This is my special treat for your sissy ass

Sexy mistress in a video by SissyInstruction

share gif:

 
Bailey Paige has a special treat in store for you and it's really fucking long. This feisty bitch plans to train you to take her 12-inch dildo all the way to the balls.
 
I know that you don't like the idea of this big dick being stuffed into both of your holes, but the reality is that you don't get a say in what happens. As your dominatrix, it is my duty to make sure that you're educated and prepared for anything. I figure that one day I'll get a dude to fuck you, so the sooner you learn to be a sissy, the better!
 
Everyone knows that a good slut can take a dick without a problem. The issue here is that I don't think your ass or mouth are ready for that kind of punishment. Thankfully, after a few sessions with me, we'll make sure your holes are as prepared as possible for any dude that wants to come along and treat you as a hot sissy slave.
 
- Bailey Paige
 

We are going to do whatever it takes to get you some cock

Jasmine Mendez Anal Sissy Training Brunette Porn Video POV Instruction

share gif:

 
Jasmine Mendez is not the type of mistress that you want to let down. She means serious business and is going to do whatever it takes to make a woman out of you.
 
Look, I think we need to have a little talk about the way you've been acting lately. All of this obsession with women - from my point of view - is less to do with an attraction to them and more to do with an envy toward them. Look, there's nothing wrong with wanting to be a sissy. We are going to make sure that you know what it's like though, so let's get started.
 
First of all, how about we get that ass if yours into some nice female clothing? I want to see you dressed up like a hot little slut. Then, we're going to try and find you a nice hunk of a man to come on in and fuck the hell out of that hot little asshole for you. Nothing will make you a sissy quite like getting pumped in the rear by a big fat dick.
 
- Jasmine Mendez
 

Nikki Daniels makes sure her slave looks great for a night out

Femdom video with Nikki Daniels

share gif:

 
Nikki Daniels loves dolling up her friend who cannot wait to go out to a club and get himself a massive dick to suck on. Fortunately, the brilliant brunette mistress has all sorts of beauty products to turn this guy into a cute babe.
 
We are going out to the club tonight! I knew you were going to be excited but I cant let you wheat that, no. I have to get you ready. I picked out these nice black panties for you so you have to wear them. I also got you a matching bra. It looks so good on you. You think that you are going to have a good time tonight, don't you? I know that you like to suck cock when you want to have a great time.
 
If you want to get a man, I will have to put on some makeup on you. I need you to look your best since we are going to a very nice club and we will find some hot stallions to ravish your mouth with their boners. I need to put on some lipstick on those cock craving lips as well. Actually, let's exchange that lingerie for something more feminine. Purple is your color!
 
- Nikki Daniels
 

Samantha Grace dresses up her slave as a hot slut

Sissy insruction presents: Samantha Grace

share gif:

 
Samantha Grace needs to punish her slave for not obeying her rules so she made a few changes in his daily routine. She will dress him up in some girly clothes just so he can be more attractive to his future fucking buddies.
 
I can see the cum stains on your panties. What did I tell you about that? Now, I have a new punishment. Obviously, you cannot be trusted with panties because you are going to cum-stain them so I think I am going to have to put you in a pair of yoga pants, like mine. You will have to wear these pants so you don't get any jizz on your panties. Would you feel nice in a tight pair of pants? In addition to this, I will put you in a nice bra as well.
 
The other aspect of your punishment for being a dirty boy will be a nightly ass pounding. You are going to be fucked up your butt every night by a different person. I will turn you into a slutty girl who is going to be drilled by horny men. It is time for you to get ready because we are starting tonight.
 
- Samantha Grace
 

I can teach you how to take dick you sissy

Kendra Sissy Instruction Hardcore Porn Video Tube Brunette Sissy Training

share gif:

 
Kendra here is going to teach you a thing or two about being feminine and taking dick. She's a pretty hot tranny that gets fucked in the ass daily by big, hung studs.
 
