OVERVIEW:
What does it mean to bear witness to pleasure? In this episode, I sit down with Sister T’Aint A Virgin from the legendary Sisters of Perpetual Indulgence. From the radical origins of the Sisters’ activism during the AIDS epidemic to their modern mission of expiating shame and spreading joy, we explore how witnessing sex can be transformative, educational, and liberating.
Sister T’Aint A Virgin shares her journey from curious voyeur to symbiosexual, finding profound meaning in observing the intimacy of others and embracing the diversity of queer bodies and sexualities. Along the way, she opens up about navigating consent, cultivating intergenerational mentorship, and her most adventurous sexual experiences. Whether you’ve ever been curious about watching, engaging, or just learning from the beauty of connection, this episode invites you to reconsider how bearing witness can enrich your own sexual liberation.
TRANSCRIPT:
Trevor Hoppe (00:09)
Hey, welcome to the best gay sex podcast. I’m your host, Dr. Trevor Hoppe. Today’s episode is about bearing witness. Now I know the word witness probably conjures up images of someone testifying in a court of law, but today we’re talking about the radical pleasure of watching. Witnessing sex can be transformative, not just for the person that’s doing the watching, but
also for those who are being watched. And that’s because the act itself shatters all that stigma and shame that tells us as queer men to keep our sex behind closed doors, out of sight, out of mind. And for today’s guests, witnessing can also be a form of sex education. Sister Tana Virgin is a member of the Sisters of Perpetual Indulgence.
nonprofit group of queer nuns that began in San Francisco all the way back in 1979. And you may recognize their kind of campy irreverent style with those nun habits that you’ll see if you’re watching the episode. They work to quote promulgate universal joy and expiate stigmatic guilt. Through their ministry of presence, community service,
and groundbreaking efforts like creating the first ever safer sex pamphlet targeting gay men. The sisters have become icons globally when it comes to queer activism and sex positivity. In this episode, Sister Tana Virgin explains how watching has shaped her understanding of pleasure, connection, and queer liberation. Let’s listen in.
Trevor Hoppe (02:00)
Sister T’Aint A Virgin, welcome to the Best Gay Sex Podcast.
Sister T’aint A Virgin (02:04)
Hello
Trevor Hoppe (02:04)
It’s a pleasure to have you, and tell listeners and viewers a little bit about the Sisters of Perpetual Indulgence because they’re going to be looking at you and some will be familiar but some won’t be, so let’s just start there.
Sister T’aint A Virgin (02:11)
Yeah, of course.
course.
Great. Yeah. So this is sort of perpetual indulgence as a nonprofit organization that started here in San Francisco in 1979. We just celebrated our 45th anniversary. As sisters, we take vows to the community to promulgate universal joy and to expiate stigmatic guilt. We do that through various forms of community service, social fundraising, engagement with the community.
Trevor Hoppe (02:29)
awesome.
Sister T’aint A Virgin (02:45)
Our main thing is our ministry of presence, which is just kind of putting on these fabulous habits and then going out into the community and kind of being ministers within the community. We’re non-denominational and each sister kind of has their own ministry that they feel called to do, that we also kind of interlap in a lot of different ways.
Trevor Hoppe (03:08)
And there’s kind of a sex-positive origin story to that, right?
Sister T’aint A Virgin (03:11)
Yes, absolutely. The sisters, again, kind of founded and really rallied together, primarily as initially some gay men who were kind of tired with the fact that the government really wasn’t stepping up in any capacity for the early stages of the AIDS epidemic. And so we kind of started helping ourselves out and we did that through our kind of social activism.
Trevor Hoppe (03:33)
you
Sister T’aint A Virgin (03:40)
The Sisters put together the first ever Safer Sex pamphlet that was really tailored towards gay men, that was meant in a sense that was more positive and pleasure focused, while also providing kind of important health information. We call that Playfair. And then we’ve kind of done other kind of fundraising efforts throughout the decades, largely related to AIDS organizations, but we’ve now kind of expanded into all forms of sex positivity.
Trevor Hoppe (04:10)
I love that. And how long have you been a member of the Sisters?
Sister T’aint A Virgin (04:14)
I’ve been a member for about 14 years now. Yeah, I initially joined back in 2010 and became fully professed in 2011.
Trevor Hoppe (04:25)
Professed: I assume that’s the initiation word, right? You become Professed is that right? Yeah. Fabulous.
Sister T’aint A Virgin (04:28)
Yes, exactly. Yes, we have a very rigorous initiation
process. And then you become fully professed after kind of demonstrating your commitment to the community at large.
Trevor Hoppe (04:39)
I love that. remember living in San Francisco doing the Easter celebrations and the sisters would always be there. And I think it plays on this, obviously, the religious overtones, but what’s so fabulous about it is that it’s so campy and over the top and sexy. I mean, a lot of times it can be quite sexy. I love that.
Sister T’aint A Virgin (04:56)
Yeah. yeah. Yeah. I mean, so Easter
is our anniversary. it’s the first day that, four sisters put on habits and kind of went out to the street. they had done other forms of street theater up until that point. it was really kind of these numbs habits that really polarized the community in a way that kind of got people excited. And I think a lot of that’s going back to kind of some forms of religious trauma, or just religious affinity. but again, kind of.
