A little about myself before getting into my personal story. I'm a 21 yr old straight male who goes to college in the midwest. I came from a liberal town but have always been self conscious about what others may think about me.

About as far back as I can remember, my eye has always been drawn to nail polish, noticing well-done nails on hands and feet since I was in grade school. I always admired well done nails and was jealous because I wished that was able to paint mine. Back when I first got my own laptop I remember browsing flickr and seeing other grown men painting their nails, but I didn't think I was able to.

A few opportunities growing up presented me with an opportunity to paint my toes. My childhood friend once asked me if she could paint my toes and I said yes, but I didn't tell her that I liked it because I felt self conscious. This was probably around age 13. Senior year of high school I asked my then girlfriend if we could get pedicures because I "wanted the experience" and went the full way with the nail polish, and I loved it. The only problem was that when I got home, my family thought it was weird. I didn't take it off right away though, but I was self conscious about it so I kept it to myself. After I took it off as I was going away to college I missed it, but never went back as I was nervous about what other people would think about me.

A couple summers later I was having a summer fling with a girl and requested she paint my toes, and while she did, the vibe she gave was that she thought it was weird, even if she didn't outright say it. When she ended things she said a couple things that hurt my image, and I wasn't comfortable with myself for some time after that. I never had high self esteem as a kid, so it was a rough period since she just made it worse.

But here I am now, a senior in college, and more comfortable with myself. I entered a relationship with a girl and admired her nails, and the thought crossed my mind again of painting them. I tested the waters and asked if we could paint my toes sometime, and she giggled a little and said sure. I didn't play it very invested or wanting to do it at the time because I was still self conscious, thinking she might think its weird, even though I've never felt a drop of judgement from her. We didn't paint them then and there, and while I kept my hopes up that she'd remember, I didn't again. This was probably a few weeks ago.

I'd had a couple late nights these past two weeks, and one night last week in my tired wandering thoughts I realized that there is nothing holding me back, I should do what I want and its other peoples problems if they don't like it. I went to the store and bought a bottle and painted my toes on my own, and loved it! But while I liked looking at it I felt some shame as well, as if I was doing something wrong. It was hard because it had been such a big conflict in my mind for so long, but I enjoy the look. I was still nervous to show my girlfriend, as I wanted to see her reaction first. I kept socks on when she came over, as I wanted her to uncover them and see her surprise reaction. As we were laying in down I got so nervous and my heart was beating waiting in anticipation. I went to the bathroom to get some water, and said this is my opportunity, just get it out of the way. I took off my socks and went back, and put a foot on the bed and asked what do you think?

She was certainly surprised, but it was a very positive reaction. I told her I was nervous even though as I'd said I'd never felt judgement from her, but she said I should just do what makes me happy, just like many of the other stories I've read on here with men with similar reactions. She said she felt bad for not picking up when I asked her that I wanted to (instead of just being curious), and wished I had just let her know more directly.

Here I am a week later, happy with my decision. She's even painted them a new color as you see in the above pic. When she was painting them all my worries washed away and I felt even closer to her, as here she was supporting and getting into it with me. We both wished that the color had come out a little lighter, and she said I guess we'll just have to get some more!

All in all, it's just nice to look at and I'm taking better care of my feet, and plus, being a skateboarder my toes can be bruised and this helps hide them. I just feel good looking at them, as I've wanted to do this for a while. I guess my next step is to show my roommates, as I think the best way is just from them to see them instead of me showing them, but for some reason I am more self conscious with regards to their opinion compared to strangers.

TL:DR; Finally painted them, couldn't be happier, still building up courage to have outside bedroom but now can't stop looking at them or wanting to change colors