Strictly Anonymous Confessions - 1154 - FETISH FRIDAY: Jack is a Fluid Crossdresser who is Totally Into Prostate Play

Episode Date: June 27, 2025

Jack is a fluid crossdresser who is totally into prostate play and he called in to talk all about it. Tune in to hear him discuss all the details including how and when he realized he was into wearing female clothing and what he enjoyed about it at first, when he got into trans porn and exploring anal play, his first hook-up he had with another crossdresser and exactly what went down, his stash he was accumulating and where he gets everything from, how he told one of his girlfriends that he was into pegging and how she reacted, the first guy he hooked up with and exactly what went down between them, how he brought up his crossdressing and his interest in guys to his last girlfriend and how she reacted and what followed including him getting pegged by her while he is dressed, how and why they broke up and how she threw his fetish in his face at the end, the prostate orgasms he has had and how they feel,  the anal toys he enjoys the most and the ones he recommends to start out with, how he got a throat infection from deep throating a toy one time and how long it lasted plus a whole lot more. **To see anonymous a pics of JACK plus see pics my other female guests + get TONS of exclusive CROSSDRESSER and or HOSER episodes and content + hear all the anonymous confessions, join my Patreon Crossdresser tier it's only $8 a month for Hosers and $10 a month for crossdressers (you get also get Hoser episodes too!) and you can cancel at any time. You can sign up here: ⁠⁠⁠⁠https://www.patreon.com/StrictlyAnonymousPodcast⁠⁠ 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 confess while remaining anonymous? Call the CONFESSIONS hotline at 347-420-3579. You can call 24/7. All voices are changed.  Sponsors: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://butterwellness.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Use the code “STRICTLY” at checkout for 20% off your entire order ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://vb.health⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ To get 10% off Drive AND LOAD Boost by VB Health use code: STRICTLY ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://bluechew.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Get your first month of the new Blewchew Max FREE! use code: STRICTLYANON ⁠⁠⁠⁠https://beducate.me/pd2516-anonymous⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Use code anonymous to get 50% off your yearly pass plus get a 14 day money back guarantee  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://shamelesscare.sjv.io/xLQ3Jv⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Get $10 off Shameless Care’s female viagra cream, just click on the link and use code: Strictly  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/Strictlyanonymouspodcas⁠⁠⁠⁠⁠⁠⁠⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

If you have a confession that you want to leave on my confessions hotline, you could do that. And you could do that 247. I never pick up that phone. The number is 347, 4203579. That's 347, 4203579. Make sure you're in a quiet place when you make that confession. Hold the phone up to your ear. Don't call me from your car phone.

I change all the voices on those confessions as well. Some of them make it onto a confessions episode. All the rest and all of them make it on to my Patreon. my patron, it's a great place to join. You're going to get so much. You get all my episodes early in ad free. You get Q&A's where I answer all kinds of questions every other month. You get all the anonymous picks of all of my hot female guests. You get what else access and you get access to my private discord where people get to be naughty. People used to always send me X rated stuff and I'm like, I don't touch X rated stuff on my Patreon. Everything on Patreon is R rated. But I was like,

where can I put this stuff? And it's like, where you could put is on Discord. It's a not safer work. it's locked down. It's very private. And what's great about Discord is like I said, you get to post your own stuff and talk to other like-minded people. It's a great community over there. There's tons of different channels, a lot of different things going down. A lot of times my guests go on and posts their X-rated stuff there, but also my listeners get to do it too. So if you want to post X-rated stuff or meet other X-rated like-minded people, you're going to do that through my Discord. You get all of that on my Patreon, patreon.com slash strictly anonymous podcast. Now listen, since this is a fetish Friday episode, what's great about my patron is I also have two

separate tiers. Each tier, whether it's the hoser tour or the cross-dresser's tier, it gets one extra episode a month, an exclusive episode. So the hoser tier gets one extra exclusive hoser episode and the cross-dressing tier gets one extra cross-tressing episode and the one extra hoser episode. So hoser tier is $8 a month. cross-dester $10 a month. It's very specific. You also get access to my Discord, which has a hoser and cross-dister tier as well. Okay, today I have on Jack. Jack has a super interesting story. He's a young guy, he's only 32. He's into cross-dressing. He's into hooking up with guys. He's into women. He's into prostate play. He's into caging himself, chastity play. He's into edging. He's got a super

interesting story. He talks a little bit about like, you know, when he got into cross-dressing, he was younger and then when he started to hook up with guys. And he also talks about how he got into anal action with himself and into prostate play. He did have one girlfriend where he brought up everything. And she was down and they played together while he was dressed. We talk a lot about that relationship. She pegged him. They did prostate milking together. He dressed up many times while they would get it on together. Eventually they broke up. He talks about what he's looking for now moving forward. He's very loyal guy, so he's not like seeing guys on the side when he's in a relationship with a girl, but like I said, his last relationship, he was able to do all the things that he was into with her,

and he talks all about it. He also gives some really great tips on how to start, you know, playing with your prostate. Because when you hear him explain, like, his prostate orgasms, you're going to want to try it. So anyway, I'm going to be right back on with Jack. Hey, Jack. Welcome to the Strictly Anonymous Podcast. How are you today? Pretty good.

Yourself? I'm good. So listen, Jack. You're like a guy who's into anal play and guys, right? Like pegging, prostate play, guys, all of the above. Are you also into women? Yes, women. Okay.

And all the above. Now, do you consider yourself by or do you consider yourself, you know, straight, but you're just into guys sometimes? Do you consider yourself anything? I mean, you don't have to. I would say fluid. I don't know. I don't know if I could put a label on it.

Yeah, I like fluid. I think fluid's a good term for people to use, don't you think? I mean, everyone makes fun of labels, but I actually like them. I think that they're great, especially for someone like you, when you're like, I don't fucking know, like it's fluid. It's like, you know, you go wherever, right? Yep, but it changes a little bit every day. Yeah, but let me ask you this.

Would you date a guy? Like, have you dated both men and women? I've only dated women. Okay. Would you date a guy? No, probably not, no. Right, okay. All right, so let me ask you this.

