Category: Domination phone sex

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.

I’m a BBC Sissy Trainer Where Ever I Go

bbc sissy trainerThere is never a dull moment when you are a BBC sissy trainer. I got stuck out of town. I was in another state for a wedding when traveling suddenly became difficult. My plan was to rent a car instead of flying. I had to wait two days for a car to become available. I was in a nice hotel, so I thought I would make the best of it. I went to the hotel bar and met some fellow stranded folks. Charlie was not fuck material. Demure man. Feminine characteristics. Talked like a sissy too. When he asked me to dance in this girly pitched voice, I laughed. I joked that he would probably prefer to suck on a big black cock. He got ashen white. “How did you know,” he asked incredulously. I told him I was a sissy mom and a sissy trainer. I have an innate ability to spot a sissy a mile awhile. Charlie and I talked over drinks. He really wanted a big black cock, so I got him one. When you look like me, finding a black stud is never difficult.  This time, I just had to look around the room. I saw a handsome stud and he locked eyes with me. He was in my room an hour later and so was Charlie. I let Charlie watch first. Like many sissies, he had only seen big black dicks on the Internet. I was there to give him the real thing; I was there to turn Charlie into a black cock faggot. He was chomping at the bit. He had a hard clitty. He was wearing panties. My black stud thought it was funny that I had a little faggot boy watching. He didn’t mind. When I told him, I wanted him to skull fuck the little faggot, he didn’t skip a beat. He pulled his cock out of my cunt and shoved it in Charlie’s mouth. That would be as close as Charlie would ever get to my pussy. Charlie was in heaven sucking my cunt juice off his first black cock. He was a natural. Sadly, I likely won’t see Charlie again because he doesn’t live near me, but at least I gave him a memory he will never forget.

Lily’s Big Debut

Sissy trainingThe men gathered together waiting for Lily and I to come down the stairs. I spent over an hour getting Lily ready, I even put her chastity cage on her clitty for her to ensure it was done right. I surprised her with a blonde wig I bought just for her. Tonight she wasn’t going to just have her first cock, she was going to have as much cock as she could manage to take. By the time I was done with her, she was stunning a completely new person then that man I had known from work. Escorting her down the stairs almost made me feel like I was giving away a bride at a wedding, though instead, I was giving her off to be fucked for the first time like a woman. The three guys I selected would be gentle with my delicate flower, but their cocks will leave her aching. I watched as they gently touched her all over, kissing her and easing her down to her knees. Their cock’s hard and ready for those pink full lips to taste a real cock for the first time. Never once did she look back at me or try to back out. The moment she put the first cock in her mouth I knew Lily was all in and wasn’t going back ever again.

Mistress Phone Sex Sissification Expert

He was on a binge and smoking on that glass dick with the candy of his kinky desires that made him into a bitch. I do Mistress phone sex calls and love my party bingers that get all in the mood to become little bitches for dick. They pull out their pretties and dress up for their Mistress. Smoking that crack and feeling pretty silky panties, hose and lingerie cross dressing their clitties makes them call me to get their fix. I train them and guide them into being sissy cock suckers that crave for black cock and cum. Sometimes it’s not even about the color these little faggots will take any big manly cock I tell them to. It’s so great to hear about how pretty they are making themselves as they are dressing for that dick.

Mistress phone sex

No One Wants To See That

Humiliation phone sexRecently I received a dick pic that was of course unsolicited. And quite honestly I couldn’t think of a better way to respond then to publicly. So here goes.

Dear Little Dick,

Thank you for scarring my eyes with that sorry excuse for a cock. It honestly took me a minute to comprehend that you hadn’t just sent me a picture of a Vienna sausage in your hand. Your cock might be small but I assume your balls are big since you decided to send me a picture of it. What was I suppose to do? Get super wet and let my panties drop to the floor. No, no thank you. I want no part in handling that micro-cock. As far as the “Want some” you sent along with the picture…well no definitely not. What woman would “want some” of that. We don’t like cocks that come in sampler sizes, especially not a woman like me. I want a big dick and that is exactly what I get. Why? Because I have self-respect and I’m well aware of my attractiveness. But even if I looked like a trash bag I wouldn’t touch your pellet.

My Boss’s Transformation Continued

Sissy trainingOver the next few days, I would slip him a few more pairs of panties with instructions to be wearing a pair each day. Then I observed his behavior. He was happier, more relaxed having someone to share this secret with must have been a huge relief. Each night after work I would stay late (paid of over-time of course) and we would discuss my future plans for him. I took some measurements and we sat down and did some online shopping. I needed to make sure my slut had the proper attire for her debut weekend. Her sissy coming out party had been planned and now it was just getting her ready. First the outfit, we decided on an innocent look as we agreed it would be best given she was a sissy virgin. So white lace panties, garter, and thigh high stockings. A beautiful white satin chemise, with a gorgeous white sheer long flowing robe. The order was placed and set to arrive at my house the day before the party this upcoming Friday. So all that was left was practicing for the big day. I bring my strap-on to work and I’ve been teaching her how to suck cock, and I’ve provided other fun accessories to prepare her sissy pussy for her first time. Soon my new sissy who I’ve finally decided to bestow the name Lily will be more than ready for her big day!

