Strictly Anonymous Confessions - 713 - FETISH FRIDAY: Lilly is a Trans Woman who Cheats on her Wife with Guys

Episode Date: November 3, 2023

Lilly is a trans woman who cheats on her wife with guys and she called in to talk all about it. When did she first realize she was trans? When did she tell her wife she was trans? And, why is she hooking up with guys on the dl? Tune in to hear all the details including her first wife and how much she knew about her crossdressing, how her kids knew about her crossdressing and how they felt about it, how her parents made her feels when they found her female clothing stash when she was younger, how and why she knew she was a female from very early on, how and why she questioned her gender and her sexuality since she was younger, when she started hooking up with men and why it took so long for her to take the plunge, how she feels about having sex with women and why she’s never really enjoyed it, how she allowed her first wife to hook up with other guys and how she felt about it, how and why she decided to be honest from the get go about her being trans with her second wife and how she felt about it, how and why she won’t ever fully transition, how she got a free pass from her wife and how it led to her first hook up with a guy, how she likes to dress up and where she shops for clothes, how she feels about pronouns, the second guy she hooked up with and what went down as well as the third guy who topped her and what went down plus a whole lot more.To see anonymous pics of my female guests + get extra exclusive CROSSDRESSER and Hoser episodes/content + get access to my Discord channel where people get super naughty + get early access to all episodes ad free, join my Patreon. It's only $10 a month and you can cancel at any time. You can sign up here: https://www.patreon.com/StrictlyAnonymousPodcast To see anonymous pics of my female guests + get extra exclusive CROSSDRESSER and Hoser episodes/content + hear anonymous confessions + get all the episodes early and AD FREE, join my Patreon! It's only $7 a month and you can cancel at any time. You can sign up here: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.patreon.com/StrictlyAnonymousPodcast⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and when you join, I'll throw in a complimentary link to my private Discord! MY BOOK IS NOW OUT FOR PRE-ORDER!!!! Strictly Anonymous Confessions: Secret Sex Lives of Total Strangers. A bunch of short, super sexy, TRUE stories. GET YOUR COPY NOW: https://amzn.to/4i7hBCd To Join SDC and get a FREE Trial! click here: https://www.sdc.com/?ref=37712 or go to SDC.com and use my code 37712 Want to be on the show? Email me at [e-mail] or go to http://www.strictlyanonymouspodcast.com and click on "Be on the Show" Have something quick you want to confesss while remaining anonymous? Call the CONFESSIONS hotline at 347-420-3579. You can call 24/7. All voices are changed. Sponsors: https://bluechew.com Get your first month FREE! https://butterwellness.com/ Try the Butter Wellness perineum massager and use code STRICTLY for 20% off your entire order Follow me! Instagram https://www.instagram.com/strictanonymous/ Twitter https://twitter.com/strictanonymous?lang=en Website http://www.strictlyanonymouspodcast.com/ Everything else https://linktr.ee/Strictlyanonymouspodcast Learn more about your ad choices. Visit megaphone.fm/adchoices

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And cross-dressers. Any cross-dressers? If you sign up for the cross-dressing, tier it's $10 but you get access to everything all the Pan-i-ho's stuff all the beginner stuff on the regular tier of the picks of guests and the Discord channel as well as exclusive cross-dressing episodes. I posted one episode a month on there but because you're signing up and I've been up and running for years there's tons of exclusive episodes up that you could go and listen to. The Pan-eos tier is $7 a month.

The crush-dressing tier is $10 a month because you get everything. and if you want to sign up for that you go to patreon.com slash trickleine on this podcast the link to that is in the description now today I have on Lily Lily wrote in she's like I'm a pro hormone trans woman married to a woman but I cheat on her with men so I was like oh my god I'm already confused and have a million questions and I asked Lily all the questions Lily is not transitioned with hormones or anything like that but she does fully dress. She's been married twice.

Her first wife didn't know about anything. Her current wife does. And it's kind of interesting that the current wife seems pretty open-minded, considering Lily is at the place where she fully dresses. She's out and proud at a lot of times, even with her children. And the current wife is okay with it. But she does hook up with guys behind her current wife's back. Now, Lily, of course, we go back in time.

Lily started cross-dressing at a very young age. She talks about, you know, her family, our parents, catching her wearing her clothes and them burning them. And so, of course, that turned her into someone who was, like, really trying her not to be who she really was. She always felt like a female at a very young age. She always loved fashion. She's very into fully dressing.

Now we do get into her fashion style later in the way. the call, but she always knew also that she was into guys. She played footsies with guys when she like other boys when she was very young, but she never hooked up with a guy until she was in her 40s, which she is now. She was really interested in having a family. That's why she married a woman. She is more into guys, which is interesting. We do talk about that. Like if she was a always knew she was into men. Why did she wind up with women? But she really wanted that white picket fenced family. She didn't really want to rock the boat. She wanted children. She's a little, she has, she wanted children. And that was the way for her to do it. With her current wife,

this is what, and with her current wife, she dressed right from the get-go. So she was pretty open to it. There was a time where she gave a Lily a free pass at an event to go and get a blowjob from a guy, which she went out and did, but she didn't get a blow job from a guy. She gave a blow job, okay? She's the woman. She wants to blow the guy. That's what she has done. She's also been bottomed after that experience. She talks about her couple experiences with the guys where she's met them, why she didn't start really hooking up with guys until her 40s. Because like I said, she was into men from the get-go and she waited all the way till her 40s to be with guys so why doesn't her wife know that she's hooking up with guys i mean she does talk about the fact that she has brought it up

to her wife that she's into guys she has toys like dildos and stuff that her wife knows she plays with but the wife is concerned with her going out and hooking up with guys because there's fear around that like what could happen so instead what's happening is she's cheating her. So we talk about all of that, all of the experiences. Like I said, we get into the fashion. We get into all of that. Lily sent me picks. I have them over on my Patreon. She gave me all the information with her Fet-Lay profile and stuff if you want to contact her. That's towards the end if you want to see picks of her. I have them on my Patreon. The link is in the description. I'm going to be right back on with Lily. Hi, Lily. Welcome to the strictly anonymous podcast. How are you today?

