Getting ready for a night out, I catch a glimpse of Emily in the mirror, no way are those shorts going to fit her new fat butt and belly!
I enjoy watching her struggle and get embarrased for a minute before realising if I dont help her squeeze herself into these, we won't be going out atall tonight!
After much tugging, breathing in, pulling to and fro - her ass is still hanging over the shorts. Will we ever get them on or has she gone past the point of being able to get into her usual clothes size?

This clip also contains light humiliation, teasing Emily about what hes...

Getting ready for a night out, I catch a glimpse of Emily in the mirror, no way are those shorts going to fit her new fat butt and belly!
I enjoy watching her struggle and get embarrased for a minute before realising if I dont help her squeeze herself into these, we won't be going out atall tonight!
After much tugging, breathing in, pulling to and fro - her ass is still hanging over the shorts. Will we ever get them on or has she gone past the point of being able to get into her usual clothes size?

This clip also contains light humiliation, teasing Emily about what hes been eating, how I managed to fit right into my shorts, telling her she needs to work out and advising her I dont think it's a good idea to try and pull tonight in what shes wearing, I mean, someone is going to have a shock when they try and get her nude!