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: