Category: Humiliation phone sex

Kayla’s New Butt Plug

mistress phone sex

I must update you on Kayla. She is doing marvelous, a certain slutty hunger inside her is coming out. She truly can’t get enough. Her butt plug has become too small so during her lunch we went and got another one. A bigger, thicker one. One that would fill her man pussy up nicely. We went into the bathroom and as she bent over and pulled down her sissy panties, I removed the old one and rammed this new one in. She gasp in delight at how wonderful it felt. She modeled it for me, bending over and spreading her ass cheeks wide, showing me that pretty jewel. I was so proud and enjoying the show, but she had to get back to work. We pulled her pretty panties up and marveled at the way it made her ass stick up. I watched as she walked down the hall, thoroughly enjoying the way it made her feel. I imagine there was plenty of leaking on those panties as she entered her room. Then my sweet sissy Kayla turned on the zoom meeting and began teaching those little cuties on the other side of the computer. I know you want to be just like Kayla, so pick up the phone, give me a call and I will take good care of you.

The Sissy Games

Mistress Phone Sex

My darling sissy boys have been cooped up in the castle for days now due to inclimate weather. Well, I wanted to humiliate them a bit, just for my own enjoyment. I called up my closest confidants; countesses and dutchesses from across the meadows. We brought in the tailors, and what ensued was three days of extreme sissification.
We played dress up with my little femboy bitches; every one of us ladies got a pet. We had a fashion competition with them! The winner would get to cum by the hand of their Mistress. Whoever came in last would be given a public humiliation in court. The entire Kingdom would attend.
That is my favorite part, to be honest; watching my sissy girl scream and beg and cry as she is tickled and edged mercilessly, only to be locked back in her little clit cage for an entire year. My Ladies always enjoy it too; my other sissies lick and stroke our perfect royal cunts while we watch, and we play a game with them too. The concept is the same; whoever makes their Mistress cum first also gets to cum. Whoever doesn’t make their Mistress cum on their sissy face gets the same treatment, until we’re out of sissy girls to torture. I still need a fembitch to be my pet and make me cum. Want to play?

Humiliation Phone Sex

Humiliation Phone Sex With a Sadistic Mistress

humiliation phone sex

Someone with a tiny lil clitty like you have isn’t good for much other than humiliation phone sex. And I hope that you know our humiliation call is going to be more than me just laughing at your poor excuse for a cock. It’s going to involve me getting you all dressed up so you can learn what it’s really like to be treated like you don’t have a dick. You’ll be treated like you are a woman completely when you’re on the phone with me. And if you’ve never gotten your pussy fucked, get ready because that’s totally something you’ll be doing. And speaking of getting ready for your pussy being fucked – do you have a dildo to play with? If not, you need to get on a website right now and order one. That way you can tell me it is on the way when you call me. It’ll make me so happy to know that I’ll be the woman to teach you all about being fucked. Once you’re used to that, I can pimp you out for bachelor parties and poker games dressed as a maid or cocktail waitress. Are you ready for your training? Let’s get this party started!

Why should I hold your hand?

best sissy trainerWhy should I hold your hand and lead you thru every single little step of sucking a man’s cock sissy? It’s not like this was the first time you ever sucked a dick, I know you have done it a million times. I have seen you do it myself many times so why are you acting like a little shrinking violet now? Do you think it’s cute to act like a little virgin? All it does is annoy the fuck out of me so now I will have to punish you instead. That’s right, bend over you little brat here comes my biggest strap on cock for your little faggot ass. I’m going to fuck that little asshole of yours until it is gaped wide open and you are begging for mercy. And when I am finished I will make sure to have at least a dozen men here for you to suck off whether you want to or not.

Best Sissy Trainer On and Off the Phone

best sissy trainerI enjoy being the best sissy trainer online. My sissy twins will tell you I am the best trainer in the real world too. Most moms would be appalled if they had boys like mine. Even when they were just tots, they were playing in my panty drawer. I knew they were special. They preferred my panties to their superhero underwear. They preferred their sister’s Barbie dolls to their Legos or Matchbox cars. They had crushes on male celebrities. They just never showed any outward masculinity. I started my career as a professional dominatrix. My boys are the reason I became a sissy trainer. I read up on it so I would be able to help them. Parents can harm their offspring if not careful how they handle outside the box interests. They are my boys. Gay or straight. Sissy or masculine, I was going to nurture them. I took them dress shopping. I helped them with their hair and make-up. I taught them how to suck cock and take it up their sissy pussies. They are rocking the sissy look now. They are secure in who they are too. Online sissy training is popular. I get it. You are a closeted sissy with no one to confide in or no one to share your sissy tales with. I helped my two boys become sissy girls so I can help you. Are you ready to come out of the closet yet and embrace your sissy life?

