Tag: sissy humiliation

Sissy maid stories: the cock, the cage, and the plug

Sissy maid stories

I’ve been having so much fun training my sissy maid. It’s becoming my favorite activity next to fucking you.

Of course with our new little toy you’ve gotten a lot more attention to your cock.

Like right now. I was enjoying the site of our little sissy maid on her knees. Wearing a latex maid outfit that left little to nothing to the imagination. Her little bitch clit throbbing in its cage as it tries to get hard. I giggle as I watch it, poor pathetic little thing.

Her cock was in your mouth.  She was fucking her own throat with such vigor that you couldn’t help but lean back, your eyes rolling into the back of your head. A pool of spit on the floor between you, our sissies tears ruining her makeup and her bright red lipstick was smeared all over your cock and her mouth.

I pressed the button to the remote control vibrating jeweled anal plug in her pussy and watched her quiver. She moaned around your cock making herself gag and try to pull off of your cock. I giggled as you grabbed her by the hair and forced her back on. Fucking her mouth with short hard thrusts until your groaned.

She was quivering, her hands open and close, Gagging and choking around your cock as you force your cum down her throat.

When you let her hair go she pulled back, coughing and gagging. Tears streaming down her cheeks as she gasped for breath. When she got some control again she swallowed hard and looks up at you. “Thank you sir.”

The Best Phone Sex is Sissy Humiliation

best phone sexThe best phone sex for me is with sissies and cuckolds. Why? Because I get to be a mean bitch. Over the weekend, I met this man. We actually went to college together, but lost touch over the years.  Face Book reunited us. I agreed to meet him Saturday for drinks. Attractive man. Educated, articulate, nice and a wealthy.  Just not very masculine. I figured his more feminine voice and mannerisms were from low testosterone, which usually means small dick. I was right. He had a 2 inch willy at best. When I saw it, I burst out laughing. The gall of any man who thinks he can fuck me with a shrimp dick pisses me off. I gave him a healthy dose of sissy humiliation that began with putting him in a pair of my panties. Anything less than 5 inches belongs in panties because it will swim around lost in boxers. I am a sissy trainer. Sometimes guys come willingly to me for help on becoming a sissy, sometimes they need nudging like my college pal. He was an old friend. I couldn’t delude him into thinking he had anything that could please a woman.  That’s just setting a man up for failure. Sissies can become a very integral part of a woman’s life if they just get a little training and accept their fate. The sissy training began with panties and an honest conversation about cock size. We discussed ways he could still please a woman without actually fucking her since that would be no pleasure at all. During training, he couldn’t stop rubbing his nub. I smacked his hands away from his dick several times before I put him under lock and key. Sissies are here for a woman’s pleasure.  I only allow a sissy to touch his willy as a reward for something quite remarkable. My sissy in training can barely lick my pussy. Until further notice, he is under lock and key. I love being a sissy trainer. He will learn to worship my pussy eventually. At least if he ever wants to touch his dick again, he will.

sissy humiliation

Felecia is a Hot sexy woman!

Hot sexy woman

This Hot sexy woman wants her tight pink honeypot licked till she screams! Look at how juicy and wet my pussy is! Come on you little cucky, I know you want to lick my freshly fucked pussy. There was a great big thick cock inside of me. It was 10 inches long, and so fucking thick I could not wrap my hands around that thick cock. Look at your little tiny cock. I have seen bigger clits than that tiny thing. It’s dripping! Look at how pathetic you are! Your tiny cock is dripping and drooling for a big thick cock that has been in my pussy. You must be a little cock sucking sissy slut! I bet you would rather have that nice big cock than this freshly fucked pussy! You are such a little dick loser! I am going to wrap my legs around your head and make you eat my pussy till I cover your sissy slut face! 

Ready 4 Ur Humiliation?

sissy humiliation

I bet you still got that tiny ass cock don’t you? That’s okay; I came prepared this time since you disgraced me last time when I saw how puny your clitterdick is. I’ll tell you what I’ll let you do though! You can watch a real man fuck me up the ass like you wish you could do. Maybe he could teach you a couple things while you use your thumb and index finger to try to rub that tiny cock of yours. Unfortunately, I could never let you fuck me with that stub. No woman will allow you to fuck her honestly, but at least you get to see how a real man can use his cock to please a woman like me. My favorite kind of cock is a big black veiny cock! Once you go black, you can never go back baby. Nothing against you… you just don’t have the rhythm or the right size tool for me! I only take cock from REAL men and can’t help but laugh and relish in sissy humiliation! Sorry loser.

Sex Therapy Needs a Second

Tease and DenialI received a call from a true sissy today. He wanted to get off, but he couldn’t without guidance and a helping hand. I got some help from my new young friend, Trudy, who came over and gave me a hand. I had Trudy help him dress in some frilly girls’ underthings, with a cute little design on them. Then, I had her lead him around the floor for a minute, to see how well he could listen. He obeyed commands very well, so I let her have him eat her puss. I, of course, stood behind Trudy and played with her beautiful, perky tits while he did it. I talked him through various spots to hit, ways to lick and nibble and suck.Sexy chicks

After that, I let her climb on his back and I had him walk her around the room a couple of laps. When he finally got good and worn out, I had Trudy tie him to the table and work her magic on his cock and balls while I stood over his face and let him stare at my puss. I leaned over and took Trudy‘s face in my hands, and I kissed her deep, tasting his cock and balls on her tongue. I had her stand over his face and let him eat her sweet young pussy out for a bit, while I drilled his tight little asshole with my magic wand. When all was said and done, I let Trudy ride his hard cock until she achieved all the pleasure she could handle, denying him the right to cum until she was done. When he did come, it was with my wand massaging his prostate and Trudy‘s cupped hands catching every drop. I made her feed it to him before he was allowed to get back up and take his leave. Sissy humiliation

Can you handle me?

