Mistress Sarah makes Evie a Sissy 2
- 1 year ago
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Mistress Sissy Slut free porn video
Waking up, sometimes, can be rather difficult to do, especially when you know that you were d**gged the night before. Or, at least you HOPE it was only the night before. And this time, it was far worse than the first times. So many things have changed about me from the first time I was d**gged, unwittingly and unwillingly, though as I look back, I can’t really say that I am upset about the outcome of each of these times. Well, I have to admit that I was, kind of, pissed off the first time, as I never really expected something like that. But that was quite some time ago and now, well, I guess it was all for the best.
I believe that I probably should tell you the back story of this. My name, many months or maybe years, time seems so odd to me, was Mitchell. As I was growing up, I was a little overweight and as a k**, that wasn’t too terribly bad, except that, well, it caused me to get caught by my mom a couple of times. For you see, I fell in love with her underwear, from her nylon panties to the silky feel of her slips. Okay, I admit that the whole bra thing had me kind of confused at first, but when I started to “borrow” these and then fill them with rolled socks or some of her pantyhose, the idea kind of worked out better. As I look back, I think I started out being one of those transvestites, who dress for the sexual thrill that it brings. And yes, it did bring me thrills, which may have ALSO caused my mom to know it was happening. Why she never told my dad I may never know, because I swear that he would have spanked me or whipped me with his belt. Of course, now a days, you have to pay GOOD money for that!
But my mom never really punished me, though I did end up in front of her wearing her underwear on a couple of occasions and, in time, I did do my best to replace that which I admittedly ruined through my “thrill” but I always loved how they felt on me. However, that whole pantyhose thing, well, I guess that the Playboy and Penthouse picks with women in stockings was a greater thrill and shaped my preferences, though I did and do understand the thought behind pantyhose.
However, as I got older, I started to notice that if I wanted to wear the nice stuff, not just the undies but the clothing, which I was starting to enjoy doing, I was going to have to do something about my weight. Thus, it was time to join a club or something and start working out. That was a little difficult, as the good classes were practically all women and the woman running the class, Natalia, seemed like an iron clad, well maybe lycra clad would be more appropriate.
But as I watched one of the beginner classes, I saw that there were men in the class, in the back, but working hard to keep up, though one could imagine where their thoughts were on occasion, just by looking at their shorts and the tightness in them. And I do admit, there were some really good looking women in the class, and Natalia was not exactly some dog off her leash. When I went to the desk, they told me that the class had just started the week before and that Natalia would be willing to take additional students for the 3 month class. So, I signed up and waited for the first class that I would be able to attend.
Once that time arrived, I got to the gym and changed into my workout clothes. Of course, by this time, there was not a single pair of men’s boxers or briefs in my dresser. It was all cute and silky panties, most by Vanity Fair, though I did have a couple of others. And I so disliked cotton underwear that everything that I owned was either nylon, satin or some other silky fabric. I did have a couple of pairs of lycra panties, which I thought would be better for the workout class, wearing them under my shorts. A bra was, of course, out of the question. But I could get by with the panties and did.
During the first class, I thought I was going to alternately throw up or die right there on the floor. And the first thing that I thought was, “this is the beginner’s class???” And, of course, I was brought to the front of the class so that I could learn the moves, though I was off to the far side. The second class was a little easier than the first and each one after that, though not easier, I started to not feel like dying there on the floor. I also noticed that I was loosing the weight around the middle that I so dearly wanted to loose.
At the end of the three months in the class, I had not lost all the weight that I wanted to loose but I was far better than I was before the class. I also noticed that Natalia had gotten rid of the five other guys who were in the class, though I never realized that they were gone, my being up towards the front. It was at that time that Natalia announced that she was going to be doing an advanced class for those who wanted to continue. I was certainly willing to go for it and as we all filed out of the gym, I headed for the sign up sheet. It was then that I noticed that the sheet said “WOMEN” and no mention for men to sign up for it.
When I read this, I was a little upset because I was starting to enjoy it. When I read the synopsis of the class, well, I knew it was for me, though Natalia would not like it. It was being geared towards women for their bust, waist, hips and ass, with additional emphasis on thighs. In other words, all the things women (and those of us who want to look like them when wearing their clothes) want to take care of. And I knew that there was no real way that I was going to be allowed to even participate in the class, unless I could find some way to overcome my reluctance to ask.
