Exploring queer sex – Jessi (the return)

Jessi Kneeland delves into her intimate journey exploring queer sex. Get up-close and personal with her revelations and experiences.
Good Girls Talk About Sex
Good Girls Talk About Sex
Exploring queer sex - Jessi (the return)
Episode art "Exploring queer sex - Jessi Kneeland"

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Jessi Kneeland is a 32-year old, cisgender woman who describes herself as white, bisexual, single, and monogamish.

Jessi gets up-close and VERY personal about her recent explorations into sex with women. This is Jessi’s second appearance on the show and she is the body image coach who has supported me through my own sexual exploration over the past few years.

The major theme of this episode is Jessi’s detailing her first serious explorations into queer sex and partnering with women.


  • Jessi and I talk about how people respond when we call ourselves bisexual, how we signal gender and sexuality through our appearance, and also dive into the ever-thorny question of … how do you define sex?
  • Jessi describes how she learned about stimulating her G-spot and achieved female ejaculation (“squirting”).  She gives a detailed explanation and tips for other people who have vaginas (or play with vaginas!) to follow her lead.
  • Extended Q&A

In this episode we talk about

  • Realizing that not everyone is attracted to all types of people and bodies
  • What does hetero-romantic mean?
  • How she dresses and presents herself determines the people who are attracted to her
  • How people socialized as female communicate and respond differently than people socialized as male
  • Why it can be challenging as a female to “hit on” other females, especially given the work that Jessi does
  • Jessi’s hot night with a beautiful woman in Portugal
  • Do you have sex during your period?
  • Have you ever had a sexual urge that confused you?
  • How often do you masturbate?
  • How do you feel hearing other people have sex?
  • What activity is most likely to bring you to orgasm?


Full episode text

LEAH: Hi. I’m Leah Carey and this is Good Girls Talk About Sex. This is a place to share conversations with all sorts of women about their experience of sexuality. Before we get started, I want to tell you this. These are unfiltered conversations between adult women talking about sex. If anything about the previous sentence offends you, turn back now! And if you’re looking for a trigger warning, you’re not going to get it from me. I believe that you are stronger than the trauma you have experienced. I have faith in your ability to deal with things that upset you. Sound good? Let’s start the show!


LEAH: In today’s episode again with Jessi Kneeland, a 32 year old cisgender woman who describes herself as white, bisexual, single and monogamish. You may remember Jessi from Season 1 Episode 7. She is the incredible body image coach who supported me through my sexual exploration over the past couple years. While it isn’t my intention to interview people more than once on this podcast, Jessi is the exception.

She spends a lot of time thinking about the same issues that I do. She’s actively excavating them in her own life and she is remarkably cogent in talking about challenging subjects. Recently, she wrote about beginning to explore queer sex and she was able to express some things I’ve long felt but never been able to put the right words to. You can find her online at jessinieland.com and at Instagram at Jessi Kneeland. I’ll put those links on the Show Notes. And now, for the second time, I am so pleased to introduce Jessi!

So Jessi thank you so much for being here today.

JESSI: Thank you for having me. I’m excited to talk about this stuff.

LEAH: You recently sent out an email to your list. People can find you at jessikneeland.com and sign up for your weekly emails, your transparent Tuesday emails. You recently sent out an email about exploring queer sex that really got my attention because you were able to verbalize some things in that email that I have always felt but had not been able to really put coherent words to.

So I would love to, just before I start asking you more specific questions, have you talk a little bit about where you are in that process. Is experimenting with women new for you or is has this been something that’s been going on for a while?

JESSI: Yeah. So I would say that I have always known that I was bisexual sexually that I was always attracted to women and men and I mean that like before, as far back as a person has thoughts about

these things, I think that was always obvious to me. I don’t know if it’s weird or not I guess but I didn’t feel like I needed a label in any way. It honestly just felt so dumb that someone wouldn’t be attracted. It just felt really obvious to me. It was like, “Yeah. You know how we’re all attracted to everybody?”

