Dive Deeper with Leah Carey
I have been through the fire and come out the other side. Now I’m here to walk with you as you do the same.
I will help you take a stand for yourself, your desires, and YOUR PLEASURE.
Since beginning her transition to become a transgender woman recently, Kelly has discovered that she is interested in people of all genders. She discusses how hormone therapy has changed her body, her mind, and her orgasms.
Kelly is a 34-year-old transgender woman. She describes herself as white, bisexual, single, and currently exploring open relationships. She has no kids and describes her body as thick.
LEAH: Welcome to Good Girls Talk About Sex. I am sex and intimacy coach, Leah Carey, and this is a place to share conversations with all sorts of women about their experience of sexuality. 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: Hey, friends. I’m so excited about this episode. I know I say it every time and it’s always true. So, in the past, my conversations with transgender people have all been with people who were fairly far into their transition process. Lachlan, Trystan, and Davina were each several years or even more than a decade into their transitions when we spoke.
That’s why I’m so excited for this conversation with Kelly, a transwoman who at the time of this interview is just a few months into her transition. She’s taking hormones and has started to develop some new breast tissue, but voice training, surgeries all that stuff is no more than a concept she might consider at some point in the future. It’s amazing to have this conversation with someone who is so new in her process so that we can hear about the changes that are happening in the moment that they’re happening rather than years after the fact.
Now, as a reminder, when I speak with trans people on the show, I get to ask questions that would not be appropriate to ask a trans person outside this context. In general, asking a trans person what’s in their pants and what type of sex they have is not cool. But to be fair, it’s not cool to ask those questions of cisgender people either. So, let’s not pretend this is a particular burden we have to observe just for trans people.
I also know how uncomfortable it can be for people to approach a conversation with a trans person because they’re afraid they’ll say the wrong thing. Now, I have some leeway during these interviews that you don’t have in day-to-day life because guests come on this show already knowing what it’s about. But that doesn’t mean that I can run amok like a bull in a China shop and just ask absolutely anything without any concern for the guest’s feelings or sensitivities. So, I want to share with you the process that I go through for these conversations.
Before I hit record, I talk with the guest about the kind of questions that I plan to ask about their bodies, about their sex lives and I get their permission to ask those questions. I let them know, “If I ask you something that you’re not comfortable talking about, tell me and we’ll skip it.” During the recording, when we approach sensitive topics, you’ll hear me ask for permission or clarification again in the course of talking. And I leave this in the recording so you can hear what it sounds like to navigate these conversations hopefully with some sense of grace.
One more note, it’s common for people in marginalized communities to reclaim words that have been used against them. For instance, you might hear a gay man refer to himself as a fag. However, people outside those groups should not use those words because people in the dominant culture are the ones who wielded those words for harm in the past.
And the same is true is here. Kelly uses some words like “tranny” that are specific to the trans female community and should not be used by those of us who are cisgender. Also, in telling some of these stories about past experiences, Kelly uses terminology that would have been used then, but is not used today like “shemale.”
All right. Enough introduction. Let’s get on with the show. Kelly is a 34-year-old transgender woman. She describes herself as white, bisexual, single, and currently exploring open relationships. She has no kids and describes her body as thick. I’m so pleased to introduce Kelly!
Kelly, thank you so much for being here. I’m really excited to have this conversation with you.
KELLY: Thank you. So, am I.
LEAH: Yeah. So, let’s dive in at the same place that I start every interview. What is your first memory of sexual pleasure?
KELLY: My first orgasm, I definitely remember I was in the shower actually. I was somewhere between 11 and 14 and I had been trying to figure out how masturbation works for a while. And I was doing it where I was doing the standard tugging at it.
LEAH: And when you say it, do you mean your balls or your penis?
KELLY: Yeah, my penis. Sorry. And then, I had an orgasm. I was surprised how much stuff came out. And I was like, what just happened?
KELLY: Sexual pleasure though, I was definitely getting boners and stuff before then and feeling attraction to girls mostly, sometimes guys. I don’t really remember. Yeah, that’s the first concrete memory.
LEAH: Yeah. So, you said you’d been trying to figure it out for a while. Had you heard about something or read something that made you think this was something to try or was it an internal feeling in your body that there was something you wanted to do and you didn’t know how?
KELLY: I’m trying to remember because I feel like I should’ve known because I had a pretty comprehensive sex education. Yeah, I think it was more an internal feeling, I guess.
LEAH: Yeah. At what point did you begin to recognize that perhaps your body didn’t match your internal experience of your gender?
KELLY: I didn’t figure it out until last year. About a year ago, I was really starting to identify as non-binary online and switching to they/them pronouns and I was questioning. And then, last year in May is when I came out to myself and to my best friends.
But then, looking back, there were definitely signs and things that made sense. I definitely remember having this attitude where I didn’t like traditional masculine Western sports and stuff. But then, there were ages where I feel like I went back trying to be masculine I think to fit in and stuff.
And then, also I remember two occasions where I did try on my then significant other’s clothes. First time was her panties and I actually shaved down there while she was out with her friends one time. And I just remember feeling really good. And then, I’m like, that was fun. Time to put that back on the shelf.
KELLY: And then, years later, one time when I was home alone, I put on her purple night gown that I really liked and I actually was rocking a full goatee. And I was looking at myself with the goatee in the dress and I’m like, this is really hot. I’m cool.
KELLY: And I felt really good about that. And I definitely had a feeling where I’m not sure that I’m a straight man and I need to figure this out. But it was more subconscious. And it wasn’t until, like I said, last year that I really consciously confronted it and admitted it to myself.
LEAH: Yeah. I have now used the words “penis” and “balls” twice. How do you refer to your genitalia so that I can refer to it appropriately?
