Category: Sissy humiliation

Sissy maid training Rob

Sissy maid trainingI think I might have a new sissy go play with. Her birth name is Rob but I’m thinking of a new and more appropriate name. She is an eager, sweet, sissy with a baby face and a head of beautiful light red hair. I have already bought her a sexy maid uniform and a slutty hoe dress to wear when going out. Like right now, she’s face-timing me as she sits in a park. Dressed like a good slut and sucking this stranger’s cock for “tribute” and confirmation to what a good sissy slut she is. The stranger had his fingers in her hair using her throat like it’s a flesh light. My sissies eyes watering and making her mascara run as she gags around this strangers cock. It’s so much fun, she is almost like a puppy. So eager to please even while being abused.  I can’t wait to see just how far I can push her and how much money I can make by making her my whore.

Sissy maid training week 2

Sissy maid training

My husband is doing well with his maid training. He is learning in more detail how I like things done. We’ve been married for a while but typical guy never paid any attention to how things were being done. This irritated me a lot at first, and I have kept him in the cock cage. He hasn’t protested but I hear him with morning wood straining….ha ha ha ha.
I attached a fun furry tail to a butt plug. I thought it was hilarious and humiliating to put a butt plug up his ass then a tail on it. Watching him walk around the house is just pure entertainment.
Every once in a while I will make him bend over in front of me so I can pop it out then pop it back in. His little cock gets so hard, pushing out from the cock cage like an overstuffed sausage. A week and counting… I am wondering how long it will be until he comes to me, begging to have the cock cage removed. I haven’t thought about removing it so I think it will be a while.

You are my toy and I am your Goddess

Sissy humiliation ClarissaI think my name Clarissa should be added to a deities list, because I am a master at sex with my beautiful and bountiful body. My breasts are voluptuous and my ass is round and rock hard back side can drop up and down to make any man cum in minutes. My mouth is a wet hole of luxury and finesse. I know just how to suck a mans dick, where to flick my tongue and how fast or slow, how hard to grip when to slow down, when to speed up and exactly what to do to make it rainy sticky sweet cum from that tip. I can be your fantasy and hook you with just one smile and look from my hypnotic eye, and after I hook, line and sink you, I will throw you away and move on to the next. Why? Just because I can. I am a goddess, a goddess of love and sex and deserve to be worshiped.

Little Dick Gary

Small dick humiliation Envy

I have a client name Gary. LOL! I’m trying my hardest not to laugh as I write this… Gary has a really small dick, a real micro-cock. It’s 2 inches when it’s hard. I like telling him he should have been born a female because his cock is like a big clit. The poor man has never pleased a woman’s pussy. He can’t even keep a girl once she sees his small package. He likes to get dressed up in women’s clothing…dresses, makeup, heels, and a wig. He has me call over a couple of male friends with huge cocks. He always says he just wants to compare his little cock to their huge cocks. But he always ends up on his knees with a mouth full of dick. My ribs hurt from laughing at Little Dick Gary.

Mistress Envy

Domination phone sex Envy

 

Call me Mistress Envy. Let me control you. I want to dominate you. Worship at my feet. Obey or be punished. I’ll make you bend over and I’ll spank your bare ass red. In my dungeon you’ll wear a leash, because you’re my pet. You won’t stand on two feet, you’ll crawl on your hands and knees. I like my pets to dress up. We’ll put you in a gown and makeup. Let me make you pretty. I’ll even give you a girl’s name like “Sara or Cindy”. If you have a small penis let me humiliate you. You know with a dick your size you’ll never be able to satisfy a woman. I know what you crave. I know what you need. Please me and be rewarded. Disobey me and I’ll show you pain. I’ll drink your tears, my pet.

Sissy maid training for hubby

Sissy maid training

I have decided to train my sissy hubby as a sissy maid. I got him a maid outfit complete with stocking, panties, a bra and a little maid hat. I told him he would be wearing this for training and I would decide if it were to be his standard uniform when in sissy mode, so to speak. I hand it to him and point to the bedroom for him to change.

When he comes out I laugh at what a candy ass pussy bitch he looks like. “Oh what an interesting sissy maid slut you make, let’s get you to work you faggot.” I said and he didn’t seem to know where to start. “What’s the problem?” I asked and as I thought, he didn’t know what to do. I said simply to work from highest to lowest.

A few hours later he came to my den where I was working and told me he was finished. “Get on your knees until I come back from inspecting it.” I said to him “there was good and bad news. Good news it isn’t horrible, bad news is you didn’t try that hard. I think until I get a better effort, you will be in a cock cage. As a reward for a good first time effort I am going to let you lick my pussy.” A grin came across his face until I said he was going to lick my pussy after I’ve put the cock cage on.

He loves licking my pussy but of course the cock cage made it uncomfortable. He flicked my clit with is tongue and slid 2 fingers inside me, I had been horny all day and relaxed into it and came all over his face. He looked like a glazed sissy donut.

Next time, he learns what else a sissy slut in training needs to know. And why he suddenly has a tail?