Trevor Hoppe (05:18)
Mm-hmm.
Sister T’aint A Virgin (05:25)
tailoring it and filtering it through this lens of kind of being the holy fool and bringing in kind of tongue and cheekness. But Easter is our claim to fame. We host the Hunky G this and the Foxy Mary contest as well. And we encourage people to be as fun and creative and sexy and flirtatious as they want to be. And it’s always fun seeing what people interpret that to be in again, a very kind of positive and affirming way.
Trevor Hoppe (05:30)
Mm-hmm.
That’s fabulous.
I love that so much. And did you grow up in a religious household? You mentioned trauma. I’m just curious.
Sister T’aint A Virgin (06:00)
No. Yeah.
My dad’s side of the family is Jewish. My mom’s side of the family was more Protestant, but it was never an issue within me growing up. Neither of my parents were super religious. My mom was more spiritual, and so I was able to dabble around and figure out what it is that excited me. And I’ve always had an affinity for
kind of the structure and the ritual related to a lot of kind of organized religion, but specifically the dogma and a lot of the kind of shame based approach is never something that’s resonated with me. And seeing growing up being gay and seeing kind of a lot of my peers and kind of generations ahead of me who are kind of processing a lot of that. I knew that this was something that I could do that kind of helps reclaim
a way that kind of feels holistic and loving and joyful and pleasure-based.
Trevor Hoppe (07:06)
How did you first encounter the sisters?
Sister T’aint A Virgin (07:10)
I think I first encountered them at Easter. Again, not really even knowing that it was their actual gig, but it was just kind of Easter in the park. Everyone goes, you go for the contests. But it wasn’t until several years later that I met a sister outside of habit at the work-based training that both of us were going to called the San Francisco Sex Information.
Trevor Hoppe (07:36)
and sleep.
Sister T’aint A Virgin (07:36)
which was
kind of tailored towards sex educators to be better sex educators and be able to sit on talk on phone lines and chats in order to answer questions. And so we kind of instantly clicked because we were just these two kind of queer weirdos within this sea of already fabulous queer people. But we just instantly meshed. so at that time,
they were explaining kind of what they were going through, because they were one of a few sisters that went and took communion at one of the Catholic churches here in the city in habit. And that got national attention. And so they were in the process of processing that. And so it was fun kind of being on the reflexive end of that and just holding space for a sister to be able to kind of have their own form of a confessional instead of the sister hearing the confessional.
Trevor Hoppe (08:08)
Mm-hmm.
I bet.
Sister T’aint A Virgin (08:34)
which is usually what we do throughout their community.
Trevor Hoppe (08:37)
Mm-hmm. And before the sisters, where did you grow up? Situate me in that, because you’re in San Francisco now. Are you from there?
Sister T’aint A Virgin (08:43)
Yeah.
From the Bay Area, I grew up down on the peninsula and then went to undergrad down in Santa Cruz and then immediately moved up to San Francisco after that. My undergrad degree was in something called Community Studies, which was unique to our campus, but it allowed you to kind of go into a pre-determined kind of community at large, working with a nonprofit. He did a
six month full-time internship and you pretty much audited that organization to see if they were kind of truly meeting the needs of their mission statement as well as kind of the community that they were focused to serve. And so my focus was on sex, gender and sexuality. And I came up to San Francisco to intern with the center for sex and culture with Dr. Carol Queen and Robert Lawrence. Yes. Yeah. And so,
Trevor Hoppe (09:26)
Mm-hmm.
with Carol Queen. I love her.
Sister T’aint A Virgin (09:40)
It was like immediately new to the city and immediately diving into like kind of the wealth of different sexual communities here in San Francisco. And it was amazing experience to really kind of see and be exposed to a lot of different communities that I hadn’t already been part of. As much of my personal experience was largely kind of in the gay male experience and the center for sex and culture was everything. And so it was lovely to kind of get that exposure.
Trevor Hoppe (10:05)
Mm-hmm, you ran the gamut. Yeah.
Sister T’aint A Virgin (10:09)
and kind of learn the ins and outs of San Francisco sexuality.
Trevor Hoppe (10:14)
Yeah, there’s really no place like it in the United States, at least, when it comes to sex. It’s kind of the hub of so much cultural, political activism when it comes to sex. What was it like growing up in that environment? As a queer person, it must be like a treasure trove.
Sister T’aint A Virgin (10:20)
Right?
You know, you would think so. I think as soon as you get outside of San Francisco and kind of down on the peninsula, I think the general pulse is still more liberal than not. growing up, it was kind of in the suburbs and it was definitely much more of a kind of quasi conservative. I grew up in the kind of late 80s, early 90s and didn’t really hit my sexual maturity until kind of the early 2000s.
and my uncle, passed away about a few months before I was born from AIDS related complications. And he was my mom’s best friend and she was super supportive and loved the fact that he was out and gay and lived in San Francisco for long periods of time. But the kind of trauma of losing her brother in such a kind of traumatic way, definitely kind of filtered down to my experience growing up and kind of feeling like.
