I Lost My Period Cup Virginity

Seven-ish years ago, my friend Kassi was over at my house hanging out, making food, drinking red wine — I remember it well. We were in my kitchen and she was talking to me about her Diva Cup while chopping tomatoes for homemade bruschetta. She told me how amazing and life changing it was for her, how easy it is to use and how natural it felt, how good it was for the environment — she was trying to convince me to join her period cup cult. This was the first I had heard of such a thing. A silicone cup that you stick up into your vagina that catches the blood in lieu of tampons? Come again? What the fuck? I was standing there watching her as she was nonchalantly discussing while dicing and I can still feel the look on my face: it was an ugly mix of confusion and disgust rolled into one. Nope. No way. Gross. Not for me. My friend is a crunchy granola hippy. Damn this bruschetta is good. I passed slight judgment on my friend, the night went on, dinner was delicious, and I continued to push chemical laden tampons up my vagina for the next seven years.

Fast forward to the week before last. I couldn’t sleep and was scrolling through YouTube looking for something to numb my brain and help me drift off, usually a “What I Eat In A Day” (those fascinate me), when I came across a video on menstrual cups. For some reason I felt intrigued, that or I was hoping for boredom that would help fall asleep faster, and clicked play. The video was long. It was highly detailed. And by the end it was nearly 2 a.m. and I was searching Amazon for my soon-to-be new period cup. During my search I came across a familiar looking brand that I had most definitely seen slide across my desk at some point as part of a press mailing. Could it be? Did I already have a period cup in my possession? 2 a.m. or not, it was the perfect time to rummage through the press closet in search of the familiar branding, and to my surprise I found not one, but two (one for a light and one for heavy flow) period cups sitting at the back of a shelf smiling and waving at me. I spent the next hour examining my new silicone baby in all her glory, reading various reviews on the internet — this brand had great ones — and, going over the instructions. Never had I ever wanted my period to come so badly. Actually, no. That’s not true at all. There have been quite a few times that I’d hoped and prayed for my cycle to start after a wild night of unprotected sex, but you get the point. I couldn’t wait to try the period cup. I wanted to kiss tampons goodbye. I wanted to rid myself of chemical soaked cotton and help the environment and save a few bucks. Three days later, I started my period.

Now, everyone has a period story. Yours could be one of those that arrives on time like clockwork every month, lasts the same 4-5 days, and has minimal cramping, and ease. My period story, however, involves years of irregularity, horribly painful cramps, questionably long cycles, and very heavy bleeding. In other words, mine are hellacious. Regardless of how my body sheds its uterine lining, I was all studied up on the cup. I was ready. I had chosen the regular size cup which is suggested for medium to heavy menstruation or after childbirth, and I was really hoping for a seamless, less painful menstrual cycle as so many reviews have boasted post usage. I headed off to the bathroom with my freshly sanitized cup in hand to lose my period cup virginity. Praise be.

Before I jump into how losing said virginity went, let me tell you a little bit about the cup itself. It is made of medical grade silicone. It was a pretty ocean blue color. It is flexible and soft. It has a stem for removing it from the body and came with a little cotton pouch for storage and detailed instructions with different ways to insert, remove, and clean the product. It is supposed to offer protection for up to 12 hours. You can sleep with it in, workout with it in, and do just about anything and everything you would normally do with it in. Armed with all of the knowledge I could possibly absorb, I sat down on the toilet, folded the cup into the recommended C shape and inserted it. Upon examination and a strict following of the directions, I felt proud and confident that my cup was inserted correctly. I got up to go about my day. Within 20 minutes I felt wetness, returned to that bathroom and sure enough my cup had leaked. I tried removing the cup, which came along with a slight panic, but after a few attempts and forced relaxation, I was able to remove it, washed it, and went back into the bathroom for round two. This was the cycle for the next hour and a half. Insert, leak, remove, rinse, reinsert. What was I doing wrong? Was my vagina too big? Was my period too heavy? I texted a couple of friends, called my husband, and returned to the Internet to try and solve my problems. I was determined to make this work for me.

Over the course of my cycle, I kept my thoughts in a note on my phone to document my experience. Here they are:

In conclusion, I have to admit that I haven’t fully reached a conclusion yet. I want to love the cup. I love the idea of it. I feel like future me does love it, but I am just not quite there yet. I don’t want to discourage anyone from giving the cup a try when reading my first stab at transitioning. I think I just need a few more months on the saddle and I am pretty sure the cup I have is not the one for me. I took a Cup Quiz on a site called Put A Cup In It (brilliant!) and was matched with a few different cups that may fit my vagina and period needs better. I am going to order a couple different ones. I have high hopes. My fingers are crossed. I’m not giving up yet and will follow up with another more experienced cup review down the road. Last words: Thinx period panties were a jeans saver. I’ll be buying more.

What about you? Do you use a period cup? Did you go through a learning curve when you first started? Please share your experiences with me below. How long have you been using one? What have you found successful? How long did it take you to feel confident with usage?