Oh, another exciting day. I get to talk to you. Yeah, so listen, Lily, we're going to get your whole story. People might be confused at first, okay? Because what you are, you're a trans woman, married to a woman, and you cheat on her with men, right? Yes. That's like what we're going to be talking about, correct? You're pro-hormone, so we're definitely going to go through your whole transition and everything. Let me ask you, the first question I had was like, oh, did you try?

transition while you were married or were you transitioned before and your wife is a lesbian? Like that's what I was like wondering. No. When we, I'm this in my second marriage. So on my first marriage, she left me and went with another like really masculine guy. But you were, but were you transitioned at that point? No. Okay.

I was, I've been thinking about this and doing it since I was like 14, 12. but I live in the Midwest and it's not overly culturally acceptable. Plus, I really wanted children. And you can't do that going through a transition. And so I always sort of knew, but I like hit it. My parents, when I was younger, found my clothing and burnt it in front of me in the fire. So it just taught me to hide things. Of course, yeah.

not to like be who I was. So I was still who I was, but like, you know, just don't show everybody. Don't hide it from the world. So it's sort of a bad precedent you could say right there. Yeah, yeah, yeah. But did your, so did your first wife ever find out that you were, I guess, cross-dressing on the side or on the D.L? She didn't really at the time.

She knows now. And we sort of hang out together. We are in the same, like, bands together and things like that. And she has no problem with it now. Yeah. But with my current wife, when I left my ex-wife, we went out to, as first dates, me dressed up to, like, drag shows. Oh, so you really put it out there to her right from the get-out. Yeah, but I wasn't, like, vocally clear about it.

I did tell her about it. I just sort of dressed. And then she thought it was, like, a fetish or a kink, I guess you were saying more of a kink than a fetish. But then I got custody my children from my ex-wife and I sort of put it on hold

outwardly. You know, internally and like undergarments and things like that I did it all the time. Like I don't own a single pair of men's undergarments at all. Right, right. Fully underneath, you're always fully that trans woman that

you are, right? Like you're a woman. But you were doing that for your kids so that they didn't know when they moved in. Exactly. I didn't want to lose custody of my kids because in the Midwest, it's not as acceptable as well. And any judge could take an opportunity to just take away my rights to see my kids. Of course. So at that point, your ex-wife didn't know about it because you said she does know now. She does know now.

Yeah. And she has no problem with it. My kids are almost 21 and mother-of-son is 21. and we've gone out together to the bars and me dressed up fully with my son. And both my kids are completely okay with it now. They don't care. They sort of already knew what I was because it's not like they didn't see the clothing and other stuff like that in my closet. And they don't care.

My kids, the new generation is just so fantastic and so accepting of whatever you are. Yeah. They don't, as long as you're not like, infringing on their rights or stopping them doing stuff. They don't care. Like, oh, you're happy? Who cares? Fine.

I love it. Yeah, I know. I have some friends that in my generation, I have friends that still say words and have thoughts and have views that, I mean, you would be fucking horrified by like, I hear them talking. I'm like, oh my God, you sound like a fucking dinosaur. And they have kids. And when I'm talking to somebody that is so outdated and so close-minded, I don't even

bother to have arguments with them. You know what I mean? Because they're just, it's like speaking. different language of someone. They're just never going to change, especially that generation of people that think that way. But I think to that myself, like, your kids are going to blow you out of the water. Like, they are not going to be accepting of how you think. They are not on the same fucking page. They are so more evolved and beyond. And they will look at you like, what's your fucking problem? Do you know what I mean? Because they are open as they should be.

And that's why I sort of feel with my parents. It's like, really, that mattered to you so much that what clothing I wore when I was a kid? Yeah, well, listen, I think back in the day, especially, well, how old are you, first of all? Like, I need to get the whole story from the beginning because we're kind of jumping around. But like, how old are you, Lily, now? 44. 44. So, like, this was a long time ago, you're a kid.

I, like, listen, I, as much as I talk to people from your angle, I once talked to a parent of a transgender child. And it was really interesting to get their view because I do think that a parent that was dealing with that goes through something themselves, right? And listen, some parents are just going to be cool with it from the start. And that is the top of the mountain. That's who you want to be as a parent, right? But not every parent is there, especially back in that day. Your parents found your clothing and like, what the fuck. You could understand that they'd be horrified and not know what to do it because think of the generation they grew up in. You know what I mean? Like But the fact that they burned it and they put that shame, I mean, like, these are all the things that it's just like, wow, we as a society need to do things different than that because that kind of shit didn't work, right?

It didn't make you change. It just made you have to repress who you really were because that's who you were. You know what you mean? But they just didn't know how to accept it. They didn't know what to do with it. They didn't talk to about it. They just burned your fucking clothes. It's fucked up.

Yeah, I wasn't happy. I was depressed a lot of times. I was not being able to be who I was. Yeah, to me, that's the gift you give your children. I think that the foundation to have like a solid child is just like really make them know that you love them for exactly who they are, whoever they are. I just aired an episode. It was this guy, Jamal, and it was such a great fucking epa. Did you hear it?

The prison. The prisoner. Yeah, he went to prison. Listen to his fucking story. This was a kid who had his mom abandoned him. And then when his dad saw that he was like flamboyantly gay, like he was obviously. gay at like six years old, his dad axed him out. It ruined his whole life. I mean, there was a happy ending to that story, but this kid suffered. You put things on to your child, and it's not

fair. And then they have to untangle that shit. So I think it's so great that we have kids that are open-minded, and they're not going to do that shit to their kids. But so you got, you had to repress it for a really long time. But let's go back to your story from there, and we'll get to eventually to where you're cheating on your wife with guys. But like, so you knew early on that you were a woman even though you were born male? Yeah, I had a really good feeling. I always sort of questioned it

at that age you don't really know. But everything kept bringing me back to that. Like, when I never really like the whole like rough and tough play that the guys like to do. I liked fashion, beauty, design. I like to talk to people.

