Hello, Welcome to Healthcare Magic. I have read your question fully and understand your concerns. From what you have mentioned I suspect that you are having a short frenulum (a band of elastic tissue that connects the foreskin and glans of the penis) which is preventing the full retraction of your foreskin. This short frenulum is called frenulum breve. This can sometimes cause painful penile erections and can also tear when having intercourse leading to pain. (Normally this frenulum is long and helps the foreskin to easily retract over the glans penis). I would advise you to visit an urologist or a surgeon who deals with penile problems. You may be suggested a surgery called Frenuloplasty where the frenulum is divided and sutured back. I hope this answer has helped you. Thank you Regards Dr Sunita Sayammagaru