Great site. I've finally got up the courage to share my little foible!
I have no idea exactly where or when it started but I think it must have originated from being taken to the hair salon with my mother as a kid and seeing how she seemed to enjoy the pampering. Anyway, however it started, from my teens I have had a fantasy about being in a woman's hair salon and having a complicated updo done to my hair. What's weird is it's only the hairdo that is feminine - I always imagine I am still dressed in men's clothes although sometimes in my dreams I am naked.
Soon after I met the woman who is now my current wife, one time in bed after lovemaking, we were swapping secret fantasies. I told her about this fantasy of mine. Initially she just laughed, but a couple of weeks later, after a bottle of wine, she suggested we act it out. My hair is not very long, but she had a hairpiece and spent what was an amazing half hour or so putting my hair up for me. By the end, my cock was so hard I needed relief badly. I tried to kiss her, but she said it was just my fantasy and not hers but she wouldn't mind if I helped myself. I needed no more encouragement and came in a few seconds from touching myself.
Ever since about once a year, she will indulge my little fantasy. A few times she even made me up as well, which added even more spice to the whole thing.