Iterations are MD5(MD5(...(MD5(128 0 bits)))) with k nestings, and beginning from an input message which is 128 bits all 0.
Each hash digest is 128 bits and is a 128 bit input to the next iteration.
Bit strings are compared lexicographically, which means numerically when interpreted as 128 bit numbers (most to least significant bits).
This is a finite sequence, as there are only a finite number of hash digests (2^128 of them), but it is not known what maximum hash may be reached, nor when it is reached.
Because hash outputs are probabilistically equivalent to random values, there is a ~1/2 chance of the sequence ending at or before 46 terms, due to the underlying hash series forming a cycle. If reached, the expected value (with standard deviation) of a(46) is 2^(~64.6, s.d. ~9.5), on an underlying hash value of 2^128 - 2^(~63.1, s.d. ~9.7).
The first nonzero hash in the series, 0x4ae71336e44bf9bf79d2752e234818a5, in base 10 equals 99562681977162996006182885104198097061.
For a(27) = 20884436327980, the underlying hash is 0xfffffffffffbfbb5e5f5423502e812e1.