How old are you now, Jack? 32. Okay, so you're young. ever been married or are you in a relationship now? You're single now, correct? Yes, I'm single now. But were you in a long-term relationship or marriage before? Uh, that was in like a six-year thing. Just got out of that. Never been married, though. Because I know you're like, you know, you're excited to do all the things you could do now that you're single. So, yeah, the door's kind of open now, for sure. Yeah. So should I assume that when you were with your girl for six years,

you didn't do anything with guys on the side, never, no cheating or anything like that? No, no cheating everything, no. Okay, cool. So why don't we go, like, all the way back in? But, like, let me ask you this. With your girl, did you guys do pegging and prostate play and all that kind of stuff? Yes, all that. Okay.

Okay, so let's go all the way back, Jack. Like, well, let's go back to, like, when you were younger, when you figured out you might be into guys or anal play. I don't know which came first. I don't necessarily think, you know, playing with your ass makes you into guys. You know, one doesn't lead to the other. I think a lot of people think that, but that's not true. But like, what do you remember getting into first? I, trans porn is probably the first thing that comes to mind.

Mm-hmm. And did you just, like, stumble upon it or did you go looking for it? I think I stumbled upon it and something about tits and a cock and on the same person, just kind of did it for me. All, like, everything you want in one person. Exactly. Yeah. And so you saw, do you remember, like, were you very young when you saw that? Or was it?

I was pretty young, yeah. I experimented a little bit in high school, like going into my stepmom's closet when she was out, like, during the summer break and stuff like that. Doing what? Just trying, just trying on dresses or panty hose, stuff like that. What is that of all about? Are you a crossdresser too? Do you still like to dress a little bit? Yes, I like to dress.

Oh, I didn't realize that. Did you put that in your thing to me? I don't think so. I think so, but maybe not. Oh, okay. Are you a cross-dresser? Yes. So that's where we really want to.

go to, you know, if that's a big part of your story and that's, and you still dress and everything. Did your girl, a friend that you had for six years know that you were into cross-dressing? Yes. I dressed with her, yes. Oh, okay, great. Let's work ourselves up to that part of your story. Let's go chronologically and go back. So when you were younger, you remember just like going into your mom's closet. Did you, were you like, and I, of course, I'm assuming, like, even though you were really young and you don't know much, like, did you know that like, oh, I have to do this in secret? Like, I shouldn't be probably doing this, but you still did it anyway? Like, did you know what you were doing

was like super naughty or did you have no clue? Oh, for sure. I knew it was naughty. Yeah, I, it was one of those things where you got to notice everything was in the order. You got to put it back in the same order when you bring it back. Yeah, you were one of those smart people that really thinks things through, right? Just to make sure you don't get caught. Yep, you have to try to. Yeah, yeah. So now when you would try on the stuff, would you look in the mirror, would You feel like you were a girl? Did you love that experience? Like, what was it about it?

Or did you like the fabric? Like, what was it about dressing up that you were into? Like, the feel of it on my skin, and I knew that it was wrong. I'm not supposed to be wearing this stuff. Just like the excitement of all that just got me excited, I guess. Oh, part of it being naughty too is a big part of it too. Yeah, for sure. Did it change, though, the way you feel about yourself?

Like, did you feel like very feminine? when you put it on or did you feel like oh like you like you like to wear it because it made you feel like you were with a woman and you were like stepping out of yourself when when I was that young I don't I don't exactly know what I was thinking um I definitely think different now now I do feel feminine when I dress then I think it was just the excitement of doing something that I shouldn't be doing uh-huh and did you you would put on dresses panting hose would you put on the shoes too like the whole thing um Well, my stepmom was a lot smaller than me, so I would just pick, like, the big dresses and stuff that would fit me. Right.

So you like to be fancy when you were dressing up. You're picking the dresses and the panty hose. I had limited to choose from back then, but yes. Yeah. Okay. So did you ever get caught when you were, like, stealing stuff and dressing up, or were you pretty good about it? I was pretty good about it. Oh, good.

That's kind of good. And when did it turn sexual, like when you got a little bit older? Yeah. So I didn't lose my virginity until I was 18. Okay. To a man or a woman? That was to a woman. She was a prostitute. Okay. Did you seek that out? So I was in the military, so it was overseas.

Right. So it was like the kind of thing, like when in Rome? Yeah, exactly. Right. And I was still a virgin. I was 18. So I was like, it has to happen sometime. Everybody else was doing it. So I'm like, I'm doing it too. Yeah. How come it didn't happen before then? I guess I'm just a shy kid. Yeah. You're not like an aggressive guy. No, not at all. And girls, when they're younger, that age are unaggressive.

So you're the one that's going to have to make shit happen, right? The guys at that age especially. Yeah, yep. Right. So you lose your rigidity to a prostitute. When was the first time you hooked up with a guy? And like, when does the whole guy thing happen? I know you're into like trans porn and you're watching that and everything.

Do you ever watch like, did you ever start to watch like guy and guy action porn? Um, no, not then. No. It was, it was the trans porn. And I started. to learn about the prostate, the male G-spot. And I was like, well, if it feels good for other guys, I might as well try it. Yeah.

And what are you used to explore, like just your hands and stuff like? And did you wind up being able to give yourself a prostate orgasm? I started with fingers and hands just playing with my ass and my prostate when I was jerking off and stuff like that. And did it work though? Did you have a prostate orgasm? Well, I could feel my prostate swell up. Uh-huh.

I knew exactly what was happening. And back then I did not have a prostate orgasm. It was just more of a while I was jerking off, I was playing with my ass. Right. But you've had one since. Yes. Yeah. I'm a lot more experienced now, so yes.

Yeah. So you started early on because you just like read about it somewhere. Is that what you said? What's that? You said you read about it, right? Is that what you said? Like you just... Yeah.

Yeah. Yeah, I'm always... I like to learn. I like to know my body. Yeah, I'm the same way I get it right. So you're like a person that loves... into things curious. Yeah, exactly.

Okay, cool. So you, when is, so now you lose your virginity at that time. Is that when, I mean, because you're 32 and you're single, like, I mean, is this around the time when you meet this girl that you're with for six years, or do you start dating when you come back? I started dating her when I came back. Right. So you did, okay.

