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52 heterosexual cis male, married almost 20 years, west coast-based, into: squirting, voyeurism, anal.

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00:00:00:03 - 00:00:28:20

Luna

And our guest today is a 52 year old Swiss dude who has been married for almost 20 years. He has a strong streak of voyeurism. Has recently been enjoying mostly giving, also sometimes receiving anal pleasures, and gets super turned on when his wife squirts and also wants to explore other wet stuff. In recent years, he lost his sex drive, got it back, and finally achieved his number one greatest fantasy that includes I'll give you a hint penetrating.

00:00:28:20 - 00:00:34:20

Luna

Formerly a formerly taboo whore, an engineer from the West Coast. Welcome, Jack.

00:00:34:22 - 00:00:36:15

Jack

Thank you. It's great to be here.

00:00:36:17 - 00:00:52:05

Luna

I'm so excited to have you here. Can you please start off by telling us if you had to rate yourself today on a sexual shame meter, with ten being the most full of shame and zero being like, I don't have any of that. Where do you fall today? Right now? And when? If ever, does it get squiggly?

00:00:52:07 - 00:01:14:15

Jack

It's pretty low. I'd say, you know, one, two, three somewhere in that range. Thanks to I know the things that that turn me on, turn me on. And I'm fine with that. It's hard to say when it perks up. Maybe talking about things. We'll see. And even there, I don't know if that's shame creeping in or just shyness or a sense of privacy and and whatnot, but, yeah.

00:01:14:15 - 00:01:16:18

Jack

So I'd say it's a pretty low.

00:01:16:19 - 00:01:28:16

Luna

Okay. Who in general do you talk about sex with? Like we're talking about it. You've listened to the podcasts. I would imagine you talk about some things with your partner, but does it ever come up in the rest of your life?

00:01:28:18 - 00:01:55:07

Jack

Not really. Not in anything. That's more than just a passing comment or certainly doesn't come up in work in those places. I work for a corporation. Those conversations do not happen in that environment. So yeah, most of my conversations about sex are with my wife and getting better. We're doing better with communication. In part, I think for me, listening to podcasts like this, has helped hugely.

00:01:55:09 - 00:02:15:00

Jack

We're very humans are very monkey see, monkey do. And when we see and hear other people having open, honest conversations about sexuality, then, you know, I could do that. I could talk about that stuff. So, yeah, that's that's helped a lot. And, yeah, we, we're getting there. I'd say I'm doing better.

00:02:15:02 - 00:02:26:13

Luna

Okay. I love that. Could you tell us when it comes to sex? What would you say you are the best at? And how did you get to be so good at it?

00:02:26:15 - 00:02:46:16

Jack

Gosh, I'm not sure it's. I like I'd. Sex is just fun. It's just. It's a whole lot of fun. It's exciting. I think that's what I bring to it. I just I want to have fun. I want us both to enjoy things as much as we can. If my partner can let me know what she wants, I'll do that for her.

00:02:46:18 - 00:03:08:16

Jack

You know, I feel it's. It's a good back and forth. With my wife in particular, I think I'm pretty good at pleasing her with my mouth going down on her. She really enjoys that. And I do, too. So whether that's licking her pussy or licking her ass or, you know, whatever, all that oral stuff, she loves it.

00:03:08:16 - 00:03:10:15

Jack

And, and I love doing it for her.

00:03:10:17 - 00:03:23:21

Luna

Amazing. Do you feel comfortable sharing any, like, specific details of, like, ways you like to lick or, like, favorite things to do with tongue and or touches that may or may not accompany this licking?

00:03:23:23 - 00:03:46:17

Jack

I don't know. I don't have any particular tricks. No rules, no special things. She requires a lot of clitoral stimulation, so I really have to kind of go after whether it's rubbing firmly with my fingers or licking fairly firmly with my tongue. That's what's going to get her kind of over get her to come. She also enjoys, like if I'm licking or clit, also a finger.

00:03:46:19 - 00:04:07:15

Jack

That's kind of an added stimulation for her. So yeah, but I just kind of cruise around. I try to judge her response and see, okay, that, you know, that got, you know, more reaction, she's more vocal or whatever. And I do more of that. So I try to try to read her her responses as well as I can.

00:04:07:17 - 00:04:08:06

Jack

00:04:08:08 - 00:04:20:12

Luna

So if I'm understanding correctly, it sounds like part of the fun that you bring to the table is crafted off of that connection and listening, whether it's like with your ears or your whole, you know, whole body listening basically. Right.

00:04:20:14 - 00:04:42:10

Jack

Yeah. I want it to be as good as possible for her. So I'm going to try to to identify what makes that happen. Yeah. And in years past, I mean, that's kind of was the extent of it. Now, like I mentioned with communication, we're talking about it more. And then maybe after sex either immediately after or later that day I might ask.

00:04:42:10 - 00:04:51:02

Jack

So, you know, I noticed her reaction when I did this or that, and we'll talk about it a little bit. So, you know, okay. And then I, I can file that away.

00:04:51:04 - 00:05:11:23

Luna

I love that so much. I really love recaps with partners, whether it's just to like, you know, kind of reiterate how hot a certain thing was or to get more information about, like when I did this, could you feel, you know, like and so I recently initiated that with, with a play friend who have had off and on for the last year or so, and it's so fun.

00:05:11:23 - 00:05:14:23

Luna

And I'm like, when I hear about married people who don't do that, I'm like.

00:05:14:23 - 00:05:16:15

Jack

Oh, well, you're missing out.

00:05:16:15 - 00:05:27:23

Luna

On you think you know, and I know it's not. I know not everyone responds to it the same way, but it warms my heart to hear that you have that worked in. Do you feel like you are usually the initiator of that, or have you guys kind of created a bounce back dialog?

00:05:28:03 - 00:05:49:11

Jack

I'm usually initiator that. So and I find the it's the most comfortable time to have a conversation is after sex. It's like when I feel the best I'm the most relaxed. I just, I feel good, like with the world and everything. So it's much easier for me to initiate the conversation. Okay. And to just kind of see where it goes, even if it's just a very short conversation.

00:05:49:11 - 00:05:52:21

Jack

Yeah, yeah. That just seems to be what works best.

00:05:52:23 - 00:06:11:00

Luna

I hope so. Okay. Listeners out there. I'd be so curious if any of you who have sex with penis owners and or are a penis owner. I feel like this is a dude thing because sometimes after sex, after coming, I'm like, I'm a noodle, I can't even function. And that's when my penis owning partners are like, let me tell you all my thoughts and feelings.

00:06:11:00 - 00:06:19:05

Luna

And I'm like, I can really feel it. Especially if it's an impact session or a whole thing. I'm like, it's a lizard right now. Or like, you just made me come and I need a few minutes.

00:06:19:07 - 00:06:21:17

Jack

I need to say like, okay, let's check.

00:06:21:17 - 00:06:22:07

Luna

On the other side.

00:06:22:07 - 00:06:28:16

Jack

Let things, you know, relax for a minute. But then, you know, after a few minutes, yeah. You know, and certainly later that day, I'm. I'm ready to chat.

00:06:28:18 - 00:06:39:12

Luna

I think it's really cute. I love it, but I'm sometimes I'm like, so maybe everyone just needs to come more in order to open up, you know, like, that's kind of my working theory. Or at least anyone whose emotions feel stuck, I don't know.

00:06:39:12 - 00:06:40:17

Jack

Sounds good.

00:06:40:19 - 00:06:59:01

Luna

I mean, it definitely is a good idea, regardless of whether or not it results in talking. In my opinion. What do you need in order to feel excited to connect with your partner? So you've been with your partner a couple of decades, but like, do you need to be in a certain like mode or have certain needs met in order to get to like the physical fucking part?

00:06:59:01 - 00:07:00:13

Luna

Like, what do you need there?

00:07:00:15 - 00:07:20:00

Jack

Not anything specifically. Most of my life, my sex drive has been so high that it's. I'm ready to go, like, whenever, if, you know, with my partner when I was dating, had a girlfriend. Now with my wife, if they're like, hey, you want to. Yeah, I'm, I'm sort of. I'm ready to go. I don't have to have be relaxed.

00:07:20:00 - 00:07:45:22

Jack

I don't have to have the house clean, you know, whatever. I'm just like, I'll put aside everything else and and jump into that if I'm invited. And also I think in general, like for me, I don't need necessarily the connection first that then allows or or invites sex. To me it's kind of the opposite. I can have sex with someone because we're both horny and we want to.

00:07:46:00 - 00:08:12:06

Jack

Yeah. And then the connection comes later. It's, you know, it could be a sort of catch feelings or with my wife, it's kind of like we have sex. And then I feel the connection. Come on. Because there's kind of that, that container for it. Yeah. So that's sort of I think most people or I've heard people talk about it the other way around, like without a connection, the sex isn't good or doesn't work or whatever.

00:08:12:07 - 00:08:17:09

Jack

But flip that and I can I can lead with the sex and then connection can happen later.

00:08:17:11 - 00:08:19:09

Luna

I totally relate to this, and I think there.

00:08:19:09 - 00:08:20:06

Jack

Are.

00:08:20:08 - 00:08:38:11

Luna

A lot of, for me, confusing signals out there because a lot of people have different experiences in this world. And I've heard a lot of discussion that it, again, has to do with, like whether you're a penis only owner or pussy owner, and I for me, I'm another person that's like, yeah, well, let's find out if we have the physical thing and then and then we'll go from there.

00:08:38:11 - 00:08:57:10

Luna

And you know, in terms of dating, it's not always the like I it's taken me a minute to realize that there still really are like categories attached or even some guys do want to have more connection at a time. Like I've had a couple dates in the last couple of years that are like, well, I'm like trying to take you on a date, I'm trying to take you dancing and you just want to fuck.

00:08:57:10 - 00:09:08:01

Luna

And I'm like, oh no, I don't just want to fuck. It's just like, I want to make sure that we have that. We smell good to each other and that we feel good to each other. And also, I just really like connecting in that way. So I yeah.

00:09:08:05 - 00:09:25:19

Jack

So I'll mention that with my wife and I sex is usually planned. It's at least day of like that morning. It'll be like hey, you know today or it's a day in advance. Yeah, maybe with something like my birthday, it might be a little bit, you know, more in advance, you know, which weekend is going to work. And I totally like that.

00:09:25:19 - 00:09:47:21

Jack

To me, it's it builds the anticipation. It's like waiting for Christmas. Like, oh, yeah, that's on my mind. And I clear the schedule and I arrange things that, oh, I can't go to the store. I, I don't want to be busy doing this other crap chores, whatever. You know, I want to be here and ready. And so and I think that's kind of a part of being in such a long term relationship.

00:09:47:21 - 00:10:03:08

Jack

You know, the locked eyes spontaneity thing does doesn't so much happen anymore. But, hey, I'm feeling good this weekend, and then we. Okay, how about Sunday? Yeah, Sunday sounds good. And then, you know, that just gets me eager for it.

00:10:03:10 - 00:10:22:22

Luna

Same. I love looking forward to stuff. I mean, a good amount of spontaneity I'll always take. Right. But if it's especially if I'm with a consistent ish partner and it's always like last minute booty call, I'm like, well, okay, that's good too. But it's not the only thing I want. Because like, sometimes I would like to be freshly showered or have just shaved my legs.

00:10:23:04 - 00:10:39:08

Luna

Not to perform for you, but because I like to feel smooth and soft. And I'm a sensual being, you know? And so, so for me, that and that's part of the ritual and the excitement and the build up and the looking forward, just having something to look forward. I totally agree. It is like it's like looking forward to Christmas.

00:10:39:10 - 00:10:44:05

Luna

When do you feel sexiest yourself?

00:10:44:07 - 00:10:54:22

Jack

That's a tough one. Feeling sexy. It's. And it's versus feeling horny. I don't know where those different things. No no no no.