Mistress Phone Sex For Sissy Slaves

Sissy slaves need guidance. The sessions with me as your Mistress phone sex sissy mom are going to be the best way for you to learn your place. You already wear the panties in your relationship and sometimes that isn’t enough. I will love to assist in you dressing for cock. You will come around and understand that your looking pretty and feminine for that big daddy cock is essential. We can get you to that place. I want to train you to be the little cock whore for that BBC that you crave to be. It’s in my very wishes to have you dress and look your sluttiest as you service that cock. You are a slave to big black cock. A simple little pretty slut sissy slave for the much bigger cocks. You are not a man, You are a Sissy Slave.

Mistress Phone Sex

A Halloween Treat

mistress phone sex

Oh, my sissy showed up at the door wearing the matching costume I had for him and my husband. They were both Disney Princesses this year. The looked adorable in their little dresses and tiaras. However, I did make one adjustment. I ripped their dresses so they were super short, and I could get a nice view of their pink sissy panties I had picked out for them. Now a touch of lip gloss and we were ready for Halloween. I had already called the anaconda to come see me and the sissies were ready and waiting when he arrived. Always on their knees where they belong. He laughed at their cute dresses as he pulled his cock out and smacked them in the face with it. Then he told them to suck it, like they were bobbing for apples. Once he was hard and wet spots appeared in the princess panties, I had them guide that beast into my wet pretty pussy. Their little hands trembling with excitement as they pushed that beast inside me. Then they watched as he pounded my cunt. Since it was Halloween, he decided they needed a treat. When he was about to cum, he pulled out and graced their little tongues with his warm hot yummy cum. They licked it all up like the cum whores they are. We had much more fun and I will give you all the hot naughty details when we talk. I will be waiting for you.

Online sissy training Kayla the Switch

online sissy trainingOnline sissy training Travis Aka sissy Kayla has been quite the experience! See he is a closet fag. He has to run and hide our phone calls because his wife doesn’t know about his indiscretions. I mean surely she has to know he is an uncover bisexual cock sucker! I could tell right away! Vibrating anal beads up that sweet back door ass pussy as he drives to get them food. He wants to tell me all about his craving for African food. BBC. His pink panties are under his work clothes in the mornings and he is jacking that cock off to me and him roleplaying some fun scenarios. And as Dominate as I am I have that switch part of me that will cave for a strong hand. I am a brat and when Kayla becomes Travis again and wants to fuck the shit out of me, I laugh and get snide with him. But my pussy is telling me that I want him to top me. I yell out fag, and he says I am his slutty whore. It sounds like a white trash scene from one of his porn movies. I give him his cock sucking home work for the week and tell him that he is still a faggot even though he likes pussy too. Don’t get me wrong I am still strong in my sissy phone sex game, but as a tease and a brat, I work well with sissy men who have a little more substance in their panties. And a little opphhh to back that faggot ass up! I do love a nice cock call with non faggots too! Just a brat with a whore pussy who can switch it up!

Kayla’s Big Adventures

mistress phone sex

Let me tell you about Kayla. She is new to the game and I can hear the excitement in her voice as I train her. We recently went on a little shopping trip and she picked out all kinds of adorable girly clothing. Some pretty lace panties and sexy dresses. She even got a bright pink butt plug. Then she went home and tried everything on and like a good sissy sent me pictures of her wearing them. The way her man pussy takes that butt plug is amazing. So deep and she was so proud. And the picture of her in black lace panties made her little clitty look adorable. Then we talk and she fucks herself with her dildos. I love listening to her moan as she makes little cummies. The thought of a warm thick big cock in her throat and in her man pussy excites her so much I suspect she is going to be a cum slut and a cock whore. I love when she calls and tells me how she is wearing panties and a bra and her butt plug under her work clothes. It is so hot. I can’t wait to see what we have in store for her next.

Online Sissy Training Available

online sissy trainingOnline sissy training has quadrupled in popularity during the quarantine months. Even though things are opening back up in most states, guys are still leery about going to professional mistresses. An online mistress is cheaper and safer. More discreet too because you can talk to us at your convenience. My busiest times are late at night and early mornings when the rest of your house is sleeping. I like my night sissies who can sneak into their wife or daughter’s panty drawers undetected.  If you are a sissy who is married and need to keep your lifestyle a secret, an online sissy trainer can work with what you have. You can steal panties out of the hamper or your wife’s drawer. You can borrow some make-up and some clothes. Maybe some jewelry and shoes too depending on your level of desire for the feminine look. Household items and food can become sex toys. Most sissies aspire to being cock sucking faggots and back door sissies. A cucumber or zucchini, even a water or beer bottle make excellent makeshift cocks. Many wives have a hidden toy in the house I can help you find too. I have helped men shave their bodies with online training. I have helped them find places near them where they can get some discreet faggot action. I have feminized them head to toe too. Just because you cannot safely go visit a sissy trainer, does not mean you cannot get sissy training. Phone sex sissy trainers and mistresses are here to make you the best sissy you can be.