MEETING MISTRESS GERTRUDE

The Pain

"Another slave Gertrude, easy work this one too. Maybe not easy work but you are getting better and better. You’re my best student, better than I was." I heard Michael say as I went upstairs to watch tony through the video monitors. I looked into Michael’s eyes. It was still strange to have him as my equal. I used to be Michael’s slave once, but as he said I was always a top in a bottoms position. Once he recognised this, he became my mentor, as a Master to a Mistress, rather than a Master to a slave. It was thanks to Michael that I was able to explore my true identity, to develop, not only sexually, but as a person.

"mel will never be a Mistress" he interrupted my thoughts. "She is still confused but underneath her pushy exterior she really is a submissive little slave. "I thought about our daughter. From a very early age she exhibited traits of a bi-submissive. As soon as she realised what we were doing and became legally adult, she joined our group of friends as a bottom, willing to be exploited by anyone. I often wandered how could she have turned out like that, a daughter of two very strong dominators.

"How long will we leave him? He’s probably very uncomfortable, not used to being spread out like that. Too bad! That cream should still work for a couple of hours. So how about a long leisurely afternoon with your Mistress? I haven’t yet been satisfied..." I asked Michael.

Approximately three hours later, we were back in the dungeon room where tony was held. mel and sofia were with me, also refreshed. I assume they had some fun together while we were gone. tony was looking uncomfortable, his arms and legs would have begun to cramp by now.

"Adjust the cross horizontally mel we are going to introduce our little initiate to some pain" I instructed mel. She moved the pedals underneath the cross so that it swivelled and tony was now lying on his back being supported by the aluminium tubes underneath him. sofia brought forward the metal cock elbow which she placed over tony’s cock so that he could not get an erection. I watched the satisfaction on her face, this girl hated men.

"Take the blindfold off him, let him watch." A little too eagerly mel walked over to tony’s head and yanked the blindfold off, flashing tony one of her smiles. "The gag?" mel asked but it was too soon for that. I watched tony squint his eyes as he looked around the room. He first looked at himself with terror in his eyes. I laughed inside, he probably thought we broke his skin when we whipped him, yet all he saw was red skin and his shaved cock. What a naive attitude to an experienced Mistress! Finally he saw me.

"Yes that’s right slave I am Mistress Gertrude, the one who will break your will. You have passed the first stage of the initiation as sofia’s stomach full of your cum can attest. I am afraid the next two stages will not be as pleasurable for you. It is your turn to please others like any good slave should. slaves satisfy yourselves as you apply the nipple torture." I instructed sofia and mel.

They grabbed the nipple clamps, one each, and moved to the opposite sides of tony’s outstretched arms. They began to lick, bite and suck his nipples until involuntarily they became hard, then they both applied the little alligator clips to the hard nipples. As mel and sofia begun to kiss each other just above tony’s chest they also begun to yank and pull at the chords attached to the alligator clips, pulling and stretching tony’s already sensitive nipples. I watched my two cruel slaves with a certain pride, I had taught them well.

My slaves began to run their hands over and massage tony’s body, this had the effect of getting him very excited. He was probably developing a hard-on, yet the metal bending his dick was holding it in such a way that blood could not fill his penis. The pressure would continue to grow making his whole genital area very sensitive and very uncomfortable.

"sofia make him eat you like you had to eat him" I ordered her. "Take that gag out of his mouth I don’t think he’s going to yell anymore, will you tony?" I watched him shake his head no. And mel, you sit on his stomach and stimulate that twisted little dick of his!" I watched as they took their positions, sofia sitting on his face, her thighs on the sides of his head, grinding her wet pussy into his mouth and nose and mel sitting across his stomach while she played around his groin, stimulating his balls and the head of his penis, which was pushing beyond the cock elbow.

"Now tony you are to eat sofia until she cums. While you are doing that mel will release your cock and apply another torture to it. This one will only stop when sofia cums and by the look on her face she doesn’t like you very much so you might have to work extra hard on her pussy!" I laughed and then left the room. I walked upstairs and watched the scene from the video screen.

sofia was sitting on his face, determined not to orgasm, yanking painfully at the clamps on tony’s nipples. While mel took off the clamp that was keeping tony’s dick bent and unable to get hard. Within seconds his dick filled with blood and presented mel with a huge hard-on, she smiled as she lighted the candle she kept nearby. When the first drops hit tony’s shaved dick his body tensed and strained, but his hard-on did not disappear.

"Remember, make her cum and I will stop" mel said to him. I would have to punish her later for such outbursts. tony begun to franticly eat sofia’s pussy in an attempt to shorten his torture. He was pushing his head up in between sofia’s thighs, positioning himself so that he could better access her clit, all the time with more and more molten wax collecting on his shaved cock and balls. Finally his efforts begun to pay off, in spite of herself sofia begun to breath deeply, to stimulate her own nipples and grind her pussy back into tony’s eager face. He was beginning to bring her to an orgasm, mel noticing that her time with the wax was running out, tilted the candle so that it would melt quicker and began to cover tony’s dick with a thin film of quickly hardening wax.

Finally, sofia could not hold it anymore and she orgasmed over tony’s face. It didn’t really matter with regards to the torture mel was applying, tony’s cock was covered with enough wax so that any new drops would only feel like warm, pleasant spots on the wax shield protecting his cock. I walked back to the room and blew out mel’s candle. After a few moments, when all of the wax hardened mel pulled of the wax cast off tony’s cock.

"See the pleasure you can bring to others, even through your own pain?" I asked him. He nodded slightly. I could see he was exhausted.

"Time to sleep, it’s late, the girls will now take you to your cage where you will await for the other two stages of your initiation. You will find some food there and a can for you to empty yourself, if you need to. Will you allow the girls to take you there or should I call my male slaves?" By the look of him I decided I did not need any other help. Once the girls undid the straps and cuffs that were holding tony in place he nearly slipped to the floor. Stumbling, they led him to another room that held various cages and boxes. They put him in the cage they had chosen for him previously. In a touching gesture, sofia handed him the wax cast of his dick so that he had something to play with overnight and locked the door to the cage. They left a small light burning so that he could find his food and water, once he regained enough strength. They locked the door of the room and the rest of us returned upstairs to rest in anticipation of tomorrow.

I couldn’t believe it! There I was locked up in a cage, all my muscles sore and my skin burning, cuddled up with a cast of my own erect dick. At first I thought I was just going to die in that cage, but eventually as my body rested, I ate the crappy food and drank the water that were left for me in the corner. My strength replenished, I began to think about my situation. What was I doing here? What was going to happen tomorrow? Would they let me out tomorrow as promised? These questions were troubling me but not nearly as much as what has already happened, not only physically, the welts on my body were a clear reminder of that, but what has happened in my head. Towards the end there I was doing exactly what they told me to do. I was OBEYING the Mistress. Was I just a slave underneath? Have I just kidded myself for so long? I fell asleep thinking it all through, at moments terrified at how much the whole episode was exciting me.

I was woken the next morning by cold water being tipped on my body. I saw Sofia standing there with an empty cup in her hand and a self satisfied look on her face.

"Get up you pathetic excuse for a human being! Your initiation is about to begin. If you thought yesterday was bad, today is going to be a nightmare!" She laughed at me, but instead of replying or defending myself I just followed her into another room. In this room there were several strange looking pieces of furniture, but thank heaven no cross! My aching arms could not withstand another day on that thing! Instead there was a leather covered wooden horse like the kind we had in high school but not as tall, shorter and a bit broader. Attached to the horse were plenty of different cuffs and leather belts, obviously for fastening people onto them. In the corner of the room was a huge mattress, covered with plenty of cushions and pillows laying about.

"Are you going to cooperate when I secure you to this or should I call for some help?" Asked Sofia pointing to the horse thing. I thought of how stupid she was. If I could do anything I would have done it by now so I just merely shrugged. She must have realised how resigned I was because she led me to the horse and with a satisfied look on her face she positioned me on it so that my back was exposed and she begun to fasten my hands to the legs of the horse. I will surely get a back whipping, I thought to myself, and a paddle on my ass again. I did deserve it though, I was the one to sign up to this, even asking for photos! Legally they had the right to do this to me, I signed all the release forms! Next time I will be reading the small text! Oh well, hopefully the Mistress will not punish me too much. And some of that shit was enjoyable yesterday, besides the pain, I did cum, and so fucking hard too!

When I was securely tied up and Sofia left the room I had that feeling again of really how vulnerable I was. Any one could come here and do what ever they want to me and I could do nothing about it! And this time I let them do it to me, I just followed like a sheep and let them tie me up. This was so against my nature, at least last time I could do nothing about it having been drugged. Maybe I was becoming a slave? Maybe all it took was a couple of days before they could break your spirit? Not mine! I am tougher than this! The door opened and I heard two sets of footsteps, then Mistress spoke.

