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30s bisexual Latin male, married to a partner of 5 years, works in the tech sector, from NYC, into: crossdressing, pantyhose, playing with toys, camming, and bondage.

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00:00:00:07 - 00:00:22:03

Luna

Our guest today is a bisexual Latin dude in his 30s, married to a partner of five years. He is into cross-dressing pantyhose playing with toys, especially his BBQ dildos, camming and bondage. He works in tech in NYC. Welcome, Jay. Can you start off by telling us if you had to rate yourself on a sexual shame, a meter with ten being the most full of shame and one being not so shaming.

00:00:22:04 - 00:00:23:09

Luna

Where do you fall right now?

00:00:23:11 - 00:00:44:21

Jay

Right now I would be four. I think it changes depending on what I do when I get dressed up right, like how far I go. And we'll get into it on cam or my activity, you know, like and then I'm like, oh shit, I remember I'm married. I shouldn't be doing like the guilt that comes back. Okay. So it then goes back up okay.

00:00:44:22 - 00:00:46:10

Luna

Does it ever go down?

00:00:46:12 - 00:00:56:03

Jay

I think it does. If I'm a little tipsy or a little high or poppers or whatever, the case would be that it goes down to negative steps.

00:00:56:05 - 00:00:57:03

Luna

Okay.

00:00:57:05 - 00:00:58:21

Jay

The thing goes out the window, to be honest with you.

00:00:58:22 - 00:01:19:21

Luna

I get it when I start to get a little bit turned on, I get very stupid. I don't know if I've said that enough on this podcast. I get really stupid when I'm turned on and make dumb decisions, because also the shame on me because of who cares? I'm in love with my body in the world, so. Okay, can you give us a little overview of what your sex life is like right now and your favorite parts?

00:01:19:23 - 00:01:39:20

Jay

The wife and I are intimate a couple of times out of the week. She travels a lot for work, so I'm also able to enjoy my cross-dressing part. And that probably is the predominant way I kind of enjoy myself now. You know, dressing up and kind of whether it's playing with myself, you know, finding pleasure in that way.

00:01:39:22 - 00:01:52:04

Jay

It's nice to be able to do both. Right, to be kind of this what I call a submissive housewife persona. Yeah. And then kind of be like a dominant, macho man with the wife.

00:01:52:08 - 00:01:55:05

Luna

I love that. Are you monogamous?

00:01:55:06 - 00:01:57:14

Jay

We are strictly monogamous.

00:01:57:15 - 00:02:01:07

Luna

Cool. Can you tell us now what is sexy mean to you?

00:02:01:09 - 00:02:27:23

Jay

It means details. I've learned, especially with the dressing up part. You know, for me, that's kind of what drew me to dressing up. It's like the art of, I guess, femininity. Right? And what is feminine? So I find, like, details, right. Perfume, read certain textures, like certain things that for me is sexy, right? Like a well put together, even if it's an older lady or an older man that to me is sexy.

00:02:28:01 - 00:02:31:06

Jay

Again, it falls into details and how they put all that together.

00:02:31:08 - 00:02:48:17

Luna

That's so cool. I feel like you probably have an eye for detail that I would really benefit from. My brain is like spiraling off into a fantasy of like, following you around in the city and being like, what about that person? What about that? What do you see there? What do you see there? That's really cool. When did you start noticing those sexy details?

00:02:48:18 - 00:02:51:12

Luna

This I'm going on of order, but I'm just so curious.

00:02:51:14 - 00:03:10:22

Jay

No, no. And that goes into what got me into pantyhose, which is in the sixth grade. I had a teacher who would wear, like, these business skirt suits, and she would wear pantyhose in high heels, and I would be in the back of the classroom, and I would just be mesmerized by her legs. Right? Like in these hoes.

00:03:11:00 - 00:03:29:22

Jay

And then at some point after lunch, I guess she was walking around in the heels and the heels would come off, so she would walk around barefoot, you know, in the classroom. And I was just like, her legs look amazing. Why do they look like that? What is that? You know? And then I started to notice that detail.

00:03:29:22 - 00:03:43:20

Jay

Pantyhose on my classmates, on women in everyday life. And I was just so curious of, like, why didn't the male teachers kind of look like that? And again, the details. Right. And that's kind of what led me down the path.

00:03:43:22 - 00:03:49:23

Luna

Wow, that's so cool. Okay, tell us now, when do you feel sexiest?

00:03:50:00 - 00:04:11:22

Jay

As soon as I know I'm going to dress up like my brain, transform from a macho Latin dude to the suburban housewife type of thing, and I'll, like, play my music specifically, like jazz. I'll, like, take my time getting ready, painting my nails, drinking my glass of wine while getting ready. And it's all kind of like feeds into the process, right?

00:04:11:22 - 00:04:25:02

Jay

Of, like laying out my clothes, my outfit, my heels, laundry. Like, everything kind of looks like, oh, I'm excited. Start to like, turn me on. Right? Like looking forward to that. And that's when I start feeling like just super sexy.

00:04:25:04 - 00:04:31:05

Luna

Is there a difference in the way that you bathe yourself, like shower or bath in preparation?

00:04:31:07 - 00:04:49:05

Jay

Yeah, yeah, there's music playing when I'm going to dress up as a female. There's never music playing as a guy. It's just like in and out. She's, you know, I don't care, but I take, like a bubble bath, maybe light a candle. It's a complete switch of, like, persona movements, like everything. I love.

00:04:49:05 - 00:04:54:07

Luna

That. Cool. Okay. Now tell us what counts as sex for you.

00:04:54:09 - 00:05:16:17

Jay

To me, honestly, I don't even see it as, like, actual intercourse with another person. Like I said, I consider just me playing with myself. And whether it's my toys or. Yeah, camming, whatever. Like, it doesn't have to be the actual act of being intimate with someone else. I kind of just see it as bringing pleasure to myself in whatever way that looks.

00:05:16:19 - 00:05:18:22

Jay

So that, to me is I consider sex.

00:05:19:00 - 00:05:24:22

Luna

I love that. Is it pleasure? Like, is getting off a part of it, or is it just creating the pleasure for yourself?

00:05:25:02 - 00:05:36:11

Jay

Creating the pleasure? Awesome. Definitely. You try to, like, hold off for as long as possible, you know, so releasing you just kind of like, build up to build up for me. It's all part of it.

00:05:36:13 - 00:05:41:23

Luna

Have you ever referred to yourself as a pleasure artist? Because I feel like you might be one thing.

00:05:42:01 - 00:05:45:06

Jay

That might be a thing. I like that, actually. I might put that on my mind.

00:05:45:07 - 00:05:59:09

Luna

I feel like you should. It just popped into my head. I'm like, this feels like it would describe him. Okay. Now tell us. Growing up, did you ever receive a helpful sex education sex talk from a grown up you trusted, or a lesson in consent?

00:05:59:11 - 00:06:18:03

Jay

No. And that's part of my cultural background. We don't really talk about it. The hope is that you just kind of like, either learned in school. And I never had the birds and the bees talk. It scares the crap out of folks in the Latin community to kind of have those conversations with the kids. That was at least my experience growing up.

00:06:18:07 - 00:06:20:21

Jay

So I learned what I learned from school, from sex.

00:06:20:23 - 00:06:23:09

Luna

From sex ed. So you did have a little bit of sex ed?

00:06:23:11 - 00:06:24:13

Jay

Yes, yes.

00:06:24:15 - 00:06:27:21

Luna

Do you feel comfy saying, like, where you grew up? Did you grow up in New York?

00:06:27:23 - 00:06:37:12

Jay

I grew up in New York. Born and raised, I love it. I feel like it's also part of why I can do what I do. You know, the dressing up so comfortably when I do, do it outside.

00:06:37:14 - 00:06:42:00

Luna

Totally. Can you tell us what you do remember about the sex ed that you got?

00:06:42:02 - 00:07:02:13

Jay

I remember the videos, you know, like, how to put a condom on on the banana. I remember watching, like, they showed us. You know, how women get pregnant and then, like, pregnancy videos of births and stuff like that. At that age, it was a super helpful because I think I wasn't really open to it, at least to what sex meant, really.

00:07:02:18 - 00:07:07:04

Jay

I just remember still kind of figuring out what excited me, you know?

00:07:07:06 - 00:07:26:17

Luna

Totally. Well, and as I reflect back to I remember I was open, curious and eager student like. I remember the first time we got that Aids talk in fourth grade, I was proud, I felt so adult. We got an Aids life like foundation water bottle and I would carry it around. Being like, that's right, I'm a ten year old that knows what sex is.

00:07:26:19 - 00:07:46:17

Luna

And I remember just like waiting for the part where they would fill in the people details and they never did. And, you know, as I look back over my formative years, I'm like, well, fuck, I wish everything included some people details because this is not very helpful. So on the note of people details in your adult life, do you have an example of an explicit clear?

00:07:46:17 - 00:07:54:11

Luna

Yes. Either from you that you gave to a partner or their partner gave to you that resulted in something hot or sexy?

00:07:54:13 - 00:08:24:01

Jay

It was my first time dressing up and meeting a guy. This was after high school. I had just kind of dressed up at home. I decided that wasn't enough. I posted an ad during the Craigslist days and I got tons of emails from folks. But there was this one specific guy who was super straight forward. Honest. Right at the beginning, he's like, here's my pictures, here's my phone number.

00:08:24:02 - 00:08:44:15

Jay

Let's talk until you feel comfortable. If this happens, it happens. If not, that's okay. So for it to be my first time that I wanted to meet up with a guy and have that intro and him be so respectful when he finally said, hey, you know, my girlfriend is out this week and you want to come over? I was like, yes, I felt comfortable doing so.

00:08:44:15 - 00:08:53:21

Jay

And you know, it was the best thing I could have done because it led me to then being with more men while being dressed up and exploring that part of me.

