"Three of my friends and I (all of us women) decided to book a room at the most upscale hotel in town for New Year's Eve and do it up crazy style. We had gotten hold of some illicit substances and were all feeling fabulous and having a great time. At some point, we figured out there was a pool but we had not thought to pack swimsuits. A minor inconvenience, we simply went down in our underwear. And after having a rollicking good time we decided to take our dripping wet, underwear-clad selves back to our rooms. Well, what we had lost sight of was that in this very swanky hotel and there was a huge formal NYE event going on. Like wealthy people all decked out in tuxedos and ball gowns. It's a real 'old money,' traditional kind of hotel. So imagine our shock and horror when we tried to very quietly and unobtrusively slink onto the elevator and find that we had to squeeze into a car full of immaculately dressed guests who all went dead quiet and tried to not so subtly press themselves against the walls. It was a veeerrrrry long ride up to our floor."
"I was a Chief Petty Officer berthed in the temporary Bachelor Officers' Quarters. Two rooms shared a bathroom. In the morning I entered the bathroom, buck naked, for a shower. At the same time, also buck naked, entered a very buxom female. Assuming she was an officer, I quickly came to attention (embarrassingly all of me) and saluted, turned around and returned to my room."
"Before my weight loss surgery, I was 110 lbs overweight. Three other teachers and I went to a conference and had to share a hotel room together. I was getting super constipated because I was uncomfortable using the restroom to poop while in such close proximity to my coworkers. The last day I could no longer take it so I got up at 4 AM while they were still sleeping. It was hideous, I strained and pushed for what seemed like ages... nothing. Finally, I dug my feet into the floor with all I had and pressed my back against the back of the toilet and gave it my all. CRAAACK! The frickin toilet cracked from one of the bolts and all up the pedestal!!! Water was leaking everywhere! All three of my coworkers came running to the door to see if I was okay. Humiliating. I had to call the hotel desk and pretend like the toilet cracked out of nowhere. Everyone was so nice, I don't think anyone believed me for a second. The worst part, I was still constipated."
"On frequent business trips to a particular city, I would rendezvous with another executive who lived there. The arrangement was passionate but strictly hooking up, and it was very much a secret. We always met in my suite at the same hotel. He would come in through a side entrance and then take the stairs to my room in order to protect both our reputations. On one highly anticipated weekend, I had a shipment containing hundreds of dollars worth of lingerie and adult toys sent to me at a local friend's house, then I brought it to my room. This stuff made 50 Shades look like the bunny slopes. After our night together, I packed it all back into the box, buried in the packing materials so housekeeping wouldn't be disturbed by any of it. Well, somehow they assumed the box was empty and threw it out. I got back to my room, saw it was gone and panicked. I called the front desk to have it returned to me, hoping the housekeeper would remember the box and quickly identify it. It turns out they discard LOTS of boxes, and in order to find which one was mine they ended up opening and sorting through all of them. I will never forget the smirking expression on the face of the bellman who brought it to my room. I am 100% certain rumors spread among the staff, as every glance followed me every time I crossed the lobby, and male employees to this day still greet me with extra enthusiasm. In retrospect, it's likely they thought I was a professional dominatrix or something of the sort."
"Luckily this happened before social media got big, but it did not happen before camera phones... Years ago two friends and I got a hotel room for the night. We went drinking all day long on empty stomachs. To make things worse, the bar had a special on giant Long Island Iced Teas that would put down a horse. A few hours and way too many long islands passed, and Friend 1 passed out on the bar and was dragged out by the bouncers and put into a cab, unbeknownst to me and Friend 2. We went looking for him, eventually making our way back to the hotel. He was there alright, completely passed out dead to the world and had flipped the latch on the inside of the door that prevents you from opening it from the outside. After much banging and screaming, we were able to get the superintendent to help us. I was 10 long islands deep at this point, and I couldn't take it anymore. I passed out on the floor while the super was removing the door. I don't remember anything that happened next, but a lot of other people did. I couldn't believe what happened when I got in the elevator later that day, I was so embarrassed.