Sharing a recent experience I had:

Over the course of my life I knew I was attracted to long, luscious hair, and I discovered trichophilia and hairjobs in my late teens. I had experimented in different settings and found I really just love wrapping long, thick, soft, loose hair around my shaft and using the loose hair in my hand to stroke my cock. I also loved leaving messy facials on girls where some cum ended up in their hair, I had previously been too embarrassed to ask to cum in girls hair directly in fear that the idea was strange to them.

Recently I have a new long term partner with almost waist length thick hair and one night I just went for it. While she was sucking my dick, I told her to lick my balls, and I grabbed all the hair I could in one hand, and wrapped it around my cock and started stroking. To my pleasant surprise, she was immediately into it.

"Oh yeah you want to cum in my hair? Cum in my hair baby," she said over and over, while licking my balls, while I stroked myself with her hair.

I could only last a couple minutes before I came with all of her hair wrapped around my cock, making a sticky mess in her hair.