KELLY: I actually really like the term girl dick. It’s cute. Yeah, dick is fine. Sometimes, clitty. That’s more of when I’m DM-ing another trans girlfriend.
KELLY: But no, girl dick is fine. We can use that. Balls are just balls. It’s fine. So, you can just call them balls. It’s what they are.
LEAH: All right. And when you think about yourself pre-transition, do you think of yourself as having a penis or a male dick or do you think of it as your girl dick pre-transition?
KELLY: That’s an interesting question. I don’t know because it’s definitely changed. It works different now. It’s smaller. I actually like that. I didn’t expect that, but I do. It’s complicated and it’s different for everyone, but I definitely am more on the side of I was always trans. I just didn’t know it. I don’t think I was ever really a guy. I think just people said I was a boy and I went along with it. And it wasn’t that bad. I didn’t really have really bad dysphoria until I got into adulthood and started getting hairier.
And for a while, it was unconscious. I used to have terrible depression and anxiety and just I hated seeing myself in the mirror. It was like a stranger looking back at me and I didn’t know why. I didn’t understand why until one day, I was like, hey, why am I following so many transwomen on twitter? Oh.
LEAH: There are some really funny conversations that happen on Twitter with their pipeline conversations like, this is this thing that “straight cismen” do. And then they realize, no, I’m actually a transwoman. I really enjoy those conversations.
KELLY: Yeah. Twitter’s wonderful. Also, terrible sometimes.
LEAH: Yeah, okay. So, when you were a child, what were you hearing from your parents, in your school, that kind of thing, about sex and sexuality?
KELLY: Yeah. So, from my parents, definitely they gave us the talk and they definitely told me it’s totally fine if you’re gay or anything, whatever. They told me and probably my sister that too. In fact, one time, I came home in tears and was asking my mom like, “Mom, am I gay? Because all the guys kept calling me gay all the time every day.” And she’s like, “You like, girls, don’t you?” And I’m like, “Yeah.” And I think that’s what took me so long to realize was because I like girls, so I’m not gay. But yeah, it was just confusing. It took me a long time to figure it out.
LEAH: So, what they were calling gay was I assume some sense of feminine energy about you? Would that be accurate?
KELLY: With the guys in my class, yeah, for sure. I was quiet. I was not aggressive. I actually did have a lot of feminine interests that I repressed. The first CD that I ever bought was a Sabrina the Teenage Witch CD. And I loved Spice Girls. But I’ve also had stereotypical male interests. I loved Ninja Turtles and Power Rangers and Dragon Ball Z and martial arts and video games. Obviously, a lot of that stuff is not really gendered.
LEAH: That’s the interesting thing. None of these things are inherently anything.
KELLY: Yeah, it shouldn’t be.
LEAH: But we’ve coded them that way.
KELLY: Looking back, there were certain interests of mine that I had to hide from my peers and others that were like, okay. But to answer your question, I did get a pretty comprehensive sex education at my Unitarian church. There was a program called Our Whole Lives. So, they taught us everything.
KELLY: They taught us about all the orientations, at least that existed back then in the 1990s. There’s probably a lot more genders today.
LEAH: That they knew existed, but yeah, now we have names for all sorts of things.
KELLY: Yeah, right.
KELLY: And we even had some speakers. This makes me hate myself sometimes because one of the speakers was a married translesbian and I remember the talk because it stuck in my mind. She was very interesting, but it somehow didn’t click. I don’t know.
LEAH: You weren’t ready yet.
KELLY: Yeah, I just wasn’t ready yet.
LEAH: That’s okay, yeah. So, it sounds like church was actually a really positive force in your life in terms of sex and sexuality.
KELLY: Yes. I’m so glad I wasn’t raised in some fundamentalist right-wing church. I was raised in the hippie dippy church. If you’ve not heard of unitarian universalism, look it up because it’s wild.
LEAH: So, in any of those conversations, other than the transwoman coming to speak to your group, was gender a part of that conversation in terms of there being transgender people?
KELLY: No. Again, that was definitely mentioned as part of the Our Whole Lives program. My parents, they were like, “It’s totally okay if you’re gay,” but I don’t think they were really super aware of trans people.
LEAH: Yeah. And that’s not uncommon though.
KELLY: They were surprised. They were accepting, but they were very surprised when I told them.
LEAH: Yeah. And what did you hear about male sexuality versus female sexuality?
KELLY: It’s funny actually because from pop culture and jokes and guys talk, you hear things. The stereotype that I always grew up hearing is that women don’t like sex. It’s just the guys or whatever. It’s just men who want sex. And as I went through my life and got older, I was like, that is not what I have found at all. Women be horny.
KELLY: If anything, because up until recently, I only ever dated or been with ciswomen and not that I wasn’t horny because I can be very horny, but I was usually the less horny person in the relationship.
LEAH: Yeah, that is such a stereotype. And sure, there are plenty of women who have lower libidos, but there are plenty of women who don’t and vice versa with men. So, when did you have your first interaction be it sexual, romantic, intimate with another person?
KELLY: Yeah. So, does that include kissing or are you just talking about hookup?
LEAH: Yeah, absolutely.
KELLY: So, my first kiss was at this girl’s house. I think she was actually my sister’s best friend. We had been in the same class together and I think we had a mutual crush. And we started dating and I started going over to her house to hang out.
And we were watching Chronicles of Riddick I think on her bed and she was lying with her hand on my chest. And when I went to leave for the night to head home, she kissed me on the patio. And then, the next time we hung out, we were just making out all the time.
LEAH: And what was that like for you?
KELLY: It was awesome. I love making out. I still do. I love especially with women to cuddle and kiss and hug and I also like the sex part. But for me, it’s like emotional connection. For my attraction to men as I’m realizing is I want to get railed like throw me on the bed daddy.
