Hi chatward,
Yes, technically you need a mil spec crimp tool, but you can get away with using a generic crimp tool providing it is small enough to achieve an effective crimp and you use it carefully.
As PaulSS says, once crimped the pins usually slip into place in the D-sub easily, but you do need to use an extractor if you need to take the pin out again - so be careful to get it in the right place first time.
Trig supply extra pins with the transponder, but if these have been lost / mislaid, they are usually very helpful if you ask nicely.
Regards
Peter