And I wouldn’t say that I really embraced the bisexual label unless someone was specifically looking. If I was dating a guy and we were talking about a threesome for example. They’d be like, “Oh, so you’re really into this? You must be bisexual.” And I’d be like, “Sure. Call it what you want.”


JESSI: It just didn’t resonate for me as a label because again it just seemed like I liked pretty things. Why does that need a label and identity? But always that was within mind that I would date men. I only ever dated men and I found women attractive and I hooked up with women over the years. There were a handful of experiences here and there.

I definitely would’ve liked more but I kind of didn’t know how to make them happen. A lot of moments in my life where one of my very lovely straight girlfriends would be like, “Oh my God, wouldn’t it be crazy if we made out right now?” And I’d be like, “Yes. I think we should do that.”


JESSI: And then they’d be like, “I know. It would be wild.” I’d be like, “Yeah. We can.” So I think there was something about me that drew a lot of that energy so I made out with straight girlfriends and I had hookups and threesomes and things that were all sort of scratching that itch a little bit sexually but it literally never occurred to me to just date a woman.

So I would say when I finally heard the word heteroromantic, a few years ago that that was, “Oh. That’s what’s going on is romantically I think men, sexually, everybody.” But part of that I’m now realizing was pure conditioning. I didn’t know how to get a girlfriend. I didn’t know where to go. I didn’t know how to talk to women. Given the work that I do, I didn’t want to ever make a woman feel objectified or sexualized and so I kind of was like, “Ugh, I’ll just date men it’s easier. I know how to do it. I know when they’re hitting on me. I know how to escalate that.”

So I’d say it took a really long time to embrace the term bisexual which I now feel like that’s accurate and I’m willing to say that the label is useful to use at times. And then also there’s something about the fact that I’m actively dating women now that is very different and new. So the attraction is not new at all but the romantic aspect is within the last year.

LEAH: So you just brought up some terms that have been really important to me but some people may not yet familiar with, which is this distinction between bisexual and biromantic or heteroromantic. There’s a spectrum of sexuality but there’s also a spectrum of where we choose to find our romantic attachments and that they don’t necessarily always line up.

I have discovered in my last few years of exploring that I am equally sexually attracted to both men and women, potentially a little bit more attracted sexually to women but my romantic attachments are

primarily to men. And that once I’m romantically attached to a man, my sexual attraction to him grows exponentially.

JESSI: Yeah, I would say I felt very similar.

LEAH: What’s your dating life now? Are you primarily pursuing females? Are you primarily pursuing


JESSI: Right. Because I’ve been travelling the last year, there hasn’t really been an opportunity until very lately since I’ve got to LA two months ago to really pursue women. Now, that’s not to say that I wasn’t interested or keeping an eye out, but you get on Tinder in Mississippi or Texas


JESSI: Or even upstate New York frankly and it’s like dude, dude, dude, dude, woman. And so not that those dudes were particular interesting to me anyway so I’d say a lot of my single ship there was a real bummer just in general. But I’ve been excited about being in LA so that I can start purposefully pursuing relationships with women which is something that I say on dates now. “I’m looking for a girlfriend,” It’s a funny thing to say to me but it’s true.


JESSI: It just is and so I still match with men on dating apps and I still go on dates with them when I’m like “I have a free night.” They’re the only ones who respond but they are very much Plan B to me and I call them that too which as you can imagine doesn’t make the dates go super great.


JESSI: But I’m like, “Hey just so you know, if a woman was interested, I would not be seeing you.” Because that’s the truth and I think that a lot of the last year has been pushing me in this direction but only since I’ve been to LA has it literally been logistically possible.

So yes, I am trying to date women. It doesn’t always work out in account of the abundance of men is just higher and I find in terms of who matches with me, it’s like all of the guys and a small portion of the women which is something that I’m now thinking about like how I present myself. I’m not gay enough looking to get the people that I might be interested in because there’s this whole world of gender presentation in the LGBTQ community that I have never really had to think about before. And so it’s definitely an active choice.