So while you were over there, though, was there any guy and guy action or anything or just now? When I was stationed in the States, I went on plenty of fish, and I found a cross-dresser. outside of base. Oh, that's interesting. Did you want to be dressed and see the cross-dresser, or did you want to be a guy with the cross-dresser? I was in the military, so I really couldn't have a whole bunch of clothes and sex toys and stuff like that when you have a roommate and everything like that. So it was, I was just myself in my male form going over there. I had to steal my buddy's car, not steal, but borrow my buddy's car to go off base, go over to this cross-dressers. house. And how was it? And that was the first time. It was, it was a shocking experience. It was a, the windows were open. So it was, it was very risky and dirty. But it was, it was, it was super hot. It was. But did you feel weird about it afterwards because it was so dirt? Like, was it was one of those things were like in the moment, you're like, oh, this is so fucking hot and dirty and whatever. And then post-net clarity, you're like, oh, my God, what the fuck did I do? Definitely back then for sure. Yeah. I mean, it was, it was, it was a whole. thing. He guided me on top. He came in my ass. I came on his stomach.

Oh my God. How old was this guy and how old were you? Um, man, if I had a guess 30s and I was 20, maybe 20. Did he look passable? Did he look like he was all dressed up when you got there, right? He was dressed, not passable. Right. But did it matter to you? No. I, I'm not attracted to men, I'm attracted to the male member is kind of what I'm after. You know, I just like the look of the dick. So that's what I was there for. One of the best parts about having a partner is definitely sharing everything with them, including your fantasies.

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slash strictly anon. Go there now to get 30 days of free access plus 25% off your subscription. 30s and I was 20. Did he look passable? Did he look like he was all dressed up when you got there, right? He was dressed not passable. Right.

But did it matter to you? No. I'm not attracted to men. And I'm attracted to the male member is kind of what I'm after. You know, I just like the look in the dick. So that's what I was there for. Right. But you did go after a crosshester, which is interesting.

And maybe that was like fulfilling your trans experience. Because it was like there's a, she dressed as a woman. Yeah, there was that. And it was the first person I made contact with, honestly. Oh. And yeah. What did your profile say, though? So you were obviously on plenty of fish looking for dudes.

Yes. Oh, okay. And you got hit up by a cross jester. Yeah. Yeah, you must have been like, oh, you know, I don't know. There might have been a little bit of a connection because you're a cross jester too. And you didn't have, did you have on there that you were a cross jester or no? No.

Yes, that's kind of random, don't you think? A little bit. Yeah, it kind of worked out well. But, yeah, I did have a little bit of the shame after I hooked up with them, drove back to base. I was downstairs. I passed gas. But since he came in me, all that come came out of me

and filled up my underwear. Oh my God. And it was, I had to fucking waddle myself back up to my room and took off my underwear and it was so hot, I had to jerk off again, just thinking about it.

Oh my goodness. Yeah. Okay, so that's your first experience with the guy. So now do you continue on plenty of fish? Do you continue? Or do you wind up?

meeting your girl shortly after um so i was still in the military hooked up with a couple girls the didn't hook up with another guy hooked up with that crossdresser one more time when i was in oh you did go back yes okay one other time okay did you ever dress with no because you don't have anything there right like you're saying exactly right okay so you get back and that's when you go like do you change your plenty of fish thing when you're not you know on base and you're in your regular life? After that second time, I deleted everything. I got into another relationship with a girl. That fell apart and then I got out of the military. Right. Okay. And so, but when you come back, do you like continue to look for cross-dressers and men or are you looking for women or both? Because

now you clearly know you are into both. Somehow I always find myself in relationships. And they're And they're all with women. So once I got out, I was in a four-year relationship. And nothing. It was all vanilla. I started accumulating clothes at that point, but it was all secret. Oh, okay. So everything was heading.

Where were you accumulating it? Like from Amazon, or were you going out and buying? Amazon. Yeah, small little dildos, panty hose, little dresses. And I would just keep it in like a backpack in the closet. Oh, my God. In the closet? Well, we weren't living together really.

Oh, okay, okay. Okay, that makes a difference right. Okay, so she was never going to go in there. So you had your hidden cast, she never found out. No. I brought up pegging towards the end of that relationship, and we tried it once with like a beginner trainer dildo. And that was it. And it just didn't go anywhere after that.

How did she feel about it when you brought it up to her? It was shocking. I did not bring it up in the right. circumstances and just kind of threw it on her and looking back at it it was it was not the right right way to do it right in that why you just threw i mean you're dating here four years it's towards the end of four years how did you bring it up how was it wrong i i ordered it online and i just walked out of the bedroom like hey you want to try this and it was just like no no no pre-talking no oh my i'm kind of i'm kind of into this or no oh yeah no preparation no and what and what and

And she went with it in the moment? Yeah, she was like, sure, why not? And then how come it didn't continue? Did she get freaked out? Did you not feel right about it? Like, why did it? Why did it not go anywhere? It just, it just didn't feel right.

She wasn't totally into it, and I understand looking back at it now. I should have probably talked a little bit more about it. Yeah, you probably didn't talk about it afterwards either. I mean, you finally did. I mean, listen, you did open the door to it in the wrong way, but now that you did, instead of closing the door and sweeping it under the rug, if you guys continued to talk about it, maybe she eventually could have come around, don't you think?

Yeah, but that was towards the end of the relationship. And you were breaking up anyway? Exactly. Okay, so you meet this girl, your next girl, you just wind up in one way. You're a relationship guy. You always go from one to another. It seems like that, yeah.

But after that relationship, I did go on Tinder and then I did find a guy, locally. Okay, now is this going to be the first guy, like not dressed up guy? Yes. Okay, and what was it about him that you were into? Or did you just know that you wanted to try something with a guy and just hadn't met, like, found a guy yet? Like, is that? I just, I went through that vanilla relationship and I was keeping all my cross-dressing stuff to myself and I just had this drive to suck dick so I just said screw it I'm gonna I'm gonna make this happen okay and so you went on you found a guy now are in this time at like this time that you're going out looking for people are you

going out as a cross-dressed or as a guy looking for guys a guy looking for guys okay so where do you meet this guy like in a parking lot uh we I actually just he we snapchatted for quite a few months I got comfortable with him. And he sent me his address and I went over to his house. And was he an older guy around your age? Like, what was his deal? I'd probably say 10 to 12 years older than me. But yeah, just walked.

