I started today ready to find some manly man, a stud above studs, and treat him to some Sissy humiliation. It’s not often I want to bring someone down but today I absolutely did. I craved to strip someone of their manliness, to tear their masculinity away, and put them in the prettiest, frilliest dress I could find. I put an hour of effort into finding the best pink pair of panties I could find, I found white stockings and a bowtie, and then I went and got my hair ties to wrap whatever hair they do have up in pretty pigtails sprinkled with glitter. Then I looked at what I’d gathered and realized I got a maid outfit, and with that, I knew I was going to give them the hottest, tightest, cruelest Sissy maid training they could possibly imagine. I was soaking wet just thinking about ruining some man forever and making him my little girl bitch. If he behaved I’d worship his cock like the powerful stud he is, but when he was bad, oh the ‘he’ word was going to be out the window entirely for the day and I was going to plug her ass with some other man’s huge dick and not let her up until she’d recited all the super important rules any sissy maid should remember to include when making up their task list for any day. Obedience, pussy licking, dick-sucking, they learn how to take a dick up the ass, they learn how to deepthroat, they learn how to drink cum from my cunt and they do it with a smile. Drop something? That’s just an opportunity to show them what they’re meant for when they bend over. While I’ll admit most of the time I’m really for a GFE kind of thing, but today I really craved Sissies and I decided that I’m about to make Sissy maid stories and they’re gonna be hot as fuck and bringing steaming loads to cover my sissy’s ass with. You want to help me bring someone down, or get torn down?
Category: Sissy maid stories
Clean My Apartment And Look Cute Doing It
- By Eliza in Best phone sex, Cocksucking phone sex, Coed phone sex, Cuckold phone sex, Domination phone sex, Princess phone sex, Shaved wet pussy, Sissy humiliation, Sissy maid stories, Sissy maid training
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August 27, 2022
It’s sissy maid cleaning time! It’s all ready for you slut and remembers I installed cameras all around my place to keep an eye on you. If I see you skip anything on your list I will have to punish you one way or another. Put on this adorable hot pink maid outfit I ordered for you, comes with a cute pink silky g-string! Perfect for whenever I wanna come up behind you and tease you with the ass resting against your pussy. Love doing it cause it makes you moan like a good slut for me. For now, I’m going to pull that string to the side and shove up your sparkly buttplug to wear for the day. Better not remove it, if I see you bend over once and not see this in place then you won’t be able to play with your clitty after this. Now I’ll just be going into my room to get fuck, but I’ll be watching. My room will be the last you get to clean but only if you are a good little sissy maid for me in the meantime.
Eliza
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Used His Sissy Maid’s Mouth
- By Daniella in Ass fetish, Ass sex porn, Fantasy phone sex, Foot fetishes, Roleplay phone sex, Sexy babe, Sexy dominatrix, Shaved wet pussy, Sissy humiliation, Sissy maid stories
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July 8, 2022
One of my playmates brought his sissy maid bitch. He has trained him very well, greeting me with his mouth to my feet. He kissed and licked my heels like a good bitch too. He was wearing lace sissy panties, the type of lacey ones I wear. He told me to use his sissy as I pleased. He just wanted to watch. I made his start by giving my sexy feet a massage with his mouth.
I made him suck every toe as if he was sucking a cock. I looked over and my playmate was stroking his cock getting it hard. He loves my sexy feet and kisses them himself. I spread my legs and his sissy bitch knew to start licking my cunt. He sucked on my clit and stuck his tongue in my wet pussy so good I thought I was going to cum, but I knew my playmate was enjoying the show so much that I wanted it to last longer. I got up and bent over and spread my ass cheeks, he started lapping my asshole like a puppy bitch and i could see how hard it made my playmates cock. He always loves fucking my asshole, he got up and stuck his hard cock in between his sissy’s tongue and my asshole. He rubbed his hard cock on both of us and my cunt dripped down my legs. He rubbed his cock all over my pussy juices and then pushed his cock in my ass. He grabbed his sissie’s face and shoved it to his ass. He got his asshole licked as he fucked mine and all i wanted was to cum. I rubbed my clit while getting fucked in the ass and i came hard. My playmate felt my pussy cum, he filled my ass with his big load. His sissy maid whore spent the rest of the time cleaning my asshole and his cock.
Daniella
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Sissy Maid Training Bitches
- By Ramona in Domination phone sex, Domination porn, Fantasy phone sex, Female domination porn, Forced crossdressing, Forced feminization, Naughty maid phone sex, Sissy humiliation, Sissy maid stories, Sissy maid training
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June 20, 2022
Sissy Maid training phone sex is one of my many talents. When I get a new and willing sissy I start out by stripping her buck naked and stand her in front of the mirror to see just how her body looks. I start by having my new sissy put on a pair of white cotton brief panties and a training bra. She must earn the right to wear shit like garters and corsets. That bitch must start at the bottom and work her ass up to that kind of lingerie/outfit. Then I tell the sissy to put on a flower print dress white socks and mary janes and her legs better be shaved! If my sissy in training isn’t acting the way I think she should I will put a chastity on her little cock and I’ll keep the key, I will threaten to throw it out the car window while I’m driving or to make my sissy bitch swallow it and shit it out in order to be able to unlock her little prick.
