Category: Sissy humiliation

Forced Feminization

Forced Feminization

Forced Feminization would be both a dream come true and his worst nightmare depending on how he looked at it.  Bill was known as the strongest man in town as the Sherriff, but he had a dark dirty secret.  He was the town’s biggest sissy in training with Mistress Glinda.   He lived every day in fear that his secret would be revealed, and he would be outed as being the little sissy that he was.  

Every Friday night Mistress Glinda would invite over friends to share in the humiliation and degradation as he was forced to wear the French Maid outfit and serve cocktails to the ladies.   The ladies loved to see just how far they could push him especially about his little cock. Each week after the guests left he was either rewarded or disciplined based on his behavior that evening.   He understood his place and always bowed down to Mistress Glinda no matter the outcome.

Sissy Humiliation: Richard Needs To Come Out of the Closet

sissy humiliationI love to give Richard sissy humiliation. He is a pathetic sissy boy with a tiny white boy penis. See the cock I am sucking in this picture? Richard wishes he was half as big, LOL. I love chatting with Richard because he is such a girly sissy. Plus, he knows size matters. Richard is a black cock faggot. I think he has always been one. He admitted to me that he let a black neighbor man fuck him silly when he was just a young teen boy. How hot is that? I think many white men try to be straight. Family approval and fitting in with their peers matters so much to men at a certain age. But Richard has had a series of failed relationships. That has to do with his itty bitty clitty though. Although, he does love to cross dress. He has such a fem body, that when I saw the pictures, I thought it was one of his ex-girlfriends at first. I mean I think Richard was born in the wrong body. I think he just needs to barge out of the closest and let everyone know he is a sissy faggot who is addicted to those monster black cocks. They the only things that make him cum. Likely, the only things that made his ex-girlfriends cum too. He needs to be out of the closet.  When women find out he likes to dress up in their clothes and a be a bottom bitch for a big black dildo or the real thing, they have zero respect for him anyway. It is only a matter of time before he sabotages another relationship by dressing up in her lingerie and admitting his need to be dominated by black bulls. It is only fair to the women that Richard come out of the closet and admit he is a beta bitch for black bull cock. Those women do not need to waste their time with a poser. I love being Richard’s phone sex therapist. Is he a cool guy? Yes. But he is such a pathetic little BBC loving pansy too. If he just came out of the closet, he could be a black cock faggot 24/7.

phone sex therapist

Sophisticated Sexy Dominatrix in Control

sexy dominatrix

You might think that a sexy dominatrix has to have whips, chains, and be dressed in leather. That’s all good and well if it’s what your Mistress is into but let me just tell you right now that it doesn’t always have to be like that. I can put you in your place over the phone with just my voice. I will command your obedience as soon as you hear my voice for the first time and there will be no going back after that. You will be addicted to me. You are probably already feeling addicted even at the thought of me.

Depending on the day and my mood, you could be up for all kinds of domination. Humiliation is one of my favorites, especially when you have a little dickie that I get to make fun of. Do you like being led around on a leash? That’s something that happens to my subs from time to time. Also, I’m big on cock and ball torture, so if you get out of line, just know that there is severe punishment on the line. Are you brave enough to fall under my spell and commands? I guess we will find out.

Richard Sheets BBC Faggot

Best phone sex

The best phone sex is outing a BBC pantyhose wearing fuck whore. Richard sheets is that fuck whore. A dirty little slut who wears pantyhose and loves big black cock. Richard is such a little faggot whore who loves to get fucked retarded by big daddy dick. Look at the little faggot.

These big black cocks that fuck my sissy faggot keep the fuck out of his little pussy. The best part is big black daddy gets off on hurting little white sissy faggot. Richard is a stocking loving sissy faggot for big fucking black cocks. The only use I have for this little faggot is to humiliate him.

Richard moans like a little Beta bitch when that big black cock fucks his little faggot hoe hole. My little cocksucker admitted that he likes to beg for that cock. In fact he lets his big black daddies fuck him bareback what a pathetic little slut huh?

Cocksucking phone sex

Gwens Forced crossdressing

forced crossdressing One of my specialties is forced crossdressing. And this time of year is amazing for men who need to be dolled up and slutted out. Now look at this picture, one of these isn’t like the other. One of these sexy vixens is a shemale sissy, with a tiny dick. Can you pick me out here posing with a few friends after we took turns making our sissy slave whore into a beautiful slutty fuck doll! I have so many ideas on how to make you the perfect princess with a penis! Stockings, short little sexy Christmas dresses, silver cock cages with bells hanging from your balls. As you learn how to walk with a swish to that ass and balance in heels over six inches. Shaved, lotioned, and prim all sexy and feminine. But as you look at the part there is more sissy maid training that must happen. Just like our little sissy ladyboy, we had to teach her to clean out pussy, to take a dildo up her sissy pussy and submit to not only women, but a nice big fat juicy cock one day soon. It’s up to sexy sluts like me to make the perfect princess despite having a cute little penis! Perhaps you in your little slutty Christmas outfit can cum see me and submit the was a sissy la-la should! There is much sissy fun to be had with this Mature Domme Momma!

