Tonight you get to be a real sissy girl
08:17
I found panties in your drawer and I want to know who they belong to. Shut up and take your pants off. Oh my God! Why the fuck do you have panties on? You are a fucking pervert. - jerkoffencouragement
I will doll you up like a proper sissy girl
07:01
I am so excited we are going to do this! I know it was a bit difficult for you to agree to this kinky game but I am so glad you finally did. - Alura Jenson Bossy Delilah Carissa Montgomery Gina Bang Jewell Marceau Whitney Morgan - sissytrainervids
I will doll you up like a little sissy slut
08:07
You envy girls and their pretty little outfits that they get to wear. You would just love to be able to do your hair like we do or wear a sweet scented perfume. - Amai Liu Bossy Delilah Jade Indica Jewell Marceau Nikki Brooks Nikki Daniels Samantha Grace Whitney Morgan Natalie Laine - sissytrainervids
I have a matching bra and panty set for you
06:21
I have a cute little sissy outfit I want you to wear. I think once you put this one, you will look like a real sissy girl. - Alexis Grace Samantha Grace Hannah Perez - femdomvideos
I will help you transform into the prettiest sissy girl ever
07:42
I'm going to clean you up and make you into a nice girl. I'll put lots of make-up onto that little face of yours! Aww you'll feel like such a girl then I'll put some eye-liner on you and even more m - Allura Skye Amai Liu Carmen Valentina Danica Logan Sadie Holmes Goddess Rapture - femdomvideos
I will prepare your sissy ass for a night on the town
08:16
You should be yourself around me and besides, just because you have a cock doesn't mean you cannot look pretty. Be a good little boy and let me dress you up. - Bossy Delilah Nikki Brooks Nikki Daniels Whitney Morgan Penny Barber Kandii Kiss Natalie Laine - sissytrainervids
Deep down you are totally just a sissy slut
09:17
You don't have to hide your sissy side when you are around me. I want to help you explore this feminine side of yourself. I even set out some clothes I think you will look good in. - Angel Blade Cheyenne Jewel Whitney Morgan Taylor Raz Hannah Perez - femdomvideos
I will dress you up like a total sissy slut
07:05
Today we are going to dress you up like a proper girl. But we are going to start with the basics. Show me your legs. They better be smooth like silk if you want to be a lady. - Carissa Montgomery Jade Indica Nikki Delano Samantha Grace Soraya Rico - sissytrainervids
Tonight I make you into a sissy girl
08:29
I found panties in your drawer and I want to know who they belong to. Shut up and take your pants off. Oh my God! Why the fuck do you have panties on? You are a fucking pervert. - Addie Juniper Savannah Fox - jerkoffencouragement
Sissy Maids Self Bondage Armbinder
28:25
armbinder fastened with icecubes in socks and D ring connected to chastity device.. every movement tugs at chastity and wiggles dildo around... - Derek6699
I have a big black cock for your tight sissy ass
07:46
Come here and get on your knees. You already know what is coming, don't you? I know you crave this big black dick between your lips. I will train you and get you ready for the real thing. - sissytrainervids
You are such a pretty little sissy girl
07:27
There's my sissy little girl bitch. Care to guess at what's going to happen this afternoon? I'm going to make you into my beautiful sister. See. I'm a gorgeous lady, and I think I need a partner. - Kneely Morgan - femdomvideos
You are going to be my new sissy boy sex slave
08:59
We really need to get rid of that beard - it doesn't suit a beautiful lady like you. Shave it off and start to put makeup on for me. - Kneely Morgan - femdomvideos
Sissy Maids Self Bondage 06-16-2020
29:21
Armbinder and ice cubes... gagged and blindfolded.. chastity belt locked on and stuffed with a large dildo... great afternoon - Derek6699
We are excited about our new sissy slave
06:55
We are going to dress you up like a pretty girl and we are so excited about that. Look what we got you! A nice bra with some glitter on it! - Jewell Marceau Lilith Lust Nikki Daniels Penny Barber - sissytrainervids
I will turn you into a little sissy girl
07:18
I'm so excited for our play date, because I'm going to have the chance to dress you up like a little girl. I know how much you love it when I feminize you, and today - well, you're going to get exactl - femdomvideos