Next sissy will be locked up in the dog kennel I have on my back porch, and she must learn to listen and submit. I will keep her thee for punishment if she misbehaves and feed her meals in a dog bowl and only let her out to piss and shit. Once the bitch is acting right, she gets to graduate to a wig, and depending on my mood ill pick out the color and style. Whether sissy’s are ‘passable” depends on their commitment to my methods. So, taking sissy out in public is part of the training, she better be acting right so I don’t have to humiliate her in front of strangers even though she probably would like it that’s a privilege. IF Catch her stroking her cock without permission that’s grounds for the kennel or for scrubbing my floors in a g string only and a shock collar
. I’m not afraid to use the shock collar either. A sissy must earn the right to have an erection and jack her little dick to orgasm. That shit is earned by obedience and servitude to the mistress. ME! I have the divine mistress and must always be referred to that way or I will punish a sissy cunt in training! Sissy’s have no say in anything their goal in life is to please me and learn how to be a sissy little whore who does what she’s told. I also list my sissy’s on craigilist and pimp out their mouths and asses to random dudes. I keep all the money earned of course and the sissy in training goes to her knees to take cock after cock load after load of hot jizz into their pathetic little mouths not to mention offering their assholes to any guys who wants and bareback of course so their ass is just drooling sperm for days afterwards because they are so stretched out and there’s so much cum inside their sphincter. So if you are ready to be one of my sissy bitchs in training you know where to find your divine master!
Ramona
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Sissy Lover
- By Divina in Ass sex porn, Ebony phone sex, Fantasy phone sex, Forced crossdressing, GFE phone sex, Hot sexy woman, Sexy babe, Sissy humiliation, Sissy maid stories, Sissy maid training
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May 8, 2022
Sissy men love being dominated especially by a sexy woman like me. I have a sissy punk who loves dressing up in sexy latex and silk clothing. Heels and wigs every night for me.There is a different outfit for any role playing I want to do. One night he wore a maid outfit for me and cleaned he entire house. He dances and prances around the house until I give him all my attention. He always loves being up under my friends and me. He’s a pleaser and wants to make me happy by any means. He is also such a spoiled little cunt, but I wouldn’t have it any other way. I absolutely love me a sissy who knows how to behave like a good boy and a bad boy. Someone who lets me do whatever I want to him. Whenever I want. Because of that I give him whatever he wants.
Sometimes I let him dominate me to give him a little confidence then I break him down and humiliate him. As a black dominate Queen I need a man that knows how to drop to his knees and eat this pussy when I tell him too. Or wear a diaper for hours and piss in it. Or maybe I will have some of my big black friends come over and have their way with you. I need to feel like I own you baby. Can I do that with you? Have you been a good boy or bad boy? Do you want to play dress up? What color thong you would want to wear for my baby? I know the perfect site for outfits for my favorite sissy. I want you now baby, give me a call and let’s play. I am looking for the man that will satisfy himself and me. I want to create an unforgettable sissy experience for you baby.
Divina
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My sissy maid training
- By Gwen in Best phone sex, Domination phone sex, Erotic roleplaying, Fantasy phone sex, Femdom phone sex, Mature phone sex, Naughty maid phone sex, Sissy humiliation, Sissy maid stories, Sissy maid training
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April 24, 2022
What if my sissy maid training could give you life purpose? That is how I met my very own sissy slave house-pet! Zak was down and out on his luck. His wife had left him, due to not being able to satisfy her in bed and his mistress had abandoned him due to his lack of funding after his divorce. She was only on it for the money. Therefore he was at his wits end. And I found him drunk in the gutter trying to end his own life. I had a need for a maid,and hearing this pathetic man’s cry for help, I knew I could give him purpose and have a dedicated sissy slut I could control forever. My maid dressed like a slut works hard to clean my condo and I love calling him all kinds of names as he serves me in every way a sissy whore should. I gave him purpose and he gave me devotion, much like a pound puppy does when you rescue him. I’m all about recusing sissy slut whore slaves nowadays! Cum be my puppy house cleaning pet that for me to own! Sissy humiliation is one of my favorite activities in and out of the bedroom!
