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44 white trans woman, in a relationship of 15-years that is monogamous, with some kinky hall passes.

🔗 LILITH LINKS |  @lilithmkieffer

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

Luna

Our guest today is a 44 year old white trans woman who's been married for eight years in a relationship of 15 years that is monogamous with Nikki Hall passes. She is into dress up, makeup, cleaning, hot wax, being tied up toys, spanking, and receiving anal sex. Letting her curiosity lead her into discovering yummy new experiences. A graphic designer and delivery driver and a father of two from Indiana.

00:00:23:04 - 00:00:24:18

Luna

Welcome, Lilith.

00:00:24:20 - 00:00:25:21

Lilith

Hello. How are you doing?

00:00:25:23 - 00:00:38:11

Luna

I am also been so excited to have you here. Will you please start off by telling our sweet listeners? If you had to rate yourself on a sexual shame meter with ten being super full of shame and one being not very full of shame at all. Where do you fall today?

00:00:38:11 - 00:00:52:11

Lilith

Right now? So right now there's no shame like finally being myself and just living, you know, so that in the past we might change that up a little bit. But, you know, religious upbringings and things like that.

00:00:52:17 - 00:00:59:19

Luna

Can you give us, like the roller coaster of the shame, a meter with approximate like places or situations where you have felt it spike up in the past?

00:00:59:21 - 00:01:28:12

Lilith

Gosh, a lot in high school. You know, that's always a fun time. You know, people are always judging yourself. And religious upbringing was always problematic. You know, sex is bad, sinful only for procreation. I was raised Roman Catholic. So, you know, we didn't really get, like the sex talks or anything else like that. You know, marriage. Afterwards, with my first wife, we had experimented a few things, so that went lower, I guess you'd say, as we tried a little bit of swinging and stuff like that.

00:01:28:14 - 00:01:39:12

Lilith

And, you know, other groups and activities I never really like participated. But it's in the environment. It's always nice. So there's no real like shame. Okay. Around that time. Awesome.

00:01:39:14 - 00:01:43:13

Luna

Okay. Can you just give us a little overview now of what your sex life is like?

00:01:43:13 - 00:02:03:11

Lilith

Currently a lot of it is more self-pleasure. Current life has had some hip surgery issues and she's doing a lot better. She's walking right now, but we're also sort of at that age where we don't need that all the time. And just having like touch and connection with each other, like holding hands, sitting next to each other means a lot more than doing the act.

00:02:03:12 - 00:02:25:06

Lilith

Okay. But a lot of it's mostly self-pleasure with my toys, bad dragons and plugs and tails. Oh, I love, like, just walk around with the tail on. I just like devil long one, you know, just hitting at the floor and kicking everyone. Someone just gives a little nice little jiggle in the back. So yeah, that's always fun. And the fur fox tails and things like that makes a little shivers at the spine.

00:02:25:10 - 00:02:26:00

Lilith

That's awesome.

00:02:26:00 - 00:02:29:09

Luna

What would you say is your favorite part of your sex life right now?

00:02:29:11 - 00:02:49:21

Lilith

Just finding, like, learning myself, like, I always sort of repressed myself. And like, the church always taught, like, you can't do these things, and this is bad. And just knowing when I like figuring out what feels good to me, you know, how I like to be touched and where I like to be touched and what actions I like having on me usually done on me.

00:02:50:01 - 00:02:55:10

Lilith

I'm definitely more of that submissive position, like roll the bottom kind of stuff.

00:02:55:12 - 00:02:58:09

Luna

Tell us what is sexy to you?

00:02:58:11 - 00:03:24:11

Lilith

Confidence. Feeling good in your own skin. Now I walk down the street, you know. Dressed up fully. And I just. I feel good about myself. I was like, give me eyes to everyone. Smile. You know, he's collecting like people. Well, is that a guy or is that a girl? And that always is the fun for me. Like, shocking people is sort of like fun and like, my voice isn't, like, perfect, you know, for my view of what I like.

00:03:24:13 - 00:03:43:15

Lilith

But, you know, I'm, I don't think, like a certain thing. And then I hit on with this and like, oh, this is fun. You know, I guess. Yeah. Little like, you know, shock the world and, like, let people open up and, like, there's more than just one kind of person or two kinds of people in the world. There's a whole range, whole rainbow of people.

00:03:43:15 - 00:03:47:11

Lilith

So that's always neat. I love that. Awesome.

00:03:47:13 - 00:03:54:06

Luna

What would your perfect voice, if you can describe it like what would perfect voice for you feel like or texture like?

00:03:54:07 - 00:04:18:04

Lilith

Probably when I had it back before puberty, like that nice little singing voice. There's like recordings of us singing. When I was younger, my brother and I did Silver Bells intro at a fifth grade Christmas concert. I listen to that again is like it didn't have that lower tone in it like that nice higher, like quiet church boy kind of like tone, you know?

00:04:18:05 - 00:04:21:16

Lilith

But I am what I am. So you enjoy that too.

00:04:21:18 - 00:04:28:17

Luna

Do you mind if I observe you? For listeners who are not watching this on YouTube and just describe you out loud with what I'm saying?

00:04:28:18 - 00:04:29:16

Lilith

Oh no problem.

00:04:29:16 - 00:04:36:11

Luna

Okay. I see long, beautiful hair that looks like it's coming directly out of your scalp. Is that right?

00:04:36:13 - 00:04:41:21

Lilith

No. No way. Okay. I've been growing my hair for, well, I've had it long for, like, over 20 years. Wow.

00:04:41:22 - 00:04:53:01

Luna

Okay. I see a beautiful dress with a belt. I see a bosom. I see dark lips. I can't tell what color the lips are. Are they dark purple or are they black? Are they okay, a purple lip.

00:04:53:01 - 00:04:55:07

Lilith

I love the very colors. Yeah.

00:04:55:09 - 00:05:00:04

Luna

Beautiful. So when do you feel sexiest? Is this part of it?

00:05:00:06 - 00:05:10:19

Lilith

This is part of it. Yeah. I do have to cheat a little bit. Like most of the things are me like the makeup. And, you know, I get lines, extensions and the nails. Hair's on mine.

00:05:11:00 - 00:05:15:02

Luna

Oh. Shorter nails up close please. Okay, so they're kind of. Are they silvery.

00:05:15:02 - 00:05:15:23

Lilith

Blue?

00:05:16:01 - 00:05:18:14

Luna

There's a chrome pointy chrome. Wow.

00:05:18:19 - 00:05:39:04

Lilith

So I chrome the tips and then a purple base. Purple is my favorite color with green and orange. And my, my favorite was a little bit silver too. Okay. The dress I made. So my wife and I are learning on you know, she or you know, sewing. She's teaching me sewing. And I made this for the holiday season for Christmas, the winter stuff.

00:05:39:04 - 00:05:45:01

Lilith

So, you know, the crazy little winter hat to super, super long tail.

00:05:45:02 - 00:05:57:16

Luna

It's amazing. Imagine a Santa hat. But we've got blue and like, is it like snowflakes or stars or something like, okay, it's beautiful. Oh my God, you're literally a snow queen,

00:05:57:18 - 00:06:15:04

Lilith

Beautiful. I always like the winter more. You know, summer's in Indiana. The humidity is unbearable at times. Okay. So you can always put on more clothing in the winter, but you can never take off. Enough with the conservative views, right? You know, other places you might be able to walk around a little more free, but like, you know, you can't do that.

00:06:15:05 - 00:06:31:08

Luna

Yes. Oh my gosh. I forget when I leave Los Angeles and go back to my hometown or anywhere else, I'm like, all right, I'm not wearing enough clothes here, but here I can walk around in tiny tank tops and short shorts and not think about it. Okay, so back to when you feel sexiest. Do you feel sexy or like with more clothes on or like what's.

00:06:31:08 - 00:06:33:06

Luna

Just tell us. Just tell us your version.

00:06:33:07 - 00:06:58:21

Lilith

I like the constraint, so I like the corset feel. I like, you know, like chokers and just being like sort of held and nice, nice pressure on my body and nice flowy dresses. Like movement, like men's clothing is so boring and there's so much more like color and beauty in women's fashion. It's much nicer.

