What are some of your most memorable, funniest experiences in a hotel when "hobbying"?

Waiting for the gal to show up, I heard a knock at the door and answered it.

if we ignore "horrifying". Yikes!

I had just finished an outcall date and I hopped into the shower after the lady left. I thought I heard someone come in the room after she left but you know how you think you hear things when in the shower but turns out to be nothing? Well...then I heard two women laughing INSIDE my bathroom! I pull back the shower curtain and there is my date with another lady...who was a good friend and a woman I had seen many times!
Turns out my date was leaving and just so happened to run into the other lady in the lobby on their way out. She was providing her services to another client in the same hotel. They got to talking, realized one was my reference for the other, and decided a little surprise. She had the room key because I gave it to her to get out the parking lot for free. To this day, the one lady I still keep in touch with brings it up from time to time. Too funny thinking about it now but freaked me out then.

most recently in Sydney last year. But mostly in New York, CT, and NJ, not to mention Costa Rica, Panama and Peru. And I'm damned if I can recall any serious drama. Just some great times. So I guess I'm lucky.
Sorry, no stories.

I still remember exactly that lil noon time tryst..It's long but worth the read.
And yes, those are the actual casualties..lol

I have spent over five years in hotels during my career, so I have some stories, but not in the context of the hobby.

Wow now this is amazing!

Her room was in a weird spot, and the housekeeping crew was in the hall. I realized I had passed my ATF'S room, and turned around. The housekeeping supervisor asked "Are you looking for room 66?" Of course, yes, that was the one I was looking for. I couldn't walk out of there without arousing suspicion, so I just knocked and hoped for the best. My ATF let me in, noting the housekeeping crew, and looked at me with her eyes the size of saucers. Once the door was closed, we both busted out laughing and went about our business. Luck was with us, and there were no further incidents.

this dallas escort was 20 minutes late .. why ..she wound up going to the hotel next door and knocking that hotel's same room number as mine and ...    the guy was certainly flustered and it took her a minute to realize he wasn't her client  and then left for me.   he was probably disappointed .. but would have given that hotel a really good Yelp review for service LOL

I've been hobbying 10 years, and been with pretty much every flavor of girl imaginable.  Most will at least try to act like they are having a good time.  Then came the time I was having fun trying different positions with a really sexy little black lady, and while really going at it in doggy, she grabs the TV remote and says......  mind if I catch the Raiders game????  

Set up an appointment with an agency I know and trust. The face of the girl I picked was blurred for her privacy, but I had the rest of the description memorized.  5'3", 115lbs, 22 years old, shoulder-length brown hair, nice little body.  The hotel was one of those that needs a key-card for the elevator, so the booker told me she'd come down to get me and she knew what I was wearing.  

Have had several episodes of being in the middle of some fun and then knocks on the door - "Housekeeping"
despite the sign on the door. Really?

especially when there are two of the same brand of hotel in a city.

An SB that was coming to my hotel room just heard in her head a different hotel name.  Went to the hotel, knocked on the room door ... the guy who answered didn't know who she was.  She double checks here text message, oops.  Texts me she'll be a little late.  Sends me a tracking app, and I watch on the little map as her car drives from remote hotel to my hotel... very accurate map because I can see her car out the window coming down the street just like is displays on the app.  She comes up, we laugh at the mix up.  I wonder what the guy at the other room though?  She was good looking.  Bet he wished she'd stayed.

your "adventure"!

20 min 3some w provider and gorgeous waitress/women's bathroom-Sofitel Chicago...provider handjob orgasm-the Lobby bar/St Paul Hotel...rather vocal 1am/multiple session-top floor balcony-Ritz-Lisbon Portugal....full moon-warm sultry night

I was going up the elevator to meet an escort and an escort I had seen before got into the elevator too, heading back up to her room.   We recognized each other and nodded, but didn't say anything because there were other people in the elevator, too.  

At the time I used to own a home near Fountain Valley, Ca.      One day I was heading to the local Walmart, Flat screen TV shopping.     As I was walking to checkout, I looked in the next Isle, and there,   In a (barely there) mini-skirt was one of my ATF Thai dates.     She didn't notice me, thank god.   I quickly headed back towards the electronic section until the coast was clear.    Ironically, after I finished bolting my flat to the wall,  I called her and made an evening appt...LOL

It is very sexy to see escorts in their real life activity

I was in a hotel elevator, going up to my meet my provider.  As I walked from the train station (I use public transit to be discreet), my hair got messed up in the wind.  And the elevator had mirrors.  So I used the mirrors to fix my hair; totally normal, right?  Well... as the elevator rode upward, an older couple, like in their 60's, got on.  The husband saw me fixing my hair, looked me in the eye, and said "we caught you now!"  I chuckled, and didn't say anything back.  Then I got off at my floor, while they stayed on.  Did they figure me out, or was he just pulling my leg?  The world may never know...

Or he has been or currently  is in hobby himself.

you are doing something you're not proud of to jump to the worst case scenario first.  Hooker was probably the last on his list of possibilities resulting from your behavior.  If you're primping to meet a woman, I'm sure wife and girlfriend were the first two on his  list.  I had something like this happen to me where I was checking last minute in a mirror in the elevator to see how I looked, and just like you, a couple got on, and the guy said "You must have a hot date."  I said, "I do, its our anniversary."  As I got off at the next floor, he said, "Congratulations, have fun."  I think remaining silent when a stranger is trying to engage you in conversation makes you look guilty of SOMETHING.   It actually WAS an anniversary of sorts.  It was the second time I was seeing this provider.  Lol

Who primps for their WIFE??? lol

Although anniversary technically means yearly, in modern usage people prepend the unit, such as 6 month anniversary.  However this is still frowned upon by linguists.   One month celebrations have in the not too distant past been referred to as mensiversaries (from the same root as menses) but recently monthivesary or even weekiversary.

You're mostly right, and I realize he was joking, giving a Millennial a hard time just for fun.  Going with your ideas, he may have thought I was cheating on the aforementioned wife or girlfriend, if the "guilty" part was true.  (Plus, I was half his age.)  But also don't forget: I was younger back then (it was 5 years ago), so I still had traces of my youthful skittishness left in me.  Today, I would have looked him squarely in the eye, and joked back one way or another.