Gwen
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Forced Feminization
- By Ramona in Domination phone sex, Female domination porn, Femdom phone sex, Forced crossdressing, Forced feminization, Naughty maid phone sex, Sissy humiliation, Sissy maid stories, Sissy maid training, Small dick humiliation
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March 10, 2022
Forced Feminization would be both a dream come true and his worst nightmare depending on how he looked at it. Bill was known as the strongest man in town as the Sherriff, but he had a dark dirty secret. He was the town’s biggest sissy in training with Mistress Glinda. He lived every day in fear that his secret would be revealed, and he would be outed as being the little sissy that he was.
Every Friday night Mistress Glinda would invite over friends to share in the humiliation and degradation as he was forced to wear the French Maid outfit and serve cocktails to the ladies. The ladies loved to see just how far they could push him especially about his little cock. Each week after the guests left he was either rewarded or disciplined based on his behavior that evening. He understood his place and always bowed down to Mistress Glinda no matter the outcome.
Ramona
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Richard Sheets BBC Faggot
- By Rebecca in Best phone sex, Cocksucking phone sex, Domination phone sex, Erotic roleplaying, Femdom phone sex, Forced crossdressing, Forced feminization, Sexy legs, Sissy humiliation, Sissy maid stories
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January 13, 2022
The best phone sex is outing a BBC pantyhose wearing fuck whore. Richard sheets is that fuck whore. A dirty little slut who wears pantyhose and loves big black cock. Richard is such a little faggot whore who loves to get fucked retarded by big daddy dick. Look at the little faggot.
These big black cocks that fuck my sissy faggot keep the fuck out of his little pussy. The best part is big black daddy gets off on hurting little white sissy faggot. Richard is a stocking loving sissy faggot for big fucking black cocks. The only use I have for this little faggot is to humiliate him.
Richard moans like a little Beta bitch when that big black cock fucks his little faggot hoe hole. My little cocksucker admitted that he likes to beg for that cock. In fact he lets his big black daddies fuck him bareback what a pathetic little slut huh?
Rebecca
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Sissy Maid stories to live by
- By Gwen in Best phone sex, Cuckold phone sex, Domination phone sex, Erotic roleplaying, Fantasy phone sex, Femdom phone sex, Roleplay phone sex, Sissy humiliation, Sissy maid stories, Sissy maid training
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November 7, 2021
The bubbles lapped my skin as the water swooshed back and forth. I had been reading some new sissy maid stories and was lost in the thought of my newest sissy. My body was alive at the thought of my sissy Sucking the UPS driver’s cock as a tip. We had been making good progress, and the outfits He bought to dress up in had become more sissified every weekend. He had taken my strap once and had taken three weeks to come back and see me. I was sure that would be the last session we had. But this morning I received a sissy novel on my doorstep and A bottle of wine and a Bath set. We had a “date” soon, and I was crafting a plan to keep him in my care for a long time.
I had fired my part time housekeeper and the house looked like a single busy business woman, lived alone. I stepped over discarded hose and panties, over towels and lotion bottles; giggling to myself. I had added to the mess with Hiding sissies butt plug under a pile of jackets and leaving a note beside it. Sissy was going to clean my house and sissy was going to either Present herself fully, or find another Mistress, My boots and black leather outfit With the crotch cut out would set the scene. It was Sissie’s favorite outfit. A leather loving sissy who would orgasm if he was allowed to click my boots too long.
The note read: Things you need, Your butt plug. (lube or no lube) The shopping bag in the closet behind My favorite Boots and Paddles.
If you wish to submit fully to me, and give me control to lead you into true sissydom, You know what to do. If you wish to end your contract you may gather your things and walk out the back door to hide your shame, No refunds on my Mistress tributes.
It took him 15 minutes. I waited dressed with my legs propped up on the couch. Sissy came crawling with her ass in the air, one pair of panties on and a pink leather paddle in his mouth. Sissy whined at my feet like a good puppy sissy.
We would begin his sissy maid training fresh. I had new ideas from his book.
Gwen
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Surprise Daddy!
- By Amber in GFE phone sex, Large boobs, Milf phone sex, Phone sex sites, Roleplay phone sex, Sexy babe, Sexy dominatrix, Sexy phone chat, Sexy women masturbating, Sissy maid stories
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October 4, 2021
I love surprising my sugar daddy at work with a nice sloppy wet blowjob under his desk! Daddy works so hard to give me all the nice things I want, sometimes I like to return the favor by treating him like the amazing sugar daddy he is. I come in wearing a little trench coat with nothing on underneath, when I open the coat and daddy sees my perfect naked body his eyes light up. I crawl under his desk and suck his cock hard, the head of daddy’s cock touched the back of my throat and I gag just the way daddy likes. He grabs the back of my head and starts fucking my mouth hard. When daddy squirts hot cum down my throat I swallow every drop like a good little slut!
Amber
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These are my favorite “date” nights with you. I make sure to wear my slutiest dress I own. I'm almost pouring flesh out of… [more]
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