Re: your first time
oh yes, mervyns...i had a similar experience, except that back in the early 90s i also had a thing for their own brand of knockoffs, pacific express.
in '93 i actually dressed up in a skirt and hose (quite badly, I think I sealed the deal with my regular old K-Swiss) and rode my bicycle to the mall. i was 15 then. i don't know what in the world i was thinking except that it was very cold and so i was very bundled up in like three coats. they were discontinuing the brand and so i got a white pair for $6.99. i found the nearest backlot i could and put those shoes on and rode my bike home in what must have been 30-degree weather (cold where i was from).
the past couple of years i have started going out (at night) in keds. of course, i have to be wearing a skirt or dress too. but yes, what an incredible mix of adrenalin and contentedness. i first would go to the local university and walk around campus - a good way to kind of get my courage up and practice without being seen by too many people. i worry i don't pass well.
this past week, though, i did what for me was a very brave thing and i stopped by a local coffee shop. they were having live music so there were tons of people...actually, it helped, because i didn't stand out (so much). i ordered a coffee and took it outside where i had a cigarette and every once in a while i would just peek down at my cute little black keds and smile. i am more worried about being recognized than harassed, i live in a very tolerant city for this type of behavior. it was liberating to be behind enough makeup and disguise that i didn't feel like i'd be recognized.
the feeling of wearing keds is incredible, but also the feeling of being an actor (actress?), being somebody else - i like that. in real life i don't smoke, i'm married and very happy. it is nice though to have a release for an urge that really doesn't ever go away. the urge for keds, that is...i go months or years without smoking, i actually can't even stand to be around smoke unless i'm in keds. weird but it is true.
i left the shop after it closed and went looking for another, but the only other one that was open...i was trying to find the womens' room, i couldn't, and so i got flustered and left. but i did take a very long walk and smoked quite a few more menthols while stopping under every streetlamp to look at my keds and smile again.