Thanks for your query,based on the facts that you have posted it appears that you have stricture urethra
and doing urethral dilatation frequently.
.Please consult qualified urologist
for evaluation and discuss with him regarding option of Urothroplasty to treat your stricture problem permanently so that you can avoid doing dilatation and traumatising your urethra further.
As regards your inability to retract foreskin completely it is due to Phimosis and you need to get circumcised .