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 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
07:26
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
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
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
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 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
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 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
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
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 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 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 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
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
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
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 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 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
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