Here is a VERY long and extensive dive into my experience with menstrual cups, including all the tips and tricks I wish I could have gotten all in one place. I hope that this will help somebody! :)
Choosing a Cup | Cleaning Before Using | Insertion | Dealing With Residual Blood | When to Empty Cup | Peeing or Pooping with a Cup | Removing Your Cup | Cleaning Your Cup and Removing Stains
Choosing a Cup
When you are choosing a cup, it’s super helpful to take some quizzes to get an idea of which cup may work best for you. There’s one from Menstrual Cup Reviews and one from Put a Cup In It. You will want to measure how high your cervix is. This is something I didn’t put too much emphasis into when I first started and I wish I did because it would have saved me time and frustration (and trauma lol). My cervix is too high for me to reach, so I have a very high cervix. I originally thought I just didn’t know what I was doing or how to find it, so I just went with the assumption that I had an “average” height. If you have a low or a high cervix, this will cause a LOT of problems if your cup is not the right size for you. You will end up having to experiment with different cups to find something that will work for you.
The two websites I mentioned previously are totally golden resources to help you in your quest to find the right cup. I spent lots of time on there, comparing and researching about different cups and what would work better for me. Make sure you search around for any promo codes and discounts before purchasing a cup to save some money.
If at any point you are having trouble, there are Facebook groups (for example, the Put a Cup In It group) with lots of people who are happy to answer questions and offer advice! I would definitely recommend joining those groups.
Cleaning Your Cup Before Using
How to clean the cup before using it? Per instructions of most cups, boiling (a rolling boil for 5 min) is probably the best way to sanitize the cup. You may also choose to clean with mild soap (no scent, no anti-bacterial – to avoid yeast infections, etc) and water. There are also intimate washes that are supposed to be pH balanced that you can purchase. As an alternative, there are menstrual cup steamers available online as well.
I personally like to keep it simple with just boiling and soap. Make sure you wash your hands with a mild, non-scented soap as well.
Inserting the Cup
Next, the most important tip for cup insertion is to relax. Tensing up prevents anything from entering. You want to try it when you have all the time in the world and no pressure. Ease the cup in nice and slowly, while pushing your muscles slightly (as if you were going to pass gas haha) to allow the cup in. I highly recommend lube to help guide it in easily and painlessly. Water is better than nothing, but not as smooth as lube. If you do use lube, I recommend folding the cup first, then putting a little bit at the tip and maybe along any large bulges. If you lube up the entire cup, it may be too slippery and difficult to handle.
People commonly advise you to “angle it upwards back towards your tailbone.” Depending on the cup and your positioning, it may or may not work. Someone gave me the advice of inserting the cup horizontally to the floor, straight back to your butt, and that was what did the trick for me.
I prefer sitting on the toilet with legs wide open. Some people prefer standing with one foot propped up, squatting on the floor, sitting on the toilet with one foot propped up, or maybe even lying down. You’ll have to try different positions to see what works best for you.
Make sure you have a tight grip on the cup at all times (two hands may be necessary) because it is frustrating and uncomfortable to have the cup spring open too early. We call it the urethra or vagina slap. 
Try different folds to see what works for you. The most popular folds that tend to work are: the C-fold, punch-down fold, 7 or triangle fold, and double diamond fold. Whichever portion of the fold is supposed to open up, I would recommend pointing that down to the floor when inserting. Pointing it upwards runs the risk of the cup opening up prematurely and hitting you in the urethra (ouch). Also, the backside of your vagina is easier for the cup to open up because the frontside has your pubic bone in the way.
Speaking of the pubic bone, you want to make sure the cup is able to open past the pubic bone. So this may involve you pushing the cup further up to give it some room, and pulling it back down into place. Doing this with a twisting motion of the cup is also helpful in getting it to open. If you poke around at the base of the cup, you may feel the cup open up. You can try placing a finger inside and running it around the cup to see if there are any folds. Once you think it’s open and in place, do some kegels to make sure the cup is open. This video was extremely helpful for me!!!