Trevor Hoppe (11:07)
god.
Sister T’aint A Virgin (11:29)
being gay meant you were going to get HIV, meaning you’re going to kind of die from AIDS related complications. And even though I was maturing at a time where we had kind of medications and like it was no longer seen as this death sentence, there was still kind of generations of kind of personal trauma that was happening there that I still had to kind of navigate, which I think kind of turned me off to wanting to be explicitly sexual in a lot of ways.
I turned that into wanting to learn everything I could about it. And so that’s what kind of drove me to being more of an activist and being more of a sex educator was really to kind of like take control of this so that I felt more comfortable kind of navigating it myself.
Trevor Hoppe (12:15)
I can relate to that so much. remember going to the gay bar early days in the 90s and I remember the song came on, I’m horny, horny, horny, horny. And I remember my little 17 year old self or whatever thinking, why is everything about sex? And just feeling some kind of way about it. And then really discovering the wonder and beauty of sex and not just the sort of negative things that come with it. And what was that exploration like for you of turning from
Sister T’aint A Virgin (12:23)
Mm-hmm.
Hahaha
Trevor Hoppe (12:44)
you know, that kind of traumatic origin to having great, hopefully the best sex.
Sister T’aint A Virgin (12:46)
Yeah.
Right?
I think I, for me, like trying to, again, being a little bit of a control freak and a little bit of a Virgo, I like wanted to kind of dip my toes in in ways I felt comfortable with it. And so my early explorations were mostly as a voyeur and really just kind of like watching other couples.
Um, and I loved that. Um, it was able to kind of see and learn all the different kinds of ins and outs of how to pleasuring a partner, how to receive pleasure, uh, without having to kind of technically be involved in it beyond just watching. Um, and that
Trevor Hoppe (13:15)
Yeah.
How did you find
those experiences?
Sister T’aint A Virgin (13:32)
largely online. You know, these were back in the days before the apps. So this was kind of like a gay.com. I think manhunt was around at that point. Craigslist. Craigslist was a big one for sure. You know, and was like Craigslist was great, like if you were able to put up the specific ad and the posting that you were looking for. And so you’re able to kind of set those terms in a way that was much easier to navigate than I think we’ve kind of
Trevor Hoppe (13:41)
Mm-hmm.
Mm. Craigslist.
You
Sister T’aint A Virgin (14:02)
evolved into with the apps and things like that. The apps are great for just kind of listing the yes, yes and nos, but it’s not the same as kind of crafting the whole scene, which I felt was kind of more tailored to what I was able to find on Craigslist.
Trevor Hoppe (14:19)
Yeah, there’s kind of a fantasy aspect of Craigslist where you really lay it out in clear terms. It’s creative in a way that Grindr and Manhunt or whatever, it’s not the same, it’s static.
Sister T’aint A Virgin (14:21)
Mm-hmm. Yeah.
Right.
Yeah, yeah, it’s, feel like, you know, there’s much more of an instant gratification that can happen with Grindr and Scruff and Sniffy’s and all the rest, which is wonderful and great. And I love that in a lot of ways, but there is something about the kind of the mystery and the buildup that I felt like happened more with Craigslist and some of our other apps and, you know, well before that. yes. For sure.
Trevor Hoppe (14:55)
there was a lot of mystery. Always mystery.
So,
you’re watching, you’re learning. Are these gay couples that you’re watching?
Sister T’aint A Virgin (15:11)
Um, yes, at least in the early days. Yeah, earlier years, it was only gay couples. And eventually, I started kind of seeing a couple that I would kind of go and watch every so often, and it became kind of a more of a routine thing. And eventually kind of got invited into the actual scene. And that’s where I kind of had felt like I had
already established a little bit of a connection there, and then felt comfortable kind of dipping my toes into it more. And that then led to me finally kind of feeling more comfortable kind of engaging with other people. And early on, it was almost exclusively men. And then when I moved up to San Francisco and started again interning with the Center for Sex and Culture, they were hosting much more kind of these like
Trevor Hoppe (15:42)
Yeah.
Sister T’aint A Virgin (16:01)
pansexual parties and you’re seeing a lot of different kind of bodies and genders and expressions and all of that. And that I loved even more because again, it like exposed me to things that I wouldn’t naively have gravitated towards or thinking that’s kind of what it is that I’m one or interested in. And it allowed me to kind of continue to be that voyeur when I needed.
So they were able to see and witness and kind of participate in that capacity, which then led to me kind of more engaging in a variety of different sexual activities with different partners, different bodies, different genitals, all of it. And that’s what I… Yeah. yes.
Trevor Hoppe (16:42)
Mm-hmm. I love all the possible combinations of the world. What?
How did you find- I’m just curious, like that first experience, like, watching… How did you arrange- you arranged that online, but like, what was the experience like for you? Did you know that you were just gonna watch going in?
Sister T’aint A Virgin (16:55)
Mm-hmm. Mm-hmm.
Yes, I knew that I was just going to watch going in. And there was that level of comfort that was there. At the same time, it still going over to a stranger’s house. They, the couple had a very, very young child who was obviously not part of the scene. They were not there at the time.