00:08:53:23 - 00:09:17:06

Luna

Fuck yes. I'm so glad to hear you had that experience. And also, I also just agree that low pressure safety vibe is so hot. The like, if it happens, great. If not, that's great too. That is so sexy. Okay, now tell us. I know that you're married. I know you're in a monogamous relationship, but what is safer sex look like for you?

00:09:17:06 - 00:09:22:13

Luna

And before you were in a monogamous relationship, what did those conversations sound like?

00:09:22:15 - 00:09:44:01

Jay

Before my relationship, it was always looking to meet with someone who is super clean, always uses protection. Like, I mean, that was during the wild, Wild West days. You know, Craigslist was a crazy place, so I felt like I had to be straight forward on what I was looking for and hoping that the stranger was also being honest.

00:09:44:03 - 00:10:07:00

Jay

So I think it was very important to kind of put that out there. And once you actually met the person, make sure I had on my part the condoms, like whatever I needed to have to potentially not be tricked into any situations where I didn't want to be in. And with my wife. It's just we explore, we talk about things afterwards, what we liked, what we did it just to kind of for us to feel safe in our intimate relationship.

00:10:07:02 - 00:10:11:06

Jay

So I think it's just overall communication right off the bat. Very important.

00:10:11:08 - 00:10:19:07

Luna

It sounds like you and your wife are a little bit kinky. Do you have conversations explicitly about what you're into or what you're wanting to play with?

00:10:19:09 - 00:10:37:11

Jay

We do. I think the longer we've been married, the more we want to keep things fresh and explore things, and we see something in a movie or a show and we're like, oh yeah, let's try that. Or, you know, I'll buy lingerie for her that if either I may eventually want to wear or I'll have her wear, you know, so it could go either way.

00:10:37:15 - 00:10:40:08

Jay

There's no lose lose, you know. I love that so much.

00:10:40:09 - 00:10:55:21

Luna

Okay, so now let's get into the details of your sex life. Take us back to the very beginning and then walk us through your formative sexual experiences. Start with what do you remember first? When did sex as a concept enter your brain?

00:10:55:23 - 00:11:14:07

Jay

I think it honestly was goes back to the sixth grade and having that feeling of at that time I didn't know what it was, but it was like excitement of seeing pantyhose. Right? And it was like, I didn't know what that was inside of me. That made me feel turned on. And it wasn't until I said, you know what?

00:11:14:08 - 00:11:32:05

Jay

Let me try and see if my mom has pantyhose. Right. Let me just check if I can get my hands on this and see what it feels like. Why am I drawn to it? And I remember, luckily my mom had a drawer full of all kinds of pantyhose. I did two colors. I hit the jackpot. You know, I had never seen her actually wear them.

00:11:32:05 - 00:11:54:07

Jay

But for some reason, I guess from back in the day, she had. Yeah. But I remember trying on my first pair and it was like an instant hardon, like I had never experienced anything like that. I didn't even know what I guess a hard on. You know, like it was just like this blood rush and I was like, Holy crap, this feels awesome.

00:11:54:07 - 00:12:18:12

Jay

And I remember that kind of being my first sexual experience with my body and kind of being like, oh, aware of like, wow, this makes me feel good. And then after that, it was kind of like, oh, I want more of this, right? Let me now see what the clothes feels like. And that added more excitement. And then I became hyper aware of like again my classmates and kind of being turned on by them.

00:12:18:12 - 00:12:45:20

Jay

I became like a little perv and like, try to peek under desk to like, get like upskirt because I started realizing like, oh, that stuff was kind of turning me on, right? And then I remember, okay, this isn't enough. I want attention. And I remember going online. This was like during the AOL chat days. Oh yeah. And I remember going online while dressed up in chat rooms, kind of like seeking attention, right?

00:12:45:20 - 00:13:08:00

Jay

Like, hey, I'm this young cross-dresser dressed up at home. And guys, of course, love that, you know? And I would remember kind of that kind of be like, oh wow, this is a nice feeling as well. But then I was also in high school kind of finding women attractive. Right. And it was like two different experiences. And I didn't know at that time I didn't label myself.

00:13:08:00 - 00:13:26:08

Jay

I didn't know if I was gay. If it was bisexual, I just do. I kind of liked what I liked and I wanted to explore both worlds. Right. And that's kind of what led me to first being intimate with women, finding out that I kind of like being dominant with women. So that was nice to find that out.

00:13:26:08 - 00:13:40:12

Jay

And then for some reason, when dressing up, being completely submissive. So it was a wild, transformative experiences and trying to figure out those things. Right, and taking risk and kind of to figure out what it is exactly that I liked.

00:13:40:13 - 00:13:58:18

Luna

Yeah. Can you help us understand a little bit the landscape of this time in your life? I'm hearing not a lot of judgment from your younger self. Like, it really sounds like you had an openness and a sense of permission. And did you have to hide the fact that you were dressing? Were you like, nabbing your mom's clothes, or did you have a sister thing?

00:13:58:18 - 00:14:01:19

Luna

Like what? What was that part kind of like for you?

00:14:01:21 - 00:14:22:01

Jay

This was the age when I was like, hey there. My parents would be like, let's go out somewhere. And I'm like, no, I'm good. You guys, you guys love. I don't want to go to so-and-so's house anymore. You know? I got some, like, school stuff to do. Homework. So much homework. Yeah, so much homework. And I would just, like, take advantage and just dress up at home while my parents were out.

00:14:22:03 - 00:14:45:13

Jay

So it's always, like, in short, little spurts, you know, during, like, junior high school and high school as well. Then when I got into relationships, I would wait for my girlfriends to kind of be out and I would wear their stuff. And that's how I got kind of like my age as well. And it wasn't until after high school where, you know, I graduated, started working where I could finally buy my own clothes.

00:14:45:15 - 00:15:06:07

Jay

Yeah. And I had a stash, like hidden at work because I had my own office. So I was able to, like, have a lovely set of clothes. I didn't have to steal clothes anymore and kind of develop like my own sense of style and fashion in that sense. And that's still the case with this day. Like, no one really knows from family or friends or like that.

00:15:06:07 - 00:15:14:09

Jay

I dress up so I have stuff that's kind of like hidden away and and I just dress whenever given the opportunity to do so.

00:15:14:11 - 00:15:21:08

Luna

Wow. Okay. So even in the formative years, you did not have a confidant outside of your online communities.

00:15:21:10 - 00:15:22:14

Jay

Correct? 100%.

00:15:22:19 - 00:15:25:12

Luna

Did you say your wife doesn't know?

00:15:25:14 - 00:15:27:19

Jay

She has no clue.

00:15:27:22 - 00:15:29:16

Luna

How is that for you?

00:15:29:18 - 00:15:40:21

Jay

It's kind of like an adventure in a way. And then it's also like, oh crap. Like, I wish she would be down and we could both, like, dress up in sexy lingerie. Yeah. Or, you know, we're having fun.

00:15:40:23 - 00:15:42:18

Luna

Oh, that would be so fun.

00:15:42:20 - 00:15:56:12

Jay

That is my dream. But it's also like, oh, we can go shopping. And she doesn't know that. I'm like, oh, fuck, like, that would look good on me or like, buy whatever, because eventually I'm going to wear it, you know, like it's, it's it's a fun game of like can mouse like wait.

00:15:56:12 - 00:16:05:22

Luna

So when you buy something that maybe eventually will become yours, does it just one day disappear or how does that look?

00:16:06:00 - 00:16:21:19

Jay

She has way too much clothes. Okay, so it usually ends up just disappearing and she won't even notice it. And that's how it was. I made sure to kind of take stuff from my younger relationships before my mom, where I knew they weren't going to notice it because it wasn't like a primary piece that I saw them there.

00:16:21:19 - 00:16:37:15

Luna

Right. Very smart. Okay. Returning to your formative years a little bit when did you start physically touching yourself and pleasuring yourself? Did that come in tandem? And then when did that? I assume at some point that dressing up and playing with yourself overlap.

00:16:37:17 - 00:16:56:00

Jay

100%? The first time I tried to hose having that reaction and then subsequently keeping dressing up and having the same reaction, I was like, oh, what? I didn't even know how to jerk off, but it was like I heard about and I was like, oh, so this is what you do when you have this reaction, right? You got to release it.

00:16:56:02 - 00:17:21:23

Jay

And I remember not knowing how to when, when I was like 1213 at that point. I remember exploring and trying it, and it wasn't until I learned how to properly do it while wearing pantyhose that I was hooked. You know, you become like that preteen. That's like going nuts and like, masturbation every chance they have. So that was my first, like, experience with myself.

00:17:22:01 - 00:17:49:18

Jay

And then it wasn't until I fully started to dress up in women's clothes with the hose and everything, where I was like, oh, I wonder what it feels like to have anal sex. Yeah. And that tied into that experience as well, where I would be home. And I remember just kind of my first anal experiences was me in the shower with like the plunger, because it was like the only thing I can think of like, oh, this looks like a dildo.

00:17:49:20 - 00:17:56:17

Jay

And I remember trying that and I was hooked on that as well, but it was definitely tied to the dressing.

00:17:56:19 - 00:18:02:04

Luna

Cool. That's really, really neat. So do you have a favorite texture of hosiery?

00:18:02:06 - 00:18:11:04

Jay

I don't discriminate, but my go to are like definitely matte shiny. I feel like all of them have their purposes for different occasions, right?

00:18:11:06 - 00:18:21:06

Luna

Yeah. You got fishnet. They're not the same thing as a like sheer nudes. And the matte sheer nudes are different from the shiny ones, which are very different from the like, itchy, glittery ones that come out the holiday time.

00:18:21:10 - 00:18:22:06

Jay

Yeah, yeah.

