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Agh! I should refrain from posting double posts in a row, but as this community has such helpful users, I felt the need to really explain my problems since I'm apparently having (too?) much trouble with this than I should. 
First of all, thank you for the recommendations on my last post! I tested some out today (since I'm on my period right now). 
Anyway -- I'm still having a hard time inserting, and I'll go into detail here. I tried multiple folds and the results were all the same, so it's most likely ME, not the folding method, which is rather unfortunate. 

The last one I used was the 7-fold. I for some reason have a difficult time holding on to it (I'm a virgin; and I'm using a small Lunette Selene; for anyone who didn't read my last post) but I can manage. I was inserting it normally (although I may have been pointing the cup a little too to the left since I'm right-handed) and I could only go so far as to... maybe the base? I'm not sure if I even went in THAT far. It may have been halfway, even. -- By the way, I was doing this in the shower, and I can't buy lubricant as I'm very young, so water was my best option. -- So once I got to that point it felt like so much pain. It wasn't a particular type such as burning or stinging, but it was as if I was it was putting pressure on my vagina and it just hurt like crazy. I'm extremely fed up with pads, so I forced myself to push it in further [because I want to use my Lunette so badly] but I couldn't do it anymore, it was too painful. The whole "insertion" took around ten minutes or so. So ONCE AGAIN, for just about the sixth time today, I removed it without it hardly going in in the first place. 

Then I thought, "there's no way I can just stop there..." so I tested it out, and put my middle finger inside of me, and I got so far that I couldn't even feel my finger inside of me -- and I did it all in about 15 seconds. 
So why can I go so far with my finger, but not with my cup?! Grrr, I feel like I'm hopeless with this thing. How is it possible that the cup is causing me so much pain when I hardly put it in, yet something as long as my finger can go in so easily? 
I have a pretty high cervix, by the way. I don't think I've ever reached it, even on my heaviest days. So what am I doing wrong? 

Serpentserpent_849 on June 14th, 2012 07:16 pm (UTC)
are you relaxed? keep your jaw slack and relax your shoulders.
speaking of the folds, have you tried labia? that's what i prefer with my small lunette.
also, are you sure the angle was correct? it's kinda easier with a finger. at first i had to look to be sure i'm inserting correctly :DDD you should point it towards your tailbone/butthole.
arcticfox97arcticfox97 on June 14th, 2012 07:25 pm (UTC)
At first I'm relaxed, but I do notice a lot of tension throughout my body since I'm afraid of it hurting before I let go of it or something like that happens. :( Thanks!
I haven't tried the labial fold, but I've looked at some videos on it and it looks sort of intricate. I'll have to check it out in a few minutes again!
Hmm... the way I do it is just like a tampon. I make it go in straight for a little, and the I slowly go more and more upward, it's a little like this slash: /
Is that incorrect? I don't go *that* much curved up, but it is at an angle upward.

Edited at 2012-06-14 07:27 pm (UTC)
Serpent: neutralserpent_849 on June 14th, 2012 08:18 pm (UTC)
I've heard it's different from tampons. I myself aimed up on my first dry run and failed completely and suddenly remembered what I had read :) Try again!
arcticfox97arcticfox97 on June 14th, 2012 08:53 pm (UTC)
Oh -- really? Thanks for letting me know! I'll try aiming it the way you mentioned the next time I try.
The good news is that a few minutes ago I finally made it to the bottom of the base. The bad news is that it started really hurting up to that point so I had to take it out again, haha. But I did try a different position and I was REALLY trying to take my mind off of inserting it, which I think helped a lot. Thank you!
juliiie87juliiie87 on June 15th, 2012 12:50 pm (UTC)
Give your body a rest if you're in pain, there's no shame in that. Since you're a virgin, I will guess you probably don't have much experience with this part of your body, so you still need to get comfortable with it maybe, so really don't feel bad if this takes you some time. You're doing great already !

I totally support aiming horizontally towards your butthole, and especially, that you need to RELAX ! Easier said then done, I know. In order to help you do that, I find that sitting on the toilet, knees apart wide or even better, lying on your back, resting on your elbow, in a "birthing position" works SO MUCH better. Litterally when I'm lying on my back, it feels like my vagina just drops open (like a jaw LOL). Another trick, is to bear down a little, like you were trying to pee / have a bowel movement, but not quite as much. You can practice this with a clean finger, learn to give it a squeeze, then on the contrary, bearing down, which creates more room in there. The reason I'm getting into such details is because I believe the pain you're experiencing is from involuntarily clenching your muscles down there, like your body saying "nope, you're not getting in!" but fortunately it's something you can learn to take control of. You will need to use this skill for removal also, especially if your cup rides way up.

And for lubrication... if you can't get access to lube (they're in every supermarket or pharmacy), try spit, water, and... menstrual blood. It's true, tampons dry you out, maybe use a pad on the days you're determined to try your cup ? it can be next period, also, if you're fed up with it, or on a rather "moist" day off your period.

Sorry for being so wordy, and good luck !!

