Category: Sissy maid training

Sissy maid stories always crack me up!

sissy maid storiesSissy maid stories always crack me up so when a little sissy bitch named Matthew called me I knew that it was going to be a very entertaining call… for me anyway, he was going to be humiliated and shamed. This little bitch boy was all shaved and had long feminine hair, he was all dressed up and had a full face of makeup on, this was clearly not his first time dressing as a sissy. He asked me if I thought he was beautiful and I just had to laugh, I told him to look at me if he wanted to see beautiful, that he was just a pathetic wannabe! You are not a woman just because you shave and put on a dress! What you are is a silly little sissy boy that needs a good fucking to show you your place! That’s why I fucked that little sissy boy with my biggest strap on cock, by the time I was done he was much more aware of his place!

Women In Charge

Sissy Maid Stories

I am part of a highly exclusive club where things are a little turned around. Here, it’s the boys that drop to their knees at the command of a woman. The ladies get the VIP life, while the men are collared and leashed to serve the women. We keep a few of the buff bodied sissies up on the stripper poles, doing sexy little dances for some of the femdoms who are chatting with their friends, of course, using the men to sit on or as foot rests. Sitting at the bar to order a drink, one of the sissy boys dressed in a little maid’s uniform came up to talk to me, as was customary when a femdom walked in and was not already accompanied by one of the girly boys.

I kicked off my shoes. I had spent a long day on my feet, so I ordered him to massage my feet through my stockings. The bartender brought me a drink as I moaned from the tension slipping away from my body. Opening my legs, I signaled that he should now begin to please me in a different way. He kissed up my thighs before licking my clit. I pushed his face deeper into my pussy as I came on his face. After catching my breath, I dismissed him. I didn’t need him getting attached and trying to get me to take him home as my permanent pet.

Sissy cuck with PMS prissy man syndrome

Cuckold phone sex

I don’t really suppose cuckolding can be done with a dildo, but I’ll just do it anyway. My sissy hubby has been a super bitch lately. It seems like he is having PMS, prissy man syndrome, sullen, bitchy and no fun at all. When it was chores and panties time the other night he actually rolled his eyes at me and let out an exasperated sound at me. I wasn’t too happy about that, nothing in his sissy training has included giving me attitude. I do understand that his job is very demanding and stressful so I gave him a scolding and told him to keep his complaints to himself or I would have to dole out some punishment. He didn’t seem all that impressed either way and he went about his chores. A few hours later when he was done I told him I wanted to cum. He got onto the bed where I way lying naked stroking my pussy, he started licking my wet little fuck hole and clit without much enthusiasm. When I got tired of his half ass effort I told him to go sit in the corner and if he wasn’t going to do it right he could watch me every night for a month with someone else or a something else. That seemed to perk him up a lot and his cock got nice and hard. Finally the sissy I know is back….but I think with that behavior a punishment is in order.

Sissy Maid Training all night long

sissy maid trainingI never knew about sissy maid training until I met my husband. He’s much older than me and his cock is so small. Good thing his bank account is nice and fat.
He swept me off my feet with his charm. I couldn’t wait to feel his cock inside of me. When the time finally came and I slipped my hand into his pants, I was horrified. I smiled awkwardly and he burst into tears. That’s when he revealed his secret. He was looking for a wife like me because he needed sissy maid training and he knew I was just the woman for the job.
He bought me piles of sexy lingerie and spa treatments. Then he sent me out at night looking for the biggest cocks I could find.
My masculine businessman spouse turned into a cum craving slut!! He loved watching me get fucked. He could barely wait until you left so he could lap up the creamy leftovers and jerk his tiny weewee onto my big tits. As for me, I am loving it. I feel like the luckiest woman alive. I can barely wait until tonight when I go out searching again. Are you a cucky slut, too, who needs some training or are you the oversize cock that I’m searching for?

Sissy Humiliation

sissy humiliationSissy humiliation Sunday? It is becoming a real thing with me. I think because yesterday was Mother’s Day, more guys than usual were getting sissified. Did you ever wear your mommy’s panties? One of the many things sissies have in common is a love for panties. On a psychological level, I think sissies know that their package is too small for boxers. The other thing sissies have in common is a small package. Did you try on someone’s panties when you were a little boy? The silk or satin, even cotton, feels good against a little nub. I bet if you tried on panties when you were younger, you popped a little chubby. Panty boys know that the closest they will likely get to pussy is wearing panties. With a little nub and a feminine demeanor, the best a panty boy can hope for is being a sissy. Women like me don’t give men with clits the time of day unless they pay us or we need a good laugh. Sissies do serve a purpose, however. Besides the small dick humiliation, they make great maids and pay piggies. One of the things I love most about being a sissy trainer is the fact that a sissy is so pathetic she will pay to be denied and shamed. Off the phone, I have a few sissies who pay me to clean my house. They also tribute me. I look at all money I receive from sissies as an annoyance fee. I need to be compensated for my time spent with losers. I am a hot MILF who can fuck anyone she wants, so time I spend with guys I wouldn’t fuck for a million dollars is time away from real men. On or off the phone, if you are a sissy in need of training be prepared to compensate me for my time. And, be prepared to do as you are told.

Maid Wanted

Small dick humiliationPull down your pants, let me see what you’re packing. Oh my God! Is that it? LOL! Seriously, you have the cock of a two-year old. There’s no way you could please me with something that small. You look like a female with a huge clit. I think you should be a female, and you should be my personal french maid. Put this French maid uniform, it’s your perfect size. Let’s put red lipstick on your lips and this blonde wig on your head. Look in the mirror you look like a real bitch. Now start cleaning, I want my house spotless. I need you to vacuum, dust, wash dishes.  Don’t act like a dumb bitch you know how to clean from top to bottom. And when you’re done cleaning I’m having male guests coming over and it’s your job to make them feel welcomed and comfortable. I want you on your knees with one of their cocks in your mouth at all times. If my guests want to fuck you…you bend over and give them some boy pussy. That’s a good bitch. Don’t let me down.