00:18:22:12 - 00:18:37:07

Luna

So as this part is developing in your teenage years, you're having experiences with ladies. Was there a relationship and or tell us about the parallel experiences, however it was happening for you?

00:18:37:09 - 00:19:06:11

Jay

Yeah, I think I was again, more with women and I realized sometimes I would be like, oh, wouldn't it be nice to be the girl that I was, you know, having sex with and how would that look like? It was very interesting because I was still enjoying it, you know, giving the women pleasure. But then at the same time, I was also thinking and planning ahead of like, oh, what a fantasizing is the perfect word.

00:19:06:13 - 00:19:24:10

Jay

What does this look like? Or what will this look like for me if I get a chance to do this and be in like a dirty hotel room? And I kind of, again, got a lot of pleasure out of it because it made me enjoy the present, but then also fantasize like crazy about what was either to come in the future.

00:19:24:15 - 00:19:46:06

Jay

Yeah, and that's exactly how it ended up happening. So, you know, I knew that I wanted to be I mean, I don't like to say the female, but when we dressed up, I wanted to just lay back and have a guy kind of like, do what I was doing, have his way, you know? Yeah, I would make the noises, the moaning.

00:19:46:06 - 00:20:05:04

Jay

Right. My body had to move differently. The first time I was with the guy that I was with, I remember going into it and I was like, I'm not going to get fucked. I'm just going to dress up for this guy. We're going to make out, that is it. I am not gay. We're not going further than this.

00:20:05:06 - 00:20:27:23

Jay

And I remember being there, right? We're making out. It's super hot. And he's like, hey, you know, super respectable. But he's like, do you want to suck my dick? And I was like, nope, there's no way I'm going near that. That is not my thing. Sorry. We chickened out. And at one point I get so turned on that I, like, just let out.

00:20:27:23 - 00:20:45:02

Jay

I want you to fuck me up. And in my head I was like, oh shit, here I am. I didn't even want to touch his dick. And now I just told him, hey, I want you to fuck me. So that to me told me, like, everything right there, right? Like how far I can go. I'm willing to go under the right circumstances.

00:20:45:02 - 00:20:59:02

Jay

And I remember it happening, and I already knew I wanted more of this with different people. Like I wanted to explore this. So it was a lovely experience. Wow.

00:20:59:04 - 00:21:15:12

Luna

Okay, so tell us when you really started to, like, embrace it. It sounds like you were already using the phrase cross-dresser for yourself, but maybe should we go to the point where you have a job and your own stash of clothes because you can buy them now? Or is there anything we need to know before we get there?

00:21:15:12 - 00:21:17:16

Luna

Like what exploded for you?

00:21:17:18 - 00:21:47:13

Jay

Yeah, I think it was meeting my first guy and he became kind of like a regular nice. And we met up a couple of times and I was enjoying the feeling of dressing up for someone and having them admire me. I guess I started to get my body started, to get more comfortable and kind of like be able to enjoy the fucking and it just be more comfortable in the act itself and getting better at dressing.

00:21:47:13 - 00:22:17:01

Jay

Having my own clothes led me to posting better pictures of myself on Craigslist, getting a lot more attention. And I was young, you know, I was in my early 20s. I wasn't scared of meeting strangers, you know? I remember I had a job that allowed me to kind of get away for most of the day. So I would actually book like a hotel room, like an hourly room, and I would be in the room and I would post, you know, hey, I'm in such and such a hotel for a couple of hours who's down to come and have some fun.

00:22:17:03 - 00:22:21:03

Jay

That's kind of what led me to being with more guys and enjoying that.

00:22:21:05 - 00:22:34:05

Luna

Are there like specific stories that stand out? Also, would love to hear about like favorite outfits throughout the years if you've had them was textures or just specific, like wherever you want to take a take us into the land of specificity and what you have loved.

00:22:34:06 - 00:22:44:21

Jay

Just because of the ease. Like I love like body stockings, you know, like one piece, you get the top and everything, and it has like the ideal little cutouts in certain places, one.

00:22:44:21 - 00:22:46:16

Luna

Size, usually fits most.

00:22:46:18 - 00:23:14:16

Jay

Correct. I would definitely stock up on those and wear those. And and that's what I would post. And I'd be in the hotel rooms and be like, look what you're missing out on, you know? But I remember there were two really like that. I will never forget experiences during these, Craigslist hotel days. The first was I had put on the ad that I specifically was looking for a BBQ, but that I was open to anyone else if I didn't get my BBQ.

00:23:14:18 - 00:23:35:05

Jay

And I remember this older guy, executive guy answered the ad and he was like, you know, nearby, I can stop by in like 15 minutes. I was like, sure sounds awesome. I showed him what I was wearing and he got into the hotel room and right away started to kind of like, you know, check me out. Like, observe.

00:23:35:05 - 00:23:57:08

Jay

Like what? Like he grabbed me, turn me around. Very aggressive. And I had never, ever experienced anyone. Like right off the bat door opens and I'm like, You know, like, hi all like dainty. And he's like, you know, let me see what you're wearing for me type of thing. And I felt like an instant rush. And I remember him, you know, expecting me.

00:23:57:10 - 00:24:17:14

Jay

And he like, mind fuck me. Besides, like, the physical, he's like, you know, I know you wanted a BBQ, but you're going to have to wait. My friends are probably going to come later and I'm going to have much fun with you. And in my head I was like, oh my God, this guy tell other people that I was like, here he was talking in a way that that kind of like scared me.

00:24:17:14 - 00:24:39:14

Jay

But like, I'm so excited. Totally. And then he just wanted oral. I didn't know it at that point, but he just like it was like an oral session for like an hour and a half. He flipped me into different positions and I had never had like, my mouth be so sore. And I remember at the end, at this point, he had put me down on my knees.

00:24:39:16 - 00:25:03:06

Jay

I'm looking up at him and he just like masturbating, comes like on the side of my face and starts to dress up. And the last thing he says, it's like, this was fun. Maybe next time I'll fuck you. And I was like, you know, cum dripping down my cheek. And I was just like, this is so hot. Yeah, that was one of the best.

00:25:03:06 - 00:25:11:08

Jay

And I proceeded to just like, stay there with the come on my face and just like masturbate and cum all over the like the hotel carpet floor.

00:25:11:10 - 00:25:19:02

Luna

Oh my God, I thought that's wow. Was that just like a hot thing? He said, did he ever see you again? Like what happened?

00:25:19:04 - 00:25:20:03

Jay

He never saw me.

00:25:20:03 - 00:25:31:15

Luna

Okay, that's happened to me. The only time I've had two different dudes do that, they fucking ghosted me after. And I was like, oh, I'm. So I'm like, oh, is that the only way you can keep your power? But ignoring me, the.

00:25:31:15 - 00:25:40:05

Jay

Amount of times I had email that because I like trying to like meet up again because it was so, so hot and I was it was amazing. Wow.

00:25:40:07 - 00:25:46:18

Luna

Okay, so tell us, when did you start giving blowjobs? Because there's a you didn't and then you did.

00:25:46:20 - 00:26:09:17

Jay

Wow, that is a great catch. It was actually with the first guy. You know, after a couple of times I saw you I felt comfortable and I started to give them a blowjob. And it was such a weird experience for me at first, because then I felt it was like more submissive than having sex at that point. Like actually, like, you know, if that makes sense.

00:26:09:17 - 00:26:10:05

Jay

Yeah.

00:26:10:07 - 00:26:11:12

Luna

It's very intimate.

00:26:11:13 - 00:26:14:19

Jay

It's something that I'm not going to lie I don't enjoy.

00:26:14:21 - 00:26:26:21

Luna

Are there parts you do enjoy, or is it like, because you're submissive when you're dressed up, like, what can you unpack for us? Like how you categorize it in your brain? I don't want to put words in your mouth.

00:26:27:02 - 00:26:44:13

Jay

Well, I can only think of cock or be with men when dressed up. I think it's also part of maybe not thinking I'm good at it. You know, I remember the few experiences that I have had. Like, I always start like, oh, once you give me an oral, you're supposed to make the person come right away from it, you know?

00:26:44:13 - 00:26:50:07

Jay

And I remember just like it either taking too long or I'm like, what am I doing? Like, you know. Yeah.

00:26:50:07 - 00:26:50:15

Luna

Yeah.

00:26:50:15 - 00:26:52:04

Jay

So I think that's kind of playing the role.

00:26:52:04 - 00:27:10:01

Luna

And I totally get that. I was not confident in my blowjob skills until I had a very dominant partner that was like like this, like this, like this. Yes. You dirty cock core. And then I would get very sloppy. And it was only once I had, like, surrendered to all of that that I was like, oh, and now I really love to like cocks.

00:27:10:01 - 00:27:18:00

Luna

Let myself in the face or just like, like I can play forever. It wasn't until my late 20s that I got to that point and had someone like, really help me build that confidence.

00:27:18:02 - 00:27:42:03

Jay

That is awesome. Because I actually, a day ago I had a chance and I bought a new toy and I was like, I'm going to focus on, you know, giving this toy or like actually just be like a cock slut, like, I jacked the shit out of myself. So club like, it was a new experience for me, but I, I can see if you lose yourself in it.

00:27:42:05 - 00:27:44:20

Jay

How it can be super hard.

00:27:44:20 - 00:27:45:11

Luna

So fun.

00:27:45:14 - 00:27:46:19

Jay

Yeah. Wow.

00:27:46:19 - 00:27:57:05

Luna

Oh. How was the dildo flavor for you? Or like it? Like, is is it gone away at a lot of mine I get really eager with. And then I'm like, oh, it still have the flavor to wash it up on the way.

00:27:57:09 - 00:28:02:23

Jay

I feel like it went away. It went away okay. It was super hot for me. It was just a lovely experience.

