it may be because i have long arms, but i can easily use my dildo in my right hand and my vibrator in my left. i've yet to try the ole pillow trick with my dildo but im going to!

no not even one can go in

I'm a guy, so generally if I'm using two toys my ass holds one for me while I masturbate (example: a vibrating plug and my fleshlight)


I could see how this poses issues for thrusting in both holes or using more than two toys though.

I understand your point here, my most important thing with toys is for them to be as little effort as possible on my part so I can just enjoy the ride as much as possible. I've found a couple of toys that are compatible with others for example:
The Lelo Tiani 2 or Jopen 6.5 where you can also use a glass dildo or eggs. Both stay in place once in position allowing at least a second toy. I usually go with the glass eggs and the Ultra Heat or Chill for internal sensation.

That leaves my hands free so why not add a couple of nipple clamps of your preference, a face mask and some erotic massage oil to run your hands smoothly over your body. Or why not yet another vibe or two, the smaller ones, one in each hand to caress other erotic zones.

Two hands, two toys. Usually a vibe and dildo. Get something easy to hold with one hand. Anything more can get really awkward. But usually I just use one toy at a time and have an area on the side for the others.

I have used two before I just use one with each hand

I only use one most times and if I just two its something hands free

If I'm using both it's usually dildo in my left hand, vibrator in my right. Seems to work okay for me!

If I'm using both it's usually dildo in my left hand, vibrator in my right. Seems to work okay for me!

I do sometimes. If I do, I prefer to be on my back, or on my knees.

I usually use two.
It gets exceptionally tricky when you need to use three at the same time though (clit toy + dildo + wand against dildo) lmao..

Masturbation will be a competitive sport at the 2020 Olympics at Tokyo. Multiple toy dexterity will be carefully judged. Points will be award for most orgasms, sensual moans. and loudest screams. The 100 second dash to gasm will be highly competitive with the fastest cummers in the world competing for gold. Of course course, the pentabation event featuring 10 masturbation events will be the crowning event.

It can be a little awkward at times, but I can usually make it work. Also, some of my toys are of the "get it situated and then leave it be" variety that don't require me to move them or even hold them. Various nipple toys in my collection (clamps, suckers, ticklers with suction cups, etc.) stay in place quite well once I get them attached. Also, I love a good, strong vibrating egg to use vaginally, because I can just shove it up my twat and it'll stay there until I decide to remove it, which frees up my hands for other things. Butt plugs and other "wearable" toys are also good in that regard.

I can and do use old-fashioned unpowered dildos paired with clit vibes. I typically maneuver and thrust the dildo with my right (dominant) hand, and then just hold the vibe stationary on my clit with my left hand. That's probably the most awkward/difficult toy pairing for me, but I've found that like most things, it's gotten a lot easier with practice. If your dildo has a suction cup, another option would be to attach the dildo to a surface and either ride it or back into it while using a toy on your clit. That would free up a hand and make it easier to maneuver the clit toy while still getting to enjoy your favourite dildo. (I can't really do this since I don't have a good place to attach a suction cup dildo, but it's a great option for those who can make the logistics work in their living situation.)

Another option that I've only recently started exploring myself is attaching a vibrating cock ring to a dildo. This gives you that blissful dual stimulation without the awkwardness of trying to maneuver two toys at once. Depending on the specific dildo and cock ring in question, it can sometimes be a little annoying to get the cock ring on and off the dildo, but liberally lubing up both toys helps a lot with that. Also, if you like to use really girthy dildos, it might be tricky to find rings that fit, since most cock rings are designed to fit actual human penises, not over-sized toys. But I only use small-to-medium sized dildos, so that hasn't been an issue for me, and I've really been enjoying trying out various ring/dildo combinations.

These days, always! But you're right, it is quite tricky to manage them depending on what you're doing.
I typically go for a G-spot vibrator of some sort, which will stay in pretty well if I am lying on my back. With strong enough vibrations, I don't need the toy to be moving; my hands are free for a C-spot stimulator, and I use the combined vibrations to get off.
If you do need to actually fuck yourself on something and still want to use another toy, try suction cups! You may even want to buy a good strong suction cup from another store that you can rig to a dildo/vibrator since (in my experience) the suction cups on most toys don't work when the toy is actually in use.
You can also rig up ways to keep toys in or on you: a homemade harness using rope/fabric (which is actually pretty common, from what I've seen, for holding wand vibrators in place; a conveniently placed pillow or other objects to prevent a toy from sliding out; etc.
It is possible to use one toy with each hand but personally, I end up focusing too much on trying to optimize the sensations with each and don't end up enjoying it XD So I'd having at least one toy that can be kept stationary and/or doesn't require hands at all is the best.