You look so adorable as a sissy girl
06:11
Put this on right this second. I think you're going to look so adorable and the noise it makes is really pretty too. You don't have much of an option either, so there's no point protesting. - Astro Domina Cheyenne Jewel Gia Steel Samantha Grace Penny Barber - femdomvideos
I will take you out on the town dressed as a sissy
06:53
Now let me do your eyes. I am going to make you into one hot chick. Let's not forget to make those lips super red. I think that color looks great on you. It is good for sucking dicks. - Diana Knight Gia Steel Nikki Daniels Nikki Delano Kandii Kiss - sissytrainervids
You are nothing but a sissy femboy slut
07:50
Buckle up boy, because we're going to strip you of that manhood and subject you to the highest levels of female indulgence. Take a look at this beautiful dominatrix before you. - Kneely Morgan - femdomvideos
I will make you bi fantasy some true
07:05
I have heard that you have no idea how to be a good little sissy boy and take cocks. So, I will guide you through this. The first thing that you need to know is that you need to lube up this pulsating - Nikki Brooks Samantha Grace - femdomvideos
I will take you out in public dress as a sissy
07:56
I feel like being a bad girl. Would you like to join me? I am in a naughty mood today. We can do it together. I know you have been admiring my cute outfits. - Kneely Morgan - femdomvideos
You can play with my tits if you dress up like a sissy
08:48
I can't believe that you do that, but seeing as you want to be a girl, I can't help but wonder what it would be like to assist you. How about I make a deal? If you wear a nice gown for me, I'll show y - Kneely Morgan - femdomvideos
I require you to dress as a sissy all the time
07:12
Hey, there pretty little boy! Are you ready to be dressed up as a girl? I am going to take you out tonight with my friends and we are going to party. I just want you to doll up. - Kneely Morgan - femdomvideos
I command you to dress up like a sissy
07:36
Hey, there pretty little boy! Are you ready to be dressed up as a girl? I am going to take you out tonight with my friends and we are going to party. - Jewell Marceau Lilith Lust Nikki Daniels Nikki Delano Samantha Grace Penny Barber Kandii Kiss - sissytrainervids
Sissy Maid handcuff self bondage
38:34
hung the handcuff keys from ice lock on the ceiling chain.. nothing to do but be horny and wait - Derek6699
Are you ready to become my sissy bitch
06:32
Are you ready to be Princess Anna's little sissy bitch tonight? She is going to dress you up like a girl, put some lipstick on your and shave your legs. She loves humiliating all her pathetic slaves. - Kneely Morgan - sissytrainervids
I chose the perfect sissy outfit for you
07:48
Oh, do I have a treat for you today! You see my cute lingerie? I got you the same pair of panties and a bra so we would have the matching outfits when we go out tonight. - Carissa Montgomery Gina Bang Jewell Marceau Penny Barber Kandii Kiss - femdomvideos
I will help you pick out the perfect sissy outfit
07:36
Today I am going to teach you how to dress as a woman since clearly, makeup is not enough. By the end of this, you are going to be the prettiest princess. - Kandii Kiss - sissytrainervids
Another Sissy Maid Armbinder Self Bondage video
31:42
seems to be my favorite piece of BDSM gear... going to have to do another when my rubber gas mask comes in the mail. - Derek6699
We are going to break in our new sissy slave
06:55
We are going to dress you up like a pretty girl and we are so excited about that. Look what we got you! A nice bra with some glitter on it! - Amai Liu Jewell Marceau Lilith Lust Nikki Daniels Samantha Grace Penny Barber Kandii Kiss - sissytrainervids
I have a cute little sissy outfit for you to try on JOI
08:02
I've got a surprise for you. A cute little outfit that I know you are going to love. I've got a sexy little bra for you and some nice matching panties too. - jerkoffencouragement
You will be the prettiest sissy girl ever
05:58
With your body, I think we can make you look like a super sexy sissy girl. I have some panties and a sexy little dress that will fit you perfectly and show off your curves. - Ashley Edmonds Ashley Sinclair Penny Barber Taylor Raz Kandii Kiss - femdomvideos
