Just wondering if it's possible to skydive while binding or will I die?

Lol....I'm not sure what made you think binding while skydiving would possibly result in death... But that's definitely not the case. Death would be more a matter of parachute failure, operator error, etc.

My boss skydives but he never told me about this one. If there is an issue, I would suspect the shock of the opening combined with the binder might break a few ribs. If you need to attempt something like this, you should consider a lose binder to reduce the pressure on your body as the result of binding. A compression shirt might be a better option for this.

Up side if your sky diving odds are you will be wearing bulky layers to stay warm so even if the binder is a issue having a bit less tightness won't be noticed. Also I doubt that there would be a problem unless your binder is tight enough to restrict breathing.

I am reminded of a friend who hang glides and once told me that given how tight the harness is between your legs it's gotta be uncomfortable for guys. :-P

Serena

Well many ciswomen skydive. No doubt many wear sports bras etc. Doesn't seem to be an issue so why should it be for a transman?

Never could work out why anyone wants to jump out of a perfectly good plane and chant 'So far so good for 5000 meters 

If skydiving rocks you, just do it!

I saw a news report today on an old man skydive for the first time on his 100th birthday. If he survived why should a fit guy like you worry?

I've jumped out of 13 perfectly good airplanes I might add. Speaking from experience, it's not to be of concern. These were all done prior to me having top surgery as well.
If you've never skydived before, you're going to be on a tandem jump, aka, attached to someone who knows what they're doing. You're just along for the ride. Also, very unlikely that the opening shock would cause enough force to do any damage such as broken ribs.