However, when I noticed Natalia walking towards me, there was something in her eyes that told me that I was in some kind of trouble, or else, well, I might be in luck. And as I thought back, trying to figure out why she looked mad at me, I remember that she had, at some time, instead of saying “everyone” she had changed to “girls” even with me up front. And I remembered that she had been looking at me kind of funny for the last couple of classes.
“Mitchell, have you got a minute?” She was actually talking nice to me. Hell, she was just talking to me, which is something that I never remember her doing, except maybe in the beginning to ask me if I was alright or if I wanted to rest back in the beginning. She may have been a bitch all that time, but when she spoke, I started to melt, her voice was so sweet now when not yelling and such during the class.
“Mitchel, I see that you are looking at the sheet and I know that you have been doing really well in the class. You definitely wanted to be there for the right reason rather than making the girls feel uncomfortable. But as you can see, the next class is definitely geared to the girls. But I want to ask you a question, and… Well, if you feel uncomfortable answering the question, I would certainly understand. But, well, a couple of the girls mentioned that they noticed that you were wearing, well, I think Stephanie called them “pretty” panties under your shorts. Christina also noticed it and asked me. Then I also noticed that you were wearing panties under your shorts.” By this time, understandably, I was going beet red and in fear. Natalia must have seen my expression.
“Mitchell, don’t worry. All the girls know that you were wearing panties and, well, they started to wonder what color you would be wearing each time. Yes, we all gossiped, though we made sure that it was only between the fifteen of us from the class. But what we were wondering is, well.” She paused and all I could do was nod.
“Wonderful!” I looked up at Natalia, wondering what she meant by that. She looked at me and smiled. “Mitchell, then that means that you want to continue with the class, right?” I smiled, though a little weakly, and she just grinned. “You see, though we are offering the class to anyone who wants to take it, we specifically geared this one to women. But in order to have the class, well, we needed to have at least one “man” in the class and, well, you are a man. Okay, you want to appear like a woman, but that can be our little secret.”
I looked at Natalia and smiled a little more. “Mitchell, I think that I just hit on something. You really DO want to be able to look like a woman, don’t you?”
I finally got my nerve up and replied, “For years I have wanted to look better in my clothes. I don’t want to go all the way, mind you, but I would love to be able to look the part!” I noticed, as I spoke, that Natalia was not only paying attention to what I said but then was waving over a couple of the women from the class. In fact, it seemed that the entire class was coming over. I started to get nervous and started to really blush!
“Mitchell, let me tell you something, sweetie. You are among friends. In fact, I think that between the class and, well, these fine women here helping you out, you will be able to fit into whatever it is that you want to fit into. But the question is, Mitchell, just how willing are you? Because, I have to tell you, some of these nice women have some really ‘interesting’ ideas on how to make sure that you do what we all kind of thought you wanted.” I looked over towards her face and saw that familiar, evil, smile on her lips and when she leaned over to whisper in my ear, she just confirmed what I thought she meant.
“Sweetie, does the word ‘slave’ mean anything to you?” I turned, looked into her eyes and nodded. “Then it will be interesting to see which of us ends up making you their own, since just about all of them have their claws out for you… Including me, sweetie!” All I could do was… GULP!
That afternoon, all of us, went over to the little “health bar” and took over the little room. It was there that I finally, with a good deal of coaxing, told them all about my love of women’s underwear, that developed to clothing and the like. I did my best to AVOID talking about ALL the items that I owned, like a satin French Maid Uniform. Well, actually three of them, with matching petticoats and ruffled panties. I did talk about stockings as opposed to pantyhose, my inability to walk in something less than four inch heels (I walk like some drunken sailor in three inch or less heels was how I put it) and that I would dearly love to find some pretty red undies besides a bra and panties.
Basically, I noticed that the women there were trying to figure me out as I was trying to figure out what it was that they wanted from me. Some of the women left and I was not totally sure if that meant that the novelty had worn off or what. But through all of it, Natalia didn’t say a single thing nor ask a single question. And about three hours later, there was only Stephanie, Christina and Natalia with me, with Natalia finally asking questions. But when they all looked at each other, I could tell that something was up.
“Okay Mitchell. All the little “wanna be’s” are gone. Oh, I can tell you that each of those women will not only help you in some manner or fashion with your ‘transformation’, if you want to call it that. However, I guess that you need to know a couple of things, especially since you kind of understood my meaning earlier. Because from this point forward, you are going to be learning many little things and experiencing a good deal of things that, well, no ‘real’ man would be willing to experience. Oh, there are ‘real’ men who are submissive as hell and even want to become a slave to either a woman or a man. There are even cross-dressing males who would enjoy giving up control for some period of time.