My hair is really long right now, I look quite femme for myself. I shaved my head a few years ago. It’s not like I necessarily prefer myself one way or the other but it’s interesting to notice that if I wanted to match with the femme beautiful women who I see, I probably can’t really look like this and what does it mean about the power dynamics? Am I trying to step into my masculine side? Is there some energy that goes along with that sexual dominance or something? It’s a mind blowing exploration and I’m loving it.

It’s so interesting. But I definitely feel like I’m at the baby, the first very beginning steps of exploring as consciously as I am.

LEAH: So from just a logistical point of view, when I started Internet dating ten plus years ago, and I knew that I was interested in dating both men and women and let me say I was in [10:47], New Hampshire. There was not a chance in hell that was going to happen anyway.


LEAH: But you had to either say you were interested in men or you were interested in women. If you wanted to be able to date both, you had to pay for two separate profiles. It was absurd, the dark ages. But now, apps and all of that are much more open to the possibility as bisexual. As time went on, I discovered that if I put bisexual on my profile, I would be rejected both by the men and the women. And I wonder how that is for you now.

JESSI: It is still like that. In fact, a lot of the women, I’m on an app called Her, which is just for women or trans non-binary basically anyone but cis het men and so I see a lot of profiles that say, “Lesbians only. Not interested in bisexual women.” And I’m interested in that because I have to assume they have good reasons for it to be such a common trend like my guess is that either it’s what they connect with better.

There’s just a certain amount of connection that they get better with somebody who shares a certain identify or orientation with them. Or that a lot of women may identify as bisexual and like me really are heteroromantic and they’re going to drop the women and find a guy in the end and they just don’t want to be messing with that kind of energy. So it’s really interesting to see that. And I can’t really get offended because you want what you want but there’s a part of me that’s like, “But why? I’m cool too.”


JESSI: There’s this feeling that the bisexual doesn’t appeal and with the guys I think it’s less of a problem but definitely it’s in my bio. It says I’m more into women than men now, FYI. And so it’s the first thing the men will talk about like, “Hey, sorry I’m a guy but you’re so cute,”


JESSI: And I’m like, “That’s cool. Whatever.” So I think it’s on their minds. It definitely strikes them differently than just being straight-straight.

LEAH: One of the things that you mentioned a minute ago was the sort of communication gap between males and females or I want to be a little more broad and say people who grew up in boy bodies and people who grew up in girl bodies because that really determined how we were socialized.

And so in this email that you sent out, and I’m going to make sure that there’s a link to it in the Show Notes so people can go back and read the whole thing, but here’s one of the things that just struck me so much.

“Plenty of male partners would ask me to tell them what I liked, and I’d be like, “Oh, wait that’s a big question. I mean how much time do you have?” One big reason is that there’s a massive language barrier between us. Men seem generally to assume that the answer to what I like is a stroke or act or position or technique. He’s just trying to give me a few minutes of me time before we get to the real sex.”

That struck such a deep chord for me and I’d love if you could talk about that a little more and what your experience is of that with men versus with the women that you’re dating now.

JESSI: Yeah so I think that in part because I grew up in a girl body, I was socialized to put other people’s needs especially the needs and desires of boys and men that everything in me like I have rebelled against all of that socialization as best I can. I’ve unlearned everything that I possibly can and I continue to do so but everything in me still has an intrinsic desire to please and to make the other person happy, especially if it’s someone that I like and I’m attracted to and especially if it’s my boyfriend.

So it’s really, really impossible for me to know what I want when I know he wants something else. And I’ve worked really hard to stay in touch with what I want but it is still a challenge and so I think in moments like that, I need to know that this man fully, fully wants me to get what I want and is willing to go way off the script or way off in a totally different direction that is not what sex normally looks like in order for me to even remember that that’s what I want.

Because otherwise, it just gets scrambled. In that moment, when I know he wants to have sex but he wants to make me warmed up first, I can’t really stay in touch with what I would actually want. It’s like that gets taken off the table and now I see four options in front of me. He could go down on me, we could do this. We could do this. We could do this. And so, I pick from what feels like the available options but that’s not deeply satisfying sex for me.

