Tag: humiliation phone sex

You want the best sissy trainer don’t you?

best sissy trainer“You want the best sissy trainer don’t you sissy?” I asked my latest little sissy whore and she just shyly shook her head yes while looking down at the floor. “Well if you want the best, you have to be prepared to work hard, now don’t you?” Sissy had nothing to say to that, she was far too embarrassed about how she reacted to having to suck her first dick. She was so rude to the poor man that was actually paying to get his dick sucked and I felt so bad for him that I almost did it myself! You all know that I don’t ever stoop to paid work like that I just collect money from the whores that do but this little whore was making me look bad. She refused to suck his cock until I got so mad that I threatened to drop her as a sissy. I told her that if she didn’t suck this poor man’s cock and give him his money’s worth that I would never see her again. She didn’t want that so finally, she sucked his dick. Once she started she was into it just like I knew she would be, she even swallowed all his cum too like a good girl.

Milk machine torment

sissy phone sex

I love seeing my heels against your face. Your little clitty is so hard when I’m rough with you. I have lots of fun toys. I want to tie your pretty little self up and hook you up to my milker. I want it to suck and tug on your little clitty and milk you dry! I love using my milking table. Strapping you in tight with all my restraints. Pulling out my fun little prostate vibrator and rubbing your p-spot while i have my milker turned to max, not letting it up as you cum over and over again begging me to stop. But you and i both know i won’t do it, i am gonna milk that little bitch cock dry until you beg and break down using that safe word.

Enjoy Cum Whenever You Want

Taboo phone chatI bet you are a cum eating little whore, aren’t you? Well, then you are going to love this! The one thing cum whores love is finding ways to enjoy cum whenever they want. Especially around others who are none the wiser. I do say cum should never go to waste and now no cum needs too. It is so simple! Simply take any cum and freeze it! You can mix in a little water and cum and make your own cum ice cubes. They look pretty much the same so no one would ever know. But you will know, won’t you? Now you can be a cum guzzling slut anytime you want and around people who don’t know what a little cum whore you are. Isn’t it so much more enjoyable to do naughty things right in the open?

Mistress Francis is Watching You

Mistress Phone SexSissy PantiesHey, my little sissy slut. You wearing your sissy panties like Mistress Francis told you to? You better be. Now let us play. I want you to pull now your panties and play with your little clitty. Rub it nice and soft and see if we can get that little thing to grow just a little. I can imagine you are moaning a little now, are you not? Ok now when your clitty starts to leak I need you to stop. Very good. Now go grab that big fat dildo from your toy drawer. Oh, that is big baby. Rub that little clitty leakage all over the tip, just like that. Now stick your sissy ass up in the air, spread your cheeks and ram it into your man pussy. Do not be gentle and do not go slow. I want you to force it in there. Yes, like that. I imagine you look so cute with your panties around your ankles, your clitty leaking and that big thick dildo sticking out of your man pussy. Now you little cock slut I want you to ride that dildo, taking it deep and fast. Keep going. I see your clitty leaking again and you are moaning so loud. Now stop. Oh, you look so sad. Did you really think that I would let you cum that easy? Of course, I would not. So, my little sissy boy, you put everything away and do not touch yourself again until Mistress Francis gives you permission. And remember no touching that little clitty either or I will know, and you will be punished.

Forced Sissy Training Femdom Sessions

Forced sissy training is what this young man got. I found this young man sneaking around the back of my place where my bedroom window is. It seems he found himself some good jerk off material in watching me. He has been positioning himself under my window and watching me undress and masturbate. Some nights he got lucky and got a hot porn movie to himself. Me taking three big black cocks for a couple of hours. We fucked and we fucked good and long. I heard him outside and made him bring his sweet candy ass in. I found this to be my best friends son. She has told me he has been being weird lately and now I know. I decided that he needed to put on my panties, some stockings and even a bra for me. I painted his lips and told him he was officially my Bitch and I would train him to be right. I let him know that he was going to be forced to please dick and that meant to dress for that dick too. He was to come to my place nightly and come in the front door. He is to dress in whatever women’s clothing I leave out on my bed for him and he was to be prepared to be a part of the show. I trained him to suck that BBC and yeah, it was forced at first. Soon enough I knew he would come around and be the big dick sucking tramp he is currently.