I liked just being around other ladies, not like a creepy way. not like hitting on them, I always want to just be around that kind of environment. So after, let me just ask you this. So after your parents burned your clothes, right? I mean, how old were you at that point? Do you remember what age?

Probably, probably, well, I was not driving at that time, but I was able to bike to targets and place like that in Kmart. It was mostly Kmart. Right. So you were able to go and do stuff on your own. So you weren't like six or seven. You're like probably 12 or 13 around that age. something like that.

Yeah, but yeah, around there somewhere. Mm-hmm. But before that, I had to do the classic cross-dresser thing of barring my parents, my mom's clothing, the panty hose and all those kind of things. And I found my parents' adult magazines poorly hidden under the stairs with Victoria's Secret catalogs and stuff like that. And I didn't like pleasure myself to those pictures. I just imagined myself wearing those clothing. Right. Interesting. So there was like an added layer because like a lot of kids, boys, right, would find those kind of magazines and be like horny for tits and ass that they see.

But you identified with those women. You want to be those women too. So it was like a step further. Were you also turned on by them? Turned on a little bit. I sort of like both. Yeah. But it's like I don't actively like seek out women to spread my seed with per se.

You know, I've... But it's interesting. That's what I thought the first thing. I'm like, if he's like hooking up secret, like if she, right, Lily, I should call you she, right? If she's hooking up with men on the side, like, why marry a woman? Why are you not with a man? Traditional gender role fitting into society kind of stuff.

Right. Wanting to have the family and you can't really, I can't really have a family, my own traditional, you know, doing it that way without traditional way. Right, right. So it's not so much exactly what you want. It was something for you to get those things that you wanted and fit in. But really, if you could have what you want and there was a way for you two dicks to get together and make a baby. And there is nowadays.

You could go do a lot of things to make a family, right? But you would be married to a guy. Very possible. Very possible. Mm-hmm. Okay. So you're dressing up, you're finding that porn. Are you still questioning not just your sexual?

but your gender? Because that's two different things, right? I mean, I feel like that's... Yeah. That's, you know, listen to homosexual children are just questioning their sexuality but not their gender. You had two things going on, right?

Were you confused that you liked men too? Yeah, I was. And, like, I would play, like, footsie with guys under the table at places and things like that and never really did that with girls. But, yeah. A lot of looking back, And it's just like, and like when I was, when I got married the first time, my ex-wife, people came out to my parents and said, oh my gosh, I always thought he was gay.

Wow. So, yeah. So people knew in like my high school and things like that. And I had, I was still questioning and doubting it and trying to fit into a mold, I guess you'd say. But you knew, but you always knew. I sort of always knew, but like I hit it and repressed it and doubted it and tried to. change it and not be it yeah yeah because that's not acceptable you grow up in a household and you have to do what your parents like that's evolutionary speaking if you don't not really i mean i didn't

do anything that my parents like i mean you can be rebellious in the history like if your parents didn't like you and you're a baby in ancient times yeah you just been killed so it's like ingrained in us to please our parents to a point i guess how come it wasn't ingrained in me i think it's a different personality types. I do think it's like this golden rule kind of thing. You do what your parents say. Yeah. A lot of it for me, my rebellious sides were led into my destructive lifestyle. I didn't do drugs or anything like that, but shoplifted and didn't care if I got caught and depression and things like that. Of course. I mean, you couldn't have been like a happy person not being accepted and trying to figure out how do you be exactly who you want to be like you said and have the things that you wanted. Here you were a trans woman.

who liked men, but you wanted to have kids and be accepted by people. And there's nothing wrong with wanting those things and wanting to be accepted. Who doesn't want to be liked? Who wants to go out and be fucking shunned for being who they are? I get why you wanted to fit in. But, you know, how troubling that at a young age, you don't know how the fuck that's going to happen. Mm-hmm.

So when did you start hooking up with men? Actually, besides the footsie thing when I was like in high school, just recently. Oh, wow. So even though you had these desires, you hadn't fulfilled them until your 40s? Yeah. Wow. That's interesting. Now, if you're pro hormones, are you on hormones? Are you transitioning now? Are you fully transitioned? I'm not fully transitioned. I use. shapewear and makeup to achieve my look. Okay, right, right. But you consider yourself trans because you,

it's not like you're just cross-dressing. You are a woman. You're a woman 100%, right? When I feel. Yeah. I can't portray it all the time. Like jobs and things like that. So I was working for a large motor manufacturer

after my kids got out of high school. So when they got out of high school, then I started expressing myself as I am. And I just did that mostly because I didn't want to embarrass my children, have my kids be the laughing stock of the town, have them teased, have them not accept me and hate me or anything else like that. But it turns out I didn't need to. I could have done it 20 years ago.

But I waited until they were on their own so that I could be myself. But at that time, I was working for that major motor company. And I started doing my nails. and makeup at work, and they came up with excuses like, I'm racist to fire me. The union investigated and determined that my work ethic was higher than expected by the company, and that I made people uncomfortable at work because I expected them to lower to my standards of production, which would be doing the job correctly for everyone else. So that was the reason I was fired because I started wearing my makeup and painting my nails at work.

Oh, wow. They say I'm in as an at-will state, so they can just say whatever they want, but they made excuses up why they wanted to get rid of me. Right, of course. And listen, that shit goes down. I mean, like, it's not shocking, which it's horrifying because it's terrible to do to somebody, but it's not shocking. I live in New York City, so I forget that there's a whole middle of the country that is very super closed off. Sometimes when you live in a place like New York where it's, there's more acceptance because you're in a city, right? You forget that in the middle of the country, there's a lot of, uh, uh, stuff.