00:06:58:23 - 00:07:10:14

Luna

Can you give us an example of a time in your sex life where there was an explicitly clear yes, that you either gave or received from a partner that led to something that was very hot.

00:07:10:16 - 00:07:46:07

Lilith

So I've been hiding myself from my boss for years, and part of that is I joined a medieval reenactment group. So with that group, we'd, you know, have regular like activities during the day. And I can't speak for all groups, but some of the groups I was in at night, the adults came out and played. Usually with, you know, debauchery, alcohol, nudity, things like that and like these places around us and you know, I made my own alcohol, I do amateur meat making and brought some of that to share with people.

00:07:46:09 - 00:08:05:17

Lilith

I have a beehive in the backyard too. So yeah, amateur beekeeper meat maker. So I brought some of that to share. And that's how I met my wife currently. So I brought the mine and I was passing around and she was very interested in me, you know, my long hair and everything else wearing a nice gown at that time, too.

00:08:05:19 - 00:08:23:22

Lilith

And we went back into her tent and just had a good old time. And that day is like my first time, like doing something. And the funny thing is, my current wife at that time says, baby, you know, the 15 years ago, she sort of like pushed me into it because she was polyamorous, but she still is polyamorous.

00:08:23:22 - 00:08:32:05

Lilith

Okay. We have separated since though. But yeah, that was my like, yes, let's do this and let's go into the tent and have a little fun.

00:08:32:07 - 00:08:40:15

Luna

Okay. So now can you tell us when you tell a friend that you got laid last night, you had sex? What do you usually mean? What counts is sex for you?

00:08:40:17 - 00:09:04:20

Lilith

Usually more like the standard, I guess. Intercourse. You know, my wife hasn't gone really far yet. On, for example, pegging me. Usually it's more traditional. I'm on top and it's fine. You know, I get pleasure from that organ, but it's not like what I really like. And, you know, she's working on it. She's getting there. She's has kicked me out of the house for doing this.

00:09:04:20 - 00:09:25:18

Lilith

Of course, when we first got together, my ex wife, I was worried I lost her because I wasn't manly enough. And so when I get with the current wife, when we first dated, we went to a local strip club slash drag show and I dressed up fully and she's working through, as I said, I put it on hold for 15 years as I raised my kids and got custody of my children.

00:09:25:19 - 00:09:50:14

Lilith

But then I just now, my kids are grown. They are 20 and 21 now, and they are on their own and living in the Midwest. I was always worried about how my creative side would be viewed by the rest of society, so I didn't want to like damage. My children had my children be the victims of ridicule and attacks because their father is, you know, more comfortable like this.

00:09:50:16 - 00:10:16:12

Lilith

Yeah, when they got to college and do their own thing, then I let myself come back down again. But I was always sort of hiding things, like, I have kilts and dresses, blouses I'd always wear, you know, hiding things under regular men's clothing right in the open, you know, having, you know, nice flowery shirt substituting as a Hawaiian shirt and then my hair and my earrings pierced.

00:10:16:12 - 00:10:38:20

Lilith

And now, you see, got my ear be pierced like last two nights ago. I just did my up here's okay. So I want to go for like three total like in the ear. But yeah yeah my kids though, that's awesome because they're totally okay with it. Like they already had sort of the idea, you know, and they weren't surprised when I came out to them.

00:10:38:22 - 00:10:47:04

Lilith

And they have no problem with me. Like this, which is just awesome. I really should have done it like 20 years ago, but.

00:10:47:06 - 00:10:58:03

Luna

It's 2020. I mean, it also sounds like you were making a choice, given the best information you had out of like, love and a desire to maintain a connection with them.

00:10:58:05 - 00:11:09:10

Lilith

The one thing I wanted when I was young was my own children. Yeah. And, you know, if I were to go through hormone replacement therapy and all those other things, that's something that sort of gets taken off the table.

00:11:09:12 - 00:11:12:21

Luna

How did they know? Like, well, it gave them inklings.

00:11:12:23 - 00:11:18:11

Lilith

But they see my laundry okay. And I would not wear like men's underwear. I like thongs.

00:11:18:13 - 00:11:22:08

Luna

Like lacy. What texture? I always like to know people's texture preferences.

00:11:22:10 - 00:11:35:03

Lilith

Victoria's secret has some really nice like cotton like all day ones. And they had like a nice little trim on and they had little fun little things like I have some to have the days of the week on them. But like me the lacy ones are fun, the satin but like the cotton ones, the general wear ones.

00:11:35:03 - 00:11:51:21

Lilith

But they'd see that in the laundry and stuff like that. Like those are these is something anybody else, you know, and my quilts and my work for the reenactment groups, there's always a little inklings. And like, I had more nail polish. I thought I would see that. And like, you know, taking most of it when she went off to college.

00:11:51:23 - 00:11:58:12

Lilith

But now, like the jails and the acrylic, a lot more than the regular, you know, process of just pulls off too fast. Got it. Yeah, yeah, yeah.

00:11:58:14 - 00:12:09:16

Luna

So you said you were raised Roman Catholic and didn't get a sex ed talk from know any kind like, parents, family, friends. So how did you learn?

00:12:09:18 - 00:12:39:02

Lilith

When I was younger, my parents separated my brother and I into different rooms, and I'm the oldest. They put me in the basement, and my dad decided he was going to hide his adult material under the basement stairs. And I guess one day he just left a little too much of it showing. So I'm going up the stairs and I see this weird little bag hanging out from under the stairs, and I grab it at like, you know, 12 ish range, maybe ten inch range around there somewhere.

00:12:39:04 - 00:12:58:23

Lilith

And there's all those adult magazines in there. I mostly thinking like, wow, these women look beautiful. I want to be them. But I was, you know, silly and young and that like, weekend was a concert for choir at my elementary school. And I brought them in to the concert.

00:12:59:00 - 00:13:00:14

Luna

Like in your backpack or just like.

00:13:00:14 - 00:13:17:19

Lilith

Yeah, I brought it out and I was like, I want to show some of my friends these. I got it. And I had the idea that, like, you know, these were probably not what you don't normally show people because you don't walk around and see people like this all the time. There was this one kid I didn't want to show, and he decided he was going to tell the teacher that I had some inappropriate things.

00:13:18:01 - 00:13:36:12

Lilith

So I got the magazines confiscated by the school. So my dad a few months later, like where my magazines go, where are these things? And he confronted my brother and I about it very aggressively, and his talk involved. Well, if you want to see this kind of stuff, you're in your mom and I can show you how to do it.

00:13:36:18 - 00:13:49:17

Lilith

Like do it. What? Oh, wow. Yeah. So we did not take him up on that offer, right? Right. That was the creepy. Yeah, but yeah, that was the talk I sort of got from him, which is a little dark, a little weird.

00:13:49:22 - 00:13:54:03

Luna

Yeah. What effect did that have on your psyche? What kind of messages around sex today?

00:13:54:03 - 00:14:16:07

Lilith

It just sort of makes it sort of like hidden, like to hide it all. Yeah. Like to not let it out. Not let somebody see it, like the same thing around that same age I started. And as I said, I was interested in what it looked like, not like, oh, look, there's sex or there's a penis or a vagina, and I would go to target, like, bike to it, and I would go to the women's section clothing.

00:14:16:09 - 00:14:39:02

Lilith

So I would just be able to go in and just walk around, touch stuff, feel it and feel my skin. I brought a few things home to and then I would bring them home and try them on. Sadly though, my dad found those and his answer for that was to burn them in front of me after he saw them, but just again just repressed like me being me because they made it like that.

00:14:39:02 - 00:14:58:07

Lilith

You like to not let people see you do this kind of stuff. Not that it's okay. My dad still doesn't really approve of me dressing up, but he knows now I do it. I play in the band as well. I play in two bands, actually. I play the French horn. I mean a local community band and a local pride band.