00:10:55:00 - 00:10:56:13

Luna

Maybe it depends on the day.

00:10:56:15 - 00:11:22:06

Jack

Yeah. It could, So. Yeah, my desire, like I say, for most of my life, was very high. It would vary a little bit day to day, and now it varies more, I notice I'm, I'm more in the mood earlier in the day, so, like, sex at lunchtime would be like, best in my wife and I usually have sex in the afternoon by evening.

00:11:22:06 - 00:11:39:06

Jack

We're both kind of like, yeah, we've had dinner. It's, you know, the, the the day it's time to just kind of chill out. Yeah. I'll masturbate in the evening. So solo sex is fine at that part of the day because there's there's no pressure, there's no worries. I could just relax and and have some, some feel good time.

00:11:39:07 - 00:11:43:23

Jack

So, yeah, that's kind of my my timing for things.

00:11:44:00 - 00:12:02:13

Luna

I totally get that. I feel I used to not feel horny in the mornings at all, but now I'm like, that's oftentimes I'm not. Yeah, I'm sleepy at night. I mean, I will definitely also masturbate at night, but I totally relate to that afternoon. The lights are the best. I still want to achieve the long term dream of maybe getting a space at some point and hosting Afternoon Delight parties.

00:12:02:13 - 00:12:22:11

Luna

We'll see. I really would like to have like a proper retreat space to do, just like creative stuff. And then yes, the weekends are for fucking. I mean, every day is for fucking, but like, the group parties. Okay, so tell us, how did you learn about sex? Like, take us through your formative pleasure timeline, starting with when do you first remember hearing about it?

00:12:22:11 - 00:12:29:13

Luna

What do you remember? And then like, yeah. Did you get a sex talk? Was this sex ed in school? What were your sexy learnings like?

00:12:29:15 - 00:12:50:21

Jack

Yeah, it's there is no one moment. It's not like as a kid or an adolescent, some point it was like, oh, what? What's that thing? Yet it formed bit by bit over the years. And the first thing that that dimension is my dad's old Playboys from, these are like 1965 to 1970 or so. Those were in the house.

00:12:50:21 - 00:13:11:19

Jack

They weren't locked away. They weren't really hidden. They were just kind of up on a high shelf. My brother and I could still get to them. I have one older brother. But for anyone who doesn't know, Playboys of that era are like artful nudes. A lot of bare breasts, posed bodies, some bare butts, some bush. No spread open legs.

00:13:11:19 - 00:13:36:10

Jack

No. You know, there are TV shows now that are far more sexual than those old playboys were. So that was kind of a, an early exposure to, to women's bodies. I know my reaction. One was just sort of childhood getting away with something like, I knew we weren't supposed to be looking at these, or at least I seem to remember that.

00:13:36:10 - 00:13:58:21

Jack

I don't remember ever being told that, but that was certainly what my brother and I thought. But there was also curiosity there. There was something kind of drawing me in, and I can remember having crushes on girls always. Like, I can remember being four years old and having a crush on the neighbor girl. So there was always something about girls around me that that drew me in.

00:13:58:23 - 00:14:21:23

Jack

Also, just kind of as a part of sex or sexuality. I grew up in a rural part of the country. People around me had farms and ranches. There's animals around. When it's time for breeding season to breed the animals. So I was aware of the biological part of it, like male and female get together and make offspring.

00:14:22:01 - 00:14:43:22

Jack

So it wasn't that much of a stretch to figure out that humans do something, although it was called screwing. And that didn't quite make sense because screwing implies twisting, and I didn't think that's how it worked. That's such a good point. But, you know, so I was trying to put some pieces together. We had one of those old school big satellite dishes in the backyard, and we got all the stuff.

00:14:43:22 - 00:15:04:15

Jack

We got HBO, Cinemax, Showtime, The Movie Channel, and my parents would watch whatever they wanted to watch, okay, R-rated movies, whatever, when I was like a teenager. So, you know, I'm sitting on the couch watching and there's plenty of, you know, brief nudity and adult situations. Okay, so, I was never asked to leave or cover my eyes or any of that sort of stuff.

00:15:04:17 - 00:15:29:21

Jack

It also just wasn't talked about. It was just very neutral. Like, this wasn't shameful, but it also wasn't a conversation starter. So I putting all those pieces together and then, puberty comes along and then suddenly the sexual part really comes out. That curiosity about girls grew into, you know, a lot more in a sexual attraction for girls.

00:15:29:23 - 00:15:53:21

Jack

As far as sex ed, fifth grade, we had like, puberty talk. You know, bodies are changing. In high school, we got sex ed, which was actually, I give them credit. Pretty good for the time and place. It was all very fact based. It wasn't shame based or fear based. Great. It was all about, how to avoid STIs.

00:15:53:21 - 00:16:22:19

Jack

So all the methods for that, it was all about birth control. How do I pregnancy all of the methods for that. One of the classes was taught by a local gynecologist who came into the class. They did it that way, probably because this is the late 80s and, the Aids crisis was happening. So they wanted to to prepare us with some actual information, because at that time, you could catch catch Aids and it would kill you.

00:16:22:21 - 00:16:49:01

Jack

Yeah. It was there was no treatment for it or no effective treatment. So. So that's when I first started learning about sexuality. That was very much awareness in the background. As far as consent. No, right. There wasn't really anything about consent except for no means no. That's it. That's the extent of it. No more information than that. Except for for what society told me, which was basically, dude, if you want a girl, you got to make a move.

00:16:49:06 - 00:17:12:05

Jack

Chase, pursue, go after her. Yeah, and I'm not that guy. I wasn't that guy in high school. I was a scrawny, shy, introverted nerd. I was not what the girls were interested in. I'd go to dances occasionally, but I didn't have a girlfriend. I didn't do any dating. There were no early, you know, relationship experiences like that for me in high school.

00:17:12:05 - 00:17:24:12

Jack

I just I didn't know how to make that happen. I don't receive signals. And it's, you know, it's one of those things years later, I'm like, oh, relatable. You know, that kind of crap.

00:17:24:12 - 00:17:27:18

Luna

So I do.

00:17:27:20 - 00:17:48:18

Jack

So I, I possibly missed out on some things that I was completely unaware of. I'll tell you about my sexual debut. That happened, when I was 21. Okay. I was in college, came home for the summer, work and, you know, with my parents, working a job. One of my other friends, my good friend from grade school, high school.

00:17:48:20 - 00:18:07:04

Jack

We decided, hey, we're 21. We can go out to the bars now. So we went out with a couple, another friend and his older cousin. And by older, I mean she was like 26, 27, which relative to 21, she's an older woman. We're out at the bar hanging out. I, I don't know if I was flirting or whatever.

00:18:07:04 - 00:18:33:13

Jack

She was just really horny, and I was available, and she she suggested we kind of go on this little adventure, like, leave the bar, let's go do this thing. And I was like, okay, this is we're talking small town. So this was like 5000 people in the small town, a few scattered bars or whatever. On the next block was a building that had like businesses on the ground floor and apartments on the upper floor, like 2 or 3 apartments.

00:18:33:15 - 00:18:53:17

Jack

She I'll just call her Jane. Okay. So Jane knew the family that owned that building, and she knew that those apartments were being renovated. So they were empty. Nobody was in them. And she knew how to climb up. If you go around back, kind of climb up on this dumpster and get up here. And this was just like a I'm just thinking we're having some fun adventure.

00:18:53:17 - 00:19:15:13

Jack

Oh. Let's go. This will be sneaky. This'll be fun. Yeah, yeah, yeah. When we get up in there and we're in this apartment and then it's there's like or touching and whatever. I unfortunately don't remember a lot of the details because this was almost, well, 31 years ago or so or so. I've forgotten a few things. But we're kissing and things are progressing at some point, I don't think I wouldn't have said I'm a virgin.

00:19:15:19 - 00:19:20:01

Jack

I wouldn't have said that word. But I probably said I've never done this before.

00:19:20:02 - 00:19:21:06

Luna

00:19:21:07 - 00:19:55:09

Jack

Because I didn't feel like I should pretend like I had, I remember early she started giving me a blowjob and I remember breathing really hard, like I just run up the stairs or something. I was so sort of just overwhelmed or whatever, just like, oh my God, this is happening. And then we laid down, so we're on the floor because, like, it's an unfurnished apartment, so literally just on the rug on the floor of this apartment, we ended up having sex missionary, so I was on top.

00:19:55:11 - 00:20:17:14

Jack

I know the next day I had rug burns, my knees, and my, I lasted probably the longest I ever had gotten out that first time because I was nervous. I was like, am I doing it right? You know, the oldest, I was so in my head, just thinking about everything. So I wasn't relaxed enough to really feel enough pleasure.

00:20:17:16 - 00:20:25:05

Jack

And I remember her asking me if I had come yet. I've never asked a woman that, but she asked me that, so I. I've done that question.

00:20:25:07 - 00:20:26:14

Luna

So you know what it feels like.

00:20:26:20 - 00:20:42:07

Jack

Yeah. Not. Yeah. But eventually, you know, bit by bit, I kind of got there and I got over it and I had an orgasm, and she made a comment about, you know, she hadn't had sex that lasted that long. So I can't give you a time, I don't know if it was her know, 15 minutes, 20 minutes, half an hour.

00:20:42:13 - 00:20:43:06

Jack

It was a long.

00:20:43:06 - 00:20:47:10

Luna

Keep track of time during sex unless like, yeah, set a timer.

00:20:47:12 - 00:21:07:08

Jack

Or. Exactly. So hey, great. Had sex. We snuck down back the way we'd gotten up by that time. The bars are closed. I got in my car, drove back to my parents house in the state of mind, like, I don't know, it was a surreal. It's like everything had changed and nothing had changed. It was just like I finally had sex and it was great.

00:21:07:08 - 00:21:26:09

Jack

And there's just or at least my at the time, I thought looking back, it was not great sex. It was a great experience. Yeah, I yeah, I'd characterize it that way because it was fun. It, it it didn't have a lot of relationship stuff burdened on it. It wasn't like, oh, what are we going to do this? Should we do this?

00:21:26:09 - 00:21:44:13

Jack

What's it mean for the relationship? What is kind of close together is going to break or whatever. It was just she was horny, I guess. I was always horny. So we did it, and. Hey. Great. And, I saw her again. Just ran into her because she's a cousin of a friend. So like, years later and we didn't really mention it.

00:21:44:13 - 00:21:57:06

Jack

It wasn't a really a situation where you go, hey, remember that time, she was married by then? And. Yeah, that was those kind of. It was just sort of. It was a one night stand. It didn't even last all night. Oh.

00:21:57:07 - 00:21:57:20

Luna

Wow.

00:21:57:20 - 00:22:15:16

Jack

So, and then later that same year, in the fall, when I was back at school, I, I met someone almost kind of another one night stand sort of situation, the way it was looking to start, but that turned into like a two year relationship for the rest of my, my school time and so many of my firsts.

00:22:15:18 - 00:22:36:08

Jack

Or with her. Now we're talking mostly vanilla firsts. But, you know, first, I don't know, time with her on top. First blowjob. We we had sex in a hot tub once. That one is. I'll mention that because we were visiting her parents, and it was a hot tub in the back of their backyard, and her mom was in the house watching TV.

00:22:36:10 - 00:22:43:02

Jack

So all she had to do was like, stand up, take two steps forward, look out through the sliding glass door. Would have seen her daughter riding me.

00:22:43:04 - 00:22:47:07

Luna

Oh, damn. Wait. Like it's like inside the hot tub. Like in the water.

00:22:47:09 - 00:23:04:12

Jack

We were in the. Yeah, that's how I learned. You know, being sex in the water doesn't work so good. It doesn't work that way. The the loop. Yeah. And she was. My girlfriend was too nervous. She was like, on out. Yeah. She was just paranoid. Oh my God. So she wasn't really in the movie. But we made it work for a few weeks.