Hell bigotry. Yeah, still going on. It's terrible. So now when you met your first wife, your second wife, that whole time you're hooking up with women. Do you enjoy being with women at all sexually? It's, it's fine. The end result, the end result is there. but I wouldn't call myself a great manly lover

I don't deliver the goods like we'd expect I guess you'd say well like with your first wife do you did you fuck her all the time or would she say looking back like wow it was obvious that you weren't into women because we didn't have sex that much or were you super horny so you were just like using her anyway because it was all you got because you weren't fooling around guys. I didn't really initiate it that much.

It was more her initiating. And we tried the polyamorous, like, swinging lifestyle thing. We said swinging curse and then sort of did polyamorous. And the polyamorous person she brought in, they would go and do stuff like in the room. And they'd be much longer. And she sounded like she enjoyed it a lot more than she ever enjoyed it with me. And it was a guy? Yes. Now would you be turned on by that?

No. No? Okay. No. At the time it felt like it was sort of frustrating that she wouldn't want to do that stuff with me. And then she ended up marrying him later too. They're still to marry now and have two more kids. Right, right. But you could understand now, but maybe at that point it was just like you were in denial really of what was going on with you that you couldn't understand why she would be feeling that way with him, right? Yeah. And she looked back to that. and sees it too. Right, obviously. So now your second wife, was that a conscious decision?

Like, I'm not going to get in another fucking relationship like that. Like, I'm going to put it out there because you weren't cross-dusting in front of your other wife, right? Your first wife. I was not. I was not doing anything. So this one, you met her. Why with her did you go in, like, dressed up right from the get-go?

Because the reason why I thought my ex-wife wanted to leave me is because I wasn't what she thought. I wasn't manly enough for her. And I was going to let that come out right away. I'm not Right you wanted this time For someone to like you for you for you As opposed to you pretending to be something that you're not

Yeah Okay so that's a pivotal point for you I think That's that's great that you finally were at the point Well I'm not gonna fucking do this bullshit lie thing again Yeah But then I got testing my kids And then I sort of just put it on the back burner I didn't fully dress up

I would have undergarments and like I shake my legs. My hair's all gone on my body. I despise it. But I'd wear like kilts on the outside and stuff like that. So I sort of had a dress skirt on most of the time. But I did what I could do culturally acceptable in public around her too. But she thought it was I get just as a phase because I didn't do it as much as I did the first time.

And did she know, though, that you were wearing the undergarments always? Oh yeah, she knows all about that I don't own a single pair Right, so she would have to know Yeah, one of the things too It was like they realized it wasn't really a kink for me Just wearing panties We were intimate once

And she grabbed my underwear and was pulling on it And I was like I was freaking out Because I thought she was going to ruin my underwear By ripping it But it was not something It wasn't because I got off on wearing underwear It's that you like them That's your underwear

It's my underwear. I don't want it to be destroyed. Yeah. And after that happened, I never did that again. I was just, yeah, I didn't want it ruined. So did she ever ask you any questions? Was she confused at first? I would think that she'd have some questions.

When I fully, like, started, you know, going full out all the time. There's a lot of questions about what I want and am I going to transition and do you want a relationship with me? me and all those kind of things. And how did those come? What did you say? I do want a relationship with her. I do love her. I do care about her. I would like it if the relationship was more open, I guess you could say, where I didn't

have to fool around on the side, I guess. And my dalliances are very minimal. It's not like I go out every Friday and find random guys at the bar. Oh, we're going to get to your dalliances. But what I want to know is that, like, when she comes to you and says, you know, and asks you the questions like I'm asking you. you. It doesn't sound like you were completely honest. Because when I asked you the question if you're gay, it sounds like you're gay. Like it doesn't sound like you're by, really. It

sounds like you prefer men and would be with a man if you could. But for some reason, you still have the desire to have her around and live your gay life on the side. That sounds like it's a lot more internal work I need to do with my counselors. So you very well could be right. Yeah, nothing wrong with that, of course. But you're just not ready to accept that maybe? How do you... That's the possibility.

Like, the expectations of family, culture, parents, what I thought I should be. The last thing you want to do is go to your family who's still alive. Your mother, your father, your aunts, your uncles, your cousins, like admit that you're gay. Possibly. Yeah, I haven't really thought about it. Like, my sister knows.

that I dress up. My brother does not. I haven't talked to my brother in many, many years. My mother has Alzheimer's, so she doesn't remember me. And last year, I was at a band concert. I play the French horn for community bands. And I'm fully dressed up. And I didn't invite my parents, but they randomly showed up at this concert I was at.

Wow. So I was freaking out, and I didn't invite them. It was far away from the house. My dad likes free concerts. I didn't think he would be there. Yeah. Oh, my God. And he was, I was freaking up the whole time.

My ex-wife was there, and she plays in the same band, too. And, yeah, my dad goes over to me after the concert and says, so what's up with this? And it's like, well, I'm not living at your house anymore. you can't control me and then he wants a picture of me with my mom so she can remember what I do I guess I'm not exactly sure why he wants the picture it's not like he's talked to me since your father correct after that he stopped talking to you pretty much yeah oh okay he was very that really freaked him out yeah I was just thinking maybe like saying you're gay isn't really correct because you are a woman that is interested in men right

Right? So does that make you heterosexual? It's a little confusing. Yeah, I feel that same way. It's all very confusing. I mean, what is the right term? Because if you, you did call yourself a trans woman, right? I mean, do you identify as a woman, correct? Correct. But I'm not fully. Like, I'm never going to be that full thing unless we have some kind of magic spell that changes everything. So even the surgeries are interesting, but you do. And that's another thing that sort of deterred me from going full out is the badgioplasty surgery is interesting. Like the whole dilation process and everything else.

And it's sometimes you lose all sensation in that area too because you're basically cutting nerves. So I'd basically be making a hole for a guy to please himself in, which at point sounds fun. But what do I get from that? It's not the same. Right. And now when you hook up with guys, are you like the bottom because you're the female? I have no interest in topping guys. Right.

So if you didn't have your cock, you'd be totally fine. It's not like a part of that play for you, right? Yeah. It's not. It does have the proper nerve endings that work. Yeah. But it's not as much fun. And I don't get as excited.