I'm so glad that you're looking to come on this journey with me. I have to tell you now that as a transsexual, I love nothing more than being as girly as possible for my lover. It's usually big muscly men that get to play with me. I love how it feels to have my asshole fucked by their massive dicks. You've never felt anything until it's a big cock in your tight feminine asshole.
 
Do you like the idea of being a sissy bitch and taking it in the ass? I think with a little work you could pull off being a woman and find a man that was more than willing to hump and dump you. You strike me as the type of sissy that would accept any cock no matter who it came from. You are one dirty feminine slut - I can't wait to hear about your first dicking!
 
- Kendra
 

Prepare your sissy mouth for a huge cock

A video of a blonde mistress wearing glasses: Vicky Vixxx

share gif:

 
Vicky Vixxx wants to give you a lesson in sucking cock. Prepare your mouth, because this huge dildo is going to destroy your gob until you learn to take it like a bitch.
 
While you'd like to think that this knowledge would never be useful, the simple fact is that I imagine your mouth is going to get a lot of punishment sooner or later from a hung stud that wants to use you as a sissy bitch. Oh stop pretending, bitch boy. You'd love nothing more than to get fucked by a dude while you pretended to be a girl.
 
Of course, the best thing we can do for your sissy slut training is to get you used to this huge dildo. Big dicks is what this is all about, so how about you give up that mouth of yours so we can start. Just know that when I'm finished with you, your mouth will be more than prepared for a cock of any size that wants to violate your stupid gob.
 
- Vicky Vixxx
 

I’m going to sissify your bitch ass for my amusement

Sissyinstructions presents: JadeI ndica

share gif:

 
Jade Indica has put a lot of thought into her sissy boy's outfit for the big date. But since the fellow does not understand the severity of the situation while the hot brunette is instructing him she will need to use a chastity device to control the man's urges.
 
I have been waiting for you. It is not nice to be late. If you want to be a real chick, you need to be punctual. Now it is time for you to put your girl clothes on. Your date is going to be here soon so we have some time to prepare you for what is going to happen tonight.
 
Are you ready to put on these pink dresses? We need to choose the best one for you. I am going to choose the cutes outfit for you since I want you to be the prettiest lady. Look at that cock, it is getting hard. This is really turning you on. I like the fact that you are getting horny while trying on women's clothes. I might have to throw you chastity just to control you since I don't want any precum stains on these gorgeous outfits. I know you are excited to get into my attire and to smell like me.
 
- Jade Indica
 




All the network sites you'll get access to

sissy instruction fem training crossdressing

Your sissy transformation is coming along well. You are just so cute! Before you know it, that ass of yours is going to be out on the streets and looking for some hot cock to fuck

femdom sissification feminization trainer video network

You're such a fucking pitiful loser. It should be so obvious that a woman as good as this can do a hell of a lot better than a pathetic maggot like you. You are only useful as my slave!

bisexual training videos femdom pov

You're my bisexual slave, and so long as you're still doing exactly what I tell you, I'm more than happy for that ass of yours to be fucked nice and hard. I bet that feels absolutely incredible.

permanent chastity humiliation femdom pov

You know what I should do? I should just lock you up in the biggest strongest chastity device I can find and throw away the key. Permanent chastity forever... How does that sound?

strapon pegging hardcore porn

We are going to put your loyalty to your mistresses to the test. You see these two big strapon dildos? We are going to double team your ass and mouth for hours on end!

cei cum eating instruction femdom videos

Give yourself a gentle tug to begin with. When you're done with blowing your load, you're going to take that condom and eat all of the jizz out of it like a good little cum eater.

cuckolding humiliation femdom instruction

I'm going to have a big cock come over here and fuck me. You'll sit in the corner like a little naughty cuckold and watch it happen too. I will let you clean up afterwards if you are lucky!

black cock worshiping cuckold femdom

You need to be taught about worshipping big black cock, because one day your mouth and ass is going to be met by one BBC that is destined to pound the absolute shit out of you.

first time gay fantasy femdom pov

Look, I don't care what excuse you come up with - you've been chatting up men on the Internet and I love the fact that you're hungry for cock, I just wish you told me sooner.