Category: Sissy phone sex

My Sissy Gets Some Humiliation Fun

sissy humiliation trainingOh how my sweet Devina went on for weeks begging for a humiliation assignment. However I wasn’t quite sure Devina was ready to push her boundaries. Then I realized I didn’t actually care so I sent her specific instructions with a warning that if she did not follow through I would disown her from my collections of sissy darlings. She was to meet me at my favorite nail salon at 2pm on Saturday. I knew they would be the busiest than, which made it the prime spot to show off my pretty pet. I should mention instructions entailed her showing up in a dress and pretty pair of floral sandals I recently ordered her to purchase. Much to my surprise my little sissy bitch showed up! A complete stuttering mess and a bit clumsy as she shyly looked at everyone who was whispering and giggling. Never seen Devina this shade of red before, she certainly impressed me. We each got our nails done with bubblegum pink polish and for good behavior I let her out of her little pink clitty cage for the evening. I have a pretty good idea of what she did for her Saturday night.

I made her do it

sissy phone sexMy newest little sissy bitch was reluctant to follow all of my rules so I had to punish her. And what better way to punish her than to make her do all the things she was reluctant to do in the first place right? So after she was all dressed up like a little slut I told her I was taking her out for a little surprise and boy did she get all excited. She was acting like she had been a good girl that deserved a treat or something and seriously nothing could be further from the truth. She was really a pain in my ass with all her complaining but that was gonna be changing real quick. I led her into this private club where I had all her clients all lined up and waiting for her. She was going to have to serve each and every one of them before we left there or she would no longer be my sissy. Well she cried about it but you know what? She sucked every fucking dick in the place! They fucked that tight lil pussy of hers too until she had cum running down her legs and she was too tired to stand up. Only then did I take her home and let her rest.

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

Sissy girl training

sissy girl training

Sissy girl training is my passion. I would love to strip you down, and redress you  like my little sissy slut fairy bitch. Bring your tiny little cockette over here so that I can look at it. I want to laugh as I put you in panties. You’ll wear them because that tiny excuse for a peepee is more of a clit and that’s what you will call it. I want you to rub your clittie for me through those silky panties and tell me how much you want me to fuck your sweet little pussy hole. I bend you over and spank your thick little ass until it’s red and stinging. I pull your cheeks apart and slide my big thick, studded cock right into your whore hole. You love the feel of my strap on. I’m going to hold you down and fuck your little fairy ass like the cum slut you are. You’re going to be my little fairy hoe and I will own you! I pull my cock out and make you suck it clean. I love watching you lick all of your he-pussy juices off of my strap on cock. You’re my sissy girl and I will fuck you when ever I want!

 

BBC Sissy Trainer

BBC Sissy Trainer

One of my favorite things in the world is being a BBC sissy trainer. Turning sissy sluts into big black cock whores is one of the most fun things ever. You sissies already have your look down (and you look fabulous) but now you need someone to teach you exactly how to please those giant chocolate fuck toys you’ve been drooling about for so long. It won’t take me too long and I’ll have you trained and ready to take a BBC in either one of your holes anytime and anywhere. You’ll be able to just drop to your knees or bend over and be able to handle it with absolutely no problems.
How does all that sound to you? Are you finally ready to let me train you and make you the best big black cock sucking sissy faggot in the county? I’ll teach you all my tips and trick and you’ll be such a whore that everybody is gonna know your name. They’re also gonna want to get in on the action. What are you waiting for? Call me so I can teach you everything you could ever want or need to know when it comes to sucking black dick.

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

In Need of Sissy Girl Training

sissy girl trainingSome men need sissy girl training more than others. I think I found the biggest loser this weekend. I met him in an adult bookshop. I knew he wanted to go into the glory hole room, but he was too much of a pussy. He was trying to be nonchalant, but I knew he wanted to suck some cock. He didn’t look like he had much experience. I decided he needed a mistress. He was not going to ever be cock sucking faggot hesitating. I went up to him and told him that I knew he wanted to be a cum guzzling, cock sucking faggot. He was in shock. No one had ever said that to him. I told him I was sure anyone who knew him longer than a minute would know. I mean he was transparent. My guess was just no one in his life had called him out on it before. Women know. Some may not want to admit it to themselves that their husband or lover is a sword swallower or a butt pirate, but they know. I don’t turn a blind eye to a sissy or a faggot in need of cock. The world needs more cocksuckers. I led him to the glory hole room and blackmailed him into sucking dick. He just needed that push to do it. You can think about cock all day long, but how can you be a cock sucking sissy if you only think about doing it? You just need a phone dominatrix like me to take you from fantasy to reality.

Mistress phone sex

Mistress phone sex“I want the world to know what a sissy I am Mistress.” I look down on him with adoring eyes. “Is that so?” I start to pet his head. “You need the world to know what you truly are. Trust me I know.” “You are not the first sissy to come to me with a confession like this.” And I know exactly how to handle your craving of being ‘The center of it all whore.’ I walk across the room in my thigh high stockings and four-inch black high heels. Twisting around I face you. With my finger, I call you over to me. You crawl over on all fours as good sissies will do. You kneel before me leaning down and kissing my heals. I point to the right of you and see that I have you on live internet feed in your girly pink lacy dress. “Tell the world your name.” He spurts out “um, um… my name is Tim Mistress.” “Very good I praise you with.” “Now tell the world where you are from.” ” He looks at the camera and again spurts out “Texas Mistress.” His face blushes his dick rock hard his dream comes true.

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.

Foot Job Fetishes

Mistress Phone SexBesides being an excellent sissy trainer, I am also a mistress whom client’s employ to fulfill their fetishes. I have a client, Mark who has a tremendous foot fetish. He likes to schedule an appointment about once a month. To prepare for this appointment I go to have a pedicure. He likes my toenails to be a deep red and my feet to be extra smooth. He also likes them to be extra stinky, so I make sure that I wear my oldest running shoes without any socks and work out in them for an hour or so before his arrival. When he arrives, I am barefoot. I sit him on the couch and lay down with my feet facing him. He starts by rubbing them and then he starts licking and kissing them. Taking each of my toes completely in his mouth, running his tongue between each one. While he is licking one foot, I use my other foot to rub his cock over his pants until it is nice and hard. I then remove his pants and apply a nice slick oil all over his rock-hard dick. I take my feet and give him a foot job. He lays there and watches with big wide eyes. He doesn’t need to touch any other part of my body and never moves his eyes from his crotch, watching as my feet glide up and down on his hard shaft. I wrap my feet around it and move them up and down, grazing his balls with my feet as I go. When he is close, he lays back and I can see his eyes relax, that is my cue to start rubbing harder and faster, stroking him softly but firmly. Soon he is ready and grabs my feet around his cock and explodes, leaving his warm, thick cum running down my feet and in between my toes. Then he takes my feet and licks his cum from them, between my toes and even under my toenails before scheduling next months appointment.