Sissy Maid Slave Stories

Sissy Maid Slave Stories




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Sissy Maid Slave Stories
This is a continuation of the story of Becoming a Sissy Maid .
As the months passed and my wife kept me locked in chastity more and more for longer and longer, my desire to be Zoe, her sissy maid , grew every day. Luckily, my wife “made” me be Zoe every weekend and sometimes a time or two during the week. I loved every second of it.
My wife would peg me when she deemed it a special occasion or I earned a reward. After a few times she told me she had to buy a bigger dildo because the old one was getting too small for my sissy pussy. I was nervous to take a longer and thicker dildo, but was pleasantly surprised by how much better it felt. 
On most days she required that I wear a mouth gag that was shaped like a penis. She made me alternate between a short gag and a longer gag, saying the short one would help me learn to please the head and the longer one would help me with my pathetic gag reflex. If I struggled with the long dildo gag, she would force me to practice on her strap on and if I gagged or complained she would punish me and call me ungrateful, saying, “real sissies love sucking cock and would never gag.”
Sucking on the dildo was a little weird to me and made me question my manliness, but when she demanded me to suck on it and called me her sissy slut I would suddenly have a passion for it. At first I just had to tell myself, “it’s not gay if your wife is forcing you to do it.” Eventually, as my gag reflex and skill improved, I started enjoying sucking her strap on and receiving complements from my wife.
My cleaning skills were vastly improved as well. I knew far more about cleaning than I ever expected I would or could. I started buying new cleaning supplies and really getting into it. I knew the better I performed as a maid, the more likely I would get to be a maid. Over time it kind of became a hobby and challenge to clean more and better. Some how there never seemed to be an end to the cleaning and maintaining the household and that was fine by me.
Everything was great other than our sex life. At least that’s what I would tell my guy friends because my wife and I never really had sex anymore. Maybe once a month she would let me out and let me have sex with her, but most of the time if I got out she would give me a ruined orgasm or penetrate her without being allowed to cum. She would tell me that denying me orgasms would make me a better maid. I got to make her orgasm all the time which I loved, but I could tell that she longed for more dick. 
She had me start fucking her with dildos and vibrators. Part of me wanted to say, “why not just unlock me and let me fuck you?!” The other part of me loved being in my cage and didn’t want to come out for any reason so I stayed quiet and followed her orders. I also realized that this dildo was so much bigger than my little dick and was pleasing her way more than I ever could.
Then one day when I got ready to be Zoe, my wife came to me with a change of plans. “Zoe, my house is clean enough today so I have something else planned for you. I owe my friend, Taylor, a favor so I told them I’d clean their house. Of course, I no longer clean so that’s where you come in.”
“You want me to clean someone else’s house? Will he be there? And who is this Taylor girl?!” I asked in a panic. I had never heard of a Morgan before and didn’t like the idea of cleaning anyone else’s house. I enjoyed my at home cleaning routine so much.
“That’s really none of your business, Zoe, but Taylor is just someone I met at the gym who has been giving me private training sessions. I offered to pay back the favor by cleaning their house. And yes, Taylor will be there but don’t worry, I’ll keep them preoccupied so you’ll hardly notice him. Now come on, grab your cleaning supplies, get in the car and let’s go. If you do a good job, I promise you’ll get a big reward.” She replied.
Ever eager to please my wife and mistress, I did as I was told and got everything in the car. 
When we got there I met Taylor at the door. I had assumed Taylor was a woman, but he was a tall, handsome man with bulging muscles. We gave each other weird looks, both clearly not expecting what we were seeing, but he welcomed us in when my wife showed him a bottle of wine and explained that she had hired a maid to do the cleaning and wanted to use the time to have a drink and get to know him better while I cleaned. 
He brought her into his bedroom and closed the door and left me to clean. I didn’t like my wife being in a room with another man, but I just assumed they would be talking about working out or something boring and the faster I got done, the sooner we could both get home. So I got started. 
