Tag: Crossdress humiliation - Page 4

118.8k 4min

Bend over and take it sissy boy

32.6k 6min

Put on this sexy sissy dress

136.9k 3min

Crossdressing sissy trainer humiliation

29.6k 6min

Put on this super cute pink lingerie

28.9k 6min

You can be my new sissy dress up doll

69.3k 9min

Get your tight little ass ready for some big cock

49.7k 8min

You are going to make a perfect sissy dress up doll

53.3k 13min

You should be dressed like a sissy and flogged

3.5M 7min

You are going to be my sissy anal slut

45.6k 8min

You are going to be my sissy anal slut

25.4k 7min

You look kind of sexy dressed as a sissy girl

142.5k 8min

Take off your clothes and put on this lingerie

103.2k 5min

We need to train your ass before you take a real cock

104k 9min

You look like you are hungry for some cock

540.6k 8min

I am going to make you my sissy anal slut

37.5k 10min

Take the pain you pathetic little sissy bitch

74.8k 2min

You know you love crossdressing

85.1k 6min

I want to see what you look like as a sissy girl

24.1k 6min

I love humiliating sissy boys like you

50.4k 8min

Take this hard cock up your ass balls deep

125.1k 9min

I am going to dress you up like a sissy and whip you

61.5k 6min

I picked out a cute sissy outfit for you

54k 3min

Making you go to the club dressed as a woman

76.1k 5min

This big strapon is going right up your asshole

76.8k 8min

You are nothing but a girly little bitch boy

95.3k 3min

You are going to look good as a little sissy slut

20.6k 6min

We want to see how you look in lingerie

218.8k 7min

I got a pretty pair of panties for your sissy ass

94.5k 8min

You can be my new sissy dress up doll

80.8k 5min

I'll make you into a real sissy slut

39.2k 6min

I will dress you up like a real sissy girl

29.2k 8min

You will look great once we get you all dressed up

100.5k 3min

Come be my crossdressing slave

18.8k 7min

You are taking this big dildo balls deep

32k 8min

You are going to be my new sissy boy

21.6k 8min

I love humiliating you like the sissy you are