Category: Sissy humiliation training

Glory hole punishment

Taboo phone chat

One of my sissies needed a little lesson on obeying orders and listening to his mistress. He also needed to be punished and humiliated too. I had the perfect punishment for him! I took him to the nastiest and seediest sex club downtown dressed in fully sissy panties, makeup, and heels. He had to walk through the parking lot and the front of the club in nothing but panties, makeup, and 4″ slut heels. I lead him through the club to the grimy dirty bathroom stall and made him get down on his knees on the filth covered floor and wait by a hole in the disgusting wall for a big cock to poke through. A really dirty looking uncut cock slid through the hole and my little sissy started to gag when his face got near it. I gave him a sharp smack across his ass and told him if he didn’t start sucking, I’d put his ass up against the hole and let them fuck him. He hesitantly obeyed and sucked the nasty dick like a good little sissy bitch and even swallowed when his mouth was filled with cum. That was just the first dick too, I had him on his knees for hours sucking any dick that came along, no matter how filthy or dirty they were. This is what happens when sissies don’t obey their mistress. They need to be taught a lesson and punished. You have to remind them who’s in charge. I love humiliating a sissy and most of the time they love it too, even if they don’t want to admit that they love sucking big black cocks, but even sissies have their limits and don’t want to suck nasty dirty cocks from a filthy glory hole bathroom for hours. He should have thought of that before disobeying me though.

Become Your True Self w/ Femboy Training

He was so confused and really needed my Femboy training sessions. It was something Jamie was really uneasy about and felt he needed to hide it, but the urges and desires to be the Ladyboi he truly was could no longer be denied. He contacted me and after our first session was already feeling more accepted and excited about his ability to come out about his Sissy needs. He would hole himself up in a Hotel room outside of his town and bring he secret suitcase of all his pretty Sissy clothes, toys and accessories to be himself finally. He lied and said he was going out of town for work. He was really going out of town to be the sissy faggot he really wanted to be and wanted the nerve to really suck cock and hook up with a sexy tranny hooker. He always failed to get the nerve and just spent his time being a sissy online in the crossdresser kink sites where he would talk with others and share pictures. When he found me, he was finally able to gain the assurance and my training and strap-on play really brought the inner Sissy faggot out. If this sounds remotely like you, I would love to assist, I am always open to first timers and experienced Sissy’s alike. The humiliation and forced cocksucking is very exciting for me and I love making you my sissy submissive.

Femboy training

Sissy phone sex with the best

sissy phone sexSissy phone sex with the best bitches on the block, that is what you will find here, so when little bitchy faggots call me with an attitude I need to slap them right down to size. This little whore thought she could talk shit to me, as if I would bow down to a sissy can you believe that shit? I am a Goddess I bow to no one least of all some little sissy dick sucker! She needed to be taken down a peg so I called several of my friends over and we used that sissy slut until she learned that her place was at our feet. Sissy had to dress up and then get on her knees and suck all the dicks there. That included big black cocks, smaller white cocks and huge rubber strap on cocks that we were wearing. We really opened up that little whore’s pussy too, I bet that bitch won’t be sitting down for a week after last night! By the time we were thru with her she was begging us to stop and she promised to be a good girl in the future. We shall see tho, I think sissy enjoyed her punishment and will be back for more real soon!

Pussy Paradise

Sissy pantiesMy sugar daddy will spoil me to the end of the world. I had a blast in bora bora. Everything I wanted I got. I could see all the other sugar babies prancing around. It was pussy paradise to all the rich sugar daddies. My loving slave pet came along, and I had him dressed up. I had a sissy bikini for him and even plenty of sissy panties. I could see his eyes full of lust and wanting to be me. Well, slave pet you will have to enjoy being in my shadows and embarking in every journey I am in and being my dandy hand servant. I wanted to treat my pet with a sweet bukkake bash. I gathered around some of the locals. I had a few connects and I made it possible to get all the tour guides and their friends to cum blast, my sissy. I could see it was heaven for him. 

Mistress Phone Sex For Pansy Princesses

Your a pathetic excuse for a male as your just a Pansy Princess in need of Mistress phone sex, and I am just what your sweet ass needs. I don’t care if your ass is pink, red, brown or blue it is mine to own and I will have full ownership of you, slave. I’m the one to bring the pansy panty wearing princess faggot out that has been kept in the closet for too long. I want you to shop for pretty panties and make sure the clerk knows they are for you. You will ask her if they are your color or if she thinks the style is good for you. I will want you to wear pretty silkt panties under your man suit and go about the daily grind of being a useless male, only knowing secretly how much of a sissy you crave to be. I want to help you my pansy princess.