Daddy’s Favorite Trophy!

Sexy Legs

I’m a lucky little slut around this time of year, Daddy sure does love to spoil me and share my sweet little pussy! Every year daddy takes me with him to a very important Christmas gala with his business partners, I dress up in my finest gown and feel like a princess when he shows me off all night. On his arm I know all the men at the party are hoping daddy will be generous enough to share me with them. Last year we rented the whole penthouse suite for the after party, I wore a cute little red lingerie set while daddy was bearded like Santa. All the men who came were so excited for their turn to fuck my tight little twat, I took so many shots of cum down my throat and in my holes that daddy was very proud of me. He bought me a beautiful diamond necklace for Christmas to wear to next year’s gathering!

Sissy Dominatrix Fun!

Erotic Roleplaying

I’m a slutty little dominatrix who is always looking for a sissy to humiliate and use! My favorite thing in the world is feeling completely superior to real sissy sluts who need a good fucking in the ass! I get my sexy companion Andre to fuck their asses and humiliate them all while I watch and enjoy. I like nothing more than seeing a supposedly straight man bend over and spread his cheeks for my Andre’s cock. If you are a secret sissy who needs to be dominated, I have just the plan to make you take his big beautiful black dick like the true sissy you are! I know once Andre makes you suck his cock and starts pounding your sissy pussy, you will be begging for more!

Soft Sissy humiliation

sissy humiliationIt doesn’t always have to be outright sissy humiliation. It could be me reminding you that today you got out of bed still a dull, small dicked man. That desire is always with you, beating like a drum in your head. You pull yourself out of bed and your wife is already peeing and you sigh and grumble as you walk away. “Just pee in the shower?” she calls after you. Fuck you would make a classier woman than this uncouth cunt! As you make your way back to the bedroom you notice she has laid out granny panties, aagin. SHe never wears the pretty thing you buy her. “They are uncomfortable,and tight.”  If she went to the gym you pay for she could fix that problem. And maybe find a nice cock to ride, she would be less of a cold hearted cunt if she was getting fucked proper! 

This is your life as you watch her shower hastily over the Gifts God has blessed her with. You would worship your female form if you were born with everything she has. How it would feel to wash your body, your tits and not have a stub of a reminder you were born male. You would shave, moisturize and worship your form.  Just to be emasculated and feminized, and  never have to live like a man again! I know you longingly think of the nylons, skirt, and pumps you want to wear! There is a world where you can let go even for a few minutes. Erotic roleplaying takes a new form with a “man” like you and me helping you!

Sissy Maid stories to live by

sissy maid stories The bubbles lapped my skin as the water swooshed back and forth. I had been reading some new sissy maid stories and was lost in the thought of my newest sissy. My body was alive at the thought of my sissy Sucking the UPS driver’s cock as a tip. We had been making good progress, and the outfits He bought to dress up in had become more sissified every weekend. He had taken my strap once and had taken three weeks to come back and see me. I was sure that would be the last session we had. But this morning I received a sissy novel on my doorstep and A bottle of wine and a Bath set. We had a “date” soon, and I was crafting a plan to keep him in my care for a long time.
I had fired my part time housekeeper and the house looked like a single busy business woman, lived alone. I stepped over discarded hose and panties, over towels and lotion bottles; giggling to myself. I had added to the mess with Hiding sissies butt plug under a pile of jackets and leaving a note beside it. Sissy was going to clean my house and sissy was going to either Present herself fully, or find another Mistress, My boots and black leather outfit With the crotch cut out would set the scene. It was Sissie’s favorite outfit. A leather loving sissy who would orgasm if he was allowed to click my boots too long.
The note read: Things you need, Your butt plug. (lube or no lube) The shopping bag in the closet behind My favorite Boots and Paddles.
If you wish to submit fully to me, and give me control to lead you into true sissydom, You know what to do. If you wish to end your contract you may gather your things and walk out the back door to hide your shame, No refunds on my Mistress tributes.

It took him 15 minutes. I waited dressed with my legs propped up on the couch. Sissy came crawling with her ass in the air, one pair of panties on and a pink leather paddle in his mouth. Sissy whined at my feet like a good puppy sissy.

We would begin his sissy maid training fresh. I had new ideas from his book.

Sissy Play In Autumn

Phone Humiliation

When the weather starts to get cold my stud ‘Andre’ and I love bringing a reluctant sissy home to get completely cock ruined by us! I start out by lighting a fire and pouring some delicious red wine from my sugar daddy’s cellar. I put on my fur coat all naked underneath while Andre starts to stroke his cock while our sissy watches. Once I suck Andre hard I know our little sissy is dying to stretch their jaw out on him too… I command him to “Suck My Andre’s Big Black Cock!” if he knows what’s good for him he will crawl over and stretch his jaw wide until Andre’s cockhead is hitting the back of that wet sissy slut throat! I’m not satisfied until our sissy is getting throat fucked and gagging until his little clit sized cock is straining against his panties!