00:14:58:09 - 00:15:17:21

Lilith

And the pride band had a concert and I dressed up for the concert, and it was a community concert. So there are like five other bands there, and my dad shows up to this concert for another band. I did not tell him I was coming and playing in the pride band, but he was there anyway and I was so anxious, so worked up.

00:15:17:21 - 00:15:38:18

Lilith

Because he's there, I'm fully dressed up, make up the whole works, everything, and I'm freaking out. And my ex-wife is there with me because she plays in the band with me too. She's trying to calm me down and get me relaxed because we had to go in a concert. After the concert, my dad came up to me and was talking to me a little bit and wanted a picture of me dressed up with my mom.

00:15:38:18 - 00:15:56:08

Lilith

So my mom remembers she has Alzheimer's now, okay? And my dad was off to be in a picture too. And he says, no, I have no problem remembering that I'm like this. Oh wow. So there's still some trauma with that? Yeah, but it's like, I can't live my parent's life. If they want me to live. I have to live my life.

00:15:56:10 - 00:16:07:18

Lilith

Yes, but I'm happy like this. It's like I've always gone through counseling, depression issues and like, I'm, like, smiling bigger than I ever smile. I do this so it feels right for me.

00:16:07:19 - 00:16:08:21

Luna

Wow.

00:16:08:21 - 00:16:09:19

Lilith

Okay.

00:16:09:20 - 00:16:28:23

Luna

Thanks for sharing all of that. And I'm so glad to hear that you are like living your self. Before we get into more details, tell us what's your history journey feelings, shame meter been like when it comes to safer sex with partners? I know you're married, monogamous now. What has that been like for you historically.

00:16:29:00 - 00:16:54:13

Lilith

I've only been with two partners and I was married to both of them. I'm looking in the community for like, you know, play partners and stuff like that. And given, you know, permission with my wife, I have currently a friend of both my wife's and mine that is my escort into the Bdsm world. So she sort of goes with me to the events to make sure I don't do anything dangerous, you know, and I'd keep that for me.

00:16:54:19 - 00:17:13:04

Lilith

Sort of reins me in a little bit too, because when I'm excited about something, I. So I just jump right in. So I might not see someone as a danger because I'm excited that someone's interested in me at first place, because I have still have a little low confidence issue of my looks sometimes. Like I get people telling me like, you look great, you look fantastic, you look like you pass.

00:17:13:04 - 00:17:32:15

Lilith

But there's still that feel. I look in the mirror and I'm like, how can you not see what I am like? You can see me in the camera now. It's like, why would you think that? Yeah, there's all that thing with the dysphoria that you're never really good enough. You always sort of doubt. It feels like. And I think I've heard that other times, that you always are second guessing yourself.

00:17:32:17 - 00:17:53:00

Lilith

But yeah, she, she's my little escort into the world. And I went to her house and she had a private party. And that's where I got my first painting and thinking, yeah, like the fire cops and those deal like, great. I loved every minute of that. And I didn't quite get to some space there. Okay. But I was on the verge of it permanent like first painting.

00:17:53:00 - 00:17:54:00

Lilith

So that was really nice.

00:17:54:02 - 00:18:11:11

Luna

Oh my gosh. And just for our listeners who aren't familiar with thinking, my experience with singing is it's Ginger that is peeled and it goes up your butt. Well, it can be any sensitive membrane area will feel kind of the it's a way to create pain and I quote unquote chemical burn. You know, it's a burning sensation but.

00:18:11:11 - 00:18:13:21

Lilith

It's a chemical. It can be removed right away.

00:18:13:22 - 00:18:17:11

Luna

Unlike hot sauce which you can't control. So that's cool.

00:18:17:13 - 00:18:36:14

Lilith

Oh, I'm so excited to hear your details. My hot sauce. And can you bring that up? That's funny because I'm a little bit cook and creative types. You know, I like to dabble in the kitchen, but I'm also a nudist. So I got to go to nudist camps and stuff like that. So at home when I'm not, like fully dressed up like this, I'm completely naked running around the house without the kids there.

00:18:36:14 - 00:18:53:22

Lilith

You know, they're gone now. But I go to prep up dinner and I play naked and, you know, Mexicans fun. But I get to do, like, you know, authentic thing. I can't do Instant Pot or pre-made stuff. It's all peppers and homeworks. Peppers have that capsaicin on them. Oh, yeah. And you don't think you don't think about that even when you wash your hands, it's still on there.

00:18:54:00 - 00:19:10:10

Lilith

So what do you like do a scratch on your face or on your private areas? If I have to, it's still there. Or oh my gosh, I did that once and I set it up to the bathroom so fast, the glass of milk, just to like, wash myself, like, oh my God, it doesn't go away like that. So the thinking is great because it's in.

00:19:10:15 - 00:19:28:17

Lilith

Yeah. You get that nice little warming burning sensation when you're done outer. It's gone. Yeah. And it's fantastic. But you still get that nice little like sensation. It's not like a bad burn. No. It's just like a little like. Like you have Bengay on your shoulders, but thank you. No, don't do that. Thank you. You don't come out.

00:19:28:17 - 00:19:30:11

Lilith

You'll be horrible. Yeah, yeah.

00:19:30:13 - 00:19:45:11

Luna

Are you familiar with the doctor? Bronner's soap? No. Okay, so there's this natural soap. That's the kind that, like, if you're in a bathtub and it's going to empty directly into the earth, this is a soap that you can use. So at burning Man they have their own like blue thing. You can wash it. You know, it's it's natural.

00:19:45:11 - 00:20:03:18

Luna

It's they have one that is like peppermint smelling, but it has peppermint in it because when I wash my pussy with it and like, my like the membranes are like, oh, you know, or like the tea tree stuff from Trader Joe's, like that bath. What? Like it makes the tingle there. So I'm learning all about the sensations.

00:20:03:18 - 00:20:05:23

Lilith

It's a fun, fun tingles. I like untangles.

00:20:05:23 - 00:20:07:09

Luna

Yeah, those ones that go way quicker.

00:20:07:10 - 00:20:22:05

Lilith

There's a lube I like. It's intimate Earth love naturally bliss clove infused. So it has a nice, like, warming sensation. Okay to put on the plugs and other things. And it's like, yeah, there's nice little extra sensations, little extra tingles. Amazing.

00:20:22:07 - 00:20:29:16

Luna

Did those magazines that you found help you discover your own body? Like, what was that relationship like?

00:20:29:19 - 00:20:49:18

Lilith

Yeah, I remember the first time I like with stuff I was on an art class. The teacher brought in, like, these lady's health magazines, you know, the cosmopolitan, you know, women's health, all those general kind of ones. And I took a few of them home to, like, you know, clip out for a project we were doing. And for some odd reason, I decided I was just gonna lie in bed and, like, look at the pictures.

00:20:49:18 - 00:21:13:01

Lilith

And I remember noticing, seeing a reaction of my penis being like, oh, this is interesting looking. And I just, like, did a light touch and then like, Little Squirts came out. I was like, oh my gosh, this feels great. So that sort of developed my interest in like self touching. I didn't date anybody in school. People talk about like having sex on the school bus and in my high school, and it's always like that.

00:21:13:01 - 00:21:34:20

Lilith

And like, people always thought I was gay when I was younger, when I got married, the first time someone came to my mom, they said, why? That's funny. I always thought he was gay. He was so nice. Now I'm starting to realize that I do find people of all walks a little more attractive. Like, I've always sort of suppressed that because the stigma of like being gay in the 80s, 90s and so on and so forth.

00:21:35:01 - 00:21:59:02

Lilith

Yeah, but I'm enjoying looking at certain people I enjoy, like the phallus, I like the penis, I like the vagina. I'm not overly big on a super lot of muscles like Arnold Schwarzenegger, like ripped bodybuilder type snow, but like a nice nerdy boy is really sort of exciting to me, too. Yeah, probably because I'm like in the nerd culture, like being a musician and re-enactor and roll player.

00:21:59:02 - 00:22:11:02

Lilith

Dungeon Dragons, role playing games, board gamers, all that stuff. Yeah, it's always how I use board games and role playing game as a way to express myself playing, you know, other characters for the and another role playing games.

