Tag: sissy humiliation

Sissy Boy Gets Cuckolded

Sissy Humiliation

I love having a sissy slave. It gets me so wet to make him watch me get fucked by other guys, especially when they have big, meaty, black cocks. I made him wait on his knees as I leashed him in a pretty, pink, blinged out collar. Looking down at his pathetic, tiny cock, I frowned. Then, the dark meat arrived. I smiled as I pulled the sissy across the floor with the leash as I went to greet the chocolate hunk. When his radiator hose dropped from his pants, I couldn’t help but gasp a little. He laughed when he saw how tiny the bitch’s pecker was. We made him watch as he ravaged my body, tearing off my clothes and impaling me with his massive fuckstick. I turned back to see that the little sissy boy had turned a bit to the side, perhaps pained by the sight of me with a real man, so I grabbed the leash and pulled his face close. As punishment, I made him lick my asshole while I rode the chocolate thunderstorm. When he was ready to bust, the black man put me on all fours and blew his load all over my ass. With an iron fist, I forced my sissy slave to lick my ass completely clean, making sure he didn’t miss a drop of the cum.

Sissy cuck with PMS prissy man syndrome

Cuckold phone sex

I don’t really suppose cuckolding can be done with a dildo, but I’ll just do it anyway. My sissy hubby has been a super bitch lately. It seems like he is having PMS, prissy man syndrome, sullen, bitchy and no fun at all. When it was chores and panties time the other night he actually rolled his eyes at me and let out an exasperated sound at me. I wasn’t too happy about that, nothing in his sissy training has included giving me attitude. I do understand that his job is very demanding and stressful so I gave him a scolding and told him to keep his complaints to himself or I would have to dole out some punishment. He didn’t seem all that impressed either way and he went about his chores. A few hours later when he was done I told him I wanted to cum. He got onto the bed where I way lying naked stroking my pussy, he started licking my wet little fuck hole and clit without much enthusiasm. When I got tired of his half ass effort I told him to go sit in the corner and if he wasn’t going to do it right he could watch me every night for a month with someone else or a something else. That seemed to perk him up a lot and his cock got nice and hard. Finally the sissy I know is back….but I think with that behavior a punishment is in order.

Sissy Humiliation

sissy humiliationSissy humiliation Sunday? It is becoming a real thing with me. I think because yesterday was Mother’s Day, more guys than usual were getting sissified. Did you ever wear your mommy’s panties? One of the many things sissies have in common is a love for panties. On a psychological level, I think sissies know that their package is too small for boxers. The other thing sissies have in common is a small package. Did you try on someone’s panties when you were a little boy? The silk or satin, even cotton, feels good against a little nub. I bet if you tried on panties when you were younger, you popped a little chubby. Panty boys know that the closest they will likely get to pussy is wearing panties. With a little nub and a feminine demeanor, the best a panty boy can hope for is being a sissy. Women like me don’t give men with clits the time of day unless they pay us or we need a good laugh. Sissies do serve a purpose, however. Besides the small dick humiliation, they make great maids and pay piggies. One of the things I love most about being a sissy trainer is the fact that a sissy is so pathetic she will pay to be denied and shamed. Off the phone, I have a few sissies who pay me to clean my house. They also tribute me. I look at all money I receive from sissies as an annoyance fee. I need to be compensated for my time spent with losers. I am a hot MILF who can fuck anyone she wants, so time I spend with guys I wouldn’t fuck for a million dollars is time away from real men. On or off the phone, if you are a sissy in need of training be prepared to compensate me for my time. And, be prepared to do as you are told.

You Call That a Cock?

Small Dick Humiliation

You know what’s really pathetic? When you’re cock is so small, I might as well fuck a girl. At least she will have some titties to play with! In fact, you are so small, I think I will call one of my girlfriends up and make you watch how much better she is at pleasing me. When she gets there, I have her take off her clothes as I play with my clit. She is so hot, I can’t help but get wet. You try to join, but she just looks at you and that tiny pecker in disgust. Sit down, you pussy. Nobody here brought their magnifying glass, so you’ll have to sit this one out. Both naked, her and I press our soaking cunts together as we grind and moan. Every time her clit rubs against mine, fire stirs within me, growing bigger until it comes exploding out of me in a splash of cum squirting from my slit. Ready to return the favor, I lay in between her legs and lick her until her hips are bucking wildly. I could have been sucking your cock, instead, but it’s far too skimpy to have any fun at all with. When I shove my fingers inside her hole, she cums in a screaming orgasm, bursting all over my face. I happily lap it up as she comes back down. We scoff at you one last time before grabbing our things and leaving you alone.

Gear up for the Fourth Of July

Cuckold phone sex

I am gearing up for one of my favorite times of year… 4th of July. I love the 4th, festive and fireworks, parties and cookouts. This year I decided to turn it up a notch. So I had these pictures taken and I am having some flyers made for some sex clubs in the area. I want to have a huge 4th of July gangbang. I haven’t decided all the details but I know I want to be the center for every guy’s cock that shows up. Food, dips, chips and dicks! I’m even thinking to make it an outdoor tent event. With barrels of ice and beverages, a few grills and a center “stage” area where I will get fucked and fucked and fucked. I don’t think it’s too farfetched of an idea. The best part is, that my sissy hubby can have a perfect view of me getting slammed by multiple cocks, making me cum like he cannot. What if a hundred guys turn up! Should make for one of the best 4th of July holidays I’ve had. Oh and I think sissy hubby will wear a tiny red, white and blue thong the whole time, he’ll look like a pretty little sissy.

