F / starting with messy/insertions.
 

How about you use one of the vegetables that you have used before but this time use toothpaste as lube

I can try that, but i guess i not gonna like it that much :o

Got this one in pm and just did this one.
Got 8 grapes in think if i put more in a would already crush some (but might try it later again)
with the vib on my clit felt so good and had to focus to not squeesing it all.
To bad one grape bursted a bit when i got them all out.
and then i ate them ofcourse.

stuff your pussy with raspberries, blackberries, straberries, plums and cherry tomato. put clamps on nipples.
lay vibrator flat and sit on it wit your pussy. adjust speed to slow vibation.
after you cum you can eat it all.

haha you make a nice fruity mix of it
lucky me i like healthy

How about inserting some milk into your pussy through a funnel or candy like jelly beans.
Maybe fuck yourself with a baby cucumber and put it all inside of your pussy and then take it out and eat it or put it in a salad ( everything has to have been in your pussy atleast once.)

I put it on my list to try ;)

Let's go for messier. And because it's around holidays, less healthy.
Sugars are a risk, but it seems to be a risk you are willing to take, so I'll jump right in.

Get a donut or cupcake. A jelly or creme filled kind. The filling is your choice. Choose the messiest, and the one you like the most.

Put the chosen item down your panties, and then find something you can straddle and grind on. Hump your pussy against it as hard as you can, while crushing the donut/cupcake. If you can hump things to edge, do that.

Now, you have two options. You can either end there (in which case, you take off your panties, admire the mess, and eat all you can out of your panties, off your body, and out of what got pushed into your pussy, before clean up), or you go for an extreme finish.

If you want the extreme finish, get a dildo or insertion toy of your choice, and sit down. In front of a mirror is fun, because you can see the mess!
Slip your panties off, and use your hands to scrape all the mess on your body to your hole, before using your fingers to carefully push the crushed, ruined cake, frosting, and filling, into your pussy.
Then scoop all the remains you can out of your panties, and similarly stuff it into your pussy. Again, fun of being able to watch nonwithstanding? The mirror will help here, a lot!

Line up your dildo, and fuck yourself hard to orgasm, as it pushes the food deeper, crushes it, and mixes it with your own wetness.

When you're done, you have the task of getting it all out of you, and eating it. Using an old, sterile douche, filled with milk, should be a good way to flush it all out, and milk goes well with cake, so the end results should still taste great.

That's.... probably one of my most extreme tasks. But, near as I can tell, it doesn't violate any limits, and falls in line with what you asked for.

Well, you did say "starting," so it might be extreme to just jump in with. If you can't really do it... no harm. I'm pleased the idea at least excites you, and I hope you enjoy it, even if you feel you'd rather not go entirely crazy.

I look forward to hearing how it goes!

Gladly we have a nice big bathtub were you can lay in.
So took a big glas of milk a bowl to leak in and a little bag of gummibears.
First played a bit with myself to get a bit wet before i putted the funnel in my pussy, its not so big but big enouth that the gummibear wout fit through it.
Laying not really comfortable but yeah like almost complete upside down i managed to poor the glass of milk in the funnel.
And felt it gushing inside me pretty weird feeling, I also putted 4 gummibears into it.
When the funnel was emty i slowly removed it and moved slowly back to a normal position holding my pussy closed with one hand.
I had also a carrot to fuck myself with. I squatted above the bowl so it would leak into that and easyer to drink after.
putting the carrot into it all felt good tho, the milk leaked out a bit so i kept going on till the whole glass was leaked out.
only the gummibears were left in so i got the out with my fingers and ate them. I continued masturbating with the carrot till i reached orgasm. And after that i drunk the bowl with milk and took a shower.

Here are a couple
Everyone loves to know that got someones cherry so how many cherries can you fit cum by vibbing your clit

Since it is the holidays perhaps a tangerine or orange

And then there is always the naughty elf that uses the candy canes to masturbate with

Some prunes, medium/small size, carefully washed (better if using some sort of eatable disinfectant, health is the main matter).

Strip naked, sit on a chair, put a prune on the seat against your pussy and try to make it slide in just sitting on it (once your labia will be against the seat with the prune buried between them, you can push it completely inside with your fingers). Do it again with as many prunes you'll be able. When you'l be pretty filled, dress wearing sheer pantyhose and skirt and go out for a walk or some shopping (one hour at least).

Once back home, strip naked except for pantyhose, go in front of a mirror, spread your legs and make yourself orgasm rubbing your clit through pantyhose. Immediately after you had your orgasm, one by one, try to push out the prunes in your pantyhose only contracting your pelvic muscles and eat each of them before pushing out the following one. If you can't push out all of them, pull them out with your fingers and let them dry, you'll eat when your juices on them will be perfectly dry.