It might. This is one of the reasons circumcision got so popular... The foreskin can become tight. If you don't mind my asking, how old are you? These issues can occur at any time but are most common in the teens and twenties. Before you start stretching anything see a doc, but a bit of extra lubrication might be all you need.
Creepy as it sounds, and I am not a perv, you might want to check out some natural parenting websites. One of my friends has two little boys and knows more about foreskins that I can believe. I only recommend it because the info is straight forward and geared for those of us who do not have phd after our names.