Relax and just let me big black strapon cock in
14:20
Your asshole puts up some initial resistance to begin with, but as soon as I calm you down and convince you that you're a hungry sissy, that butt enjoys every second and opens wide for this big dildo. - sissytrainervids
I will train your sissy ass with these big dildos
06:19
You have some really fucked up addictions, and I'm not going to beat around the bush: I will not stand for it under my roof. If you think I'm going to let this rest, you're severely mistaken. - Ashley Edmonds Ashley Sinclair Jean Bardot Penny Barber Taylor Raz Kandii Kiss - femdomvideos
I will turn you into the perfect sissy girl
06:59
Hop on over! I've got this cute bra for you and once you get it on I can start to do your makeup and turn you into the perfect woman. Once that's done, I'm gonna take you out and reveal you to the wor - Alexis Grace Katie Cummings Whitney Morgan Taylor Raz Kandii Kiss Hannah Perez - femdomvideos
I brought some sissy clothes for you to try on
07:06
Anyway, I thought you might want to try some of these, so get rid of your clothes and try on this outfit. These panties will look so cute with your tiny cock hidden away inside them. - Jade Indica - femdomvideos
I am so excited to play with my favorite sissy slave
07:28
I am so excited we are going to do this! I know it was a bit difficult for you to agree to this kinky game but I am so glad you finally did. - Jewell Marceau Nikki Brooks Whitney Morgan - sissytrainervids
I always knew you were hiding a sissy side
06:49
I fucking know it all along. You are secretly a total sissy girl deep down inside. Don't even try to deny all that sissy porn I found all over your computer. - Samantha Grace Whitney Morgan Penny Barber Taylor Raz Kandii Kiss Hannah Perez - femdomvideos
Collared Sissy Cuck with Small Penis Cleans-up Hotwife Pussy
00:55
Genuine UK amateur cuckold couple from Leeds cuckolding, hotwife lists on collared submissive cuckolds face making him lick her pussy clean while she humiliates strokes his small penis. - UKCuckolding
I am going to make your bisexual dreams come true
06:51
I have heard that you have no idea how to be a good little sissy boy and take cocks. So, I will guide you through this. The first thing that you need to know is that you need to lube up this pulsating - Nikki Brooks - femdomvideos
I will get you ready for a night out as a sissy
06:51
I am so excited for tonight since I got you a sexy little getup. It kind of looks like lingerie but you will wear it as a dress. First, you got your g-string to go right up your ass crack. - Kneely Morgan - sissytrainervids
I am going to make you wear sissy panties
08:23
Come on my little sissy boy, put these cute little panties on and squeeze yourself into this bra. I think that pink is your best color, and I'm looking so forward to seeing your hot little body. - Kneely Morgan - femdomvideos
Feminization Boudoir Podcast Interview with Miss Jenn Davis
08:03
feminization, sissy, spanking, humiliation, phone session, skype session, feminisation, sissification - MissJennDavis
Sissy Frilly Maid Stumbles Around Apartment in Ballhood
03:02
The Frilly Maid finds itself locked in a ballhood and bondage mitts and forced to stumble around an apartment! Watch as it’s totally helpless and an inflatable mess! - thefrillymaid
Sissy Maid Enema Bondage 2
18:37
cleaning up dirty maids ass for when Mistress gets home.. - Derek6699
I will make you into the perfect sissy slave
07:49
I have to say that I have noticed some tendencies in you. I know you don't want to admit it but I have seen them and I have decided to do you a favor. - Amai Liu Bossy Delilah Carissa Montgomery Jade Indica Jewell Marceau Nikki Brooks Whitney Morgan - femdomvideos
Mistress dildos and does CBT on sissy slut hubby
06:15
Sammi takes the Bad Dragon Knot, endures some loving CBT, and takes the dildos again...I love that blue toy! - Encntct
I will train you to be a total sissy slut
07:00
I've caught you going through my makeup, I've caught you going through my lingerie. Look, this needs to stop, and the only way I can come to terms with what's happening is if I turn you into a sissy. - Kneely Morgan - femdomvideos
You are going to be my pretty little sissy princess