00:23:04:12 - 00:23:25:23

Jack

And so that was that was one experience. So yeah, that was that was just a really it was a great relationship. It was it was a long distance relationship. We went to to do it for in schools, or two separate schools. And so it was we only saw each other on the weekends. And it was, you know, Friday through Sunday we were having sex morning, noon and night coupled to whatever.

00:23:25:23 - 00:23:41:13

Jack

That's it was so much sex. I can't again claim it was a great sex. You know, I've learned a lot since then, but it was it was a lot of sex. It was really adventurous and it was fun. And and so that was that was kind of my, my introduction to having a real girlfriend or a real relationship.

00:23:41:18 - 00:24:03:22

Luna

Yeah, yeah. And just getting to practice. I've also come to really appreciate relationships that have built in tension in the form of distance or logistics, because it creates that, like looking forward to it. And I and I really like intensity. So I've realized that I either need a partner who can, like edge me and hold back my intensity, or I need someone who can, like, keep up with me.

00:24:03:22 - 00:24:24:13

Luna

And we have to somehow also have the time to like, exhaust ourselves sexually constantly. So it's like, I love having that built in stuff. What about, rewinding a little bit? When did you start exploring pleasure on your own? Was it with those early playboys or like, what was. And it sounds like you were, like, coming pretty fast if we contrast it with your first partner experience.

00:24:24:15 - 00:24:42:20

Jack

Yeah, that there wasn't a problem. As far as speed goes, I could come fairly quickly if I, you know, as a teenager, if I only had a few minutes, you know, that the coast was clear. I could rub one out pretty quick. Yeah. The Playboys were a part of it. Like one of the early, earliest times. I can remember trying to masturbate or masturbating.

00:24:42:20 - 00:25:02:03

Jack

I could get an erection, but not orgasm quite yet. Something was happening. I wasn't sure what was going to happen. Did I have to push? Did I have to relax? Like what? You know, was I going to pee it? Yeah, yeah, I do remember having an experience like that, but but that was pretty short lived. And then, you know, the rest of physical maturity happened.

00:25:02:03 - 00:25:27:11

Jack

I was able to, to orgasm to actually know that I, I did that fairly often. I think, there were, there were those old playboys by that time also, I don't know, there's like this sort of underground network of porno mags amongst boys of that era, like somehow you get your hands on some and then maybe you have them for a while and you get tired of them and you, you know, bequeaths them to some other friends.

00:25:27:11 - 00:25:51:02

Jack

So there were like whole penthouses, you know, from the 1970s, maybe some some other playboys, a couple of hustlers mixed in there. So that kind of magazine type porn, that's what I had access to. And I've always enjoyed from then and on to the present day. Porn. I didn't see my first, like, video hardcore porn until I was 18.

00:25:51:02 - 00:26:17:08

Jack

I think in college VHS, that's that's the first time I actually saw a video. Video sex, sex on camera, that kind of thing. So yeah, my masturbation was the the magazines help my imagination. Just my my spank bank. You know, in my head all the sexy things I'd seen, the girls I had crushes on, that sort of stuff fueled my my fantasies.

00:26:17:10 - 00:26:31:04

Jack

I don't know really how often I would say masturbated often, but I really don't know if that was every day or every couple days or whatever. I can remember thinking that. I wonder if my mom knows why she's buying so much more Kleenex.

00:26:31:06 - 00:26:32:20

Luna

So often enough to think about.

00:26:33:00 - 00:26:41:12

Jack

It so often enough that I was going through box? I don't know, it's just I was using more Kleenex than I had in the past. So that was I thought that that occurred to me. I don't know.

00:26:41:16 - 00:26:44:06

Luna

Mom, these allergies to.

00:26:44:08 - 00:26:46:11

Jack

Oh yeah. Imagine.

00:26:46:13 - 00:27:05:13

Luna

Oh, it's so funny. Okay, so so jumping back to other formative experiences, like now you're in your 20s, it sounds like you did like at least get some experience with this early girlfriend. But also, let's see, you wouldn't have been that many years until you met your wife for decades. Math? No, you two years.

00:27:05:15 - 00:27:24:23

Jack

So yeah, my 20s, the rest of my 20s. So from mid 20s to early 30s, not so great. I spent like years single and then maybe a relationship that would last a little while. I had a kind of a friend with benefits situation that lasted six months or so. That was it was pretty good. But eventually kind of got boring.

00:27:24:23 - 00:27:43:22

Jack

It was like we had sex almost on a script, like we did the exact same thing every time. Yeah. And I part of that was she was older than me, so I was around 30. She was around 40. I think in my head I just sort of expected her to take more of the lead. She was sort of that older woman like, right, teach me.

00:27:43:22 - 00:28:03:23

Jack

But I didn't say that. I never said, hey, you know, teach me or show me or whatever. So we just, we kind of got stuck in this odd rut. So that was one experience. I in my mid-twenties, I dated a virgin for a long time, so I did it through through friends. I, I, got in touch with this, woman.

00:28:03:23 - 00:28:28:01

Jack

She was a good Catholic girl. Okay. That was long distance as well. Even longer distance. It, you know, so we had to, like, check airfare to see when we could visit each other and see each other, you know, every other month or so. Kind of put together those those times, which I think is partly why it lasted as long as it did, because it took us almost two years to have enough time together to really get to know each other.

00:28:28:01 - 00:28:52:02

Jack

That's my communication was not good at that time. I wasn't clear about, like, exploring or asking. I wasn't good at knowing what I needed or wanted so much, especially in the sexual area. I thought. I thought I was chasing a relationship and in so many ways I was. My previous real relationship had been very sexual, so that was kind of the model in my brain.

00:28:52:02 - 00:29:14:19

Jack

Get relationship. Yep. Have sex. Right. And this wasn't that. I'm not sure of all her reasons for not having sex or what under what circumstances she would have started having sex. I don't know if she would have waited for marriage, or maybe if we had really committed to each other and said we loved each other. Okay, maybe that, but it never quite got to that point.

00:29:14:21 - 00:29:42:23

Jack

Okay, like I mentioned earlier, where, you know, I can have sex with someone and then the connection happens. I wonder if, because we weren't having sex, I wasn't quite getting that full connection. Yeah, that maybe I needed or would have that could have happened. So anyway, that it's kind of funny. I, I had the relationship in my mid 20s that most people seem to have in high school related that, well, you know, we're dating and should we are we you know.

00:29:42:23 - 00:29:43:06

Jack

Yeah.

00:29:43:06 - 00:29:56:15

Luna

Because because you're if your formative relationship you've experienced offered that connection because you were having sex and it kind of fell naturally into it, I can understand why a new pattern would be totally different. Did you do anything?

00:29:56:17 - 00:30:06:00

Jack

Oh, makeout sessions that lasted forever. Oh my God. We would kiss and kiss and kiss and I'd finger her. Probably poorly. Okay.

00:30:06:02 - 00:30:08:05

Luna

You don't know unless you're getting feedback.

00:30:08:07 - 00:30:26:02

Jack

Yeah. But she kept her shorts on, and there her panties. So, you know, I could get my hand in there. So. Yeah, that was. It was just kind of makeout sessions, really. That's that was sort of. We get heated up and kind of get to this certain point where it just sort of stopped, like, where would it would plateau?

00:30:26:04 - 00:30:37:04

Jack

Yeah, maybe it wouldn't necessarily stop, but it would just sort of reach that point and percolate along like that until we got tired or whatever. And like, okay, we really need to go to sleep. Yeah, yeah. Wow.

00:30:37:06 - 00:30:45:18

Luna

Okay. And so was, was that finally like, did you transition out because you were like, I do want sex or what kind of or was it just the connection? I think you'd go.

00:30:45:20 - 00:31:05:21

Jack

Yeah, I just ate it. Reached a point where I was like, I just I didn't feel the connection. I didn't feel it growing any further. It's just like there's something missing here. I didn't know what it was. I'm even now, I wouldn't say it was necessarily the sex. I don't think it was that simple. I think just some basic personality differences and whatnot.

00:31:05:22 - 00:31:21:13

Jack

It just it we weren't we weren't making that whole connection that we needed to or that would have led to more. So it just it kind of got to a point where I'm like, I need to in this. I think it's not going to go any further. So it's not worth us continuing to, to pursue it.

00:31:21:13 - 00:31:37:00

Luna

So yeah, here's a question, because I think you are the first person that has explicitly mentioned, like a long term dating relationship with a virgin. Would you jerk off to her or were your fantasies about other things in that time?

00:31:37:02 - 00:31:57:00

Jack

Good question. I, I must have masturbated while thinking of her. Yeah. And kind of reliving those those makeout sessions. Yeah. But also everything else in my fantasy life that I thought about and and porn and everything, you know, I'm sure it was masturbating all the stuff. And then she was a part of it.

00:31:57:02 - 00:32:15:06

Luna

Totally. I definitely have had fantasies about partners who I haven't, like, seen naked yet. And so I like my brain will just like fill in the gaps in these like very, very fantastical sometimes ways. And so I always just like, wonder what other people's experiences like, okay, well, what happened after that? What was your next learning experience?

00:32:15:07 - 00:32:37:03

Jack

So I think by the time I'm, you know, getting to be 30 and into my early 30s, I was I really was pursuing a relationship because that's that's kind of the only, only model I had that I felt I could pursue because I might just like, I don't do well with signals or flirting. So I even though, like my first experience was sort of a random bar hookup.

00:32:37:05 - 00:33:01:19

Jack

Yeah. That was that was lightning striking. That was not anything I could rely on. I couldn't, like go out and hookup to save my life. It's right. That was not the way I could get things started. So. So the only way I can think is to start a relationship. And. And I really wanted a relationship. So I was pursuing that, trying some dating sites, some that to really kind of led nowhere.

00:33:01:19 - 00:33:20:00

Jack

And then I started was with one and, and met my wife or, you know, hey, that started pretty quick. She, she reached out to me. We, you know, went on a date and a couple more dates and ended up, you know, dating for about a year and then got engaged and were engaged for about a year, I think, full year and got married.

00:33:20:00 - 00:33:26:06

Jack

And so, yeah, that, that from the time I met her till now is has been pretty close to 20 years.

00:33:26:08 - 00:33:36:19

Luna

Wow. Okay. So what has it been like to be with the same person for 20 years? It sounds like you've experienced a lot of growth and have had your own kind of like fluctuations in your sexuality.

00:33:36:20 - 00:33:57:11

Jack

Yeah, there's been kind of highs and lows or or lows and highs or whatever. Just to start with, things were more pretty good from a sexual standpoint. It was it was fun. It was exciting. We had sex. Not as often as I would like. That's kind of, you know, except for that sort of college girlfriend where we had it multiple times, you know, on a weekend.

00:33:57:12 - 00:34:00:06

Jack

I've always wanted more. And this was the case, but it was okay.

00:34:00:06 - 00:34:11:17

Luna

What's your ideal? What would your ideal be if your body and your jobs and your time and your partner, like, everything was like in a perfect world. Ish, right? Like, what would the roller coaster of ideal sex look like?

00:34:11:19 - 00:34:38:22

Jack

Great question. Right now, probably a couple times a week, I think. Okay, might be really, you know, just right in years past, you know, up until maybe any time before like five years ago. So throughout my 30s, 40s and I probably could have every day. And I see that from a standpoint of never actually having gotten that opportunity.

00:34:38:22 - 00:34:48:05

Jack

Yeah. Yeah. And I don't know, say, I'm pretty sure that would not be sustainable in a relationship. I don't think I could, even if my were physically capable.

00:34:48:05 - 00:34:58:14

Luna

I wonder that all the time. I'm like, well, maybe if I had like little sex and then some days with big sexes, you know, like I'm like, I'm. But I have not yet done that experiment.

