1,510 results for sissy training

Sissy Phone Sex w/ Coraline and me!

sissy phone sex We are going to have so much fun on this sissy phone sex call. Let me go get my makeup and that sexy little outfit I was talking about. You have never done this before, have you? Don’t be shy now baby! I know exactly how to bring out your sissy side! Now put on these little see-through black crotchless panties with these stockings. Aww, shame you, poor little sissy. These little panties will cover up that tiny dick so that no one will laugh at you. Well who could that be at the door now? Sexy Momma Coraline here to help me turn you out! I know you secretly want each of these hot women to put on that strap-on and fuck you in your tight little ass, you little sissy boy. Oh, is this turning you on? I can see you perfect little clit stick dancing! Coraline laughs and tells me to get the lube, she wants first dibs on that tight back door pussy! Our strap-on silicone dick is better than yours will ever be, sweet panty boy Slut! ! Now pull down those panties bitch boy, and use my vibrator on your little dicky while Coraline fucks you in your tight ass pussy. Now give me your spurties in my mouth! I stand up as soon as you deposit a teaspoon of cummies in my mouth. You wonder why Coraline is snickering behind you as she pulls out her “dick”. I got to kiss you and cum swap and you feel Coraline push you down and shove the strap in your mouth. “Clean Your ass juice off of my expensive strap , bitch!” Mistress Coraline Barks. Oh, such a good boy doing what you’re told to do. And we have only begun your sissy training audio!

sissy training audio

Party Girl training

 

 

online sissy trainingI’m a party girl that attracts all the guys. I love to use my tiny body to my advantage. My perfect night out includes me going to a nice club and getting wild. I love to dance and be the center of attention. It is the Leo in me. I am all about being the star of the show. I enjoy guys wanting to fuck me and trying to buy me drinks left and right. So you want to be my sissy and indeed of some online sissy training? Well, you will have to be a good little listener and follow all the rules. It’s an honor to follow me and learn some tips and tricks to further your adventure in sissy life. You don’t want to be an average sissy. You want to learn from the best and have to emulate as much as possible a perfect princess like me. Although you will never be Mistress Ember, you can be a fan.

Earn Your Sissy Panties

A good sissy is a sissy that is trained well. Well trained sissy girls earn their status. They earn the opportunity to wear sissy panties. Of course you can always wear any panties you wish. But the roles of some sissy girls is them doing good to earn their special girly tokens.
My sissy in training recently earned her pretty girly panties. The very ones this sissy fantasied about earning. She earned them by being a good little cunt licker. She licked the creampies of twenty hung guys from my pussy. This was how she earned her panties. In fact not only was it the panties, it’s about what cums with the panties. That’s right, 20 loads of cum ejaculating in her panties as she puts them on and wriggles around at the glory hole.

She earned her panties and all the cum loads of a line of horny men. Horny hairy cocks and balls unloading against sissy jens asshole. Her pretty sissy boy pussy was not penetrated it was just coated with the jizz loads to fill her panties up.

Sissy panties

Earning Your Sissy Panties

I had just come back from shopping with my bestie when I caught him!

My latest sissy trainee was sneaking through my panty drawer and trying on all my silky sissy panties!

He was standing there in my best pair of lacy pink thongs, sticking his tits and ass out like a prissy little fag!

Sissy TrainingI tried not to laugh as I burst in, catching him grabbing for my matching bra!

I told him that those are my best sissy panties and they have to be earned!

I called in my friend and asked him to pull down his jeans, exposing his massive big black cock!

I told the little bitch that he could have any pair he wanted if he could suck this giant dark meat!

So he got down on his knees and held the hard cock with his thumb and index fingers as he barely licked the tip!

Clearly he had never sucked a cock before!

So I decided to give him a quick lesson, showing him how you hold the giant thick cock, wrapping your hands firmly around it, stroking it slowly and gently as you lick every yummy inch!

Then I showed him how to open real wide and push it really far down his throat as you swirl your tongue all around and suck that thick hard cock with every muscle you have!

The best part was seeing the look on the little panty thief’s face when that giant meat exploded in my mouth!

There was more than enough yummy cum to share so I swapped some with the sissy bitch as I kissed his pretty fag lips!

Now that he has tasted the cum from a big black cock, he can’t get enough!

 

 

Best Sissy Trainer For Dress Up

best sissy trainer

I take a lot of pride in being told that I’m the best sissy trainer someone has ever had. I truly love transforming sissies into their true form, so when someone appreciates the work I do, it makes me happy. I love to pay attention to detail and I think that makes them feel like I really care – and I do! When a sissy learns to do her own makeup or dress herself in an outfit that matches without my help, I feel like a proud mother. And when a sissy finally is able to walk in a pair of stilettos without wobbling and falling down, that’s like one of the best things ever.

It takes a lot of perseverance to become a perfect feminized slut but if you stick with me, I will take you all the way there. You won’t look like a man dressed as a woman. You’ll totally be able to fool people. I can’t wait for you to see how beautiful you can look with just a little bit of sissy training from me. So when you’re ready to get started with the feminization process, pick up the phone and give me a call. You won’t be sorry.

