Strictly Anonymous Confessions - 047 - Jay is Dying to Watch his Girlfriend Bang Another Guy

Episode Date: November 11, 2014

Jay started having secret threesomes with random couples in college and now he's looking to get his girlfriend involved. He is obsessed with seeing her hook-up with another guy but he's not sure how to broach the subject without turning her off.  Is there a good way to gage her interest without rocking the boat, will she be open to it, is he bi? Tune in for all the details.   **To see anonymous pics of my female guests + hear anonymous confessions + get all the episodes early and AD FREE, join my Patreon! It's only $7 a month and you can cancel at any time. You can sign up here: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.patreon.com/StrictlyAnonymousPodcast⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and when you join, I'll throw in a complimentary link to my private Discord! MY BOOK IS NOW OUT FOR PRE-ORDER!!!! Strictly Anonymous Confessions: Secret Sex Lives of Total Strangers. A bunch of short, super sexy, TRUE stories. GET YOUR COPY NOW: https://amzn.to/4i7hBCd To Join SDC and get a FREE Trial! click here: https://www.sdc.com/?ref=37712 or go to SDC.com and use my code 37712 Want to be on the show? Email me at [e-mail] or go to http://www.strictlyanonymouspodcast.com and click on "Be on the Show" Have something quick you want to confesss while remaining anonymous? Call the CONFESSIONS hotline at 347-420-3579. You can call 24/7. All voices are changed. Sponsors: https://bluechew.com Get your first month FREE! https://butterwellness.com/ Try the Butter Wellness perineum massager and use code STRICTLY for 20% off your entire order Follow me! Instagram https://www.instagram.com/strictanonymous/ Twitter https://twitter.com/strictanonymous?lang=en Website http://www.strictlyanonymouspodcast.com/ Everything else https://linktr.ee/Strictlyanonymouspodcast Learn more about your ad choices. Visit megaphone.fm/adchoices

Welcome to the Strictly Anonymous Podcast. Conversations with online strangers. We play ads online. Craigslist is definitely the gift that keeps on giving. Real people respond. You go to Singapore or Thailand. You can't not do it. The temptation is just too much.

Real problems. Does your friend know that you're banging her? No, he has no idea. And anything goes. The motto of the show, let your Greek flag lie. Probably the only good advice I'll ever give you is to re-hide your whips and change. Here are your hosts, Kathy Kay and Tommy. Hey, welcome Mr. Green on this podcast with Kathy.

And we have on the call today, or I have on the call today, a guy who sent me a really quick email. I found him on Craigslist, and he sent me in a quick email and said that he was actually obsessed with watching his girlfriend, fuck another guy. Like, that's just what he's really into. Now, I don't know whether he's already done it, whether. they engage in that or whether he wants to or whether he's ever done it before. I don't know any of that stuff because he didn't give me any other information, which I prefer. I prefer my calls

like that. I like to not know anything so then I could ask a zillion questions. So that's who we have on the call. If you want to call into the show, I'm always looking for callers. I get most of my callers from other Craigslist. I've used Adult Friend Finder. I've also used Backpage. But Craigslist is basically the gift that it keeps on giving. I get most of my people from Craigslist. It's awesome. But if you're listening to the show and you just want to call in because you're looking for advice and you have a problem or you just live a secret life and you just want to, you know, dump it on somebody or just get it off your chest, give us me an email and I'll have you on the show. I'm always looking for people to call in. Especially women. I don't get any, I don't get a lot of women because I advertise in and the places where advertise women don't go. So if anyone are listening and want to call in, it's totally anonymous and you could spill your shit to me and if you need help or whatever. it is. Definitely send me an email. Send an email to a strictly anonymous podcast at gmail.com and I'll have you on the next show. The guy that's calling in today, I'm calling him Jay. It's like the letter J, but it's a J. That's his name that we're going to call him because that's

his email that he's sending to me. I'm assuming it's a fake name. And Jay just like I said, wants to watch another guy fuck his girlfriend. I don't know if he wants to join in either. I don't know like I said. I don't know any of those things. So anyway, I'll be right back with Jay. lifestyle or situation you can't talk about to anyone, to anyone? Or do you just want to let your freak flag fly and be on the show? Well, Strictly Anonymous wants to hear from you. Send us an email, Strictly Anonymous podcast at gmail.com, with your story and your anonymous name.