But I went to their house and they gave me instructions to like come through the backyard because they had like their bedroom had a patio, which then had like full glass windows. And so they were able to sit on the patio on outside and just kind of watch them. But I remember walking in. Oh, well, from a distance in that like, yeah, there was like the glass screen door was there, but it was still
Trevor Hoppe (17:48)
from a distance.
Sister T’aint A Virgin (17:59)
very close in proximity. But it was kind of like watching a window show. And so it was nice because I felt like then if I needed to, I could leave at any time. But I do remember walking in and immediately tripping over one of the kids’ toys in the backyard.
and stumbling my way in and of course making a huge noise as I’m doing so. I’m like, well, there goes the fantasy. yeah, exactly. But yeah, I loved it. mean, they had a red light on, so that kind of added to it. it was just, yeah, like growing up, I of course had seen porn.
Trevor Hoppe (18:31)
That’s the real- that’s reality though, it’s always- it’s never quite the fantasy.
Sister T’aint A Virgin (18:50)
I had kind of plenty of material that way, but nothing compares to seeing it in person and seeing a couple that’s like knows each other’s bodies in a way that like is already super pleasurable and are excited about having someone else watch them. So there was kind of these extra layers from an early experience that was really quite lovely.
Trevor Hoppe (18:58)
Yeah.
Yeah. I think a lot of young people would benefit from watching. And old people too. We would all benefit from watching because you can learn something. Is that something you fantasized specifically about beforehand? I’m just, did you know that’s what you wanted to do?
Sister T’aint A Virgin (19:20)
All right. Yeah.
I would say,
yeah. I mean, I have always considered myself more of like an introvert in general. And so I think early on, kind of the key things of kind of getting better at sex and having a rich and fulfilling sex life has been able to navigate and communicate my wants and my needs. And early on being super introverted, being kind of very fear based, like communication was one of the hardest things for me.
And so I was like, I’m not going to be able to communicate my needs and my boundaries or any of that. And so I think doing this in a way that I’ve already pre set up everything, which is mostly just watching was a really the helpful step of kind of like, again, slowly dipping my toe in things that finally felt comfortable and enriching. And that’s when I really realized that I do enjoy watching. mean, I love actual activity and kind of getting involved as well, but
Trevor Hoppe (20:25)
Mm-hmm.
Sister T’aint A Virgin (20:30)
There’s something so beautiful about just bearing witness.
Trevor Hoppe (20:33)
Mm-hmm. What is it about bearing witness? I don’t have a lot of experience. I mean, I’ve seen a lot of sex myself, but it never occurred to me as a young person. Like, that just was not something that I thought was possible when I was learning about sex.
Sister T’aint A Virgin (20:48)
Yeah.
I mean, I think again, it kind of connects back to this whole ministry of presence with sisters as well. I think again, growing up, a lot of us had to specifically within kind of a larger queer community, we had to kind of blunt ourselves and we had to like kind of hide ourselves. so bearing witness and kind of being present and like seeing someone, seeing someone expressing themselves in the way that they’re super excited about and probably haven’t been able to or
are finally able to as a sexual adult. There’s some things just so fun and enriching. And, you know, obviously finding exhibitionists who are equally as excited about showing off. Yeah, for me, there’s just something something so beautiful about that kind of that level of dynamic and interaction. Yeah, I’m not sure I can put it into words beyond it’s Yeah, I just love it.
Trevor Hoppe (21:52)
No, I that. It’s something that’s beyond words. It’s like transcendental or some mystical. It’s something magical. I don’t know, but I definitely get that aspect of sex is hard to describe. What were your first forays into like actually having sex like? What was that like for you?
Sister T’aint A Virgin (22:12)
Yeah,
um, I, all of my partners were much older than me. Um, that was another thing for me that just felt more comfortable and safe. Um, there was something, some level of a mentorship there as well. Um, and, uh, through that, again, just kind of met up with, I had two or three guys that I would kind of see on a somewhat routine basis. Um,
And it started off with, you know, mostly just heavy petting, making out, hand jobs, all the rest, massage, kind of exploring each other’s body. And then kind of finally kind of developed into more kind of penetrative activities and whatnot. You know, early on, I didn’t really use any terms of top or bottom or anything like that, and was mostly just kind of there to kind of
experiment and explore and try things out. There was always the kind of overwhelming or kind of hanging over your head, this kind of fear of HIV. And so I think that kind of pushed me away from doing a lot of kind of penetrative sex for long periods of time. And then prep kind of completely revolutionized that and kind of beautiful, beautiful ways as Demon has already talked about exactly, right?
Trevor Hoppe (23:20)
Mm-hmm.
Blew the lid off it, yeah.
I remember in San Francisco back in the day, there was a lot of oral play and non-penetrative play, and I think that was part of that legacy of that now there’s so much, it’s just like, bam, fucking all the time, bam, bam, bam, bam, bam, it almost feels like we’ve lost a little bit of something. I don’t know, do you feel that way?
Sister T’aint A Virgin (23:46)
Uh-huh. Uh-huh.
Yeah. Yeah. Yeah.