Just, yeah, I love like sucking a cock and deep throating. That's just so much. much fun. I like that so much more than I've ever going down on doing kind of like us. So let walk me through. I'm a little all over the place somehow in this story, but that's fine. It's super interesting. Walk me through your first time with a guy and how that happened and why it happens. So, so I have some other friends and they are nudists and they invited my wife and I out to the nudist colony in the same state, a little distance away. And at night, one of the nights at the nudist colony, there's, like, you don't have sex

in the colony area, I guess you'd say, but they have this little backward, backway place, way off the distance. And there's still their property where people do hook up. So completely nude, except I did all my makeup up and everything else like that. And a guy there was hitting on me and there was alcohol involved and we sort of went back to the back start back area. After talking for a while, he pulled on his pants and put his cot to my face and I just enjoyed the time keeping him pleasure for a little while. But after a little while, I guess he was too close to finishing or something. He just sort of like stops me completely, pulls out, pulls those pants, doesn't say anything to me, and just walks away. I'm like, what the hell? And he gets

starts talking to other people in the area. And I still had fun time doing it. It was very exciting for me. Like that naughty, risque kind of thing. And maybe it was part of the thing that my wife said, you can get a blowjob when I was at that event. That sort of gave me a little bit more permission. So I sort of interpreted it a little differently, I guess you could say, in my mind and my drunkish mind. but he was like hanging out with other people talking to them like trying to hook up with them I think in that area too and then like three hours later thinks he's going to come over to me and talk to me and get back with me no sorry you lost your chance welcome to the world of being a woman exactly it was yeah it was interesting guys are could be selfish yeah oh yeah I see it too yeah it's just it's really weird yeah so that was and I just sort of went back and went back and went back to the room. But your wife had no idea that you had a dick in your mouth. That was the first time. I would think that that's like a pretty major experience for you considering all your life. You've been kind of thinking about dick, probably jerking off to it. I mean, this was like your actual first experience. Kind of like a big deal. Yeah. I still think about it. And I wish it would have worked a little differently. But most people's first experience in SAC with sex doesn't go good. It's kind of like losing your virginity. You got to look at that. Even though you were like 40, it was like your first time with a guy. Maybe you didn't give good head. It was the first time.

You didn't know what the fuck you were doing. Possibly. Possibly. I don't know. But you were deep throating. So, I mean, how did you know how to do that? I've been practicing for quite a few years before that. Oh, okay.

So you were blowing things like bananas and shit. Like, what were you blowing? Bananas and I have some dildos and stuff like that. Oh, okay. Yeah. Makes sense. Right, right. I'm like forgetting all these things.

So you had always had like a collection of toys that you played with. Did your wife ever know? about those toys? Were they hers? My first wife, no. My current wife does know. She does. Yeah. The kids are gone. I leave them on the counter sometimes in my dressing room. So she knows you play with like cocks, toy cocks, but she's never like, do you want the real thing? I've told her I want the real thing. Oh, you have. She's not ready for me to do that yet. I've, have told her, yeah. Oh, okay. I don't know why I missed that. Did you explain that before? Oh, that's okay. I did not say that before.

Oh, okay. So when she had those conversations, because I said, like I asked you, like, does she ask you questions and stuff? And what do you say? And it sounded like you didn't really let her in. But you did say that you would like to be with men. Yeah. When we first got together, I was dressing, we also went to a few swinging parties. Like, so there was that environment I enjoy, the openness, the creativity, the not

giving a fuck and just being yourself kind of thing. Yeah. But those sort of died off. But, yeah, we had to the little bit of the kinky side and me for sure. So what did she say when you cop to it? When I went when I what? When you cop to it. Is that why she said you could get a blowjob that time, like from a guy?

Is that what was a part of her because she knew that you liked men? I don't think she thought that. I think she probably thought it's okay. Since we're at the nudist resort and there are these things that happen there that if I were to get a blow job to be okay. But was it from a guy or a girl? Do you think she was thinking? I think she probably thought for a girl.

Okay. Okay. But I mean, listen, that was your window of opportunity to like fucking make more of this available to you and make her more okay with you actually giving blow jobs and stuff. Like that was your time. Here she was giving you a free pass to finally be with a guy. and it didn't really lead to any more conversations or anything after that?

Because, I mean, I'm assuming not because you're cheating on her with men. We still talk about things. I still bring it up and it's getting better. Like me dressing in the first place, it's a lot better. When I first started doing it, she was like totally freaking out. And now I go to the grocery short, dressed up with her completely. Wow, that's amazing. So it's in like a two to three year period

And it's Coming over quite well like last Fourth of July I went out completely dressed With my daughter and my daughter's Fiancé to her fiance's Parents' house for Fourth of July fireworks Completely dressed up

Now how possible are you? You wear shapewear and stuff And do you wear the forms so you have breasts and all that kind of thing I have the forms but I also do other tricks to create cleavage and things like that. Of course, you'll get pictures and we can see those. And hopefully you feel I'm passable. I mostly think I'm passable enough sometimes. But, of course, I look at myself in the mirror and see the guy face.

I just hate that. But, yeah, people say I'm gorgeous. I don't see it. Right. When you're dressed, do you mean? As Lily, like your, Lily is gorgeous. Yes, but I still don't see it sometimes. I still look at my mirror even in the makeup and say, oh my gosh, how can people be confused?

How can they not see a guy staring back at him when I'm dressed up? Right, but that's your projection. And it's because you have not fully come to terms. That's what I think. I think that you're, you think everyone sees what you see. That's like dysmorphia kind of thing, you know, because, and I think it's because you're still like, even though you're with a woman who is super accepting and you've gotten to the place where you're walking out dressing. I mean, you're a lot farther than most people. You still have

not fully committed to really who you are. And I think that's why when you see even a hint of that person, it bothers you because it's a reminder of like what you're not okay with, what you're still confused with, where you're at, not other people. Yeah, it's very possible. I always question if someone's saying I'm gorgeous because they want something for on me more than them being generally honest. Like my daughter has helped me a little bit realize that if it generally comes from a girl, they're saying you're gorgeous, you're probably fine. Yeah, but listen, this is like men will say this all the time.

