As the title says, what's the most fun you've had getting messy? I'm not necessarily talking about the hottest/most erotic time (though the two are by no means mutually exclusive), but the most joyful, invigorating, fun occasion.

(For me I think it's still the very first time I got messy with my wife - there was a point where we were both completely covered and it descended into the kind of playful, tit-for-tat silliness that I absolutely love)

Me, my wife, several buckets of gunge and some waterproof toys. Hours of fun

Nearly 15 years ago (which feels longer as you get older) me and one of my female friends made a bet on the Super Bowl. She lost the bet and my friend agreed to do a shaving cream pie session at a smaller hotel near Atlantic City. She was plus size but very beautiful and I pied her very well and she returned the favor to me. We had a fun time together and she took the pies like she had been pied for years. Sorry, no pics of the session cause it was a private session.

Spendin' 5 days at a 'Grunge-Guys' event..... Just a bunch of hot guys, gettin' 'wet', 'muddy', 'messy', and other 'things'.....

Most of my pie sessions have been fun, but I'm easily pleased when it comes to a session. Just sit me in a chair and rub a few pies in my face and that suits me just fine.
Saying that, my first ever session was very well set up and I did enjoy experiencing all different types of pies and gunge throughout, so I learnt what kind of gunge I liked and didn't like (wasn't much of the latter). Not to mention the guy who got me made me feel very at ease, as I was quite nervous. He didn't pressure me, let me do everything at my own pace and, by the end of it, I was totally trashed but I absolutely loved it. So that was probably the most fun and the most memorable for me

Sometime in the late aughts (2008-2010?), I met up with a guy who was in town for business and staying at a hotel a little south of the city where I was living then.

He asked about being put through an series of fun-ishment type dares/tasks. We agreed from the beginning that we both really wanted the evening to be fun for both of us, so to give him a little extra motivation to complete all of his tasks, I included some potential payback as motivation. For each task he completed (there was something like eight or ten or twelve of them), he got to give me ten swats with a vintage frat paddle...and, to make a long story short, he completed EVERY task I gave him.

The first few rounds with the paddle were on my jeans, then on my boxers, then bare-ass, and finally bare-ass naked. There were also a couple of cumulative payback rewards built into the session based on how many of the tasks he completed (and, since he completed all of the tasks, he got all of those paybacks). One of them was getting to shave my pubes. And another - for completing ALL of the tasks - was getting to gunge/ trash me, which only seemed fair, since one of his dares/tasks was letting me trash him.

He took his time, drizzling and pouring about a dozen different substances all over me (and then rubbing the resultant mess all over me, so that basically every last inch of me was covered in the collective mess). After asking permission, he even edged me for a few minutes, using the mess as lube.

Did we do anything more than jack off? No. Was it the messiest I've ever been? No. Was it the most fun I've ever had in a messy session? Absolutely - because both of us were completely at ease with one another throughout the entire evening. (I didn't even feel self-conscious being naked in front of him.)

With a mate in full body wetsuits pumping custard into each other's, feeling the full coverage inside, leaking out around the edges leading to full coverage on the outside too, making out with him in, unzipping the top halves and feeling the skin-to-skin slime then adding more liquid lubrication lying in a big puddle of sweet slime entwined together. Bliss!

I always enjoy getting wet, but the most fun I've had is when I've tried messy! Rice pudding, custard, milk drink, squirty cream and best of all, oil!
There's an extra thrill getting messy!
Only drawback is the clean up afterwards!
Peter

I used to go to a local mud volleyball tournament. Just a couple thousand people hanging out in the mud all day was always fun. It wasn't watery mud, it was thick gooey and shin deep. incredible to hang and get in mud fights that I couldn't win.

Most of my fun has been masturbating because I usually find sessions underwhelming. Much better in theory where are no logistics or cleanup on the mind.

The most fun has been being dressed up, tied up and then messed up.

This

I've been lucky to be able to live out many of my fantasies on video. All of therm were spectacular. Recently I had some time and when you have time........Then came the mulling.....do I? Then came the planning......the anticipation builds.........then came the set up........yes, you're doing this........the prep.....do I have enough shaving cream?...........pre-execution pondering.......then execution! It was so exicting, I'm still buzzing from it.

My most fun was trip to usa to see darla and fun we had 1st time wont forget and see 3 girls got messy as well

Also doing a to z won't forgot as good fun . Most messy ever done

Going out to eat with my female friend Nicole.
She fitted me with a vibrating butt plug which she had total control over and she also filled my PVC underpants with real Cream Pies in the bathroom of the restaurant before we sat down in a wonderful burgundy vinyl booth.
I was wearing a black PVC suit and tie and hat and white PVC shirt, that she loved and called my chauffeur outfit.
She was wearing black patent leather doc martens with a red PVC dress and a pink PVC raincoat that she borrowed from me.
There was also yellow rubber dishwashing gloves in the pocket of the pink PVC raincoat that she used later in this story.
We were seated in a booth and the cream pies she put in my underpants we're driving me crazy.
She ate a salad and I sat across from her sipping on a beer.
People in the restaurant were looking at us because of our outfits.
When she was done eating she ordered a coconut cream cake which the waitress brought to the table in a box.
She took it out of the box and placed it directly in front of me and turned on my vibrating butt plug.
She took the empty box back to the waitress and I can see them both talking and then the waitress made a "O" face and put her hand to her mouth and started laughing.
Nicole came back to the table with a coconut cream pie and set it down so she could put on the yellow rubber dishwashing gloves in the pocket of the pink PVC raincoat she was wearing.
At that point my mind was racing a million miles a minute and I was so hard and turned on.
Nicole turned my vibrating butt plug up all the way and stuck her pinky finger in my ear laughing at me before she shoved my face into the cake.
She was getting off and enjoying the rubbing my face into the cake.
She pulled my hair, lifting my head out of the cake and took my pvc hat off of my head and laid it on the table.
She blasted me in the face with the coconut cream pie and smeared it all down the front of my black PVC suit and into my lap.
At this point people were laughing and in shock at what was going on.
Nicole started heaping unspent hate cake into my pvc hat and then smooshed it back on to my head twisting it back and forth.
Then she said that she was done and left me sitting there as she walked out the door.
The waitress came to the table to collect the bill and she had another coconut cream pie, which she smashed into my face and rubbed all over my chest into my lap saying that my friend wanted another coconut cream pie to go.... And by to go she meant.... To go in your face.
I had to stand up with everyone laughing at me and dig my check card out of the pocket of my pvc coat.
I had to stand there completely humiliated while the waitress ran the card and brought back the paperwork upon which I put zero tip.... But tipped the waitress with a $20 bill in cash.
The waitress was super happy about that.
I had to walk to the door and down a hallway to go out to the parking lot where Nicole's car was parked.
As I went out the door to the parking lot I could feel her playing with the vibrations and speed on my butt plug.
She was leaned up against her car smoking a cigarette and laughing at me.
There's more to the story but I'm stopping here because that is the most fun that I have ever had being humiliated in public.

I always wanted to grab one of your videos I'm sorry I didn't.

The messy session I had with my former Dominatrix. Most fun indeed. Introduced her to WAM and now she offers it to her clients now.

So many sessions have been fun that it is hard to pick one. Sometimes the simple ones have been most fun.

My best time was long ago, had a female friend and 2 of her friends we had a big naked piefight, had about 25 shaving cream pies, we all had fun doing it, that was the most fun I've had

For was at a prom dance and used water bottles an myself and the girl I was dancing with

Thanks for all the great replies!