00:34:58:16 - 00:35:20:16

Jack

So yeah, it's there's there's some hindsight there where I'm projecting back and wondering what, you know, in other circumstances. So but between us, you know, my wife and I was it was weekly. I was, I was okay with that. I come off a pretty long dry spell. So it was it was really great. But, you know, after the first few years or so, it tapered off.

00:35:20:16 - 00:35:48:07

Jack

It was like, wasn't every week we'd miss a weekend. We've missed a couple of weekends. It was less. It got down to like once a month or even less than that for some years. And that's where I was. I was getting really frustrated. It really wasn't often enough. I, I really I've never been one to push for it, and I especially didn't want to in this context.

00:35:48:07 - 00:36:21:23

Jack

My wife has some past trauma with being pressured. Yeah, for sex. And so I wanted to respect that and not, not always be chasing her. So we let it kind of naturally unfold. I might bring it up and ask for more, and we'd have a little bit more, like there'd be a little bump, you know, and then it would taper off again and throughout all this time, and definitely early in our relationship, I would describe it as, as fairly normal sex and and very good vanilla that's, you know, premium vanilla even.

00:36:21:23 - 00:36:37:07

Luna

I love vanilla. People get mad and they're like, why do you only like kinky sex? I'm like, that's your projection. I'm a sensualist. I like connected sex. Vanilla is a very tasty flavor. And if someone's like, they're with me, that's the best. So I hear you.

00:36:37:09 - 00:36:57:06

Jack

Yeah. So if I'm comparing, like, quality of sex between my wife and I to previous experiences, it was it was better like, this was this was really good sex. It just it was also like income. I don't know if I would say incomplete. Like I have some interests beyond just vanilla sex, like you hinted at in the intro.

00:36:57:06 - 00:37:19:15

Jack

So yeah, some anal play, anal stuff, some squirting, that sort of stuff that I knew I was interested in but wasn't and did not appear to be on the menu. And I would experience some frustration from that and then the decline in quantity as well. And so for some years there, there was, there was a fair amount of frustration on my part.

00:37:19:15 - 00:37:31:00

Jack

Like, I just it was it just wasn't going the way I had hoped it would go. And my future wasn't bright. It was like I saw a trajectory and it kind of kept getting worse. Okay.

00:37:31:03 - 00:37:43:11

Luna

Was that something you guys were able to talk about at the time, or was it sort of like one of those unspoken things? And did you have ever explicit discussions about initiation and what it should look like beyond the like, don't pressure me, babe. Talk.

00:37:43:13 - 00:38:05:03

Jack

Not really. It was it was sort of it was unspoken. I think it was mostly frustration on my part that I kept inside. We weren't like I say, we're we're much better at communicating about those things now. Early in our relationship, I was still kind of very much in my older mode of just sort of having assumptions in my head that I did not challenge.

00:38:05:03 - 00:38:06:10

Jack

Same on my own.

00:38:06:15 - 00:38:11:20

Luna

Well, and it's like, and I need an example or a partner who initiates or I don't know how to do it, you know.

00:38:11:22 - 00:38:28:07

Jack

Yeah, I've always kind of had this sort of expectation that and it's probably me projecting my enthusiasm onto others and expecting that they're going to meet me at that same level. Yeah. And when that's not there, I'm kind of like, And that was.

00:38:28:09 - 00:38:30:13

Luna

I totally get it. Yeah.

00:38:30:15 - 00:38:34:23

Jack

You know, and now I'm learning that, oh, I can ask for this. We can talk about it.

00:38:35:03 - 00:38:35:16

Luna

And we.

00:38:35:16 - 00:38:44:04

Jack

Can decide what we want to do. You know, I had it. So finally cluing in. Yeah. You know, after after a lot of years.

00:38:44:06 - 00:38:49:10

Luna

When did you lose your sex drive. Like, is that was that part of the frustration moment or did that come later.

00:38:49:12 - 00:39:14:17

Jack

It came a little later. So this was probably in my late 40s. So I'm 52 now. So we're talking, you know, five years ago or so. Yeah. Yeah. And I noticed my sex drive declining in a way that it never had before, like from puberty to my mid 40s. So I had a good like 30 year run of just relentlessly high interest in sex.

00:39:14:18 - 00:39:34:12

Jack

It might vary day to day. I might have, you know, a an off day or an off couple days or something, but it would, it would bounce right back and I just, I'd be interested. But in my late 40s, it started like those little downs stayed down. And what I would describe is still maybe a medium interest in sex.

00:39:34:12 - 00:39:59:02

Jack

Like, okay, I'm interested, but it's not really top of mind. And, you know, some day to day variation. But overall it was a downward slope and not, you know, yeah, I'm getting older. Things aren't what they used to be sort of decline. It was like, this isn't right. Like something is you know, it was definitely a progression downward that had me concerned.

00:39:59:04 - 00:40:23:00

Jack

I was like, okay, what's going on? Am I not getting enough sleep? You know, I looked at some of those general health things in life. What's going on? I tried to fix those things. I didn't really see much in the way of results. I thought, well, maybe it's work stress because at the time I was involved in a project where I had a whole lot of responsibility trying to get things done per schedule and no authority to actually make things happen.

00:40:23:05 - 00:40:24:19

Luna

Oh, that's stressful.

00:40:24:21 - 00:40:42:04

Jack

And it was overwhelming. And so that was that was kind of constantly on me. I thought, well, yeah, it could be that that makes a lot of sense. But it took some time like a year or more for that project to start to wind down a little bit. And then I was able to switch. I'm still at the same company.

00:40:42:06 - 00:41:00:20

Jack

I moved to a different project, and when you're the new guy on the project, you're just expected to you're learning mode. You're not responsible for anything yet. You got to get up to speed and then take on some work. So the expectations at first are just sort of, you know, learn some stuff. My stress level therefore was was dropped.

00:41:00:20 - 00:41:23:11

Jack

It was like nothing. I'm like, oh, you know, that load is off. That feels great. My sex drive still dropped, still was down, was not getting any better. I'm like, oh crap. Okay. What's what's going on here? My next best idea was maybe, hormones. Like testosterone was was maybe down, symptoms off. So then I started. Okay, I got to start seeing doctors.

00:41:23:11 - 00:41:41:09

Jack

This is probably a medical problem of some kind. A couple of months spent trying to get some insurance stuff straightened out, go to make an appointment. Takes two months to see my primary care doctor. I finally get to see her. She asks all sorts of questions about, you know, like saying, like, hey, my sex drive is dropping.

00:41:41:11 - 00:41:59:18

Jack

What could be going on? She has questions about, like, how often do I get erections? Do I get erections at night? Just sort of sexual function type questions. Did a blood test to check for all the kind of usual health things could be thyroid, diabetes, whatever I check out. You know, I'm in pretty good health overall.

00:41:59:20 - 00:42:18:05

Jack

When I mentioned that my low sex drive was leading to erection problems. Because imagine that when you're not interested in sex at all, it's a little hard to get an erection. So she immediately she offered Viagra right away. And I was like, but that's not really my problem. But, you know, okay, I'll give it a try. Right. And and I'm glad I did.

00:42:18:05 - 00:42:29:02

Jack

It helped a lot when my sex drive was low. I could take Viagra and then not have to worry about it. That was like, off my mind. And that's all Viagra does. It makes it easier to get an erection.

00:42:29:02 - 00:42:29:12

Luna

It does.

00:42:29:12 - 00:42:33:04

Jack

Blood flow inspire desire in anyway.

00:42:33:06 - 00:42:51:21

Luna

So and it doesn't squash anxiety for all the people are like, I'm nervous, I'll just get a boner. And it doesn't increase connection with partners and it doesn't make you a better lover. It just allows blood flow to increase and state your. I mean, a cock ring is more effective at keeping the blood flow in your cock, but like, yeah, it initiates that.

00:42:51:23 - 00:43:16:02

Jack

And I tried cock rings as well in those helped. So but yeah the library to help with erections. But the sex drive was, was of course untouched by that. The, the blood test for testosterone came back and there's a huge range that's considered healthier, normal or whatever. Yeah. And I was at the bottom of it. I was like fifth percentile.

00:43:16:04 - 00:43:24:15

Jack

And I'm like a Like, I'm on to something here. I was right, and I asked her about that. I'm like, is it the hormones? She's like, I know you're in the range. You're fine.

00:43:24:17 - 00:43:38:05

Luna

Oh, okay. Well, also, did you have a baseline from the, you know, from years of previous. Yeah, exactly. And also just that there's so many things where they're like, no, you're in the normal range. And it's like, context is important, you know.

00:43:38:05 - 00:43:53:02

Jack

Exactly. So I'll just I'll throw out a I'm not a medical professional, but yeah. Yeah, man. If you do, I would recommend getting your testosterone checked at some point in your 30s. What if just get a baseline. Get a number. Yeah.

00:43:53:04 - 00:44:05:13

Luna

It's not just testosterone like baselines for our health or in the like. There are so many, like, even at home testing kits now you can do. And the Huberman lab has very good recommendations for this sort of stuff.

00:44:05:15 - 00:44:24:08

Jack

So that, I mean, that I was sort of like, but to immediately offer to refer me to, the urology clinic, so I'd see a specialist instead of, you know, a generalist. I'm like, okay, good, let's do that. Wait another two months, you know, to get that appointment. Yeah. See a doctor who's an endocrinologist. So hormone doc, I'm like, all right, here we go.

00:44:24:08 - 00:44:48:05

Jack

Here's the expert. Same questions again. You know, maybe a few more questions. A little more in depth, physical exam. And at the end of that, he was like, well, you know, these things can be complicated. Would you consider seeing a sex therapist? And I was like, well, okay, I, I would, you know, like, just like, that wasn't kind of what I was expecting.

00:44:48:05 - 00:45:03:20

Jack

And the way it was, it was delivered like he said that. And then, you know, I was given a list of sex therapist that would take referrals from them. And that was kind of it, like there was no hey, for men your age, you know, it can be mental. There can be mental factors, there could be physical factors.

00:45:03:22 - 00:45:13:09

Jack

Yeah. You know, I recommend you see a therapist. They can really it was like no endorsement whatever. No information about it. Just like punt like I don't know what's wrong with you. Go try this other thing.

00:45:13:09 - 00:45:30:12

Luna

Yep. Well, and a lot of doctors are not required to have any sex ed necessarily beyond the biological. And so bedside manner of like their shame isn't magically solved, like just because they are in this position of power where we're like, please hold me. Like not covered necessarily.

00:45:30:12 - 00:45:45:06

Jack

Yeah. So and I tried to to supply the like the background, like why I'm here. And I went through the whole story about my work stress and why I didn't think there were there were mental factors, or at least not that one involved. And I asked about the testosterone level. And again, I was like, no, you're in the range.

00:45:45:06 - 00:46:03:08

Jack

You're fine. And I was. So I left that appointment. And the more I thought about it, the more frustrated I got. Yeah, I spent six months doing it, and I was no closer to any kind of a solution than I had been. I started, you know, during this time I was doing online research as well, and I kind of dive back into that.

00:46:03:10 - 00:46:27:10

Jack

And there are clinics out there. There's these men's clinics, testosterone clinics, whatever that will. They kind of cater to that. But especially the online clinics are kind of flaky. I found a lot of fake reviews there. Yeah. They're really marketed toward the gym bro culture where like, dude, you can't pump iron like you used to here. You know, take some testosterone and you'll improve your recovery time and all that.

00:46:27:12 - 00:46:50:03

Jack

For guys that are 30 and wish they were 25 still or something. And I'm like that, that doesn't appeal to me. That's not my problem or not. There you know, but there were some clinics in my area and actual physical sort of men's health clinics. So I'm like, all right, I'll try this. So I went to I made appointment, I went to one of those actual physical location talks, the doctor, they see this kind of stuff all the time.

