Tag: Sissy Maid Stories

Sissy maid training Rob

Sissy maid trainingI think I might have a new sissy go play with. Her birth name is Rob but I’m thinking of a new and more appropriate name. She is an eager, sweet, sissy with a baby face and a head of beautiful light red hair. I have already bought her a sexy maid uniform and a slutty hoe dress to wear when going out. Like right now, she’s face-timing me as she sits in a park. Dressed like a good slut and sucking this stranger’s cock for “tribute” and confirmation to what a good sissy slut she is. The stranger had his fingers in her hair using her throat like it’s a flesh light. My sissies eyes watering and making her mascara run as she gags around this strangers cock. It’s so much fun, she is almost like a puppy. So eager to please even while being abused.  I can’t wait to see just how far I can push her and how much money I can make by making her my whore.

Sissy maid training week 2

Sissy maid training

My husband is doing well with his maid training. He is learning in more detail how I like things done. We’ve been married for a while but typical guy never paid any attention to how things were being done. This irritated me a lot at first, and I have kept him in the cock cage. He hasn’t protested but I hear him with morning wood straining….ha ha ha ha.
I attached a fun furry tail to a butt plug. I thought it was hilarious and humiliating to put a butt plug up his ass then a tail on it. Watching him walk around the house is just pure entertainment.
Every once in a while I will make him bend over in front of me so I can pop it out then pop it back in. His little cock gets so hard, pushing out from the cock cage like an overstuffed sausage. A week and counting… I am wondering how long it will be until he comes to me, begging to have the cock cage removed. I haven’t thought about removing it so I think it will be a while.

You are my toy and I am your Goddess

Sissy humiliation ClarissaI think my name Clarissa should be added to a deities list, because I am a master at sex with my beautiful and bountiful body. My breasts are voluptuous and my ass is round and rock hard back side can drop up and down to make any man cum in minutes. My mouth is a wet hole of luxury and finesse. I know just how to suck a mans dick, where to flick my tongue and how fast or slow, how hard to grip when to slow down, when to speed up and exactly what to do to make it rainy sticky sweet cum from that tip. I can be your fantasy and hook you with just one smile and look from my hypnotic eye, and after I hook, line and sink you, I will throw you away and move on to the next. Why? Just because I can. I am a goddess, a goddess of love and sex and deserve to be worshiped.

Sissy maid training for hubby

Sissy maid training

I have decided to train my sissy hubby as a sissy maid. I got him a maid outfit complete with stocking, panties, a bra and a little maid hat. I told him he would be wearing this for training and I would decide if it were to be his standard uniform when in sissy mode, so to speak. I hand it to him and point to the bedroom for him to change.

When he comes out I laugh at what a candy ass pussy bitch he looks like. “Oh what an interesting sissy maid slut you make, let’s get you to work you faggot.” I said and he didn’t seem to know where to start. “What’s the problem?” I asked and as I thought, he didn’t know what to do. I said simply to work from highest to lowest.

A few hours later he came to my den where I was working and told me he was finished. “Get on your knees until I come back from inspecting it.” I said to him “there was good and bad news. Good news it isn’t horrible, bad news is you didn’t try that hard. I think until I get a better effort, you will be in a cock cage. As a reward for a good first time effort I am going to let you lick my pussy.” A grin came across his face until I said he was going to lick my pussy after I’ve put the cock cage on.

He loves licking my pussy but of course the cock cage made it uncomfortable. He flicked my clit with is tongue and slid 2 fingers inside me, I had been horny all day and relaxed into it and came all over his face. He looked like a glazed sissy donut.

Next time, he learns what else a sissy slut in training needs to know. And why he suddenly has a tail?

Tease your little sissy cock

I am so sick of dumb cocks. Its not rocket science and fucking in space. Really, If you have a penis and do not know how to use, please do me a favor and come to me for a sissy training session. If you have a small dick, cum to quickly, fuck like shit or just cannot hack it like a man, I am the solution to your inefficiency. I realized I have so many clients that really should have been born with pussies because they just cannot hack it in the world of cocks. I train my little bitches to bow, bend over, humiliate and beg for my favor because I am the master. The master at making them my sweet tittySissy humiliation Clarissa sissy maids, naughty sissy bitches and little cunt lickers for my satisfaction. I can make even the manliest wannabe man my little cunt whore and he will like it. I am so proud of them. Good little bitch, good.

From Not to Hot, my Sissy project…

I have this awesome little sissy la la that I took on as a charity case. I cannot belive how far my fruity little tooty has come in the short amount of time that I have been sponsoring this little fairy queen for. I suppose that I could explain how sad and pathetic Sissy was when I found her. She was so sloppy looking. She didn’t know how to put her make up on and she was dressed like a bad character from a Disney movie. When I found her Sissy was sitting in a jail cell drunk off her ass and had been taken advantage of by all of the other inmates. Sissy was crying like a little faggy cry baby.