KELLY: Not that I’m saying that I couldn’t ever develop an emotional connection with a man, I’m not against that. I’m just saying it’s different. And also, I think I’m just unpacking a lot of the internalized homophobia and bi erasure that I learned from my peers and society and everything.
LEAH: Yeah. So, how old were you when you were making out with your sister’s best friend?
KELLY: Let’s see. It was high school, junior, senior year. So, I would have been 16, 17.
LEAH: Yeah. And did it stay at making out or did it progress any further?
KELLY: No, yeah. We pretty much just made out. I’m usually not someone to push things to the next step myself because I’m afraid of what if the other person doesn’t want to and I assumed or whatever. There were some I don’t know what base it is when you’re making out and I put my hand on her boob.
LEAH: Yeah. Under or over the shirt?
KELLY: I think it was over.
LEAH: Yeah. So, did you think of yourself as an attractive desirable person?
KELLY: Yeah. It was weird because, like I said, I disliked the way I looked. And back then, when I was 16, 17, it wasn’t that bad yet. I look back at some old pictures of myself from that age and I was a twink.
KELLY: I was cute. But like I said, as I got older, I think the dysphoria got worse.
LEAH: There are going to be people who don’t know what twink means. Can you describe it?
KELLY: So, twink is a term, I think it means thin, white, into no kink, is the acronym, but it’s basically a skinny feminine gay guy. Looking back at pictures from that age, I’m like, wow, I was a twink. So, yeah, I never thought of myself as ugly.
Women always told me I was attractive. But as I got older, that was more and more dissonant with the way I felt about myself. I know I’m attractive. Looking back now at pictures from a couple of years ago where I had a beard, I’m like, he’s hot. I’d do him.
KELLY: He’s hot in an awkward eggy way, but I definitely prefer the way I am now.
LEAH: Yeah. You made out with a girl in high school. What was the next big important interaction that you had with somebody?
KELLY: Yeah. So, the next was my freshman year in college. There was a girl that was in some of my classes who actually was the significant other that I was talking about earlier that I was with for a long time. And we just started hanging out. She was very curvy, was a big girl, which I like. I’ve always liked curvy gals.
LEAH: Say that again for the people in the back, please. There are people who love you no matter what size you are.
KELLY: I’m a big woman who loves big women.
LEAH: Thank you.
KELLY: Yeah, curvy girls rock. Yeah, so we started hanging out and I invite her over to watch movies. I think I asked her to come watch Spaceballs with me. And also, I’m showing her The Animatrix, but one time she was over, we just started making out. And then, she sucked my dick.
LEAH: Were you expecting that?
KELLY: No. And actually, the only reason we didn’t have sex was because I think it was her period. And I was on top in her mouth. Because it was my first time with another person, I actually came pretty quickly. And it was pretty cool. And then, we started having sex.
LEAH: Was that sexual relationship enjoyable for you? Did you have a lot of pleasure?
KELLY: Yeah, I did. I enjoyed it.
LEAH: Did you date more people in college?
KELLY: Yes and no. So, I did have a couple more crushes in college, but I didn’t actually end up having another girlfriend at the school. I did end up meeting a woman who was somewhat older than I am and ended up in a relationship with her that I did for a couple summers. And that was very instructive and enjoyable.
LEAH: In what way? When you say instructive?
KELLY: Just being with an older woman who really knows what she’s doing. Generally, actually, usually, I’ve been more attractive to women who are older than I am. I don’t really like younger women as much, but anyway, yeah, so she was blonde buck some MILF.
KELLY: Very sexy, very sex positive and knew what she wanted and she helped me. And I was good at sex and she told me that. And she helped me try things and do things I hadn’t done before.
LEAH: What kinds of things?
KELLY: So, she paddled me. So, I asked her to. And also, she pegged me once or twice. So, the first time I’ve been penetrated was by a ciswoman.
LEAH: Yeah. And did you enjoy that?
KELLY: At the time, I actually didn’t because it hurt. In general, I do because actually lot of times, on my own, I’ll masturbate that orifice myself with objects. But I think it was just I’ve actually had stomach problems like IBS I think due to food allergies for a lot of my life and that might be part of it because it’s easily irritated. And I didn’t know not to not eat certain things.
So, that was probably part of it. I actually had a lot of health issues back then that I wasn’t aware of. In general, I do enjoy that, but I think that particular time and she almost might have just been going a little too hard.
LEAH: Yeah. And the first time, I don’t know if you did any warm-up or gentle training where you start with something very small and then you get bigger, which is generally what someone in my position would suggest for anal play because that is an area of your body that if you’re not used to it being penetrated, you have to learn how to relax into it.
KELLY: Yes. You very much do. Yeah, I think we might have been using too big of a toy is what happened and not ramped up to it.
LEAH: Are you aching to explore new vistas of your sexuality? Do you hear me talk about concepts on this show and think, “It makes sense, but I need help applying it to my situation?” That’s where personalized sex and intimacy coaching comes in.
When you work with me, I promise to help you feel safe exploring your sexuality. Together, we’ll look at your needs and desires without judgment and help you figure out how to fulfill them. There’s no single answer that’s right for everyone. So, I’m going to help you discover what’s right for you. And we’ll go at your pace. That’s the pace that respects your emotional needs, your boundaries, and your nervous system. Because going too fast can send you into shutdown while going too slow can be infuriating. The goal is to find what’s right for you.
I work with clients who are motivated to explore many different areas of sexuality including things like expressing your sexual desires to current or future partners, exploring if you might be queer, challenging body image insecurity in sexual relationships, dipping your toes into BDSM or consensual non-monogamy, learning to date after a long time out of the dating pool, exploring sexuality for later in life virgins, and so much more.