Forced Sissy Training

Humiliation Phone Sex Gone Wild With Remi & ZOey

humiliation phone sexRemi And I had the pleasure of Giving the sexiest and best Humiliation phone sex to date. Now Remi Might look the sweet innocent little bombshell but she is a master of humiliating guys and gave me a run for my money recently.  Remi Has no Patience for men who aren’t hung like a fucking horse. ????And I Enjoy the biggest of black cock, so we put two and two together to make a pathetic little shrimp dick explode for us! We had this Bodybuilder who was cursed with a small little weenie that he hid in his underwear since before Highschool. I don’t know about you but if you shower with underwear in the locker room you have a little something to hide! Well, Remi and I descended on this confession and had our Macho man with the little hot dog kiss and suck our feet and Then brought in the big guns. Tall, handsome, well-hung men that even in their underwear couldn’t contain the girth of those cocks. Remi giggled and was just a tad mean ????as she made our small cock victim suck and slobber all over enormous cocks. Our small-dicked man enjoyed our laughter and comments about his lack of penis size. We rubbed our feet all over his face and made him worship us like the best sissy trainer duo we are! Come and get your humiliation on!????best sissy trainer

Sissy Phone Sex with Your Wife and Mistress

sissy phone sexSissy phone sex is still popular. Maybe even more so than ever. Last night, I had a real treat. One of my regular sissy girls called me with his wife. Most of my callers are in the closet. On the outside no one knows they like sucking cock and wearing panties. This sissy was busted by his wife riding her dildo when she came home unexpectedly from work one day. At first, she was disgusted. She thought perhaps she married a fag. I am not saying she didn’t. The jury is still out on that one lol. She just needed time to adjust to the fact that her husband was a cross dressing sissy. The more she thought about it the more she realized having a sissy is the best accessory a dominant woman can possess. We share sissy slave training duties with him. Until last night, I had never spoken to her. In fact, I thought it was likely my sissy lied or embellished about her involvement in his training. Turns out he was being truthful. She is furloughed from work until this virus has quelled some. That means more time on her hands to play with her sissy husband. We took turns last night shaming and humiliating his little clitty. I enjoyed sharing him with his wife. She pegged him too. I knew that was real because I could hear the whimpers. Made me wonder if when he is fucking his back door pussy with a dildo on our calls, if he is really doing it. He never sounded like that on the phone lol. My guess is my sissy bitch is sitting on an inner tube today. A sissy can never have enough mistresses in his life. Although online sissy training is all some sissies can have, the best scenario is a phone mistress and a real-life mistress. Together two sissy trainers can create the best sissy ever. 

Such an eager little pet… at first

best sissy trainerMy newest pet was an eager little whore for sure, he messaged me all the time and begged for my company like a little puppy begging for a treat. He practically humped the computer when he was looking at my pictures and he obeyed my every command. But here lately he has been missing in action and I am very disappointed. This little beta boy bitch needs to remember who his Master is and that is ME! I don’t care about his wife, I don’t care that she is cheating on him, that is her right and he needs to deal with that. All I care about is that he continue to worship me as I should be worshiped and if he is going to be a slacker in that regard I will drop him as a pet and leave him with no Master at all. Is that what you want my little beta bitch? You have disappointed me, do not let it happen again or the consequences will be harsh!

Sissies Need Humiliation Phone Sex

Humiliation phone sex

Humiliation phone sex sessions are a naughty sissy’s worst nightmare, or biggest rush. Look at this Sissy! She is so pretty and I think she needs to suck a lot of cock so she can get some fake titty implants. She looks pathetic with those stick on tits. I think Sammy needs to be teased more because those things are meant to stay covered. Look at them! They don’t even match her skin tone. I know how badly Sammy wants real tit implants so she can be a pretty girl. How do you feel about my idea to make her whore herself out for guys to use? I personally think she needs to start working it for free. She needs to visit glory holes and suck dick. Cover those titties up with pretty lingerie and wear some silky stockings. Once this sweet sissy looks pretty with the whore red lipstick on then we will see about her earning those big breasts she so desires to have. Sammy has a nice physique and pretty face so she is a easy one to transform. I am the best sissy trainer for Sammy and she is such a good student for me. I directed her to buy some toys and lingerie to assist her along in her sissification and she will be reporting back to me with all pictures of her shopping.

Best Sissy Trainer

I Have a Dildo For Your Man Pussy But You Have to Earn It

Mistress Phone Sex

Look what I have for you little sissy boy. A big thick dildo. Know what I am going to do to you with it? I know what you would like for me to do with it, but you are going to have to earn it first. I am going to sit right here on the edge of the bed and watch as you get this strapping big dick stud ready for me. You suck him nice and hard and take his dick in deep. I will let you keep going until you can taste the precum and then I will take him away from you. You can watch as I spread my legs and this fat cock fucks my bald juicy pussy and pumps it full of his warm yummy cum. When we are done, I will let you lick his cock clean, do not forget the balls love. Nice. Now come here and clean out my pussy, getting every last drop of that cum out of me. Oh, my sweet sissy you have done so well. Now pull down your sissy panties and let Mistress Violet ram this big fat dildo deep inside your man pussy. Let me hear my little cock slut moan as I fuck your man pussy with it.