Strictly Anonymous Confessions - 1331 - Sissy is into Men, Dressing up and Being Sissified

Episode Date: January 9, 2026

Sissy is into dressing up and being sissified and he called in to talk all about it. Tune in to hear all the details including when he started hooking up with his male high school friend and how he felt about it at first, when the whole being a sissy and dressing up started for him, what he started wearing first and how progressed, when he got caught hooking up with his guy friend while dressed up when he was younger, when he started fully dressing up and why he didnt tell his girlfriend, when he got caught hooking up with his guy friend by his current girlfriend and how that led her into sissifing him, when she started buying him toys and using them on him whole he was with his guy friend and what exactly would go down, why the relationship with his girlfriend ended plus a whole lot more. To see anonymous a pics of my 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 GET A COPY OF THE STRICTLY ANONYMOUS BOOK! Strictly Anonymous Confessions: Secret Sex Lives of Total Strangers. A bunch of short, super sexy, TRUE stories. GET YOUR COPY HERE: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠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." Want to confess while remaining anonymous? Call the CONFESSIONS hotline at 347-420-3579. All voices are changed.   Sponsors: ⁠⁠⁠⁠⁠https://vb.health⁠⁠⁠⁠⁠⁠⁠ — To get 10% off DRIVE Boost by VB Health use code: STRICTLY ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.quince.com/strictlyanon⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ — For premium quality Quince clothing plus FREE shipping and 365 day returns! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://butterwellness.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ — Use the code STRICTLY at checkout for 20% OFF your entire order⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://beducate.me/pd2540-anonymous⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠— Click here to take the quiz and  get your personalized roadmap to sexual happiness ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://bluechew.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ — Get 10% OFF your first month of Bluechew GOLD! Use code: STRICTLYANON⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://motorbunny.com/strictly⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ — Click to get $50 off! Follow me! Instagram  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.instagram.com/strictanonymous/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ X  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠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

to the Strictly Anonymous podcast. Conversations with online strangers. We place ads online. Craigslist is definitely the gift that keeps on giving. Real people respond. You could sing a bore with Thailand. You can't not do it. The temptation is just too much.

Real problem. Does your friend know that you're banging her? No, he has no idea. And anything goes. Motto of the show, let your Greek black fly. Probably the only good advice I'll ever give you is to re-hide your whips and chain. Here is your host, Kathy. Hey, welcome to the strictly anonymous podcast with Kathy.

If you want to be on the, if you want to follow the strictly anonymous podcast on either Instagram or Twitter, follow the show at Strict Anonymous. If you want to be on the show, it's called Strictly Anonymous because I do change everybody's voices. Now, you could email me from a phony email. I don't even need to know who you really are. I just want to hear your true naughty story. So if you have a true naughty story that you want to tell on my show, all you got to do is email me at Strictly Anonymous Podcast at gmail.com or go to my website strictly anonymous podcast.com

and click on beyond the show. Now, if you have a naughty confession that you want to leave, you could call my confessions hotline anytime. That's the number is 347, 4203579. That's 347, 4203579. You could call that number anytime. Just call when you're in a quiet place. Okay. Some of those confessions will make it onto a confessions episode. The rest all go on to my Patreon. Now my Patreon is super great, especially for guys who have like either a pantyos or a cross-dressing fetish because I do have a hoser tier. I call guys who are into Pannejo's hosers and I have a cross-dressing tier. Now, both of those tiers get every single episode on my show early, ad-free and intro-free. You guys also get all of the picks of all of my guests. Plus, you get exclusive

extra content hoser and cross-dressing episodes that can be heard nowhere. else except on my Patreon. I give each tier one free episode a month and you have access to all the ones I've put up there previously. So there's tons of, like I said, exclusive hoser and cross-dressing episodes over on my Patreon. And you'll also get a free complimentary link to my Discord, which has a hoser and cross-dressing channel. There's lots of channels in there. You can meet people, like-minded people. It's a great place. It's not safe for work. It's locked down. But you can get in there. if you join my Patreon, the cross-dressing tier is $10. You get the hoser episodes and the cross-dressing episodes as well as everything else.

And the hoser tier is $8 a month. Now, listen, you could also get access to my Discord by buying my book. I have a new book out. It's called Strictly anonymous confession, secret sex lives of total strangers. There's fetish stories in there, hot wife stories, cuck stories. You name it. I got a story in there. 17 hot stories all written in the third person taken from my show.

That book is available anywhere you buy books. I will put the link in the description. And if you buy the book and send me a screenshot of your receipt of purchase, I will also give you complimentary access to my private discord. All of the links to everything that I talked about are in the description. But anyway, today I have on Sissy. Oh my God, Sissy's got a really interesting story. story. I was like mesmerized by cissy's no voice. I mean, he was made to be a cissy. He doesn't really speak

up for himself. Like when he was younger, he started like hook it up with his guy friend and he started blowing him and the guy never blew him back. And then he got into like dressing up when he was with this guy. I mean, the whole scenario with his best friend is like super interesting. And it started when they were like, you know, in high school and continued on to this day. And like I said, it went from like BJs to him dressing up in panties to cheerleading up. And, and you name it, he started wearing it. He talks about that whole story. And then he started dating a girl.