I want you to have a deeply fulfilling intimate life. And together, we can help you get there. For more information and to schedule your free no obligation discovery call, visit www.leahcarey.com/coaching. That’s www.leahcarey.com/coaching.
LEAH: You mentioned paddling. Did you enjoy that?
KELLY: Yeah, I did.
LEAH: During these on and off summers relationship and any other relationships you might have been having, how were you feeling about your body and about yourself as a sexual being?
KELLY: I was enjoying it. I’ve always liked sex and that also was maybe why I took so long because I’m like, I really enjoy having sex with women. I really enjoy pussy. I enjoy eating pussy. So, I’m like, I’ll probably have sex with a guy if the situation arose, but I’m mostly attracted to women, so why bother coming out as bi?
But where I felt like a sexual being, yeah, I felt sexy. Actually, there were some times where I didn’t feel sexy and this is actually the opposite. How do I say this without misgendering myself? Because obviously, I didn’t know I was a transwoman back then. So, let’s just say this is the opposite problem that I think a lot of guys have, which was for a while in 2011, we realized later that I had a hormonal problem with my thyroid, which is probably why I sometimes couldn’t cum. I just couldn’t get there. I could go for an hour or more. It felt good, but I just wouldn’t get there.
LEAH: Was it frustrating?
KELLY: Yes. It was frustrating. And the thing is it was also very frustrating for her and I think it made her feel like she wasn’t attractive. And I was just like, “No, you’re really attractive. I’m really attracted to you. I don’t know why I can’t. We’re having a good time. It doesn’t bother me.” But I felt like I was shamed for it.
And so, honestly, ever since then, I definitely have enjoyed intercourse since then, but I always in the back of my mind am like, okay, am I going to cum? Am I cumming too fast? Am I cumming too slow? I need to make sure I cum, but don’t cum too quickly. It’s like this knife edge balance. It’s exhausting.
LEAH: Yeah, it is. And it is very common for ciswomen to live on that knife’s edge.
LEAH: Yeah, definitely. Yeah, interesting. So, are there other major relationships or sexual experiences that we should talk about before we start talking about transition?
KELLY: One that’s important because it’s with the best friend I mentioned who we’re dating for a couple years before. We broke up, but kept hanging out and together, and then she’s the one that I came out to as trans.
A couple weeks ago, I was feeling frustrated and just really, I don’t know, needed a release, needed some stress release. So, I installed Grindr and just uploaded some photos and put bi transwoman looking for older daddy, DTF. And I was flattered by immediately how many guys wanted to fuck me.
And so, I actually didn’t do it that same weekend because I was busy. But then, the next weekend, I opened Grindr again and this hot guy had sent me some pics of myself. And I was like, “Hey, do you want to fuck?” And he’s like, “Yeah.” “And just to clarify so you know, I’m a transwoman on HRT about 6 months and no surgeries. Is that OK?” And he’s like, “Yeah, that’s fine.” And I’m like, “Okay, you want to meet at this coffee shop?” And he’s like, “Yeah.” And so, I did. I met him there. I felt bad because I was running a little bit late because I wore heels for the first time. And I walked over there and it took longer than I thought.
KELLY: But I got there and because I felt bad, I’m like, “Hey, do you want to just get out of here?” And so, we just took the bus back to my apartment. And we had sex. I sucked his dick and I realized that I think I like sucking dick as much as like eating pussy. I like them both, but I was surprised by how much I enjoyed it.
And he fucked me. It hurt a little, but I was learning to relax and I enjoyed it. Girl, I came 5 times. And that’s the thing now on the HRT, I can have multiple orgasms and I don’t necessarily ejaculate every time that I have an orgasm, which is really cool. I love what it’s done for my sexuality and my pleasure. It’s amazing.
LEAH: So, I’m curious in terms of orgasm, I think that many people associate a cis male’s orgasm with ejaculation. People think that those two things are so intertwined that they are the same thing, which is not necessarily true. But when you say that are now capable of multiple orgasms, but you don’t necessarily ejaculate, what does an orgasm feel like to you?
KELLY: It’s much more full body. It’s like shivers through my body. And I think I get the best orgasms from the butt from stimulating. I have a vibrating butt plug that I love, but also yeah, I’m realizing I’m a total bottom.
KELLY: And I’m bisexual, but I’ve been in a relationship with a ciswoman for most of the last 10 years. So, I’m into guys now. Again, I think it’s the bi cycle. I’m sure I’ll cycle back and I definitely still find women very attractive, but I’m now making up for lost time. Not that it needs to even out or anything.
KELLY: I’m still bi, no matter who I’m with.
LEAH: So, do you find that there is a significant dating pool for you as a transwoman whether it’s with ciswomen, cismen, other trans people, non-binary people? Do you have a fairly active dating life?
KELLY: Yes. So, I’ve been in a relationship for most of the last decade, not the same relationship the whole time, but although one was for 7 years. So, I’m at a point where I don’t want to be in anything serious for at least a few years. So, I’m not dating dating. And also, I’m in grad school. So, I’m too busy for a relationship. I just don’t have the energy to worry about someone else.
And unfortunately, that is something that I do whether asked or not and it’s not putting on the other person because it’s something I do. But I tend to be a caretaker. And I don’t have the energy to worry about someone else’s life. Not to sound like a bitch or anything, but it’s just true. I just don’t. I have health issues and it takes all my energy just to take care of myself and be healthy and try to get my work done.
LEAH: Yeah. But you can still date if you’re not looking for a relationship.
KELLY: Yes, I can.
LEAH: So, are you dating? And I know that you’re having sex because you’re on Grindr.