He let me in, walked me to the couch. We sat down, had a glass of wine, started touching me up, started sucking my dick. I sucked his dick a little bit. So that was my first time doing that. that was a shock to the system a little bit. That was the first time. So the other times when you're with the crosschester, you just like bottomed?

Yes, yeah. I'm a bottom for sure. Okay. But do you like giving head too? I feel like a lot of times bottoms like giving head now. I kind of have like an oral fixation thing. So I really wanted it, but he kind of had an ED problem.

So he wasn't really getting hard. I wasn't doing it. And it was my first time. So I probably sucked at it. Oh, that's so funny. Yeah. So it's a little bit of A, B. So he had to get himself hard, and then we went from there.

Okay, and how was that experience? Because this is the first time you were with a guy. Was it any different than being with the cross dresser for you or no? Not really. I can compartmentalize, I guess. But I didn't, it didn't face me at all. And I topped him towards the end. Oh, how is that?

Are you versed, do you think? Yeah, I mean, coming from my straight relationships that I'm in, I have that dominant side of me too. So I think I'm a switch. Yeah. But yeah, I mean, he fucked me for a little bit. Flipped him over. I fucked him. I came in him and then he came on his stomach.

So it was a really good first experience with a man. Any of this time, like, because, you know, you are hooking up with guys and you're hooking with women and you are a relationship with guy. Did you ever wonder if maybe you were gay or into men in a more than a sexual way? Or was it very clear that you weren't into men any further than just hooking up with them? It's a very clean cut of, I don't want to kiss a guy. I'm not attracted to men. It's just I'm there for the dick. I'm there to get dominated.

It's a completely different, like something switches in my mind, I guess. Right. But it's only when you're in the moment. or when you're looking for it. I mean, because obviously when you're on Grindr or Tinder, wherever the fuck you are looking for dudes, you're in that headspace too, right? Because you're looking for them at that point, right?

Yep, exactly. And you know you're going to switch in. But never once did you think, oh, maybe I'm gay or into men more than this? No, not at that point until I got into my next relationship. Oh. And then I brought up, hey, so, okay, hooked up with that guy.

Yeah. Got into, this is where we're at with a six-year relationship. Okay, let's meet her. I started dating her, and I learned from my past relationship, hey, I'm not going to keep anything under the table anymore. I'm just going to come out with it. So I came out saying, hey, I'm into this. I like ass play.

I like dressing up, a little bit feminine. And it was a shock to the system. How early on do you bring that up? first couple months okay and you really like this girl you knew that she was going to be the one that's why you were like oh I gotta like put this out on the table

yeah and I just felt dirty about it just keeping it behind somebody's back and did you also tell her about the guys hooking up with guys? Yes okay so that that was where the conversation of she was asking are you gay are you sure are you trans

do you want to transition do you want to be with men am I going to be enough for you And then once she started asking those questions, I was like, okay, maybe I should take a look at myself. Am I gay? Am I all these other things? And I did have to think about it for quite a while, but no, I guess if you had to put a label on it, it would be by. But I like fluid better.

Yeah. Yeah. There's a difference. I used to think by was just so you do just like to have sex with both people, but you only like to date a member of the opposite sex. but then bisexual doesn't mean that, like, I think people would correct me. Like, no, Kathy, bisexual means you would date and have a relationship with both, not just sex, you know? So in my day, I felt like bi meant like you would just get down, you know, a little bit. But I think we had a less of an understanding of the full spectrum. There's so much, so many different things that people can be.

And that's why I happen to think that all the labels that they have out there are actually great, because they're super helpful, because everyone could find a fucking place to fit in. because there's a lot more than just like straight, gay, bye, right? Yes. Yeah. So you thought about it like that. She made you think about it, right? And then you realized you're not now.

So how was she, though, about all the stuff that you were into, you know? She was down to try it. And we, I mean, that was a very experimental relationship. In what sense? In the sense that she was down for you to like do everything with her in the bedroom? Yeah, she was just, she was up for anything. So we started, started with butt plugs, started with prostate milking. This was the first time that I actually bought larger dildos, and we pegged. And all this time, I'm dressed every single time that we play. Wow. Do you remember the first time, like,

you got dressed up and came out and, like, how she reacted? I was shaking like a leaf in my heels, but she was very positive with everything and said I looked amazing. I shaved my legs and everything so the stockings and everything feel nice on me. What's your vibe and you dress up? How do you like to dress up? I like stockings. I like garter belts, maybe like a brawlett. And then I like chokers.

Chokers around my neck is a big thing too. Oh, that's interesting. Okay, so you come out like fully dressed the first time. Yes. Uh-huh. And now, is she going to peg you that time, or are you ready to get into that too as well? It was, I have a glass wand, and I think that's where we started with it. Mm-hmm.

So you can just like focus on the prostate itself. Right. Because that's what feels the best. The prostate is a magical, magical thing. Now, listen, I know that most guys don't even use sex toys, but they should. So many guys who have called into my show talk about how stimulating their perineum, aka the male G-spot, can lead to mind-blowing multiple orgasms. And Butter Wellness has created a perineum massager that is used externally. That's right. You can stimulate your male G-spot with the

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Butterwellness.com. Use my code strictly to get 20% off your entire order. So order up. Oh, that's interesting. Okay, so you come out like fully dressed the first time. Yes. Uh-huh. And now is she going to peg you? that time? Are you ready into that too as well? It was, I have a glass wand, and I think that's where we started with it. So you can just like focus on the prostate itself. Right. Because that's what feels the best.

The prostate is a magical, magical thing. Oh, really? Yeah, I enjoy it. Do you highly recommend for even straight guys to go try it out, right? I mean, that's what I'm always saying on my butter ads? Like, what the fuck? Why not? Like, just go, like, you do have a G spot, and it is easily, like, right?

