Too small, too tight, too big? You're probably normal.
This weekend I came across a sex advice column on Female First where one worried reader asked, "I'm concerned about my penis my foreskin will not fit over the head and when I try to force it, it hurts. My penis size is also well below the national average. Am I okay?" Luckily, the writer Lucy Walton answered with a swift and assured, "You're okay, buddy." Because the truth is, if your foreskin just doesn't make it all the way over your penis when you're flaccid, nothing is wrong with you.
Just because it's often called a carrying case doesn't mean that foreskin needs to carry your whole package. If a sweatshirt only zips up to your chest, doesn't mean it can't keep you warm. As long as you don't force your skin in any way it doesn't want to go, the look of your foreskin is probably really ordinary. Just as all penises come in every size, shape, color, and thickness in the genital rainbow, so do foreskins.
However, for posterity, I'd like to cover the times when you might actually have a problem.
Phimosis
It's a condition where your foreskin is too tight to be pulled over the head of your penis. If you'd like a visual, it's like a turtleneck that can't be folded over. Most small boys have phimosis because their foreskin hasn't detached from their glans yet. It's perfectly normal. If however, by adulthood, phimosis continues and the penis grows to be swollen, painful, and red (you don't need the visual), the penis could be infected with balanitis, eczema, psoriasis, lichen planus, or even an STI. Generally, really good hygiene around the foreskin can prevent phimosis in adults. Ever heard of smegma? You don't wanna. It's a buildup that can gum up the works of your favorite member. A clean cock can do the trick. If the problem persists, adult circumcision is an option. While the recovery is initially unpleasant, long-term results are worth it. (And you'll have a whole "new penis.")
Paraphimosis
This is the case when your foreskin cannot return to its original position when it's retracted (after it's lovingly tugged.) If you have paraphimosis, usually the penis becomes painful, swollen, and needs emergency attention. We all know boners are full of blood, but the penis can't handle that much blood flow. Often times a local anesthetic and a little nudging by a medical professional will get the hood back in place. Beware, my hung friends, paraphimosis is a serious condition. Don't sit on that pain or try to fuck through it. Paraphimosis has lead to serious surgeries and amputations. Your penis is trying to tell you something by blimping up, so don't Bobbitt yourself.
Tight Fraenulum
Much like people can be tongue-tied, you can also be dick-tied. Sometimes your foreskin isn't the issue, it's the elastic band of tissue connecting your foreskin to your shaft. Think of it as a dog with too tight of a leash, only this leash is actually a fraenulum. This can be aided in two ways. The first is accidentally tearing your fraenulum in bed or during masturbation. Yes, this is when your free surgery is actually masquerading as a terrible sex injury. The other option is actual medical surgery to help loosen, break, or cut it. There is a silver lining, though. After fraenulum surgery, you'll have to take part in rehabilitative stretching exercises post-op. As if you all weren't already exercising that skin.
Image courtesy of Paramount.