Category: Sissy humiliation

Sissy Maid Training with Gwen

sissy maid trainingI have so much fun with sissy maid training. I always keep your little cocks in a cock ring because after all once I make the transformation of turning you into little sissy girls you no longer have a cock. You have a pussy instead. Sometimes I like to dress you up in a maids outfit and shove a feather duster up your tight little puckered assholes. I tell you that you had better do a good job dusting and laugh as you are wiggling your ass trying to dust the coffee table. You knocked a lamp off of the end table and that just won’t do. So I have you bend over and place your hands on the coffee table. I have found that my riding crop always helps you to remember to be more careful. After a dozen of well-placed smacks on that ass. I start fucking your ass with the feather duster. You are begging me to release your cock ring and allow you to cum. But I don’t. Instead, I tell you to go do the dishes and leave that feather duster up your ass. Maybe if you do a really good job cleaning I will allow you to come…..only time will tell.

Foot fetish and a naughty sissy

Foot fetishes

My sissy hubby loves … and I mean loves anything foot related in sex. As a special treat for my hard working sissy boy, I planned something out of the ordinary.
My bestie sorority sister from back in the day came over to help me with this treat. We did our pre-evening shopping and had a blast. After setting it up I brought sissy into the bathroom, blindfolded. We sat him down, put his accessories on and removed his blindfold. He was sitting in a princess’s chair with a little tiara and a pink dress was all laid out for him to get into. He seemed pretty elated about what was going on and I asked the pretty little sissy if he was ready for his foot show. His face went from a huge smile to a frown rather quickly. I asked what was wrong and he said, “I am not allowed to cum My Madam.” I knew why, but I was just making sure slave was paying attention.
My bestie and I got down and dirty right away. We both just had silk robes on and we slid them off our shoulders. I reached over and flicked and played with her nipple and I could see the strain come over my hubby’s face. I sat her down on the sauna bench and put her legs over the front of me, just enough leg to be able to play with my nipples. The sissy’s cock cage prevents him from getting hard. I got up and pushed up his little pink dress and sure enough, stuck with cum everywhere.

The Way I Like My Sissy Bitch Bois

Domination phone sexThis is how all you sissy bitch bois should when not in use. All you bois are worthless little creatures. Some of you are good at being furniture. Some of you are good at eating pussies. Some of you are good at fucking. Some of you are good at being toilets. But you are all still worthless little bitch bois. I treat My animals better then My boi pets.  Bois in cages.  Bois on leashes.  Bois crawling around on all fours.  Barking.   Using the bathroom out side for all to see how worthless you are.  Hearing the mocking of the neighbors as you squat.  When I have a party bringing out for all my friends.  To be humiliated.  To be beat. And  to have your pussy ass fucked.

Sexy Dominatrix Gwen

sexy dominatrixYou called and arrange a session with a sexy dominatrix. I told you to be here promptly at eleven o’clock in the morning. It is now twelve and I have not seen or heard from you. I am starting to think that you have chickened out. Then my phone rings and you start making excuses for being late. Which is totally unacceptable. You should have called me at the time of our appointment not thirty minutes later. By the time you finally arrive you have wasted over an hour of my time. I let you know that you will be paying me for my wasted time and this is no longer going to be a sexy domination session, but instead a sissy maid training session. You will be paying for your naughtiness. I have you take off all of your clothes and then put on a super slutty maid outfit with crotch less panties, stockings, sexy high heel shoes, and last but not least some red fuck me lipstick. Then I hand you a feather duster and tell you to start cleaning. Every time you bend over I give you a hard smack with the riding crop. Before long your ass is covered in pretty little red welts. The door bell rings and you go to hide. I tell you you had better get back to cleaning my coffee table if you know what is good for you. I open the door and one of my luscious dark chocolate friends is standing there. He notices you right away and says well Mistress Gwen what do we have here as he licks his lips. You’ll have to call me to find out what happens next.

sissy maid training

Pretty Sissy

Forced feminizationI’m a madam, a female pimp, and I need a sissy that willing to do anything to get money for me. I’ll make you so beautiful that you’ll be able to attract any man. I’ll teach you how to do your makeup and hair. And put you in the finest clothes, because my hoes are high-class. The next step will be your sexual education, I’ll teach you how to suck cock, and how to accept huge cocks into your boy-pussy. We’ll make so much money you’ll be able to quit your day job. It’s going to be hard work. Sometimes you’ll entertain up to twenty men a day. You’ll get so much action your lips and asshole will be sore. The only rule that I have is that you must always remember that I’m the boss and I run the show. Any attitude or back talk from you means automatic punishment. Be a good hoe and we won’t have any problems.

