Self-Taught: Remy Kassimir - Blood + Milk
Remy Kassimir

Self-Taught: Remy Kassimir

You have all heard the classic female tale. Whether bleeding through your khaki uniform pants and your mom telling you, “You’re a woman now,” losing your virginity in the back of an old pick-up truck at summer camp, or becoming a mother after a seamless pregnancy and having your perfectly round-headed and healthy baby placed on your ready-to-breastfeed chest, you know these movie quality stories to be wildly uncommon. You instead, as resilient you are, guide yourself through the untold truth of femininity.

You throw away 100 tampons before knowing how to use one. You lose your virginity on a messy, confusing, and imperfect night and you experience birth in a deeply personal and courageous way that likely completely deviated from your best-laid birth plan. Yet, you, as a powerful and resourceful force of nature, figure it out. You talk to your friends, converse with the Google Search Bar, and overcome the unknown. 

Welcome to Self-Taught, where we discuss how women teach themselves about their bodies—because we’ve all been failed by school courses, perplexed by movie scenes, and embarrassed by conversations with parents and peers.

For far too long, flawed systems and unrealistic media have depicted the female body—the female experience—as too skinny, too fat, too messy or neat, disgusting or pristine, but rarely the truth that lies between every extreme. In Self-Taught, we’ll share stories of how women uncovered flaws in systems, products, and lore, and taught themselves that there is a better way—and they deserve better. 

We have probably all sat around wondering if our bodily functions were normal. For Remy Kassimir, she wondered that for about a decade before deciding she deserved more in bed. At 28, Remy was unable to orgasm, so she hired teachers, did her homework—which instead of a pencil involved a vibrator—and finally brought herself to achieve an orgasm, all while speaking about it on her podcast, How Cum.

Can you tell me about where you’re from and the culture regarding sex in your hometown?

I’m from New York. So I think the culture regarding sex has a very wide range. There are a lot of different people in New York, specifically where I grew up in the Upper East Side, with a Gossip Girl lifestyle around me, where everyone seemed to be moving a lot more quickly than I was. I always felt like the last virgin standing and I was actually referred to as that at the really old age of 16. 

Did you ever receive a sex talk from your family or school? Did it ever discuss pleasure? 

We had sex ed from fifth grade on, which is great, but we never learned about pleasure—specifically female pleasure—in any of those classes. The only thing we were taught in those classes about the female body was the reproductive system, how to have sex, how to have a baby, and how to avoid having a baby. There was never any conversation around, “you can masturbate and there is this really great feeling at the end of that and no matter how many times you do that you won’t get pregnant,” which I kind of wish had been the sex talk. My dad never talked to me about sex too much, but he did put a heavy emphasis on you have to find the right person. I don’t think that is the best advice. My mom was much more open about stuff. She would be like, “yeah, sex is supposed to be fun!” But the fun didn’t encompass any mention of a female orgasm. When she started listening to the podcast she got upset because she thought she had told me about all that stuff, she hadn’t!

Remy, you have been featured on Netflix, Vox, Cosmopolitan, and Refinery29, doing stand up and talking about the female orgasm on your podcast, How Cum. But I’m guessing you haven’t always had this knowledge about sex. When would you say you first became curious about sex? 

I’ve always been horny—always and forever. Always trying to hook up. Even when I was two years old in my stroller I would be making sexy eyes at boys. I always wanted a boyfriend. I always wanted to touch people. My friends and I would look at our vaginas in the mirror sometimes. I was a very curious kid and a very aroused kid. I was always sexually curious—if I saw an orgasm happening in movies or in Sex In The City, I would try to recreate that amazing feeling. I didn’t really know what I was striving for but when the vibrating razor came out, I may have tried that at 13. Obviously not the razor side. When Sex In The City started talking about The Rabbit I was 21. I bought The Rabbit. That is a very scary sex toy. 

It wasn’t until I was with my first boyfriend and we had been dating for two years that I admitted to myself and to him, “I am hearing about other people having orgasms and I don’t think it has ever happened to me before,” and he was like, “OK that is kind of shocking and something we need to try and figure out together.” I don’t think it was until I started stand up that I got really curious and really resentful that other people were cumming. I would go up to female comics after the show and be like, “Are you really having orgasms?” They would ask if that was a serious question. I would be like, “I don’t think I’m doing it.” Sometimes they would be like, “Oh, I feel so bad for you,” and then they would try to give me tips or an assignment to do. One of my friends said I need to masturbate for 30 minutes. One of my friends said, “I gotta lend you this guy who is great at giving head!” No, thank you. 

I would try to do some of the things they recommended and I would be overwhelmed with the feeling of my body being broken. Then I told my sister and she’s younger than me—so I taught her everything she knows. She was having orgasms alone but not with other people. If she could do it, I thought maybe then it was biologically possible. I wanted to do something that incorporated those assignments and kept me accountable. I thought of the podcast and each episode I would have guests on to tell me about their first time orgasming and then they would have to give me an assignment of something I would have to do for the next episode. And it worked!