Sissy humiliation Sissy

 

I took Sissy into my home and showed her how merciful a goddess like me could be. I made Sissy clean up and take care of those assets, even that little fairy tiny tinker.  I gave Sissy some food made him sober up and I even helped Sissy get off a couple times. I put Sissy through a few tests before I really invested too much into her. I gave Sissy for explicit instructions on how to lick my pussy, jack off with my favorite butt plugs in her asshole. I showed Sissy how  Il like her to bend over when she is wearing the outfits I have picked out for her for our play dates. So far Sissy has done really good and I am very pleased with the outcome. Here is a before and after picture of Sissy. The little fairy fag I met at the jail compared to my Princess poopy pants.

Sissy humiliation Sissy

It is amazing. I can not wait to teach Sissy more and turn her into my favorite fairy faggy princess, I will ensure Sissy stays prissy and does not go back to her old ways.

Sissy maid training Clarissa

Dick humiliation and cock play

Sissy humiliation ClarissaTrying a new toy out on your favorite sissy botch’s ass is so fucking hot. I ordered a box of new toys which included a strap on dick, a bunny vibrator with an extra stong motor, a few cock rings and this ass plug which vibrated and had little silicon spikes around the rim for a little painful pleasure. My client showed up fr his nightly humiliation session and I immediately told him to get on all four and spread his pretty little ass cheeks for madam. He did so like a champ. I was feeling a little frisky, so I slammed that plug up his puckered little asshole enough that he gave me a little whimper. That made me wet fast. I love to hear my bitch, whine, cry and in pain. I then put on my strap on and face fucked him until he was so hard he had purple balls. I put my cunt up to him let him lick it until I came all over his face, I gave him a fake pussy to relieve himself into and then I sharply removed his ass plug and told him what a good little sissy bitch he had been.

Sissy Bitch

Sissy maid stories

I was shopping today for a new maid uniform for one of my clients and it got me thinking that I need a new sissy bitch to lick my leather boots. They have not been cleaned in some time and are due for a good licking. I also got to thinking how much not only my boots need cleaned but so does my asshole. I really need my new bitch to have training in several areas. I started checking off what I wanted in my head and I decided I really want someone who can lick like their life depends on it, someone who is not a giant crybaby and wont be a little bitch when I slide my fake cock into their asshole, I want someone who can lick pussy without needing any air because I do not like giving breathing breaks. I want a little bitch who is going to obey my every command without question. And if they do disobey me I will make them wish they had not. I have many over-sized cocks to stick in your orifices as punishment.

Sissy better be thankful!

Sissy maid stories

I am still so stuffed from thanksgiving! I had so much fun! My pussy is still dripping from being stuffed by a big thick black cock! Oh god he filled my honey hole up with his thick cream. Sends chills down my spine just thinking about his big hard cock stuffing me like a thanksgiving turkey. Pounding my honey hole making me so wet. His hot sweaty body against mine. He was so deep inside of me. I couldn’t breath! He was ecstasy. His dark chocolate body next to my white creamy skin drove me wild. Every now and again I would hear some slurping sounds and smile. My little cuckold sissy maid was there underneath us, slurping up my puddle of pussy juices off the floor while he rubbed his little locked up clitty. His tiny little clitty was drooling. He was begging to taste that big chocolate cock. It was thanksgiving and I felt like being giving. I let my little sissy maid suck that chocolate cock till he blew his creamy gravy load down my sissy’s throat!  

Sissy maid stories: the cock, the cage, and the plug

Sissy maid stories

I’ve been having so much fun training my sissy maid. It’s becoming my favorite activity next to fucking you.

Of course with our new little toy you’ve gotten a lot more attention to your cock.

Like right now. I was enjoying the site of our little sissy maid on her knees. Wearing a latex maid outfit that left little to nothing to the imagination. Her little bitch clit throbbing in its cage as it tries to get hard. I giggle as I watch it, poor pathetic little thing.

Her cock was in your mouth.  She was fucking her own throat with such vigor that you couldn’t help but lean back, your eyes rolling into the back of your head. A pool of spit on the floor between you, our sissies tears ruining her makeup and her bright red lipstick was smeared all over your cock and her mouth.

I pressed the button to the remote control vibrating jeweled anal plug in her pussy and watched her quiver. She moaned around your cock making herself gag and try to pull off of your cock. I giggled as you grabbed her by the hair and forced her back on. Fucking her mouth with short hard thrusts until your groaned.

She was quivering, her hands open and close, Gagging and choking around your cock as you force your cum down her throat.

When you let her hair go she pulled back, coughing and gagging. Tears streaming down her cheeks as she gasped for breath. When she got some control again she swallowed hard and looks up at you. “Thank you sir.”