Written by: James Kicinski-McCoy

James Kicinski-McCoy is the 40-something Founder and Editor-In-Chief of The Bleu. She likes tequila, picks fights with her husband so she can have the bed to herself, and is trying to figure out that work / life balance.


  1. Loa

    June 26, 2019 at 3:21 pm

    I tried and failed, and then reattempted after a good friend said” you must rotate it until it pops open and you can feel at base of cup that it’s open. Boom 🙌 never turned back.

  2. Jenny

    June 26, 2019 at 3:31 pm

    what she said^^

    the trick is not to immediately shove it deep in there. fold it, keep it pinch and folded at the top and slowly (while still pinching) insert until you are about halfway in. the little tip should be sticking out completely-let go of the pinch grip and you should hear a (yuck) suction sound.

    definitely don’t give up! try a different size etc, because once you get it, it’s fucking amazing. it makes traveling way easier, life easier.

  3. Tiana

    June 26, 2019 at 5:28 pm

    I know this may sound odd… [but because I am a nerd] i did half dozen or so “dry runs”. I tested inserting the cup and removing the cup when I was not on my period. what the two ladies said above me is true- once in place you have to make sure the cup has “blossomed” in order to do what it does best. So for me: fold it into itself like a bugle poorly shaped bugle chip- place it inside; then slide my fingers down to the little “tail” of the cup and pinch and slowly rotate left and right [I found this slow rotating motion helps the cup open up better/faster]. Also- for me- it was easiest to place the cup in the shower. i was able to squat.. lift a leg… it looked like i was doing the Haka. Removing the cup got a bit bloody [until I got the hang of it] and one time while relying on the “tail”-pulling to remove the cup the tail slipped out of my cramped fingers and i snapped the $#[email protected] out of my cervix. BUT… all this being said- the highs and the lows- the good, the bad and the bloody… I would never go back to tampons. Long live the cup! [wine glass emoji now has a new meaning in my life!] Hang in there and don’t give up.

  4. mamacita

    June 26, 2019 at 5:57 pm

    it’s nice to see you writing about your life again, even if it is about digging into your junk

  5. Courtney

    June 26, 2019 at 10:08 pm

    It took me probably 3 full cycles to really get the hang of it. I had problems with leaking too. What I realized was that the cup hadn’t fully opened like I thought it had. I had to spin it and sorta feel around the side to make sure it was fully open. Once I did that, leaking wasn’t a problem anymore. It’s an adjustment for sure but I truly would never go back.

  6. So

    June 27, 2019 at 10:48 am

    I tried and tried again for 6 months before getting it right, each leak felt exactly like the blonde twins scene in the Shining but now, after switching to the right cup for me and a 7 fold, it’s all goooood. So pleased!

  7. Madison

    July 3, 2019 at 3:27 pm

    This is so fascinating to me. I have yet to give it a try but when I’m looking for recommendations, I typically hop on over to Wirecutter and sure enough, they have some thoughts on the best menstrual cups. I might have to give it a try! https://thewirecutter.com/reviews/best-menstrual-cup/

  8. Anna

    July 5, 2019 at 1:02 pm

    The way you describe your period (irregularity + pain) sounds like you might have a problem there… have you ever checked to see if you have Endometriosis? A normal period should NEVER be painful.
    Good luck with the cup! Definitely worth a try 🙂

  9. Adrienne

    July 5, 2019 at 2:45 pm

    I’m in the EXACT same situation with my cup. Still learning. First 2 cycles were unsuccessful with one successful insertion but it didn’t seem to last. The tab was problematic for me- as in it was poking me. Ouch! I have an INTIMINA. Please keep your updates coming. I’m thinking I should practice insertion in between periods- lube is a good idea- to get comfortable without the panic of needing it to work. I admire your determination!

  10. Cat

    July 7, 2019 at 11:34 am

    I’ve been using a cup since my period returned after my last baby, so, about 4.5 years now. I’m 42 now and can’t believe I went so long without really knowing about them. Sure, I’d seen them next to the natural sponges at Whole Foods a few times, but never really gave them a second glance. I also have extremely, EXTREMELY, heavy periods. So heavy I’ve had all the work ups to make sure I’m okay, but apparently I’m just old, have had four kids, and this is pretty common. That said, cup forever. I always tell people it takes at least two months to master. I ALWAYS wear Thinx or Knix during the heaviest days as back up but I’m definitely a pro now and will never look back. My daughter’s period life will be so different from what I had to go through with gross pads and gross tampons, ugh. Period care has definitely improved over the years.

  11. Meg

    August 2, 2019 at 11:14 am

    I was super nervous but found this article to be super helpful: https://www.bloodandmilk.com/how-to-use-a-menstrual-cup/ I literally just followed step by step haha and haven’t had issues yet! Good luck!

  12. Natalia

    August 10, 2019 at 11:12 pm

    I just tried the NIXIT disc, it’s the BEST EVER! It has a different shape, than regular cups. I had zero leaks this period, and it’s so comfortable I forget it’s in there. I’m obsessed. I used the lunette cup for 3 years but I had to use panty liners, because no matter what, I would leak. It cost bit more than a regular cup ($50) but, worth every penny.
    5 stars. Would tell a friend.


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