It's like easily findable. Even my butter product, I mean, you could use it on the outside and you push it in and it's going to stimulate it. You know, if you don't want to go inside, but eventually you could go inside and it's like right there, right? Yeah. It's something else. It's another level to the regular orgasm. It's something more. I don't.

It's hard to put in words. Yeah, when I jerk off, it feels good. but when I play with the prostate, like my voice changes, it gets deeper. Like, it's like this guttural. Really? Guttural feeling, yes.

Yeah, that's interesting. And when you actually have the full orgasm, like, what the fuck is that all about? Yeah, that's, that is what I think is closest to the female orgasm, just because your body starts shaking and you can come over and over again. It's once,

once you come once from it, it's the other ones are right behind. And if you, if you keep your same process up, you can, you can come 50 times a night if you wanted to do. Wow. So that first time she uses the wand on you. Yes. And now does she like realize that she like is turned on by all this stuff? Like, you know, besides doing it for you and being cool with it, is she like turned on by all this stuff that she's trying with you and seeing you dress and everything? Do you think? I think, I think, A little bit of it was just to please me. And then now looking back and the relationship's done, I think she held it over my head a little bit,

but she did play with me all the time. Oh, we'll get to her holding it over your head. I don't know what that means about I'm thinking. She would throw it in your face and fights and stuff? Yeah. Oh, God. Yeah, it's not the first time I've heard something like that. Terrible.

People are just so mean, right? Just mean. Yeah. But when we were doing it, it was good. She seemed to enjoy it. Yeah. And we would both walk out satisfied. Yeah.

So you would be dressed up. Like you could dress up in front of her. You didn't have to hide your stash. Did you guys ever talk about bringing a guy in or doing any of that stuff? Or did she ever worry about you going and hooking up a guys because she knew that you were into them? And, you know, you were just with her. Like what was going on with that whole part of yourself? with her. I think she was nervous about me hooking up with guys and then I just had to

finally to show her hey I'm loyal this is if you do this for me I'm not going to be out there looking for anything else right meaning like all that prostate play and the pegging and everything right like that's satisfying that urge in you that you wouldn't need to go find a guy exactly yeah so when she started like strapping it on pegging you was that like amazing for you that that was awesome yes Yeah, having my ass full is a pleasurable experience, and I could do it with my partner. Yeah, yeah. And would you be dressed when you did it and not dress?

Like, did you enjoy it more either way, or were you, like, equally down to do it when you were dressed and not dressed? I was down to do it either way, but dressed is just makes it that much more. There's the stockings and the choker and everything tight against my skin. and just, it makes me feel sexy already. It makes me in that feminine side of it. So that's why I, that's when I want ass play is. When you're feminine. Exactly.

And usually when we did play, I, I wouldn't come for four or five days, so I would hold it up. I would edge here and there. Oh, really? So it's just more of a desire and I want it. I need it. And right when that glass wand or, that dick would go inside of me, I would just start oozing pre-com.

So does, when you say, like, when I would, I wouldn't make me feel more feminine, that's why I wanted to be pegged, is feminine equal to you like, submissive, right? Is that what it's about? Yes, submissive. Right, being submissive. Now, did your girl get into anal play because you were so into it? Like, did she decide to try it herself? Yeah, yeah, we did end up experimenting with her a little bit, too.

And did she enjoy it? She did. She was shocked, but yes, she did enjoy it. Yeah, anyone would enjoy it if they do it properly, don't you think? Yeah, and I had a bunch of experience, so I slowed her into it, and it was definitely pleasurable. Yeah, I always say, like, if you want to, like, a guy who's never done it before or whatever, like, if you want to get your girl into it, start, like, figuring it out for yourself. Because if you know what it feels like yourself, you're going to know how to navigate it with your girl. So many girls out there hate it because some guy just shoved their dick inside of them before any foreplay or anything.

You know what I mean? And nobody could deal with that. Nobody wants that. And the only way, they think it's like a vagina. They don't understand. They think it's a pussy because they've never put anything up their ass. Like they don't get it. It doesn't just open up. Like, you know, it's not just welcoming. But you would know that if you played with yourself. You would know how to work it. There's like an art to it. And so many women, I think, don't enjoy it and aren't open to it because they had a very bad experience. Because some guy who knows nothing about it and never did it to himself, you know, try to fuck her in the end. ass in the wrong way. And that could be dangerous. Exactly. Yeah, and really hurt. So that whole time, you didn't see any guys, right? So considering, because you're loyal, like you said. Yep, yep. I was in that relationship and we played and that satisfied my urge. Right. And all your, did you guys ever live together? Yes, we did. Okay. So that was kind of nice to be living with someone not and being like out with all your stuff, not having to hide anything, don't you think? Yeah. It was. It was nice. It just wasn't as often. It was once every couple months or something like that. And I would have to keep asking for it. I would have to say, hey, let's plan this. I know planning that kind of thing sucks. But if I'm saving up for three, four days just to make that one night more pleasurable. Then you have to plan for it. Yeah, exactly. Right. Well, listen, I mean, best case scenario is she's bringing.

it up, begging you to do it and all that kind of good stuff. But worst case scenario is you have to hide all this. She's not into it, you know, at all. You know, you kind of had something in the middle where, listen, she wasn't going to bring it up and maybe she didn't think about it. And yeah, you had to be the ones to plan it and everything. But once you did, she was down and she was into it, right? Yeah. Yeah. Yeah. So, I mean, you know. Yeah, it was a, it was a give and take for sure. Yeah, of course. I mean, how could you expect somebody else to kind of know when you're horny, when you want to wait, when you want to, you know, I don't know. I think it's even given the other way around if she has something, you know,

you might not remember to fucking bring it up either. Yeah, and she has needs to. Yeah. She doesn't want to see me dressed all the time. So I would be just regular male woman sex 90% of the time. And then that other time, it's like, hey, it's my time. I want my time. Yeah.

Now, is like regular male, female? sex good for you or is it less than or do you like it it's just apples and oranges? I enjoy it. I really enjoy it. It's just there's this other half of it that you don't get with just regular vanilla sex, you know? Yeah, of course, of course. Okay, so when would she start like throwing it in your face, like during arguments and stuff in your relationship? Yeah, a little bit.