And he was with his girl for a long time. And he talked, you know, he was still seeing his guy friend. And she eventually wound up catching him. And he didn't get caught when he was younger, too. Wait until you hear the story about him and his friend getting caught when they were younger. But he got caught by his girlfriend when he was older. And after that, she really, like, humiliated him, got him to dress up, use toys on him for the next year that they were dating.

And he talks all about that. It's a super interesting story. he's currently single looking for someone to dominate him because he was like into it he's into humiliation he's into dressing up he's into being cisified and and he sent me in picks of him dressed up i have him over on my patreon my patreon my patron's a great deal so sign up for my patreon if you want the link is to that is in the description but anyway i'm going to get right to be right back on with sissy this is the strictly anonymous podcast oh hey cissy welcome to the strictly anonymous podcast How are you today?

I'm doing good. You're doing good. So listen, sissy. You are a sissy. You have like two things going on. And I don't know. I think maybe one has something to do with the other. You did say your girlfriend had a lot to do with you, like, you scissifying you.

You did, you do blow your best friend on the DL and there's a story there with your girlfriend. I don't know how long that's been going on. Which came first, blowing your friend or, you know, cross-dressing or being a sissy? A blow job Give him my best friend blow jobs Oh my God Nobody knows This is like on the DL you did to present

As like straight dudes walking around Yeah we used to watch porn together And then one day He just kind of like coerced me into doing it How did he coerce you? Well he came out of the shower And took off his towel And I was laying on the bed

And he just put it in my face And so I just started sucking it How old were you? Like in your teenagers? Let's see. I was in 19th grade. Okay. So like, you know, you're kind of grown up. Not grown up, but like, I don't know, you know, people are starting to hook up with people. You just, instead of hooking up with a girl, you start of hooking up with your friend. Yeah. Okay. Now, I mean, he didn't force you to, right? Like, I mean, you were down?

Yeah. Yeah. I mean, at first I was kind of hesitant. And then I just decided I wanted to do it and try it. And then after that, it just became like a normal thing. Now, did you get weirded out? Because this is like your best friend. Do you know what I mean? It was kind of weird at first. You know, I was kind of embarrassed and stuff. But like the more I did it, the more it just became just a normal thing.

And then you like, you would do that on the DL and then go back to school and be buddies in front of everyone and no one would have any idea. Isn't that interesting? I bet you that's more common than people think. Don't you think? Yeah, I do. Well, because you were doing it, but I mean, I just think a lot of guys lined up, you know, because they're so horny at that young age and they can't get chicks. So they're just like, you know, their friend does it for them. Do you know what your friend's doing now?

Are you still best friends with him? Yeah. Still best friends to this day. Still blowing him? Yes. Now, is he in a relationship with a girl? He is. Is he married?

Is he single? I mean, is he dating? Well, I mean, he's been with the girl that he's with for a very long time since. probably high school since like 12th grade. Okay, does that girl know about you guys giving each other head? Well, he doesn't give me head. I just give him head. Oh, that's kind of interesting.

Yeah, and it's always been that way. You know what I mean? So. No, I don't know what you mean. I want to ask more questions. But I mean, listen, I know that they're like in this like guy on guy, I want to fucking blow you situation. There is definitely the guy that wants to blow the guy and the guy that wants to get

blown. and a lot of times that guy doesn't do the opposite. Do you know what I mean? And trust me, there's a lot of guys that want to suck a guy's dick, right? And they don't want anything in return. I always kind of say, like, to straight guys out there. Like, if you want a blowjob, there's like so many guys out there that have this, like, weird kink where they're not really into guys. They don't even consider themselves by, but they like to suck a dick sometimes.

You know what I mean? And that's all. They don't even want a guy to suck their dick. Like, did you ever want him to do it back and he just wouldn't reciprocate? at times sometimes I would but like yeah it was just there was no he never did it to me so and you never spoke up for yourself and said hey fucking blow me now like you never asked for I mean I don't understand people that can't talk I mean because I'm like the opposite of you I would be like hey it's my turn like go fucking go down on me you know what I mean but like so

many people can't speak up for themselves so for you you kind of wanted him to but you just didn't have the balls to say hey dude now it's my turn Yeah, kind of like that. I'm like, I was real submissive to him. So, oh yeah, that probably helps the sissy in you, right? That's probably a part of the turn on, right? Yeah, I'm ruining your sissy vibe. That's like I always forget. That's what it's about. You like to be denied. Yeah, I do. And, you know, like on edge all the time. So yeah, I used to put on his, his stepsisters panties and then watch porn and give him blow jobs too. So that's kind of like how the whole sissy thing started. Yeah, but let me ask you this. Before him, right, before like putting on panties at his place, did you ever do any kind of feminine clothing trying on shit at your house before him or no? No, no. Okay. So this all starts. So now was there blowjobs and then the panties or did the panties coincide with the blowjobs in the beginning? No, it came later on. Did he say, hey, put on my sister's panties? Yeah, he was kind of the one who suggested it.