KELLY: Yeah. I don’t have it currently installed, but when I feel the itch again, I will definitely reinstall it. Clearly, there’s lots of guys on Grindr that want to have sex with a transwoman, which I wasn’t sure because I hears it was like the gay dating app, but I didn’t know if it was just gay men or what, but there’s a lot of transwoman on the app too. I haven’t seen any transmen, but I don’t know. But I would assume so. And the thing is I think I like queer men. I like bi and pan men. So, obviously, I wouldn’t expect a strictly monosexual gay man to be attracted to me. And if he were, it would make me feel dysphoric.
LEAH: Interesting, yeah.
KELLY: Yeah, I’ll be whatever you want.
KELLY: But I’m also a little bit afraid to date straight guys because I’m a little bit worried about will they be ashamed to be with me if we get seen? Will they try to hurt me? I’m pretty big still. I’m large. I’m tall. So, I think I can defend myself, but also, I’ve definitely lost some strength since starting HRT.
So, I don’t want to put myself in a situation where someone was trying to hurt me who’s probably stronger than me. And again, not to knock straight guys because I’m not saying all straight guys are like that, I’m just a little bit nervous.
LEAH: Yeah, absolutely. So, let’s go back and talk about the actual transition. Is it okay if I ask you some personal questions about the transition?
KELLY: Yeah, anything.
LEAH: Okay. When did you start hormones?
KELLY: So, I started spironolactone which is a testosterone blocker last August, and then I started estradiol which is a form of estrogen within a month, so September.
LEAH: And that’s what you refer to as HRT?
KELLY: Yes, HRT is an acronym for hormone replacement therapy. So, in transwomen, that’s taking a testosterone blocker and estrogen, and then also, sometimes nowadays later progesterone, which I am hoping to start sometime this year. My doctor says that you get the best breast growth results if you start that about a year after starting HRT.
LEAH: Okay. So, part of the reason I’m so excited to talk with you is that all of the other trans people I’ve spoken with have been further into their transition like many years into their transition. So, I’m really excited to hear you, what’s your experience as this is all developing.
KELLY: I’m still a baby tranny.
LEAH: So, what kinds of changes are you seeing in your body, but also in your brain and how you interact with the world?
KELLY: So, yeah, I love to talk about this. So, the mental and emotional changes were very, very soon. So, after I started the spironolactone, again, that was just by itself for a month before I started estradiol. And the first obviously couple days didn’t feel super different. And then, maybe 2 weeks in, there were a few days where I suddenly had no willpower, no motivation. And that sucked, but I got through that.
And then, I felt a sense of calm and peace that I hadn’t felt in as long as I could remember. I realized that the way I used to be with just testosterone coursing through my body every single day was just a struggle just to exist. It hurt and it just took energy and effort just to get up out of bed and just go through the day. And that was gone. And it’s such a huge lift off of my shoulders.
And then, the estrogen, I was able to actually access my emotions and feel them much more than I ever had before. And I’ve cried more in the last 6-8 months than I had in my entire life and it’s good. I feel like I’ve worked through so much, so many things because of it.
KELLY: Because it’s actually being able to feel my emotions and I can cry much more easily now and it’s wonderful. It’s great. For the physical changes, there’s what I mentioned before with the way it’s changed my orgasm and the way I experience pleasure.
Before when I wasn’t on HRT, pleasure was much more located in the penis. When I orgasm, it’s very much there. But now, it’s full body. And actually, I remember the time my best friend, we used to date, the one that I came out to last year, we broke up a few times, but then we kept hanging out. And I remember the time that it was after I started hormones, we still had sex a couple times every month or so.
And I remember the second or third time after starting HRT, we did it and I was like, this feels different. I feel like I’m having sex as a woman. It’s such a different feeling in my body. It’s all throughout my body and I feel this emotional connection. Obviously, I always felt emotional. I’m not saying I was this emotionless robot before.
And also, it’s not to reinforce stereotypes like guys don’t have emotions or women are too emotional because I’ve read testimonies from trans guys that I’m mutuals with on Twitter that say that they couldn’t cry until they started testosterone, and then they were able to. So, it’s not about women cry and men don’t. It’s like having the wrong hormones in your body makes it very difficult to be a whole person and feel your emotions. Yeah, trans people just are people whose bodies make the wrong hormones.
LEAH: Yeah. Since you began the HRT, when you have sex, it feels like you’re having sex as a woman, do you still use your girl dick to penetrate people?
KELLY: Yeah. When I say I feel like I was having sex as a woman, it felt more like I’m describing the way I felt in my body, the way I felt emotionally. But yeah, because it’s what she likes. I like it too. It feels good.
LEAH: Can you still get hard?
KELLY: Yes, but it’s not nearly as often. And it’s actually a relief because it used to be it’s like every day sometimes or every other day, depending on what meds I’m on and stuff. But I used to have to jack off every afternoon and it’s exhausting. And now, when I do feel that, when I get horny, it’s like this is a treat. This is a pleasant surprise, not a chore. I’m like, I’m horny. Sometimes, if I’m lazy, I will just still jerk off, but it feels different.
LEAH: So, when you masturbate now, how do you masturbate?
KELLY: Like is aid, if I’m too tired, I will just jerk off, but it’s different. The way I move, it’s almost like I’m playing with a really big clit. And I’ll touch my thigh and feel my breasts. And, like I said, it’s my whole body is an erogenous zone now instead of just a small part of it.
But also, if I’m really feeling it and especially, I was doing this a lot before I got the courage to go on Grindr and hook up with a guy, when I was really feeling it, I would use my toy, my vibrating butt plug and fuck myself with it. That would give me really good orgasms, the sensation.
And also, the type of porn I watched and the way enjoyed it was different. I started imagining myself as the girl in a lot of them and also looking for videos with transwomen having sex with cismen and getting railed and I want that.
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LEAH: Since you’ve begun the hormones, it sounds like you’ve developed a little bit of breast tissue and it sounds like you want more.