00:22:11:04 - 00:22:20:14

Luna

What was your understanding of your sexuality growing up, even if it wasn't active with other people? Like, did you think about yourself in that way? Like what was kind of that timeline like for you?

00:22:20:16 - 00:22:43:13

Lilith

Sadly, I usually thought I was pretty unattractive a lot of times. I still enjoyed like that to myself, and it wasn't until like much later in life that I discovered other things I enjoyed, like the anal toys. I would love to be pegged one day. That would be great and make sure my wife's ready for that. She has sort of allowed it for a right woman to do it, but she doesn't want a guy to pleasure me with working on that.

00:22:43:13 - 00:23:02:14

Lilith

But I like riding my little toys. That's terrible. I love giving blowjobs. I mean Deep Throat pretty well. It's what I do. I don't have to do anything else. I can just do that. Just like sucking dildo. And I'm getting really excited cause it's like I can almost finish that way just by pleasing a toy. And the toy doesn't get excited, you know?

00:23:02:16 - 00:23:19:23

Lilith

But yeah, I can't wait. If I ever get a chance to, like, do it to a guy. And I find that oral. Yes, it's nice having the reaction from the lady, but I have much more fun with the thought of a guy okay doing it too. So. So I guess I'm maybe swinging a little more by or by curious now, which is interesting.

00:23:20:01 - 00:23:27:04

Lilith

Would not have thought of myself when I was younger. And it's not just because I dress up. It's like I feel that way all the time. Not not just when I wear makeup.

00:23:27:06 - 00:23:42:18

Luna

Tell us a little bit about your early understandings of your sexual self and how it's grown. You know, so you went from feeling like not so attractive in your younger years. What was that first relationship, the formative relationship with a partner like for you.

00:23:42:20 - 00:24:08:05

Lilith

So like the first person like really sort of show interest in me was my ex wife, and I was kicked out of my parents house because my dad special. Let me just leave it at that. He kicked me out when I was like 20 or so. Still, I mean, 19, and I was sort of bumming on a friend's couch, and my ex wife was still in school at the time, and she was coming in for doing homework assignment with this friend, and I sort of saw her and I was like, really interested in her.

00:24:08:05 - 00:24:26:06

Lilith

And we went out to eat one time, and I had mentioned to my friend that she gave me like a tingly feeling all over me when I saw her. My friend sort of blab that out at the restaurant and we sort of started dating. It was nice. After that she took interest in me and that was like sort of a plus because growing up I never really got attention.

00:24:26:08 - 00:24:46:19

Lilith

Maybe, maybe it was there. Maybe I just didn't see it. That helped me. That's maybe someone actually like me. And then my current wife. Now, when she saw me in the gown slinging alcohol at the adult time at the reenactment event, you know, that's another time that someone showed me some attention. And then you get your peepers on Instagram and, you know, don't be one of those people.

00:24:46:19 - 00:25:05:08

Lilith

Don't show dictates, don't send that first thing that's bad. But you get people like that on Instagram and effect life that do those kind of things too. And it's nice getting that kind of tension a little bit, but then you realize it's not really the good attention because they're not really looking at you as a person. They're just looking at you as a toy, you know?

00:25:05:10 - 00:25:24:02

Lilith

Yeah, and that's not good. But it's nice getting there and I'm working on not enjoying that attention a little bit, but it's part of that, that same thing where I get attention. So I'm like, I love it, but don't go to the clubs now. The local Bdsm clubs and I'm getting some attention. People are saying, oh, I love the shoes, or you look great.

00:25:24:02 - 00:25:26:06

Lilith

And in real life it means so much more.

00:25:26:08 - 00:25:46:01

Luna

Yeah, it's easier to figure out too. And it's tough because as a human being, all I can do is project my own experience as a human being onto whoever's in front of me. I'm learning. It's increasingly difficult for us to just guess at the differences that might lie between us. You know, all we can do is read patterns and notice the similarities and notice the differences.

00:25:46:03 - 00:26:04:10

Luna

And so it's like someone may have a great intention and may send me a signal that I'm like, are you a creeper? I can't tell, you know, and like we're using using that to mean perhaps a boundary pusher or someone who doesn't have our interest as a person at heart. When did you start to think of yourself as a trans person?

00:26:04:12 - 00:26:07:03

Lilith

The first, first, first time or like recently.

00:26:07:05 - 00:26:12:18

Luna

Can you walk us through kind of like the progression? Because it's probably pretty nuanced, I would imagine. Right. With that answer.

00:26:12:20 - 00:26:33:00

Lilith

I've always sort of like had this thought, like I remember like 12. I was questioning things like, as I, you know, other boys in the school, I'd talk to them about my friends and like, what they want to do with women. I'm like, I want to be that more. I like the way they looked. I've always sort of like gone back and forth for years about what am I?

00:26:33:00 - 00:26:50:10

Lilith

What am I not? I'm still sort of questioning it, I guess you could say, but I've decided like recently, just to start doing it like see if I like it, go out. I walk around the street like this. I go to work, dressed up, go to the grocery store, the whole works and it feels right. I don't feel wrong.

00:26:50:10 - 00:27:03:11

Lilith

It doesn't feel like I'm doing something naughty or bad. It just I'm living my life. But yeah, I thought about it for years. 30 years. Easily. I'm almost 44. My birthday's on the 4th of February.

00:27:03:17 - 00:27:04:06

Luna

Happy early.

00:27:04:06 - 00:27:13:15

Lilith

Birthday. But yeah, it's years of thinking about it. I'm going to counseling now, and I've been to counseling for years, but never really brought up this with the counselors.

00:27:13:17 - 00:27:15:01

Luna

Wow. Really?

00:27:15:03 - 00:27:34:10

Lilith

Because it was always a bad thing, the religious upbringing. Because God made you this way, right? And you're supposed to just be happy with it. And that's the devil's influence of something different. And I don't really believe in that. But that was my mindset, you know, and the religious upbringing is quite strong when you get indoctrinated at a young age.

00:27:34:14 - 00:27:35:01

Lilith

Right.

00:27:35:06 - 00:27:57:07

Luna

So the part that I've never really understood about the like God made me this way. Arguments like, okay, so God built you with a penis in this body and also gave you the mind and heart that has the desire to be feminine. I actually can't follow the logic of this part of you that God made. It's good that part of you that God made is bad.

00:27:57:09 - 00:28:00:20

Luna

And like just randomly gets assigned to the devil. I don't understand it.

00:28:00:22 - 00:28:17:21

Lilith

Yeah, I agree 100% because if God made everything gods omnipotent gods, yeah, I'll be president. God doesn't mean God knows everything. God is make mistakes because you say he's perfect and as you say in your own books. Yes. So then, if you maybe understand why you hate it so much, why do we have to have war and violence and people bashing and hurting people?

00:28:17:21 - 00:28:47:21

Lilith

Because they're not making you live this way. You don't want to force people to, like, necessarily like associate with me, you know? Yeah, but you just let me live my life. I don't need you and be in your mind, and you want to be in my life, but just let me live mine. Yeah. Like my ex-wife, when we were ready to get, you know, started to get married, I really wanted the big, huge, like, Roman Catholic marriage because it's so much fanciness, so much pomp and circumstance, so, like, beautiful, ornate, you know, and beautiful buildings and all this great stuff.

00:28:47:21 - 00:29:03:14

Lilith

And so wanted that. And I would have loved to want to dress like then, but yeah, I didn't tell my ex-wife at the time. But like when we had the counseling, which is I think it's a good program, they do counseling through the church. But like they told her that are you willing to do these sex things because he wants it in the church.

00:29:03:14 - 00:29:23:21

Lilith

I'm like what. So we sort of stopped doing that church and we got married by my ex-wife's mother's lesbian like friend in a. Yeah, local like little chapel. Yeah. At my ex-wife's mother is a lesbian too. So we had, like, you know, whole lesbian community and stuff like that. And she married us. So it was interesting.