Online Sissy Training

online sissy trainingOnline sissy training available here. I love dressing up sissies. I have a daughter, but a woman can never have enough sissies. I also have two sissy sons. I have been training sissies at home and on the phone for years. It is more than a hobby; it is a job. Occasionally, I get paid to make a sissy. I was paid $5,000 from an unlikely client recently. The client was a woman. She wanted me to turn her son into a sissy. She always wanted a daughter and she had this sixth sense that her son was not going to grow up to be a ladies’ man anyway. Mothers know. If you are a sissy, I bet your mother was the first to know, even before you did. When Sally arrived at my place Friday night, she had her son Trey with her. He thought they were at my place for English tutoring.  He was there for sissy training. He was unassuming for a young boy. He had a naturally feminine body. I didn’t think he would fight his feminization, but he did. I prefer to be sweet and nurturing, but if a sissy fights me, I fight back harder and win. I took that sissy bitch, tossed her over my lap and spanked her. Bare bottom spankings are something I can administer well. After I was done wailing on her ass, I shoved a butt plug in her ass. Her momma helped me duct tape the butt plug in her sissy ass. She helped me dress her too. She was better behaved with that butt plug in her back door pussy. In fact, it made her clitty hard. Once she had a hard clitty, she was easier to train. Sissies get pleasure too. They get twat teased and abused also, but almost every sissy I know loves to rub her clitty. Once we dressed her and pleasured her back door pussy, she transformed before our eyes. She didn’t even put up a fight when her mother and I put on strap-ons and tag teamed her new pussy. She welcomed it. Another sissy converted under my watch.

Princess BBC Sissy Trainer Zoey

BBC sissy TrainerHaving a boyfriend and daddy that need Me as their BBC sissy trainer makes me very wet and Cumming constantly. I love feeding them Big black dick anytime I feel like it. My sissy lala boyfriend and I were studying for a major test and my pussy began to throb from out of nowhere. And that is when I heard our neighbor Shawn and daddy talking downstairs. My pussy had BBC radar I swear! I got up and told My Boyfriend that we needed to put on our prettiest panties and nothing else because I was going to get at least one of us fucked! I ran downstairs dragging my sissy BF. I Was so excited that I ran right into Shawn. AL 6 foot 5 inches of chocolate man meat! My tits pushed into his chest as he looked from me to my Boyfriend in his sissy panties. My daddy had stopped in the hallway knowing what his baby girl mistress what up too. Shawn looked to daddy saw his face and back to me. He laughed and said little cuckold mamma you run this fucking house, don’t you? That when momma came in from work and said yeah she does now are you going to fuck her like she deserves Shawn? Momma is so good to me. We fucked all Saturday night me and momma sharing his 10 inches while Daddy and sissy boyfriend watched, jack off and cleaned us up.sissy panties

Sissy Slave Training at the Glory Hole

sissy slave trainingI had a busy weekend sissy slave training. I have this one sissy who is a work in process. I have been feminizing her the best I can, however, I don’t have much to work with. She looks more like a transvestite than a femboy. I have dressed her, done her make-up and given her a pretty blonde wig, but she doesn’t look feminine enough to be one of my sissies. I thought perhaps if she swallowed some cum, it would help feminize her more. I dressed her up in a pretty dress. I did my best to make her look pretty and I took her to the glory hole. On the weekend, the glory hole is hopping. My plan was two days of cock sucking and cum guzzling would make her more feminine. Friday night we spent 5 hours at the glory hole. She was such a good cock sucker. She blew 46 cocks. Can you believe that? That was Friday night. On Saturday, we spent almost 8 hours at the glory hole, and she guzzled another 52 cocks. I was keeping track. In two days, she sucked off almost 100 cocks. She swallowed almost 100 loads of man seed. Cum is transformative in sissies. It helps soften features. It helps grow breasts. It helps stop hair growth on the body and it feminizes a sissy. I was very proud of my not so feminine femboy. The cum helped, because she looked radiant today. Something about being such a good cum guzzler pushed her out of the transvestite category and more into the sissy girl category. If you need help becoming a better and prettier sissy, you need some phone domination from a sexy sissy trainer. I want to help you get cum too. I want to help you become a very pretty cock sucker.

phone domination

Best Sissy Trainer Teaches Cock Whores

Mistress mommy Diana is the best sissy trainer in the burbs. I have so many family man types that aren’t really men. These guys play the role well but they don’t fool me! I know a closet sissy when I see one. They are often busy professionals in their 50’s that need to let it all go. These guys can’t be themselves most of the time and visit me to be sissified and used. My sissies vary so much though. I love them all as a mommy loves her obedient good boys. I am open to being your sissy mommy and you can serve me and watch me get fucked. Clean my creampie like a good little cum slut. I will have you wearing my silky panties and whore lipstick as you learn to be a cock sucking, cum guzzling, sissy slave to big dick.

Best sissy trainer