Cock Too Big / Too Deep / Won't Fit / Asking To Stop Or Go Slower

Just wondering - how are Milfs different from women in general?
IMHO, a MILF tends to have less inhibitions and seems to be more in tune with her body. Trying to think how to put this into words. I would suggest a woman leans towards mutual, it’s equal give and take, as much about you as it is her. With a milf, I think it leans to “more about her” and a little bit more submissive quality, she knows exactly what she wants and how to get there. (not suggesting that women don’t) I feel that boundaries are more easily tested and exceeded with a milf. To flip it around, a younger man in his 20’s, eager, willing, wants to please, just happy to be there, vs- a 40-50 year old man that’s also happy but is going to test your limits, take what he wants while also getting you there. I’d suggest women more align with the younger man and milfs more align with the older experienced scenario.
 
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I remember seeing a amateur/homemade video of a guy and an Asian escort which fits this criteria. But it had so much more to it.

The scene is starts with her getting him hard on a leather couch with his friend creepily watching in the background, over his shoulder. He gets hard, applies the condom, she lies down and he tries to penetrate. After a 20 second or so struggle, he barely gets the tip in (I’d guess) and prematurely ejaculates. Afterwards he has a nightmare actually getting the condom off because of how thick his dick is.

A comedy of errors really. He’s embarrassed, his friend is laughing away in the background but she’s really cute and understanding. Some snapshots of the scene for anyone interested:
 

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I remember seeing a amateur/homemade video of a guy and an Asian escort which fits this criteria. But it had so much more to it.

The scene is starts with her getting him hard on a leather couch with his friend creepily watching in the background, over his shoulder. He gets hard, applies the condom, she lies down and he tries to penetrate. After a 20 second or so struggle, he barely gets the tip in (I’d guess) and prematurely ejaculates. Afterwards he has a nightmare actually getting the condom off because of how thick his dick is.

A comedy of errors really. He’s embarrassed, his friend is laughing away in the background but she’s really cute and understanding. Some snapshots of the scene for anyone interested:

If you're going to fuck a sex worker at least empty your balls a few hours prior, otherwise it's a waste of money
 
I remember seeing a amateur/homemade video of a guy and an Asian escort which fits this criteria. But it had so much more to it.

The scene is starts with her getting him hard on a leather couch with his friend creepily watching in the background, over his shoulder. He gets hard, applies the condom, she lies down and he tries to penetrate. After a 20 second or so struggle, he barely gets the tip in (I’d guess) and prematurely ejaculates. Afterwards he has a nightmare actually getting the condom off because of how thick his dick is.

A comedy of errors really. He’s embarrassed, his friend is laughing away in the background but she’s really cute and understanding. Some snapshots of the scene for anyone interested:
Found it:
Asian Prostitute Causes Premature Ejaculation — PornOne ex vPorn