00:46:50:03 - 00:47:10:20

Jack

They listen to me a little better. Still, the same questions again. And this time these. I mentioned the earlier blood test and they were like, oh no, that that test was taken at noon. No, we want to accept that testosterone should be checked in the morning. Because your levels are highest in the morning and then they taper off.

00:47:10:22 - 00:47:42:23

Jack

And also two tests on two separate days. Because this stuff varies. It varies from day to day. It varies. So they wanted to test in the morning. So I did a couple more blood test. And that time I came in and I was just below the line. Not that the line super mattered to them, right? They were more listening to me about my symptoms because, you know, like the the endocrinologist that I talked to, again, all these questions were comparing me to some standard, I don't know, all men, all adult men, men my age, men who limited data.

00:47:43:00 - 00:48:04:14

Jack

These dudes. Yeah, yeah, experiencing. And I was in there because relative to my own experience. Yes. Just a few years ago. Like, yeah, I still occasionally get an erection at night, but five years ago, I used to always get erections at night to the point where it might disturb my sleep. Like I'm kind of tossing, turning, trying to get comfortable because my dick's hard all the time.

00:48:04:18 - 00:48:25:22

Jack

Yeah, you know, this was a major change for me, and none of that got really listened to or accounted for in any way. So, but so I went to the clinic and they tested me the right way, so. Oh, no, you're low. So I started on testosterone replacement therapy, and they start you pretty low just to check.

00:48:25:22 - 00:48:46:23

Jack

And you get blood tests fairly often at first while they dial in your dose. Yeah. The effects aren't like flipping a switch. You know, they they build up over time. It's like they said, it's kind of like filling a sponge. That has to progress the for the first month or so, I didn't really notice anything. By the second month.

00:48:47:01 - 00:49:07:08

Jack

I think what I noticed first was more sex dreams. The sex dreams came back. Oh, and those were happening. And in that first six months, I was having sex dreams like a couple times a week. And that's not even before throughout my life, that's a lot more than okay than was typical. Like I have occasional sex dream, like it's a few months go by, but this was okay.

00:49:07:10 - 00:49:26:01

Jack

They were fairly consistent. Oh wow. And so just my overall interest like I'm I'm noticing women more. I'm checking out like, oh hey, she's hot. Hey, I think she's hot. I didn't think she was. You know, a few months ago I would have been like, whatever, you know? So it was it was definitely growing. It was coming back.

00:49:26:03 - 00:49:48:15

Jack

And now it's been like two years, I think I've been on TRT and I continue with that. I think there were some other factors that helped. There was some other kind of relationship stuff that I don't want to go into that was like kind of had me. It wasn't stressful in the way work was stressful, but it had me frustrated and angry a lot.

00:49:48:17 - 00:50:10:21

Jack

And I think that was I'm sure that was a factor. I don't know if it was a causal factor or if it was a contributing factor. All this stuff is so complicated. Yeah, it is with hormones and and all the things that can go into it, I don't know, but it did it did get better. So overall, I think between the hormone intervention and other things in life, I'm I'm back.

00:50:10:21 - 00:50:35:00

Jack

I'm not quite the my old self. I can't say that my sex drive is is high the way it was in my 30s. It's not, you know, that relentless kind of hunger or urgency that's on my mind the way it was. But it's pretty good. And in some ways, if I'm trying to be honest with myself, that's maybe better in some ways, because with sex on the brain, constantly, you can.

00:50:35:04 - 00:50:40:12

Jack

It's just it's distracting. Like, I get it. I need to pay attention to dude.

00:50:40:14 - 00:50:48:08

Luna

It can cause a person to make some pretty wild life choices, just speaking from experience.

00:50:48:10 - 00:50:57:18

Jack

So having some relief from that is probably beneficial. But I also kind of miss my old self in that way.

00:50:57:20 - 00:51:16:22

Luna

I know I'm listening. I'm like, I gotta go, okay, before I change, I gotta find someone. Okay. And then I'm like, okay, divine timing. It's all good. How do you feel this experience affected your communication? Like, I would love? I would be so curious to hear how it paralleled or kind of dovetailed with the communication that it sounds like is.

00:51:17:03 - 00:51:18:11

Luna

Yeah, an ongoing I.

00:51:18:11 - 00:51:44:20

Jack

Would say this this really kicked off communication with my wife and I in a, in a big way because. Early on when I, when I thought it was work stress and that sort of stuff, I hadn't talked, to my wife about that. It hadn't really affected our sex in any way. Maybe my erection wasn't quite as quick or quite as hard.

00:51:44:20 - 00:52:06:21

Jack

It was subtle signs like that that I was aware of. It, that she probably wasn't. I was just kind of working on it, trying to get it fixed when I, I made the first doctor's appointment, and then I was going to bring that up because like, hey, I have this doctor's appointment, I, this is what's going on.

00:52:06:23 - 00:52:27:00

Jack

But before I could start that conversation, one day, she wanted to have sex, and I'm like, oh, okay. And it was on one of my days when it was like, gone. Like not just low, but like I had nothing. And I'm like, okay, let's let's see if something catches on. And it was we were in the bedroom or whatever.

00:52:27:00 - 00:52:49:21

Jack

Then I'm like, now this, this isn't going to happen. Like at least as far as an erection. I was not going to be able to get an erection because my desire was so low. I just wasn't interested. And so I was like, this is what's going on. And she was super understanding, like, so such a great reaction to this really, instead of like, well, you know, we can we can work around it.

00:52:49:21 - 00:53:07:22

Jack

And I was perfectly willing to continue. We could play, you know, just because I couldn't get an erection wasn't the stop. You know, I can lick her pussy just as good. And I was willing to do that, but instead it just turned into a conversation like we talked about this and she's like, oh, yeah, she understands hormones. Yeah, she's had some of her own health issues.

00:53:07:22 - 00:53:33:02

Jack

And and so that turned into, you know, a really good conversation that that sort of kicked off. What's going on with me health wise and sexual lives. I'll also say that having this experience of kind of, you know, having lost it and gotten back, it's one of those that you take for granted. You totally take stuff for granted until it's like slipping away.

00:53:33:04 - 00:53:58:02

Jack

And then if you're lucky enough, like I am, and I consider myself super lucky to have gotten that back because it was it was such a, I finally realized how important it was to me, like, yeah, in the past. Okay. Yeah, I, I want sex, I like sex, it's a lot of fun. Yeah. Sex. It's great. I didn't realize its importance in a way.

00:53:58:02 - 00:54:22:10

Jack

And and I'll, I'll kind of, I guess use an analogy like you can ask anyone what their favorite food is like. What's your favorite? Yeah. Oh yeah. Then they can answer that. Favorite food. Yeah. But with some people, like, they like to talk about food. They like to read about food. They like to think about food. They they'll travel someplace just for the food, like around the country, around the world, because it's important to them.

00:54:22:12 - 00:54:46:11

Jack

Yeah. And I finally realized that sex is important to me in that way. And it's important to my, my mental health. And if, if that's lacking or if something's like not right with that, then then I suffer for the lack of it. So that's, that's like one of the big sort of lessons overall that I gathered from this entire experience.

00:54:46:13 - 00:54:48:06

Luna

Wow. That's huge.

00:54:48:06 - 00:54:51:08

Jack

So did the.

00:54:51:10 - 00:55:00:07

Luna

Butter explorations and the squirting in the fantasy achievement come before or after or throughout? Like where where did this your challenge? Okay.

00:55:00:07 - 00:55:21:00

Jack

Yeah. The squirting is is a kind of a quicker story that that just happened. A random that was unexpected. So that's quite a few years ago. Yeah. It was I, I was going down on her. I'm licking her clit. I have, I think a finger in her pussy. And when she reached orgasm, I felt just a little squirt.

00:55:21:00 - 00:55:40:00

Jack

That's probably the right word. Just on my hand to the point where it's like, I wasn't sure. Like, was that was that a squirt that she. And so I was like, okay, sort of filed that away. I like I want that to happen again, but I didn't know how. And some months later, I think similar scenario. And that time it was definitely a squirt.

00:55:40:00 - 00:56:01:11

Jack

Like I felt like I got totally wet chin on my chest, like she squirted on me. It was definitely liquid at my my immediate response was, was enthusiasm. I was like, yes, you squirted. This is awesome because I, I well, I wanted her to know that this was a huge turn on for me. Yeah. And also that I didn't want her.

00:56:01:11 - 00:56:21:16

Jack

Oh my God, did I just pee on him? I didn't want her to, like, suddenly tense up, wondering what. So I was like, hey, this is what happened. This is awesome. And from that we we got a waterproof blanket, one of those, I think, from Liberator. We have also some other cushions or those wedge shaped cushion.

00:56:21:17 - 00:56:22:06

Jack

Yeah.

00:56:22:07 - 00:56:25:05

Luna

Oh, I want those. Do you like them?

00:56:25:06 - 00:56:49:01

Jack

Yeah, they're they're good for, like supporting angles and, and things especially with, with me and missionary on top. If I can use one of those wedges lift her up just a little bit. It proves the angle. It's. Yeah. It's really good. Yeah. And with like the, the blanket, there's no worrying about this. It's like because that was I think she had to be like really turned on and really relaxed.

00:56:49:01 - 00:57:05:22

Jack

And if she was worried about making a mess, it wasn't going to happen. Yeah. So with the blanket, you know, it's it's there. You know we don't have to worry if it happens. It happens. It's great. We love it. So that's something that happens kind of occasionally whatever, when it's the right combination of factors. And I love it.

00:57:06:01 - 00:57:21:01

Jack

It's it's been a, Yeah, a big, big turn on for, for me. And, and we both enjoy it. She knows I think for her she like seeing my reaction. She likes seeing how much it turns me on. So that's what gets her excited as well.

00:57:21:03 - 00:57:23:16

Luna

That's amazing.

00:57:23:18 - 00:57:46:18

Jack

So the the butt stuff. So for this, we maybe we go all the way back to the beginning. So I don't remember when I first learned about anal sex, anal penetration. It's that moment is kind of lost on me that the earliest memory I can point to is having a conversation with a friend of mine in the eighth grade, so we must have been like 13.

00:57:46:20 - 00:58:07:03

Jack

Yeah, talking about anal sex. Somehow on the playground, he was like, oh, gross, I'd never do that. And I was like, oh, well, I would or, you know, my answer was like, well, I would if if the girl wanted to. That was kind of the way I, I waffled a bit. Yeah, yeah. Because you have to be careful, you know, one minute you're telling your friend, you you totally want to do Anglo-Saxon.

00:58:07:05 - 00:58:21:00

Jack

You know, by the end of the school day, your new nickname is butt lover or something. So it's like, okay, you know. Right. And it was also one of my first experiences with realizing that there was something I was really turned on about, something that excited me. And another person was like, oh, gross.

00:58:21:02 - 00:58:21:18

Luna

Yeah.

00:58:21:18 - 00:58:56:08

Jack

Good point. So it was like, oh, oh, right. Okay. I probably learned about it through Penthouse Forum. Okay. That's my best guess, because there were stories about people having anal sex, and I would have been like, oh yeah, well, that sounds like fun. And throughout my, my porn watching or reading or whatever, I gravitate toward that. It's not exclusively what I, what I seek out, but it's a significant portion of the, the fantasy material that I, I've, you know, sought out over the years is is some kind of, you know, anal sex.

00:58:56:10 - 00:59:15:17

Jack

Yeah. With a girlfriend in college, we had a couple attempts. We did not know what we were doing. Yeah. Didn't know how all of this. I think she knew I was interested, so one time, she just kind of moved me from the front to the back, and I tried to push in. I got the tip in. It was truly just the tip kind of a situation.

00:59:15:17 - 00:59:38:13

Jack

I was so excited, I came. Oh, wow. It was it was one of my probably the closest, you know, experience I've had with premature ejaculation in some way, or coming before I want to was like, because I was so turned on insert button. Yeah. And, we tried it one more time. I think I got a little deeper that time, probably just as well, because with no lube or anything, it probably would not have gotten.

