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 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 will teach my favorite sissy how to suck cock
07:09
I know that you are a little sissy boy who is very curious about how it is like to be with a man and how to suck a dick. But the first thing you have to do is look presentable. - Diana Knight Nikki Delano - sissytrainervids
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 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 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 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 will doll you up like a total sissy slut
06:23
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. - Nikki Delano - sissytrainervids
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 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 will take you out to the club and find you some cock
06:57
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. - Amai Liu Gina Bang Jewell Marceau Nikki Brooks Nikki Daniels Penny Barber 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
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 - sissytrainervids
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
Are you ready to become my little sissy girl
06:44
Now, open your legs and show me what’s there. Ugh! Shave your legs, make them smooth for me. You know that pretty little girls do not have hair all over their bodies. - Bossy Delilah Carissa Montgomery Jade Indica Nikki Delano Samantha Grace daddysgirlss - 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
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 will turn you into a sissy cheerleader slut
07:27
Did you think that we were inviting you here today to have sex with us? That is never going to happen but we do have a surprise for you. - Carissa Montgomery Crystal Clark - sissytrainervids
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
I will let you try on my panties
08:11
Today I got you some new panties and a nice matching pink bra. Finally, you have earned yourself a slut thong! I know you have been working a lot on your make-up skills for me and it looks divine! - Jade Indica Nikki Delano Soraya Rico Elena De Luca Natalie Laine - 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 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 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
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 want to watch you suck your first cock
07:24
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. - Whitney Morgan Penny Barber Kandii Kiss - 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
I will make you into my pretty sissy princess
07:23
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. - Nikki Delano - sissytrainervids
You are invited on our girls night out
07:06
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. - Whitney Morgan - sissytrainervids
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 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
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 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 to see what you look like dressed as a sissy
06:55
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. - Kandii Kiss - 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
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
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
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
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
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
Turning you into a sissy is so much fun
07:21
Why are you so curious about me putting on my makeup? I think you want to learn how to be a lady. Come here, I will teach you. No, no, you cannot take it back now. - Amai Liu Jade Indica Nikki Delano Soraya Rico Star Nine - sissytrainervids
It's so much fun sissifying guys like you
07:38
Why are you so curious about me putting on my makeup? I think you want to learn how to be a lady. Come here, I will teach you. No, no, you cannot take it back now. - Amai Liu Jewell Marceau Lilith Lust Penny Barber Kandii Kiss - sissytrainervids
Put on this makeup and these panties
07:50
Why are you so curious about me putting on my makeup? I think you want to learn how to be a lady. Come here, I will teach you. No, no, you cannot take it back now. - Carissa Montgomery Diana Knight Nikki Daniels 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
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 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 just my sissy plaything
08:09
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? - Chelan Simmons Jade Indica Nikki Brooks Whitney Morgan Natalie Laine - sissytrainervids
Lets find a cock for your sissy ass
07:16
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. - Nikki Brooks - sissytrainervids
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 give you a total sissy makeover
07:48
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. - Amai Liu Nikki Delano Olivia Rose Samantha Grace Star Nine Alex Love - femdomvideos
I will doll you up like such a sissy slut
06:29
After dressing you up I am going to put you in these leopard shoes because you want to announce to the world that you are on a prowl. - Amai Liu Jewell Marceau Nikki Brooks - 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 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 want you to be our sissy girlfriend
06:56
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. - Nikki Delano Olivia Rose - sissytrainervids
I will help you pick out a girly outfit
07:29
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. - Jewell Marceau Nikki Daniels Penny Barber Kandii Kiss - femdomvideos
Feminizing guys like you is so much fun
07:52
Why are you so curious about me putting on my makeup? I think you want to learn how to be a lady. Come here, I will teach you. No, no, you cannot take it back now. - Jade Indica Samantha Grace Whitney Morgan - sissytrainervids
I will doll you up like such a little slut
07:41
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. - Jade Indica Penny Barber - femdomvideos
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 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 total sissy
08:21
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. - Jade Indica Nikki Delano Natalie Laine - 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 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 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 real sissy girl
06:24
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 - sissytrainervids
You have to wear panties if you want to cum
07:14
Hey babe, I have a new game for us to play. I know how much you love to jerk your cock while I encourage you, and while I enjoyed it for a while, now I need you to start making it more appropriate. - sissytrainervids
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 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
You are coming out with us dressed as a sissy
07:26
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. I am going to put on some foundation on your face. - Jade Indica Nikki Daniels Soraya Rico - sissytrainervids
I love feminizing cocksucking whores like you
06:22
I am so ready to dress you up into a pretty little slut that I know you can be. We are going to start by dressing you into this black thong since it is a sign that you want to fuck. - Kneely Morgan - sissytrainervids