Lots of size talk lately, I thought I'd give it from a guy who's 32, has a small dick and could not give a fuck.
I lost my virginity when I was 18. First a little back story previous to that. I'm circumsized. When I was 12ish, I noticed a lump growing on the side of my penis. I of course was positive that it was cancer and I was disfigured and was going to die. This was before google/internet anonymity/etc. I had ongoing confidence issues throughout my teens. In my mind, this lump was enormous, when in fact it was smaller than a pee and not noticeable to the naked eye, only when feeling around down there. I was friends with a girl for a long time (what the kids today are calling "friendzoned" (which doesn't exist, btw)) and after a year or so of being super close, she eventually got interested in me in that way. We made out (first girl I had kissed even), it was great, ended up fingering her to orgasm, it was everything I hoped for. The next day, it was my turn, I was ready to die, my dick tumor was about to be found out, I stopped her, tearing up, I told her. She said she didn't care, but we'd take it slow. Things went down, afterwards I asked, she said she didn't notice. The point of this part of the story is that I can empathize with the virgins that are terrified of what they're packing and it leading to them not being able to be comfortable with themselves to the point of it crippling their sexual development.
Moving on. It being her first up close and personal time with a penis, she thought it was huge, I didn't know any better, so I agreed that it was, in fact, huge. We dated for a couple of years and then split up. Afterwards, I decided to finally go to a urologist and have my cancer checked out. Turns out it was nothing, it took about 10 minutes to fix and I drove myself home. All that stress, anxiety, self hate for nothing. Then I went to college. My confidence is at an all time high. I'm getting laid left and right. Some one night stands, some week+ long relationships. Some a month, some 6 months. Lots of sex, lots of blow jobs, almost always coming back for more. So, I never once thought of my penis size (besides that I'm a grower, not a shower, so I knew getting naked flaccid was a no go). Move onto age 23, I meet the one. Sex is great, everything's great. No complaints in the bedroom, making her cum was always job 1 (it's not a job, it's the best part, imo). A few years go by, we hit a rough patch and split up for a couple month or two. I sleep with some more girls, all multiple times, all with no complaints. I even go back and sleep with my first girlfriend, who is actually married at the time (I know, I know) to a guy that had a much bigger penis than mine (she told me when they started dating), but it didn't phase me for a second, cause mine worked, I made girls cum, everybody wins.
Fast forward, get back with girl, she becomes wife. Sex is great still. We get divorced a year ago. Back on the horse…I start having sex again, all is well. Been with multiple women since then, not one complaint again, all back for seconds (thirds, etc).
Not until I started browsing /r/sex about 6 months ago did I find out that my 4.5in penis is small. Boy was my face red! All these years, I've been confidently speaking to women, having meaningful (some not so meaningful) relationships, and having great sex and not once did I look down and feel the shame that everybody seems to be trying to force onto me.
I'm not ashamed. It's a part of my body. It will be there until the day I die (hopefully). And it's never going to change (for the better). So it's "small", who gives a rats ass? If any of the women I've slept with have cared, then fuck 'em, as the kids are saying these days "doesn't matter, had sex". If they didn't care, which most women who get themselves in a situation where a penis is about to enter them, don't since they've already gotten to that point, then it does not matter, the hard part's over.
If a woman is shallow enough to care about the size of your dick then all you're missing out on is some sex that does not matter. If you still want to have sex with that person, even though she's superficial enough to rule you out because of your dick size, then you're just as superficial as her for still wanting to fuck someone that is that superficial. What matters is that you find someone who likes you for you, all that other shit works itself out.
Fuck size shaming. It's getting really old and there's seriously no reason for it.
EDIT: I kind of went on a rant there…I guess what my overall point was that dammit dudes, I know it's easier said than done, but just get some confidence. I'm not a generally confident dude, I'm overweight, unemployed, live with my parents, but I forget about all that when I need to. I can't always turn it off, there are days when I hate everything about me, but in the end "nobody cares more about you do than you". You are the only one stopping yourself. Haven't been able to tell that girl that you've been staring at everyday that she's cute? That's on you, seriously, go and tell her. If she doesn't like it, move on, at least you know and you're not just a dude staring and wondering what could be. I'm going to fill this with cliches. It's better to regret something you have done then something you haven't. Everything I just said has nothing to do with the size of your dick, so get over it.
EDIT 2: TL:DR DM:HS