00:28:03:05 - 00:28:15:04

Luna

Amazing. Will you tell us some of the physical specifics of what you enjoy receiving when you're dressed up, and if or how those differ from what you enjoy in regular dude mode?

00:28:15:06 - 00:28:35:23

Jay

Just right off the bat. Regular dude mode. We're both men dressed up, I love foreplay, I am like a huge foreplay person. I take my time, I enjoy making out. I enjoy touching running hands all over the body and kind of like, you know, getting a feel and kind of like until you reach that point where it's like, oh, yes.

00:28:35:23 - 00:28:59:20

Jay

Like again, remember the first time was like, oh yeah, fuck me. Like, I want to get that hot. Whether it's while I'm dressed up or in dude form. Yeah, dude form is just I enjoy being dominant, you know, taking charge, but it's pretty straight forward. You know, I, I really am a very visual person. So I enjoy more of, like, when my wife wears lingerie or when my ex-girlfriend will wear lingerie.

00:28:59:20 - 00:29:21:00

Jay

And it's kind of like now when I was dress up in kind of like the same. It's like I enjoy foreplay. I enjoy the guy being aggressive with me for a change. It's funny though, in cross-dressing for me, I enjoy verbal like for a guy to be completely verbal with me and tell me whatever that he wants to tell me.

00:29:21:02 - 00:29:28:22

Luna

Okay, what kinds of stuff are you into hearing? Like, is it degradation stuff? Is it just hot? Is it anything like, do you have limits or favorites?

00:29:29:00 - 00:29:49:02

Jay

I like to take orders when dressed up. That's a big thing for me. I don't really like degradation as much. I like showing off for people when they tell me to show off while dressed up, like sometimes, and that a lot of times they catch me at the right moment. If they say, you know, if your wife only do and like this not, you know, that kind of stuff sometimes.

00:29:49:02 - 00:29:51:22

Jay

Yeah, during the right moment can also turn me on as well.

00:29:52:00 - 00:29:58:11

Luna

Are there different types of outfits that turn you on in different ways, like psychologically for the preparation?

00:29:58:13 - 00:30:25:10

Jay

Yeah, like I can lounge around in broad panties all day, kind of be excited, but it's not until I'm at least wearing some kind of nylons or, you know, this thigh highs, pantyhose, body stockings, something like that. It takes it to another level. And that's when I can kind of, like, be like, okay, I'm ready to play with myself, show off whatever the case may be.

00:30:25:10 - 00:30:48:06

Jay

And I feel like when I'm fully clothed in a dress or a nice outfit, that part is like super sexy. I feel awesome and hot. And that kind of reminds me like, oh, when I get too hot, all of this is going to have to kind of like come off and like, you know, I get to enjoy again the part of the bra, the underwear, the thighs, whatever it is.

00:30:48:06 - 00:31:00:20

Jay

So it's like it's a crazy adventure. I don't wear pants when I'm dressed up as a girl. I always wear skirts. Dresses? Yeah, I hate pants.

00:31:01:01 - 00:31:03:06

Luna

I do wear panties.

00:31:03:07 - 00:31:25:06

Jay

Yes, I actually prefer panties over like thongs, to be honest with you. Just something more demure and kind of like comfortable about it as well. If you wear the right pair, you know, kind of give a very like, oh, you seem very serious and kind of like, you know, you're not slutty, but actually I can't be, you know, totally.

00:31:25:06 - 00:31:41:15

Luna

I feel like wearing panties and skirts and stockings. Like, it really is that sort of like teacher mistress vibe or the like. No, no, I'm just a librarian that loves to be fucked. Very harsh. Okay. When you have to get the panties a little bit and you got to work for it, do you have a slutty mode? Like, have you been in phases?

00:31:41:15 - 00:31:47:11

Luna

You do you have different kind of like not characters specifically, but like, again, different femme modes.

00:31:47:11 - 00:32:12:13

Jay

Maybe when I'm alone. As of late, I've decided to really just like, explore with bigger toys. Right? And when I say that, I mean, like, I'm up to, I think the latest one I got is like nine inches and it's like thick. And I just like, really take my time and like, lose myself in it. Right? Like, I'll have a glass of wine.

00:32:12:13 - 00:32:32:08

Jay

I'll like, you know, get my poppers ready, like I'll play music. Like I just want to like different positions, you know, different places throughout the house. Like just trying to get into the right rhythm with and just taking my time and enjoying that. So that's kind of like one level of like a cock slut or, you know, at home no one's watching type of thing.

00:32:32:10 - 00:32:36:15

Jay

But I think the ultimate for me has been my camming experiences.

00:32:36:16 - 00:32:48:12

Luna

I'm very curious to hear about those before we get into them. When you're just by yourself, is it the sensory experience and the psychological experience? Are you also looking at yourself in a mirror or is it a mixture?

00:32:48:14 - 00:33:01:06

Jay

I love taking pictures, recording myself, looking at myself while doing it, and then like looking at all of that stuff after the fact. Like watching my own film. Fuck yeah to me is awesome. So yes, I love that.

00:33:01:08 - 00:33:08:20

Luna

Okay, tell us about camming. How did you get into it? What do you do? Like everything. I'm curious about.

00:33:08:22 - 00:33:30:04

Jay

So the campaign came about once I got married. You know, I wasn't able to meet guys and I didn't want to write. So I remember just being like, okay, now how do. And Craigslist didn't exist anymore. So I was like, how do I get attention again? And I remember kind of being like, okay, like there's sites where you can camp.

00:33:30:06 - 00:33:54:11

Jay

And I remember my first time was on a site where it was just random with one random stranger. And I remember dressing up, I remember you're wearing at that time like a mardi Gras mask to kind of, like, hide my identity. Totally. And I remember it was like hit or miss, right? Because then you had some people who would fuck with you and be like, hey, show me X, y, z, or do this.

00:33:54:11 - 00:34:18:10

Jay

And then also something like leave the chat. Then you had people who were like really into it, right? Who were like, exactly what I was looking for. Oh wow, you look amazing. Can you do X, Y, and Z for me? So the most part I would just like tease, maybe rip off if I felt comfortable doing it. But I didn't write any toys, I didn't do anything like that was just me dressed up, teasing and things like that.

00:34:18:12 - 00:34:37:00

Jay

And it wasn't until I got better at my makeup and everything and felt really like I became really, like, passable, to the point where some people were like, are you female? Show me your breasts. And I remember like, oh shit, like, now this is like awesome. Like I took it to a whole nother level. Cool. So I like, Ditch the Mask.

00:34:37:01 - 00:35:05:03

Jay

And I remember then going on a different chat site. It was like a bigger audience and kind of like they're specifying, like submissive cross-dresser looking for someone to take control or to have some fun. And I remember I always have to have a couple of drinks in me and it starts off for like a while. I'm just there, tease the, you know, give it a peek of the thighs, dancing, you name it, you know.

00:35:05:03 - 00:35:28:07

Jay

And it isn't until you find like that right person in the group of people who's like, hey, sissy, you know, I know what you're, like, looking for. What are you doing? Oh, shit. You know, like, this is what I was looking for. Yeah. And if I've had enough drinks and I have my poppers with me outcomes, the toy and I will in front of an audience, you know, fuck myself with my toy.

00:35:28:09 - 00:35:52:12

Jay

That's one level. And then the ultimate where I'm like, I have no idea what's going on. Like I'm just gone. I'm like fully in like, submissive sissy mode is when I play with myself, I ride my dildo and then I give myself a facial in front of everyone while dressed up.

00:35:52:14 - 00:35:54:07

Luna

How fun.

00:35:54:09 - 00:35:58:01

Jay

And it's like peak sissy submissive. Wow.

00:35:58:03 - 00:36:10:10

Luna

How much are you worrying about camera angles or moving the camera to make sure you're getting stuff? And then when you give yourself a facial, you have to lay down to do it. Or can you like aim it? And is it like a replay of the hotel room? She got like.

00:36:10:12 - 00:36:26:03

Jay

It's a mix. I got to the point where I actually got lights. Like I have a nice little set up and I just use my laptop in the bedroom where you get a full view of everything. Like, I don't have to actually like like I'm the one who's, like, leaning in to show you my lips or to show you anything, but it can go either way.

00:36:26:03 - 00:37:01:02

Jay

It can go that. I like edge way too much. And as soon as I got laid down to, like, jerk off, it's like I explode before I can even get my legs up in the air and like, I just punch all over myself. But for the most part, I'm actually in full view. You know, I, I lay down and I put my legs up and here you have me either fully dressed up in a nice dress, heels, pantyhose, or if I'm in lingerie, like, you know, legs in the air and nylons and I'm just like, take the best if I'm not too tipsy and just kind of hope for the best, for the most part,

00:37:01:07 - 00:37:09:13

Jay

does end up in my mouth or on the right parts of my face where it's like a full light comes out, which folks apparently love.

00:37:09:15 - 00:37:15:03

Luna

Oh, I bet they love that. Are you into like, come play? Like, do you wipe it on yourself at all or.

00:37:15:05 - 00:37:34:00

Jay

Have it's become a very visual thing where I before would be like right away wipe it off or now I just kind of like sit in it and kind of like have it, you know, like dribble on the black dress and you see, like the white or like the makeup is all messed up. It's become part of the visual experience.

00:37:34:00 - 00:37:48:13

Luna

Amazing. Do you want to talk about makeup a little bit. Like is that part I know that it's part of it, but is there anything to say specifically about how it affects your arousal or like as you've gotten better at makeup, has that shifted your feelings or anything like that?

00:37:48:15 - 00:38:09:19

Jay

There is nothing like, you know, building a whole I collect the art, you know, it's like the art of transforming, of like going from dude mode to people thinking you're full on female. And I take pride in that. I always wear, you know, red lipstick, red nail polish. Keep it very simple, kind of almost natural. Jewelry is a big part of it as well.