I do. Though I have been quite, you know, I think people are really polarized about the term side or kind of the role of side. But I personally have loved seeing that kind of take its time in the spotlight. Because I think it right, like so much of it is focused on penetration. And don’t get me wrong, I love it as well. But
there is something equally as beautiful and equally as pleasurable and kind of fun and kind of like then mystical about exploring other ways of being sexually active together that doesn’t always require penetration.
Trevor Hoppe (24:42)
Yeah, I remember years ago I met up with a guy who had never watched porn and did not engage in penetrative sex. And at first I was like, I don’t know, this is probably not going to be great. And then it was this just mind-blowing experience, I think because there were no scripts in place. It was just our bodies. I don’t know.
Sister T’aint A Virgin (24:48)
Mm-hmm.
Yeah.
Uh-huh.
Totally.
Yeah.
Yeah.
Trevor Hoppe (25:09)
Again, I can’t really describe it in words, but I appreciated the reminder and the power of non-penetrative sex.
Sister T’aint A Virgin (25:14)
Totally.
I think there’s something else that that’s kind of reminding me of is that, you know, in being in these kind of pansexual play spaces, there were plenty of kind of people that I was watching and kind of bearing witness to, who I personally probably wouldn’t want to actively engage with beyond kind of just watching.
But a lot of that then meant that there was like a lots of just kind of mutual masturbation that was happening throughout these spaces. And being able to masturbate with a partner who you’re not exactly kind of interested in kind of penetrative sex with, but also kind of loving and exploring them kind of pleasuring themselves or kind of watching them do something else was also equally as fun and engaging. And especially, you know, at the time, like seeing kind of other genders.
Trevor Hoppe (26:03)
Mmm.
Sister T’aint A Virgin (26:07)
kind of exploring themselves and seeing how other genders are kind of doing sex that’s not exactly penetrative was this kind of wealth of San Francisco underbelly that I just love and it’s through San Francisco.
Trevor Hoppe (26:23)
huh. I remember it well. That was a fun two years when I lived there, for sure. A lot of times I feel like, at least, that I’ve learned some of most valuable lessons about sex from having bad sex. Are there experiences like that that you can remember that were like, god, it went bad, but you walked away feeling like, you know, a little enlightened?
Sister T’aint A Virgin (26:25)
Hehehehehe
Yes.
Yeah. Yeah.
Right. think the thing that comes most pertinent to me is kind of early on in coming up to San Francisco, I was living in a kind of queer collective household that was known for throwing lots of sex parties and being the host of the parties. You were always there, which was fine. I love that. But I still hadn’t kind of fully come to owning
Trevor Hoppe (27:02)
Mm.
Sister T’aint A Virgin (27:13)
my boundaries. And so I still remember kind of early on kind of being engaged with people who were probably a little bit more aggressive and a little bit more either under the influence of certain substances, where it just made it harder for me to kind of truly feel comfortable voicing my, no, this is passing the boundary. Let’s let’s pause here. And I found myself just kind of remaining quiet and a lot of those times.
and kind of just going through with something in order to kind of get it done. And it, of course, didn’t feel great in the moment. Of course, afterwards, it felt even worse because there’s like levels of kind of shame and guilt there. But it did eventually kind of lead to me to being like, like, no, body autonomy is an important aspect of what I view as sexuality, as is consent, as is kind of pleasure. And so
All of that needs to happen through communication. And I just need to kind of develop my communication skills and saying what I do want and what I don’t want and hearing what my partner wants and hearing what my partner doesn’t want. Still something I’m learning and kind of developing, but it is one of the aspects that I think it’s hard.
Trevor Hoppe (28:29)
Yeah, it’s a skill and a muscle you have to strengthen, which is… People think that saying yes or no is like easy peasy, and then the reality of it is, of course, much more intense when you’re face to face with another human being who’s desiring you, and you want to be desired, obviously, but you have to be able to set that boundary for yourself. Do you have any tips for… Because really…
Sister T’aint A Virgin (28:43)
Totally.
Mm-hmm.
Trevor Hoppe (28:56)
My dream for this podcast is to help young people who are like little yous and little me’s who are trying to figure out how to set those boundaries for themselves. What do you think helps?
Sister T’aint A Virgin (29:02)
Alright.
I think finding your community, which I know is a very broad and kind of general overarching term, but like finding the people that are interested in exploring the same ways. and ideally you can find that your mentors within that, cause that’s largely what I did. And I feel like the mentors can.
were the ones that helped ushered me through being more comfortable, being more sexual, being more engaged. And I feel like within the subsets of our communities, there’s pretty rigorous mentors out there and these little networks. And it does take time to find that group that you really resonate with or connect with. Again, I’d always say,
personally going back and then enjoying just watching or going to someplace that you can kind of activities that don’t exactly or immediately need to be kind of hands-on, but kind of collectively pleasuring yourselves in a way that feels wonderful.
Trevor Hoppe (30:26)
Daddies are having a moment, obviously, but back in our day, there was so much stigma around AIDS that I think intergenerational stuff really got a bad rap. Today we’re in a different place around that, but I still think obviously there’s some intense stigma around intergenerational sex and relationships generally.
Sister T’aint A Virgin (30:28)
Yes.
Okay.