Not really until things got ended. And then she said something along the lines of, I changed my sexuality for you. What does that mean? Changed your sexuality? No, she didn't. For having, yeah. She didn't change her sexuality. She doesn't even make sense.

What do you mean she changed her sexuality? Would she think she was a lesbian when she was with you? Because you were dressed. Yeah, I think she was just upset and just wanted to hurt my feelings a little bit. Totally. I don't know what you said to her. But, you know, maybe she was. was feeling rejected on some level and then wanted to make you feel the same way. You know what I mean?

They say hurt people, hurt people, right? I mean, like, obviously she was, because I don't even know what that means. What did she even mean by that? I changed my sexuality for you, meaning I changed what I was into sexually for you. Is that what you're saying? I don't get it. I, you would have to ask her that question. But I mean, she just said that one line is what you're saying. That's it. Yeah. Well, there was a bunch of other lines. I'm the worst person ever, but it's, that, that was about the sexuality part, yeah. Right. So she was kind of like I bent over backwards for you sexually and did all this stuff for you. Were you the one that initiated the breakup?

Why did you guys break up? It was an on again, off again type of thing for quite a few years. It needed the end, but she ended it on the last one. Okay, so it was only she was resentful, but you're ending. Okay, so now you're single. How long have you been single for? A few months now. Oh, okay. Now have you.

started meeting guys and doing stuff like what's been going on now i haven't been doing anything i just been keeping myself um but that urge is there and i want to start uh experiment with stuff how do you keep both sides of you like in line like do you like you know because you're a relationship guy so most likely you're going to wind up in a relationship again do you think like you're the like how do your cycles go like you'll go out and like hook up with a bunch of guys and do that thing and then start looking for a girl will you work both? sides of you at the same time looking for guys looking for another girlfriend at the same time like how does it work i don't know but since i am a relationship guy i think i just want to be single for a little

bit i'm i'm 32 i'm in the best shape of my life this is my prime so i think i just want to ride this out for a little bit and see where it goes do you miss being with guys or cross-gesters when you are in that and your relationship like when you're with that girl for six years did you Jones for it. Did you wish you could go out and do it? Or was it because you were doing everything at home like you didn't, it wasn't, you didn't even think about it, have to think about it. No, you still want it. I still wanted a real cock. I wanted that feeling, you know, you don't, you don't get everything because the strap on doesn't, they don't know how to move it exactly because it's not attached to them. They don't feel it. And it's not a real dick. There's a big

difference. Yeah. Yeah, definitely. Right. But you're still dressing? Did you move out of the apartment? You have your own place now. Like, you still have, like, all your stuff you're dressing. Are you on any apps, like, looking for guys? I just downloaded SDC earlier this week. Oh, did you use my free code?

377.12. No, I'm really serious. I could offer. I have a free code. And I pick them because people always say that that's the best one. And I do have a free trial so you could check it out, you know, for a couple days. Yeah, I did the free trial. You couldn't like click on a bunch of profiles and stuff like that.

You couldn't, if you weren't. Can you click on any profiles? You could click on some, but some of them had a, had a blocker up if you're a free trial member. Oh, that makes sense. They don't want just looky lose. Yeah. Uh-huh. Yeah.

So I ended up buying the membership, and this has only been two days that I've been on there. And I have a few matches and a couple people that I'm talking to right now. Oh, I love that. And now what are you, like, who are you on there? Are you a cross-gester looking for their cross-testers? Are you a guy looking for a guy? Are you a guy that sometimes cross-dresses that's into guys too? You know, like, how do you identify in there?

What's your profile looking for? So I put bisexual just because I want both sides of it. Yeah. And I have a very detailed bio saying, hey, I do like to dress. I'm submissive. I love that. I think that's important to be as detailed as possible. Yeah.

I want to be submissive bottomed and give head when I'm dressed, but that's not necessary. Yeah. I can fit multiple different people's needs. Yeah. For sure. Yeah, I guess I have both pictures. I have male foreman, me dressed up. Oh, wow.

That's perfect. And you probably got hit up by a lot of guys now because there are a lot of guys. Okay, I have cross-dresses on my show. There's a lot of guys, married, straight guys. out there that, you know, it's on the DL, you know, I'm sure maybe younger ones aren't, but a lot of guys that will go out and, you know, looking for a cross-dresser, right? Did you get a hookup? Yeah.

Yeah. Yeah, I think, I think this app is more designed for couples. Yeah. That want to swing. So that single men aren't as wanted. I don't know. Maybe I need a download grinder and put a pro-exam. file up there too i don't know yeah why not work both but you already had hits over there on

sDC and from like who uh so there's nobody really close to me everything's kind of like four hours away oh which which which which which which which i'm down to make a weekend out of something yeah it's the right thing it comes about right yeah yeah yeah but who's kind of hitting you up couples got other single guys uh one single guy and then a couple couples right this one couple just just hit me up last night saying she wants to be the dom to her husband and me and that's kind of interesting yeah definitely a different dynamic for sure that's going to be something new and obviously something you're open to right yes yeah i i think i think that's the best case scenario of going in with a couple with a little bit more experience in this lifestyle because i'm new to it i'm

been in just relationships and just hooked up with a couple guys and that's it. Yeah. So ideally I want to hook up with a couple. They can show me the ropes and I don't know, honestly just be used by a couple to whatever their needs fit. Oh, so then that's perfect. Yeah, maybe try Grindr to do some like, you know, solo hookups. But then SDC is kind of perfect if you are looking for couples, right?

Because there's probably a lot of couples on there. And look, the fact that you've only been on there for such a short time and already have a couple couples, they're ready. I mean, that's pretty good, right? That only means that there'll be more. Yeah, there's more, but I do get the vibe of people don't want to deal with the long distance, which I totally understand. I don't live in a big city.

If I lived in a big city, maybe I would have more options. Yeah. Well, I'm sure there's guys, like I said, if you turn on Grindr, I'm sure there's guys three blocks over that I want you to suck your dick if you put yourself up there. You know what I'm saying? I'm sorry, but there's just a lot of guys that are into that. I have them all calling into my show. Yeah, I get that, but I also do have a fear of STDs and everything like that.