So you're being cystified by people all your life, not just your girlfriend, this guy too. Yeah, yeah. I just didn't know it at the time. Yeah, but you're listening to him and he says, hey, now let's like add this into the mix and you start wearing panties. What kind of porn did you guys watch? Like a girl, like heteropor porn or gay porn? Well, we found his dad's porn collection and it consisted of mainly just girls giving guys blowjob. so yeah that's why you guys were just blowing he was to use getting blow jobs from you right oh my god

can you believe what goes down did you guys ever get caught besides your girlfriend because i know she winds up finding out but like did you guys ever get caught by anyone else yeah his step-sister had had walked in on us one time and i had her panties on at the time like i got caught so no offense but i would have loved to been that step-sister i would have been like what the fuck is he what did she What did she say? What was her reaction? Well, she kind of called me to her room and talked to me about it, told me that she wouldn't tell anybody. And then kind of like just kind of like hinted at like she didn't mind like me barring her things.

Because I mean, she was hardly ever home. So yeah, so she kind of just said, yeah, you know what I mean? You can use whatever. So that's like when the cheerleader outfit kind of came into play too. But wait a second. So did she see you blow in her brother or she just saw you wearing the panties? No, I was on my knees in her panties giving him a blowjob when she walked in. And the only thing she referenced when she pulled you into the other room is the fact that you could just continue to wear her clothes.

Nothing about the blue coat of? Yeah. Yeah. And then she wouldn't tell anybody. She kind of like gave me assurance that she wouldn't tell anybody that it was okay. Did you say like what the fuck's going on in here? Was she surprised at all? Not really. I mean, she was always getting high all the time.

So like, you know, I mean, like, yeah. Maybe she was so stoned. She didn't understand what was going on because I would assume someone would give some sort of interesting reaction. I mean, she was just like, oh, it's okay. You know, like she just leaves. She literally catches her stepbrother and his best friend blowing him in her panties. And she's just like, oh, okay.

No, no weird surprise face. I mean, she did laugh. She did laugh. So that made it really. embarrassing for me. Oh, but that, but you know, you start to get wired into that maybe. Yeah, yeah. It was kind of a turn on too at the time. Hey guys, why not start the new year off the right way with better orgasms and way bigger loads that also taste better. That's right. There is a supplement that is doctor formulated that will not only increase your loads. It will make your jizz taste better. Okay. And

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Their latest formula also includes an enzyme called bromoline that makes your semen taste better. Okay? Maybe you could get your girl to finally swallow it once you start taking load boost. And the good news is, load boost works super fast. Some people see results in just days of taking it with most people seeing full results after just two to three weeks of daily use. That's not too long to commit to bigger and better tasting jizz. Now listen, all you got to do to get VB health is visit loadboose.com and if you use my code strictly, you're going to get 10% off or just go to the description and click on the link. That's loadboose.com. Use my code strictly for 10% off or just go to the description and click on the link. No, no weird surprise face. I mean, she did laugh. She did

laugh. So that made it really embarrassing for me. Oh, but that, but you know, you start to get wired into that maybe. Yeah, yeah. It was kind of have a turn on too at the time. The humiliation of her laughing at you. Yeah, that's what I would expect. I would expect there would be some sort of reaction like, oh my God, or laughing or whatever, because that's not a normal thing to walk in on when you're young, especially. Okay, so she says I wouldn't, whatever. So you continue on. Do you start to wear more than the panties with him? Then you started with a cheerleading outfit is what you're saying? Yeah, yeah. So like, I went to the back of her closet and then found her like high school cheerleading outfit. So I started using that. And, I started using that. as in role play when I would give them blow jobs and stuff and kind of imitate what the girls were doing in the porn porn. Wow. Okay. Yeah.

And how would you get off on these scenarios? Would you just like to be denied and then you'd go home and jerk off about it? Yeah, yeah. I would just like rub myself while I was doing it. Right. You know? Yeah. Did you ever question your sexuality like in the midst of all this?

Because you know, you're like super young. Here you are blowing a guy like maybe you're gay. Maybe you're by. Like, what do you start, like, what do you figure out about yourself? Well, I mean, I was still into girls. I had a girlfriend at the time. So, like, it was like, kind of like going back and forth in my buy or am I gay. Yeah.

What did you come to any conclusion? Not at that time. No, but now today, I would, I mean, I, I like to identify as sissy, you know. Okay. What does that mean? Just being girly, dressing up girly, being submissive. being feminized. But do you feel like, let me ask you this.

Because I think it's like a little bit more confusing when someone has like a cissy side or a cross dressing side. Because sometimes like when they're in that form of themselves or just expressing themselves in that way, maybe they want to suck a dick or something. But when they're not, you know, which is more of the time, they're not interested in guys at all. So like, are you one of those? Are you interested in sucking dick whether you're dressed or not?