Sissy Boi Wanda begging for Collar

Sissy humiliation Laughs. There is this sissy boi doggy bitch Wanda. Who begs every time he sees me to have My collar. He says he will do anything for My collar. I laugh as if that would be a choice for him to do anything for My collar. Of course he would do anything and he would beg and love to do what ever I ask. Sissy boi doggy bitch’s have no choice. Have no free will. Yet this small clit dick and his pussy ass begs Me as if he would have a choice in what he would do for Me. What a worthless sissy boi doggy bitch to think such things. My pets and I laugh at him. We have never seen such stupidity in such a worthless sissy boi doggy bitch before. If he did receive My collar he would be the animal the lowest of all the pets.

Gwen Likes Sissy Whores

sissy humilitation gwen

Life is good at the car dealership what started out as me having leverage has kinda just turned into a kinky game. I get to come and go as I please and still get my full paycheck, but I also get to participate in his kinky sex games. I have always been a bit of a voyeur, but for the most part, my sex life has always been more vanilla. Even having a side job as an escort my clientele has been pretty vanilla. My boss, on the other hand, is a very kinky nasty little man whore. Who knew? How most people see a life coach, he sees a professional mistress. She is like the life coach of his sex life. She dresses him up in little sissy girl outfits that make me giggle. She is pretty wicked with a riding crop and I have to say that the welts that she leaves on his ass make my pussy wet and tingly. I find it erotic to watch a man grovel at her feet while dressed in a pair of pink crotchless panties that she has wedged up his ass. I think I am going to take up sissy training and look I already have one here to practice on.

Girls on Film

Phone Humiliation

You invited me over for a “movie night,” but we both know that’s not all you had in mind. We made out as you groped my body and stripped me down. Spreading my legs, I waited for you to slide into me. I noticed you were already moaning though, so I asked if you already had your cock inside me. A little embarrassed, you said yes, but kept thrusting away.

I sighed, realizing tonight wasn’t going to be as fun as I thought it was, but figured you must at least have a few tricks up your sleeve for pleasing a woman. To my dismay, in less than two minutes, you grunted as a warm goo filled me up. That’s it? Really? I was pretty pissed, and you had nothing more to offer me than a shrug and stupid smile. You said we could finish the rest of the movie while you got ready for a second helping, but I had another plan.

I invited my friend over without you knowing and let her know all the details of your pathetic dick. When she got there, she pushed you out of the way and came to save my day by giving me some real fun! You watched helplessly as she made her way in between my legs and licked out all the cum you left behind. I moaned as I finally got some real pleasure. Pulling out a strap on, she bent me over and fucked me right with a dong of substantial size, unlike the pathetic worm in your pants.

You couldn’t believe that another woman was drilling your date, right there on your bed in front of you, and doing a better job at it, too! I finally found my release and squirted all over your bed. As we gathered our things and got ready to leave, you told me to wait because you were ready to go again and wanted a second chance to prove you could please me. Her and I both looked at you, scoffed, and went on our way without another word.

Small Dick Humiliation

Fourth of July Gangbang

Exhibitionist sex

So the party I had been planning went off with a bang! In more ways than one really, I got the gangbang I wanted and of course the bang from the fireworks.
I ended up having all the guys that came that wanted to be part of the gang bang putting their names on a list and then I just put them into groups so everyone could rotate and enjoy the food and the rest of the party as well as my pussy.
I can’t even tell you how many times I came, it was insane! I mean I’ve cum multiple times before, but never that much. I had big cocks all over the place and took every opportunity to suck each one before they fucked me. I was on a high all day. The best was a dp with a huge cock in my pussy and a big cock in my ass. All the guys around me playing with my tits, touching my body sent me into waves of orgasms. My sissy hubby, after the party was over came to my side, I had just finished the last gang bang of the night. I made him lick every inch of me to get all the cum off. Best 4th ever.

Be My Bitch

Forced Feminization

Come on, now. Stand up, drop your pants, and let me see that pathetic, shriveled worm you call a dick. Hesitantly, you do as I say, dreading what you know will come next. I laugh hysterically at how tiny your so-called cock is. You must need a magnifying glass to find that little thing! Get naked, bitch, I bark at you as you remove the rest of your clothes. I push you to the ground and call in the big, black stud I brought to teach you a lesson about being a man.

His meaty rod was as big as my forearm and was rock hard. I have him slip his cock into my ass, whimpering as it stretched out my tight hole and filled me deep. I tell you to get beneath so you can suck his balls and lick his asshole as he fucks me. Having the black guy pull out his cock, I hold your jaw open as he guides his BBC down your throat. Fuck yeah, taste my ass on that throbbing fuckstick, you little bitch! I laugh as you gag on his anaconda. You’re so pathetic! Just like that itty bitty pecker you’ve got.

Laying back, I spread my legs while the black stud shoves your face into my wet pussy. This is about the only way you could ever pleasure me; your dinky is too small to even feel inside me! The black guy gets behind you and jams his beefy meat tube into your ass, making you squeal like the sissy you are. I wrap my legs around your head to keep you from squirming too much while forcing you to keep licking my clit. The black man pounds you hard and deep as he busts a fat nut into your ass, making you a cum whore. You’ve been a filthy bitch today.

Sissy Humiliation