“However, this is one of those times when you have to make a decision that will affect not only your immediate future but, well, in this case, the remainder of your life. And it won’t be to just one of us but rather to all three of us. And your natural submissive tendencies will be brought out and expanded upon. You will be expected to obey at all times, without question. If you fail to do so, you will be punished. You be a good little, well, girl, and you will be rewarded. But now is the time when you have to think about this and make your decision. You will have until, I guess, tomorrow, to think about it. And so that you know, you have to say ‘no’ rather than say yes. If you come to us and say yes, that is fine. If you say no, that, too, is fine. But if you just don’t do anything, well, that means that we are going to have to do this the, well, hard way as opposed to the easy way.”
With that, the three of them left, with Natalia handing me a card with a number and address on it. I sat there, looking at it for quite some time. I finally got up and drove home, running it all through my brain, trying to figure out what on earth they meant, since, well, I wasn’t sure if I wanted it the “easy” way or the “hard” way. Hell, I wasn’t even sure if I really wanted it, whatever “it” would end up being. All I know is that I could not really sleep, thinking about what it was that I was being offered. There was so much to contemplate and no time to really grasp the entire list of consequences if I went along with them. I finally fell asleep, thinking that maybe I should pass on the idea, since part of me was scared, though there was that quiet little voice in the back telling me to take the offer…
Well, things always turn out the way they do for a reason. And sleeping through the whole next day seems to have sealed my fate!
I woke up, not really realizing that things were a little messed up. I was tired but instantly realized that there was something really wrong, starting with the fact that I could not move or speak! Well, I could move my head a little but my arms and legs were going nowhere and I saw something on my chest that, well, I knew were my glue on breast forms. And they seemed to have been glued in place. I noticed that I had a gag in my mouth and that, with a little work and exploration, I realized was a penis gag. I could also feel, with my fingers, that I was wearing something around my waist and chest and something was also along my legs. When I tried to move my feet, I realized that I was wearing shoes, though I could not make out which ones, or if they were even my own.
I also noticed some minor discomfort in my crotch. I know that there had to be something inside my ass, since I had actually tried butt plugs but this felt different. And the discomfort didn’t stop there, as I could also feel something around my cock. I realized, without even seeing it, that I was wearing some form of chastity. I also noticed that it was NOT comfortable! But I could not do anything about what had happened to me because there was no one there to, well, complain to. But I did start to notice that above my head was a long panel of mirrors and with a little effort (wearing glasses is such a pain!) I could start to make out some detail of what had been done. And what I saw on my cock worried me. I had never seen a metal chastity that covered everything. But I also noticed that, well, there seemed to be something missing between my legs. I could make out the chastity but I could not see my balls down there. And my cock seemed to be stretched between my legs and pulling on something. Then I heard a door open and the distinct clicking of stiletto heels on the floor.
“Ah, I see that sissy is now awake! I am so glad to see that you are now finding out what we meant by the ‘hard’ way. And we really were kind of hoping that the d**gs we gave you during the afternoon talk would take effect. And so they did.” Natalia looked down at me and kissed my forehead.
“So that you know, even if you had said yes, you would have ended up like this at some point during the week. It just goes so much simpler this way. Besides, it gives our male slaves something important to do, especially since one of them hates wearing the ‘sissy’ uniform on a weekly basis. Actually, all of them hate it!" Natalia then delivered the bad news to me.
“So, sissy, I guess that you are curious as to what we have done to you, so far. Well, I guess that you should know that your cock has been locked into a very special chastity sheath. It is PERMANENTLY attached to your cock, both at the base and right behind the head. It is designed to pull it between your legs and locks into the vibrating dildo that will remain in your cunt 24/7, coming out only for two events. One is your daily bathroom visit and the other, well, when your cunt gets fucked, either by one of our dildos or else the male slaves are given permission to relieve THEIR sexual tension.
“Right now, you have been fitted with a nine inch long and two inch thick dildo. The charge for the system lasts about 36 hours at the medium setting. In time you will be brought to the three inch thick dildo. But rest assured, you will always have your constant cunt companion inside you, reminding you of your place!” Natalia took over my tale of woe.
“So, sissy, there are many things that you will need to know as you learn your duties. First of all, your obedience is expected and assured. Between the collar and the chastity, you should know that, well, we can make your life rather painful.” Natalia picked up a riding crop with a small box at the handle. When she pressed the blue button, I started to feel the vibrator in my ass start to work. It didn’t take but a second to enjoy the sensations. Then she pressed it again and it stopped.