07:30
I hope you’re excited for your outfit! I guess that look on your face just about sums it up. Come on, get out of that shorts and T-shirt combination. - Jade Indica Nikki Delano Samantha Grace Star Nine - sissytrainervids
I am going to make you my little sissy girl
08:27
I'm so excited for our play date, because I'm going to have the chance to dress you up like a little girl. I know how much you love it when I feminize you. - Kneely Morgan - femdomvideos
I will chain you up and tease your sissy ass so hard
07:16
I am not too happy with you since you have been pretty bad. Now I will have to punish you and your punishment will be to wear these neon orange panties. - Nikki Delano Samantha Grace - sissytrainervids
I am going to make you into the prettiest sissy ever
06:15
I want to watch you slip into these panties and laugh as your big butt just can’t quite fit. Then, I want you to turn around and show me how hard it is going to be for you to tuck away your bulge. - Nikki Daniels Penny Barber Kandii Kiss - sissytrainervids
Sissies like you should be tied up and teased
08:21
This is all happening since you were not following the rules. You had all of these chores around the house and you have not done any of them. - Amai Liu Jade Indica Jewell Marceau Nikki Brooks Samantha Grace Whitney Morgan - sissytrainervids
I will give your sissy ass exactly what you need
08:14
Ashley Sinclair's philosophy when it comes to guys that want to be pegged is to give them exactly what they want. That means your ass is going to get fucked. - Ashley Sinclair Alexis Grace - sissytrainervids
You look so pretty as a sissy girl
07:36
Aww you poor little girl you! It's time to play dress up with you today and I'm going to put you in the prettiest outfits I can find. You'll be wearing my pink bra and panties set while I find your - Allura Skye Danica Logan Natalie Laine - sissytrainervids
I will transform you into the perfect sissy girl
07:41
You envy girls and their pretty little outfits that they get to wear. You would just love to be able to do your hair like we do or wear a sweet scented perfume. - Bossy Delilah Carissa Montgomery Jade Indica Nikki Brooks Samantha Grace Whitney Morgan - sissytrainervids
I will make you look so sexy as a sissy girl
06:08
I've caught you going through my makeup, I've caught you going through my lingerie. Look, this needs to stop, and the only way I can come to terms with what's happening is if I turn you into a sissy. - Kneely Morgan - femdomvideos
You are going to look so cute as a sissy boy
07:29
Aww you poor little girl you! It's time to play dress up with you today and I'm going to put you in the prettiest outfits I can find. - Allura Skye Danica Logan Sadie Holmes Star Nine Goddess Rapture Natalie Laine Amai Liu - femdomvideos
Be a good little sissy girl
07:46
Are you ready to be Princess Anna's little sissy bitch tonight? She is going to dress you up like a girl, put some lipstick on your and shave your legs. She loves humiliating all her pathetic little - Alexis Grace Allura Skye Ashley Sinclair Natalie Laine - sissytrainervids
Mistress Mommy Spanks Round Sissy Ass
01:46
My favorite Mistress Mommy spanking her sissy subs fat round ass. - keswicksissy
I am here to teach you how to suck cock
08:27
All you sissy boys out there need to know how to give a proper blowjob. You cant call yourself a real sissy unless you know how to give a really big cock a ball draining blowjob. - Addie Juniper Chloe James Chrissy Daniels Jewell Marceau Samantha Grace Whitney Morgan - sissytrainervids
We will make you suck cock like a real sissy
07:40
We know that you'll do absolutely anything we ask, so that's why we're going to turn you into the perfect little female slut. - Kneely Morgan - femdomvideos
Sissy Maid in self bondage armbinder hogtie
39:54
hogtied in ballet boots with armbinder, harness gag covered with cum soaked panties.. good way to spend an afternoon - Derek6699
I can show you the secret to being a sissy boy slut
07:50
I want you to get into that pretty little frock that you got the other day, but before you do so, I think it’s important that you put on a bra and stuff it full of socks so you get the big, busty brea - Joanna Sweet - sissytrainervids
 JOI En Espanol, Especial CBT + Tortura y Juego Dados.