KELLY: Yes, I do. I want to be someone’s big titty goth girlfriend, if I’m honest.
LEAH: Okay. So, what’s your goal? That’s your goal, but do you have a size or a shape that you want to get to?
KELLY: Okay. So, this might be a little unrealistic, but honestly, I wouldn’t mind being Amy Villainous, it’s a goth model figure. But I would love to have really big tits, so it’s to say I want to get a D cup. I don’t need to have them bigger than that, but it’d be cool if I had a D cup. It helps that I am larger and I’m heavy and I had a B cup before I started hormones.
So, actually, my bestie measured me, I was a 52B. I haven’t checked lately. I don’t know if I’ve grown. I’ve definitely grown, but I don’t know if it’s a different cup size. So, I’m fully out everywhere now. And I love wearing dresses. Sometimes, I wear jeans. My whole wardrobe is pretty much women’s clothes at this point, but obviously, I have some women’s jeans, women’s pants that I wear to work sometimes. But I really love wearing dresses. And I wear dresses to work now. I get up and do my makeup. It’s awesome.
But when I put on a bra and I have some bras that have some pads in them, they’re not ridiculous but just a little bit of padding, and if I put one of those on in a dress, I have tits. I think people can clearly see that I have tits now and I love it. It’s great.
LEAH: Yeah, that’s awesome. I’m happy for you. Do you want to get top surgery at some point or do you want to grow naturally?
KELLY: I am debating because when I first realized I was trans and decided to try hormones and then I was like, all I really want is hormones. I don’t really need surgery or anything like that. But now, I’m like I’m curious how they grow without since I did start off bigger and they seem to be evolving nicely. I’m curious how they grow naturally, but I recently found out that my insurance does cover top and bottom surgery. So, I’m like maybe I should jump on that while I can.
LEAH: No kidding. That’s a pretty big decision to make under the gun.
KELLY: Yeah, it is
LEAH: Yeah. So, what are your thoughts about bottom surgery?
KELLY: So, I have always thought that women with dicks are beautiful ever since I was young looking at stuff online. In fact, actually one time, I do remember I was walking home from school and I was talking to a couple of my friends who were guys and it was like we were talking about porn or something. I think I told one of my guy friends that I thought shemales were hot. I didn’t know at the time, yeah.
LEAH: It was a different world. We didn’t know, yeah.
KELLY: Yeah. And so, they looked at me and they were like, “Dude, what the fuck?”
KELLY: And I never really talked about that with guys ever again. Now, I’m the hot tranny that everyone wants to fuck.
KELLY: But I think part of why I didn’t necessarily put together that I was trans for a long time was because the way it’s presented so much in pop culture, a lot of sitcoms have an episode where an old friend would be back in town and they’re the opposite sex now. And the way I got this idea from pop culture, you just go and have an operation. This person had a sex operation. And now, they’re the other gender.
And I’m squeamish. I never liked operations or going to the hospital or surgeries. And so, that squicked me out when I was younger. And some of that was definitely for sure internalized transphobia that I need to work through. But I was like I don’t know. I like my penis. I don’t want it to get chopped off. It’s not how it works. They don’t just chop it off. That’s what I thought.
So, part of what allowed me to explore my gender was, first of all, thinking of myself as non-binary and just being able to not be a man. That was the amazing first step. That was just setting down a huge boulder, a huge weight, but also realizing that transition isn’t this one and done procedure that you just go and do. It’s this long act of creating yourself and it’s open-ended.
There’s no one thing you have to do. I love putting go makeup and wearing dresses and I’m growing my hair out long. I dyed my hair pink actually. And I love that, but some people just wear the same thing they always have. What I think is really cool is there’s lots of butch lesbian transwomen and effeminate gay trans guys, very cool. And when I first realized I was trans, I’m like, I guess I’m a translesbian. And now, I’m like, I’m just bi. You can be both. I’m not placing anyone’s identity, but I feel more bisexual. Again, my newfound appreciation for men.
LEAH: Yeah. And what about other things? Do you want to get voice training at some point?
KELLY: Yes. My two, I think, biggest sources of dysphoria are my stubble, my face and neck hair, and my voice. And I can do this nice high femme voice a little bit, but I can’t keep it up for a long period of time. It makes my throat tired. It’s hard to do early in the mornings or late at night.
I had an experience I think the weekend before I had sex with that guy from Grindr. I was out running some errands and I was at a Target. At work, I used the gender-neutral restroom because I’m not ready to bump into someone who knew me before. But when I’m out and about and it might have had to do with the fact that someone called me ma’am earlier that day when I was at Whole Foods, so I had to pee.
I was in Target. I’m like, you know what? I’m just going to use the women’s restroom. And so, I did and I went and sat down to pee. And I hung my coat up and I had my umbrella in my coat. And so, I peed. And then, I got back up. And I was putting my coat on and my umbrella clacked against the other stall. And the woman in the other stall was like, “Is someone knocking?” And I just tried to be quiet, but she kept asking. And I was like, “I’m sorry. It was my umbrella.” And she’s like, “What?”
But I think she was hard hearing or something, but I didn’t want to keep talking because I didn’t want her to go like, “Oh my god, there’s a man next to me.” And so, I just washed my hands and left. And I used to have this big man coat, but now I have a women’s coat, which I think helps a lot. But when I’m wearing a coat and especially I have a hat on, people could just see my eyes if I have mascara on and eyeshadow and makeup, people just see a tall woman.
And again, if I don’t say anything or if I use my high voice, then I think I do pass better than I think I do. I think most trans people pass better than they think they do because I actually have noticed a few times now men have let me go ahead of them in line at the grocery store and one man moved over and offered me his seat on the bus. I think I pass better than I thought I did or they’re just being polite, which either way, it’s fine.
LEAH: Yeah. Is passing an important thing to you?