And remember, everything is strictly anonymous. strictly anonymous. Hi, is this Jay? Yes. Hey, Jay. How are you? I'm good. How are you?

Good. So, I'm just going to start taping. Okay. I like when, sometimes people, like, email me a lot and they tell me a lot of information beforehand. But I prefer when it's something like with you, where you, I mean, you just told me, basically, your deal is you're, like, obsessed with having your girlfriend, fuck other guys. And you watch, right? I mean, that's all I like. know.

I don't know if you've done it already. I don't know if you, you know, and that's the kind of stuff that I want to know, actually. Okay. So have you guys, like, already gone there? Like, do you watch her have sex with her guys? No, I haven't. How long have you been dating her? Does she know?

I have so many questions. First of all, how long have you been dating her for? I've been dating her for about two years now. And before her. Or, like, is this something that you've always wanted to do with your girlfriends or just with this one in particular? This is something that I've kind of always wanted to do. Like, I kind of, like, I've had, before I started dating her, like, I had a couple of, like, three things. And, like, I really enjoyed, like, watching the other guy and with his girl.

And I kind of want to do that again. But, like, you know, like, I don't know. It's just weird to bring up to your girlfriend. Exactly. Totally. But wait a second. So let's start with your threesomes that you've had in the past. Were they stuff that you, like, sort of found on Craigslist or, you know, and like you were with a guy and their girlfriend as opposed to you and your girlfriend with another guy?

Exactly. Right. So when did you start getting into doing these threesomes? When I was in college. Did it happen like, like, was it a first time? Was it like a drunk in college thing? or was it just something always, like you sort of did secretly on the side? It was something that I sort of did secretly on the side.

That's okay. That's what I love talking to people about, because I think a lot of people have secret stuff that they do on the side or think about or, you know what I mean? You're not the only one. But wait, so you were in college and you just always had this thing where you wanted, and it was like your threesome's involved, you, another guy, and a woman, right? Exactly.

So you like to watch a guy screw another girl. So you did it with always strangers? Yeah. And how did you find these people? Through Craigslist. Always Craigslist is like the gift that keeps on giving, right? I mean, for me, though, what I find, a lot of times I'm talking to guys, I always post on Craigslist. That was like, I always wanted to do a call and advice podcast show, and I'm like, I don't know where to get people because I didn't want any of my friends to know what I was doing.

This is my secret life, right? But I So for some reason I posted on Craigslist in the personal section And I just got like all these really interesting people calling And a lot of times it's guys looking just for girls to screw You know And in that situation I get a lot of them are very frustrated Because on Craigslist they don't find real women

You know a lot of times it's like men or dudes or prostitutes Or there's not a lot of like you know They can't get what they want You I'm assuming have been successful in finding like guys with girlfriends That want to bring another guy into the men Yeah, I have been successful. Yeah? Yeah, or I don't know.

I haven't been extremely successful, but I've done it a few times. What's a few times? Three? Like five. And have any of them been like ongoing experiences or are they typically like one-offs? Like you'd just screw them and then everyone's like, oh, see you later. I never want to see you again. One of them was like more ongoing.

and it lasted about like a month and then they kind of just stopped replying to me but you but you were with them like you guys all had sex yeah and now let me ask you this it's not a gay thing right like it's not like

it's more like are you straight do you consider yourself straight um I don't like maybe like slightly by I don't know like I don't know like I did go down on the other guy

And that was kind of, I found it hot for like the first, like, minute. And then after that was kind of like whatever. Like whatever or like you weren't into it at all? Or. Like, did you start, like, at first you thought, so you were giving him a blowjob. Was this one of your first experiences? Yeah. Right.