So I just want to, I don't want my horniness to overpower my decision making. Well, I think that that's smart. And have you always been really safe and always been able to, you know, live by that motto of yours? For the most part, yeah. I mean, some drunk nights, you make some mistakes. But for the, for the most part, I try to make good decisions. Well, you do know, and someone's going to say this in the comment section, well, you know, he could get an STI. And I learned this recently. Like, you can get gonorrhea in your throat. Do you know that? Yeah. So I have an oral fixation thing, so I don't have a dick to suck on. So I have dildos here.

Yeah. Apparently, you can't deep throat when you have tonsils. Oh, really? That can't be true. Well, I did that, and I had the worst throat infection I've ever had. I was sick for a couple weeks. Wait a second. It wasn't with a real guy's dick, right? So you obviously didn't have anything, any kind of STI going. But you used a toy. You deep-throated a toy and got an infection? I, they think it was like along the lines of a strap or something like that, yeah. Okay, let me just ask you a gross question that, you know, I don't know. Like, you don't, you don't, you don't, you don't, you don't, you don't, you don't, you don't, you don't, you don't, you don't, you don't, you don't, you don't like, you don't. type of guy that's probably overly clean too.

I don't know. But like, you know, was that thing, that toy that you used maybe in your ass like to seven days prior, maybe a month prior and you forgot and maybe it wasn't totally washed properly and, you know, some of that bacteria got in your throat? Because like, how can you get, you know, an issue by sticking a clean toy down your throat? It was a new toy. It's never been inside me. Okay.

So that's good. Okay. So it was brand new. It was a large toy. and I think I was just a little rough on my throat. Oh, my God. And is that something, was that the first time you got to deep throat or were you always able to deep throat? That was the first time because I like the gaggingness.

Like, I like chastity play too. So if I'm locked up in my chastity cage, I want to suck dick. So it's fine in my mouth, but once it goes down the back of my throat, it hits like that vexative. guess nerve and it just it just clenches everything up and within minutes I'll just my cock will just be dripping out pre-cum it's it's just super hot oh so there's some nerve in your throat that you're saying that you hit and it like adds a turn on for you yeah I mean I can't deep throat I'm very impressed with people that can did you obviously taught yourself how to did you teach yourself with toys yes with toys how just relaxing and breathing and getting comfortable with

that the back of your throat. Did you stick your head backwards like that? Did you do that move in the beginning to make your throat straight? No. I, so I'm very 420 friendly, so I get a little relaxed. Yeah, very relaxed. And then with my cock locked up, I just, I just get super horny and I just pretend there's somebody in front of me. And I want the back of my throat touched. Right. And now, because you're obviously shoving that huge thing down your throat, did you eventually, over time, because you got bigger, bigger dildos in your ass and stuff, turned into a size guy?

Like, do you like bigger dicks? Is that a thing for you? Yes. Obviously, visually, it's appealing, but even inside me, I want something. That fills you out. Yes. Yeah.

And obviously, the bigger the dick, it's more likely to rub against my prostate and make everything feel good inside of there, too. Yeah. And so you just kept buying bigger and bigger dildos, right? Is that how you got into the bigger sizes yourself just like going there? Yeah, because I, so that cross-dresser that I hooked up with, he put this massive, massive dildo inside of me. Like how wide across, do you think?

Two inches. Oh, my gosh. It was a, it was a very large. Uh-huh. And ever since that, I'm like, I know I can take. dick well. So it's always, yeah, let's get a decent size one. I don't want to mess around with the little trainer dildos. And how did you get that big thick, like, so you one day, the time, like, I'm going back to your infection that you got, like you literally shoved this huge thing down your

throat aggressively and it was like one of the really big ones? Yeah, I mean, it's like an inch and a half diameter, eight inches long. So it's a, it's a decent size. And I think, I did it two nights in a row. So I think it was sore and aggravated for the night before. But, but that's, that's, that's what I like to, I like to edge. I like to make my orgasm that much more when it does happen. So I sucked my dildo the night before, got to the edge a couple times.

And then I was playing the next night. And then I think that's when I, mess my throat up. So wait, so then what happened? So like the next day your throat is like hurting, you're like, what the fuck? And then it just like didn't go away. And you had to go to the doctor? Well, I woke up and it was a little sore.

And I'm like, okay, that's understandable because I just had this massive cock down my throat. Yeah. And then throughout the day I drank some tea, had some lozenges. And then nighttime smoked a little bit. And I was like, well, I'm going to do it again. And I pushed. Again the third time. It was, it was sore and I pushed past it.

Oh, yay, yay, okay. It was just a bad decision. And then you got really sick? Yes. Yeah, I had to go on to antibiotics and everything and it took like three, four weeks to get over it. You didn't cop to the reason why you had this with your doctor, did you? I did not. Were they, like, looking at you funny?

Like, they kind of knew? I don't know. Like, you know, because, like, they say that if you go to the dentist, but I think it's like they see the come or something. Like, they could see whether you had it. you gave a blow job recently for somehow. I don't know how, you know. I'm like, I wonder if they kind of knew. Because, you know, they see all,

you're not the first guy that probably got a throat infection from deep throating a dildo. Though it's not common, I don't think. I don't think it's too common, but they did not look at me weird. They just said it's most likely strep and here's some drugs for you. Wow, that's so interesting. Yeah, you like, you know, give your throat a fucking break. It's a little crazy. Yeah.

haven't done it since, so I was just nervous to... Push it, yeah. Irritate anything again. Yeah, well, you pushed the envelope a little bit too much. What would you say, like, you talked about prostate milking. Like, what is that all about? What's the difference between prostate play, prostate milking? What does that mean?

I think it's the same thing, but you're just more focused just on the prostate itself. Right, working it, like specifically. Yeah, I have a little curved glass wand. and it just it just hits that spot perfectly. Right. So you're just going up against that back wall, moving back and forth on that prostate. And when I like to play with my ass, I don't like to touch my dick. I think it's two separate things.

You can have an orgasm when you're touching your dick and then you can have an ass orgasm. Oh, so you don't even need to. Like when you're doing the prostate thing, you don't even need. Like you're orgasming without touching your. your dick. Yeah, and even when I'm with a partner, I don't want them to touch my dick. Yeah. Focus on my prostate because I can come this way and I can play for an hour.