I personally could not feel the cup opening up with a softer cup. With a medium firmness cup, I actually could feel it either suctioning or a slight uncomfortable pop inside of me. Sometimes it can open up during your maneuvering of the cup, and sometimes it could be a few minutes after when you’re already continuing on with your day. It’s not painful for me personally, but it is uncomfortable…the bright side is I know the cup is open for sure. 
If you cannot get your cup to open despite a ton of troubleshooting, you may need to get a firmer cup. The firmer the cup, the easier it is for it to pop open into place.
Dealing with Residual Blood
If you already have pads at home, I would recommend continuing to use it in conjunction with your cup while you’re first getting used to it. You want to catch any leaks and see how much (if any) you’re leaking so that you can figure out adjusting your cup properly. Remember that the cup will catch any new blood flow, but not blood that is already in your canal. So if you’ve already started bleeding and you inserted the cup afterwards, you may have residual blood that leaks later on, which is normal. Or, if removal was messy while you were emptying your cup, there may be residual blood left in the canal when you re-insert the cup back in. One tip is to use a finger to swipe any residual blood in the vagina, rinse it under tap water, and repeat until clean. You could also just try wiping with a wet napkin, etc.
Once you’ve gotten the hang of it, you can choose to go free with bare, regular underwear, or you can choose to wear period underwear as a backup. I chose period underwear because you just never know if you’ll overflow or have a random leaking accident. It’s nice to have that peace of mind. I totally recommend Bambody period underwear. They have a leakproof pair that’s great for lighter days, and a more absorbent one for heavier days. I have both and love not having to ruin underwear or wear backup liners anymore! I highly recommend sizing up by 1 size if you want to be comfortable as they are pretty tight around the leg holes. If you prefer a snug fit for more security against leakage, you may want to stick with your usual size.
When to Empty the Cup
The cup is supposed to be safe to use for up to 12 hours, but when you need to empty is dependent on the individual. I have an extremely heavy flow, so I had to use a higher capacity cup and even then still empty it in about 5 hours during my heaviest time. Interestingly, I started feeling a strange “bubbling” feeling down there before I started leaking a bit and I knew I had to empty my cup. Later into my cycle, I would get lighter and only need to empty every 10-12 hours.
Most cup manufacturers recommend removing at least every 12 hours regardless of your flow so that you can clean the cup and reduce the risk for infection. The risk for toxic shock syndrome is lower with a cup than a tampon but that doesn’t mean the risk has been eliminated; it’s still there. So don’t let your cup brew in there for too long!
Peeing or Pooping With Your Cup
Can you pee or poop with a menstrual cup inside of you? The short answer is yes! However, some people may have trouble with it. The good news is you can troubleshoot to solve this problem.
If it feels like you have to urinate all the time despite not actually having to go, that means the cup may be pushing along the bladder or urethra. Others may find their urine flow is weaker/slower or they can’t push urine out at all when wearing the cup. Try repositioning the cup higher or lower and see if that helps. If that does not help, the cup may be too firm. You’ll want to consult with a menstrual cup chart and choose a new cup that is less firm.
Likewise with bowel movements, if you feel like you cannot easily poop with the cup in, you’ll want to take it out and put it back in after. Some people find that pooping actually pushes their cup out (it’s the same muscle movement that helps us remove the cup after all) and they will also need to remove their cup during bowel movements.
Removing Your Cup
All right, home stretch! Now for removal tips! Squatting on the floor with your heels pressed down, frogger style seems to be the best way to naturally position your cup closer towards your vaginal opening. I think that’s the best way to start out learning how to remove the cup.
After I got the hang of it, I started getting used to removing with my legs spread wide on the toilet because 1) no mess to clean up if there’s spillage over the toilet and 2) being able to remove on the toilet means I’ll be able to do removal in public bathrooms. Our American bathroom stalls are terrible since the doors are not flush against the walls, leaving large cracks people can see through, and the walls/doors do not come down all the way to the floor…meaning if you were to squat in a public bathroom to remove your cup, everyone else would see all your goods as well lol.