No, I'd rather be dressed girly. when I'm doing it. Do you find yourself attracted to men when you're not girly in your girly mode? No. That's where it gets like kind of confusing and why it's hard to sort of identify with anything because it's not like you're always in sissy mode, but when you are, you want to be with a man. Interesting. Have you ever hooked up with, I'm still going to go back to the chronological order,

but have you ever hooked up with any other guys besides your friend? There was another friend of mine for a long time. for about three. He was a friend of mine for like three years and I was doing I was giving him blow jobs as well. How did that come about? Did you instigate that one? I did. We, we drank together and I kind of just like suggested that I wanted to do that to him and kind of like gave him some insight of like what I was into. And he was okay with that. So like him. Yeah. I mean, this is another young guy.

what age are you guys probably like 20 we're definitely like at drinking age so it was like 21 22 somewhere around there okay so he's like yeah why not I'll try it yeah listen I think a lot more people are like open that way especially guys

I don't know then they cop too there's still such a stigma surrounding guy and guy action that I think a lot of guys you know would be like oh my god I would never but like I think a lot of guys if they're like fucking horny and the wind blows the right way. And some guys like, hey, you want a fucking good blow job, though.

But like, okay. I mean. Yeah, yeah. So that's not a big deal. Yeah, I don't know. So he, so you sucked his dick for many, for many years? For about three years. Yeah, until he left and went off on work, some job.

And then we haven't had contact since. Okay. So now let me ask you this, because you're dressing up when you're with that guy. Do you start to like dress up on, on your own as well? I do. Like when I'm when when when I'm at home by myself, I like to dress up like, you know, put on lingerie, you know, thigh highs, garter belts, baby dolls, bras, you know, boob inserts, you know, like fake boobs. Do like my wigs and like pigtails and ribbons and bows. You do the whole shebang. Yeah, I go all out. Did you start doing that with your friend or did that, did you start just doing that on your round? No, no, no, I started doing that with my friend.

So the more like as years progressed, the more and more I just kept, you know, like getting into it. Becoming more of a girl. Like, so you were like full-fledged makeup, wig, everything from head to toe. That was about the time like where I got caught by my ex-girlfriend. Do you have a girlfriend now? I don't, not at the moment. Okay, okay. So but that girlfriend, you blamed her for sissifying you for some reason.

but it sounds like you're Cissified way before you ever meet her. Yeah, yeah. I mean, she had a big role to play in it, like to like, I guess like push me in that whole direction. So it doesn't sound like she needs. You already fully there. Okay. You're dressing up.

I had to toe as a chick, blowing your friend in a cheerleading outfit. Let's get in. I don't know why you think she has anything to do with it. Let's get to the, like so I'm assuming you meet her when you're young. How, when do you start dating her? Like let's get to the point. where you meet her in the story. About 18.

About 18. Okay, cool. So you meet her at 18 and you start dating her now. Do you ever tell her about your guy thing and you're dressing up? No, never told her until, you know, the day that I got caught. So now how did you get caught by her, correct? How long were you guys dating at the time? We're together for about eight years at that time when I got caught.

Wait a second. So 18, you meet her at 18. You're 26 years old and you're still blowing this friend through the whole. relationship for her through her your whole relationship with her you're cheating on her with your guy friend yes and dressing up in full-fledged leading us a double life yeah but we would have to meet you know in secret when when we would do that so course well that's the whole point of a double life you're not meeting in public okay so how to oh my god so you're dating her for a long time how does she find out like tell me that's the moment you got caught what was going down okay so

we were in the backyard, we were smoking, and the way that the house is set up, it's like, you know, like, you can, I could see the back door. So I guess she went from the front, she went out the front door and came around the block and up the alley to like where the back driveway was. And just, he had his pants down to his knees and I had my head in his lap and she knocked on the window. So it was really like no denying it. Well, wait, but instead of like. I don't understand.

Was she at the house already or was she not at the house? Yeah, she was in the house. So I was taking a big risk of getting caught. Oh, my God. So you know for a fact your girlfriend's in the house and did you do that often, like, blow your friend like literally when she's in the next room through this whole eight years? Not so much, but this night, I just, I don't know. It just happened. When you say you were smoking, were you smoking weed?

Yeah, smoking weed. Yeah, see, you just weren't in the right headspace. So she somehow sees you guys through the window. I mean, it's not that hard. Right. Yes. Does she see you dressed up? You're not dressed up.

No, I'm not dressed up at this point. Okay, so you blow him even when you're not dressed, this guy. So what does she say? Well, I mean, she knocked on the window and he rolled the window down and she was kind of like, don't stop now that I'm here, you know? So like she just watched me finish him. And we went in the house and we took. talked about it and I told her everything from the beginning.

And, okay, she wasn't flipped. I don't understand people in your life. What fucking country or a planet do you live on that? Nobody has any kind of reaction to these things. I mean, I think I have to drag it out of you. She was just like, oh, don't stop. She wasn't like, what the fuck? You're cheating on her.