 

The Sissy Olympics

Sissy Training

I love my little troublemakers; they surely help me fund my high society events. I hold the Sissy Olympics every single year, and this year I’m hopeful to see one of my own personal fuck slaves win a Gold medal in the Cum Guzzling Competition. All the renown Sissy Trainers travel from far and wide to force their feminized little fuck boys to participate in my sexy fantasy games. One might wonder what winning a Gold does for the slave; the answer? He gets one night tucked up in my bed.

Yes, that’s right. I’ll allow whatever small cocked little loser that wins the Gum Guzzling Competition to play with my pretty pussy for a whole night. I know how badly you sluts want to truly be able to pleasure me. These other trainers might allow their boys to touch them, but my whores only get that royal privilege when they’re slurping sticky cum loads from my cunt. I suggest you start practicing now if you’re thinking of trying out for the team. My sissy girls Penny, Rosie, and Ginny are sure to cum in first.
I will be, in the meantime, being worshiped by sexy BBC Alpha Bulls. Extra cum for you sluts later!

Think you can beat my own little toys? Give it a shot, you beta bitch, small balled, cuck worthy loser. See if you’re worthy of Queen Presley’s cunt.

Sissy Humiliation Training

BBC Sissy Trainer

bbc sissy trainerI am a bbc sissy trainer. If you want the bbc sissy experience, be prepared to drink a lot of protein. Black spunk is full of good protein that helps you develop a good sissy body. I make the best cum shakes too. Oliver is my newest sissy on the block. I call her Olive now. She found me through another a sissy I train. Like many of my callers, she has a fascination for those big black dicks. She watches hours of black cock porn films, including interracial cuckolding videos. I have a big bull pen of black cock studs who love to make white men black cock faggots. Trevor is a black bull who has been fucking me for years. He has no problem making white men submit to his 11.5 beer bottle thick dick either. He is a strong man. A former body builder turned personal trainer, he is a massive man who can get men and women to do anything he wants. He is not gay. He is not even bisexual. He is just a dominant black man who loves a posse of bitches and sissies worshiping his black stallion cock. Olive has only been sucking on black dildos. She has not been able to suck the real thing yet. I do not do excuses because it you want something badly enough, you will find a way to make it happen, right? Well, no more excuses for Olive. Trevor skull fucked her giving her a taste for black cock spunk. Before Olive had arrived for sissy training, Trevor had filled me up with his nutter butter. I do what all good sissy trainers do to, I pissed out the cum and made a smoothie for my sissy. Olive drank down her nutter butter smoothie while she got her anal cherry popped. Are you ready to be my BBC sissy faggot?

sissy training

Be My Sissy Slave?

 

online sissy training

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!

Sissy slut Train

Playing with my pussy thinking about the time I ran a train on my sissy slut boy. I made him come over with his school girl outfit on, as soon as he got through the door, I made him crawl on his knees to the waiting big black hard cock I had for him. He is a good little slut so he did as he was told, opened his mouth and went right to work, licking and sucking a big black cock and playing with his balls while he did that I came from behind and I stuck my big strap dick in his ass hard and fast. The harder I fucked him I pushed his mouth harder on the big dick making him gag like a little fuck slut he is. Then we switch and he got a big black cock in his ass which made him moan like a little bitch slut, he was getting used so well he came all over the floor and with that my playmate filled his ass with hot cum, I made him lick up his mess and reminded him he belongs to me. 

Sissy girl training

I Love Sissy Phone Sex Callers

sissy phone sexI love sissy phone sex calls. Sissies are the best. Every woman should be so lucky to have a sissy in her life. I have many. I have phone sissies. I have real-life sissies. And I have 2 sissy sons. My sissy sons will be shemales one day. And they will have my full support too. I can make any sissy pretty. I can turn any sissy into a shemale too. I love feminizing sissies. How can you be a sissy in man clothes, right? It is just not a look that goes well together. The first thing I do with all sissies, including my sissy boys, is put them in panties. I will not say that all sissies have small dicks, but most too. I think the lack of testosterone makes dicks smaller and lends folks to be sissies. I have met a few sissies with big dicks, but they were just sort of occasional sissies. Either they just needed something taboo to push them over the edge or they were partying. Most sissies, however, have clits. Tiny little things that no woman would want or could feel. I like to make fun of small willies as I put them in appropriate under garments. Once I have panties on a sissy, I need to find matching items like a bra and garter belt. I also enjoy a dress too. Femboy training means learning to dress like a sissy, act like a sissy and living life like a sissy. Once a sissy looks the part, she can act the part. I train all sissies how to suck cock. There are a few sissies who do not suck cock, but they are few and far between. Once you feel and look girly, you want to do girly things like suck cock. I am great at training sissies to swallow cock. My little future shemales are great cock suckers.  Sissies are like dolls to me that I can dress up and play with. Think you are ready to play?