Like my wife gained five pounds and she doesn't feel sexy, but I tell her she's sexy all the time. And I'm like, self-esteem comes from yourself. It doesn't come from other people. So it doesn't matter what other people say. It really matters how you feel about yourself. So people could tell you you're gorgeous. all the time. If you don't feel gorgeous, it doesn't matter. They can't change that view of you.

You have to change that view of you. Yeah. I feel it at times. I definitely feel a lot more confident. I feel like more powerful. I feel attractive when I have everything on. Yeah. Listen, I think probably a lot of that has come with you being more out and proud of who you are. I think that I'm sure that goes hand in hand with the more open you've been with yourself, the more gorgeous you feel, right? Yeah. Now, how do you like to dress? What's your style? Your fashion.

You probably say like classic style. Like everything put together. You know, like if I have a dress on, then I need the corresponding makeup, the hat and nail color, the whole works, hose, everything. Everything has to coordinate and match. So I currently drive deliveries for a huge company and I have this annoying blue uniform. And I had to make a hat for myself out of the uniform shirt just so I could first protect my skin because the son's evil on your skin. Yeah.

Makes those wrinkles. I got to protect that. I can keep young as I can. Uh-huh. And I made it from one of the shirts. Uh-huh. So I have a coordinated hat with my shirt that they've got. that they make us wear and everything else.

So yeah, everything has to be planned out. I have this obsession with, once I wear an outfit, I don't usually wear that outfit again, which is sort of terrible because it's horrible on the budget. But I'll use elements of other clothing to match things together. Yeah, never actually the same thing twice in real, not the same exact way. Right, right.

So you're picky. You like to be fully dressed. You're very into your fashion. And like you said that, you were very into that at a very young age. Where do you like to shop for your clothing? Oh, I love to do the high-end stores, but those are just a little too pricey sometimes. So usually Amazon has most things you want. And just walking around department stores are nice.

Like they used to have Macy's and things like that. Macy's still exists. Elis Ayers was one of ones in my area. And Macy's I still go into. And the general public ones. I don't have that kind of money to have $300 dresses every day. Yeah, yeah, yeah. Who does, right?

Yeah, but, you know, that's why they have these consignment places and stuff online and you could buy from other people like Poshmark and stuff like that. Yeah, I like those kind of places. I like regular. I like walking in the consignment store too and just talking to people there. So they're a lot more accepting too when I show up certain ways. How, like, do you have a thing where you a wannabe called she or he? How do you feel about your pronouns?

So with the pronoun issue, I'm not going to, like, force somebody to use a different thing. Mm-hmm. I don't think we gain acceptance by throwing a tirade and a fit in a store, throwing things around the store because someone calls you the wrong pronoun. Right. If I look a certain way and I'm doing a good job and you say she, that's fine. If I'm not, maybe I don't look on point that day and you say he, it's like, I'm not going to worry about it. I'm not going to, there's all these viral videos online of people getting upset with the wrong pronouns. It's like you're not going to change people's mindset if you yell at them when they say something wrong.

Right. But are you a she or a he? Like what do you say is your label? I like she more. I feel a lot better when someone says she. But if I'm, again, if I'm not doing a good job. And pronouns are just to help identify things. Instead of saying someone's. name because you don't know everybody's name. You say go to that person over there. It's like there's five people there. Who are you going to go to? If you go to her over there, it might be more clear. So, yeah.

Yeah, listen, I think a lot of people get really freaked out about these pronouns and stuff. And listen, I understand that they could be super important to people. I remember when I used to write descriptions, I just started making sure that when I write my cross-tressing descriptions, I write she. When somebody was like thankful for that, I was like, yeah, I think maybe three, years ago, I didn't do it that way, right? But I think it is important, but sometimes it could be confusing. And it's cool that you understand that, you know. Some people are a little bit more, like you said, they get a little bit more upset. I think it does. It is confusing even for me, right?

I'm like, oh my God, I'm talking to you as if you're a man, but you really are calling in as Lily and you are a woman. Let's get back to the cheating though. You had that one guy. How many other guys have you been with? I have sucked. three other cucks and two of those other guys that fucked me too. Okay. So now after that experience, how did you wind up going out and meeting other men? And when you're meeting these guys, you're always fully dressed, correct? Yes.

I'm not in male mode at all. Even all the way down to the toenails. Right. All the way down to the tone else. Love it. Okay. So how did you meet the other guys and what went down? Considering that you must have had your first getting topped experience.

I'm sure you've heard of what I was like that life. Yeah. Yeah, so I have a profile on there. And a guy in my local area was talking to me for a while. And I was a little skeptical at first and worried what he wanted. And I wanted to meet out in public first. So we met out in public at like outside a restaurant and then later went in the restaurant, talk for a while, then went back to his house and future dates.

And we started sort of making out, gave him a blowjob, but then he like stopped it there too because he didn't want to ruin the full experience and I guess wanted to do it gradually with me. And it's not like he didn't take care of me at that time. It was very enjoyable. But when I was out, since I haven't really fully told my wife, she had to, with modern technology on phones nowadays. It's very irritating to do hookups with someone not being able to watch you, I guess. Right. Because GPS, she said, why are you in this random house somewhere else hanging out? Right. So I sort of called it quits on that guy because I don't have an excuse why I would be at this random person's house. And to go there again would be very questionable. Right, right. Okay.

The third guy, I said I deliver for a large company, and he had found me on Instagram, and he was very smooth talking in his house. And originally I was just going to drive up to his house and visit them and say hi. But he very smoothly, like, got me into his house, which, again, I should not have done because who knows what it would have happened in his house. But I'm here now, so I'm alive and everything's okay. Oh, he just wanted to suck your dick. I mean, I mean, you want you to suck his dick. Well, he did a little more than me sucking his dick. Yeah, I mean, I'm just like, most guys, I think more guys are just horny perverts than they are murderers.