00:59:38:15 - 00:59:40:07

Luna

Lost in my growth areas. Yeah.

00:59:40:09 - 01:00:00:05

Jack

Yeah, I don't count that as having had anal sex. It was it was an attempt. It was a couple tries at it. After that I tried learning more. I got, at some point I found Tristan Tarantino's book, The Ultimate Guide Anal sex for women. Great. So I read that it's like, okay, here's the information. And I just I was so into it, interested in it.

01:00:00:05 - 01:00:27:05

Jack

I thought, you know, at some point it'll happen sometime in the early years of our marriage, my wife offered to try it and I was like, yes, all right, here we go. But I knew, like, okay, lube, you go slow. You know, there's prep for these things, you know? So I did those things and, and we started and she was nicely relaxed and I slipped right in and almost immediately or a couple strokes and she's like that now, not working whatever and done.

01:00:27:07 - 01:00:47:13

Jack

And I was like, okay. So all right. And attempt we'll, we'll try it again some other time. So we just, you know, I had a condom on I think I because for cleanliness I took that off and so clean. We can continue with regular and vaginal sex. And because she brought it up that first time, I just kind of for some reason expected she would like bring it up again.

01:00:47:13 - 01:01:13:17

Jack

Like sometime later. We, we try again and and that didn't happen. And then I'm like, oh, it's maybe because she tried it didn't like it done. And I'm like, oh, I should I ask, should I risk getting the answer I don't want to hear. And so I let that be the status quo for a long time, because I was I was afraid of asking the question and then getting shut down in a marriage that's, you know, pretty good.

01:01:13:17 - 01:01:34:04

Jack

It looks like it last. There is no next, there is no future relationship. If it doesn't happen in this one, it doesn't happen. And so I'm like, but eventually it's, it's such, such a turn on, such a fantasy that I couldn't really let that go. And at some point I tried to, yeah, I it's my birthday coming up.

01:01:34:04 - 01:01:53:08

Jack

And could we try this again? And and her answer was basically no. And we talked about it and it was a nice conversation. It was short, but it was kind of like, no, that's really not my my sexuality. She was like, no, sorry. And I was I was crushed. I was devastated because that was the know that I didn't want to hear.

01:01:53:09 - 01:02:20:17

Jack

Yeah. And so I, you know, okay. Back to fantasy. Whatever. But my engineering brain is a problem solving brain. And if there's a problem, there's solutions. And I'll consider all the solutions, whether they're good solutions or bad solutions or whatever. If it's, you know, anal sex admits that's something to at least consider. So, you know, there's there's not a lot of solutions that I could come up with.

01:02:20:18 - 01:02:40:13

Jack

But the one what if what if I saw the professional sex worker, what if I went to an escort? And how would I do that and wonder what it's like? Just normal. And so I kind of had that in my brain for a while. I will, I'll do research. So I procrastinated. I'll do research on this. And so I learned more about professional sex work.

01:02:40:13 - 01:03:07:23

Jack

I found escort ads. I, you know, I kind of dove into that or read blogs and articles and things, podcasts, whatnot. And so I got much more knowledgeable about it. But still I was like, oh, what? What do I do about this? The the ideal way forward for me, kind of the perfect solution would be that if, you know, I can talk to my wife about it, suggest this, she could be okay with it.

01:03:08:00 - 01:03:28:14

Jack

And then and sort of some little version of ethical non-monogamy. Maybe I could go achieve this fantasy. Yeah. And once I decided that, I was like, okay, I'm going to talk to I'm going to bring this up, like, how do I bring up that conversation? Because it's not like, hey, do we need anything at the store? And oh, do you mind if I go by fucking escort?

01:03:28:16 - 01:03:37:01

Jack

You know? That's not going to happen. Like, it's it's gotta bring this up at the right time.

01:03:37:04 - 01:03:38:20

Luna

Yeah, yeah, in the right way.

01:03:38:22 - 01:04:00:23

Jack

Yeah. So, I mean, eventually I was one of these conversations after sex. So we'd had a good day, we'd had sex that day and I was feeling good. And so I finally brought it up. And the way I approached it was not, can I go do this? Not a permission request. It was. There's this fantasy, this thing I've wanted to do.

01:04:00:23 - 01:04:19:05

Jack

I talked to, you know, I kind of shared the stories I just shared with you. I, I talked about my my history with that. She knows I'm into it with the porn. Occasionally watch porn together as a treat. And so if I get to choose, well, I'm like, choose a scene with anal in it. So I came at it from, here's this thing that I really, really want to do.

01:04:19:05 - 01:04:43:22

Jack

I've always wanted to do it my whole life and I see a solution. So I just want to start the conversation about what if I were to go achieve this fantasy with an escort? Her reaction surprised me a bit in that she said no, but the her answer was basically like, well, I would rather you do that with me.

01:04:44:00 - 01:05:01:05

Jack

So she was saying that we could do it, and I was like, yeah, Like it took a minute for my my brain to reorient because I was 100% certain that she was never going to do this. Yeah. Basically said that some time, years before. And so I was like, it took me like, wait, you're saying you'll you'll try it?

01:05:01:05 - 01:05:19:07

Jack

Like what you're, you know, so there was a couple minutes there of me just not grasping it until finally were like, oh, okay, well then we'll try it. And then I went back into research mode because now I'm like, I've never done it before. I'm a beginner. She's never done it before. She's a beginner. I don't want to screw this up.

01:05:19:09 - 01:05:45:15

Jack

I want to do it right. So I reread Tristan's book, you know, because it's been a while now. There's there's YouTube videos and there's podcasts and there's all information out there if you seek it. So I, I did all that and, and my wife was that's kind of the, the most she's, she's very willing to let me do the research and then lead her along like I'll go do whatever, I'll figure this out and then I'll, I'll convey that information to her.

01:05:45:15 - 01:06:04:17

Jack

And she's not going to dive into the research herself for this. You know, I could share things with her, you know, an article, we could watch a video together or something. But mostly she's sort of relying on me to take the lead. Okay, so I did that. Okay, then we need toys. We'll we'll start with that. I bought the starter kit, the butt plugs.

01:06:04:17 - 01:06:34:07

Jack

You know, the little one, the medium one, the larger one. I bought some anal beads. I bought a vibrator. Not necessarily for the butt stuff, but just because we're buying sex toys, let's buy a bunch of toys. The lube, the right lube, the. It'll go with the toys. And then we spent probably a few months exploring, like just trying a finger try a toy, a little bi plug, you know, and sort of working our way up until, like, okay, like this this weekend is what are we going to do?

01:06:34:07 - 01:06:52:14

Jack

The we're going to do the look. Okay. Yeah. Let's go this weekend. You know. So we had a few days of anticipation for that, which was great. So we're building up to that. And I'm I'm, I'm really nervous about like I want it to go well so badly. Yeah. And trying to do everything right however, you know, whatever right is.

01:06:52:16 - 01:07:15:06

Jack

But it would. So we do, we start having sex, we use the butt plug to kind of structure out a little bit, and then finally we go for, you know, penetration. And we take things really slow. I start with just a little bit and I pause. How are you doing? Okay. We're good. A little deeper, you know. Again, I pause once I'm fully penetrated and just hold there, ask her how she's doing.

01:07:15:08 - 01:07:37:12

Jack

So good. Okay, I can start moving. So kind of short, slow strokes build up to the. From there, she, she had a vibrator that she was using on her clit. So we're at doggy style, like, she's she's kneeling on the bed and I'm standing next to the bed behind her, because that gave me kind of the best balance and control I could really just stop or move a little bit.

01:07:37:14 - 01:07:56:11

Jack

So she's using the vibrator on her clit and and I'm in her ass and it's it's going really well, and she has an orgasm and I have an orgasm, and it just it was it really couldn't have gone better. It was it was just amazing. Like it was not only a first experience but a good first experience.

01:07:56:11 - 01:08:18:12

Jack

Amazing that oh, we've done it a few times since. So this was just like earlier this year, like at the start of these. Oh Josh. So finally. Well I was I was 51 at the time so it took me 40 years. Yeah. From the time I first learned that anal sex was a thing and I wanted to do it to finally, finally achieving that.

01:08:18:14 - 01:08:42:09

Jack

And, and I just I felt so great about that. We just we did again this last weekend, and it was better than, than the, it just so that's it's just it's a new thing now. There's, there's new things on the menu. There's, there's yeah, there's there's growth, there's there's fresh horizons. Where in those middle years I was very pessimistic and it looked like there was going to be less and less.

01:08:42:09 - 01:08:58:12

Jack

And now there's more and more. And I at some point we'll we'll explore the territory. We'll figure out where our boundaries are, the new constraints, maybe things will plateau. But right now they're they're growing and it's great and growing in ways that really it couldn't have gone better for them.

01:08:58:14 - 01:09:06:05

Luna

Oh my gosh. Okay. Well on that note, it sounds like there's some growing in the direction of what stuff that doesn't have to do with squirting.

01:09:06:07 - 01:09:26:17

Jack

Right. So I've also always interested in some form of, of play or this is kind of where the voyeurism comes in because I mentioned that, okay, I'm very visual and that's sort of the stereotype. Men are visual. I am very visual. So from a, from an early age who was, you know, seeing I'm very attracted to the feminine.

01:09:26:18 - 01:09:28:13

Jack

So women just capture me.

01:09:28:18 - 01:09:30:06

Luna

They're very beautiful.

01:09:30:07 - 01:09:54:16

Jack

And I can remember even as a teenager or like say, you know, in high school when you're out drinking or whatever, somebody get some beer or whatever, you know, camping is sort of drinking in the woods, like, or, you know, somebody get some beer and the place to party is, you know, someone knows of a dirt road, you can go down and, you know, you can all have some beers, have a campfire or whatever.

01:09:54:18 - 01:10:11:19

Jack

So if you're doing that in mixed company of the girls would get up maybe, and they just step out of the firelight, they go pee or something or step behind a car. And that, that intrigued me. It was like I wasn't just, okay, they're going to to have a pee or whatever. There was. There was some part of me that was more curious than that.

01:10:11:19 - 01:10:30:08

Jack

Like what's there was some draw. There was like a sexual tension. And if it was happening out of the corner of my eye, I'm like, I'm not going to be the jerk. I'm not going to stare. But I want to like, there's there's something weird. And at that point, like, I didn't know if that was a common thing.

01:10:30:12 - 01:10:50:00

Jack

It was sort of like, I'm into this. Why is this exciting? You. This is weird. I think at some point I caught on to some porn that was along those themes that would have been written like bad stories on the internet, kind of, you know, or poorly written stories, I should say that explored that. I'm like, oh, but there's other people that are kind of into this.

01:10:50:02 - 01:11:09:10

Jack

Oh yeah. So it started from that kind of wanting to watch that, that voyeuristic, aspect. I also think this is one of those where I missed an opportunity, the that college girl friend we'd be in. We haven't makeout sessions or whatever fooling around and she, she'd say, oh, I have to go to the bathroom. Better let me up.

01:11:09:10 - 01:11:25:02

Jack

Real pee on you. And, whatever. We keep making out and, you know, eventually we choke. And then I'd let her get up and go. Go to the bathroom. And then sometime later, you know, again, years later, I was like, sort of learn more about this fetish. I'm like, damn it. I think she was she was hit.

01:11:25:04 - 01:11:27:02

Luna

I mean, I didn't know till, you know.

01:11:27:04 - 01:11:45:23

Jack

Yeah, either one of us was new enough or was willing to take that step. Right. And to do anything she would, she would, she'd use the toilet when I was in the bathroom, like brushing my teeth or whatever. And that was kind of a moment like, yeah, like something's going on here. But they didn't. It didn't really turn into anything.