No, I mean, you could tell that she was upset. I mean, she was very upset. So she says, okay, so you didn't make that point. So when she says, don't stop because I'm here, she says it rudely. like go right rudely okay so that's what's but thank god i'm involved in these conversations and people always get mad at me for interrupting but i am needed in these calls okay because the way you make it sound like it actually could sound like she would like the way you said it sounded like she's actually like into it like keep going don't stop but no she was like pissed she said

don't just stop because i'm fucking here and then she let you finish and then she pulls you inside to talk to you okay that's where everything just came out in the open. And so I think out of hate or maybe out of anger, she, she kind of like, like wanted to take that dominant role or she started making me wear paintings full time. You know what I mean? So she, you know, she says, you come in the house and you say, listen, I just, I just got to explain to you. Because is she like, what the fuck? When did this start? And then you have to tell her that you've been doing this the whole time. And then you tell her like from the beginning. Yeah. I mean, I told her everything. You said, okay, listen, I have to admit, like, I've been doing this with him forever since

I'm, you know, whatever. And like, she, so she finds out that you're cheating on her this whole time with this guy. Yeah. So, I mean, she was, she was, uh, pretty upset at the time. But, uh, when I told her, I wore, like, I wore, like, I wore girls clothes and, and stuff like that. She, I don't know, if it was just like, and I don't know. I don't know if she was into it or I couldn't, I couldn't, I couldn't tell you because you'd never told me. And what does she say? Doesn't she have questions for you? Of course. Okay. So tell me the conversation.

Okay. So like the conversation went something like, okay, so how long have you been doing this? And I told her how long I had been doing it. And then I started telling her, you know, about the girls' clothes and how I wore panties when I would do it and dress up for him. And she, I mean, she was pretty, she would laugh. She was laughing during the conversation and just she just thought it was just like crazy. Like, this is crazy. I can't believe this.

You know what I mean? And yeah, it just went from there. I mean, like, she told me that. Let me ask you this. Does she like break up with you? Why did it? And why does she decide to stay with you? We stay together for about a year.

Yeah. Okay. But she didn't like at that night threatened to leave you or anything. I mean, she was like, that was never a conversation that was had, even though she found out you were cheating on her this whole time with your friend? No, I mean, there was like, there was like four or five days of silence, like, where we didn't talk to each other and just avoided each other and everything. But she never left.

You guys stayed in a relationship and eventually does she like, okay, does she ask you about like the dressing or anything or she just goes out and starts buying you panties? How does that come to play? Yeah, it's kind of like she threw away all my boxers and like told me I was going to wear panties from now on. So yeah, kind of dominant. Not really, but you know, it's interesting. So she, like right after this scenario, she throws out all your boxers and she's like, I got you a bunch of panties and this is what you have to wear now? Yes. Okay. Maybe she's just trying to take control of your interest and make it be a part of like you and her instead of like something that you're going to do

outside of her. Like she's just like going there instead of having you doing it behind her back. I don't no. Did you ever ask her? I never asked her. Never had that conversation with her. So she just tells you you're going to start wearing panties. So you start wearing panties. Okay. And then what happens? So I started suggesting that I wanted like more out of it. Like I wanted to wear thigh highs. I wanted to wear, you know, mini skirts and and all that. So she let me, you know. And she would call Brian over on her own. me knowing and I would do that in front of her. Was she turned on by it? She was. She was really, she would, I mean, she would play with herself while I was doing that to him.

Did she ever fuck Brian herself? No. You didn't want that. Not that I'm aware of, but no. But you weren't interested in that happening. You weren't interested in being cucked. You didn't want her to be with Brian too. No.

Okay. So, and Brian was cool with her there, right? obviously. Does she know Brian's girlfriend? What's that? Does Brian have a girlfriend at the same time that she catches you? Because is she friends with Brian's girlfriend? I mean, this is your best friend. Doesn't your best friend have a girlfriend too? Yes. Does she know her? No, they don't know each other. Even though you guys are best friends, the girls don't know each other? How is that possible? They just, they never talked. They never spoke. They just didn't have anything. Yeah, but you guys are best friends. You never go out together,

all four of you? No, I mean, she had her. own little girl group that she hung out with. She already had her friend group that she did everything with. And so there was like never any time that they crossed paths or. Yeah, that's a little weird. I don't understand that. I've never had a boyfriend that I didn't know his best friend's girlfriend. Do you know what I mean? Like you would think at parties and house, you know, that you would be all in the same place. You're besties now? No, it just didn't work out that way. Okay. So your girlfriend doesn't know his girlfriend. She's, you know. She's now in on the picture.

By the way, she didn't do anything in this situation to push you to anything. All she's doing is getting involved in what you were doing for the past eight years. I don't know why you think she had anything to do with pushing you in any kind of direction. Why do you think? Yeah. Why do you put it? I mean, I think when she implemented the toys, the sex toys, you know, the dildos and using them on me when I was, you know, giving Brian blow jobs, you know, it just, it kind of made me feel more girly. and, you know, less of a man.