KELLY: It depends on the situation. Because personally, I’m very much proud to be queer. My hair’s pink.
KELLY: Part of me is aggressively like, I’m here, I’m queer, deal with it. But definitely, there are situations. I don’t like everywhere I go just people looking at me, look at the tranny. And I’m aware that I have a much higher likelihood of getting hate crime now. So, yeah, and I think especially for transfeminine people, it’s a safety issue. So, I would like to be able to pass if I so desire. Let’s put it as that. But in terms of my politics, no, I’m full liberation, not assimilation.
LEAH: Love it.
KELLY: But yeah, as a practical matter, passing or at least being able to is important.
LEAH: I have heard a narrative that says the pandemic was actually great for people who were discovering their trans identity, but I haven’t really talked to anybody personally. So, can you tell me what it was like for you having this whole awakening during a time when everybody was shut in their homes?
KELLY: Yeah, that was me. I had this feeling in 2020 actually that I needed to just spend time with myself because I had been in relationships for most of the last decade. And I’m like, I need to reconnect with myself. I pretty quickly in 2021 started playing around with my gender and presentation. I started playing Stardew Valley again and put the name Kelly and chose a female avatar.
So, what’s actually funny how I chose the name Kelly, it was actually my nickname when I was little. The boys in my class started making fun of me for it because they said it was a girl’s name. And what’s funny is for years and years, I had to ask my relatives, pretty much my mom’s side of my family but not inclusively, but mostly my mom’s side of the family to stop calling me <redacted>, dead name, my full name.
LEAH: Is that okay with you to have your dead name on this podcast?
KELLY: I don’t love hearing it.
LEAH: Okay. I’ll take it out.
KELLY: Sometimes, I use it when referring to him. I do think of him as an aspect of myself like a shell or pseudonym that I created. So, when I am personally thinking of him, I do use the pronouns him, but I don’t like when other people say that name. I’d rather they just don’t.
LEAH: So, you were talking about asking family to not use.
KELLY: Yeah. So, for years, I was asking my mom’s side of the family to stop calling me Kelly because again, that was associated with being bulled and trauma and stuff. And then, I remember thinking wouldn’t it be hilarious if it turned out I was trans and I started going by Kelly again and I had to ask them to start calling me Kelly again? Wouldn’t that be funny? Wouldn’t that be cool? Maybe I should just do that as a prank. That’d be fun.
KELLY: The thing that blew my mind was figuring out that wanting to be trans is the same thing as being trans. Like I said, going back, there were signs and there were times. Actually, I remember when I was real little when I was in 1st, 2nd grade, elementary school or something, thinking, how cool would it if I could be a girl for a weekend and just stay in bed and play with your boobs all weekend? I thought that was typical cis boy thoughts. Boys like boobs. So, who wouldn’t want to have their own boobs? Apparently, cis straight guys don’t want to be girls. It sounds sus to me, but anyway, yeah.
LEAH: You mentioned talking to your family about your name change. What was it like for you coming out to your family as trans?
KELLY: Yeah. I wasn’t too worried. I didn’t think they would disown me or anything. There was a funny misunderstanding though because I had told my mom that I was nonbinary and I was explaining to her what that meant. And I also told my dad that and what’s funny is he told me he’s always felt like he’s a lesbian in a man’s body.
LEAH: Really? Wow.
KELLY: I don’t want to have that conversation with him.
KELLY: And I was explaining to them what that meant too and they were both like, “We love you. We just want you to be happy, whatever that means.” But then that I really fully decided to make this conscious decision like, okay, I’m nonbinary. I’m not a man. I want to explore and find out how I want to present, where my gender lies on the spectrum. So, I ordered some women’s clothes. I ordered a green dress and a denim jacket. It’s an ugly dress now, but it was my first dress.
LEAH: Yeah, it’s a big deal.
KELLY: And I had this denim jacket. It’s a little bit gay looking. I love it. It’s cool. It’s a women’s jacket. And yeah, so I was wearing those and I ordered some panties, some underwear. And I just started wearing clothes like wearing that in my own apartment. And I started watching a lot of trans Youtubers and going like, wow, this actually makes a lot of sense what they’re saying and I relate to this a lot.
And so, then that weekend, so this was the 21st I think of May last year, I went over to my friend’s, my bestie’s, condo and I had told her that I was non-binary a couple of months earlier. And she told me she actually didn’t feel like I was a straight guy from the beginning. And I’m like, “You’re very intuitive.” Fun fact, in 2019, we had been Snapchatting each other and I was playing around with a gender filter on Snapchat and I took some selfies of me as a woman and I’m like, “I’m pretty cute as a girl.”
KELLY: And I actually used it to take a picture of her, but as a man. And I’m like, “You’re hot actually as a guy. You’re hot as a woman too, but I’m saying you’re hot either way.”
KELLY: And that’s what I mean when it’s hard to say when you realize you’re trans because so much of it is unconscious at least for me. But yeah, so I was like, am I really going to come out to her? What’s she going to say? I thought she’d be cool because a lot of her friends were gay. She’s very accepting. But it was still nerve-wracking.
And so, I said, “Hey, I want to show you something. I’ll be right back up.” And I put on my dress and my jacket and some tortoiseshell glasses that I think I borrowed from her. And my hair was super short because I had just buzzed it because it was like really hot that summer. And it might also have been an unconscious last act of denial. So, I looked for a butch, actually looking back on it, which is cool. But I definitely do prefer having longer hair now.
But I put on my dress and my jacket and I went back upstairs and I walked over to her. And she looked at me and I said, “I’m trans.” And I just hugged her and I started crying. And she was like, “It’s okay.” And she gave me some wigs to try on. She let me keep some. She let me try on some of her clothes, her nightgowns. And I put on the wigs and I felt so happy as a woman. It felt incredible. And she was just so wonderful. She’s been there for me and I love her so much and she’s my best friend in the world.