01:11:46:01 - 01:12:05:18

Jack

So, you know, internet porn comes along and I realized, oh, this is pretty common. Like, yeah, people are adding to it in different ways. For some folks, I suppose it's a, it's a humiliation kink. They could really lean into that, like, oh, this is gross. This is disgusting. Whatever. And play with that for, for other people, it's like a wedding and a desperation thing.

01:12:05:21 - 01:12:29:15

Jack

Hold it tight. Games I've seen, you know, porn related to that. So I kind of got familiar with this, this whole thing. And there's common enough like that. There's whole porn websites dedicated to this. So that's kind of how I've explored it so far is is through watching videos. I would like to feel it on my body at least I think that would be a very.

01:12:29:21 - 01:12:38:00

Jack

For me, it's more of a a sensual, erotic experience. Yeah. Not a sub dom kind of degrading experience, at least.

01:12:38:01 - 01:12:40:00

Luna

That's kind of very intimate to person.

01:12:40:03 - 01:12:58:22

Jack

Yeah, yeah. So that's kind of the way it would. Yeah, it does turn me on. I haven't brought this up directly with my wife. At some time soon here, I think I will because if it's, if it's squirt or if it's pee, I know there's, there's videos out there and debate and people that say, you know, well, it's this or it's that.

01:12:58:22 - 01:13:19:14

Jack

It's like, I don't care so much, whichever it is okay with it. Yeah. You know, so so that's something to explore. I think I'll, I'll bring that up and we'll see that I that could really be the boundary there. I don't, I don't know it could be the extent where you know, maybe she'll just let me watch. Like she would be willing to do that for me.

01:13:19:14 - 01:13:31:13

Jack

I doubt if she's really going to be into it. Yeah, in the way. But I don't know. We'll we'll get there. We'll see where the where the explorations lead. So yeah. Yeah. That's that's kind of a, a future horizon.

01:13:31:15 - 01:13:51:16

Luna

Also relationship creates really interesting turn ons in my personal experience. Like piss play is not something I ever would have explored just on my own. And for me, my first exploration was through a power dynamic. But also it just went both ways and it was sort of like we just wanted to try a lot of stuff, you know?

01:13:51:16 - 01:14:10:14

Luna

And so it and it was really edgy for me. And, and and then I realized I, you know, I was like, oh, whatever. But then I met someone more casually and then let that person be on me casually and I and then I realized, I only want to do this with someone that I'm really, really like into, you know, like, like in a personal way, because I was like, oh, this is how I discover it's intimate.

01:14:10:14 - 01:14:20:03

Luna

And so it's like one never knows. I've heard from many people that the biggest barrier is, is like shyness, like being shy.

01:14:20:05 - 01:14:21:02

Jack

Oh, yeah.

01:14:21:04 - 01:14:39:17

Luna

And so and so I find that fascinating because I don't have the same shyness or my, my shy lines are giggled differently than a lot of peoples. And so, I think it's just, I think it's cool that you are. Sounds like building up to talking about it more. And I mean, even just watching this is really fun.

01:14:39:17 - 01:14:54:23

Luna

I did have a lover that wanted to see he didn't want to get peed on, but he wanted to watch me pee. And he wanted like a whole tutorial of my pussy and see urethra versus vagina versus, you know, all of that. And I'm like, totally, that's so nerdy and hot. And then he wanted to watch me pee.

01:14:54:23 - 01:15:02:18

Luna

So we have the shower and then once I was peeing, he's like, actually, can I touch it? Like. And I was like, yeah, I was like, hurry up. Because, like, I can.

01:15:02:18 - 01:15:04:01

Jack

Only do this.

01:15:04:03 - 01:15:14:04

Luna

For so long. Yeah. You know, I was like drinking the water. So that's, interesting. Okay. Well, I will be curious as to how it unfolds.

01:15:14:06 - 01:15:34:23

Jack

Since I had kind of explored the escort sex worker thing, and it ostensibly and my, my impetus for that was, was to achieve my anal interest. That's taken care of now. Yeah. But while doing that research, you know, if you see the escort ads or whatever, many of them are very upfront about duo sessions.

01:15:35:01 - 01:15:35:09

Luna

01:15:35:11 - 01:15:56:14

Jack

That's like, oh, a threesome like, oh because I've never had that experience. Of course I would really like to. And I'm like that's got to be like one of the best ways to do that is with two professionals. So at the same time I was thinking that maybe this is an avenue to anal sex. The other things were cropping up like that, like, oh, could I have a threesome or whatever?

01:15:56:16 - 01:16:16:10

Jack

Now that the the anal thing is gone in a different direction. And so the, the, the really seeing an escort isn't sort of on the table anymore, but still as my wife and I talk more and explore more, maybe we'll come up against some of these boundaries or some areas where it's like, there's a thing I really want to do, and she really doesn't.

01:16:16:12 - 01:16:26:15

Jack

Yeah. Then maybe we can explore that idea again. And if it does open up, then that is that's of course, something I would love to do is to have a threesome with, with two lovely professional ladies.

01:16:26:21 - 01:16:31:18

Luna

Oh, it can be. I mean, you get the right mixture of people. I think it can be really amazing.

01:16:31:20 - 01:16:37:06

Jack

Yeah. And it's such the, the male fantasy version of this, it's girl girl. And I would like to see them do stuff with each other.

01:16:37:06 - 01:16:38:01

Luna

First.

01:16:38:03 - 01:16:57:22

Jack

I'd like to watch, you know, and then get involved. So that kind of classic scenario. But it's it's really hot to me. And so if, if things could go in that direction, I think that would, that would be really hot. I mean, other things that just sort of turn me on, sort of fantasies, whatever that are kind of on the bucket list, if you will.

01:16:58:00 - 01:17:02:19

Jack

Sex on a mountain. I'd love to do that. You have to be on the top of a mountain.

01:17:02:21 - 01:17:22:12

Luna

But could you would if. But if what I want so bad. Nobody I've ever asked this question to has said yes, I would like if I had a penis and I know this is apparently not how any penis owner I've ever talked to is wired, but if I had a penis, I would want to in a private way that's respectful of other people's autonomy when they're hiking.

01:17:22:12 - 01:17:35:14

Luna

Whatever in a safe way. So I don't fall off the edge of a cliff, like, I just want someone to jerk off over the edge of a cliff and tell me about it. I don't know, like it's the childlike part of me that just wants to, like, drop something off of a very high spot that's not going to hurt anyone.

01:17:35:16 - 01:17:47:20

Luna

Maybe into a river. And I'm just like, how come it must be some sort of reproduction thing? Because every guy I've ever talked to is like, no. And I have, I have no desire. And I'm like, okay, so it.

01:17:47:20 - 01:17:49:09

Jack

Doesn't have to be off a cliff.

01:17:49:11 - 01:17:51:23

Luna

No. No. But just like the idea of a mountain. Yeah.

01:17:52:01 - 01:18:07:06

Jack

Or hiking, like, okay, okay, a little, you know, where like, because I, I'm, I'm hiking just alone with my thoughts and my thoughts are sexual, so. Yeah, I just kind of rev myself up until it, you know, if it's a deserted trail and I can go, I can go off trail a little ways, I maybe. Yeah.

01:18:07:12 - 01:18:19:07

Luna

I think for me there's something that's just like to fly seed fly like it's, you know, not that it's going to like land in a pussy in procreate, but it's like, kind of like a dandelion, but different. Okay. So on a mountaintop.

01:18:19:12 - 01:18:41:06

Jack

So on a mountain or, you know, out in nature, I love hiking and being outdoors. So that kind of goes hand-in-hand with that. I like the, the sexy librarian archetype. The oh, yeah. To have sex in, like, a bookstore or like an antique bookstore or some sort. Not to. So not strangers on a train, but strangers in a bookstore.

01:18:41:08 - 01:18:42:19

Luna

Yeah, absolutely.

01:18:42:19 - 01:18:51:16

Jack

I think for some reason the books, I don't know, help. Totally. What? I like lingerie. Lingerie is really hot to me. Stalking?

01:18:51:16 - 01:18:53:04

Luna

What kinds? Okay.

01:18:53:06 - 01:19:15:04

Jack

Oh, like, like, so thigh high black stockings are sort of the classic. So maybe fishnets or white. I like black or white. Okay. Kind of those classic colors. Lace, lace, plain lace panties, lace bras, that kind of stuff. So, you know, kind of classic, I think, you know, good social conditioning. I've, I've responded. It's like, okay, that sexy.

01:19:15:06 - 01:19:26:00

Jack

Yeah. Yeah, I don't know. Those are kind of some of the, the things that, that I find exciting and like I mentioned, the things that might be out there to explore, I mean, eventually.

01:19:26:02 - 01:19:34:02

Luna

Is there anything else that you would like to be a voyeur for, or any other voyeurism like details that we haven't covered?

01:19:34:04 - 01:19:59:02

Jack

Well, I think so. When you've talked to like other guests and things like, going to play parties or to sex clubs or whatnot, in my earlier days I would have said, oh yes, I'd love to do that. Now I think I understand myself better and realize that I'm probably far too much of a an introvert. And the social aspect is what gives me anxiety.

01:19:59:02 - 01:20:22:08

Jack

And so I'm like, I wouldn't yeah, I'd feel so out of place just for that reason. But if I had a guide, if I had someone who was familiar who, you know, could, could introduce me to that kind of a situation, probably what I would enjoy is the visual that watching it, if there's exhibitionists there, I would pair well with an exhibitionist.

01:20:22:10 - 01:20:34:14

Jack

Someone who wants to show off. I want to watch. Yeah. You know, that kind of an interaction. I that's probably the the only way that would really work. Well, for me, that kind of situation.

01:20:34:14 - 01:20:56:04

Luna

I'm the exact same way. And I will just share a tiny little snippet of a story. Details of this I just shared on Patreon. I recently went to a play party with past guest Mistress Luna, who is a professional dominatrix, and I went as her like she does scenes. She organizes scenes for one of the play parties here in LA and she was like, would you want to do a scene?

01:20:56:04 - 01:21:08:21

Luna

Like. And I was like, yes, I would love to be your toy. Like, how would you like to use me? And so I ended up being a, you know, her baby dragon that was tamed. So it was like, how to team your dragon was the name of our scene. And so we were the the scene that got things started.

01:21:08:21 - 01:21:33:07

Luna

And I have gone to several play parties in the past and realized that I need way more connection and communication. You know, I don't I don't need to like, be deeply headed into relationship to fuck someone, but I need to feel connection, communication, and a certain amount of safety and like a really good reason to fuck them simply because I am hit up so often by like random rude people from the internet who say quite rude things.

01:21:33:07 - 01:21:49:13

Luna

So it's like, for me, stranger play is like not a turn on, but someone who is like, charming and can talk and like will. Also, I need to feel safe that like my very literal brain is okay. So if I don't understand something I'm not going to get made fun of because I didn't get the metaphor because I didn't.

01:21:49:14 - 01:22:09:10

Luna

I mean, there was a metaphor, but like, I'm very, you know, like I need to feel safe in all the ways. And so going to have a job, I also don't really think that I'm, I'm not exactly an exhibitionist. Or maybe this is the definition of exhibitionism. I'm about to have one of my like, up level understandings, like spiral of discovery.

01:22:09:12 - 01:22:27:05

Luna

I don't know if I'm an exhibitionist, but I really enjoy being like, of course, all the guests. You can watch me get tamed and teased and paddled and slapped with my own tail for your pleasure as I'm on stage. And because I'm such a great performer with all this years of experience, I can open up and make sure that you can see my reactions.

01:22:27:10 - 01:22:44:17

Luna

But also I'm totally in the scene and just having fun. You know, that was really gratifying. And then the rest of the party, I just got to kind of like, watch other people and be like in the scene and watch the other scenes that they had performance wise. You know, as a performer, when you're performing, you're performing and it's separate from play for legal reasons.