00:38:09:19 - 00:38:20:08

Jay

Like, you know, I'll wear like a nice little necklace that I can kind of like, play with while on camera. Like some ring, you know, it's all part of the experience, but I feel like full on makeup takes it to a whole nother level.

00:38:20:11 - 00:38:44:03

Luna

Totally. Totally. I ask too, because for myself, I always saw makeup as sort of a professional necessity since I was trained as a performer or an actor, and I didn't start to really appreciate it until I got into kinky stuff and would put on a face of makeup and then have it get destroyed and that's when I was like, oh, I'm into like messy, like post slutty makeup.

00:38:44:06 - 00:38:50:22

Luna

Like as I think about, like come dripping down your face and like what that might do to your mascara or your lipstick. That's cool.

00:38:51:00 - 00:38:52:18

Jay

It's definitely part of it.

00:38:52:19 - 00:39:06:19

Luna

Are there any specific things that maybe your audience has inspired and you with their suggestions specifically like, it sounds like you have had some really cool interactions, and is there a way for you to tell if it's ever the same person, or is it all ephemeral on cam site?

00:39:06:21 - 00:39:28:15

Jay

For the most part, you have people who follow you, I guess. So I'd use the same people, but it's really nice when there's someone new and they can kind of lead you, maybe to a new direction that you've never been down. For me, I went from just teasing and masturbating, not even showing my face to like, feeling comfortable enough, finding the people kind of, like, cheer you on.

00:39:28:15 - 00:39:46:10

Jay

Like you just ask like, hey, should I do x, y and Z? Should I? Someone's like, spit on your on your cock. And I'm like, what? That sounds disgusting. But you do it and it's like, oh shit, this is kind of like cool, you know? So there is that aspect where people tell you things and maybe after a while you're like, no, no.

00:39:46:10 - 00:40:03:02

Jay

Then you're like, let me just try it and kind of see where it goes. Like, I would always be fully dressed, like in a nice dress and my heels and everything like that. And it wasn't. So people were like, someone really aggressive was like, take off your dress. I want to see you just in your your broad panties.

00:40:03:02 - 00:40:23:14

Jay

And I never felt comfortable, I guess body image wise to do so. And I remember doing it and feeling so, like, exposed and even more like submissive. And then eventually, I'd like, love doing an outfit change for people, you know? So it's, going from a fully dressed, like, sexy lingerie. They love that. And I love that as well.

00:40:23:16 - 00:40:25:01

Jay

Cool.

00:40:25:03 - 00:40:27:11

Luna

What's your relationship to body hair like?

00:40:27:13 - 00:40:44:10

Jay

Usually I'm fully, fully shaved and, like, head to toe, like, not head to toe, I mean, but yeah, I love clean shaven on women and also guys I when I was cleaning with them, I prefer for them to kind of be like cleaner cut.

00:40:45:17 - 00:40:49:05

Luna

Are you talking just pubes or do you also mean like legs and arms.

00:40:49:07 - 00:40:51:15

Jay

Legs and arms and chest. Yeah.

00:40:51:17 - 00:41:09:04

Luna

I just love smoothness and softness. I mean I love all textures, don't get me wrong, I definitely love a burly bear and I will make out with them for sure. But like I also when I can feel someone's skin, especially if someone is like softer than me, I can't stop touching them. I'm like, this is the best real life Dolly.

00:41:09:06 - 00:41:22:06

Jay

Yeah, and it's like, for yourself, for myself, when I'm like getting ready and like, you know, you put lotion on after you just fully shaved. It's like, smell good. You kind of like, are even more softer.

00:41:22:08 - 00:41:27:21

Luna

Are you naturally smooth or like, does your wife notice some days you have hair and some days you don't?

00:41:27:23 - 00:41:34:01

Jay

I'm not naturally smooth okay. Because she doesn't know. So I like tend to like trim the hairs to as low.

00:41:34:03 - 00:41:34:14

Luna

Okay.

00:41:34:14 - 00:41:47:13

Jay

As possible. Yeah. Yeah. If I know she's going away for a while then I'll be like, oh yeah. Like I'm fully going to fully like, do my thing and then shave. By the time she comes back, it'll be grown to the level where she doesn't care.

00:41:47:17 - 00:42:00:01

Luna

Got it. Okay. Yeah, yeah, yeah. Oh, that's so good. I think like other considerations that you have to think of. Not like in the interest of sneakiness, but just because it's so interesting and like, where do you keep your clothes and stuff like that.

00:42:00:03 - 00:42:16:15

Jay

It's in storage. Okay. And some of it is like hidden in the back of a, like a closet in like an old suitcase that no one ever used this type of thing, you know? So there is a lot of just being careful, you know, and again, knowing when to do it, enjoying it, when I'm able to do it.

00:42:16:17 - 00:42:24:20

Jay

Yeah, I remember I was younger having stuff at work hidden in like a drawer and then having to dress up at people's places. So it's always that aspect of having to hide things.

00:42:25:17 - 00:42:36:00

Luna

Absolutely. What do you imagine might happen if she found out and or would it just not be fun to tell her. Like what's the part of you that wants to keep it secret.

00:42:36:02 - 00:43:05:14

Jay

I think the older I've gotten I realized it is kind of like an adventure in a way. So the fact that she doesn't know is kind of exciting in itself. And then it's also like, you know, I think I know like where again Latin in the reaction probably will not be the most welcoming. You know I think everyone not everyone in my family was like oh if you wear a certain color, if you act a certain way you were automatically gay.

00:43:05:14 - 00:43:12:13

Jay

Right. So it's like there's no in-between. Like it's just like, so I don't think it would go over too well to even try it.

00:43:12:13 - 00:43:36:03

Luna

You know, not enough gray area. And what I'm hearing and what I would project from my own experience is like, if something's that awesome to me, I don't want someone I love to possibly yuck feeling at it at all. Does the sex that you're having with yourself when you're dressed up and or kind of the catalog, the history of sex you've had as a dressed up femme?

00:43:36:05 - 00:43:39:18

Luna

Does it inform the straight dude sex that you have?

00:43:39:20 - 00:44:13:20

Jay

Yes, 100% yes, because I've learned things that I enjoy while I'm dressed up, like certain positions or playing a certain amount of pressure into certain places that have kind of transferred over to dude form and have made me feel more comfortable, like be more aggressive or trying a new position that may give my wife more pleasure or myself, especially with anal or, you know, like simple bondage techniques and things like that.

00:44:13:20 - 00:44:17:10

Jay

So it's definitely transfers over. Yes. Okay.

00:44:17:12 - 00:44:23:11

Luna

Would you tell us a little bit about the specifics of what you enjoy together? Like when you say anal, are you the giver or.

00:44:23:13 - 00:44:59:09

Jay

I wish I was the no. Sometimes no. But it's not strictly I'm the giver. Okay. You know, it's not something we do often, but when we do, it's because we're both kind of like in the right mind set, the right mood. And it's just fun to, you know, try it in ways that I've tried it dressed up right where it's like standing up, you know, slammed against a wall or, you know, just like, flat on your stomach on a bed, all fours like, I don't know, it's transferred over where I'm like, yeah, let me try this in dude form, especially with, you know, right.

00:44:59:09 - 00:45:03:10

Jay

To kind of like give myself pleasure, but also give my wife pleasure as well.

00:45:03:15 - 00:45:10:15

Luna

Absolutely. Wow. Do you have a favorite outfit right now? Like a favorite sexy outfit of the moment?

00:45:10:17 - 00:45:32:16

Jay

I have the black mini dress that it's like super short. You can probably see like my ass when I wear it. It's flowy, I don't know, I just feel feels comfortable, but yet it's like a little black dress where it's like just super sexy and simple and any rent. It's just like, she's awesome.

00:45:32:18 - 00:45:45:06

Luna

I get it. Do you have a favorite shade of red? Like the sex stories color of red? That's kind of like the bright red. Orange is my like, that is my favorite color. Like, that's I'm so attracted to that color, I can't help but do a favorite shade of red that, like, really gets you going.

00:45:45:07 - 00:45:54:17

Jay

I think it's just like the regular, like when you think of bloodshot, like red, if that makes any sense. Yeah, yeah, I'm wearing that. Like. Yeah, red in your face. Here I am type of thing.

00:45:54:18 - 00:46:04:12

Luna

Blood red bold. That's so cool. Have you gone shopping for yourself, lady clothes wise. And tried stuff on at the store?

00:46:04:14 - 00:46:30:15

Jay

Yes, I have at that point. I remember my shape meter went down to negative. I was just like, I'm in New York. I feel like people do this all the time. No one gives a shit. I remember I think it was like forever 21 or like one of those or H&M. I love it, and I remember because I was going to go out, I wanted something new and different.

00:46:30:15 - 00:46:45:06

Jay

And I remember like, you have fun with this pizza. Just go and grab stuff and be like, yes, this is mine. I'm going to the dressing room to try this on. Like, you know. So it was a nice experience that I definitely enjoyed. It was exciting as well. Yeah. And no one cares.

00:46:45:07 - 00:47:11:22

Luna

No one cares. It's end okay. Granted, I'm saying this from the perspective of a farm girl who's lived in the big city for a decade and a half in cities. Certainly, I have just found so many people giving permission for weirdos, you know, of course I say that I'm in a body that doesn't scare most people. I have a big smiles that invites a lot of friendliness, but I notice that the weirder I am out loud in public or like sharing stuff with strangers, the more supportive they are.

00:47:11:22 - 00:47:30:09

Luna

So I can only imagine cross-dressing, and I would love to hear from anyone listening. If this is a fetish that you share. If you've gone into lingerie shops, I know I've messaged one of you out there and talked to shop workers and maybe like, let them in on your secret. I don't know why, but I like, love stuff like that.