I consider your podcast, How Cum, to be the epitome of Self-Taught. Why did you feel it was important to share your journey publicly? 

First and foremost, it was an accountability thing. If I was putting something out there and people were telling me that I had to do something, then I would actually have to do it because people would be expecting it for next week. It really started very selfishly. The only way I’ve ever known to be held accountable for something is to have it be public. I also thought it was really interesting when my sister did the research behind how many people were having orgasms versus weren’t—she told me it was a much more common issue than I had previously thought. I thought it would be great if we could help people in the process, but I ultimately really wanted to cum. 

What do you hope your listeners take away from your podcast?

I hope and I also know that they are taking away a lot more empowerment in themselves. It’s what I have taken away from it, too. I just want people to know that your vagina, penis, or whatever you have going on down there is great. It is there to give you pleasure. It is not there for anybody else. It is there for you. RuPaul says, “If you can’t love yourself, how the hell are you going to love anybody else?” I find that so true in life and in masturbation. You have to get to know your body. You’re going to be with your body your entire life. 

I used to think that sex was all about training for a guy to stick his penis in a vagina. I thought it was all hole and you can only get sexual pleasure if another person was in the room. That is so untrue. I have felt so liberated by knowing—and my listeners have felt so liberated by knowing—that we are the ones who can give ourselves pleasure. You don’t have to sit around for somebody else. When you do find somebody else, knowing yourself is going to make it a million times better. 

On your podcast, you talk a lot about the female body and the importance of a woman feeling pleasure. What makes you feel empowered during sex? 

I think I am much more comfortable in my body now. After having these conversations with other people and hearing that they have similar insecurities, I know that what I have is totally normal. It is always very helpful to me—and my boyfriend is very good at this —to give body worship and to give compliments during sex. Before he would just enjoy things, but I was like, “No! I need to hear it.” That made it feel a lot better. I think that is true for both genders. Somebody on one of our episodes said that there is nothing worse than a begrudging blow job. You just want to know that the other person is having a good time with you. 

Were you always comfortable on the podcast or did it take time to become comfortable talking so openly about your sex life and asking people about theirs? 

It took a really long time. I don’t really recognize myself in early episodes because I was so scared and nervous. I felt like there may be this backlash of, “oh you’re fucked up,” or, “that’s so sad for you.” I was always scared of the onslaught of guys being like, “Oh I wanna make you cum.” That terrified me. It took a while, except I came in six episodes. So I guess after that I felt really good. 

What do you do outside of the bedroom to make your sex better? 

Therapy is a huge thing. I treat the podcast as therapy too because we talk about so many topics that I think only I am dealing with, but when I talk to other people about it, it seems so normal. One of the episodes was with Dr. Ian Kerner. He wrote the book, She Cums First. It is all about pleasuring women. On that episode, I was saying that there were times I was struggling with my boyfriend not initiating sex as much as I do, and that makes me feel unsexy or unwanted. He was like, “Did you ever consider that he just has a lower sex drive?” I really didn’t. Because I was just considering how I was feeling at the moment. That is therapy for me. Just talking to other people. 

I also like to do a little ritual before sex. Not necessarily all the time, but I realized that when I was feeling self-conscious during sex, I would think the person thought I was gross or not groomed in a certain way. I realized, no I’m probably thinking I’m gross and I am not groomed in the way that I find sexy. Now I make sure that I find myself desirable before I go into an encounter. 

What is one thing you want to teach others about sex? 

Not everybody needs to cum at the same time. I think that was a very big misconception that everybody needs to cum at the same time. In romantic movies, the guy and the girl are always cumming at the same time. Or even in porn, the guy and girl are always cumming at the same time. That’s not real. That’s a very heteronormative script, too, and one that favors the male.

Only 8–25 percent of women can cum with just penetration alone. So it is giving people this fake idea that men can readily give orgasms with only their penis and women should be able to do that. It makes people feel so broken. Most of the time, you’re going to have to have a lot of clitoral stimulation and it’s going to have to be at the same time that something is in your vagina. That is when you will have a vaginal orgasm. But you shouldn’t be shooting for this white whale of cumming with penetration alone. It’s not fair to you. It’s not fair to your partner.

Give people their turns. A lot of people are on different time schedules. That is why the pleasure gap is so huge between men and women. Men will typically take less time than women to cum. Wait for the woman to cum, and then you can do your thing and pass out. 

What is the one thing you wish your younger self knew about having sex? 

I wish my younger self knew about masturbation, honestly, because when I thought of the word sex, I thought of intercourse, or a blow job, or something with another person. I want her to know she can have sex with herself every day and never get pregnant and have the best time of her life. I wish I could tell her to buy some toys and not a vibrating razor. Maybe something with suction technology. Also, to speak the fuck up. There were so many times I was having fun during sex but I could have said, “Keep doing that more,” and maybe that would have resulted in something. I was very quiet but now I am a lot louder—in and out of sex.

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