00:29:23:23 - 00:29:29:02

Luna

Were you having, like, regular straight sex, or did she know about your, like, feminine flares?

00:29:29:04 - 00:29:42:18

Lilith

I don't know how much they know. The ex mother in law saw me at a concert all dressed up and was just like, shocked. Okay, so it was like, wow. And like, oh my, you look gorgeous, she said. So I don't see her that much.

00:29:42:20 - 00:29:44:18

Luna

But did you dress up with your ex-wife?

00:29:44:20 - 00:30:05:17

Lilith

No, I never really fully dressed up with her. I think I have, like, undergarments and she knew about my interests and I've told her now and she not surprised me still. But same two minutes and she's remarried. There's new kids. And we had a Christmas all together. Like my kids, her kids, her new husband, my wife. I wore this there.

00:30:05:17 - 00:30:21:10

Lilith

So it's like so good. If you not too much of people you can comment on my Instagram in there. We're all there on Instagram. Lilith and Kiefer just like my name, so I won't know your story. You can know my story. We can talk, have a good time, see how we have similar interests. You know, people styling tips.

00:30:21:10 - 00:30:24:06

Lilith

Also, I like those, you know. Yeah.

00:30:24:07 - 00:30:35:08

Luna

What was it like having or. I don't want to put words in your mouth, but did it feel like pretend man sex fucking with your cock? Like, what was that like for you?

00:30:35:10 - 00:30:53:04

Lilith

It does a lot. It still feels pleasurable. Yeah. You know, it still be glands and all that stuff that works. And it's more of a means to an end. Sometimes it does feel good. I probably would never like, do the hormones or the, you know, the surgeries and stuff like that. So right now this is the magic of modern age having having this.

00:30:53:04 - 00:30:57:03

Lilith

Yeah. You know, there's some interesting stories you can find. I guess they're pricey.

00:30:57:05 - 00:31:01:09

Luna

We're referring to bosoms. For anyone not watching. We've gestured to bosoms.

00:31:01:11 - 00:31:19:08

Lilith

There's like chest plates. I remember when I got with my wife. I told you, we went out to a, strip club slash, like, drag show, and I dressed up, and I had at the time is internet. And it's still new, like birdseed or, like, rice or something. And penny hoes like table bags. So you could put those in a bra.

00:31:19:08 - 00:31:40:09

Lilith

So you give that illusion. Yeah. And then this performer was on stage and had, like, fantastic breasts. I'm like, how is that possible? Because I understood the idea behind tucking. But like there was like full out cleavage and the whole works. And I was just simply amazed and like, I found out later, they're just full plates. They're freaking awesome.

00:31:40:11 - 00:31:52:07

Lilith

Oh, heavy. You know, I mean, it's silicone and stuff like that, but they get the look. And then the magic of, you know, corsets and other stuff like that and hip pants and so take some lessons from the drag performers. Yeah. That's so cool.

00:31:52:09 - 00:31:58:03

Luna

Do you have community, like do you have trans community? It sounds like you have kinky community. It sounds like you have great like queer community.

00:31:58:03 - 00:32:18:16

Lilith

But I'm developing like the trans community. I have another member of the pride band. I'm in is transitioning in the community is actually some people I've met that are trans as well. Lovely lady I'm talking to and one that's a male to female. One is female to male. Okay, so there's a few people I'm talking to on this Instagram.

00:32:18:16 - 00:32:42:10

Lilith

It's been great for that because there's a lot of people on there that you can just talk to people. When I first started, I used a lot of, let's face app, I guess is the program to like, alter the face, but I've gotten away from it. So it's all like makeup now and stuff like that. So awful that people use that kind of stuff like face app and, you know, body switching, like switching things and like that to put on pictures.

00:32:42:10 - 00:33:00:16

Luna

So how will you tell us just some of the physical specifics of the things that you enjoy? And I'd like to get into some of the kinky stuff that you mentioned at the top. So like we heard about caning a little bit. We heard about fishing, but like, tell us just what your body loves and or what you're wanting to explore more of.

00:33:00:18 - 00:33:17:00

Lilith

I like tight stuff, like being constrained, like constricted. I haven't tried a lot yet, but I do that still. Like we have a candle like from, like Yankee Candles and I get nice little heat from amount of time it's been melting. I always love putting my hands and fingers and those. I've been doing that since I was a little kid.

00:33:17:01 - 00:33:51:00

Lilith

Okay? The idea of, like, dripping wax out of me would be like, fantastic. Yeah, I want to try shibori, but I have to do that in a nice either public place or with the right person over time, because that could put me in a dangerous situation if I were to be completely streamed and that people do anything. Yeah, but that's exciting because like, here is a friend we had here at the house, a little while when I first got my wife that she did the certification on the chest, and she would always get tied up and I was like, really intrigued from that, and something I really liked.

00:33:51:00 - 00:34:10:19

Lilith

And at that time, I wasn't, like, ready to come out and say, I like that. And I wanted that. But the support would be awesome. I always have, like the youngest I can remember, like the French maid fantasy, you know, me dressing up and like pretending, you know, cleaning the house, doing a bad job. And then the owner comes home and, like, disappoints me, spanks me and like, you know, what's my skirt up?

00:34:10:19 - 00:34:27:18

Lilith

And, you know, does a few of the things. So maybe, you know, it's always been like a fantasy of mine. My wife was talking yesterday. We watched a local theater put on PLU on stage. Fun. And there's a vignette in there, and she's wearing a French maid outfit. And my wife was like, you want one of those, don't you?

00:34:27:20 - 00:34:45:05

Lilith

Yes, I do, and then she said, would you clean the house with it on? It's like you probably do that. So, you know, she likes me cleaning. She likes me doing stuff around the house and like, yeah, that. I'd have to make the outfit, though. So. Yeah. Because, you know, I want nice and full lace and all the filthiness and all the fun.

00:34:45:05 - 00:34:52:08

Lilith

So that little revealing too, but like definitely short. So I can bend over and like, you know, just show everything you said.

00:34:52:10 - 00:35:08:23

Luna

They totally. You said that like, you can get off giving a toy oral. I'm curious if you would be turned on the video of giving a lady in a strap on. If this is something your wife would ever like, get to the point where it'd be interesting. Like, is that a fun idea for you?

00:35:09:05 - 00:35:14:16

Lilith

Yeah, I have the idea of I would love to be like spit roasted. That would be like an enjoyable thing.

00:35:14:18 - 00:35:17:10

Luna

What's your perfect spit roast? Tell us details.

00:35:17:12 - 00:35:28:10

Lilith

Well, I'd like to first like, you know, start on both the guys like one in my hands and just give a nice little like because I love, like, fingernails and like, like tingling up the side, like, you know, lightly touching, you know.

00:35:28:14 - 00:35:30:11

Luna

Do you mean tingling up the sides of a cock?

00:35:30:12 - 00:35:46:05

Lilith

Yeah. Like stroking at the sides and like, just touching with the fingernails. Light. Stuff like blowing is always fun. Yeah. You seen the guy's reaction on his face? Is nice to like. That's one of the best parts. Is like to think that he's enjoying what you're doing. Yeah. Yeah, definitely. Like do a little bit of rim on the outside the head.

00:35:46:11 - 00:36:01:01

Lilith

I wouldn't care if like circumcised or not circumcised, but either one would be fine. Yeah. And then I'd definitely go for the deep throat and like holding in my voice like, so the idea of being like thinks fuck to be nice to. Oh yeah. So definitely leaned over the back of the bed like head back the whole works.

00:36:01:03 - 00:36:17:02

Lilith

Then the other guy for getting him ready and doing that, both of them. Then they just like switch places and swap back and forth. Then maybe it's pick me up, spin me around. Hopefully they're nice and strong. I'm not like super big, but, you know, until five eight. So I have a little bit of height on me in the heels, like I'm a little taller.

00:36:17:08 - 00:36:18:18

Luna

What kind of heels do you like?

00:36:18:20 - 00:36:23:10

Lilith

Oh, boots are always great. Okay. Like I'm wearing some right now. This kind of style.