"Good Morning tony, I see you are all ready and waiting for the humiliation you are about to experience. Good, I knew you would be a good material for a slave, you learn quick. First of all, I advise you to relax, we are going to perform something on you that most men find rather uncomfortable, we will shave you. If you relax and let us do what we will do anyway, you will feel no discomfort. If you try and prevent us, we will relax you anyway with the help of some medication and proceed with what we want anyway. Without the medication the experience will be much more pleasant for you. What will it be?"

I was stunned. These people were going into my most private parts, somewhere nobody has been before, and they will humiliate me by shaving me there. I haven’t even had any medical problems that required a doctor to look there, now I will have these perverts violate me like that! But what could I do, get drugged and then God knows what they will do to me? I mumbled an OK and tried not think about it.

They must have had all the shaving implements all ready in the room, I just did not see them when I walked into the room. I felt my ass cheeks being spread apart by Sofia on one hand and Mel on the other. I tried to turn my head to watch what they were doing to me but I could only see the three women gathering around my open asshole. I watched Mistress Gertrude standing there soaping up a shaving brush, she did look like someone I would not try to annoy too much.

She was in her late thirties or early forties, tall and slim with a slightly muscular build. You could see she kept herself in good shape. Her body was taunt and looked really sexy under her leather dress, which was short enough to reveal her great legs. On her feet and legs she wore over-the-knee, high heeled, black latex boots that accentuated her shapely legs. I think if I just saw her silhouette it would drive me crazy with desire, but her face was very pretty too. She had blonde hair and blue eyes, and although she didn’t look like an eighteen year old anymore, she was more attractive than that, with a few lines around her eyes but so much more elegance and certainty about her own beauty. Yeah I could fuck someone like that, I thought to myself and then the cold feel of the shaving brush on my anus brought me back to the reality that I didn’t really have much say about who I was or wasn’t going to fuck. I was just a plaything of my Mistress, hers to do with as she desired.

I felt the brush against the skin of my ass, my ass cheeks all the way down to my balls. It felt kind of pleasant, once you got used to the feeling of having the ass spread so wide. I turned around and watched Mistress soap my ass, she felt someone watching her and looked up at me. She gave me a small smile and then I felt her cool hand grab my balls, play with them momentarily and then move her soaped, slithery hand onto my hardening cock. She began to jerk it smoothly up and down with one hand as she continued to lather up my ass. This was really good. I don’t think I’ve ever felt similar sensation. This feeling was so relaxing, I soon just rested my body on the horse I was tied to, closed my eyes and just enjoyed the feeling.

"Look at him, acting like a dog that is getting his share of attention," laughed the Mistress. "Well enough of that, lets get you nice and shaved." The feeling of the brush was gone but her other hand never left my pulsating cock. Suddenly, I felt something else touch my ass and move smoothly outwards. Ahh, so they’ve begun to shave. This sensation was different, it didn’t hurt but it wasn’t as pleasant as the brush, it just made me feel uncomfortable. Mistress Gertrude stopped playing with my cock now and concentrated hard on the task of shaving. I looked around at her face which was looking intently at my anus. She shaved, washed the razor in a small bowl beside me and then shaved again. Then she stepped away and surveyed her work.

"Wash him slaves, and then moisturise him for me. We don’t want any shaving rash there, do we tony?" she laughed. I felt warm water being poured on my ass, my cheeks being spread and that whole area being washed and rinsed. It felt very strange to have these women looking and their hands touching such a private area, especially now that it was all shaved and bare. It probably looked like one of these chicks on the porn photos, all clean shaved and hairless. I was feeling embarrassed now with Mel’s hand putting something wet and slimy all over my asshole. At least whatever she put on was relieving the slight itching sensation I was beginning to experience. Her smooth hand was rubbing my ass hole, moving up and down the crack of my ass, all the way to my balls and onto my ass cheeks. She was massaging it in with both of her smooth cool hands. Then, I heard Sofia left the room. She returned a while later with a trolley with a large screen TV on top of it. Mistress Gertrude spoke, as I felt Mel’s finger begin to dart in and out of my asshole.