Trevor Hoppe (30:48)
What would you say to a young person, like you should have sex with an older person, but like what, how do you counsel someone who is kind of feeling icky maybe about that?
Sister T’aint A Virgin (30:54)
Yeah.
I always think of like, we don’t want history to repeat itself, but we don’t know the history. like, I think a lot of older men have decades worth of lived experience. And that lived experience is so important and so critical in kind of helping pass along kind of the ins and outs and exactly what does work for you, what doesn’t work for you.
You know, I think that intergenerational partners really kind of bring new flavor to the scene. it kind of inherently has some level of a mentorship involved with it. You know, granted, there’s can be different forms of, power dynamics that come into play there. But, my richest and most wonderful relationships, both as friends and as sexual partners, have always been with people that are probably about.
15, 20, 30 years older than me. And now that I’m kind of moving into my, moving towards my forties, I find myself also kind of mentoring some of our younger generations. And so that’s been an interesting kind of shift of kind of being the younger one in the room to now being the one kind of solidly in the middle. And so
Trevor Hoppe (32:24)
Yeah, I feel that deeply. The moment all the twinks start messaging you saying, hey daddy or whatever, you’re like, oh my God, daddy, is it time yet? But it is time. And I have come to appreciate that role. I resisted and resented it for a while. But I think, I just think about little game me and how he really could.
Sister T’aint A Virgin (32:26)
BLEH
Yup.
Mm-hmm.
Trevor Hoppe (32:52)
It did benefit and could have even more benefited from that kind of mentorship that you’re talking about. Do you remember any lessons specifically that older guys taught you?
Sister T’aint A Virgin (32:56)
Yeah. Yeah.
Um, I mean, I think I was super lucky in that the first partners that I had were not so focused on penetration. Um, and so I think kind of early on learning that penetration is not the end all be all for sex. Um, and to kind of like, slow your role, take your time, really explore, um, that, uh,
was something that was super helpful for me. Just because, right, like I think so much of it was focused on like, all right, who’s gonna be the top, who’s gonna be the bottom, let’s get this done. You know, everything leading up to it is just kind of like quick little steps along the way, but the main goal is to penetration. And I think early on kind of seeing other forms of sexuality and really kind of seeing how to receive pleasure and be pleasured.
that doesn’t revolve around penetration.
Trevor Hoppe (34:07)
Mm-hmm.
That’s great. My memory, I have a specific memory, is living in San Francisco, actually. I was hooking up with this guy who was much older than me at the time, and he taught me, this sounds so stupid, but I really value it. He taught me to put lotion on my body after I take a shower, and it has left my skin supple into my 40s, and I’m grateful.
Sister T’aint A Virgin (34:25)
Yeah.
Love that!
Trevor Hoppe (34:32)
But yeah, I so I have started to really appreciate that daddies and older guys generally in our community do have wisdom. I am now one of those people. So I’m trying to appreciate what that can look like in a healthy way because there is a lot of potential for unhealthiness in those relationships. How do you navigate that?
Sister T’aint A Virgin (34:52)
Of course, of course.
I mean, personally, I’ve usually met up with partners outside of sexual setting first, whether it’s just like a quick, simple little coffee break or somewhere out in the community, somewhere that doesn’t feel kind of immediately charged and kind of setting up intentions and or expectations. and as long as there’s kind of a vibe and there’s good chemistry, then we kind of like quickly pivot more towards the bedroom. but
Trevor Hoppe (35:23)
Mm-hmm.
Sister T’aint A Virgin (35:25)
because I’ve definitely, you know, you know, when you’re crafting this fantasy, when you’re chatting and you’re flirting online for long periods of time and you build up these expectations and then you show up at their house and it’s not exactly what you’re looking for, that’s always harder to navigate and harder to kind of get yourself out of versus if you like kind of initially just do a little kind of quicker touch base, let’s get meet out in the community, let’s do something that feels more comfortable.
Trevor Hoppe (35:39)
You
Sister T’aint A Virgin (35:54)
to really kind of suss out if this is actually going to be a good connection. Because our online personas are not always the same as our in-person personas.
Trevor Hoppe (35:59)
Yeah, that’s really smart advice.
Yeah, yeah, just the idea of meeting up with someone at a bar or something. I used to do that a lot more than I do these days. Maybe schedules are tough sometimes, but I like that ideal a lot. I really found it valuable as well.
Sister T’aint A Virgin (36:11)
Mm-hmm. Yes. Yes. Right.
Trevor Hoppe (36:21)
What does really amazing sex look like for you today?
Sister T’aint A Virgin (36:27)
Um, really amazing sex for me today. Um, I have recently discovered the term symbiosexual, um, which is kind of receiving or enjoying kind of watching the dynamic of someone else and specifically other couples, um, which kind of gets rooted back to my early days as a mostly a voyeur. Um, and so.
Trevor Hoppe (36:37)
Mmm.
Sister T’aint A Virgin (36:55)
that’s mostly led to like my best sex has always been in group settings. Whether it’s with another couple, I mean, the absolute best sex I’ve ever had was with a throuple where everyone was averse and everyone was like both fun and playful as well as super into each other, which I know the sooner I as a minute as.