So you're more likely to get a guy that's going to offer you to come in and blow him than a guy that's going to chop you up. You know what I'm saying? Yeah. We watch too many crime shows, though, like FBI. Oh, listen, I know. I'm right there with you. Yeah. You think these things afterwards, like, oh, my God, what am I thinking?

Why do you think I'm not married? Because I know for a fact, my husband would kill me. I have a mouth on me. You know what I'm saying? I'm opinionated. I'd wind up, chopped up in a fucking garbage bag. Yeah. At least I sort of like the living thing that I want to live my life.

And when it ends, it ends. But I want to enjoy those times. All right. Well, it's not going to end when you're with a guy. Let's get to this story now. So the third guy, where do you meet him again? Instagram. Okay, right, right, right. So you go and how, so this is the first guy that actually tops you, right?

Yes. And how was that? Oh, it was pretty good. He was big and very enjoyable. And he first took me into his kitchen. And I pushed me down, like nice and controlling, grab the back of my hair, pushed me on him a little bit. And let me sort of control. Yeah, but he had that nice aggressive kind of tendency with him. then you know pick me up condoms and all this stuff of course always always always condoms and safe stuff but pick me up literally pick me up and put me on top of his counter in his kitchen yeah and just like pulled down my work uniform and just lubed up and went at it and like slamming myself me into the back wall of the kitchen too it was not like bad but like

very enjoyable then put me down again switch condoms put his dick back in my mouth and then we went back into his bedroom and on his floor. So he didn't actually have a bed. So it was probably a squat place. Who knows? Yeah, yeah, yeah, yeah. God knows. I mean, did he have a wedding ring on? No. Okay. I did see a wedding ring. And then he ended up moving away because he said he lost the house. So who knows? Maybe he just did his one time and it was done. Yeah, yeah, yeah. Let me ask you this, though. You sound like you were always faithful to your wife all the way up into this point, I'm assuming. Yeah.

So how did you feel after you started doing this stuff behind her back? Was there ever any kind of guilt? Surprisingly, no. Mm-hmm. I feel like... That's honest. I'm figuring out what I like and what makes me happy. And I'm working toward the point where I be fully out with my wife.

I told her that the things I want to do and where I want to go. But yeah, it feels like it's experimental time right now for me, I guess you could say. I don't feel like I'm really cheating, but basically I am. Mm-hmm. I mean, you need to start having more of those conversations with her about you being able to hook up with other guys. Because you've had them already. She gave you a free pass. I mean, like I said, there was that window of opportunity.

It sounds like you're so close. You've sort of admitted so much to her. I don't understand why you haven't been able to have that conversation with her that you want to or need to hook up with other guys. I think a lot of it is she's worried that for some reason she thinks I'm the best relationships you ever had. And I think she's worried about losing me too if I were to be fully out and I would just leave her for a guy. Of course. I mean, in a weird way, like I'm sorry, I was just thinking before. I know that you love her, but don't you think that if she's, you know, fully heterosexual herself,

that maybe at the end of the day, if you left her for a guy, she'd wind up with a man who really just wants to be with a woman and don't you think she'd maybe be happier? You might be the greatest relationship she had, but is it the, maybe there's something better and she just doesn't realize it, because how could a guy that really doesn't even prefer women be that best relationship? I just don't feel like you guys have everything that you would be able to have with other people.

You with a man, her with a man. Do you know what I'm saying? Yeah, I understand. It's probably a little bit of giving up the security and a comfortable life. Yeah, that change is always hard, and she's holding on to something, and you're holding on to something. but is what you guys are holding on to the best that you could ever have? No, I think you're both lying to yourself.

I mean, how many times a month do you fuck her? Is zero an option? Yes, that's a truth, right? I mean, so how does she feel as a woman? And she's in her 40s? She's in her 50s. She's in her 50s. Is she through menopause? Like, does she not have a sex drive? Maybe so that's why it works. I think that's part of it. Yeah, so she might be at the place in her life where she doesn't even have. that desire so I could see why your companionship and you not wanting to have sex actually would

really work. It is the best thing for her. Do you know what I mean? Yeah. How long have you been with her for? We've been together 17 years. 17 years. So, but like through that time when she was in her 40s and super horny and all that stuff

before she goes through bed and pos, like, most women go like really horny. Did you not really have that much sex? it was probably more like two times a week or so right okay that's not bad so it was like kind of normal for a long-term marriage so i understand like you said giving up that comfortability and stuff but you know if you're going to stay in this marriage and it works for both of you and i think you know that's what's most important that both of you are happy it's not what other people think or how it looks on paper it's how you guys feel i think you have to get to a place with her if you guys we're going to stay together.

You tell her exactly what you said to me. Like, I love her. I want to stay with her. I want that relationship to stay in my life. But, you know, you also want to be with men and you need to get that okay. So you could be exactly who you are and be accepted for once. And I feel like this is the woman that will probably give that to you. I think you just need to have more conversations with her because she's super open.

And give her time too. Well, it's 17 years. I don't think it's time. I think it's you, it's not time. It's more conversations within the time. I mean, how many times have you brought it up? It's just continued talking and continued conversations. It's not time.

It's more times of talking about it. I mean, in 17 years, you haven't got there yet. How much fucking time do you need? It's not about the time. It's about you being, bringing it up and really making her understand that this is something that's important to you. And giving her. that security that she wants. She wants to know that you're still going to be there and she's still going to have that companionship that she has with you and what you guys have together isn't going

to go anywhere. Yeah. I mean, because what's the other, like what happens if she finds that she's, you're cheating on her? Like, what does she do then? I don't know. Like, I just think it would always be better to try to be more honest, especially in this situation. You're not with a woman who has no idea of anything. I mean, she's just a woman that's going to the store with you, fully dressed up as Lily. This is a woman that, gave you a free pass to go get a blowjob from a guy. I mean, this is a pretty open-minded woman. If anyone can accept that it's her, you need to push for it more. You need to be more honest about your desires to be with men so that you don't continue to live a double life. There's no reason

that you as a woman who is dressing up and is so open and is fully out and about as far as you are to not be able to have that added extra acceptance of that part of your life too. There's no reason to be doing that undercover. Yeah, I agree. And if you really love your wife, you wouldn't want to do that to her because if she found out, it's not just, oh, you're doing that. It's like the betrayal. It's like the distrust.