That’s just fine sex or even good sex but not like oh my god, life-changing sex. I’ve had experiences with men where it was very clear because of how they held the space and set up the interaction that I was allowed to and in fact that he got off on me getting exactly what I wanted including these very intense off the script experiences of a lot of times not involving genital touch or not involving anything that they would normally think of as sex.

It is super arousing to me to have a deep connecting conversation for example or to feel appreciated and seen. So in that moment where he’s like, “What do you want?” I can’t be like, “Tell me how you see me.”


JESSI: I would like to and I have but for the most part that would be a weird interruption of sex. And I find that it’s just not as weird with women. It’s a lot easier because I think there’s that shared understanding that it’s not about the technique. They don’t have this immediate outer desire. They’re just not trying to just thrust. They’re like really there with me, curious what I like and wanting to have an intimate experience.

And of course, I’m painting very broad strokes here, it’s not to say no women are afraid of intimacy and just want to get their fuck on because certainly some do and it’s not to say there aren’t sensitive men who want to have tantric, connected intimate sex. There are, but in broad strokes, I just find it a lot easier and a lot less like I’m trying to turn a boat around to be like what I want most is to have you describe how you see me or what I want most is for us to really feel safe and connected before touching. That kind of stuff that really, really turns me on is just doesn’t feel as interruptive or as weird with women.

LEAH: With my current partner, one of the things that we do a lot, we watch a bunch of TV together and we will lay longwise on the couch with him behind me with his arms around me and cuddle for hours without anything happening.

And there will be a moment at some point where all of a sudden my body will switch on and I’ll be like, “Oh yeah, now’s the moment.” And it’s not that I can’t get turned on any other way, but that long periods of feeling safe and connected and warm like there’s no other expectation of me somehow allows me to have that level of safe and connected that I’ve never been able to feel with any other man because there was always that push and drive to the sexual act.

I want to go back and pick up something else you were saying a little bit ago about it being a little bit more complicated with women because you don’t want women to feel like you’re preying on them and this is a conversation that I’ve had numerous times with my other bisexual female friends that we all feel this feeling that I don’t want to come onto women because I know how it feels to be come onto by someone I’m not interested in. And so I don’t ever want to put somebody in that position. So can you talk a little bit more to that?

JESSI: God yeah. It is a new thing to think about because of the work that I do. I hold a very, very strong and safe space for women and it is the default that I think when I move through the world, I tend to be in that mode. Like if I meet a woman at a party, my first thought for her as we’re chatting is concern about her own self-worth and how she sees herself and all of the red flags go up when she mentions her thighs or what she’s eating or something like, “Oh, god. She probably has these negative self thoughts that I work with my clients on.” And it’s important for me not to compliment her appearance or her weight and instead to let her know that I think that she’s wonderful based on what I’ve just seen. I go through all of this stuff to hold that space and it’s my default.

And that feels really non-sexual so it’s been a kind of odd transition for me to be like I’m still a sexual being and I’m still attracted to people but I can’t really do that thing and to me they still feel separate and I don’t know if they need to feel separate or not. But it’s something that I’m still experimenting with and exploring and still does not feel comfortable. So I think this is part of the reason I haven’t dated women before and I haven’t ended up with a relationship with one is like I don’t know when a woman is hitting on me, I don’t know how to escalate it if she was, the skills are different, the body language is different, the cues are different and so I am afraid of overstepping making somebody uncomfortable unless I’m getting really, really, really strong cues, which is why it’s nice on a dating app because it’s like she and I agree. If there is attraction, then good.

It feels really much peaceful for me to do it that way whereas if I was in the wild and I’m at a bar and I met a girl and we’re talking, I would assume that she was not gay, not interested, I would assume that even if she was gushing over me, we might be great friends. And so there is until something gets switched, I don’t even experience attraction because that is my primary focus. And so part of this exploration of myself is putting myself in gay spaces is like putting myself in spaces where I can take the blinders off that I walk around with that keep me from being attracted to someone who I shouldn’t be attracted to.