00:36:23:12 - 00:36:30:11

Luna

We're looking at a little white booty. Kind of like medium height, little stiletto ish heel and pointy toes.

00:36:30:12 - 00:36:39:02

Lilith

Classy. Wedges are awesome. And I got these from a person that didn't want to wear them anymore. I just wear these on Saturday. Oh.

00:36:39:04 - 00:36:47:23

Luna

Okay. We're looking at some great red and black lace up the front. That's another kind of like medium pointy heel, a little bit thicker, but not much. Okay.

00:36:48:01 - 00:37:04:04

Lilith

Other people like, say they can't do heels like that for very long or they can't do em at all. Yeah, yeah, yeah, I can go like eight hours easily. Wow. In them. Okay. There's probably a little bit of that fun pain feeling at the same time, the euphoria of like wearing this kind of stuff once the once those are laced up though.

00:37:04:04 - 00:37:10:17

Lilith

They're on. And I was at the club 6:00 to midnight and had no issues. Amazing.

00:37:10:19 - 00:37:25:09

Luna

I had some stripper friends who were telling me, like stripper heels or, and I have some strappy heels that I find pretty wearable, depending on which ones. And I personally have never worn drag shoes, but they were like, drag heels are less comfortable, but it's like they're more stable. But I'm like, I don't, I don't know.

00:37:25:09 - 00:37:48:15

Lilith

So I haven't tried those yet. I just get the ones from like Amazon because you can't find it anywhere else. And I got a nice size 12, some high end of women's shoes. Yep. But still findable like other people have like issues. The sixteens is like, I'm sorry, I just can't find me through the special stores. There's these beautiful ones I saw from a lady at New Year's Eve, Pat Mitchell, or some like that, like sparkly and purple, and they're awesome.

00:37:48:15 - 00:37:52:10

Lilith

I want to get those too. So yeah, I have a thing for shoes, shoes and clothing. You're awesome.

00:37:52:12 - 00:38:02:18

Luna

Amazing. I wish I had a little bit more of that gene, but I mean, I guess it's a learnable, but I really I really actually just want someone else to dress me. That's what I would want.

00:38:02:20 - 00:38:09:11

Lilith

Yeah. I love the idea of like, someone doing the corset and like, you know, holding on the bedpost and like, pulling it and stuff like that would be.

00:38:09:12 - 00:38:16:18

Luna

Oh, yes. Have your ladies in waiting, preparing you for the people who are going to be using you and maybe spit roasting you. Oh.

00:38:16:20 - 00:38:20:01

Lilith

Me. Fantastic. I would love that. All good fantasy.

00:38:20:03 - 00:38:29:19

Luna

What about. Okay, so you never got to wear a poofy wedding dress? Is that something you would ever want to recreate hypothetically? Or like, what's the fanciest poofy dress that you have worn?

00:38:29:20 - 00:38:45:12

Lilith

Like, I don't have, that poofy yet. I'm going to work on making some. There was a dress in goodwill and I was like, ooh, I could buy that and just try that on and have some fun for a while. But like, I talk to my daughter and she's like, dad, you don't need that, okay? So you don't need that.

00:38:45:12 - 00:38:58:02

Lilith

It's like, okay, here's what we have. You know, it's like, if I bought a wedding dress and my wife and I were, like, planning on doing our vows again. Yeah. What would she imply by that? It's like, well, you weren't looking for something else. It's like, no, no, no, and I'll pick something else. And we do our vows again.

00:38:58:02 - 00:39:02:13

Lilith

She'd probably want me to, you know, where, where's and all that stuff, so. Oh, it's okay.

00:39:02:13 - 00:39:18:07

Luna

Okay. But maybe there could be, like, two versions. One for her, one for you. I don't know, without revealing any information that would make her uncomfortable. Do you feel comfortable discussing with us? Kind of. Some of the conversations that it sounds like you're having around your evolution.

00:39:18:09 - 00:39:34:22

Lilith

We tend to talk about a lot, and usually a lot of it's like, she okay with me going out or doing this? I'm having a birthday coming up, and I want to go to a drag show on my birthday. I want to get a bunch of friends together, some from the community, some from clubs, some from the band, wherever.

00:39:34:22 - 00:39:51:17

Lilith

I have friends like everybody. I tell everybody about this, my old friends from school now, but I don't get as many people together to go to a drag show, and I think it'd be fun. Yeah, but I mostly just talk about, like, if she's okay with me doing this, is she accepting? Like, we go to the grocery store or is she okay with me dressing, like, at the grocery store with her?

00:39:51:19 - 00:40:08:03

Lilith

She does have a hard limit of like, where I said, where I can go if I want to still be married and I do still want to be married. I still want to be with her. Yeah. And maybe it might change if I'm lucky one day, but I need to take her along for the ride. Not just like the last crazy and.

00:40:08:03 - 00:40:08:17

Lilith

Yeah.

00:40:08:18 - 00:40:22:17

Luna

Yeah, we don't need to shock our partners that we love and care about and want to be with me. Can you clarify for us, it sounds like you're allowed to kinky play in certain ways that don't involve penetrative sex or maybe genital touching. Like, what are the boundaries there for you that are comfy?

00:40:22:19 - 00:40:25:17

Lilith

My boundaries. I don't seem to have any standards yet. I have a sense of.

00:40:25:21 - 00:40:27:17

Luna

Well, that just means you have to find them. Yeah.

00:40:27:19 - 00:40:44:00

Lilith

Yeah, I just haven't found it yet. But I think she's okay with me getting pegged by somebody, a woman, but not for a guy to have anal sex with me. She might be worried that I'll turn gay and want to leave her. Possibly. I don't know, I'm making assumptions, like, you know, I'm trying to figure it out myself to fit her.

00:40:44:00 - 00:41:06:04

Lilith

So she is worried that I sometimes leave her behind. And I've been making an effort to like when I go dressed up. I also give her time on the side, like as her husband. So like sort of like a dual gender kind of situation. Right? And present is both. At times I feel a lot happier like this, but I also love her as well.

00:41:06:04 - 00:41:07:23

Lilith

So yeah.

00:41:08:01 - 00:41:11:20

Luna

So you said you have not yet received pegging, correct?

00:41:11:22 - 00:41:13:10

Lilith

Yeah. Correct. On yet.

00:41:13:12 - 00:41:19:11

Luna

What's your fantasy about your like perfect future pegging scenario that we can just call in?

00:41:19:13 - 00:41:55:04

Lilith

It was like the ultimate thing I wouldn't want to do at the house necessarily, but I'd like to do it at some kind of like seedy, like, you know, underground, kind of like Dungeon Club. It's a little dark and twisted, and it's not like I really want this to happen because, you know, safety issues for like, the fantasy of, like, I'm walking on the street and some van pulls up, grabs me, pulls me in, kidnaps me, takes me to this like dark little dungeon area, ties me up, you know, maybe spills some candles accidentally on me while I'm all tied up, and then bam, Dom light goes at it on me at the same time.

00:41:55:04 - 00:42:18:09

Lilith

Well, afterwards. And like, punishes me and like for being bad and sinful and walking down the street all slutty. A lot of being taken and like, sighs for the toy. I sort of like a big I like the medium sized bed dragons and, you know, left there for a while, just sort of like sitting there. You take all the hearts and just sort of leave it there, sitting in me, not divorcing, just like walking away.

00:42:18:09 - 00:42:21:02

Lilith

Just, like, still leave me tied up with it. Yeah.

00:42:21:04 - 00:42:35:00

Luna

Okay. They're very few fantasies that I come across these days, but, like, have it entered my brain? And that is a good one. That's a really good one. Is that something that would be yummy to you, like in a consensually negotiated like kidnaping scene sort of way? Okay, cool. What was keening like?

00:42:35:02 - 00:43:05:06

Lilith

It was surprising. I was like, worried about me liking it because I'm not normally a person. I thought that would like pain. I never can invite before. Never punched somebody, never done any of those aggressively male things. And I bruise pretty easy. And my foot life has my pictures of my caning experience on there. So he didn't didn't get the video recorded, but the after effects were on there and it was so nice afterwards, like 2 or 3 days just sitting down like you remember the experience the whole time we went to it.