LEAH: That’s amazing, yeah. Awesome. I want to transition us to the Q&A, which is going to be fairly short because a lot of these don’t actually apply to you. I just said that very inelegantly. It’s not that they don’t apply to you.
KELLY: I didn’t take offense. Don’t worry. I assume you mean they’re later transition questions?
LEAH: No, they’re about people who have vaginas.
KELLY: Yeah, no, that’s not me. Not yet anyway.
LEAH: Okay. All right. But I’ll ask you the ones that do.
LEAH: And now, it’s time for the lowdown, the things we’re dying to know, but would usually be too polite to ask any good girl.
LEAH: What’s the approximate number of sex partners you’ve had?
LEAH: What’s your favorite sex toy?
KELLY: Definitely my vibrating butt plug.
LEAH: What’s your favorite sex position?
KELLY: So, okay, I have two. When I was living as a man and when I was giving, I always liked I’m up on my knees like up straight and I’m topping and she’s letting me enter her like missionary. But then, I fold her legs over, so it’s like sideways or put one leg up on my shoulder. That, I’ve always really enjoyed. Although I also like being on the bottom like having her ride. That feels good too. But I got to say having a man put my ankles on his shoulders and pound me missionary was fucking great.
KELLY: So, that’s definitely up there. I think it’s too recent for me to rank it up objectively.
LEAH: Yeah, but it’s a current favorite.
KELLY: But I enjoyed that.
LEAH: Excellent. I’m glad.
KELLY: Like I said, I am on a dude’s rock kick right now.
LEAH: Yeah, all right. What’s your favorite thing to do to your partner during sex play?
KELLY: I love pleasing my partner. I love oral. I’ve eaten pussy a lot in my life. I also love analingus. I eat ass. I enjoy that. And I recently discovered I really enjoy sucking dick too. And also, I like to give massages. I like to put lotion on and rub my partner’s back and really get that tension out. Yeah, I know it’s a million answers, you asked for favorite, so yeah.
LEAH: No, that’s okay. That’s great. What kind of touch do you enjoy receiving the most? And also, I recognize that this may be changing because your hormones are changing.
KELLY: Yes, it is definitely changing because, yeah, hormones definitely they affect the way that I feel pleasure and the way I get horny. And I think definitely, they also are affecting my preferences and orientation a little bit. I’ve always been bisexual. They haven’t changed my orientation, but I do feel more attracted to men now.
And some of that is working through internalized homophobia. Some of it is definitely the estrogen because I used to be attracted to women and femme guys like femme boys. Now, I like manly men. I like beards. I want a daddy, someone who’s going to take charge.
LEAH: Yeah. What’s your favorite part of your body?
KELLY: I would have to say probably my tits and my legs. I love my tits because I’ve always wanted tits and I realized as soon as I’m going to go on hormones and I’m really excited about this, my number one thing that I wanted was I wanted my breasts to grow bigger. I wanted boobs.
Because for me, I don’t know, that’s just always been something that I appreciate about women. And so, it’s something that I associate being a woman and I just want to have. I think having breasts makes people at least not immediately assume that I’m a man.
LEAH: Yeah, sure. What is something about your current sex life that isn’t quite as satisfying as you’d like it to be?
KELLY: It would be nice to just be able to get railed on demand without having to be like, okay, is this guy going to hurt me? Where should I meet? And it would be cool to just be able to have the guy come over, but I’m going to meet in a public place first. Especially as a transwoman, I have to be careful. I have to be aware. And also, just I’m tired doing grad school and some of my health issues. And I think the estrogen too makes me sleepy. So, a lot of times, I’m horny, but I’m more sleepy, so I’m just going to go to bed.
LEAH: I think there are a lot of people who can relate to that.
LEAH: What belief did you have about sex as a child or teenager that you wish you could go back and correct yourself on now?
KELLY: If I could go back and tell myself, “Hey, idiot. You’re a girl,” I would do that. But yeah, I guess actually maybe because I definitely absorb some harmful ideas about transwomen from my peers. And a lot of this stuff is coming back to me now, but I remember in I think elementary school, I don’t know where these other kids were hearing this stuff, and also in middle school, some of my male classmates telling me some really vicious things about transwomen.
They didn’t use that word, but I remember one kid told me that there were some gay men who cut their dicks off in order to look like a woman and lure little boys. And that fucked me up for a long time. And also, stuff like Mrs. Garrison on South Park and Family Guy had some jokes. Transwomen are the butt of so many jokes in pop culture, in movies like Ace Ventura. It’s the punchline, yeah. So, you absorb that. But yeah, I think I would just erase all the harmful stereotypes and lies that I absorbed from society about people like me.
LEAH: Yeah. I hope that we can do better by the next generation, yeah.
KELLY: Yes, I hope so.
LEAH: Kelly, thank you so much for having this conversation with me. It’s been amazing.
KELLY: I’ve really enjoyed it. Thank you.
LEAH: That’s it for today. Before we go, I want to remind you that the things you may heard about your sexuality aren’t true. You are worthy. You are desirable. You are not broken. As a sex and intimacy coach, I will guide you in embracing the sexuality that is innately yours, no matter what it looks like. To set up your free discovery call, go to www.leahcarey.com/coaching.
If you have questions or comments about anything you’ve heard on the show, call and leave a message at 720-GOOD-SEX. Full show notes and transcripts for this episode are at www.goodgirlstalk.com. And you can follow me @goodgirlstalk on the socials for more sex positive content. If you’re enjoying this show, please take a moment to leave a 5-star rating and review on Apple Podcasts or if you’re using another podcast app, go to www.ratethispodcast.com/goodgirls.
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