Okay, so when does she start implementing toys? Implementing toys? It was after, I would say, six months maybe after I had gotten caught. Well, tell me that story. Well, she ordered them online, so they came in the mail. And one day I had came in the bedroom and they were laying on the bed. And I asked, you know, like, what are those? those yours and she just kind of like smiled and I found out later that day that when Brian came

over what they were going to be for. Okay. She didn't tell you. She's not talking you about it. She's like she's just like sort of being very subtle about it. She left them there to show you that she had them. But she didn't say let's use them now or I'm going to use them on Brian. You didn't know. You didn't ask any questions. Oh my God. How did, how were you raised to not have any voice? you never ask one fucking question. Oh my God, what happened? I don't understand people like that. So, okay.

So, you know, she just has these things laid there and you're like, oh, that's interesting. I mean, were you turned on? Were you like, oh, I hope she uses them? What's the deal? Yeah, I was actually turned on by it, like, not knowing what to expect. So I was very curious, like, what they were going to be used for when I saw them. So when, so you're, so at this point, though, as well, I mean, Brian is, coming over and you guys are now this isn't happening on the DL anymore like you know she's involved

every time correct and it's out in the open right okay do you ever go any farther than him just suck in a dick or yes or no uh no okay so Brian comes over and those toys are now in play and what goes down okay so Brian would show up and sometimes we would drink you know just to kind of light in the mood and it would always end up in the bedroom with me dressed up and she would always help me dress up making sure that you know that I looked I guess pretty cute frilly so yeah and so I would give them blowjobs and she would use toys on me what kind of toys they were we don't even know they were dildos okay multiple sizes uh three of them she had three of them that she ordered Okay. And what was the difference between them?

One was pink. One was like a flesh looking one. And the other one looked like realistic, like realistic looking. Okay, cool. So she got a variety. She's got these dildos. You're blowing brine. And then she like comes behind you. And what does she do? She lifts up my skirt, pulls my panties down and lubs lugs me up and just starts sticking them in my ass. Did that hurt? I mean, does she get you like turned on? Like, I mean, has she ever had anal sex? Because you kind of can't just like ram something in somebody's ass. Did she know what she was doing?

I mean, yeah, it was progressive, you know? I mean, little by little. She knew what she was doing. Right. So after the first couple of times, I mean, it just started getting used to it. And like, I was taking the whole thing, you know? Yeah. Yeah.

Did you like it? I did. I did. I actually loved it. I mean, it was great. You know, I'd never thought that anal sex could be so stimulating and feel so good. Because you had never sort of looked into that area on your own. Okay, so did you start playing like that with your girlfriend too when Brian wasn't around?

Or like when you were with your girlfriend when Brian wasn't around, it was just like straight heterosex between the two of you? We would have sex, but I mean, the toys were like, I mean, they were there. They were always, we were always using, or she was always using them. on me. So she liked to dominate you. She liked when you were sister. Would she want you dressed up with her as well? Yeah. I would wear like little 90s to bed, you know, with matching panties and stuff when we would go to bed. Do you feel like your dynamics of your relationships changed after she caught you when she became the dominant or was like the change only in the bedroom or did it change also like in the rest of your relationship? Yeah, the whole relationship changed.

Right. I would think so. And like, what, what did it change? What did it change into? Like, what was the vibe after? I would say that we were more distant and it was only like, like, I was like her little play thing. She would, I knew, I knew that she was texting another guy. So I didn't know the whole thing. I didn't know the whole thing, you know, about that. I never asked really questions, but I knew that they were texting back and forth all the time. Yeah. So, yeah, there was definitely distance after that. definitely but yet the the sex was like full on but maybe she was like punishing you or something like you said didn't you say that maybe yeah yeah like out of anger yeah out of resentment out of like just disrespected her so she's going to do that back but she doesn't understand that you're digging all of that I'm loving every minute every last second of it yeah but it might have not have been coming from the right place for her but that's a part of the turn on for you

how fucking twisted we're like in the upside down world yeah and then you know the whole like sissy names the pet names that she had for me too like while i was doing that you know like you know sissy cocksucker sissy faggot, you know sissy boy panty girlie boy she was humiliating you yeah it was all all turn on yeah yeah and for her it was a way for her to release her anger at all your cheating and keeping secrets and all that from her but at this point how do you how did you know that she was texting somebody else. And was that like something that you found out after the whole Brian thing? Or was that something that you thought you realized before? Yeah. I mean, I've seen her on her phone a lot. So I asked her about it and she kind of just came clean and said, yeah, I'm texting

another guy. You know what I mean? So I was like, is it serious? Are you all having sex? You know what I mean? Like I had so many questions, but yeah, I never got like the answers. I mean, who knows? They could have been having sex on the side. I really don't. Let me ask you this. I would assume she has no problem telling you, yeah, I'm texting someone else because this must have come out after she caught you, correct? This wasn't before she caught you or Brian, right? Correct. It came after. She was probably revenge. There's no way she wasn't fucking that guy. You know what I mean? She was getting you back. She was revenge fucking. That's what people do when they stay. Yeah. That and we were splitting bills, you know, on the house and everything like that. So it was

kind of like, you know, I guess a win-win for both of us really at the time, you know. Yeah, for a while. I mean, like I said, she was able to get her frustrations out on you. Listen, no matter what happens in a relationship, even if your partner does the worst thing to you, like all your feelings for them just doesn't go away in one second, right? She really cared about you. She was with you for a very long time. It's not easy to walk away from that person, even if you wind up finding out that they like to wear pandies and they're sucking their best friend's cock.

