Tag: Sissy maid training

Sissy Charlie Cleans Up Her Brother’s Cum

Mistress Phone SexI have been training Charlie to be my little sissy. She has a micro clitty, so she is of no use to me in that regards. She is so tiny that I could not even find a cock cage tiny enough for her to wear. So, I resorted to a pretty pink bow on her clitty and frilly pink panties with lace on the back. Tonight, I plan on having her be my clean up sissy. She is very dedicated, but I like to push my little trainees sometimes. I invited her brother over to join in on the fun. Kyle walked in and I immediately had Charlie come down and show off her pretty panties. Kyle got the biggest kick out of that and just laughed hysterically. Charlie just hung her little head, but I know she secretly liked it although we couldn’t tell because her little clitty is so small. I led Kyle and Charlie back to my room and had Charlie undress us both. Next Charlie was told to get on her knees and get Kyle hard for me. She was hesitant at first, so I had to smack that little clitty a few times with my hand to get her moving. But once she put Kyle’s dick in her mouth, she started giving him the best blowjob. She was taking him so deep and Kyle was starting to moan. Charlie is not worthy of bringing him to orgasm, so I had to stop her. I could tell she was disappointed as I had her watch her brother fuck me nice and hard repeatedly. He fucked me in my wet pussy and my tight ass leaving his load in both. When we were finally finished, I motioned for Charlie to come over and clean all her brothers cum from my pussy and asshole. She lapped it all up like a little puppy. As a special treat I let her lick her brother all clean too.

Come Serve Your Mistress

sissy maid training

Nothing fulfills a Mistress like getting to train a sissy slut maid like yourself. The process from beginning to end is a real treat to witness. They usually come to me all insecure and shy about this role that they know they are meant to fulfill. It’s often some family man with a well respected job as an authoritarian of some sorts, who simple can’t shake the feeling that he was meant to be a submissive little sissy boy. That’s where I come in. I take great pleasure in easing you into my sissy maid training operation. Don’t get too comfortable with the word ‘ease’ either. Now let’s start with the little details you keep to yourself on a daily basis. How often do you fantasize about sucking cock? What kind of cock do you fantasize about? I’ll bet it’s often a fat, long, veiny black one! How many times have you given in to the impulse to slip into your wife’s, girlfriend’s, sister’s or even mother’s panties? These are the things we need to establish in our training session.
Tick tock, little cocked sissy boy. It’s time to step into the role you were meant to fill. The sooner you embrace it, the better it is you’ll serve.

Charlie Gets Those Dicks Ready to Please Me

Mistress Phone SexMistress phone sex with Francis is what you need to keep you in check. I love to take my little sissies and have them begging for my affection. I had Charlie come over today and be my sweet little sissy slave. I invited two of my friends over to play. They are well hung and are packing more than a mouthful. Before I fucked them, I had Charlie take those big dicks in her mouth and get them nice and hard so they could please me. I then had her sit and watch as I took those fat cocks deep inside my pussy, filling me with their warm cum. When we were done, I had Charlie clean their cocks and balls until they were nice and clean. I saved her favorite thing for last. I sat on the desk and spread my legs and let her eat my creampie pussy until every drop of their cum was out. The feel of her tongue deep inside me made me horny again so I let her lick my clit until she brought me to orgasm. I then patted her on the head as she crawled away on all fours back to her little corner to wait for my next command.

Sissy Training my Little Cum Slut

Mistress Phone SexA good mistress knows that she must train her sissy to be a little clean up slut. To clean up all the cum and to get those dicks nice and hard for me to fuck. But sometimes I like to get those dicks hard myself. I love to 69 a guy and let him lap up my pussy while my sweet sissy slave watches on. I can almost see them drooling as I take that dick deep in my mouth and make it rock hard. If I am feeling especially naughty I have them come right to the end of the bed, so they are inches from that cock they so desire. I tease them as I lick it slowly and my man moans loudly in delight. I watch that sissies’ eyes light up as the pre-cum flows from that cock in my mouth. I lick it up and then stick out my tongue to let them see the yummy cum that I have. I have them in cock cages so they can’t get hard, but the desire is still there as they leak from their tiny cages. Lastly, I take that cock so deep in my mouth and throat fuck it so good that as he is squirting his load, I aim it right at those little sissies so that it lands on their faces. But I won’t let them lick it up just yet. I keep them on their knees begging for it before I let them clean up that dick for me so I can take it for another ride.

Tammie gets a Treat

Sissy TrainingMy sweet little Tammie has been such a good girl lately. Doing everything that was asked of her. She had been our little cum whore at my last penis party and even licked up my creampie pussy without even being asked. She stayed on her little knees and sucked every man and shemale that came to her so that they were nice and hard and ready to go. She politely lifted her sweet ass and let them take turns ramming their dicks or dildos deep inside her. She cleaned everyone up too, leaving not a drop. So, to show her how wonderful I though she had been I got her a special present. Laid on the bed was the prettiest pink dress and matching garters, a pair of silky hose, black heels, toe rings and a beautiful new cock cage. Her eyes lit up when she saw them, and I told her to put them all on. I had her twirl round and round as she showed her new outfit off. Finally, I told her to lay down on the bed because her best present was yet to come. I could see the liquid dripping from her sweet cock cage from excitement as Sandy, the biggest, blackest, most beautiful shemale entered the room. I handed Sandy the key and told her that Tammie was ready to play as I winked at her and closed the door.