After several hours of vacuuming and mopping the floors, cleaning mirrors, toilets, and sinks, doing dishes, cleaning appliances and dusting, I tapped on Taylor’s bedroom door to let them know I was done.
My wife came out and put my leash on and led me around the house to inspect what I had done. Oddly enough, she seemed to know her way around already. Overall, she didn’t seem too interested and was generally approving of everything. It wasn’t her house after all so why would she care that much and I didn’t mind because I wanted to get home.
“Everything looks amazing, Zoe. You’ve done a great job. Are you ready for your big reward?” She asked me.
“If you’re so gracious as to give me a reward, of course. But here, mistress?” I asked in reply.
“Of course, Zoe. Today, after your months of practicing, it’s finally time you got real world experience as not just my sissy maid, but as my sissy slave. Are you excited?”
I was confused and frightened. I had been practicing my maid and cleaning skills of course, but I had already fulfilled that task. The only other thing has been practicing sucking on the dildo. She couldn’t possibly mean…
“You’re speechless. No worry, I like you that way better. Come join us in the bedroom.” She said as she took my hand and lead me towards the door.
As I entered the bedroom, Taylor was sitting on the edge of his bed, naked and stroking his erect penis. I could feel my eyes bulge in shock. No way, there’s no way she’s going to make me do this.
“Zoe, when it comes to sex, my husband has been very lacking in both his performance and size. He has never even been able to make me orgasm or satisfy me sexually. Lately, he hasn’t even wanted to try and I have a feeling he’s much more interested in dick then my pussy.” She moved to stand beside Taylor, resting her hand on his shoulder. 
“Taylor here has been very interested and willing to please me and has been great at it.” She said as she closed her eyes and bit her lip clearly remembering their past exploits. “Today isn’t about me though, it’s about you, Zoe. You’ve been so good to me and with your sissy training lately and I wanted to reward you. So today, you get to please Taylor with that little mouth of yours and then with your sissy pussy.”
I stood, wide-eyed, staring at her. There was so much to process. She was cheating on me with this guy and now she wanted me to suck his dick? I’m a man; I can’t suck a dick!
“Zoe,” she started as she crossed her arms. “Don’t embarrass me! Get. On. Your. Knees. NOW!”
On instinct I did as she told me and got on my knees.
“Good, girl. Now start sucking, you dirty little sissy slut. I know you want to.”
The truth was that I did want to. I had been wondering for weeks what a real dick would feel like in my mouth and in my ass. My penis started throbbing and trying to burst out of the chastity cage that was tucked between my legs which only seemed to confirm my desire. But my wife was standing right there and if I did this it would confirm to her that I did want to.
“I said, ‘SUCK’!” She yelled as she grabbed the back of my head and pushed it towards the dick.
Well, I guess I have no choice, right? I opened my mouth and took cock in my mouth for the first time. It was much softer than the dildo but that was nice. I reached up and grabbed the shaft and started deep throating it, using my tongue to in a way I knew would feel good to Taylor. He started to moan.
“That’s it. That’s a good slut. I knew you were born for sucking cock.” She said as she leaned in close to watch.
To my surprise, she wasn’t mad at all, she was acting like she really knew I wanted to do this. Her reaction and acceptance excited me more and I got more into it, feeling his thick, throbbing veins against my tongue and his pulsing head in the back of my throat.
I felt like i blacked out. I was so in rhythm with my sucking and licking. Next thing I know I feel a surge hit the back of my throat and Taylor groaned loudly as he pulled his dick out of my mouth. I could see that it was dripping with cum as I swallowed, tasting what was in my mouth already. 
“Welcome to your new life, Zoe. Now clean up that dick and assume position on the bed. We’re just getting started.”
My new life? Well, I guess there’s no going back now.
I looked up and locked eyes with my wife. “Thank you, mistress,” I said with a smile. Then I turned back to Taylor’s cock and licked the rest of the cum off. I stood up and pulled up my petticoat and skirt as I bent over the bed with my face in the bedding.
