This is a HUGE step for most CDs & not to be taken lightly.
I've read several cases of this topic & expirienced it myself and i've yet to come across a story that is different.
My 1st Time:
At 17 i started dating a girl from college that i knew for about a year. We got on great & were like best friends. Anyway, i used my humor trick & joked about wearing tights 1 time in a conversation. Not long after there i was, with her in person wearing tights.
At the time i thought nothing of it, i was doing somthing i enjoyed and she had no problem with it. Then after came the old guilt & shame (you CDs know what I'm talking about) and within about 2 weeks the relationsip was over and i lost someone who was a great friend. Why? because i let my mind and negative thoughts get the better of me.
Crossdressers
You've just done something that alot of crossdressers dream about, realise that the person you dressed infront of is OK with it. I know, it's easier said then done.
Before you do something silly (like what i did) stop, think & talk to your girlfriend/friend.
Discuss what happened, more then likely these people have no idea how your mind thinks after dressing. For most this is all new to them.
Girlfriends/Friends
If your friend/boyfriend suddenly seems different after the incident talk to him!
Especially becuase its the first time the bad feelings seem 10x worse. Just reassure him, let him know that he has no reason to feel shame.
Reassurance is the key, sooner or later it will get lodged into his brain and hopefully squish the negative thoughts. Just ask if there's anything he'd like to talk about and that he can tell you anything.