01:22:44:19 - 01:23:02:22

Luna

And so then I was just like around, like being my little dragon self, like watching people. And I found that very, very pleasurable. Of course, in the mean zone, people aren't like fucking fucking because of, again, I guess, legal reasons. You can only fuck in these certain areas. But, I found that very, very fun. And like, I'm like, oh, so I need a job.

01:23:02:22 - 01:23:22:06

Luna

And I because of exactly what you just said, I spent a lot of time fantasizing about kind of the social constructs that I would build in so that many different types of people feel welcome at these different parties. Because I was also watching, I was like, that person looks as awkward as I would feel if I were down there.

01:23:22:06 - 01:23:43:08

Luna

But like, I found like a high perch and had, like, crawled up on this, like, rope jungle gym and was just, like, laying there, like being a drag, like a Cheshire dragon, like watching everyone. And, it was very interesting. So I can strong, strongly relate. And also, I've been to a party with a partner that got way more awkward than I ever knew him to be as we arrived and I was like, you're supposed to be my dominant.

01:23:43:08 - 01:24:05:04

Luna

No. Okay. Never mind. The abort mission will break up, actually. Okay. Oh, so totally, totally relatable. And I also fantasize about a police base that has, like, around the edge is just the voyeurism tunnel. So, like, for those of us who are, like, hypersensitive, you know, but maybe it has a lot of portholes or like, whatever. So everyone knows and and then the exhibitionist can like, perform for them and.

01:24:05:04 - 01:24:12:23

Luna

Yeah. So, there's a bunch of my fantasies and experiences related to everything you just said.

01:24:13:01 - 01:24:20:18

Jack

Yeah, yeah, I would have trouble navigating there to how do I approach? What if someone approaches me and I'm like, okay with that or not? Okay. Well, like

01:24:20:20 - 01:24:38:00

Luna

Yeah, yeah, yeah, yeah. And then also trusting that I know my own answer in real time in the, in that space and then trusting that I can actually change my mind and communicate it like there are some high level things happening, but also I think with experience and the right sort of, like you said, having a guide in these spaces.

01:24:38:00 - 01:24:47:09

Luna

I do think everything is possible. Okay. Anything else? Bucket list wise, hopes for the future in general for your sex life, etc.?

01:24:47:11 - 01:25:09:15

Jack

No, I think, it's it's going really well. It's, you know, it's is as good or better than it's ever been. Things are, are improving and growing. And so I'm really excited to to continue that. It's it's not at a really fast pace. It's not like we've sort of jumped back into to doing all the things all at once.

01:25:09:15 - 01:25:30:17

Jack

It's still, you know, it's been a a 20 year relationship so far. So we we're in no hurry. We take things at a as a reasonable pace, I think for us. And so I'll, I'll gradually, you know, see where things go. It's, like I mentioned, my, my wife kind of sees me as the one to, to explore and then bring her along.

01:25:30:22 - 01:25:44:18

Jack

Yeah. And so I'll, I'll continue doing that. And to see where, where we end up. But yeah, it's, it's, I'm kind of excited. It's I'm optimistic. It's I love that things are good sexual lives.

01:25:44:20 - 01:25:56:12

Luna

Oh, I love that. I love that it's almost like the modern or one of the many modern forms of hunting. Like I will go out and scout and get the things and bring it back and be like, woman, do you like, should we?

01:25:56:14 - 01:25:58:15

Jack

Shall we?

01:25:58:17 - 01:26:21:20

Luna

Okay, so fantasy time, if you were in charge of at least one of the rooms or maybe the whole space, you know, my big dream about having a future, big play space and whatever. Maybe someday we'll have the afternoon lights. Maybe not. Maybe it'll only with my fantasy and all my masturbation. But if you were designing your own perfect play space or were contributing to one, what elements would you definitely want to include?

01:26:21:22 - 01:26:45:10

Jack

There's a couple a couple different rooms that I would want. The first one is really maybe more than a room. I want a library of like all the sexual knowledge that you can gather, all the books that have been written, all the articles that have been written, all the, you know, whether it's audio or video, you know, have that available, but also transcripts of that.

01:26:45:10 - 01:27:11:10

Jack

It's a real research library, kind of. And it would have to look like a library with like stone walls, arched doorways, stained glass windows, kind of that old school sort of monument to knowledge sort of, sort of thing, where people can come and research things or contribute things or, you know, authors of books could come and give readings and talk about it.

01:27:11:12 - 01:27:33:01

Jack

You know, it would just be really that place for knowledge of sexual knowledge, not not porn or erotica, although it's going to kind of brush up against that stuff. But really just the all the stuff that we've learned and a place to have that available. So. So that's one the more playful space as a room is a it's a wet room, basically.

01:27:33:01 - 01:27:54:13

Jack

You get and well, I don't have a real specific vision for this. It wouldn't be like the easy way would be like a shower or locker room kind of thing, but I wouldn't want it to be like that. I would want it to look like a regular room. Or maybe that's a bedroom or a living room or something, but it's one where everything can get washed down.

01:27:54:13 - 01:28:09:22

Jack

Yes, like you can hosed down everything. There's drains there. They're kind of hidden. There's there's ways to clean the room that are sort of discreet. And anything can get washed off. There's good ventilation to dry everything out once things are washed off.

01:28:10:00 - 01:28:14:12

Luna

Maybe it even doubles as sensation playing like an a car wash. It has big blowers. Was like.

01:28:14:13 - 01:28:14:22

Jack

Oh, yeah.

01:28:14:22 - 01:28:19:00

Luna

So after where you can go in and get a slap beat on your skin.

01:28:19:01 - 01:28:38:19

Jack

There would probably have to be showers adjacent. Sure that you can step into right, right out of this room. Maybe laundry facilities as well, but something where it's just whatever sort of squirting wet play and or whatever, anything. Nobody has to worry about damaging anything or making a mess. But you can do like, whatever turns you on.

01:28:38:21 - 01:28:58:05

Luna

Oh, I always I have wondered, you know, they had those car. I think it's is it an element the like boxy car. I feel like early when it came out it was like advertises. So you can hose everything down like this is for outdoor ventures. And I have always wondered if like people into water sports and messy play have ever done it in those cars and just like host them out.

01:28:58:06 - 01:29:11:10

Luna

So I love, I love the idea of a of a room that is a wet room just designed to look like a regular thing. I think that could be so cool. And what if the showers were just, like, built into sneaky things, you know, like that would be. Yeah.

01:29:11:10 - 01:29:14:20

Jack

If you could hide them, make them discreet so they don't look like what they are until.

01:29:14:20 - 01:29:33:03

Luna

Yeah, like a sconce. But then it actually, you know, that's cool. Oh, I love that I. Okay. And if you had to be some type of sex worker for two years in a alternate reality where, you know, that's how we all do our public service for two years at some point in our adulthood. What kind of sex worker would you be?

01:29:33:05 - 01:29:59:13

Jack

I don't know, it's it's hard to see myself in that role of, like, a provider of sexual services in, in any way that that role is, seems in our culture. So, you know, the women or the escorts, that's what people are seeking out. Although I know there are male male escorts. Yeah. I might be more sort of sex work adjacent where, you know, one of my hobbies is woodworking.

01:29:59:13 - 01:30:02:01

Jack

And I could see me making, like, sex furniture.

01:30:02:03 - 01:30:05:19

Luna

Oh, yeah. Oh, wait. How are you making furniture?

01:30:05:21 - 01:30:39:02

Jack

I have not, I have lots of regular furniture. I need to make sure it's cool for the house. But one of those is I do need to make up a new bed, so that could be what I can incorporate there. Yeah, but to. I think it would be fun to be a maker of things in that way that, you know, you could make beautiful furniture that's also, you know, oh, it has these sneaky little tie downs or, you know, the heights are adjustable or something, you know, so you can sort of transform it and adapt it to, to whatever sexy play you, you want to do.

01:30:39:02 - 01:30:46:15

Jack

So, you know, that's kind of the if I were to be a sex worker, it probably have to be something along along those lines.

01:30:46:17 - 01:30:58:07

Luna

I love it. Beautiful. Okay. And lastly, if you could go back in time and give younger you a piece of sex related advice, what age or ages would you pick and what would you say?

01:30:58:09 - 01:31:21:06

Jack

I have a couple answers, a couple different ages. The first is is maybe a little more wishful. If I could go back to my high school self like when I was 15 or 16, but I don't know exactly what I would say. I don't know what I could say. My goal would be to get me to where I'm dating and having those experiences, relationship experiences.

01:31:21:06 - 01:31:42:09

Jack

Maybe they lead to sexual experiences earlier in my life. Not to not having sex until 21 was bad. It's just I kind of feel like I missed out on some experiences there. I think. Yeah, whatever. So but I don't know what I could say to myself really at that age. It would. It wouldn't be anything simple. It would have to be a series of lectures, probably.

01:31:42:12 - 01:32:01:04

Jack

Yeah. What I needed at that age was like, driver's ed for dating. Yeah. You know, something to to really the what do I do? How do I do it? What am I what, you know, to answer all those questions because dating for me at that age or really at any age it's been I did not enjoy it. I was not good at it.

01:32:01:06 - 01:32:14:12

Jack

In many ways it's like being dropped into a a city in a foreign culture where you don't know the language, you can't read the signs, everyone around you seems to be navigating everything just fine. But but you don't know where you're at or how to get where you want to go.

01:32:14:14 - 01:32:26:08

Luna

And then and then once you get to know the city, you're like, oh, they kind of don't know either. Some of them do. Everyone's on different pages. There's no universal language for getting on the same page. We got to make it up as we go and do our best. Okay. All right.

01:32:26:10 - 01:32:33:11

Jack

So that's that's guy like consider that a more wishful answer because I don't know that my nature really could have changed that radically. Yeah. Yeah.

01:32:33:12 - 01:32:39:13

Luna

For me well it's a it's a total fantasy question because obviously we're all turning out perfectly.

01:32:39:15 - 01:32:59:14

Jack

Yes, exactly. The second answer is a little more practical. If I could go to my mid-twenties self when I kind of had those years of when I was single, lonely and desperate, pretty well described me at that age. And being desperate is some pretty strong chick repellent. Yeah, I think it's like, please, in there. Like, oh no, I totally get it.

01:32:59:14 - 01:33:25:05

Jack

So I think the solution or what I would say to myself, my like, say 25 year old self would be go see an escort. Just get that experience and it would have like, yeah, it would relieve the tension. But more than that, if I know I could do that at any time, yeah, the knowledge would have relieved some tension and relaxed me.

01:33:25:05 - 01:33:41:09

Jack

And then I could approach, you know, just regular interactions with kind of just with that in mind that I'm not desperate trying to make this turn into something or hoping that it turns into something. And that's all I can think about instead of just kind of being more in the moment, getting to know this person.

01:33:41:11 - 01:33:42:15

Luna

Totally.

01:33:42:17 - 01:34:01:11

Jack

And also, I would have learned a lot. Yeah, I would have probably approached that as, hey, teach me like I want to know. Like, yeah, everything that you can, that sort of older woman, younger man fantasy has always been pretty strong with me. Yeah. Although now given my age, that's more of a younger woman. Me. But. Yeah.

01:34:01:13 - 01:34:16:07

Jack

So. Yeah, so that, I think it would have. Yeah, I would have learned, I would have kind of been more relaxed. I probably would have checked things off the bucket list much earlier, but that's, you know, for that alternate history.

01:34:16:13 - 01:34:17:14

Luna

Yeah. Yeah. Yeah.

01:34:17:16 - 01:34:19:19

Jack

Totally. So I could have gone down that route.

01:34:19:21 - 01:34:37:06

Luna

Oh, I love it. And my lady friends who work at the brothel say that they've had some really great, just beautiful, confidence boosting experiences with the virgins that come in to like, learn and show up for themselves. So I love that. Wow, Jack, thank you so much for being a guest on Sex Stories.

01:34:37:08 - 01:34:38:00

Jack

Thank you. Well.