you don't mean like she didn't want to break up with you it was really hard but she wasn't happy and she had a lot of resentment because of what went on and maybe this you being a cissy wasn't and you you know sleeping with your best friend like wasn't like ideal for her so she started to like establish a you know a side piece that's what people do you know yeah why did you guys break up eventually eventually it just uh i guess she just got tired of the whole situation and just wanted to move on. She had already had somebody lined up anyways. So she would have probably never left if she did it, don't you think? Yeah, that's why she was technically like I guess. She was trying to find like, you know, she was trying to move safely to something else. She wasn't just going to

leave you for nothing. How do you know she left you for somebody else? Like what did she come to you one day and say? Like how did how did the breakup go down? Well, I mean, she just kind of told me that She was tired of this relationship and that she She just wanted us to You know split up. She didn't want to have anything to do with me anymore And so she packed all her stuff and she left one day She didn't tell me where she was going where she was going with or anything like that Okay, so obviously it wasn't good for the whole year anyway

It wasn't a surprise to you that she comes to you like that, right? But you and you found out later on that she did go to another guy's place? like she was with another guy? Yeah, she had moved in with another guy. Probably that guy she was texting maybe. Do you know? Yeah, okay. So you know, so you don't even know which guy it is, but you know she's with a guy and she left you.

Now, so where are you at? How long ago was that breakup? Like I said, it was about like when I was about 26, 28, somewhere around there. 20, yeah. So how old are you now? So how many years? Like four years ago? Two years ago?

I'm 32 now. Okay. So have you dated? anyone since her? No. Okay, but you continue to dress, correct? I do. And you continue to blow your friend.

I do. What do you do about those toys? Do you have stuff you use yourself now, since you like the anal action? Yes, I have my own toy collection. Okay. Now, does your friend ever use them on you as well when you're together with him?

No, no. He's not into that. No, he's not into that. that his girlfriend is he still with his girlfriend does his girlfriend have any idea what he's doing or has he just been able to hide it i'm not sure i'm not sure if she knows if she's told her like i don't know i like i think you know i think you know i mean do you hang out with him and her does she give you weird looks i don't know she doesn't yeah she i mean like i've seen her from i see her from time to time like when they're together but like like we we don't talk or anything like that so yeah i don't

think she knows. I bet you anything she doesn't know. Do you, okay, so have you, you know, you hooked up with that other guy, like you have your friend. Do you have any desire to hook up with any other guys besides your friend? Or do you have it like, because you have your friend and you have your toys, like you're kind of totally taken care of. Yeah, yeah, that's, that's kind of like how I feel at the moment like right now. Yeah, and you've had him for a long time. I mean, you guys have been, have this deal going down for a while, right? But who do you have sex with yourself because like you're not getting pleasure right you're being denied i know that that's like hot for you and stuff like how do you get off do you have girls that you've dated booty

call girls or like what do you what have you done in the past couple of years that you've been single no nothing really i mean uh i mean i've called girls and hooked up with girls but like it was just like a one-night stand deal you know what i mean like and that's it do you have a desire to be with another girlfriend like do you want another girlfriend's if she was dominant and would Play like the, you know, like, you're the last girl, right. Like, you know, God is mistress role. You know what I mean? Yeah.

Of course. I'd totally be into that. It's kind of interesting. And now I'm realizing why you kind of said, oh, she's the one that really made me into this whole specification. You know what it is, is that she didn't get you into it. What she got you into it is how you want to be treated by a woman. And it kind of was the perfect storm, right?

Like, she kind of did what she did to you out of a little bit, probably a, anger, right? Because of what happened and stuff. So, but you then got wired into liking it. And now you want to like, if you're going to be with a girl in the future, you want it to be in that kind of way with your ex-girlfriend, right? And I have to tell you, I'm going to be honest. Okay. I just think that's a hard sell for a girl. Like, when you care about a guy, it's like kind of opposite of what you want to do with them. You don't want to kind of humiliate them and make them feel like a sissy loser, you know, because you might lose your attraction. to them. Do you know what I mean? They're just like a weird fine line that happens with this kind of behavior when guys are into humiliation. Same with the guys that are into small penis humiliation. Like I worry for them because, you know, I had a girl on it. It was such a great episode. You should