I learned that the best way to remove a cup is to bear down (which is using the same muscles to push as if you were pooping or passing silent but deadly farts ;)), while keeping your mouth and throat open (like when you’re blowing hot air out of your mouth onto a window to fog it up). Supposedly that relieves the pressure so that it protects your pelvic floor when removing a cup that has a tight seal. I personally need to wiggle the bottom of the cup (with the grip rings) side to side and down until I can reach a little farther up the cup. Then I pinch the cup between my thumb and index finger firmly (Don’t be scared; I was too gentle at first until I realized I needed more force), continue wiggling side to side, until the suction is released (I can hear air entering the cup and squishing noises if the cup is particularly full; it’s a funny sound), and I can gently & slowly pull the cup out.
Do not pull that sucker straight out without breaking the seal of the cup. It will feel painful and uncomfortable.
I like to press my thumb into the cup as I’m removing to create a dent and fold the cup into itself right before I pull it out, so that I protect my urethra and so that the cup is more comfortable to remove. It won’t feel great pulling out your cup in its fully opened form, especially if it’s a larger or firmer cup.
I find that if I’m having trouble reaching my fingers farther inside for a better grip (it feels like my fingers are too short), it’s really helpful to lean my torso down and forward as if I’m going to hug my knees.
Some people cannot reach very far in with their thumb and index finger; you may find success with inserting your index and middle finger along each side of the cup (like chopsticks in a V shape) and then pinching the cup that way.
It can be scary at first because most of us are not used to reaching inside the vagina to grab anything. You do need to learn how to be comfortable with getting extremely familiar with your anatomy. Although it can be scary, it’s your own body and you can do it if you have the willpower!
Do not panic if removal is not going well. There is a learning curve. Do something else to relax, and come back later to try again. The cup can have a pretty tight seal (which is great against leaks!) and this may make you extremely frustrated at first, but just know that once you find the right technique, the removal process will be a lot faster and easier.
Also take note that overnight the cup may ride up higher and be hard to remove first thing in the morning. You may want to do your morning routine first or walk around before going in to remove.
Since I know that (beyond reading about it) hearing it and seeing it is super helpful as well, here is a great video on removal. This one is another good video, as well as this video and this video. :)
When emptying the cup, I place 2 pieces of toilet paper into the toilet and dump the contents out on top of that. That was another great tip I learned because blood is denser than water and if you dump it straight into the toilet, it will quickly sink down and possibly leave blood streaks/reside after you flush.
It’s actually pretty neat to see if you aren’t completely squeamish. Strangely enough I think it looks less gross than removing a soaked pad or tampon. I guess because I can just cleanly rinse it off completely with water rather than wrapping it up in a ton of toilet paper and hiding a huge wad in the trashcan.
Cleaning Your Cup (Again) and Removing Stains
Remember to rinse your cup with COLD water first! Hot water sets in any blood stains so you want to use cold water instead. I use my fingers to rub the cup and clean under cold water and re-insert. If your cup has little holes for suction, the easiest way to clean it out is to fill the cup up with water, quickly turn it upside down into the palm of your hand, and squeeze out the water (gently). It will force water out of those holes. I say gently because if you do it too hard you may shoot yourself in the face with bloody water.
If you are in a public bathroom with no private sink, you’ll want to just reinsert without rinsing the cup and clean the cup later when convenient. Otherwise, you could bring a small cup of water or water bottle into the bathroom with you to rinse the cup. I bought a cute little collapsible silicone cup to help rinse in public settings (also a great container to do a peroxide or vinegar soak too).
If you no longer need to re-insert and are done with using your cup for this cycle, I would recommend washing it with mild soap and water, and then do a rolling boil for 5 min to sanitize. Let it air dry and store (the cup usually comes with a little pouch for storage).
If you notice a bit of staining on the cup that you’d like to remove, you could try doing a hydrogen peroxide soak or a vinegar soak with half solution and half water overnight.
Do not store the cup in something airtight because that will encourage bacterial growth. I would simply boil again right before using it during the next cycle.
You’ve Got This!
Good luck! It took me several cycles to finally figure it all out. It may be an overwhelming (scary and exciting!) process at first but it is totally worth it when you can successfully reap the benefits! :)
And for some cup-related fun, here are some hilarious comics by Miss C!
Other related posts in my menstrual cup series: Menstrual Cup Reviews (Saalt, Peachlife, Lily Cup, Ultucup), My First Dive Into Menstrual Cups, 20 Reasons I Love My Menstrual Cup