Exhibitionist sex

Sissy Humiliation with Our Site Sissy

sissy humiliationSissy humiliation is one of my favorites things to do as a phone sex woman. This company sees a lot of sissies too. No sissy is as pathetic as Sissy Michael, however. She is the personal sissy of our fearless leader, Mistress Levi. One of the many perks of this company, however, is the chance to shame Sissy Michael ourselves. I have quite the sissy fan base, but our site Sissy makes them all look butch in comparison.

sissy maid storiesSissy Michael or as I like to call her, Sissy Fairy Fag, even has her own website so anyone can call and shame her. If you enjoy sissy maid stories, I have plenty to share with you. Sissy Fairy Fag dress up like a princess, maid, pig, bunny and a baby, depending on her orders and mood. She has quite the sissy wardrobe. She goes out in public without shame completing humiliating tasks like buying panties and getting her nails done, even shopping for diapers. They might be humiliating to a real man, but to a pathetic pansy, they are embraced with glee.

best phone sexI have spoken with Sissy Fairy Fag on more than one occasion. She sings little sissy songs and relishes in telling her long history of sissydom. Sissy Fairy Fag deserves shame. First, she is pathetic. Not just for wearing feminine clothing and prancing about in public, but because she has a tiny little clitty stick. I could share photos of her shrimp dick with you, but you cannot unsee it. She frequently poops her panties too. Disgusting, I know. Not like she can’t get to a bathroom. She likes being teased for being a poopy pansy. Hard to believe, right?

sissy maid trainingThe best phone sex is not always pleasant, but it is enjoyable for the sissy. I love teasing and laughing at Sissy Fairy Fag. I also enjoy making her tell me all the humiliating things she has done in her life as a sissy. If you are a sissy, entertain me. I bet no matter how pathetic you are, you still aren’t as pathetic as Sissy Michael!

tease and denial

Boy Pussy

Forced crossdressingI love turning big, strong men into beautiful, weak women. Come over to my place for a real make over. First, we’ll start off by having you shave all of your body hair. Next, we’ll do your make-up. I’ll put eye shadow and mascara on your eyes. And I’ll put bright red lipstick on your lips and blush on your cheeks. Then you’ll be ready for your dress, let’s put you in something slutty. I have the perfect dress that’s your size, it’s a red, tight and super short. Can you walk in heels? Well, you better learn fast because I’m putting you in 6 inch heels. The final step is your hair. I have wigs in all colors. Do you want to be a dumb blonde, a classy brunette or a dirty red head?
When you’re all dressed up and looking sexy then it’s time for you to make me some money. You’re the hoe and I’m your pimp. Your job is to suck cock and take cock in your boy pussy. And bitch you better make me lots of money. When men come over to sample your sweet ass you are to stay on your knees. You are not allowed to stand like a real man. You’re my bitch and you are to stay on your hands and knees at all times. Now, be a good girl and answer the door our first customer is here.

Be My Servant

Domination Phone Sex
Today, you’ve been my servant all day; carrying my bags as I shop, rubbing my feet, picking up after me, etc. It is actually pretty pathetic how you jump at my every command, like a dog, so eager for my approval. Come late afternoon, I find myself with a strong need for a more frisky kind of fun. Getting into my corset, I grabbed my crop and demanded you get naked immediately. Of course, being the sissy bitch you are, you so exactly as I say without so much as a question. I pushed you down onto all fours and smacked your ass hard with the crop. My pussy got wet when I saw how red the mark was on that ass. You may be a worthless slut, but I can still have such fun using your body. Over and over again, I smacked your cheeks until they glowed red and radiated heat. Your ridiculously tiny pecker stiffened. I’m sure you’d love for me to suck that shriveled worm, but instead I smack it with the crop before I tell you to lay down flat on your back. Riding your face, I buck my hips and moan. I’m not sure if you can even breath under me, but I don’t care. Your only purpose is to please me. Cumming all down your face, my pussy squirts as I scream and moan. After I’m done, I get up, grab my things, and leave without another word, leaving you with tiny, blue balls.

I’d Rather Fuck a Girl

Sissy Humiliation

Things were getting heated between me, you, and another girl. It was going to be a threesome, but once your pants hit the floor, both of us burst out laughing. Your cock, although fully erect, was so miniscule and pathetic, it wasn’t even worth another notch on my bedpost. It was almost an insult that you even thought to come try and please the both of us voluptuous hotties with that enlarged clit you call a dick. You ought to be taught a lesson! In fact, I’d rather fuck just the other woman here than include you. It’s so small, it would be just like fucking another girl! We made you watch as she kissed my neck and squeezed my big titties, which is something you’ll never get to do. Rubbing my clit, she kissed down my shoulder before turning me back around so she could suck my nipple. My pussy ached for her touch as she licked my tit. You tried to come up and play with my clit with just your hand, since your cock was such a disappointment, but I swatted you away. I wanted no part of you, you pathetic bitch! Her and I licked and fingered each other until we both had cum over and over again, making you watch every deliciously erotic second of it without letting you so much as touch us. Tough luck!

ISO a full time fuckbuddy

Shaved wet pussy

Do you have those days when you are just feeling nothing but horny? You can’t get it off your mind no matter what important crap you have going on in life. I am that way a lot of days. I can’t seem to get enough fucking. My sissy hubby doesn’t do nearly enough to satisfy my pussy so I cuckold him and try to find all the cock I can handle. I’d really like to find a guy who can come and fuck me every day. It’s a fantasy to know I don’t have to “find” someone each time; he’d be at my beck and call. *Ding* phone text, come fuck me, please! Hoping that is all it takes and he is there playing and fucking my tight little fuck hole. Coming over for quickies would be a definite must have as well. Sometimes I just need to feel a cock inside me, the force of a man thrusting his big hard throbbing shaft inside me.