Pathetic Small Dick Surprise

Small dick humiliation LenaI’m a beautiful, sexy, sophisticated woman and when I go to hook up with someone for the first time, I expect them to match my needs in all ways! Nothing is more frustrating than getting between the sheets with a hott sexy man only to find that his cock is a pathetic tiny little sausage! This golden pussy wasn’t made for just anyone! It’s a gift, a reward, a very special achievement! If a man even dares to think that I will accept anything less than a thick, delicious, huge cock inside of my goodies then he is in serious need of a reality check! I brought home a tall, sexy guy from the club the other night assuming his dick was going to be up to par. Boy was I wrong! As soon as we got home we went straight to the bed and undressed one another only to find that his puny little four inch cock was like a chewed up piece of used bubblegum! Fucking disgusting! I started cracking up and made him lay there on the bed while I snapped pictures to send to my friends so that they could see what a monstrosity his small dick was! He was humiliated that I didn’t think highly about him, and tried to cover himself up with his clothes. I had to give him a harsh reminder of how delusional he must be to think he could fuck such a hott and naughty trophy like myself! Pathetic!

Be a bad sissy, to be my good sissy bitch

Sissy Humiliation ClarissaHave you ever had a sissy that did so well you did not have anything to punish them for anymore because they were such a good little bitch, you just cannot punish them. One of my sissy maids is so perfect and does everything that I say that I just cannot seem to find anything to punish him for, so I have been having to make stuff up. I will punish him for licking my asshole to slow, when he was doing it just fine. I have punished him for getting saliva on my boot after I told him to lick it. I kind of feel bad but it is his fault he does exactly what I want. I think I need to tell him to disobey me so I have something to yell at him for and put his cock in a nice vice grip contraption. Its no fun if I cannot toture his cock and balls a little bit, but I want a reason to do so. I am ordering you to be a bad sissy, just to prove you are my good little sissy.

Sissy humiliation gets me off Part 2

Sissy humiliation

 

Officers crowded around the car were all hard and some were jerking off right there, some were rubbing their cocks on the outside of their pants. I looked around and pointed at the sexiest one in the group, and it was not my husband. This officer was over six foot and had the most well tones body. The V bar muscles across his hips and a nice big cock in his hands.
He took one look at my husband’s tiny dick and laughed. The officer took the dominant role with you easily and said “Don’t jerk off while I fuck her or I’ll cuff you.” He slid his perfect cock inside me and I let out a loud moan and all the guys seemed to physically respond. Some started jerking off even harder. I said “Now don’t go cumming officers, unless you are going to cum all over my husband after you fuck me.”
As my husband watched, each officer took a turn fucking my sweet fuckhole, and then he would pull out to cum on my husband. I could see the expression of humiliation while the officers were shooting big loads onto his face and making it drip off of him.
Each officer had taken a turn, and they all seemed satisfied, my husband covered in cum. Home is only a few blocks from the police station, I tell my husband to enjoy the walk home…covered in jizz. Feeling satisfied upon getting home, I got comfortable on the couch and waited for you to get home. Your look was priceless, total humiliation.

Sissy humiliation gets me off

Sissy humiliation

Trying to get to the fundraiser on time, and thank you to pathetic husband, we are now waiting for a ticket for doing 33 mph over the speed limit. As the officer approaches the window, I tell the cuck to let me handle it. I see the officer and he is gorgeous. The sissy put his window down, and as the officer bends down to say “do you know why I pulled you over?”  he stops mid-sentence and smiles at me. “I love hot sexy women, and you smoke.” Completely ignoring my husband. That turned me and my cucky on.  I ask if I could get out of the car and speak to him. He comes around to my side, and as I am stepping out I tell my husband to stay in the car this is not for sissies. The officer looked at me up and down in my formal dress and licked his lips. “Officer, can we have an escort to the fundraiser? Tomorrow I will show you what it means to me.” He did just that….

The next day I had the sissy dress in panties and a bra under his clothing and drive me to the precinct. We met the officer in the impound lot attached to the building, he came out and I was already wet knowing what was going to happen. He walked toward me, all muscle, unbuttoning his shirt and removing his bullet proof vest. He walked right up to me, grabbed me around the waist, picked me up and laid me on the hood of an old police car. I had a skirt, no panties and no bra, and a halter top. My nipples were hard as rocks as soon as he touched me. He had my legs in the air, eagerly licking my pussy and saying how good my pussy tastes. I was so ready cum, foreplay was unnecessary. He pulled out his cock and it was perfect. I smiled and said “Fuck me hard.” It felt so good when he thrust into me I couldn’t help but let out a healthy moan. “Sissy, come watch how a real man fucks.” The officer smirking as he yelled to him. The slave came and stood next to the car and I could see he was hard watching this stunningly handsome man with a big cock fucking me. The officer laughed and asked my slave if that was a big clit.” I laughed and said “Yeah, small dick humiliation just makes him hotter.”

The officer fucked me in every position you could think of to do on the hood of that car. I was so into cumming repeatedly and in my own world, that I did not notice a crowd of even more gorgeous men, gorgeous officers…all in uniform have crowded around the car.

Come back next week to find out what happened next…as if you don’t already know. *smirk*