“Now, are you ready to find out how a real man fucks?” Asked my wife.
“Yes, mistress.” I replied as I closed my eyes. I can’t wait.
Becoming a Sissy Maid: Unlocking Hidden Desires is now available on Kindle and Paperback. Read the full story of Brad, Zoe and Melissa in this 13 chapter, 136 page book.
My sexy dominant white wife forced me to wear bright red lipstick and a microminiskirt and got me high on cocaine before she called her big black boyfriend over and made me suck his beautiful huge black cock
When I saw you photo in your black lingerie I would love to submit to you for your pleasure
I would love to be made to live as a submissive sissy even though I am straight. I would like a woman to take me and strip me naked and make me slip on panties, full lingerie and so on. Discreet
bdsm, cbt, sounding, spanking, clothes pins
confession, Forced to be A Sissy
I have been trained as a housemaid and a parlour maid. I have a number of maid uniforms that I wear when working as a housemaid for a local lady. What I need now is a couple to put me to work as a female cleaner in a house or office for which they charge. They are not to pay me just tell me each month how much money they have made out of me and maybe what they have spent it on. I would of course have to do their cleaning and it would be nice if they went for a nice meal paid for out of my earnings while I was cleaning their house. When they got back they could inspect my work and punish me for anything not done to the level they wanted. They could then dismiss me after punishing me with a riding crop across my knickers and with a warning to do a better job next time or the whipping would be worse
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Sissy maid slave disciplining and training is a responsible task. For best results, it takes to have proper women in charge. Otherwise, just as with everything else in life, results will be disappointing. So what would be a good address to look for a proper sissy maid training?
The answer is simple and almost obvious for anyone into the femdom lifestyle and with at least basic knowledge about best femdom sites . I am talking about the English Mansion . Well hidden and surrounded by beautiful nature, there no better place to discipline slutty sissy slaves than here.
The best part is that sissy maid slave humiliation and torture you are about to see wasn’t planned at all. This is a typical example of a spontaneous experience often seen with women living a genuine femdom lifestyle. So before checking out more details about the femdom sissy slut scene, let’s say who are sexy Mistresses in charge.
On the left side of the first maid service photo below, you will easily recognize the proud and self-confident attitude of world-famous Sidonia Von Bork . Mature and experienced, there is no femdom scenario where she is not an expert. I mean, just one look toward her mean eyes will tell you enough, without a word spoken.
The other divine blonde lady in black nylon stocking on the right is Miss Suzanna Maxwell. You can enjoy some more of her top-rated femdom photos on her Instagram profile here . She managed to balance nudity, BDSM, and Instagram requirements very well so you will find some almost explicit pics there. So let’s get back to the scene and see what is going on here.
The beautiful, empowered femdom Goddesses are appreciating an afternoon in the Mansion grounds and waiting for their favorite drink (tea), which is finally served by a maid servant, Popette. These two dommes love that everything is perfect and there is nothing that will ruin their tea they are having on a regular basis. You will notice that every detail is perfect, even a sissy femdom sub is wearing a well-chosen beautiful satin sissy dress.
What you won’t see on the maid service photos is that the maid sissy made a huge mistake. He spilled tea into the saucer, probably because of fear and all that tension that is always present when serving cruel ladies. There is a high quality slave sissy available inside the member zone of English Mansion where you can see that moment. As you know, because of copyrights, I can’t publish it here so you will have to use your imagination at this moment. That shouldn’t be too hard because you already have free sissy boy pics representing this brutal and realistic maid training . 
The main advantage of having sissy training in a such special place as English Mansion is the fact that there are all necessary femdom torture tools at disposal to the Mistresses. It is completely up to them to decide which one they will use, or to be more precise, will corporal punishment be conducted outdoors or inside their BDSM dungeon. 