Sissy Humiliation with Our Site Sissy

sissy humiliationSissy humiliation is one of my favorites things to do as a phone sex woman. This company sees a lot of sissies too. No sissy is as pathetic as Sissy Michael, however. She is the personal sissy of our fearless leader, Mistress Levi. One of the many perks of this company, however, is the chance to shame Sissy Michael ourselves. I have quite the sissy fan base, but our site Sissy makes them all look butch in comparison.

sissy maid storiesSissy Michael or as I like to call her, Sissy Fairy Fag, even has her own website so anyone can call and shame her. If you enjoy sissy maid stories, I have plenty to share with you. Sissy Fairy Fag dress up like a princess, maid, pig, bunny and a baby, depending on her orders and mood. She has quite the sissy wardrobe. She goes out in public without shame completing humiliating tasks like buying panties and getting her nails done, even shopping for diapers. They might be humiliating to a real man, but to a pathetic pansy, they are embraced with glee.

best phone sexI have spoken with Sissy Fairy Fag on more than one occasion. She sings little sissy songs and relishes in telling her long history of sissydom. Sissy Fairy Fag deserves shame. First, she is pathetic. Not just for wearing feminine clothing and prancing about in public, but because she has a tiny little clitty stick. I could share photos of her shrimp dick with you, but you cannot unsee it. She frequently poops her panties too. Disgusting, I know. Not like she can’t get to a bathroom. She likes being teased for being a poopy pansy. Hard to believe, right?

sissy maid trainingThe best phone sex is not always pleasant, but it is enjoyable for the sissy. I love teasing and laughing at Sissy Fairy Fag. I also enjoy making her tell me all the humiliating things she has done in her life as a sissy. If you are a sissy, entertain me. I bet no matter how pathetic you are, you still aren’t as pathetic as Sissy Michael!

tease and denial

Boy Pussy

Forced crossdressingI love turning big, strong men into beautiful, weak women. Come over to my place for a real make over. First, we’ll start off by having you shave all of your body hair. Next, we’ll do your make-up. I’ll put eye shadow and mascara on your eyes. And I’ll put bright red lipstick on your lips and blush on your cheeks. Then you’ll be ready for your dress, let’s put you in something slutty. I have the perfect dress that’s your size, it’s a red, tight and super short. Can you walk in heels? Well, you better learn fast because I’m putting you in 6 inch heels. The final step is your hair. I have wigs in all colors. Do you want to be a dumb blonde, a classy brunette or a dirty red head?
When you’re all dressed up and looking sexy then it’s time for you to make me some money. You’re the hoe and I’m your pimp. Your job is to suck cock and take cock in your boy pussy. And bitch you better make me lots of money. When men come over to sample your sweet ass you are to stay on your knees. You are not allowed to stand like a real man. You’re my bitch and you are to stay on your hands and knees at all times. Now, be a good girl and answer the door our first customer is here.

Manny

sissy humiliationMy lovely pet and long term client, Manny has not only assisted in keeping me in the lifestyle I am accustomed and deserve, but also has brought me so many hours of joy from my deliberate humiliation and feminization of him. He’s delightful. The type of fuckpig that wins over a pretty dom like myself’s heart because he shows such strength and determination to go beyond his boundaries day by day. I remember vividly training him to enjoy the taste of his own dirty ass…..I like to call it his Man-gina. Exploring with dildos; first small and standard sized, but soon extra large, inflatable, and gape producing he eagerly awaits the end of our session so he can push past his prolapsed anal muscles and fish out my methods of abuse, only to lick them clean hungrily, tasting the sweet boy cavern I made into a makeshift vagina for him. Just thinking about it I can hear him slurping up the length of the double headed 18 inch dildo I jam packed his anus with. Like the sweetest of ladyboy’s I’ve made he stays on the floor, writhing in pleasure  as he suckles every bit of his own fuck juices from the dildo. In perfect form, with his pretty ruffled pink panties pulled to one side. Making little bitch boy’s pretty and slutty beyond compare is what I was put on this earth to do. Just as my sweet cum slut Manny Man-gina.

Sissy maid stories Cock Slut Rob

Sissy maid storiesSissy Rob has turned out to be an even better use than I thought. She loves praise. Lives off of it and therefore she’s such a good girl to her Goddess. She’s been sending me pictures of her sucking cocks everyday. The last one was a big black cock and she was telling me how she took him in her mouth and then he fucked her and she moaned for him like a little bitch. The only thing I wish she’d texted me as she was being my little slut. I’d have loved to fuck you while watching my good girl being used. But, Rob knows she’s my toy and loves that when she comes home she knows she can sit at my feet. Rubbing and massaging them before I let her lick and suck on the toes. Worshiping her Goddess from the feet up. Giving little licks and sucks to the soles of the feet too making sure not to leave an inch ignored before kissing up my ankle and licking up my calve. She knows how to make me happy and my pussy wet. I know how much you love watching and we have her trained do well that as she licks me to orgasm she knows to present her bitch pussy to you. Knowing how much you love to sink your big hard cock into her tight little pussy, making her the fuck toy she always wanted to be. I’ll hold her face to my pussy, letting her moan into it as she drinks my cum and begs you to fill her up and be your little cum dump whore. You’re such a good girl Rob. You know just how to make me happy and all I need to do now is thinking of an appropriate slut name for you.

Sissy maid training