Dildo Challenge

I’m a loser.
I’m a loser.
Cucky accepted the challenge. He really shouldn’t have.
Cucky accepted the challenge. He really shouldn ...
Cucky is extremely nervous. He knows the penalty for losing the dildo challenge.
Cucky is extremely nervous. He knows the penalt ...
So one-sided, isn’t it?
So one-sided, isn’t it?
Does it get more embarrassing for a cucky bitch than this?
Does it get more embarrassing for a cucky bitch ...
Is anyone else this humiliated?
Is anyone else this humiliated?
Tonight’s matchup: 9 inch thick dildo vs. cucky’s 3 inch pee pee. The winner is… not you sissy cuck!
Tonight’s matchup: 9 inch thick dildo vs. cucky ...
The giant wins.
The giant wins.
Barely past the head, and that’s only because of the lock of my chastity cage. #patheticcuck
Barely past the head, and that’s only because o ...
Sissy boy comes up short again!
Sissy boy comes up short again!
Sissy Webcam Trainers
Again, the results tell all.
Again, the results tell all.
Coming up short in black and pink panties.
Coming up short in black and pink panties.
When I think I’m big, or even average, I’m stripped naked and reminded of why I’m not. So humili ...
When I think I’m big, or even average, I’m stri ...
Penis Ratings
Big dick versus a nonexistent one. I belong in this 1.5 inch micro chastity cage, don’t you think?
Big dick versus a nonexistent one. I belong in ...
6
chastecuck They do, especially when I see them penetrating a woman and making her orgasm. I was never ...
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SUB_4_DAD
littledickwanker jay Nice black dildo. Yeah, when I was with Debbie I had to use a BBW dildo on HER. It wasn't th...
What’s under cucky’s skirt? A boner a little less than 4 inches!
What’s under cucky’s skirt? A boner a little le ...
When you wear panties instead of men’s underwear, this is the size of your boner.
When you wear panties instead of men’s underwea ...
Choices choices
Choices choices
Is this actually even a comparison?
Is this actually even a comparison?
Show your penis to women online
Unzipped panties for a chastity vs dildo comparison.
Unzipped panties for a chastity vs dildo compar ...
Rock hard vs an 8 inch dildo. Still not halfway.
Rock hard vs an 8 inch dildo. Still not halfway.
Coming up just a little short
Coming up just a little short
My head and balls are smaller than the head of this dildo. Absolutely amazing
My head and balls are smaller than the head of ...

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