05:42
JOI En Espanol, Especial CBT + Tortura y Juego Dados. Prepara tu polla y tus huevos testiculos para la tortura y el dolor. - DaikoFextarJOI
I have always wanted a sissy dress up doll
08:35
I've always loved the idea of you being a dress up doll for me. I have such a great collection of panties and bras that will turn you into such a gorgeous girl. - Kneely Morgan - femdomvideos
Sissy Maid Self Bondage Aug28-2020
39:14
a slightly longer one locked in rigid arm/neck spreader bar... - Derek6699
I am going to make you dress like a sissy girl
06:29
Look at you, standing before me without a single shred of clothing on. How would anyone know that you were woman if you don’t dress the part? - Amai Liu - sissytrainervids
Put on these panties you little sissy bitch
07:23
Now, take your lipstick-covered lips and open them up, welcoming any cock that comes your way. We both know that you love nothing more than the idea of being a perfect little sissy. - Carissa Montgomery Caroline Pierce Gina Bang Jewell Marceau Nikki Brooks Whitney Morgan - sissytrainervids
I have a matching bra and panties set for you
05:26
I have a cute little sissy outfit I want you to wear. I think once you put this one, you will look like a real sissy girl. - Ashley Edmonds Ashley Sinclair Jean Bardot Taylor Raz Kandii Kiss - femdomvideos
You are about to take a strapon up your sissy ass
08:24
Lube it up for me with your mouth and then turn around. You're my personal bitch and today I'm going to fuck you deep in that ass. You say you've always wondered what it's like to be a woman. - Alexis Grace Nikki Delano Samantha Grace Whitney Morgan Jean Bardot Kandii Kiss - femdomvideos
Nylon Sissy Slave Cock Punishment
06:00
Submissive nylon crossdresser get his cock and balls tied up with a stocking and punished with slaps and the cane - fetishvids
I want to get really nasty with a sissy girl
06:31
We are going to dress you up like a pretty girl and we are so excited about that. Look what we got you! A nice bra with some glitter on it! This is going to look so good on you. - Lilith Lust - sissytrainervids
I will give you a total sissy makeover
07:06
Since you have helped me pick out my outfit for tonight, I am going to help you with yours. Let's start with your makeup because I want you to look your best. You can come closer. - Nikki Delano Samantha Grace - sissytrainervids
I will work hard to make you the prettiest sissy possible
06:40
I know it's going to take a lot of work but you'll look absolutely gorgeous when I dress you up and do your make-up. You'll wear my bra and panty set and we'll shave that nasty hair off your back. - Kneely Morgan - sissytrainervids
I will take you out dressed as a sissy girl
07:57
I know you have been admiring my cute outfits so I thought since you like them so my why don't you try them out yourself. Let's start with makeup. - Amai Liu Bossy Delilah Carissa Montgomery Jewell Marceau Nikki Brooks Nikki Daniels Samantha Grace Sovereign Syre Whitney Morgan Alex Love - femdomvideos
You can pretend to be one of the girls around me
06:12
We are going to have such a fun day turning you into a sissy girl. I will give you a bra and panty set and then do your makeup. - Kneely Morgan - sissytrainervids
I am going to make you into a sissy princess
07:29
Aww you poor little girl you! It's time to play dress up with you today and I'm going to put you in the prettiest outfits I can find. - Kneely Morgan - sissytrainervids
You are going to be my lil sissy girl
07:02
You envy girls and their pretty little outfits that they get to wear. You would just love to be able to do your hair like we do or wear a sweet scented perfume. - Bossy Delilah Carissa Montgomery Lucy Summers Nikki Daniels Nikki Delano Samantha Grace - sissytrainervids
I will use you as my personal sissy dress up dolls
06:02
Get your small balls and pathetic dick strapped into that lacey thong this second. That's it, make sure that it looks like you have a cute little pussy instead of that gross collection of bulges you h - Ashley Edmonds Ashley Sinclair Penny Barber Taylor Raz - femdomvideos