I make one nearly every year.... if not, two.
I am a MtF crossplayer, so now that that is out of the way, here we go.
One time at Anime Boston *2008 I think*, my friends were in Dunkin Donuts outside of the Hynes. I was dressed as Chii *And a bad one at that* and an elderly lady walked up to me and said "I love your dress.
" I said thank you, and we started talking a bit. She asked me if I knew who everyone was cosplaying as, and I told her each one I knew. She then told me she always came by every year to watch the costumes because it fascinated her. The whole moment was very touching for me. I haven't seen her in a few years though. Then again, I wouldn't honestly remember her by face, I am terrible like that. :/
Otakon 2012 had a few events. I was dressed as Cardcaptor Sakura. One that gets me is when I was leaving the Masquerade Saturday, we were outside the convention center, and a non-con-goer ran up to me and said "Are you a guy?!" I said yeah, and she asked for a picture. When I posed, she said "Say 'I'm a naughty boy!'".... My friends and I joked about that all night long..... heck all week.
Otakon 2012 again, I was up in a lobby Friday night and a Char Aznable who was very..... engaging for a lack of a better word, came up to me, asked if I was a guy, and I said yeah. He said "Oh, we need to get a picture!" The girl with him got the picture of me and him together. He was alot taller than me, so I guess it kinda filled the illusion I was small, funny enough. *5'8*... anywho, they were about to go away, and then he scouts out a Pedobear, and he is like OH! We are getting our pictures taken with the Pedobear!".... Then he grabbed my wrist and tugged me along to get the pictures done. It was amusing as all hell.
Anime Boston 2005, my friend and I were walking down the hallway, and a guy that looked like Santa *not dressed as, just the beard and glasses* came out of a panel room, opened up the con chowda paper, and asked us *We were like 16 or 17* "Do you know if this Hentai has a sequel or not?"..... We said "Uhh.... we don't know, sorry"..... then we laughed it off and walked away. Well, laughed after we were away.
Anime Boston 2012, I was in the Family Feud gameshow as Sakura here as well. I got chosen for a team. When it was my turn to answer a question, I said "Uhh... " in the mic thinking, and the host lady was like "Wait, you're a guy?!".... the audience laughed, and all gameshow long, she called me "Secret surprise"... Dear God, it was funny. Our team ended up winning too.
Anime Boston 2011, my friends and I were playing Pictionary Thursday night in the Hotel. We were on the last square, me and this girl, and she had to draw "Helmet".... Well, I was looking at it like a UFO or something, and before the timer ran out... about 75% full still, she was like "If you don't get this, I am going to kick your ass." I was like.... Oh boy.... I never got it, so I got up, and ran into the bathroom and locked the door. All of a sudden, I hear a door slam. I open the bathroom door, and ask my other friends "Did she just run out into the hall?"..... they laughed saying yeah. She came back after I relocated myself behind the recliner and said "Damn, he runs fast!"
Anime Boston 2011 again, Sunday on the third floor, I started singing "I touch myself" outloud. Same girl above joined in on me when I was saying "When I think ABOUT YOU".... I then stopped and she yelled out without me "I touch myself!".... a guy nearby was like "I am glad to hear you touch yourself when you think about me!".... Laughed my ass off.
Anime Boston .....2007 I think?... Maybe 8 or 9.... same girl again, she was dressed as Lust from FMA. We were walking to the Train Station, and she crossed a crosswalk far ahead of us. We had to wait and she was alone on the other side of the street. A guy walked up to her and started talking, and we all were like "....What's that guy talking to her about...?"..... We cross the street, and she comes over and whispers to us "He asked if I was a prostitute!".... God, that made that night for us.
Anime Boston 2006, late Saturday night, there was a guy crossplaying Lulu from FFX outside smoking, and as we passed him, he was like "Be careful out here at night, there's some strange people".... back then, the expression on his face and the fact he was dressed as Lulu when saying that was amusing as hell.