00:43:05:06 - 00:43:23:03

Lilith

It was a private house party with the chaperon that goes with me to the DSM clubs. The friend of my wife's and mine was her house. She's a member of an organization and they had like a class at that time. So I signed up, you know, like signed up. But I was hesitant to do it the first time.

00:43:23:03 - 00:43:36:17

Lilith

But my wife is like, you need to experience these things. You need to do it. You need to see if you like it. So she's supportive with things. She's like, you know, trying to encourage me to like, do it. Maybe she's not doing it herself with me, but she's still letting me do it. Like, you know, the whole past thing.

00:43:36:22 - 00:43:49:19

Lilith

It took me a little while. I had to watch somebody else have it done, and then someone else and I had to just sort of get my mind's like, yes, I'm going to try this. I'm going to try this. It sounds exhausting. I'm going to see if I like it first, you know, like, yeah, to try things maybe twice.

00:43:49:19 - 00:44:09:03

Lilith

Sometimes you don't know if you like something until you try it twice. Sometimes if the first one could be bad, but it can be great and the second it might be bad. You're not gonna give it a shot, right? So I have this tendency when I'm trying to do something, I just pause. It takes a nice cooling breaths in, get the oxygen flowing in the body again and just sort of go for it.

00:44:09:03 - 00:44:25:07

Lilith

I do the same thing with scuba diving. I can't go below the water. You go out of your mind, you can't go up on the water scuba diving, you'll die. I sit there and like, just focus. You think taking a good breath. And just like the scuba diving and the caning, I just took some deep breaths and then got to breathe the whole time.

00:44:25:07 - 00:44:35:16

Lilith

Bent over the little bench they had. And he just went at it. And it's like small little flicks of the wrist. Two he doesn't like you don't do the whole big old arc thing. Yeah, I tend to beat me to death.

00:44:35:16 - 00:44:36:10

Luna

Starting you out.

00:44:36:13 - 00:44:53:00

Lilith

Starting out. And I'm looking forward to the next time. And I guess I was treated lightly because it's my first time. But the people in the area were saying, like, I was definitely nearing that subspace date. So I was moaning a lot and things like that. So it was good and I didn't get off the bench. I stayed there the whole time, so it was fantastic.

00:44:53:02 - 00:45:00:11

Luna

How does that sensation for you compared to spanking? Like, what do you like about spanking? Like have you had experience with spank?

00:45:00:12 - 00:45:23:00

Lilith

I have had a little like spanked myself. No one has spank me yet. Yeah, yeah, I still want it. I don't myself, like when I'm usually playing with myself and my toys, I'll like spank and grab my ass and stuff like that and pull my cheeks apart. And yeah, those kind of things. There is this awesome, like paddle I saw at the BSM club.

00:45:23:02 - 00:45:34:17

Lilith

It was like a shoe. So they had like attached it to the wooden paddle. So you have like the tread of this like really big work boot and that would look very exciting.

00:45:34:20 - 00:45:37:10

Luna

That probably leaves a cool mark.

00:45:37:10 - 00:45:55:15

Lilith

I'm hoping like in the future, maybe I can talk to that person and like moves and accept that. But I'm still new in like the key community. So I haven't like really established what I'm looking for there yet. I'm still talking to some people. I don't want to jump right too far into it. As much as I would love to jump right into it because it looks great, most of my speaking is about me doing it.

00:45:55:15 - 00:46:03:10

Lilith

And like I have a few rods and stuff like that, and when I'm bent over it myself, little tap tap tap tap tap. So amazing. Okay, in.

00:46:03:10 - 00:46:11:15

Luna

Terms of anal sex, what have you explored with your own ass? Like tell us about your solo play. Tell us about what you're like loving the most.

00:46:11:17 - 00:46:24:05

Lilith

I like a bunch of different, like I work myself up to different sizes. Okay, I started out with a lot smaller and now I'm working on like, there's this toy I got from Amazon, which is surprising. You can buy lots from Amazon. I had no idea.

00:46:24:08 - 00:46:26:10

Luna

Yes, but it has funny names, right?

00:46:26:10 - 00:46:40:18

Lilith

Like he names it to find them, to get to find it through eyes searches on like browsers. Yes, but I have like a fisting toy. The hand is sort of shaped like the fingers all put together. I haven't gotten all the way down on the forearm. I have it over there to bring it out. And no.

00:46:40:20 - 00:46:42:20

Luna

I always like to see.

00:46:42:22 - 00:46:47:04

Lilith

Okay, so I like started out with like this one. Okay.

00:46:47:06 - 00:46:51:00

Luna

We're looking at a pink cock kind of medium.

00:46:51:02 - 00:47:00:11

Lilith

Then I moved into like a little bigger hook. This one, it vibrates I have I didn't charge it. Oh there's a hat. So. Oh wiggly.

00:47:00:11 - 00:47:01:10

Luna

Vibration.

00:47:01:12 - 00:47:02:12

Lilith

That one's very interesting.

00:47:02:12 - 00:47:03:07

Luna

Oh wow.

00:47:03:08 - 00:47:17:20

Lilith

Okay, cool. And this is usually what I Deep Throat. Oh, it's just too soft. Cool. So I usually get about right there. My hand. That's pretty incredible. And this is the one I'm working on now.

00:47:17:23 - 00:47:20:09

Luna

Oh my gosh okay. This is a fifth. This is a.

00:47:20:09 - 00:47:29:10

Lilith

50 shaped hand that's like that's like man sized hand. Then this is fun for like all the different like sensations and nubs okay.

00:47:29:10 - 00:47:33:05

Luna

So it's like wiggly ridges. Oh wow. Is this one of the bad dragons?

00:47:33:10 - 00:47:35:08

Lilith

Yeah. It's like a mocha or the bad dragon.

00:47:35:08 - 00:47:37:13

Luna

Yeah. Okay. You've had that up your butt.

00:47:37:15 - 00:47:39:00

Lilith

Yeah. That's so cool.

00:47:39:00 - 00:47:40:15

Luna

What are the ridges feel like?

00:47:40:17 - 00:47:47:21

Lilith

They have sensations. Like there's so many nerve endings there. Yeah, I go, I guess you can say balls deep. Do it. There's no balls on that one. But. Yeah.

00:47:47:23 - 00:47:50:21

Luna

Have you come from, like, prostate pleasure?

00:47:50:21 - 00:48:06:00

Lilith

Like it takes a lot longer. Usually a good hour, hour and a half ish. And sometimes I don't have all that time. Yeah, yeah, yeah. There's some fun toys and then, you know, there's the, the anal vibrator, toys play with one of them. So it's a remote control through the phone to just awesome.

00:48:06:00 - 00:48:07:02

Luna

Neato.

00:48:07:04 - 00:48:21:11

Lilith

So I can like, set directions and stuff. It feels just like like think opened up. I haven't like, gaped yet or anything like that. And I love taking, like, pictures of myself doing it in videos, watching it later. Yeah, I have a lot of pictures myself dressed up, and I have a lot of pictures of myself dressed up pleasuring myself too.

00:48:21:11 - 00:48:25:15

Luna

So have you ever shared those with people or is that something you would consider sharing?

00:48:25:17 - 00:48:31:22

Lilith

I've considered sharing it and I'm worried that those get on the internet. Then they're on the internet forever.

00:48:32:01 - 00:48:36:19

Luna

You can take your face off and probably make a lot of money if you did it. Only fans.

00:48:36:21 - 00:48:50:05

Lilith

Yeah, well, like talk to my wife about that. She said I could do an OnlyFans, but she doesn't want my face in it. I have it, I can't set up. I just, you know, it's a lot of work to make content sometimes too, and it's like it takes it away from just like the fun of doing it. Got it.

00:48:50:05 - 00:48:53:22

Lilith

But I do like looking at it later. I wouldn't mind doing something, but I need to get paid.