LEAH: You know what’s so great about Jessi? She is incredibly willing to give fully of herself in the moment that we’re talking. The answers to some of the questions I asked changed in the months between our two interviews and that’s so normal. We grow and change with every experience we have. We also get to grow and change by listening to others talk about these topics that have been hidden for so long.

That’s what [22:42] said in her recent Apple Podcast review of the show. “It’s so powerful to hear women speak about their sexual lives in an open and honest way. The good, the bad, all of it. Host Leah Carey asks the kind of questions that I’d be too shy to ask my own girlfriends but I’ve wondered. If you’re interested in the inner lives of women, you’ll enjoy this.”

If you’re also enjoying this show, please take a minute to leave a rating and review at Apple Podcasts. Knowing that you’re getting something out of it, keeps me motivated to keep producing it. And, if you want more of this amazing conversation with Jessi Kneeland, you’re in luck.

Our conversation went on extra long so there are lots of goodies at Patreon this week. This week’s rewards are at the 1 dollar level, there’s a detailed conversation about how Jessi discovered her G-spot, learned how to stimulate it and has now learned about squirting. This is a not to be missed conversation, which is why I want to make sure every patron gets to hear it.

At the 5 dollar a month level, Jessi and I talk about how people respond when we call ourselves bisexual and also dive into the ever thorny question of, “How do you define sex?” Jessi and I are both excited for the Q and A, so at the 7 dollar a month level, there’s 30 full minutes of conversation. One note, this includes the G-spot conversation so if you’re at this level, you don’t need to listen to both. As always, at the 10 dollar a month level, you’ll get a month of that and a monthly ask me anything.

And, as you know for Season 2, 10% of all Patreon donations I receive are going to ARC -Southeast, an organization that provides financial and logistical support to people seeking reproductive health services in Southeastern U.S. States. To learn more and to become a community supporter, visit patreon.com/goodgirlstalkaboutsex.


LEAH: You’re so much in the middle of this exploration. Do you have any thoughts about what you hope the end point for it will be or are you too much in the middle of it to even know?

JESSI: I think I’m too much in the middle but that said, I have day dreams about falling in love with a woman and her being the life partner that I always wanted a male partner to be and was disappointed in one way or another. So there’s certainly is a desire for that to be true but I don’t know if that’s true. I might end up in relationships with women and end the same way where I’m like maybe it’s not about male-female at all but for me right now, putting myself in these positions, is giving me a chance to explore if that is really the solution that I’ve kind of looking for as far as dating goes.

LEAH: Like you, I knew I was bisexual or I didn’t even have a word for it but I knew that I was attracted to women early on and didn’t do anything about it and as my relationships with men grew more and more fraught, it actually made me more frightened to pursue having sexual experiences with women because I thought what if they’re not better?


LEAH: What if the answer is just that I’m broken? [LAUGHTER]

JESSI: Oh my God! Yes, I get that. I think there’s something similar, not sexually broken, but there is something that I have been unsatisfied in my romantic relationships in a way that is a unique pattern to me. Feedback from them and it’s something that I’ve already observed in myself and there is a part of me that’s like, “Shit, man. It’s not about gender.”


JESSI: And it certainly in some way feel a little bit like I mean I’m still going to have my stuff in a relationship with anybody but when I first realized this it was like the blinders came off for the first time and actually I can tell you the story of when this was if you want because it’s a very specific experience.

LEAH: Yes.

JESSI: So I was in Portugal and for months I was living there having thighs whole exploration about gender. I hadn’t thought about my sexuality too much beyond the awareness that when I lived somewhere where it was possible, I did want to try to pursue women more.

Portugal was not abundant in that way so I was like, “Wherever I get somewhere next.” And then, on my last night, I had met this bartendress multiple times at a place where I really liked to go and it was my final night in Portugal. I was like, “I’m going to take myself out.” And I went to this place and I was sitting on the bar and instead of bartending she was sitting next to me.

