sure to fail this test.

"Thank you for being so fair to me Mistress Jenny." He decided that pain was better than failure. She smiled though he couldn't see it.


"I am ready Mistress Jenny."

She reached over to the trolley and picked up the item she had selected to start this 'test'.


Mistress Jenny had decided to start with a firm vibrator that was sheathed in a jelly like rubber fully molded like a cock and really no larger than Simon's own. She was not planning on making it vibrate at all, it was just one she found that was a good size. Starting a slave off with a cock shape always proved that at any point they would be ready for an ass fucking from one of the other slaves if she so ordered. She knew this would be no real surprise to Simon, and he would be able to guess very easily, but she didn't want him to fail right away. Using the pump pack of lubricant, she put a little bit on the tip of the vibrator, and then starting rubbing it against Simon's anus, to spread the lube around a bit, not pushing it in at all yet.

"Mistress Jenny," the way Simon said this made her know he had a question. "Would you like me to describe what I am feeling and what I am thinking? This would mean I am wrong with a lot of what I say, and I hope that you will not judge me on that as it would probably cause me to be more careful in what I am saying, but I thought it might please you to hear what I am thinking before I declare my answer to you."

"That would be good Simon, I would enjoy hearing what you are thinking and feeling." Mistress Jenny was genuinely pleased with this idea. She rotated the head of the vibrator on the surface on Simon's anus a couple of times, then applied pressure and pushed it so that about 2 inches passed into his ass.

Simon sniffed, a closed mouth gasp, the started to speak. "OK. That feels a little bit squishy, but seems to have no flexibility at all. It is shaped like a cock, and only about the thickness of one, probably about 3 cm." Mistress Jenny applied more pressure, pushing it deeper into Simon's ass, but after the initial insertion it did not seem to be causing him any discomfort. "It doesn't seem to be getting any thicker, and it is definately not bending at all."

Simon then raised his voice level a little, making it clear that he was announcing his opinion. "Mistress Jenny, that is a vibrator covered by a cock shaped rubber cover and is about 3cm in diameter."

"Very good Simon, but that was an easy one." Mistress Jenny pushed the vibrator in a little further, then started to twist it. "How deep inside you do you think it is?"

"I would say about 5 inches Mistess Jenny, and you are twisting it, which I can feel at the entrance, and a little bit further in. The lack of lubrication makes it a lot easier to feel, but it is not stretching me so it is not uncomfortable. It feels really good actually." It has always seemed odd to her that when talking about the width of a dildo the slaves always used centimeters as the measure, but when they talked about length the used inches. She was not sure why this was, but she did it herself.

Mistress Jenny smiled, knowing that this was only the warm up. Slowly she pulled the vibrator out of him a few inches and was happy to see that there was no trace of any of his filth on it. She then pushed it back in, and while twisting it she started to fuck his ass with it. Simon started to breathe deeply as the pleasure from this started to get him excited, and his cock, which was already firm started to stretch even more. For about a minute Mistress Jenny continued to pump his ass with the vibrator and as he relaxed she could feel the pressure from him was lessening. He had relaxed into this and his anus was not clenching at all, the passage of the shaft was smooth.

"Now it is time for you to start your exercises Simon. I am going to push this into you almost to it's base, then I am going to let go and you are to hold it inside you while you slowly count to ten. Then I want you to slowly push it out of you, not too fast, until it is almost all the way out, then you are to hold it there until I push it back in and you will repeat the exercise. I want to make sure you have control over the tightness of your ass, and that you can grip anything I put in there and control the speed with which you expel it. Do you understand?" This was not a hard exercise with a toy of this style, but with more flexible toys, or larger toys, it got significantly harder to accomplish.

"I understand Mistress Jenny."

Mistress Jenny pushed on the base of the vibrator until almost all of the rubber cover was hidden inside him. Then she told him to start the exercise and let go. Slowly Simon counted to ten, during this time the vibrator moved only slightly out, as he tried to overcome his bodies natural reflex to push the obstruction out of him. Upon completion of the count the vibrator started to move, slowly at first, the faster, then slower again. In only a few seconds he had pushed the vibrator most of the way out of him, and then he paused and tried to hold it in place. It started to slide out from it's own weight and Mistress Jenny quickly put her hand to the end of it to halt it's further progress.

