Tag: sissy maid training

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.

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.

Sissy maid training Service for Pussy

Sissy maid trainingI can’t understand girls that don’t like to eat pussy, it’s such a strange idea for me. Especially when I love it so much and I know that you love it too. You love that I have so many pretty young play things to eat, finger, and fuck while you watch us. I especially love it when I have your cock in a cage, dressed up as my sissy maid. Your hands cuffed together in front of you to keep you a good little girl as you have to watch us. Knowing that we’re enjoying each other more than you’ll be ever too. Maybe, just maybe we’ll let you join us. Let you taste our sweet pussy and let ourselves cum all over your face. But, you know what you need to do before that love. Her boyfriend is over there, jacking off as he watches us fuck each other. Maybe if you help him with that pretty sissy mouth we’d let you play. But, you can just watch too. Just remember your time is running out, you have until he cums.

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 maid training with Clarissa

Sissy maid training

Well, I found a new maid. He is so pretty and he does whatever I tell him to do. He scrubs my floors with his tooth brush and bends over so pretty as I instruct him to get on all fours and scrub harder. Oh and the pretty pink thong that I make him wear as it rides up his ass crack. I like to grab it every once in awhile and pull it up so it gets tighter and is uncomfortable for his dangling balls. Oh, plus I really enjoy when I walk in and he is not doing exactly what I told him to because at that point I make him bend over and I stick my anal beads into his tight little rectum and make him crawl across the floor because I know he secretly likes things up his asshole. By this time tomorrow my house should be fucking spotless. I am so glad I hired my pretty little maid.

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.”

Sissy Humiliation

sissy humiliation

I am a switch – I go from the best girlfriend to the best sissy training phone sex princess ever. I’ve been very focused on humiliating my new favorite loser. He actually used to follow me around in high school, such a creep. Now he’s came crawling back to me, but for lessons on how to be a sissy whore. I was more than happy to help, and I’ve been spending all morning perfecting his sissy maid training. He had to really max out his credit card to make me happy! I bought him and myself tons of whore clothes, and makeup. Let’s not even get started on the shoes! I only had to make a few phone calls and my friends were there to humiliate, and of course fuck his tight sissy ass! He honestly tried to tell me he’d never sucked dick before, and never even had one in his ass. I knew he was full of shit though! Soon he was my bitch, and loving every second of it.

The Best Phone Sex is Sissy Humiliation

best phone sexThe best phone sex is sissy training phone sex. For me it is at least. Maybe not so much for my sissy callers. You see I make sissies prove themselves. Nothing annoys me more than fantasy sissies. I want my sissies to do humiliating tasks and send me photos. I want to know they are really wearing women’s panties because I prefer real sissies. I train my new sissy callers to my particular tastes. I love sissy humiliation, so every new sissy caller has an embarrassing task they most complete before calling me a second time. My latest sissy needed a lot of help. He gets high and gets sissified. He always insisted that if it were not for some high end cocaine and pharmaceutical Mary Jane, he would never have sissy thoughts. Bullshit. We all know that when you are high or altered your freak flag flies high. That is when you are at your most honest. You do not deny yourself feelings of guilt or let societal norms dictate your behavior. So guess what? If you are a sissy high, you are a sissy in need of a sissy trainer who will push you to be the perfect sissy all the time.

sissy humiliationMeet Katie, formally known as Ken. Her first task was to buy some pretty lacy panties. Her little clit stick would be lost in boxers. She had to be clear that she was buying the panties for herself, not a wife or girlfriend because women deserve bigger than an inch worm. Her second task was to write humiliating things on her feminine body like “tiny dick loser” and “I clean bull’s spunk.” Of course I needed pictures so I could post on my blog and know she was being a good little obedient sissy. I made her text the picture to ex girlfriends and apologize for not realizing sooner that size matters . I helped her pen an ad for Craig’s List to find a big black daddy to help her  hone her cock sucking sills.

Katie has come a long way in a few weeks. With her sissy trainer / phone sex therapist helping her, she will become the best cock sucking sissy faggot out there. Do you just need a sexy no nonsense sissy trainer to be the best sissy you can be too?