And usually play is over when I have an orgasm when I'm jerking off. So I can have 20 prostate orgasms. And then I have one when I'm touching my dick. And then play. And then it's over. Oh, but it's not over when you have. prostate without touching your dick. No, that can

go on for hours. Yeah, I mean, like, listen, you should be like the poster boy ad for, play with your fucking prostate. I mean, you know, it's like kind of hands free. Like, you know, no touch your dick, you can have all these orgasms and you can just keep going. You don't even need to be jerking off.

You know, do me a favor. Send me a picture, or like, send me a link or do you have it to the want, people are going to want to know. I always recommend this metal one that somebody actually recommended to me. Because she learned how to squirt for men and it turned out that, you know, I found it on Amazon as a prostate massager for men, you know, it's a metal one. That one, the metal one,

I'm like, whenever I talk about it, I sell so many because I could see on the link, you know, I make like one penny each one, but like the guy who's selling it or whoever is must be like, what the fuck is going? Like, well, how come I have all these sales all of a sudden? You know, But it's the same kind of thing. There's a metal one, a glass one. I mean, would you recommend that as, like, the best way to start off, like, using to stimulate your prostate? Besides my butter thing, I mean, that's good to use on the outside and you press it in and, you know, for guys that are afraid to go inside. You know, and that's why I like to promote the butter because I feel like it's a good starter thing.

But if you're going inside, did you recommend that one? Is that your favorite thing to go inside with? That's my favorite thing. But if I was talking to somebody that was just getting into it, I would probably say, start with a butt plug kit small medium large start start just waking those muscles up down there and then upgrade you like a vibrating butt plug or a vibrating prostate massager right and if that does it for you you can go to a small wand or start getting into strap-ons and dildos and stuff yeah so that would be i like that i like i think that's really good advice like that's how you would start as a beginner

The beginner prostate kit. Yeah. I mean, if you're popping butt plugs in, I mean, you could have sex with your girl, pop a butt plug in. And if it doesn't amplify it, then I don't know if this is the road to go down. Or do it yourself. Listen, I just went sex toy shopping the other day because somebody brought something up. And, you know, I went looking for butt plugs. Oh, it's because me and my guy, he was, you know, I did a whole pussy pick contest on my channel.

And he was raiding the pussy pics with me. and he a lot of girls had butt plugs with like rhinestones or some shit on them you know and he was like oh what's that you know whatever and i'm like i'm gonna go get some of those butt plugs it'll be funny when he sees me and with one but they come in like three sizes like that's what i want to cop to i bought one and it was like small medium large so like when you say get that like that's how they that's how they sell them right small medium and large yep exactly and i i have that exact one with the crystal rhinos yeah yeah yeah a lot of girls had that i didn't think there's anything wrong with it. He's like, oh, they're hiding. They're badass with that or something. I'm like, I don't think so. I'm like, but I liked Budplugs. I haven't, I haven't played with them in a really long time. I'm like, oh, I'm going to, you know, it reminded me. I'm like, I'm going to get that. I like toys. I think it's always fun to play, you know, so I got it, but I was like, oh, you know, when you were talking about small, medium and large, I'm like, when I was on Amazon looking, they were all like small, medium and large. Like, that's how they, that's how they

come, and they're super inexpensive and a great place to start. And then also, uh, if you, you don't want to go inside for regular guys. I want to keep trying to try the butter. That's always a link in my description. But listen, good luck in your future. Hopefully you'll find a girl that, you know, I mean, I would hope that moving forward, I would assume that, you know, any girl in your meet, you're going to do the same thing like you did with the last girl and put it all out on the table in the beginning.

Yeah, I think that's the smartest play. And then, yeah, go from there. Yeah. Listen, you're younger. There's so many younger girls out there are so much more open-minded. And I, you know, I have so many guys who call them to my show. that are with women that accept all of it and are cool with it and love it. So wait for that girl.

There's no reason to settle for anything less. But anyway, thanks so much, Jack, for calling in and sharing your story. I feel like you're going to sell a lot of butt plugs today and wands. Good deal. Thanks for having me. Yeah, no. Thanks for calling it. And I'll send you, if you want to send a pictures for like the crossdressing tier,

like, you know, if you crossdressed if you want for my Patreon. And I'll give you free access to my Patreon to see the comments for the first month as well as free access to my discord. Okay, perfect. I'll sign that to you. All right. Awesome. Thanks for calling in Jack.

All right. Thank you. Bye. Okay. Good news. I do have a book out. I wrote a book and it's coming out. The book is called Tricklead on Miss Confessions.

Secret Sex Lives of Total Strangers. What I did was I picked out the 17 best episodes. That was very hard to do. Okay. I picked like one from each category. And I retold the story from the third person. So it's not interview style. It's a little bit more erotica.

The only place where I took creative liberty was in the sex scene. So it's even hotter than my episodes. Like I said, it's told in the third person. And they're all true, just like my show. I mean, these are real stories from my show, just written out. Like I said, in the third person, not an interview style, more like a story. But a true story, a true super hot story. Now, listen, it is available for pre-order now.

And it's not coming out until October 14th. And I was like, oh my God, that's a long time away. So I figured I'd incentivize people. If you want to pre-order it now, I will give you free access to my Discord if you pre-order it now. All you got to do is screenshot, a pick of the receipt. Just screenshot it to me. Send it to Strictly Anonymous Podcast at gmail.com. And then I will send you the link to my Discord.

So that's a little incentive to pick it up now. It's on Amazon, Barnes & Noble, Simon & Schuster. the link is in the description, so make sure to click on it. And if you get it, send me the pick of you purchasing and I'll give you free access to my private discord that is a totally naughty, super hot community with a lot of people over 200 people over there having fun. Remember email me the pick at strictly anonymous podcast at gmail.com. 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 e-book, but you can pre-order the audiobook. 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-bang girl story. Like I said, 17 stories. And they're all told in the third. 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 ebackform. format, paperback format, and finally, the audio book 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 can 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. This is the strictly anonymous podcast.