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
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
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
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 chose the perfect sissy outfit for you
07:26
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 . - Gia Steel Kandii Kiss - 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
We are going to dress you up like a sissy
06:26
Hey, you pathetic little dweeb! We got you some presents while we were out today and now is your chance to show us just how much they mean to you. - Nikki Daniels Nikki Delano Samantha Grace Penny Barber Kandii Kiss - sissytrainervids
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
I want you to suck cock like a real sissy
08:15
If you want to play with me today, you will have to play under my rules. I bet you are curious to learn what they are. Well, if you haven't noticed, I really enjoy the things which are girly. - Bossy Delilah Diana Knight Jade Indica Jewell Marceau Nikki Brooks Whitney Morgan Natalie Laine - sissytrainervids
I will dress you up like a sissy for our night out
07:43
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. - Nikki Daniels Olivia Rose Penny Barber - sissytrainervids
Put on the sissy boy outfit I picked out for you
06:19
I want you to get into that pretty little frock that you got the other day, but first put on a bra and stuff it full of socks so you get the big, busty breasts you’ve always dreamed of having. - Caroline Pierce Kandii Kiss - sissytrainervids
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
I will dress you up like a total sissy girl slut
06:42
I hope you are ready for me to dress you up! I cannot wait for you to get your dick in these cute blue panties. Look! They even have a small bow on them. - Gia Steel Jewell Marceau Lilith Lust Nikki Daniels Olivia Rose Penny Barber Kandii Kiss - sissytrainervids
I want you to be my new sissy sex slave
07:27
I think you are the sweetest man I have even known. Do people tell you that you are too nice sometimes? There is a kind of delicate innocence about you. - Nikki Daniels Penny Barber Kandii Kiss - 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
You are going to be my real life sissy plaything
06:38
I will let you wear my clothes which are going to fit you nicely. I think some of my panties would make you look so cute. Maybe some black silky ones, what do you think? - sissytrainervids
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
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
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
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
You are such a pretty little sissy girl
07:40
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 - Alexis Grace Sadie Holmes Taylor Raz Kandii Kiss Natalie Laine - sissytrainervids
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 want to see you sucking cock like a real sissy
06:49
If you want to play with me today, you will have to play under my rules. I bet you are curious to learn what they are. Well, if you haven't noticed, I really enjoy the things which are girly. - Jewell Marceau Kandii Kiss - sissytrainervids
I want you to come on a girls' night out as a sissy
06:37
I want to invite you for a girls' night out. I could not think of another girlfriend other than you to spend my evening with. I am going to dress you up so you could hang out with my friends and me. - Amai Liu Diana Knight Jewell Marceau Olivia Rose 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 want you to join us for a girls' night out as a sissy
07:56
I want to invite you for a girls' night out. I could not think of another girlfriend other than you to spend my evening with. I am going to dress you up so you could hang out with my friends and me. - Bossy Delilah Nikki Brooks Olivia Rose Whitney Morgan Kandii Kiss - sissytrainervids
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 the perfect outfit for my little sissy slave
06:52
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. - Kneely Morgan - femdomvideos
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
I will completely transform you into a sissy slave
08:38
Are you getting kind of hard over these white panties and the thought of wearing them? Maybe you would like to be fucked while wearing these. - Amai Liu Jewell Marceau Whitney Morgan Penny Barber - sissytrainervids