Good evening,
My name is Brad, and I'm 29 years old. As a child I was never taught how to properly clean beneath my foreskin, which resulted in never having exposed my glans until I was seventeen.
This was a painful and slow process as it was very tight, and revealed excessive smegma (some of which were large chunks 1-2 inches wide and thick) With a daily routine this isn't much of a problem for me anymore, unless I don't clean for a full day where I get minor smegma.
Over the last few years I have been learning a lot about my body, stretching my foreskin and having sex for the first time. During the first time having sex, I found the sensation on the foreskin painful. And after the second or third time there were bleeding/cuts on the foreskin on the top side shaft.
Since stretching daily, the problem no longer occurs in this area, but instead has moved to the frenulum. However, my foreskin isn't particularly tight. I can retract my foreskin, and slide it up and over the head of my penis with ease. I can also stretch and pull my frenulum without much discomfort, but once entering a woman it begins to become uncomfortable with the friction.
I don't believe I suffer from phimosis, I personally believe it could be from having thin skin on my penis, or due to a large vein in that area (I can clearly see the veins of my penis, including their colour, however the pain is only in the frenulum) The pain is also excessive to the point that sex isn't enjoyable, but masturbation is fine.
Any advice or help would be appreciated, as I don't feel I could ever please a woman through penetration in my current condition, without considering an operation of some sort
I have also only had sex with one woman because of this issue, and I thought that perhaps with time and practice this may resolve itself. However I own a fleshlight which causes the same problem ongoing. Thank you.