listen to it. Her name was Eress and Raven. And she had a boyfriend who was a big cock and he loved to be humiliated and stuff, you know. And over time, I think it becomes difficult for the girl to like keep her respect and her interests and her hot feelings for a guy that wants her to like put him down and look at him as a girl. You know what I'm saying? So it's like a real fine line. Now your girl was naturally doing it because she was pissed at you, you know, but to get a girl that cares about you that you haven't cheated on, you know, might be a little bit harder. But if you do it like, listen, let's just like roll play it out, you know, and it's only in the bedroom and only keep it in the bedroom, like, that's how it's going to work. You know, don't let it bleed out because it wasn't a

healthy relationship that you had with that girl once it turned that way. And it was because of, like, the cheating and stuff, right? So, but you want, like, that situation, but healthy. Do you expect that if you meet another girl that you would be honest about the cissification, the guy thing, all of that? Or do you plan on going in and not saying anything? Do you have any idea about how you're going to roll? Yeah, I would definitely like to be up front with what I'm into. Yeah. And so, So, yeah, just straight from the get-go. So hopefully I find someone that's into, you know, cisifying men and feminizing them. And that kind of like ginks all that stuff.

Yeah, listen. And I'm sure there's girls out there like that. And, you know, you'd be really smart to go on like a fetishy, like a kink dating app or something, you know, like in a place where like, I mean, listen, in your generation that people are so much more open-minded and stuff and people are into all different things. So I think people are a lot more honest about what they're into and you're more likely to find a girl that's not going to judge you about it. It's not like, you know, 30 years ago when it was like every girl would be like, what the fuck younger? People are more open nowadays. But, you know, maybe you get on those apps where it's like a little bit like you can sort of present and put all your stuff out there ahead of time. And then it weeds out people who are not who are not into it and you find the girls that really are.

Because like, like even though I say, it was probably wrong of me to say it's hard to find a girl to do that. I have talked to girls who like to fucking dominate. You know what I mean? They are out there. So if you like, you know, if you're dating, if you put yourself on a dating app while you're just living your life too and you put that out there, you know, maybe you'll find a girl into it. So listen, do you have pictures for my Patreon? Have you dressed out? I do.

You want to? Okay. Yeah. Did you send them to me already? I don't know. Yeah. Like on your phone? No, did you send them to me already?

No, I haven't sent any pictures yet. Okay, great. I can. Oh, yeah. Definitely. I want you to send them for my thing. Now listen, what I say now is every cross jester who calls in or hosers, they get like free access to my Patreon. You'll love it because there's so much extra content in there. You'll also get free access to my Discord when we hang up and get my thank you email. That'll give you free access to my Discord. You'll dig that for sure.

But send me the pictures for my, you know, to my phone for your episode. It'll probably be up not just on Patreon, but on my podcast. So it might take a while, you know, because I just do fetish episodes on Friday. So I will keep you posted. I'll send you the link to free access to my Patreon when your, when your episode goes up and you'll get a whole year free, okay? Okay, cool. Yeah, where did I send those pictures at? So send it to me via email. Send me some pecks, okay? Okay. Do you have an email or are you going to send me an email? No, no, no. You emailed me. Strictly anonymous podcast at gmail.mell.com, haven't you? I mean, how did you get the link to call on? Oh, okay. Okay. So email you to that email. Yeah, to my

podcast. Yeah, yeah, yeah. Put it. right to there. Okay. Awesome. Thanks so much for calling it. Okay, cool. All right. Bye. Bye. Bye. Bye. Good news. Strictly Anonymous Podcast is looking for people to call into the show. So if you lead an interesting, naughty secret life that you want to talk about while remaining anonymous or not anonymous, if you're out and proud, that's cool too. Send me an email, strictly anonymous podcast at gmail.com. That's strictly anonymous podcast at gmail.com. Or go to my website, strictly anonymous podcast.com and click on be on the show. If you have a short confession that you want to get off your back, call my confessions hotline. 347, 4203579. That's 347, 4203579.

You could call that number 24-7. I change all the voices on the confessions too, so you remain anonymous. The number, the website, and the email address will all be in the description. If you want to follow the show, follow me at Strict Anonymous on either Instagram or Twitter. That's at Strict Anonymous. And if you want to sign up for my Patreon, you're not only supporting my show, but you're going to get all of these episodes early and ad free. You're going to get anonymous picks of all of my guests. Most of the girls send me in anonymous hot picks of themselves. And some of the guys are sending me in anonymous picks as well.

You also get access to my private Discord where people are getting super naughty. If you sign up for my Discord, you could post whatever you want and talk to my other listeners. To sign up for my Patreon, just go to patreon.com slash strictly anonymous podcast. That's patreon.com slash strictly anonymous podcast. The links and everything else I spoke about are all in the description. Thanks so much for listening. 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 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 skisible.

around. You could read the whole book. It's available in eback 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 Podcasts at gmail.com.

That's Strictly Anonymous Podcasts at gmail.com. And I will send you the link to Discord. So anyway, thanks so much for tuning in.