"Sissy boy crossdressing" About 51,703 videos found - Page 20

You are such a cute little man slut
9min
428.4k

You are such a cute little man slut

Both of these toys are going up your ass tonight
9min
11.2k

Both of these toys are going up your ass tonight

I always knew you were secretly a sissy girl
7min
21.5k

I always knew you were secretly a sissy girl

I will train your sissy ass with a series of dildos
8min
114k

I will train your sissy ass with a series of dildos

You have to earn your place as my personal bitch
5min
16.7k

You have to earn your place as my personal bitch

I laid out a sissy outfit for you to put on
6min
22.5k

I laid out a sissy outfit for you to put on

Put on this dress and get on your knees
4min
84k

Put on this dress and get on your knees

Fat cock to ruin your virgin ass
10min
6.2k

Fat cock to ruin your virgin ass

You will be begging to be my bitch
6min
25.2k

You will be begging to be my bitch

You are a pretty little sissy girl aren’t you
7min
64.1k

You are a pretty little sissy girl aren’t you

You are my favorite sissy bitch
7min
28.5k

You are my favorite sissy bitch

You actually look pretty cute as a sissy girl
6min
26.8k

You actually look pretty cute as a sissy girl

You are a sissy bitch and you know it
6min
91.5k

You are a sissy bitch and you know it

Lets pick out a sexy sissy outfit for you to wear tonight
7min
18.9k

Lets pick out a sexy sissy outfit for you to wear tonight

You look good in a pair of my stockings
2min
79.6k

You look good in a pair of my stockings

I found a hung stud who wants to pound your sissy ass
15min
1.2M

I found a hung stud who wants to pound your sissy ass

I will train you to be the perfect sissy slave
8min
21.2k

I will train you to be the perfect sissy slave

You will look so much better as a sissy girl
7min
25.3k

You will look so much better as a sissy girl

Dress like a sissy or face your punishment
5min
420.6k

Dress like a sissy or face your punishment

I know you are a total sissy deep down inside
6min
85k

I know you are a total sissy deep down inside

Dressing you like a sissy girl is so much fun
5min
26.8k

Dressing you like a sissy girl is so much fun

Whipped silly
5min
23.2k

Whipped silly

You look like you are hungry for some cock
9min
103.4k

You look like you are hungry for some cock

I think you will be an incredible sissy girl
7min
14.1k

I think you will be an incredible sissy girl

I bet you can fit in these cute little panties
6min
13.2k

I bet you can fit in these cute little panties

I have some sexy sissy lingerie for you to wear
7min
219.4k

I have some sexy sissy lingerie for you to wear

Humiliating you with sexy girls clothes
5min
20.2k

Humiliating you with sexy girls clothes

This fat dildo is going all the way up your ass
8min
16.2k

This fat dildo is going all the way up your ass

You have to dress in womens clothes from now on
4min
103.7k

You have to dress in womens clothes from now on

Dressing you up like a little slut is too much fun
5min
62k

Dressing you up like a little slut is too much fun

I want to see you dressed up as a sissy
6min
115.6k

I want to see you dressed up as a sissy

Let out your sissy side and put on these panties
8min
247k

Let out your sissy side and put on these panties

I am going to make you my sissy bitch
2min
48.3k

I am going to make you my sissy bitch

I cant wait to make you into a little sissy girl
8min
104.9k

I cant wait to make you into a little sissy girl

You are now my pretty little crossdresser sissy doll
3min
68.8k

You are now my pretty little crossdresser sissy doll

I know you have been trying on my clothes
4min
43.1k

I know you have been trying on my clothes

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