“Pleasure is simple, but so is pain.” Red button and suddenly I start to arch my back straining against the straps as my cock started to feel intense pain. If it were not for the gag, I would be screaming and certainly begging for it to stop. And even though it only lasted for two seconds, it certainly felt like longer.
“Pain is administered for disobedience. All three of us can give you pleasure,” blue button again, “or we can give you pain for disobeying one of us!” I waited in horror as the red button was pressed and this time, four seconds of pain was delivered. “I am certain, sissy, that pleasure,” blue button again, “is preferable to the other thing!” Natalia then reached behind my head and removed the gag. “Don’t you agree, sissy?”
“Yes, I agree…” Red button and I was off to the screaming, as this time, it lasted for a full ten seconds, with me begging for it to end. Natalia looked down at me and asked, “do you want to try that again, slave?!”
“Yes, Mistress Samantha! Sorry, Mistress Natalia, I meant to say that I agree, Mistress!” The blue button was pressed again and I let out a little moan.
“Gee, sissy, if I didn’t know better, I would say that you like having your cunt fucked with that dildo, don’t you?
“Yes, Mistress!”
“Good sissy. Well, it is time that you got up and cleaned yourself up.” Natalia started to undo the straps and cuffs holding me to the table and as I got up, I noticed that I was wearing one of my own heels. But I had to know something, since it was really bothering me. “Mistress, may I ask what happened to my ba… testicles?” This elicited quite the chuckle.
“What, you think that you need them any longer? Sissy, rest assured that you still have them. They are well hidden, though we have been thinking of removing them, as you will have no real use for them. With the testosterone blockers that you are on, they are going to be, essentially, useless. Only reason that you are going to keep your cock is, well, it is a further sign of your humiliation.”
Natalia then attached a leash to the collar around my neck and led me out of the dungeon spaces and up to the main house. Once there, we went up another flight of stairs and I was brought to a room. When she opened the door, I walked into a very feminine appearing room. I also saw a wardrobe closet that held several French Maid uniforms, including my three, as well as all of my shoes, along with a couple of other boots and shoes that I didn’t know the origin of.
“Okay sissy, you will now strip, go into the shower and clean up. When you are done, put on the red underclothes and shoes, black stockings and the red corset. Mistress Natalia will tighten your corset and you will be able to put on your uniform.”
“Mistress, where did all these other items come from?”
“Why, the ladies from the gym brought them for you. There are additional uniforms, some very feminine dresses, blouses and skirts as well as a couple sets of work out clothes. But right now, sissy, you need to get your little ass moving!” With that, off Mistress Natalia went and into the bathroom I went.
When I got into the bathroom, I saw a couple of things that worried me, like leather cuffs and chain, leather straps and a gag, all hanging from the wall. When I looked up, I saw the hook. In a cabinet, I saw the douche bag that I was certain was used for something else, given the size of the nozzle as well as the capacity. I also found the bath stuff, from a scented feminine body wash to a pink razor to body powder. I hopped in and took a shower, making sure to shave my legs.
When I looked at my chest, I didn’t see any hair and was a little worried about that. Once I was finished, I dried off, applied the powder and entered the other room again. Mistress Natalia was already there, holding her riding crop with her finger on the red button. Something in the back of my head, probably from reading about such things and situations, made me immediately fall to my knees and look at the ground.
“Gee, you aren’t as stupid as you were a few minutes ago. Get up and get dressed!”
I got up, starting to wrap the corset around my waist and chest, giving it a light cinching. I then sat down and pulled on the red ruffled panties with black trim, the black seamed stockings and the red, 6 inch stiletto heels. When I was done, Mistress motioned me to come to her and turn around. In moments, the corset was tightened severely and I could see that I had lost a good deal of waist. But for some reason I didn’t think it was all the work outs and corset that got it that tight.
“Okay sissy. Now we have to see what kind of skills you have with applying make up. So, there it is. I want you to make yourself look as feminine and pretty as you can. Don’t worry about wearing your wig for right now. I want to see what we have to work with first.”
“Yes, Mistress!”
I immediately looked at what there was on the table and found the foundation. I touched my face and it felt smooth in all the right places. So I dabbed the foundation and then started to blend it on my face, bringing it around the ears and down along my neckline. Once that was completed, I picked up the false eyelashes and proceeded to put them on, followed by some additional mascara. It took me some time but I finally managed to do something with my eyelids and eyeliner and finally worked on the blush and lips. Once I was all finished, I looked in the mirror and realized that I looked like hell. Mistress Natalia looked at my handiwork and laughed.