So you started blowing him. He was into it? Yeah. And you were into it at first. And then, I don't know, excuse, it was something that I kind of, curious about and then I guess kind of like the novelty of it wore off. Right. And you're like been there done that after like a minute and you're like not interested anymore? Pretty much. I mean did it freak you out or did it make you sort of realize like oh this is I'm not

into this or did you know? It didn't really freak me out. I was just kind of like oh I'm not really into this but then like everyone's like I kind of want to do that again but just for like a minute. weird Do you think that like, you know, you're into the whole visual thing of seeing that man with the woman and that plays a part in it, you know what I mean? Because it's not like you're into seeing your woman with another woman, right?

You want to see another man. So, like another naked man banging her, right? Mm-hmm. And so that... There was, like, one particular experience that, like, stands out in my mind because I always think back to it because it was like the best. What was that one about?

Tell me the story. So basically, like he was writing her like doggy style and then I was underneath her like looking her clip. Uh-huh. Like meeting back and watching and that was just like I've masturbated to that like a thousand times now. Right, right. Because that's really what you're into, right? Like that sort of vision that you're,

you have is what turns you on and why you'd like to have the threasons right exactly and are these people that you're with um are they boyfriend and girlfriends most time couples mostly boy and girlfriend and one of them was husband wife how old are you i'm 26 i always ask my colleagues because i try to get a visual even though i like to remain anonymous and never see anyone or know anything but i want to always know kind of like I always ask people like on a scale of one to ten what do you consider yourself like are you what would you consider yourself on a scale of one to ten? Probably about a seven a seven yeah and the people that you've met through Craigslist and these couples that want to screw have they always been kind of hot like are they attractive to or what

kind of people are they um yeah they have actually been I was kind of support surprised that is I know well except for one time when I met a couple like we just like went out for drinks and like their pictures look like they were like 10 years old but um other than that they've all been like really attractive really and do you guys how does it work like so you they post ads with pictures and they're and then you guys exchange pictures because they have to say okay or no or whatever like do you do you size each other up ahead of time yeah like they post an ad like i reply and like a couple of pictures they if they're interested replies in some pictures we talk a little bit and then like i usually like to meet them like somewhere

public like a bar or something and then go back to right and most of it has it ever gone like i mean you always meet them and it always winds up back at their house have you ever met them in a bar i've been like oh fuck this i'm not going on with them the couple that didn't look like the picture Oh, you didn't go home with them? No. They were too old? They were actually,

or yeah, they just weren't my type. Okay. And then, yeah, there was another time when I think her boyfriend wasn't into me. So,

like they said, we're not interested. Oh, they denied you. And they just told you straight up, hey, by the way, we're not really into this. Uh, no.

They were like he's not feeling out. Right. If I went on on date with a guy and he said that I'd assume that he wasn't into me too. Yeah. And then I was like, hey, is he feeling any better? Like two days later, never heard anything back again. Right. So I'm pretty sure they just bring it. So do they send, do people send face shots beforehand or is it just mostly body shots? Like dick picks and stuff?

It depends. Like, I prefer to like, like, send a face picture, like unless I know they're definitely interested. Yeah, most of the time, like before somebody will meet, they'll probably be exchanging face pictures. Right. And so when you've done this, you said you've done it five times. Have you done it when you're in relationships?

Like, do you cheat on your girlfriends in these kind of scenarios, or do you do it when you're single? Yeah, I've only done it when I was single. You've only done it when you were single. I knew a guy, a good friend of mine who met a woman in that scenario. in that scenario, like he met it, he didn't do it through online dating or anything like that or Craigslist.

I think he just met this girl in a bar and she was like, took him back to her place, but she had a boyfriend and she wanted him to watch her, fuck this guy. I don't know if it was, but, and somehow my friend wound up dating her. And that was her thing. That's the kind of girl you need. And that was like her thing.