Luckily for a slave, Dommes agreed that he doesn’t deserve to waste a lot of their time so he will get his punishment right on the spot. I can bet that he thought that he will get away with a simple femdom caning punishment what would be the easiest for a sissy boi. Guess what? He is wrong, again. 
After merciless and harsh ass caning and after slave’s ass is ruined and covered in red bruises, the sexy sissy maid is about to experience something very special. And I am not talking about sissy bondage but about the other thing coming once the slave is tied placed into a suitable position.
The time has come to experience how does it feel to be in the role of a strapon slave. The best part of sissy humiliation is about to start right now. But what is interesting is that Dommes won’t get their hands dirty, especially when they are dressed so good. For that purpose, they already have a solution and it is called a strapon fuck machine.
If you are unfamiliar with how it works, I will suggest taking a look at this strapon machine slave fucking footage . It is one of the best videos in this category and one of my favorite femdom torture methods. The main advantage of this device is that pegging strapon slave sessions can last much longer than the regular anal domination ones. Also, a sissy faggot can be placed in a variety of positions with the purpose of getting the deepest possible butthole penetration.
I want to share a small tip with you that most of the Dommes already know. Take a look at the slave maid picture where he is lying and waiting for a plastic dick to enter his butthole. As you will see slave’s cock is tiny. Strange, considering that two hot women in high heels are standing right above him while his genitals are exposed. Theoretically, he should be sexually aroused up to that level where it is impossible to hide an erection. But when a male is placed into a state of great fear and uncertainty, one of the first things that will stop working normally is his cock.
This is how an experienced femdom Mistress will know is she doing a good job. A great indicator, much better than the sounds and screams slaves tends to make because every person has a different level of pain tolerance. On top of that, some of them will beg and scream because they believe Mistress is expecting to hear it. So next time when you see a maid in PVC with a tiny cock, then you will know how to interpret it.
If you are into the mistress and her sissy fetish niche, here are two more maid slave femdom from before. Check out and enjoy domestic maid slave crossdresser training photos where two kinky goddesses are teaching a slave how to behave in the role of a nasty slut maid. But also do not skip group French maid bondage and a forced maid training featuring four sissy slaves and two hot Dominatrixes.
How I would love to be enslaved and put over these beautiful English mistresses lap and hand spanks and become their housemaid slave
This stupid sissy-maid here deserves no better.
She must also be punished and eventually castrated by
these beautiful Mistresses.
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This is a continuation of the story of Becoming a Sissy Maid .
I couldn’t believe it, but I was starting to look forward to being Zoe, my maid alter ego. I found myself naturally keeping the house tidy throughout the week even in my normal male state. Cleaning was becoming second nature even though part of me thought that if I left the house messy enough my wife might demand an extra visit from Zoe.
Perhaps it was because my wife had been keeping me locked in my chastity cage for longer and longer and I had a lot of pent up sexual energy. I felt like I was able to release some of this energy into my dressing up as Zoe, even though it did feel like a long teasing session, especially when my wife rewarded Zoe by making out and caressing her body. My wife had also started demanding that I wear panties every day to be more in touch with Zoe so feeling my thongs holding down my caged penis and tickling my butthole made me constantly think about dressing up as a maid.
One day I finally built up the courage to talk to my wife and suggest that Zoe spends an extra day each week cleaning. I gave examples of all the chores that she could perform in that time such as mopping the house, reorganizing the pantries, cleaning all the house windows, etc and promised more Zoe would make her happy.
“Just can’t get enough of being my sissy maid, can you? Wow, Brad. I knew you would like it, but not this much,” she replied to my suggestion. “Alright, Zoe can come more often but only if you agree to a few caveats.”
I blushed a little at her calling out my enjoyment of being Zoe. “Alright, name it,” I tried to say as nonchalantly as I could.
“First, I want to hear you admit it. Say this, ‘I love being your sissy maid and doing everything my Mistress says’.”
Pretty easy first demand. I repeated her line as a smirk grew on her face
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