When you add more people in, it’s harder to make sure that there’s like sexual chemistry across all partners. But for whatever reason, it worked. And it was fun to be able to kind of pair off into individual pairs and come back together, switch partners, do more of a group scene. But yeah, I love kind of being in the midst of larger group dynamics because it allows me to continue to be that lawyer, to bear witness, but also be engaged.
And it’s just fun seeing how other people receive pleasure from other people to me.
Trevor Hoppe (37:56)
Are these regular groups that happen, you know, with the same people?
Sister T’aint A Virgin (38:01)
Sometimes.
Usually if they’re couples or people that I know, then yes, I would say kind of ongoing. But if it’s more of like, kind of either play parties or sometimes I’ll go to this kind of gay men’s sketching group where it’s two hours of sketching and most of the people that sketch, we take turns modeling as well.
And then after two hours of lovely sketching, usually devolves into a lovely social hour, which is Sans clothes and very enjoyable. And so that changes the dynamic because every week there’s different guys that show up and sometimes it’s regulars and you’ll kind of see them on recurrent days. And sometimes it’s people’s first time. And so it’s nice to kind of welcome people into that group and kind of
and get matched with someone, you can kind of go back and play with them on a recurring basis. And if it didn’t work out that one time, you can maybe try some different partners. So it’s nice to kind of mix it up in that regards.
Trevor Hoppe (39:11)
Do ever find that there’s someone that you thought, I’m not gonna get along with them at all, and then you just have this amazing encounter?
Sister T’aint A Virgin (39:18)
Yeah. Um, and I find like that the group settings has really been helpful for me for that. Um, I’ll definitely like go into some of these sketch groups. I’m just like, all right, there’s the one person that I definitely am excited about. And we’ll like, are really all of us will be without our clothes on and we’ll be kind of starting to play and they’ll like immediately be aligned to someone else. Uh, and then you’re just like, all right, well, that’s not going to work out there. So let’s kind of pivot and navigate. And so
Again, it’s kind of these group settings, it kind of exposes me to people that I probably once have gravitated to online or kind of sought out individually. And then, you know, you’re in the dynamics of sex and you’re realizing that they’re quite skilled at certain things. And you kind of take beauty in that and kind of realize that, you know, your instant kind of viewing of them might not have been the most reliable in terms of
Trevor Hoppe (40:06)
You
Sister T’aint A Virgin (40:17)
really enjoyable sexual partners.
Trevor Hoppe (40:20)
Yeah, there’s something that can happen where you just realize sexual attraction to someone, you didn’t see it at first, but then they smile a certain way or they unbutton a button or whatever and it’s like, oh, I see you now.
Sister T’aint A Virgin (40:32)
Right,
right. my early, I mean, I think my kind of early experiences playing with trans men was a lot of that as well. Where, like I knew that like my attraction was mostly to kind of like masculine identified individuals. And kind of being in play spaces that were kind of gender explorative and gender inclusive.
Trevor Hoppe (41:02)
So one of the beautiful things about the in-person kind of drawing class thing is that you can kind of see people visually in different… in ways that they would not present themselves online, if that makes sense.
Sister T’aint A Virgin (41:15)
Exactly.
Exactly. You know, and like when you’re drawing them, you’re kind of enjoying the beauty of like this specific curve in their body. And it’s like not always focused just on the genitals. And you can kind of like really appreciate you know, the way that the light is hitting their clavicle or, you know, the little dimple on their backside. And I think that you can kind of find the beauty in those little things that you wouldn’t normally kind of gravitate towards that really
makes me excited to explore them their bodies more fully after drawing sessions. And yeah, it’s not always focused just around the genitals.
Trevor Hoppe (41:58)
Yeah. Do you have any tips for… because online, obviously, you lose that ability. I know you said you meet people beforehand, but before you even made up, are there ways that you try to assess people’s…
Vibe? Is that word? I’m not sure exactly.
Sister T’aint A Virgin (42:17)
Yeah, mean, I usually like I know some people and you know, no shame to it. Like they want to just like, they use the apps to get in get out. They want you know, they don’t want the banter. They don’t want the chat. They just want to know what you want. They want to set it up and they want to get going. And for me, like I actually enjoy getting to know them and kind of enjoy kind of flushing out the personality behind the body.
because that’s gonna be more key and that’s gonna be more sexy and more engaging to me than, you know, just the standard body itself. And, you know, of course, every so often that’s actually just what I want. It’s just a quick hug up. And so that’s lovely too. But that always comes with some level of, you know, is the actual dynamic gonna be there? Is the actual dynamic gonna be comfortable? So I just have to kind of be willing to roll the dice sometimes and
you know, maybe not have the best of connections initially and just hope that the sexual attraction will kind of push me through it. But usually I like to kind of, you know, get to know them on some level before kind of immediately jumping into the sheets.
Trevor Hoppe (43:31)
And you mentioned the symbiose… symbiosexual? Is that… this… Yeah, this is a term I’m actually not familiar with. What… what is that term, doofyur, that’s different from voyeur?
Sister T’aint A Virgin (43:34)
Mm-hmm. Yep.