But I got to tell you, she was like kind of whacked. You know, I mean, she was like a crazy girl for him to date. I mean, like, you know, and that's the hard thing. Like, you have a relationship with this woman for, like, two years. Like, what are the odds if she's kind of sane and you could keep a relationship with her that she's going to be like, oh, yeah, let's bring a guy into it and I'll fuck him and you could watch, you know, without her being kind of like crazy in a certain way. Yeah, exactly.

And, like, if she's not into it, I don't want her to, well, like, I don't want to end a relationship over this one little thing. Yeah, it would be great, but it's not like I absolutely need this to happen. right and the problem with the woman you know because i mean if my guy like came to me and asked me that you know so many different things would go through the girl's mind you know but i think a part of it would be like do you not like like me like you know what i mean because somebody would think like wouldn't you be jealous to see me screw another guy do you know what i mean would there be no jealousy for you with your girlfriend like i don't know because it hasn't like happened but I don't think so.

You don't. Like if you found, let me ask you this though. If you found out that your girl was cheating on you with another guy or she fucked your friend or something, would that freak you out? Well, I actually

did have an ex-girlfriend who like she made out with someone of another guy. We go that far as she was kind of drunk at the time too. And like when she was telling me, like I was kind of upset, but at the same time it's also really, really turned on. Right.

So I didn't tell her that, but I don't know. I feel like it's different if I say like, okay, let's do this versus her going behind my back and giving that. Right, totally. But you still have, you can't help that you're wired in that way. So even if they're cheating on you, you do still find it sort of hot. So you've been hitting your girl for. two years and you've obviously never brought this up but you want to i mean you're on craigslist you found me on craigslist right so you're on there looking for something for the past two years have you

looked for situations to do this behind her back but nothing's come up or would you never do that behind her back are you like not a cheater or cheater what i occasionally am looking for is like another guy from bringing in so like if there was another guy that I could watch her with. That's what you're looking for, right? Yeah, that's what I'm looking for, and that's kind of a while of my credit's list. Right, so you're not, but in the past two years, because you're not getting your rocks off in that area, because you've been with her, right?

You haven't been with any couples. So have you thought to look for another couple just to go do that and have that experience so that you could, like, release that sexual attention, or have you been completely faithful to her? I've been faithful to her. So it's like what I've been doing like is just like looking at the ads and using those to get off. I haven't actually responded or anything like that. Right. That would be fantasizing.

And that's fine. I mean, that's not cheating. I don't think so. Do you? No, I don't think so either. It's like similar to looking at porn, but slightly different. Yeah, sometimes it's like better. Like sometimes, I mean, I don't know.

Like, how do you feel about cheating? Are you typically a monogamous guy when you're in a relationship? with a woman or do you not like give a shit about that like have you always been faithful to your girlfriends yeah right so maybe it's better if you keep that in a fantasy and the only way you do it is if she says yes i mean it's hard i got to tell you we're calling you jay right like it's hard jay to find like to you know to bring a topic like that up with a woman if you know and have her be into it you know what's your sex life with her like is she pretty like hardcore and really open-minded and sort of experienced and that kind of like what is she

likes actually um i think she's somewhat experienced she's actually like really into bondage which i enjoy too and we've just kind of been playing around with that and getting how much into bondage like she really likes being tied down to the bed and we got some like her we just got some like bondage tape that we've been playing around with. And she like likes to be handcuffed and blindfolded and all that fun stuff. So there's bondage tape. What's the difference between bondage tape and like duct tape? At least like sticks to itself, which is really, really nice because it's not like sticky or anything like that.

And you don't have to worry about tying nuts and all. Oh, so it doesn't stick to like the skin or areas or anything like that. like you say, it only sticks to itself. Mm-hmm. So she's really into that. I mean, listen, you know, that could escalate into other things. The problem is with you wanting her to do that, it's like it could wind up opening up. I mean, if she's into it, it would be great, right?