She was in front of the bar and we started chatting and she’s so pretty and I was definitely still in the place of like, “What great friends we could be! What a fun experience!” The default thing is that she was probably completely straight and she looks like a very feminine. Anyway we were having very connected slightly tipsy fun chat and then she had mentioned her ex boyfriend and I said something along the lines of “Are you completely straight?”


JESSI: And she like gave me this look and was like actually no. And it turns out that she had been married to a woman and so just hearing that information, it was like a big chunk of blinders came off and I was able to notice that we were flirting, which I could not have told you until that moment, and I was very attracted to her which I could not have told you until that moment.

So I would have said she was beautiful because she was but I wouldn’t have said I’m having a response to her beauty until I knew that she was somewhat available in that way. Now she hadn’t said I’ve been crushing on you, but she gave me this context where this first set of blinders came off and I was like, “Oh, damn.”

And then as it kind of continued to escalate and I already had a bit of that context in my mind, it continued. It was like more and more blinders came off and I was like, “It’s on. This is happening.” She’s flirting with me. She asked to kiss me. We made out outside. A bunch of guys were watching while they’re having a cigarette just like literally Portuguese people just watching.


JESSI: And then we left and we went dancing and on the dance floor, we were all up on each other. It was so sexy and I realized in that moment how grateful l am to be a female person because if I’d been a guy and was just like, “Ooh, I think I’m just going to make out with this guy now”, there would have been a very different reaction I think whereas to women being all up on each other on the dance floor is like nobody really cared. So that was an interesting thought that I had at that moment. And then it went on we had this awesome night that ended in hooking up and I have never felt so proud of myself for making a woman orgasm.


JESSI: It was like don’t even know how to put it. I was so honored that insanely beautiful creature wanted me to touch her and then when I did and it felt good, I wanted to high-five everyone on Earth. And I’ve never had a feeling with a guy before. I mean I would certainly get some sort of validation from it and pleasure and all the other things, but I’ve never had that particular feeling of like, “I can’t believe that someone that hot wants me to do this to them.” And it was just delightful.

And the whole next day I was in the airport flying back to the U.S. The whole next day I was uncontrollably giggling to myself like, “I can’t believe I got to do that.” And our conversation before it turned really flirtatious and then sexual had been about, I hope she doesn’t listen to this podcast.


JESSI: She’s going to know it’s her. Anyway so our whole conversation had been about her travels. She drove around the country in a van for a long time, drove around Europe in a van. And so I was like so enamored by her courage and her badassery and so there was this feeling that I don’t think I get with

men much which is like respect. I respected her as a person so much that the fact that she wanted us to be sexual felt like I just felt so goddamn cool.


JESSI: I felt like my own status in my own eyes went through the roof because she, this amazing human, saw me as appalling. I don’t know I can’t even describe it but it was so amazing. And so the whole next day, I’m processing it, I’m giggling, I’m in the airport just having this whole experience being like, “What happened?”

I was feeling very sad that it hadn’t happened earlier because I would absolutely would have like dated her. We would have spent every day together and I wanted her to be my girlfriend. I’m not even kidding. I had visions of like her being my wife. She was just this delightful human and she had a kid who was like an early teenager but she was talking about how she loved babies and she loved being pregnant. And this was before we got to the flirtatious part, I had this flash of like, “God, she’d be such a cute hot pregnant person and mom, whatever.”


JESSI: It was probably the next day. I had this thought, “Oh my God, she could be my cute hot mom.” [LAUGHTER]

JESSI: If we dated, I could just have that and it was mind blowing that it had never occurred to me to be romantic with a woman that way and it was like I needed 8000 blinders to come off in exactly that order for me to even realize the next day like, “Oh my God, if I dated a woman, she could be pregnant and I wouldn’t have to. We could raise kids and we would be on the same page and she’s so cute.”