"You pushed it out too fast. Try again." Mistress Jenny pushed the vibrator in deeply again, and the exercise repeated. Simon did better the second time, and continued to improve for the 20 repetitions that Mistress Jenny had planned for him to repeat this. Only three times did the vibrator fall out of him, and each time she scolded him and told him, pushed the vibrator in hard and told him to improve "or else".

Simon's last attempt proved that practice was helping him. For the count of 10 the vibrator didn't move at all, and his expulsion was slow and steady. Just before the head of the vibrator became visible he tightened his anus and held the vibrator in place, and Mistress Jenny saw his grip on it was firm.

"You have done very well Simon, but this was really too easy for you. Lets move onto something a little more challenging." Mistress Jenny returned the vibrator to the trolley, and picked up the next object.


The next item that Mistress Jenny had chosen to abuse Simon's ass with was a dildo. It was longer than the vibrator she had used, and a lot more flexible as there was no solid core to it. There was no molding on it's surface and it was completely smooth. There was a knob on the end of this dildo, maybe 4 cm in diameter, when then went down to a 2cm wide shaft, which over it's 10 inch length slowly expanded back out to 4cm. The challenge for Simon with this dildo was not going to be holding it in at the end, but in controlling the speed with which he expelled it. Mistress Jenny applied only a small amount of lubricant to the head of the dildo before raising it to Simon's waiting asshole.

Like last time Mistress Jenny spent a few seconds moving the dildo around Simon's anus before applying any real pressure, as soon as he felt the initial contact he started to speak.

"This one feels round, like a ball, it also seems to be very smooth and quite firm." This was kind of true, while the dildo itself was very flexible and could bend a lot, the ball on the head was a lot denser and would not feel so bendy. Mistress Jenny applied more pressure, feeling the head of the dildo meeting resistance until it finally popped in quickly. Due to how flexible the dildo itself was, she had had to hold the dildo very close to the head to apply the pressure without it just sliding away from his ass.

As it popped inside him Simon breathed in sharply, "Ahh, the head on this is quite firm, but very smooth and after the head it seems to fall back to a much smaller diameter, definitely narrower than the first one used. It is still very smooth and I seem to be able to compress it." Mistress Jenny could see Simon clenching and unclenching his anus, trying to get as much information about the object inside him as possible. Now that the head of the dildo was inside him it didn't take as much work to apply the pressure to move it in further, because it really had no where else to go. It did bend before moving in, but Mistress Jenny was able to control it.

"It is getting wider as you push it in deeper, and it doesn't seem to be getting any firmer as it does so." Simon seemed to make a decision. "Mistress Jenny, is this the long purple bendy one with the round knob on the end?" Damn, he knew her collection too well, but still, he had identified the object correctly. The goal of this was not to try to make him guess wrong, but to get him to pay attention to what was going on inside his ass, so if he was able to identify so quickly, then he was definately paying attention.

"Correct, you are a dedicated little ass slave aren't you?" Mistress Jenny saw his cock twitch as he told her that he really wanted to be as good an ass slave as he could. He was enjoying this, and so was she.

Mistress Jenny started to pump Simon's ass with the dildo, again causing it to start to relax into the extra width as she pushed it in deeper. This dildo was so smooth that twisting it would almost certainly have no effect, something that was confirmed for her when she did twist it around once and Simon remained silent, apparently unaware she had done it. The only real purpose a dildo like this had was to brutally fuck a slave with it, because it was so soft there was no way that she should do anything that would damage him. Mistress Jenny started quickly thrusting the dildo deep into Simon's ass and pulling it out to the head again, increasing speed as she got a better grip and improved her positioning for this. In less than a minute Simon was groaning with pleasure at the sensation.

"It really looks like you are enjoying this one too much, well lets see how you go with your lessons. Same rules as last time." Mistress Jenny pushed the dildo into Simon's ass about 8 inches, and let go. It was instantly apparent that Simon was going to have problems holding this dildo in place for the slow count to 10, already it was starting to slide out of him.
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