00:47:30:09 - 00:47:34:09

Luna

Is that something that you would ever do it like a fancy lingerie store again?

00:47:34:09 - 00:47:54:15

Jay

The older I get, the more of those kind of like different experiences that I want. I feel like, oh yeah, I had a place in life where I can, yeah, splurge and I can't be fancy. And I would love that. I think the closest I've gotten to that is and part of my new kink, I guess, is kind of like being an exhibitionist a little bit.

00:47:55:04 - 00:48:13:17

Jay

Like living at night. I'll get dressed up in like a slutty little dress and like high heels and I'll like go out to like an adult sex shop. That's the closest where I've gone where like, here's this person at the counter here I am like, like dressed up, kind of like a slut anyway. Or like, very sexy and naked.

00:48:13:17 - 00:48:24:18

Jay

Care less, right? I'm here. I'm like, here's my lingerie, here's my belt, though, like, I'm here to buy this and they don't even bat. And I, you know, and it's kind of like exciting. And that's the part of this that's gone with that.

00:48:24:20 - 00:48:44:00

Luna

Yeah. Yeah. That's so cool. Okay, I know cross-dressing is not the same thing as drag, but would you ever, like, go to a drag show dressed up or like, is there anything interesting about being kind of in that different kind of community, especially like Performatively like, I know they are very different, but I'm just curious if that is anything for you.

00:48:44:02 - 00:49:08:19

Jay

Yeah. And I have experienced going out dressed up. I've gone to bars and just being aware that I'm dressed up in a different space like that different setting. It's a high in itself. So I definitely would love and have no problem. Like, I would love to go to like a drag dinner show and experience that while I'm like, dressed up as well.

00:49:08:21 - 00:49:13:19

Luna

Is there a part of you that would ever go to like an amateur drag night and perform?

00:49:13:21 - 00:49:14:17

Jay

Yes.

00:49:14:19 - 00:49:18:06

Luna

Would that turn you on, or is that like a separate category for you?

00:49:18:07 - 00:49:29:20

Jay

I think a lot more things turn me on at this point, but like I had to accept it, right? I'm like, oh no, I would just be. But I'm like, that's relatable. I would probably be like, yeah, look at me like.

00:49:29:22 - 00:49:36:22

Luna

Yeah, cool. Tell us about some specifics. Like, do you add boobies? Like, do you pad you pull your skin like.

00:49:37:00 - 00:49:58:15

Jay

I wear like the bra with the padding that it comes with. I'm kind of like, I like to keep it as natural as possible. I'm a slim top individual, so my body is in a way, fit and kind of. I'm not effeminate, but it can pass off as feminine without me having to do any padding, which I'm super grateful for.

00:49:58:17 - 00:50:11:22

Jay

I don't pad the bra, I just, I don't pull anything. I think I don't even know how to tuck, to be honest with you. Okay? The times that I've gone out, it's just trying to pull it back and hope for the best.

00:50:12:00 - 00:50:15:06

Luna

Can you tell us about your experience with tucking and attempting? Does it hurt?

00:50:15:07 - 00:50:39:04

Jay

The first time I ever tried, I could, and I still, I really don't know how to do because it it did hurt. Okay. When I tried the actual technique of like, you know, putting the balls up. And then I remember when I was young, the way I would do it to kind of get like the feminine shape was like, I would just take another pair of underwear and kind of like jerry rig, like almost like a jockstrap type of thing.

00:50:39:06 - 00:50:55:06

Jay

And that was the way that I would tuck. And now it's just like, again, I just pull it back and hope for the best. Yeah, I hope that, you know, because I kind of, I think it hurt so much that I don't even want to try it at this point. I'm comfortable with the way that it is.

00:50:55:11 - 00:51:13:07

Luna

I think I'm adding research, tucking to my bucket list. I don't know what counts for a bucket list, but like researching? Yeah, I'm just so curious to know everything. Is there anything else we don't know about? Whether it's like ways you want to dress and you haven't dressed yet, like stuff you're fantasizing about, or specific stories that we just haven't heard yet.

00:51:13:09 - 00:51:39:23

Jay

There's a list, a bucket list that I'll get into. But I remember another thing of mine now that I enjoy, and I don't know if it's a kink. It's like a walk of shame type of situation where I like. I'll have a few drinks again. This is super late at night, one 2:00 in the morning. I'll go out dressed up, you know, very scandalously, and I will go to my car.

00:51:39:23 - 00:52:02:03

Jay

I'll go out to a sex shop and then on my way back. Right. I'll like park as far as possible from where I live, take my shoes off and, like, hold them in my hand and, like, walk barefoot and kind of like, you know, at that point I'm like, either a little tipsy and it's like, you know, oh, like, I don't know.

00:52:02:03 - 00:52:28:00

Jay

It's like the breeze, the having the movement trying to be like, oh, look at me, whoever seis meses me. Kind of like, I wonder what, you know, kind of I'm like, fantasizing about what they're thinking about me type of dance. And it was a time I did that years ago. It was like 3:00 in the morning. I lived in this building at that point that had a super long hallway, like my apartment was at the far end, I don't know, a few times already no one had ever seen me.

00:52:28:00 - 00:52:46:19

Jay

I mean, you know, no one from the building. Yeah. So that night I felt comfortable. I walked my three blocks with my, you know, my little shoes. And I had, like, a nice little dress and, like, a blazer. I look, like, very business casual. And I get to the building, I'm like, you know what? Today I'm not going to take the stairs because the stairs were closer.

00:52:46:19 - 00:53:09:16

Jay

They were like directly across my apartment. I was like, I'm going to take the elevator. No one will be up. It's 3:00 in the morning. I get off the elevator, I turn the corner, I hear a door open and it is my neighbor, him, his wife and their grandkid. And it's 3:00 in the morning. There's this long hall and there's this.

00:53:09:20 - 00:53:24:10

Jay

And I had to do, like, a real walk of shame, right where I'm like, wow. The wife just kind of like, looks at me kind of like, gives me like a little smile and like a nod, like, oh, shit. Like, this is what you do. I can do it. Was the husband just kind of like you didn't know what to do.

00:53:24:10 - 00:53:36:20

Jay

Like he looked more embarrassed, I guess. Okay, but I was like, what are the odds? It's like 3:00 in the morning. Why are they out with their, like, grandkid? Where are they going? Yeah, we caught me in the act, you know.

00:53:36:22 - 00:53:41:14

Luna

Totally. Is that the first time that anyone from your regular life saw it?

00:53:41:16 - 00:53:51:03

Jay

First time. And. But I remember also like it was huge after I got in the apartment was such a huge like turn on for me. Okay as well.

00:53:51:05 - 00:54:12:17

Luna

So it sounds like your experience with walks of shame mirror my walk of shame understandings in college. The first time that I was like walking home from a boys house early, I guess the next morning, like dressed in last night's clothes. I remember being like, I'm doing a walk of shame. This is my first walk of shame. Wow.

00:54:12:17 - 00:54:15:15

Luna

I do feel pretty proud though. Why is it called The Walk of Shame?

00:54:15:19 - 00:54:23:19

Jay

It's funny that it has that name, but there's something about it. Yeah, no, I don't know what it is. That's become one of my newest things.

00:54:23:21 - 00:54:28:17

Luna

I love that. Tell us what is on your bucket list.

00:54:28:19 - 00:54:52:05

Jay

So I actually have never had the sad BBC that I've been looking for since the Craigslist thing. So I think that's definitely number one. And I think, again, just fantasize, right? And like what you hear and kind of what you see in porn and it's, you know, like hopefully that is the case and find the right person who can kind of just like go all out and kind of like have their way with me.

00:54:52:05 - 00:54:59:06

Jay

In that sense, as of now, it's just been like, me and my toys have been the BBC, you know? So that's been funny, but it's been nice.

00:54:59:06 - 00:55:03:06

Luna

Other details about that that we should maybe know a little bit about, like anything to say.

00:55:03:08 - 00:55:25:12

Jay

I only now get BBC color toys and like again, the bigger the better. And that's just me again fantasizing about hopefully eventually one day me actually getting that in person again. The biggest I've gotten to is like nine inches, and it took me like full three days to be able to like take it all in. But that was also like part of the adventure, you know, kind of like a battle.

00:55:25:18 - 00:55:37:12

Luna

Totally, totally. That's so incredible. Can you come hands free? Is that part of it for you, or is it just getting stimulated everywhere, feeling filled up? Like, what are the parts that are most pleasurable for you?

00:55:37:14 - 00:55:57:21

Jay

I've only been able to hands free maybe a couple of times in my life, and that still eludes me to this day. Yeah, and I think part of it is not having the patience for it. Like again, being so turned on, being in the moment where you start to touch your senses like, oh fuck, like it's too late now.

00:55:57:23 - 00:56:08:17

Luna

I have a really hard time edging myself, but I have reached some incredible heights of pleasure when edged to the hands of someone else. So maybe that's part of that fantasy that'll get rolled into.

00:56:08:19 - 00:56:36:10

Jay

Yeah. So that happened the first time I ever explored Annalynne. I said that was growing up with the plunger, and it was like, as soon as I put it in, it was like, oh crap, what the heck is this? And it was the weirdest thing ever. And the second time was when I got my first toy years ago, and I don't know if it was because I had to set it up the right way and I just like, was like wrote it the right way.

00:56:36:10 - 00:56:43:14

Jay

Like, you know, it was just like, yeah, it was amazing. But I have never been able to kind of get that again. I've come close, but.

00:56:43:16 - 00:56:47:04

Luna

Anything else on your bucket list that's like burning for us to know.

00:56:47:06 - 00:57:02:20

Jay

The other two are like, Because I'm into bondage is like a damsel in distress kind of like either photoshoot or encounter or with someone who's like a good rigger and like, knows what they're doing.