00:48:53:22 - 00:49:07:12

Luna

I need to make the money. Yes. Oh my God, I bet you could make a ton of money just based on the people that I talk to and, you know, and then, of course, it opens up the whole can of worms of like, fetishization. Have you felt like fetishized as a trans woman?

00:49:07:14 - 00:49:20:20

Lilith

Not in public, I don't think sometimes online. Yeah. On Instagram set life seems to be some people more respectful, but they still get people just like like one guy coming today. Your hot bitch is like, really? You're going to start a conversation by saying that, right?

00:49:20:22 - 00:49:21:21

Luna

It's like, no.

00:49:21:23 - 00:49:35:07

Lilith

Yeah. So there is a I guess a little bit of it. And I put on my profile what I am, you know, in Instagram. It's funny because like I say on there, marry gender fluid husband. Yeah. And like it ends with me like you're married. It's like, do you read my profile?

00:49:35:07 - 00:49:36:14

Luna

They don't read. People don't read.

00:49:36:17 - 00:49:39:23

Lilith

It's like they see a picture. It's like, oh, I like the picture. Yeah.

00:49:40:01 - 00:49:44:20

Luna

What else brings your body pleasure that we haven't talked about yet? Like, what are they? Sensations.

00:49:44:22 - 00:50:05:14

Lilith

Touch is always good. Like, I love holding hands, kissing all those general kind of things. You know, this is why I have long hair. Besides just to, you know, past. I guess you'd say. But, like, pulling hair. That's always fun. Like, you know, ponytails kind of thing. And just. But that's a fantasy to, like someone just grabbing my hair and just going at it would be very fun.

00:50:05:16 - 00:50:23:11

Lilith

I've always like my hair pulled. My ex-wife would do that a little bit, and she did a little more with like, the toys when I was with her. Yeah, we had a few, like, anal beads and stuff like that. I'd be having, you know, sex with her. And when I climax, she'd rip the anal beads down. We did that a few times and that was enjoyable.

00:50:23:11 - 00:50:40:00

Lilith

I've never, like, dressed up fully and had sex. I would one time with my current wife, I wore panties and then she, when we're, you know, having sex, she, grabbed the panties and sort of, like, pulled on. I was worried about my panties, so I didn't want to do that again because, like, I don't want to ruin my panties.

00:50:40:02 - 00:50:40:20

Lilith

They're nice.

00:50:40:22 - 00:50:45:12

Luna

Totally. Do you have a favorite pair of undies or panties right now?

00:50:45:14 - 00:51:06:01

Lilith

I can't think of an exact favorite one. There's like a few I like wearing a lot. Like, the lazier ones are always nice with you. I'm thinking about trying to make my own like so my own. Oh, cool. So like, there's some clubs, so weird clubs. That's how I got the pattern for this dress. There's the pattern for making your own bras, and that would be awesome.

00:51:06:01 - 00:51:19:17

Lilith

And I want to find a way to make a matching bra like panty set, because I could get some a crazy material. Like, there's this one material from, Sleeping Beauty. I have a project I'm going to work on. I was like, in, like, a bag with it and the matching dress to go with it. There's a hat, too.

00:51:19:19 - 00:51:37:18

Lilith

That'll be fun to make, like matching and go to, like, a convention. Like I'm in Midwest in Indiana. Yeah, yeah. So Jen comes here okay. So I'm going to make stuff for GenCon and dress up and like that'll be awesome. Having like those kind of things for GenCon. So I do a little bit of cosplaying as well. I did it's poison Ivy.

00:51:37:19 - 00:51:39:11

Lilith

Oh, I did that at GenCon.

00:51:39:11 - 00:51:52:12

Luna

I bet you're a great poison ivy. Okay. What other? We've heard a little bit about fantasies of the future, but like, what other things? If we haven't heard? Are you, like, excited to explore in divine timing? Assuming your wife is comfy with it?

00:51:52:14 - 00:52:17:16

Lilith

Yeah, I'm definitely more interested in more play at the clubs and the Bdsm stuff I would like to have like a threesome. I think it'll be awesome having like my wife and me and then another guy. Yeah, I wouldn't mind having like a threesome with two other guys too, without my wife. But you know that given permission, I love her a lot, so I don't want to destroy that relationship and then consent and all those kind of things.

00:52:17:16 - 00:52:34:16

Lilith

So one time my wife and I were naughty. We were at one of our reenactment events, and it was still not quite night yet. And we were close to the cabin and we like, went to the bush line and the tree line and just like, put on a blanket and had sex there. So that was really nice. But we were sort of quiet too.

00:52:34:16 - 00:52:54:02

Lilith

I'm a little bit of a homeowner. I like to make noise. Fuck yeah. And that was fun and kinky to like, just do it. And like maybe walking in the park or nature trails and lifting up the skirt and it's going at it there would be awesome. And like, you know, packing some coins or stuff like that. And yeah, that would be a fun experience.

00:52:54:02 - 00:53:09:15

Lilith

So I have a lot of kinky thoughts of opportunities and thinking like, ooh, just like, let's go in the bathroom, which the idea of a plane would be fun. But like if you're been on a plane, those bathrooms you can't see anybody in there. No, no no no, I would love to go to, like, Europe. Go to a castle.

00:53:09:17 - 00:53:20:02

Lilith

Yes. And have sex in a castle. Oh, yes. Awesome. Like, you know, like like. No, it makes it drafty and cold. You have to keep each other warm and, you know, get really close. Is there an actual dungeon?

00:53:20:02 - 00:53:24:13

Luna

I feel like there's got to be an actual dungeon that functions as a Bdsm dungeon. There's got to be something like that.

00:53:24:19 - 00:53:44:08

Lilith

There's got to be something in Europe. I know, probably in Germany. Yeah, they like that stuff in Germany. Yes, yes, leather play would be fun to do to like dressing up. I love, like tight bodysuits like I love now you said the constriction. So I don't know how I'd take being like a dominatrix, like doing it myself, but it'd be interesting having a dominatrix do Stephanie.

00:53:44:08 - 00:53:49:19

Lilith

But I like the humiliation stuff. Not too much, but like, maybe some whipping and other stuff like that would be good.

00:53:49:19 - 00:53:56:00

Luna

Yes, it sounds like you also might like a vac bed if you were ever given the opportunity. Or like latex if you want to.

00:53:56:02 - 00:53:58:04

Lilith

Suck up people. Yeah, yeah. It's like squeezing.

00:53:58:09 - 00:54:00:16

Luna

Yeah, I want to try that. It sounds like a big hug.

00:54:00:18 - 00:54:04:03

Lilith

Yeah. That's what like the fire cupping was just was like an awesome massage.

00:54:04:05 - 00:54:07:18

Luna

Oh cool. Yeah. What was it like? Was it. How could you feel the hotness?

00:54:07:18 - 00:54:16:23

Lilith

I know you feel it's warmth. It just feels like nice and relaxing and muscly. But it wasn't like a sexual thing. It's just like a really deep massage. Wow.

00:54:17:00 - 00:54:22:07

Luna

Okay, so now can you tell us, more broadly speaking, what are your hopes for your sex life going forward?

00:54:22:09 - 00:54:29:23

Lilith

I'm really hoping I can just get a chance to be myself, live myself a little more, and experience more of the things I've held myself back from.

00:54:30:02 - 00:54:37:19

Luna

Oh, and if you could give younger you a piece of sex advice, what age or ages would you pick and what would you say?

00:54:37:21 - 00:55:02:16

Lilith

Well, it's like two ages, I guess. Like don't hide yourself. You know, when you're in high school and don't be like a little wallflower, you know, get out there, talk to people. I was so scared to be myself. Yeah, yeah, I was, but people are consenting. Just be it. And probably after I had my kids in my 20s, just, like, come out, tell people, don't be scared of who you are, what do you like?

00:55:02:16 - 00:55:07:03

Lilith

And you'll be happier that way. And I am happier.

00:55:07:05 - 00:55:12:20

Luna

Lilith, thank you so much for being a guest on Sex toys. And if you want to go follow Lilith's Instagram, the link is in the description.