And the way that I feel about women is that they’re so much better. They’re so awesome. They’re so powerful. They’re so strong. And all of this stuff that I love about them, I could just date someone like that. And I’m saying this all and it sounds ridiculous to me but it was the first time that I’d ever had any of those thoughts so that was when the real process of like, “I think I want to date women” began.

And it was like pretty night and day I would say. And since then, I’ve found myself attracted to women in a very different way without all those blinders built in I think. They’re still there in different contexts but I would say that I never was attracted to feminine looking women. I always thought I liked boyish androgynous ruby rose type of women which kind of makes sense because I think I was only comfortable with being attracted to people who sort of the experience profile of who had given me pleasure and who I had sex with.

And so this changed that. This gave me a whole new context for who I’m attracted to and who I connect with. I don’t know it changed a lot. It’s just interesting to notice. I think all of those things were there but they were just socialized to be kind of the dimmer switch was down low.

LEAH: I love that story by the way.


LEAH: That’s an awesome story. It’s really interesting to hear you say that about who you are attracted to and then to reflect back to what you said earlier In the conversation about thinking that the way that you’re presenting your gender right now may not necessarily be attracting the sort of femme women that you are interested in and so why? Why do you assume that a femme woman wouldn’t be interested in you presenting exactly the way that you are?

JESSI: So part of it is who is matching with me on apps and it tends to be statistically more masculine presenting women and part of it also is having talked with basically every day I go on with a woman and I’m like sharing where I’m at, just getting Intel so where do you meet women?


JESSI: Yeah, something that I’ve heard a lot is that it’s really, really unusual and it’s actually a little bit mind bending to see two feminine looking women in a partnership because it’s rare, not because it’s impossible. It’s just rare.

And so that has led me to exploring and asking questions like is it rare because there’s like a social pressure for one person to look and take a certain role? Or is there an attraction component to this? And if so, as a person who I feel is very fluid in this way and over the years with my hair length and clothing choices, I think I can go back and forth between these two ways. I wouldn’t feel free being just one role in a relationship.

If somebody chose me because of how feminine I’m looking I was, then half of me wouldn’t necessarily be her type and vice versa. So it’s interesting to think about myself in this way because the gay culture certainly it encourages I think a little bit of identifying one role or the other and it’s just a brand new thought. Oh, do I want to be identified with one or the other? Not really because I think like in every area of my life, I have a foot in both worlds and I am attracted to both androgynous looking or feminine looking women and so for me, I just don’t want to have to shave my head to attract the right person because that necessarily doesn’t feel genuine to me at the moment. But I can see why it would actually perhaps be a good move for me in the long run if there is a snap judgment that happens about who I’m the right partner for.

LEAH: That’s fascinating and I wonder because my experience in Portland has been very different than that. I see couples where those gender norms, that’s a weird word to use when you’re talking about non-traditional relationships, but it is entirely possible just to see two femme men together or to see two butch women together. And so it makes me curious about whether that has something to do with how LA tends to be like people are very focused on how they’re presenting themselves at least that’s what I assume because it’s the world of Hollywood.


JESSI: That’s interesting. I could totally see that. I mean like I said this is such a baby exploration, I’m so new to it I could end up wrong but I think a lot of the conversations I’ve had, they’ve all been with

woman in LA and it has certainly and also the matches that I’m getting has certainly felt like a pattern and there’s something else to it which is I don’t know if it’s a pattern because of how they want to be or if it’s a pattern because they’re all following the rules so yeah. I could see in a place like Portland maybe those rules don’t have strong of a hold and therefore the same people just get to present differently.

LEAH: Yeah. And there’s a very big culture here of gender fluidity and gender nonconforming and even the driver’s licenses recently, you can now put gender nonconforming as your gender on your gender license and that is a thing here. So I think that there’s just a lot more acceptance of that sort of fluidity that maybe is different. Well, certainly different in other parts of the country.


JESSI: Right. Right.

LEAH: Maybe even in the other parts of the West Coast.

JESSI: Right.