00:57:02:22 - 00:57:17:07

Luna

Oh my gosh, how would that work out for you? Like, would you want to be like, tied up somewhere, getting tortured? And then do you want to get rescued? Or do you want to just fall in love with your captor? Fall in love air quotes, phone sex in love with you? Like, how would that or just anyway.

00:57:17:09 - 00:57:27:14

Jay

Because of being tied up, I wouldn't want to be rescued. I would just kind of like, I guess want to have them have their way. Yeah, with their captive.

00:57:27:16 - 00:57:34:19

Luna

Fuck yeah. What about porn? Do you watch it? What kind of porn do you watch? Like what turns you on? I know you watch your own stuff.

00:57:34:21 - 00:58:00:00

Jay

I watch a lot of predominantly cross-dressing porn, so that's big. And I also like a lot of pantyhose porn, whether it's cross-dressing or female. But I also enjoy, like, mILF porn. I don't know, something to be sexy about an older woman either trying something out new for the first time, or just kind of like being fully comfortable with herself and what she's doing.

00:58:00:02 - 00:58:00:23

Luna

Amazing.

00:58:01:01 - 00:58:08:16

Jay

My last thing on the bucket list would be either a gangbang or two guys, and kind of being like a split roast.

00:58:08:18 - 00:58:19:07

Luna

Oh my god, totally. Is group play ever on your horizon and current partnership know be separate from any dressed up stuff, but it's not something that you and your partner have talked about. It all.

00:58:19:09 - 00:58:25:15

Jay

Now, we've never really talked about it, but we I would say we're not interested. I don't I'm kind of not okay.

00:58:25:17 - 00:58:42:03

Luna

What about shared voyeurism? Like not participating but ever imagine New York must have great sex clubs or venues to go to just to scope people out. And the idea of you like secretly scoping maybe something slightly different could be like, is that turn you on ball?

00:58:42:05 - 00:59:06:12

Jay

Just you mentioned it. It does. It's on the bucket list. And I think the ways that I've experienced that is when I've gone to the adult workshops and they may have like the downstairs that has maybe one little booth or some like something right. Of that sense. And I remember one time going down there and hoping someone was there.

00:59:06:14 - 00:59:30:15

Jay

They were something would have happened. But I guess either good for me or bad for me. There was no one there. Okay, that was that experience. But then there's also a place here in the city that's like an adult when those old school theaters like kind of like dark, you walk, you know, anything goes. I've been close to doing it a couple of times, but I think again, not wanting to cheat on the wife kind of keeps me going.

00:59:30:15 - 00:59:37:10

Jay

But I'm close. Yeah, I'm really close to just being like, one day, fuck it, let me go. And and it is what it is.

00:59:37:10 - 00:59:46:10

Luna

Yeah, I will say it sounds like an incredibly difficult decision to make to be monogamous. You said it was actually an easy decision for you. Do you want to share about that at all?

00:59:46:12 - 01:00:05:00

Jay

Well, again, I think I'm not young anymore. The fear of like meeting with strangers, right, like, has gone higher than when I was younger, right before it was like, oh yeah, I'll talk to you a few times, you send me a picture, let's go. But now it's kind of like, you know, I don't want to like something bad to happen or for my family, my wife, to find out a certain way.

01:00:05:04 - 01:00:18:22

Jay

Totally. You know, I just think it wouldn't be fair. So I think if I go about it again, it would be that it just like I'm in super in that mode and I'm like, yep, I'm gonna go for it tonight. Yeah.

01:00:19:00 - 01:00:22:15

Luna

It sounds like you feel like a different person based on what I do.

01:00:22:18 - 01:00:36:21

Jay

Yeah. And that's I think that's part of it and I'm okay with that. Like just transformation and kind of being like, oh, this is my way to escape. This is my way to live out my fantasies in that sense. And then I go back to my regular life.

01:00:36:23 - 01:00:44:03

Luna

Okay. Are there any other like bucket list things or just a general sex hopes for yourself in the future? I don't know.

01:00:44:03 - 01:00:55:23

Jay

I think I want to just continue to explore, whether it's with myself or other cross-dressers or females who are into cross-dressers.

01:00:56:01 - 01:00:58:17

Luna

Have you ever been to like a cross-dress party?

01:00:58:19 - 01:01:23:09

Jay

I have that time that I went to H&M or wherever the hell I went to buy the outfit. It was because it was the first time I was going out in public. It's like a trans, you know, seedy admirer type of meet up. And I remember it was with someone who had always been inviting me. I would check it out and they have a partner.

01:01:23:09 - 01:01:40:12

Jay

So this person is across our center and their partner is also a cross-dresser. And they were like, you know, please come. You know, you can chill out with us and we can hang out the whole night. And I remember they wanted me to wear a certain dress for them, like a certain color of pantyhose, which already kind of enticed me.

01:01:40:14 - 01:01:49:07

Jay

And I remember meeting them at the hotel. We kind of all got ready at the same time, which is pretty exciting and fun.

01:01:49:07 - 01:01:50:11

Luna

That's so fun.

01:01:51:02 - 01:02:17:02

Jay

You know, having a couple of beers, talking and then kind of like, all right, it seems like it's late enough. Let's make our way to this bar. You know, which is right. It's like it was like a motel and had, like, bar was part of the motel. I remember walking in and it was like all eyes on me type of thing, because, you know, it was like there were a few other girls there, dressers, but most of them were like, guys, you know, was my first one.

01:02:17:02 - 01:02:25:07

Jay

And I'm pretty sure everyone who was there, most of the people were there usually go often. Yeah. And you know, who's your friend? You know, introduce me.

01:02:25:09 - 01:02:27:21

Luna

A brand new belle of the ball.

01:02:27:23 - 01:02:52:14

Jay

Like I'm there. And, you know, guys are offering to buy me drinks. The girl, the cross-dresser that I went with, they're very open. Yeah, in a very, like, open relationship. And she just had her hands on my legs, like, the whole night, you know, she'd give me, like, pecks on the cheek. On the lips. So funny enough, at some point during the night, they have an agreement where the event takes one hotel.

01:02:52:16 - 01:03:18:23

Jay

And besides to, like, open it for the night. And it's like, okay, guys, it's 11:00 room, whatever, whatever is open for whoever wants to go. You know, it's like one room for cool everyone if they want, whoever wants to go. And I remember in my head to me like, oh my, like, I wish I had the guts right to like, go because the person that I was with kind of like just hanging out at the bar and I was like, oh, that's kind of like disgusting.

01:03:18:23 - 01:03:37:00

Jay

And, you know, like, we don't really do that. And in my head I was like, like, why did I come? I if I would have been alone, I would have. And not only that, but then I had the person who was in charge of the event, super beautiful cross-dresser at one point came to me and was like, do you see that guy at the end of the bar?

01:03:37:00 - 01:03:54:03

Jay

And it was like the super chill, handsome guy, like in the movies, you know, just chilling in the corner with his drink, you know, she goes, he wants to potentially play with you. I mean, you know, like a three. And I was like, oh, this is like. I mean, I was like, I'm gonna be an ass, you know, like, I came with this person.

01:03:54:05 - 01:03:56:00

Jay

I didn't know what protocol was like.

01:03:56:00 - 01:03:57:01

Luna

Yeah, totally. Get it.

01:03:57:06 - 01:04:00:13

Jay

Down. Sorry. Maybe next time. So I missed out on.

01:04:00:15 - 01:04:24:16

Luna

But that is such. Okay. I want to highlight that experience as like, congratulations. Because obviously you're so hot and desirable and like how fun. That's also like my dream scenario to be politely and clearly hit upon for a threesome. Like, what a great way to be like, hey, not going to threaten you by approaching you with a double and flanking you going to be really chill about like that.

01:04:24:18 - 01:04:33:13

Jay

Wow. That's hot. That has always stayed with me. I'm like, I wish I could replay that night for so many different reasons. Yeah.

01:04:33:15 - 01:04:39:03

Luna

Have you ever worn, like a flouncy skirt and then gotten a boner that lifted it up?

01:04:39:05 - 01:04:44:08

Jay

Yes. Clap. And that was on those walks of.

01:04:44:10 - 01:04:47:14

Luna

Okay, that was my next question. I was like, and have you walked around in public with it?

01:04:47:16 - 01:05:02:13

Jay

Yeah. But again, it's late at night. Of course, the first few times I did was like, oh shit, everyone's eyes are on me. Totally. I had to hide this. I had to like, run home or do whatever, you know. But then it was just like, I'm like, oh, this is exciting for me. If you see it, you see it.

01:05:02:13 - 01:05:03:20

Jay

If you don't, you don't.

01:05:03:22 - 01:05:08:12

Luna

What about have you ever worn, like, a really long gown or would you be interested in that?

01:05:08:13 - 01:05:15:15

Jay

I have, especially like I like the feeling of kind of like the constriction of it. You know, you can't spread your legs to a certain point.

01:05:15:15 - 01:05:23:05

Luna

You can only take dainty little steps as you walk along. That is very frustrating for me. I'm like, act for firm.

01:05:23:05 - 01:05:30:09

Jay

Here it is. But when you're wearing heels and you hear them, yeah, on the pavement, it's it's a nice experience.

01:05:30:12 - 01:05:40:15

Luna

Like where are some of your other just like favorite things? I feel like there's probably so many details and I just haven't, like, been exposed enough to ask you, all of them. And I'm going to think of them as soon as we hang up.

01:05:40:17 - 01:06:03:05

Jay

Well, I think that night, going back to the meetup, there was a guy also who came up to me and he again, details. Right. He had his hand on like the bottom of my back. And I had like, I had done that in dude mode. Yeah, I have seen people do it, and I was the first time I had someone come up to me kind of like lightly, you know, run there and he's like, talk like, oh, you're new here.