“sissy, the only things that you did right was the foundation and the eyelashes. Everything else, well, you put it on so heavily that you look like an UGLY drag queen!” I had to admit that what I saw, even that sounded like a compliment. “Sorry, Mistress Natalia, I haven’t had a great deal of practice.”
Mistress Natalia laughed again. “Oh, I can see that. Take this cream and remove everything and we will work on it together.”
I cleaned up and started from scratch, working in sync with Mistress. She would do everything on the one side of my face and I had to make sure I duplicated it. As I worked and got better, I started to feel the dildo working it’s magic inside me and I eventually let out a moan of need as I could feel something building inside me. Of course, that was INSTANTLY corrected when I felt the pain in my cock as the torture device worked on me for another five seconds! Then the dildo started working on me and the process began all over.
After about 30 minutes of work, Mistress Natalia declared that I seemed to have it figured out and I was then made to put on my red satin maid’s uniform. This one had the black lace trim and the petticoat was black with red trim, giving everything a delightful contrast. Once that was put on, a leash was attached to my collar and my day was set to begin. I was brought back to the main floor where I saw that instead of just the three women who I woke up to find standing over me, there were two naked men there as well as several women, not only the women from the work out class but several others and all of them looked at me and smiled.
Each of those smiles said only one thing to me. What it told me is that the things that I had only fantasized about, as I saw the full and erect cocks on the two naked men and knew that I was going to be, in witness to all of these other people, rather intimate with them. I was scared and yet, in a small corner of my brain, I could hear this voice telling me that it was something that I wanted and that I would, even without the fear of that device on my cock, suck them and hopefully do a good job of it. But before that happened, Mistress Natalia stood me in the center of the room.
“sissy, hold up your petticoat and the skirt of your uniform so I can show everyone your nice little obedience device.” I lifted my uniform and Mistress Natalia pulled my panties down, exposing the chastity device and it’s little box.
“Ladies, this is a nice little device that guarantees that sissy obeys. The original, called “Dream lover 2000’ was developed a couple of years ago and only worked on the chastity device itself. The PRO model was the better version and it could not only be programed for several little discipline settings but also would tell you if the sissy tried to take it off or if she started to get aroused. If these things happened, it would send a little pulse to the penis encased in the chastity to remind them that what they were doing was naughty. And it would also work remotely, if your little sissy lived outside of the home. This one, however, is their newest model and, well has many other wonderful options!”
I was then made to turn around and bend over, showing everyone the dildo that was locked into my ass and HOW it was done.
“As you can see, the newer model also has an attachment for a vibrator. There were three sizes available but we only will be using two of them. One is two inches thick and nine inches long and the other is three inches wide and only 8 inches long. It is shorter as it will help to torment sissy and her little prostate, practically milking her on a daily basis and making her rather, well, slutty. Of course, it too is controlled by the same box. And to make sure that everything stays out of sight, the chastity connects to the vibrating dildo so that the cock stays between the legs and the dildo stays inside the sissy’s cunt!”
I waited as I suddenly felt the dildo start to get even more intrusive and I could feel my cock strain in the chastity and as I moaned, I fell to my knees as the torture device shot me for another five second jolt and I screamed and begged forgiveness, crying the entire time.
“As you ladies can see, arousal without permission tends to bring pain and punishment. Such a wonderful device for a sissy to learn obedience, isn’t it?” an entire chorus of “yeah” or words to that effect filled the room. Mistress Natalia leaned over to me, “get up, sissy and put your arms behind your back!”
I immediately got up and did as I was told. Instantly, I could feel my wrists being bound behind my back with leather cuffs. Then my elbows were pulled back, causing discomfort and pain as Mistress Kimberly worked them as close together as she could.
“Oh, in time, I will get these touching and then you will be a true little bondage slut, sissy!” she whispered into my ear. “Kneel!”
I fell to my knees and the first man was brought before me and his cock looked like it hadn’t cum in weeks, though I really had no idea what that might look like. I just noticed that he seemed to have a longing in his eyes and somewhat blue scrotum of the “blue balls” fame and legend. And as Mistress Natalia started to order me to suck this cock, I had my mouth opened and licked this cock from base to tip, wrapped my lips around it and started to suck it like all the porn I had seen on the internet showed me that cocks got sucked by pros.
And as I did this, I could feel the dildo working inside my ass and I was starting to enjoy the feeling of two cocks inside me and started to moan with pleasure as I felt my head grabbed and the first load of cum was shot into my mouth....
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