And then it doesn't matter what you've done in your past or anything. But it could just wind up opening up a can of worms because it's just like, you know, it leads to all the questions that I have for you, right? And before you know what you're telling her, like you've given a guy head, you know, and maybe she'll be freaked out by that. You know what I mean? Like, you just don't know. I mean, do you want to, like, bring it up to her?

Are you at the point where, like, that's what you, like, you're getting to the point where you can't take it anymore and you have to sort of go there or you want to? Like, I'm really, like, on the fence as to whether or not I want to or not. It's kind of where I am right now. Like, I just can't, like, I just keep on imagining all, like, the negative things that could go wrong. and I kind of talk myself out of, like, bringing it up to her.

How old is your girlfriend? She's 24. And what does she do for a living? She's in grad school right now. Right, so she's going to school. And she's, like, sexually, she's pretty open-minded. She's very into the bondage thing. Now that's getting, like, did she read that book or something?

Like, how did the bondage thing come up between you guys? Apparently, it's been, like, a long time, fantasy of hers, but she didn't read like 50 shades of gray. She just was like, I want you to tie me up. Right. She was always, she was always into it and she felt, once she felt comfortable enough with you, she was like, she let you in on what she really likes. Exactly. Right. I mean, that could lead to other things. I mean, maybe there's other things that she hasn't told you about that she's really into as well. Do you know what I mean? You don't know what comes after her bondage fantasy. You know, you got to keep.

going there and that's a good thing because that could open the door to other things as well. Has she ever been interested in being with another woman? I think so. Like I'm not really, she has had like one experience with an alma woman. And she seems like I've liked it, but

it seemed like it was more of a one-time thing but I don't know. Right. And when you think that like bad things would happen when you bring it up, like when you say like sometimes you think about but then you think like what are the bad scenarios that you imagine? Basically, I'm imagining, like, her, well, I'm imagining her kind of just completely freaking out about it, and just not understanding at all, and just reacting negatively towards it,

and basically, like, just thinking that, like, I don't even really know how to describe it, like, that I don't know. I don't want her to feel like just her being there isn't enough to make me happy. You see what it is. But, but.

Right. You have this other little thing that if you added into the mix, it would be really amazing. Mm-hmm. But it's a, it's a tough. I mean,

I, like, you're kind of like in a weird position. I mean, and I get, like, I don't know, like,

you know, I would never advise you. If I was your friend, you know what I mean? Does anyone, know that you do this besides me right now and the other couples that you fucked? No. Right.

So, you know, like, I don't know that I could ever tell you, like, you know what? You need to bring it up, you know, because I feel the same way you do. It's a 50-50 chance or maybe like an 80-20 chance or maybe it's 95-5. You know what I mean? That she's going to be like, what the fuck or not, you know? And you really, I mean, I think it's like, but you just don't know. And I think it's a little scary to risk a relationship if you have a good relationship and you really care about her, right? To sort of bring that up because, you know, it's just sex, right?

At the end of the day, it's not your whole relationship, right? You're just, it's just this little thing that if you added it in, it would be amazing, right? And it would be better than if you don't add it in. But it's not like anything's wrong with your situation without it, right? Exactly. Yeah. So like the best time to bring it up is when she's about to dump your ass and things are on the on the out. Do you know what I mean?

And you're like, okay, if you're going to go, we might as well do this now and maybe bring it up and maybe it'll either she'll leave you and be like fuck off or she'll be like, oh my God, I've been dying to do that. And it'll add some like, you know, a breath of fresh air and you'll have another year with her. But it's really hard. I get why you don't know what to do. And like I said, I would never advise you. I give on professional advice, right? I'm no like psychologist or anything. I just like talking to people about their problems and, you know, analyzing stuff.