01:06:03:05 - 01:06:22:14

Jay

You know, he got me a drink. He was kind of telling me, yeah, you should come. More like, this is my experience. We should meet up one day. And it was just, like, so much going on that night. But I remember then us three, the group, you know, the two folks that I went with going back to the room, someone was joining us at some point and I was like, oh man.

01:06:22:14 - 01:06:40:01

Jay

Like in my head I was like, this is going to be a foursome. Like, this is going to be awesome. But the person just kind of stopped by to say hi. They kind of like sat there and let me like run my hands to, I don't know why feel comfortable running my hands like through their hose legs and like, you know, kind of like we're all just chatting and having a good time.

01:06:40:03 - 01:06:58:15

Jay

And then they left. And I guess the couple that I met up with, one of them enjoys watching their partner be with someone else, because the main person that I went to meet up with was like, oh, I love, you know, let's, you know, make out and record it. And we made out for I don't even know how long.

01:06:58:15 - 01:07:17:07

Jay

It was like the long as my mouth was sore from like so much kissing. And then, you know, one thing led to another and they ended up starting to give me oral. And then I remember just like being so turned on and I just masturbating it, like, came in my home and called it a night. And it's just like, all right, I'm good guys.

01:07:17:07 - 01:07:29:16

Jay

Like by like, you know, like myself and like, drove back in my, like, outfit and I needed to change back. I was like, this is going to be part of the adventure as well. Like driving back in heels like an over an hour drive.

01:07:29:21 - 01:07:34:16

Luna

You didn't take them off before getting in the I always take my heels off if I'm driving.

01:07:34:18 - 01:07:53:11

Jay

So part of it is I'll start off right. So I'm like, yeah, super confident. And then it's also like, I think for me as part of the fantasy, it's like, oh yeah, like I can't do this. Like let me take them off and drive, you know, barefoot. That night when I was going to the place, I wore sneakers and then I specifically stopped.

01:07:53:11 - 01:08:12:17

Jay

This is the first time I had ever done this as well. I like a rest up. And I specifically made it a point like, I'm going to open my door, you know, take off my sneakers, put on my heels, you know, and whoever sees whoever, you know, whatever. And it was like I for the rest of like the 20 minute drive, I was like, in my full light.

01:08:12:19 - 01:08:15:11

Jay

Yeah, you know, heels and all that stuff. It was awesome.

01:08:15:13 - 01:08:24:16

Luna

It's so cool. I realize I haven't asked you at all about hair, which is classic me. What are the details about hair?

01:08:24:18 - 01:08:45:03

Jay

I love wigs, I don't want to switch it up too much because I feel like I developed a persona. It's always like shoulder length. I'm like super long for a wavy as well. I'm not super like straight and I love bangs for some reason. I don't know whether it's side bangs or regular straight bangs, and I think it's part of the Full-on experience as well, right?

01:08:45:03 - 01:09:00:16

Jay

Whether I'm campy and I can kind of like twirl my hair and play around with it, you can come in it as well, but it's part of like, oh, I got to wash it. But I definitely I go back between like a slight ish blond, okay. To like, darkish brown but more a darkish brown.

01:09:00:19 - 01:09:05:00

Luna

Oh my gosh. Yeah. Does your head get tired? Do you wear a wig band like I'm sorry.

01:09:05:00 - 01:09:25:21

Jay

Keep it as simple as possible. I'll just do like a stocking cap. Nice. And put it on. And usually it's like the right size. So surprisingly enough, I do feel comfortable going into it for them to buy these wigs. So I like go. I'm like, hey, I saw this online, I want that one and I'll like try it on to make sure I don't have to worry about it.

01:09:25:23 - 01:09:44:01

Luna

I now have a ton of wig. They have about 30 of them. I have like 24 active ones because I have all of these characters that are each have different hair. Some of them can look very, very pointy. Is there one that feels sexiest or do you just have like a main rotating one? And then if it gets too much, come in at your retirement?

01:09:44:01 - 01:09:45:21

Luna

Or like what's your arsenal like.

01:09:45:23 - 01:10:01:00

Jay

The I think those are already like retired and those are probably like the cheaper ones. But the ones that I've invested in, I got those kind of go on rotation depending on what I'm doing today or where I kind of be thinking, I'm going to take it. Yeah.

01:10:01:02 - 01:10:05:23

Luna

Are there any like, types of outfits you haven't worn yet that you really want to wear?

01:10:06:01 - 01:10:33:07

Jay

I find myself window shopping a lot. Or online fake shopping I haven't really worn like nice gowns I think because I consider myself I try to give off the experience sometimes I'm like a fancy housewife, suburban housewife. Like I kind of like that look or I'm curious about it as well. Like, you know, glittery or. Yeah, sometimes even now with like everyone you see like with gloves and kind of like a more maybe 50s, 40s kind of look as well.

01:10:33:16 - 01:10:39:16

Luna

Like getting dressed up to go to the theater in New York like people used to do, you know, the opera like, ooh.

01:10:39:18 - 01:10:51:23

Jay

Cigarets and, you know, like, that would be awesome. Surprisingly enough, I've never dressed up for Halloween in a female costume, and I've always wanted to dress up as a girl for Halloween.

01:10:52:02 - 01:10:57:13

Luna

That would be really cool. Ooh, will you please tell me if you ever do?

01:10:57:15 - 01:11:10:19

Jay

I will. I just love, of course, the super short skirt. Yeah, right. Like the nylons and then like the red boots. Like the bodysuit type of tops. It is my dream costume. I would hopefully even find a reason to do it.

01:11:10:21 - 01:11:16:05

Luna

Probably. I feel like your wife could rock a superman, Clark. You know, like you can make it work.

01:11:16:10 - 01:11:20:18

Jay

Kick her into it, or be like, hey, I work. I lost a bit something, I don't know, I'd be like, I got to do this.

01:11:21:00 - 01:11:31:06

Luna

That would be really, really. Or I imagine I'm projecting that that would be a really very hot evening. Like a hot way to just, like, exist in your secret.

01:11:31:08 - 01:11:44:04

Jay

I enjoy so much the times that I've been out in the world. I can only imagine being dressed up that way on Halloween, like, oh, at a party or something like it would be an amazing experience. So cool.

01:11:44:06 - 01:11:54:20

Luna

Okay, is there anything else about your sex life or any stories or any thoughts on sex in general that we need to know for your story to feel complete?

01:11:54:22 - 01:12:26:06

Jay

No, I think and I've seen this from you. It's just like, I wish I would have explored a little more when I was younger, and I say that just because I feel like I know the fear, right? There's fear and I feel like fear made me miss out on a lot, whether it was with myself, with female partners, while dressing up and exploring that side like I wish I would have explored more earlier, that's one of the things I kind of still has stayed with me.

01:12:26:08 - 01:12:45:23

Luna

I think about that too a lot for myself, and I can really relate to it. And obviously I always tell myself, well, it's unfolding in perfect divine timing and that's totally true. Whatever true means. Can you articulate if there was a specificity to any of that fear? Because when I look back on my own, it's a lot of like, I don't know what's going to happen, but I don't really know what to do.

01:12:45:23 - 01:12:58:17

Luna

And so then I just wouldn't. And that's why I have historically learned from people who've held my hand or grabbed me forcefully and inspected me. You know, what was your version of early fear? Like if you can give it a text journal?

01:12:58:19 - 01:13:29:22

Jay

I think it was of not knowing what to do, like me thinking ahead and being like, oh, if I'm put in a certain situation, will I know what to do to give this person pleasure? Yeah. And there was also the fear of I was like, that's a good thing, super respectful. So like, I didn't maybe take as much risk, especially with women as I'm not saying be a douche or a jerk or anything like that, but just kind of like ask for more things or try more things, you know what I mean?

01:13:29:22 - 01:13:31:04

Jay

It was kind of like that fear of.

01:13:31:05 - 01:13:33:16

Luna

Assertiveness and aggression.

01:13:33:18 - 01:13:40:05

Jay

Yeah, yeah. There's always like, oh, this person is going to say no or it's not going to happen, then I'm going to look and feel even worse. Yeah.

01:13:40:06 - 01:13:52:10

Luna

In general, what are your hopes for your sex life going forward? We heard some of your specific bucket list fantasies, but if you had to just kind of like look at the next several decades, what do you hope unfolds?

01:13:52:12 - 01:14:16:23

Jay

I really hope I can continue to explore more of the dressing side sexually, whether it's eventually telling my wife and having her kind of be the one to enjoy that with, whether it's like pegging or her giving me permission to like go off and with someone else or meet with other dressers or just kind of like other guy, like, I don't know, it's been a while.

01:14:17:00 - 01:14:33:12

Jay

I have the I don't think they ever goes away. So I think looking bigger picture, that's kind of ideally where I could be able to live that part out or that side of me in a way that's maybe, you know, more open is the word for that. I feel more comfortable. Yeah. This is a side thing. I'm this different person.

01:14:33:12 - 01:14:37:18

Jay

Let me go and do my thing. You know, I think that's where I kind of want to get to have fun.

01:14:37:19 - 01:14:44:20

Luna

Yeah. And if you could go back in time and give younger you a piece of sex advice, what age or ages would you pick and what would you say?

01:14:44:22 - 01:15:05:05

Jay

I think it would be junior high school. I always had female attention, even at a younger age, even from older women. And I just never, you know, kind of owned up to it or lived up to it. I was super shy kid, so I would kind of kid myself junior like, yeah, go for it. Like, take this attention, do whatever, like explore.

01:15:05:06 - 01:15:06:03

Jay

You know, I don't know.

01:15:06:05 - 01:15:13:02

Luna

Fuck yeah. J, thank you so much for being a guest on Sex Stories. Do you have a sex question for me?

01:15:13:04 - 01:15:23:00

Jay

What are you kind of looking forward to for yourself, like for the next couple of years? Like exploring what you know or that you want to try?