Um, I think it’s more specific about enjoying the dynamic of another couple. Um, and so like a voyeur can just be like, it could just be one single person. And the symbiote sexual is like really loving the like loving dynamic between a predetermined couple and kind of getting sexual gratification from that. And so I think it’s to me, it’s just like another layer onto voyeur or voyeur is kind of this broad term of watching anything.
versus kind of the symbiosexual, which is like really enjoying the watching the dynamic of this other couple. And you’re getting specific pleasure from that. And kind of engaging with that too.
Trevor Hoppe (44:28)
And it sounds like you’re also watching couples that are not gay men now.
Sister T’aint A Virgin (44:33)
Yes. Yeah. Again, largely through kind of these play parties that are kind of welcoming of everyone and everybody. Really seeing kind of ways that not all gay men, but kind of, kind of the larger trans umbrella, straight couples, queer couples within the kind of, you know, gender nonconforming, non-binary, all of that.
Trevor Hoppe (45:03)
that change your attraction?
Sister T’aint A Virgin (45:05)
Yes, I think so. I’m still mostly attracted to displays of masculinity or masculine characteristics, but I have a lot of loving and wonderful trans masculine partners. For me, the attraction in the sex is not specifically to a cock or to a penis. It’s the display of masculinity and that’s…
Exploring that through having partners who are trans has been amazing and wonderful. I lived in a larger queer household separate from the one that I mentioned earlier that was largely female. long stretches of time, I was the only male identified individual in the house. It was all queer. was being immersed in largely femme-focused sexuality.
made me love and appreciate a lot of kind of femme identified bodies as well. And see how sex is navigated and explored in different contexts outside of just the gay male experience. So I always have a little strong affinity for that too.
Trevor Hoppe (46:26)
Yeah, I remember going to the bar on Castro with my friend who was a trans guy. This is back in the early 2000s and there would always be like, he would be making out with someone within 30 seconds instantly. He was so handsome and is so handsome to this day. And I remember, know, time would go on and then there would be the moment where the disclosure would happen.
Sister T’aint A Virgin (46:36)
Huh?
Trevor Hoppe (46:45)
And it was interesting, even back in the early 2000s, I would say most times it was fine. Guys were like, fuck yeah, let’s do it. And I loved that. I think he was…
Sister T’aint A Virgin (46:49)
Hmm? Hmm?
Yeah. at a.
Trevor Hoppe (46:56)
systematically educating the Castro about trans bodies back.
Sister T’aint A Virgin (46:59)
totally. Totally. Totally.
Yeah, I worked at a sex club here in San Francisco for several years. And I’d say at least half of my coworkers are trans men. And it was amazing seeing this like, sex club that is tailored towards men, who was like, all inclusive of kind of the kind of larger umbrella of male bodies, including kind of trans men. And so
that was just fun kind of being part of that network. and we would post, occasional workshops, tailored towards like cis men, pleasuring trans bodies and trans men, pleasuring cis bodies. and it was really fun kind of being in these safer spaces where people could ask questions that they don’t always feel comfortable doing with an individual partner. and not feeling judged for it.
and really kind of hoping to expand their idea of what it means to be sexually attracted to kind of the larger umbrella of men.
Trevor Hoppe (48:08)
That’s fabulous. I love that. I always like to end on a fun segment I call Sorted Lives and Untold Tales or SLUT for short. What’s the sluttiest thing you ever did?
Sister T’aint A Virgin (48:16)
Huh? Uh-huh.
You know, I think it’s, you know, probably the recurrent sex parties that I’ve gone to and hosted at my house over the years. that seems kind of the obvious or the easiest answer. I think outside of that, more recently, I had my very first kind of, fisting experience, with again, someone who was older than me, very, very experienced in fisting.
And it was fun to just kind of explore that in a way that felt that I wasn’t being judged, that I could kind of make some mistakes and feel comfortable with it. I really, really loved and learned that I enjoy being a fisting top. So, you know, I think that’s going to be a new foray into other experiences that I’m hopefully pursuing. So yeah.
I’d say that was my other kind of sluttier moment as of most recently.
Trevor Hoppe (49:19)
I love that.
Yes, absolutely. think fisting is, in the post-prep world, it’s one of those things that’s become more popularized, I think it’s fair to say, and people have become open to this experience in a new way. I’d love to hear that. If people want to learn more about you and the work that you do, where could they find you?
Sister T’aint A Virgin (49:37)
Right.
Um, so the first thing would be going to the sisters website, which is the sisters.org. Um, and that’s for the San Francisco chapter. Uh, but that gives a good overview of kind of our history. Um, you get to see who our individual members are. Um, my personal social media, um, on Instagram is sister underscore taint underscore a underscore Virgin.
But the website is probably the easiest way to kind of get a general understanding of who we are and how to get involved.
Trevor Hoppe (50:19)
Thank you so much sister
Sister T’aint A Virgin (50:21)
Thank you.
Trevor Hoppe (50:23)
That’s our show for today. Thank you so much for listening as always. And remember, if you aren’t having your best sex, I can help. My services as a sex coach are designed to help you identify and overcome the barriers that are standing between you and your best sex life. Find out more on my website, thebestgaysex.net. Till next time.