Sissy humiliation

You want to be my sissy you have to prove it. I want pictures of you sucking on a big fat black cock, I want pictures of you in women’s panties. I want it all. My real life sissy’s understand that Sissy humiliation is just as fun as being forced to put on make up, women’s clothing and prancing around like the sissy you are in public. Humiliating my sissy and watching her prance around worshiping me makes my pussy wet. I love creative sissy’s! I love music and my sissy’s all have to sing to me. Sing to me about how you love to suck big cock because your tiny cock is like a clit! Little dicks like your’s makes me giggle. You can bet I will post every single photo you send me!! 

Sissy is forced to take a big cock in that sissy pussy

Ass fetish

You should have heard this pathetic sissy faggot crying the first time he had a cock put in his ass. He didn’t know he was such a dirty little pathetic sissy faggot until I convinced him that he was. He came to me a powerful ceo of a major company. He was in charge, but at home he was weak. He wanted to learn how to stand up to his wife and him be a man. I told him to stand up. We started working on powerful breathing technique. He was deep in thought when I grabbed his little tiny cock. His eyes opened wide and he turned to grab me and kiss me. I squeezed his tiny cock and laughed at his discomfort. I told him to drop his pants, he did like the good little bitch that he was. He seemed proud of his tiny little pathetic sissy cock and his tiny little balls. I squeezed him again and whispered in his ear… This is the reason why she walks all over you. You have a tiny worthless little cock. I bend him over my desk and made him spread his ass cheeks apart. He knew what he was, he knew how pathetic he was. He moaned as I slid my fingers up and down his sissy asshole. He pushed his ass against my finger and he moaned. He asked if I had something bigger. I sure did. I brought in my male secretary. I pulled his big black cock out, covered him in lube and told him to fuck that dirty pathetic sissy pussy. Listening to him cry because of how big it was will teach him not to ask for more than he can handle again.

Sissy Humiliation

sissy humiliation

I am a switch – I go from the best girlfriend to the best sissy training phone sex princess ever. I’ve been very focused on humiliating my new favorite loser. He actually used to follow me around in high school, such a creep. Now he’s came crawling back to me, but for lessons on how to be a sissy whore. I was more than happy to help, and I’ve been spending all morning perfecting his sissy maid training. He had to really max out his credit card to make me happy! I bought him and myself tons of whore clothes, and makeup. Let’s not even get started on the shoes! I only had to make a few phone calls and my friends were there to humiliate, and of course fuck his tight sissy ass! He honestly tried to tell me he’d never sucked dick before, and never even had one in his ass. I knew he was full of shit though! Soon he was my bitch, and loving every second of it.

Sissy humiliation with Felecia

Sissy humiliation

As your therapist I urge you to let it out. Be honest with yourself and admit what you are.. You have been searching for tranny porn at trannyphonesexchicks.com .. you know looking at all of those big tittied women and their big thick tranny cocks makes your tiny cock drool. Don’t look at me like that! You know damn well that your cock is getting hard right now just being exposed a little bit.. I know you are a tranny cock lover… but we need to get to the bottom of your love for tranny fuck whore like those.. I think we both know that you want to dress up in those sexy clingy closes just like women. You want your hair and nails done.. but you want to suck big thick cocks of strong powerful men.. Just like most men who have big corporations you are really a little dick bitch who wants his ass pounded by strong men. Now how should I tell your wife that you are a sissy cunt.

The Best Phone Sex is Sissy Humiliation

best phone sexThe best phone sex is sissy training phone sex. For me it is at least. Maybe not so much for my sissy callers. You see I make sissies prove themselves. Nothing annoys me more than fantasy sissies. I want my sissies to do humiliating tasks and send me photos. I want to know they are really wearing women’s panties because I prefer real sissies. I train my new sissy callers to my particular tastes. I love sissy humiliation, so every new sissy caller has an embarrassing task they most complete before calling me a second time. My latest sissy needed a lot of help. He gets high and gets sissified. He always insisted that if it were not for some high end cocaine and pharmaceutical Mary Jane, he would never have sissy thoughts. Bullshit. We all know that when you are high or altered your freak flag flies high. That is when you are at your most honest. You do not deny yourself feelings of guilt or let societal norms dictate your behavior. So guess what? If you are a sissy high, you are a sissy in need of a sissy trainer who will push you to be the perfect sissy all the time.

sissy humiliationMeet Katie, formally known as Ken. Her first task was to buy some pretty lacy panties. Her little clit stick would be lost in boxers. She had to be clear that she was buying the panties for herself, not a wife or girlfriend because women deserve bigger than an inch worm. Her second task was to write humiliating things on her feminine body like “tiny dick loser” and “I clean bull’s spunk.” Of course I needed pictures so I could post on my blog and know she was being a good little obedient sissy. I made her text the picture to ex girlfriends and apologize for not realizing sooner that size matters . I helped her pen an ad for Craig’s List to find a big black daddy to help her  hone her cock sucking sills.

Katie has come a long way in a few weeks. With her sissy trainer / phone sex therapist helping her, she will become the best cock sucking sissy faggot out there. Do you just need a sexy no nonsense sissy trainer to be the best sissy you can be too?