LEAH: Before we finish up, let’s do the quick five. Five quick questions we’d usually be too polite to ask any good girl.


LEAH: Do you have sex during your period?

JESSI: I have. I don’t really get a period anymore which is actually a whole other thing. Hormonally speaking, I’m kind of a disaster at the moment but I did when I had it as long as the other person was super, super into it, as long as they really didn’t care.

LEAH: Have you ever had a sexual urge that confused you?

JESSI: Hmm. I would say I’ve had a lot of sexual urges that have made me curious and certainly a lot of

this exploration that we’ve been talking about has brought up many of those moments.

A good example would be like I’m attracted to women but have not been attracted to trans women and so even though I think they’re beautiful, it’s interesting to me just like why not? And then, trans men for some reason there’s a lot more potential there. I’ve seen trans men that I’ve found attractive and the thought of like, “If I swipe right and we talk and then we hook up”.

I just don’t know enough about what I would be attracted to and what I would want to do with somebody depending on the different options and I would say there’s a lot of confusion about that for me in terms of do I want this and if so, it’s just interesting to me like why, what am I being drawn by in a trans man that isn’t there in a trans woman? I don’t know. I’d say there’s a lot of things that make me curious. And perhaps confused is the right word as well, maybe nervous even sometimes.


LEAH: How often do you masturbate?

JESSI: Ooh, that changes a lot as well. And I’m noticing more with hormonal bullshit going on that I can go weeks without thinking about it and then all of a sudden for days, it’s like sometimes multiple times a day. That’s a new pattern. It didn’t used to be like that. I would say it used to be four or five days a week. It’s the same amount that I would want to have sex. And I think that it does seem to be shifting.

LEAH: I remember my masturbatory habits changing over time through my 30s. They changed several times and I have to believe that it has something to do with hormones.

JESSI: I’ve also gone on and off different birth controls for the past couple of years to try to handle this PMDD which is like a hormonal nightmare so I think that’s it’s responsive to that but it’s also hard to tell because it takes a while. It takes a few months for each thing to sort of stabilize so I can’t really tell exactly what’s causing what but it’s definitely shifting.

LEAH: How do you feel about other people having sex like if you’re in a hotel room or something? [LAUGHTER]

JESSI: I think it’s hot. I like it. I mean I certainly think there’s a bit of a, what’s the word for people who like to watch other people have sex?

LEAH: Voyeurism?

JESSI: Yeah, a little bit of voyeurism and I’m like, “Ooh.”


JESSI: So yeah.

LEAH: What is the activity that is most likely to bring you to orgasm?

JESSI: My vibrator.


JESSI: But in terms of like partnered sex, my own hand, honestly probably, is the most likely because I know what I’m doing.


JESSI: I mean I can give instructions but it’s usually just easier to do it myself.

LEAH: Awesome. Jessi thank you so much. It’s such a joy to be able to have these conversations with you and thank you for helping me to get to a place where I can have them. I’m so grateful to you.

JESSI: Aww, thank you. I mean I could literally go for another like 2 hours. This is such fun to talk about. [LAUGHTER]

LEAH: My guess is you will be the one guest who we have on every season.


JESSI: Awesome. [MUSIC]

LEAH: Thanks for joining me today on Good Girls Talk About Sex. If you have questions or comments about anything you’ve heard or if you’d like to be a guest on the show, please email me at leah@goodgirlstalkaboutsex.com.

I was only able to step outside my good girl box when someone I respected told me it was possible to do it. If you’d like to step outside your good girl box, I’m here to tell you it’s possible and I can provide you with tools to name your desires and communicate them effectively to your partner or potential partners. If you’re interested in working with me, visit leahcarey.com/coaching. You can find me on Facebook, Instagram, and YouTube at IamLeahCarey. You can find these links and any resources we’ve mentioned during the interview in the Show Notes. I’m Leah Carey and I look forward to talking with you again next week. Here’s to your better sex life!


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Host / Producer / Editor – Leah Carey (email)
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Music – Nazar Rybak

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