Edited at 2012-06-15 12:58 pm (UTC)
teacupcake89 on June 15th, 2012 03:12 pm (UTC)
this :)
arcticfox97arcticfox97 on June 15th, 2012 03:17 pm (UTC)
Thanks! I did try to do it again last night, but figured I should wait until the next day. I was just too tired out to try it again yesterday. :(
I'll try aiming it towards my rear -- thanks for that, too!
Ah, I think I do know how to bear down, then! I started getting the hang of it last year when I did it accidentally, but I didn't know it controlled those muscles, haha!
Do you really think it's just the muscles that's keeping me from doing it? Agh, I sure hope so, 'cause that's a lot easier to deal with in the long run!
I appreciate all the information a ton! I'll definitely take it in and consider it all the next time I try for insertion.
juliiie87juliiie87 on June 15th, 2012 03:29 pm (UTC)
Yep, besides the "vagina sticking to the cup" thing, which should be eased with any kind of lubrication, it's most likely the muscles, and perhaps the way you're aiming it as well ? I mean, it could be that some part of your hymen gets in the way, but that's unlikely, hymens are overrated, few people have them, and tensing up is much more likely to cause pain, like when someone his having sex the first time (or any time, really !).
rawlicious on June 14th, 2012 08:13 pm (UTC)
insertion requires: relaxation, lubrication and the right angles

relaxing each time you attempt to insert is important. do the jaw slaw and relaxed shoulders like serpent_849 suggests.

the positioning of the folded part of the cup might make a difference for you. like if you have the punch down fold and the folded part is facing down to the floor, or up to the ceiling, or left or right, etc. try all different ways

definitely point it more towards your tailbone. if you can figure out the angle with your finger, try to remember that and use that as your guide to angle the cup in.

maybe try to do it when you are sitting on the toilet or lying on a bed? i tried in the shower and it didn't work for me, even though a lot of other people on here swear by it.

even if you are young, that doesn't mean you can't buy lubrication. you can even get it online most places you can buy a menstrual cup. i can't get my cup in without it. i find the silicone of the cup just kind of sticks to my skin painfully if i don't put lube on the cup. even if you are embarrassed to buy lube at a store, you can still do it. just go in, find a water based lube and get out as fast as you want. you just need to know it's not an embarrassing thing to do. some people even need to use lube to get a tampon in. bite the bullet and do it, i can't express how much lube helps me with my cup.
arcticfox97arcticfox97 on June 14th, 2012 08:59 pm (UTC)
I didn't know much about positioning the folded part -- so thanks for that!
I definitely do try to do it the same way as I do with my finger; it's just super odd that it hurts only with a cup when the path is almost identical.
I found that sitting on the toilet doesn't work too well... laying down makes me more relaxed, although it's pretty hard to go all the way back AND reach to insert it... urgh. So far I made the most progress with the way I insert a tampon -- against a wall and a leg up on the counter.

I think the cup sticks to my skin as well. :( At the moment where I am I can't access many stores -- do you know of any alternatives to lubrication? Like substances you can find in your house (oils, mixes, etc.)? Thanks!
Serpent: neutralserpent_849 on June 14th, 2012 10:20 pm (UTC)
oil is a bad idea. you could try spit.
also tampons dry you out, so inserting a cup right after removing a tampon might be more difficult.
rawlicious on June 14th, 2012 10:58 pm (UTC)
http://www.ladycup.eu/Orderonline/tabid/58/ProductID/6/Default.aspx here's a link to buy lube online. it's the ladycup website, but i'm sure other cup websites have them too. i ordered my cup from this site, it's safe. just one option for you.

otherwise, just water i guess...

definitely check out the virgin guide to cups!
loveyourcuploveyourcup on June 15th, 2012 11:29 am (UTC)
Any waterbased lubricant will do. I usually just wet my cup with water, i never put it just dry.

Edited at 2012-06-16 10:46 pm (UTC)
nocebo_domingonocebo_domingo on June 14th, 2012 10:25 pm (UTC)
You mention that you're a virgin in your other post. Maybe you are bumping into your hymen with your cup, while your finger is narrow enough to fit through easily. There is a virgin's guide to cups and several community members learned to use cups as virgins. Maybe one of those people can provide suggestions?
teacupcake89 on June 15th, 2012 03:02 pm (UTC)
you've got loads of really good advice here already!
(I have been known to write down/print off advice so I could have it next to me when trying to insert/remove! :)

Lube: apparently coconut oil makes a good lube and you can use it as a body moisturiser! :) lots of spit is another option. is asking your mum etc an option (if knows about the cup) ?

not sure if this helps location-wise but...: I buy KY jelly lube online from Boots and either get it delivered home or to my local store branch, it comes already boxed up so the person giving you the box and anyone in the shop won't be able to see what you've bought! :)

definitely aim 'down' at a diagonal towards the end of your bottom!

when you start feeling nervous/tense: pause, take a few deep breaths, try to relax every muscle and then try again/or take a break :)

Edited at 2012-06-15 03:08 pm (UTC)
arcticfox97arcticfox97 on June 15th, 2012 03:22 pm (UTC)
Thank you very much!
Ooh yeah, I've heard lots about KY Jelly. Just don't know if I'd be completely comfortable buying it since my parents are always wanting to be extremely involved in what I buy in-store or online. I do have coconut oil, though, so I'll read up more on that -- thanks!
Hehe, I'm glad so many people are suggesting to aim more downwards; I'm hoping it'll be a bit better if I try aiming it that way and not so much upwards. Although relaxing can be a little difficult when the whole process is involving a really sensitive part of your body. :(
teacupcake89 on June 15th, 2012 03:11 pm (UTC)
p.s. this should be the link to 'The Virgin's Guide to Cups' http://menstrual-cups.livejournal.com/1243131.html#comments

really helpful for all cup users with insertion and removal whether a virgin or not :) good luck!