But, you know, if I was like your friend, I would be like, I would be just as, I'm just as confused as you are, unfortunately, about it. You know what I mean? I feel on the same, I feel on the fence too because it's a hard subject. You kind of have to do it. I think that the fact that she's really into bondage right now and you're doing like these like things and, you know, I think is a good thing because it can lead in to that conference. And the conversation probably should never be and it's, you know, that you've done this in the past and this is what you've always wanted to do. The conversation should probably be like, hey, what do you think about that? And would you ever be into it? Maybe like, I don't know how I feel. Do you know what I mean? Like, did you ever think of playing it that way where it's something that you think you're going to try but you never did? Like lie about it. You know what I mean? Not sort of give, not sort of let her know that this is something you've done before and something you're into and something you would like more so.

be like, you know, bring it up in a way that seems like it's something you just thought about and you maybe, you know, she wants to experience with you and maybe you could be like, I don't even know if I'll like it, but maybe I would or maybe I wouldn't. Yeah, I don't know what you mean there, but like, I don't know. I don't particularly

like want like a lie to her. Right, you want to, right, okay, but it's not really, like, listen, I'm a very honest person, right? I can't stand fucking liars. I think the truth is just so much easier most of the time. It just really is. You know, but sometimes, like certain lies, like in a situation like this, does it matter

if she knows that you fucked other people in your past and did this or that this is like your secret? I don't think it does. Like, you know what I mean? I don't know. I don't see that as like a real lie. And so, you know what I mean? Like, so I don't think that it's that bad. It could be a better way to sort of segue into what you're looking for and not risk your relationship. Like I know what you're saying and it kind of makes

sense. It just kind of like I don't know. Like if she's, if I'm bringing up like have you ever thought about this and then she answers and then basically it's like why have you thought about this or like have you done this before? Right.

Can't you just? Right. You feel like you'd have to say yes. Right. I mean, listen, nothing that you did in your past would freak out. Like, you never did it with a girlfriend. You never did it with, like, random. I mean, I don't know if that's worse. Like, I don't know if she'd be like, what the fuck.

But if you're the type of person that would have to be honest, then you'd have to be honest. But it's not like, you know, you never did it when you were dating anybody. You only did it in the past. So I don't see why she would really care. I don't think so. she might though just be like a little bit like oh you know sometimes when you let your freak flag fly people could get a little freaked out you know yeah it just depends i mean if she's been with a woman and she's really into bondage and i don't know like is she very open-minded she seems like she is there was well i don't know there was one time when like i kind of mentioned to her that like i thought i might have been by and she like i don't know she didn't pick it very well. Oh, okay. See, these are the good

things that I need to know. So what happened in that situation? How did that come up? I think we were talking about something, and then I think I mentioned how, like, I forgot, it was some actor, and I was like, yeah, he's really attractive, and she was like, you find other men attracting, like, what are you by? And I was like,

well, maybe, sometimes I think I might be, and then she was basically like went off on this tangent about one of our other friends whose boyfriend was by and then like wound up being gay and it's like are you actually gay and I don't know she started

like I don't know I basically like yeah I was going to say how did you get out of it how did you take it back or I was like well or I don't know I kind of explained away like saying that some men have like

Like, I don't know. I didn't really explain it away very well, but she was. It was enough for her to, listen, a lot of times women, you know, don't want to believe certain things if they're not ready to leave somebody. So somehow you said something that made her be able to live in denial about it, which was good on your part. And you could probably do the same thing with this. But just so, you know, in that situation, you kind of lied like I'm telling you to lie,

which I think is smart. You know what I mean? You didn't tell her I sucked a guy off once when you brought that up, right? So you did do that, like, dipping your foot in the pond. You know what I'm saying? So I think that you could approach it in the same way. You sort of like felt her out without telling her the total truth. It wasn't lying.

It was just testing the waters. When you got the reaction that you realized, you backtracked a little bit, and that was the end of it. That's the same thing I'm telling you to do with the situation with, you know, her and another guy. How is it any different? Do you know what I mean? Like you're saying, no, I'd have to full disclosure. If I bring that up, I have to tell her everything. I can't pretend that I have it.

