The aftermath of this incident was what really made it awkward
My 2nd year in college I got invited as a date to this big ass Greek banquet where all the sororities and fraternities show off their new people. I drank a 40 and a shot or two before we get there. When we get the dude who's handing out wrist bands for the 21+ hooks me up for no apparent reason other than he's down for people getting drunk. Drank another beer, more shots, and at this point I'm pretty drunk and having the time of my life watching all these fine college hoes in dresses do dances for everyone. As soon as the formalities are over shit turns into a dance party. The girl I came with as a date was a lesbian friend of mine, so that meant I could dance with any girls I pleased. My friend buys me a long island changing my physical state from "drunk" to "wasted." I'm dancing left and right with all these different fine ass girls, and surely enough, busted ones too. Don't remember but my friend said at one point I was dancing with the photographer lady who was probably 10 years older than me. I see this black girl that I had some previous history with that was my dates sorority sister. At a party just a week before at one point I had her alone in my bed, but was too big of a pussy at the time to even think about whippin' it out. She has her huge ass titz poppin out of her dress and shit, mad cleavage. I can see the line on her skin where the nipple meets the tit. So this girl has her camera and hands it to my friend to take a picture. In my drunken state I think to myself, "damn...it would be fucking hilarious if I could subtly yank on her dress slightly, exposing her nipple for the picture without her noticing." So I tell my friend to take the picture on 3 with this thought in my head. I count down, 1...2...3! and on 3 I drunkenly pull her dress down, revealing her fully exposed titty out for the world to see, (I found out later I had even broken the strap that held her dress.) Drunkenly not thinking anything of it, I immediately bounce to the dance floor to continue dancing with hoes. Apparently she just had a few shots, and started freaking out crying. Word spread instantly from person to person. All her sorority sisters found out about it, and so did a bunch of frat dudes they were friends with. Someone has to come up to me and tell me, "what the fuck did you just do?!" before I realize anything is wrong. My friends try to get me out of there, but before I can escape one of their dikey sisters corners me and cusses me out in front of a shit load of people. Buzz instantly gone, and some UFC lookin' frat dude comes up to me and tells me to leave.
I felt like shit about it for a couple of weeks. Couldn't walk through the union without feeling like the school perve. Apologized to her the following monday on campus, she cried, it sucked. Felt like shit about it for a while. Gave a formal apology to her at one of her sorority meetings in front of all the girls. The amazing thing is that they're all cool with me now. However, karma hit me pretty bad the following weekend when I was arrested for smoking weed at the dorms.
Looking back it was fucking awesome and I would do anything for a copy of that picture.
And one time my mom walked in on me masturbating, but that's a far less interesting story.