"We will let you see what your ass looks like, all shaved and bald. Slave sofia, set up the TV and the video." Sofia turned on the TV and positioned it so that I could see the white static right in front of my face. That must be part of the humiliation to show me my ugly butt, all vulnerable to their power, I though. I felt Sofia move behind me and hook up some cables and what must have been the camera to the TV. I watched the screen as a poor quality image appeared on the screen. The Mistress moved in behind me too, got hold of the crappy camera and focused it on my ass. Well, I hope they were happy with themselves, right in front of me on a big screen there was my shaved ass hole. It was red and was already showing the signs of an ugly shaving rash. This was so embarrassing and humiliating, that I just laid my head down in silent protest and closed my eyes.

"I would keep on watching tony, if I was you..." I heard Mistress’ voice. "You are going to see a very private side of yourself, or should I say INSIDE yourself. Have you ever watched a dildo cam?" I turned around sharply, shocked. They wouldn’t! But yes they would. Mistress Gertrude smiled as she held a huge dildo with a little light and a camera inserted into the tip of it. That’s why the picture on the screen was so bad, because it was filmed through the dildo cam all along!

I tried to clench my ass cheeks together but a set of hands was holding them apart as right in front of me, I watched another set of hands continue to massage my ass and stick fingers in and out of my anus. I then saw the whole picture move towards my anus, the fingers moved away and the camera stopped just an inch in front of the entrance. I tried to protest, squeeze my sphincter muscle, but to no avail. The hands held my ass cheeks apart as the dildo moved to my anus. Because of the cream they were putting on it previously, my ass hole was all ready to go. I felt this thing begin to stretch my virgin anus and move a little in and out slowly wearing down my resistance and relaxing the sphincter muscle. All I could see in front of me was this wet looking thing sort of like a moist cave, but you couldn’t see much further than a few millimetres. That would all probably change, once they begun to dildo fuck my ass properly. And they were going to!

I was feeling so humiliated, I couldn’t believe that someone was fucking my ass and I was seeing it right in front of my eyes! They were having fun with it too. I could hear them talk about "fucking it harder", "twisting it" and "letting him see deeper inside of himself". The dildo was now being pushed all the way up my ass. I could feel my sphincter muscle being stretched to its limits. It was such an uncomfortable and painful feeling, this massive thing being thrust into the depth of me. I tried to close my eyes to shut out the vision of the inside of my ass hole, all dark and red being filled and filmed right in front of me, but with my eyes shut all I felt was the thrusting and the stretching and the movement inside of me. So I watched that screen and nearly cried because I felt so small, so helpless, so insignificant to these three women who were penetrating my ass.

Finally they had enough. They were laughing now at the dildo they pulled out and shoved right in front of my face. They started to remark at how dirty and unkempt my ass was. How I don’t know how to take care of myself. I was so ashamed. I have lived my life up to then thinking I was this God, that I could do anything, and suddenly this world was shattered. I am lying tied up, with my ass shaved and a dildo I have just been fucked with near my face and three women laughing at my lack of personal hygiene. I just wanted it all to go away but it wasn’t going to.

"Clean out that dirty ass hole of his, slaves, give him an enema, tape him up and leave him to brew for a while." I heard Mistress Gertrude say. I started to plead with her to leave me alone, but one look was enough to shut me up. She then made me ask and plead TO HAVE an enema, which I did. I was beginning to feel like a slave, that all of my decisions and actions taken about me belonged not to me but to the Mistress. That she had the right to decide anything about me. I didn’t like that reality, but what could I do? So I began to submit.

A warm enema was brought into the room, and placed via a tube up my stretched asshole. I was told to hold it all in. Thankfully my sphincter muscle was getting back to normal after having been violated by that thick dildo. Once enough of the liquid was placed inside of me and it felt like my insides were going to burst, my anus was taped up by some kind of tough tape and I was left alone with this storm brewing more and more inside of me.

After what felt like hours when I felt I couldn’t stand it anymore, Sofia and Mel came back, released me from my cuffs and took me into a room that looked like a big school shower room. Hanging from the ceiling on one tiled wall were chains and handcuffs into which I was secured. My ankles too were secured into a bar that spread them apart using another set of cuffs. The sheer sensation of having my legs spread, nearly made me empty myself but I did keep it all in. Once I was secured like that and by this time I didn’t protest, One of the girls ripped the tape off my asshole which made it burn, she then moved away and told me I could let it go. And I did. I didn’t care what they thought anymore, I was just a slave like them, worse, they had some rights while I was nobody. After I finished, they hosed me with cold water, soaped me up with a big brush, rinsed me again till I felt all clean and left me to dry before taking me back to the room, all clean like a good slave.