Glenn1234

It depends on how much training you are willing/able to do, how much in shape you are physically (skeletal as well as the weight issue, back knees ankles and so on), and how acclimated you are to the bike (fit and so on).

The main issues will be pace (how quickly to complete it), terrain (as was mentioned 50 miles on flats is much different than 50 miles where part of the road you are on can be termed "the road from hell" for all the climbs), and nutrition (much of this will depend on your pace and time - there's nothing that kills a ride quicker than not getting enough water or the right kinds and amounts of food).

I will add too from experience (a 52 miler and a 57 miler at present), since your commute is 14 miles you'll probably need to get to the point in your training where you can do that and a little more in a quick fashion without resting to prove yourself ready for the 50 miler. In your place I'd probably shoot for another 5-10 mile ride a day when you commute, and then try longer distances to see what you will need to address and correct nutritionally, mechanically, and otherwise when you don't do the commute rides.

The only other factors I can think of are equipment (you probably already do that for your commutes, things like a tire patch kit, pump, and something for inclement weather), and if you haven't already looked into it get a pair of bike shorts. The biggest negative issue I ran into outside of my health on those 50+ mile rides is friction burns from being in the saddle so long.

Good luck on this. Depending on your fitness and health, 50 miles in 2 months shouldn't be out of the question given what you state you ride already.