Category: Sissy humiliation

Sissy Humiliation from a Sexy Babe

sissy humiliationSissy humiliation is what you get when you call me with a pathetic pinky dick. Guys try to act all macho on the  phone, but I know. A cuckolding mistress knows a real man when she sees one and when she talks to one. Losers don’t ooze manliness. I understand that you are paying for a service, however, that is not a guarantee that you get to cum. Cumming is not a right, it is a privilege. A privilege of only the well endowed. So, you are asking yourself the painful question, “Do I get to cum?” If you have to ask, then no. Men with big dicks to pleasure a sexy babe like me, know they can get the job done. They are not second guessing their manhood. Only tiny dick losers and sissy bitches trying to act like men ever wonder if they got what I need. So if you don’t get to cum, what do you get? You get a lot of things actually. You get a wake-up call about your pussy status. You get to worship a hot fine woman by licking her pussy and ass clean of any and all cum left by a real man. You get to do humiliating tasks if I deem you sorry enough to put you in the sissy category. You will get your money’s worth, because you are pleasuring a hot woman. My pleasure and my amusement are what matters the most. Consider the $2 a minute an inconvenience tax for having to deal with your pathetic ass. You couldn’t get a hot mature woman like myself to even talk to you in a bar without shelling out far more money than that first. Consider yourself lucky that you have the option to pay to talk to someone like me.

MILF Phone Sex Women Love Sissy Humiliation

milf phone sexMILF phone sex keeps me pretty busy. There are so many young studs who know a mature lady is the best fuck. On and off the phone they know this. I thought I won the lottery when I picked up twin college studs Friday night. I sometimes go into this little dive bar near my house because it attracts the local college boys. Cheap drinks and cheap whores lol. Well, I am not cheap. I am rather sophisticated, but I love being a dirty whore for young guys and big cocks. The twins bought me shots all night and flirted like their life depended on it. Flattery goes a long way with me.

sissy humiliationWe got back to my place to fuck and I got smacked with disappointment. I thought I was going to be able to  take the “fuck brothers” off my bucket list that night. They were twins and so hard to tell apart, that was until they got naked. One boy had a huge cock, the other had a clit stick. One boy got fucked, the other got sissy humiliation. I don’t settle for just any cock. I know what I like. I know what I need. As his brother fucked me like the stud he was, I made loser boy kneel beside me and suck on my panties. “That is as close as you will ever get to my pussy, loser” I laughed at him.

cuckold phone sexClearly, he was shamed, but I could tell this was not the first time these studs had been in this situation before. In fact, I was pretty sure that the brother fucking me with a 9 inch dick was enjoying cuckolding his own brother. He even ordered his brother between my legs so when he busted his nut in my cougar pussy, his brother could clean me up easily. Kinky brothers. That really turned me on. The stuff that cuckold phone sex fantasies are made of, happened in my bedroom Friday night.

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.”

Stranger Fuck

Best phone sexI love how the gym is giving me this tight little body, and I can tell strangers can tell too. I have been getting hit on more and more. One guy came up to me the other day and I invited him over. I love knowing a complete stranger was coming over for me to fuck. I was going to make sure he got all of my pink little cunt. When he got there I led him to the kitchen where I was just wearing a apron, and his cock completely starting to throb. I bent over to get something off the counter and before I knew it his fucking cock was deep in my little tight asshole. He was filling me up so fucking deep. This stranger kept fucking me till my asshole was filled with his cum.

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! 

Cuckold Phone Sex: Tiny Clits Belong in Panties

cuckold phone sexCuckold phone sex is my favorite if you want to really know. Guys ask me all the time what I enjoy most about phone sex. When a tiny dick loser calls me, and I can hear it in his meek voice, my pussy drips. I love shaming little clit sticks. If you call me with a short dick, be prepared for humiliation. I will immediately size you up, well in your case, size you down!  Then, I will enjoy putting you in panties. You belong in panties. Boxers and boxer briefs are so balls and cocks have room to move; room to grow. Cocks can’t be in restrictive clothing because it kills sperm over time. But you don’t need to worry about that now do you? You should not be reproducing anyway. But the real issue here is your little dick gets lost in boxers and boxer briefs. Panties are for clits. Yes, that is what your pathetic excuse for a dick is; it is a clit stick. No worries about panties being too restrictive on a 2 inch dick. You will feel better in panties. Not a day goes by that I don’t put some loser in panties. It is better than a chastity belt. Any hot chick starts getting busy with you and she discovers you wear panties, she stops the action. Women don’t fuck guys in panties. We all know that if you are in a pair of women’s underwear it is because you bring NOTHING to the bedroom. Mature phone sex women know this better than young girls because we have seen a lot of cock in our lives. We have birthed babies and don’t have tight cunts like a coed, so we demand dicks we can feel. Length and girth matter; so if you don’t measure up, access denied. Get yourself some panties and enjoy your new role as a cuckold.

mature phone sexI am not the only cuckolding mistress here either, so check out our TUMBLR page to see all the other cuckolding queens.

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

Sexy phone chat with a small dick man

sexy phone chat

Okay so I have this girl from school that I have been friends with for a long while. Me and her are rather close and her man keeps hitting on me when she is in another room. Normally, I would always be down to be man stealer but I can tell he has a small cock.

Well in fact to clarify my thoughts more, my friend has always expressed it to me that he was not ever packing a big package. So every time he makes his comments and moves, I usually ignore it but not this time. This time if he wants to fuck around, I will fuck around with his tiny cock self.

He goes ahead and makes his comments so I call out to my friend and she rushes into the room. I slowly walk towards her and grab her face and start making out with her. I reach under her shirt and start playing and grabbing her tits in my hand.

“You see, you have not been taking care of her very good, you have a tiny dick- don’t you?” I mocked him. I know he was getting turned on but I never saw a bulge in his pants. That tiny I guess. His girl was moaning and enjoying my hands all over her body. I was going to make her cum over and over again.

See you can not do this to her can you? She needs a real mans cock, she is even getting off on a woman’s touch. You have some things to learn, so you can either grow a bigger cock with some supplements or you can dress up like a woman. OR I can get another man over here with a really fat big dick to fuck her right?

What’s it going to be?