Sissy girl training

sissy girl training

I took my newest fairy pet with me to the mall to go shopping. Everyone knows that the key to the best sissy girl training is making your sissy feel as girly as possible. To do this, I knew I had to put her in those adorable, silky sissy panties and make sure as many people saw them as possible. Every time she bent over to look at something, I would lift the back of her shirt so that the edge of the panties peeked out from the top of her pants. Knowing that so many people were seeing her in those panties  was really getting my little fairy hot. I took her into the bathroom and made her strip down to nothing but those silky panties and stand there playing with her little fag clitty. Plenty of real men were walking in and making fun of my little fairy fag but I didn’t care. I made her stand there and rub her little clitty in those panties like the well trained sissy she is. I laughed as the men walking in made comments about my sissy bitch and even took pictures with their phones to post on social media. I was loving every second of it! Publicly humiliating my sissy and letting the world know what a girly girl she is, was the best time I’ve ever had at the mall.

Sissy Maid Training For A Cum Dump Like You

sissy maid trainingLift Your silk  Petticoats you are a sissy maid now and it is time for your spanking! Dear one did you think your transformation was complete with just your pretty little maid outfit? I will break you. Glitter lip gloss and pretty panties do not make a sissy. I have had better sissies wearing jeans and tight t-shirts. Your first step is going to be drinking cum from a tiny teacup after you serve your mistress. Pinkies out and lift up and show me your cage before you serve me pet. Not enough sugar, that’s three swats to your ass cheeks with my wooden paddle. Oh yes, red paddle lines! Now to crawl on your hands and knees between my legs and get the scent of a real woman that you will never be. I know now that spanking a sissy is not punishment but more of a reward, every pain I put you through makes you more of a sissy and you adore it. There is no harm in spanking my sweet small cocked fairy sissy maids at all. I know the next part of training is what you really want though. The biggest blackest cocks to fill your slutty troat and stomach up.  Get the lotion pet you are entering Mistress Zoeys Playroom.

Your sissy girl training will begin now!

sissy girl training

Sissy maid training

Sissy maid trainingCome one, come all! It’s time for Mistress Genesis to have a special little class, a class called Sissy maid training 101! This class requires quite a large deposit, and I have a list of things you will need to purchase for this class as well. Only obedient sissies that are dying to learn how to be sissy maids are welcome in my training class. I need passionate sissies only, the best of the best will survive this class and have a very special graduation ceremony. The school supply list goes as follows: 7 Sissy Maid Uniforms, I have supplied a list of locations you can buy the type required for this training. Secondly stockings all in a mixture of white, black & nude! Next, we have a mixture of high heels to wear, as well as wigs for each day! Hope this list isn’t too overwhelming we are far from done. All the sissies will need to have a full makeup set, receive laser hair removal all over, and get a french tip toes & fingers. Each sissy is allowed to choose three of their favorite torture devices to purchase for class. More information next time my sissy maids!

Sissy Maid Sluts

sissy maid training

I love toying around with my sissy maid faggots. Especially after getting them all dolled up in pink frilly uniform with teeny lace apron, stockings and heels! My sweet sissy maids love to wait on me hand and foot! They do whatever I say, no matter what the request is. I love getting these maid sluts into the messiest situations! First, I start by having those sissy fuck fags get railed out by my trusty fuck machine until their assholes are nice and gaped wide open. Once my sissies are nice and stretched open, I love having juicy thick cocks unloading their sticky hot cum inside of all my sissy’s faggy buttholes! They love having their assholes gaped and stretched! But this little hobby of ours can get so messy. Luckily, I have a few cum bucket sissy maids who I put in charge of cleanup. I call my little cleanup crew over to slurp the hot cum out of those used up assholes until their bellies are full!

Sissy Phone Sex Fun

sissy phone sexSissy phone sex is the most fun a woman like me can have! I am amazed still that I have a job like this. I am a real-life sissy mom. I love turning men into the sissies they were meant to be. I also like talking to real sissies. I find it enjoyable to hear how other sissies have been raised and their experiences. Some sissies are for daddies and some are just for mommies! My two sissy boys are for both. I have raised them to take care of me sexually. They eat mommy’s pussy and ass. They take care of their sister too. They do the housework and help with our beauty. By that I mean they give us pedicures and manicures, even do our hair and make-up on date nights. My sissy boys also make money for my daughter and me. I pimp out their sissy holes to rich daddies who like young sissies. At a certain age you can’t tell the difference between boys and girls. A tight backdoor pussy feels the same as a front door one!  My pretty angels entertained a super wealthy daddy last night. He wanted them both and paid well for them both. Their sweet young holes got fucked for hours. They still have cum inside of them. Today, however, is about me and my daughter. My sissy boys are prepping to watch us get some big black cock. Sissies are so versatile. Are you a good sissy or do you need sissy training?