It's like the lying. And that becomes a whole different other thing. I think she would be devastated. I wouldn't want that myself either. Yeah. Right. So before you get caught, because this is not going to go away. it's been you for so long, try to get to a place where you could try to start having those

conversations with her again, especially because if you're not having any sex anyway, get a free pass. Get more free passes. Listen, we're not doing anything here. You're not horny anymore, but I would like a free pass, but I don't want to go out with women. I'd like to be with men. And I have no intention of leaving you. I love our life. Like this works for me. I am not ever going to leave you for a man because that's not a lifestyle that I could ever fully accept. And that's okay. But let her know that. I think that would give her security.

Yeah. She has said that a few times. Like, if I were to go another location, it's okay to do certain things, but not like around home. So you tell her you won't do it around. Give her whatever she wants. She's got to have some saying it.

Of course. You have to take her into consideration. And you have to ease her fears because they're valid. But I think that you can ease them because I don't think that you might ever get to the point where you could ever fully live like the way you wanted to and that's okay but if you could like have your wife who you love as a person right and project and who gives you that projection of like oh you're you're with a woman you're a man and you don't have to deal with your family knowing anything

right who gives you all of that she's like your beard she gives you the beard you also love her you like her companionship you like living with her and you could still go out with other men like that's probably the perfect life for you. And I think that you could have that and you should strive for that. You just need to have more conversations, be more honest with her and also hear her out and give her what she needs. But let her know that this is something that is as definite. This has to happen. And I think that she'll allow it as long as you give her the security that she wants because that's her fear, just her fear of losing you.

And tell her you'll go far away. Give her whatever she wants. And send me picks. Okay. So listen, Lily, I love this conversation. It's super interesting. Send me picks. I'm going to put those up for my cross-dressers and my hosers. We'll get to see you fully dressed. I have a new thing on my Patreon where for the cross-dresses and the hosers, you know, they always look to like talk to each other. And so I'm putting together like a contact list of everybody's fat life and emails if people want to get in touch. Because a lot of times I have someone on and my hosers and my cross-dressers want. want to talk to them and ask further questions and get in touch. So I'm going to start asking everybody who calls in if they want to include like their FET life or email.

Do you want to include any of that? I think I'd be okay with that to talk to people. Yeah, yeah, yeah, yeah. Other like-minded people. I don't mind giving advice and helping people and getting other, picking up other advice for people too. Yeah, yeah, great. So give me your FetLife name and I'm going to include you on that email list and then I will

I'll add you on there when your episode airs. So then you'll be on that contact list for people and I'll make sure that they know that you're Lily, right? So do me a favor. Email me or give the shout out for your fat life right now. Lilith M. Kiefer. Lilith M. Keefer. Yeah. L-I-L-L-I-T-H-M-K-I-E-F-F-E-R.

Okay, Lilith, Lily, I will put that and your email, I'll post that and then send me some picks. Awesome. All right. You're the best. Thank you, Lily. And then, you know, when your episode airs, I have a private discord that my Patreon members pay to be on.

But because you called in, you'll get a free link to go on there and talk to people if you want. Okay. So I'll send you that link to right after your episode airs. Awesome. Thank you very much. All right. I had a good time.

Awesome. I'm so glad you called in. I like to talk. I like to run my mouth. I'm terrible. No, no. Listen, I need an hour show. I like people who like to run their mouth.

We got to talk on my show. So it was an interesting conversation. Thanks so much for calling in. Thank you. Thank you. Bye. Okay. I just want to tell you before you go that my book, it's called Strictly

Anonymous Confession, Secret Sex Lives of Total Strangers, is now available not only in paperback and ebook, but you can pre-order the audio book. It's still not going to be out until August 25th, but you can pre-order it. The book is basically 17 different stories. taken from my show. I kind of picked one story from each category that I talk about on my show. Like there's a hot wife story. There's a cuck queen story. There's a cuck story. There's a gang being girl story. Like I said, 17 stories. And they're all told in the third person. And they're all true. I took the interview and rewrote it in the third person. And I wouldn't really call it like

a total erotica book. Think like Penthouse letters. It's more direct. It's not so over. the top like erotica. I don't really like that kind of vibe, right? But these are true stories. 17 of them. They're really short chapters, easy read. You could read, you know, one or two and then skip around. You could read the whole book. It's available in eback format, paperback format, and finally, the audiobook is available coming out August 25th. But you could pre-order it now. And if you buy my book in any format or pre-order it, I will throw in a complimentary link to my Discord. My Discord does not disappoint. Okay. There's no way you get into my Discord any other way than getting the link from me. Okay. I give it to people who buy my book. There's tons of people in there.

Everybody shares content with each other and that's what you get to do there. You could post your own pictures and videos. There's tons of channels. We have lots of contests where you can win a lot of money. It's a super fun place to be. It's a total strictly anonymous community and you will love it. I will be giving anyone who buys my book access to my Discord. It's private, like I said. All you got to do is email me a screenshot of your purchase, whether you did the audiobook, the ebook or the paperback. Send it to me at Strictly Anonymous Podcast at gmail.com.

That's strictly anonymous podcast at gmail.com. And I will send you the link to Discord. So anyway, thanks so much for tuning in. It's the Strictly Anonymous podcast. Hey, everyone. Thanks so much for tuning in to this week's episode. If you want to follow the show, follow me at Strict Anonymous on Instagram or Twitter. That's at Strict Anonymous.

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