Mistress phone sex

He was such a little whiny bitch

sissy phone sexGod, if there is one thing I can’t stand it’s a whiny little bitch and this faggot was the whiniest little whore I had ever met! All he did was complain, he wanted to be taken seriously as a “man” but he was barely 5’4″ and skinny as fuck, he looked like a weak ass bitch and no one would ever take a man like that seriously. He wanted to fuck me of course but he was not manly enough for a woman like me so I forced him into some of my clothes instead. He looked like his true self in my clothes, that slender little body was made for dresses and as much as he didn’t want to admit it, he looked better as a bitch. I invited some guys over and you know what? They liked that little bitch boy, they had him on his knees sucking dick for hours! He tried to say he didn’t like it but he squirted all in his panties so I know he did.

Best Sissy Trainer Coraline

best sissy trainerI am a sissy trainer. The best sissy trainer. I love being one too. I can look at you and see your true essence. I have this neighborhood boy who thinks he has a girlfriend. He thinks he is masculine and just like other boys. He needed some sissy therapy. He needed me. I had him come over for a friendly talk. I planned on feminizing him, but I needed him to first acknowledge that he is not like the other boys at school. First, I had to explain to him that him and his girlfriend weren’t dating. I was 100% sure she thinks of him as a gay best friend or something, but not a lover. Their “dates” include shopping at the mall and getting a drink at Starbucks. He is always home by like 7 or 8pm from a “date.” And, the kicker, they have not even French kissed let alone fuck. I had him strip down naked so I could see his cock. He didn’t have one, which was no surprise to me. He had a clit stick. I put him in some panties while I gave him some sissy hypno training. I mixed images to show him that what is hanging between his legs was nothing like what was dangling between the legs of the high school jocks in the locker room. I also got him to realize that his schoolgirl friend is fucking other men and that he is permanently in the friend zone. It can be a tough wake up call, but not all boys are created equal. Some have small dicks. Some have feminine bodies. Some are never liked sexually by girls. Some are meant to get fucked not fuck. My neighbor boy is one of those boys. We have a lot more sissy training to do, but I got him to the first step which is realizing he will never be the romantic lead in any girl’s life.

Mistress Phone Sex For Pathetic Sissy Sluts

I am really loving all my new sissy sluts calling me for Mistress phone sex. It’s amazing to know so many naughty little perverts ready to submit to their inner feminine and worship the real femme as they seek guidance and approval. Your desires to serve me invigorate me like a vampire feels after feeding on a beautiful dane’s neck. The power I feel in feminizing your masculinity into a blithering fool for cock is undeniably wonderful. It helps that I have a couple sissy trained ladyboys in my brood also. The idea of forcing you into sucking off the black security guard that stands at the door of the club is even more intoxicating than a bottle of fine red wine. I want you to just relax and completely submit to your inner woman and go with those cravings for cock.

Mistress Phone Sex

My Sissy Slave Whore

Domination phone sex

I have the most perfect sissy slave whores ever, I make sure that I train them extremely well. My personal panty boy slaves are leashed around their pathetically limp dickies while I give them orders. First, Mistress’ patent leather boots need to be licked clean. I better be able to see my own pretty reflection in those big boots and if they are a good little sissy, I will step on them with my pointy heel while they scrub the bath tubs clean. I keep my sissies in line by making them stay naked while they please their Mistress and do their chores. They can earn their frilly sissy whore outfits piece by piece. Everything from their sweet ruffled panties, nylons and bras must be earned by pleasuring Mistress’ clients and cleaning up after their Mistress. After all, it is important to train sissy slaves on how to be obedient little skanks. If they misbehave, harsh punishments will be dealt out on their sissy dicklets!

Get me prepped and clean me up

Phone dominationNothing gets me hornier than having total phone domination over my slutty sissies. Their job is to get me prepped and ready to take big fat cock deep inside of my perfect little pussy. The wetter I am the better! My sissies know that I only fuck massive dicks so they really have to put their tongues to work while getting me nice & juicy for the delicious boners that await me. Before I have sex and after too, I make them slave away on my beautiful body! When i’m nice and filled up with cum is when they really get to enjoy themselves. It’s such an honor for me to designate my sissies as my cum lickers. If they’re special enough to be able to get between my sexy legs and clean me up then they know to really consider themselves lucky! I’m a very picky sissy trainer and I only select those who I feel are truly deserving. My standards are super high and it’s a fucking privilege to even be in my presence let alone to physically touch on my goddess frame. Load after load of delicious cum piles up inside of my princess pussy, the perfect treat for a sissy of my choice! Will it be you?! Maybe if you’re blessed enough!