Listen, the conversation isn't going to be like, hey, babe, do you want to fuck another guy in front of me because I fucked other people? You know, that's not how conversations go. You're going to say, hey, do you kind of think, like, you know, just like you did it with the buy thing. And she's going to be like, what the fuck are you talking about? And then that could be the end of the conversation you could backtrack. Or she'll be like, I don't know.

And then it becomes a conversation. And then you feel her out if you get to the point where you're going to tell her about your past and stuff. but that doesn't have to come out right away. Yeah, I think I get what you're saying. And it really, I agree with you. That seems like the right course of action to take. You have to wait for the perfect moment

to bring up some sort of leading into that scenario, you know, conversation, feel her out by how she reacts, and then take it from there. And you'll be able to gauge because you're not an insane person. you know, you know, you'll be able to take the social cues from her of whether, you know, how much information you could give her without her freaking out.

Mm-hmm. You know, and you just need to wait for that sort of time. Do you guys watch porn together or talk about sex a lot? Like, I love to talk about sex with people that I'm into. Like, it's hot sometimes. You know, you talk about what you like and what you're into while you're sort of doing it. Do you guys talk about that kind of stuff? Um, like while we're doing it.

we do that a lot but not necessarily like the rest of the time right or not like beforehand right because you don't want to say it in the middle of like sex because she might you know you know she might be like what the if she's really not into it could really turn her off but like it could be like sort of for do you guys ever watch porn together or that kind of thing no we don't do that okay you need to like and the thing with the gay thing that just came up right out of like somehow i think you it just has to the conversation just has to come up in a way way that you're not really saying like, hey, I want you to fuck another guy in front me because that's what I'm into. Because I think it's too, unless you really know how she's going to react, she could, you know, she could potentially like break up with you for something like that, don't you think? Yeah, I think so. Yeah. So you can't go there. I mean, you're lucky that you're able to backtrack on the gay thing, you know, and I don't think, and let me tell you something because I know you're into this whole honesty thing, okay? And I think it's very like I said I believe in the truth I'm a truth teller like I love the fucking truth

but if you already know that your girlfriend is very anti the gay thing and it freaks her out you know there's no reason for her to ever know that you gave head to a guy for one second and if you ever do have a relationship with her and another guy unless she's like hey babe I want you to go down on him I would never go there because you already know that she's not into it you know, and that's not lying. That's just like not telling her the whole shebang because what does she need to know that? You're not going to cheat on her

with other guys behind her back and everything. So what does it matter? Yeah. You know, it's not like a bad lie. If you were living, it's not like you're living a double life and you're blowing guys in cars and then going home and you're straight, you know, it's not like what she's afraid of. She's afraid of a guy in the scenario with her friend

who's secretly gay and is by and he left the girl for another guy. and whatever. You know what I mean? What she's afraid of is not going to happen with you. So what does it even matter for her to know? You know? And if you guys start screwing like other guys and stuff like if she's into that that'll come out, you know, but you

never have to tell her that. You need to lead into it. I mean, are you constantly on Craigslist like looking for this situation? Is it like sort of an obsession of yours? Like, or do you feel like you're like addicted to it? I wouldn't say constantly. I think I would probably look on

credit with like maybe once or twice a month or something like that. Right. And sometimes you, like you say, you use that to like get you off. But you do you get close? Do you feel like as time goes by, you get closer and closer to just like needing to bring it up with her? Yeah, I think so. And so you're getting to the point where like you're dying. What's your longest relationship that you've ever had?

Previously I was in one for like two and a half years, which was the girl that I was dating before this. girl. And then I had a couple of relationships that were relatively short, told me about a month or two. And when you were with that girl, did you do the same thing? Like, you, did you never brought, yeah? She basically was like the first, like, real girlfriend that I had. So I don't know. I wasn't, I don't think I realized that I was into this at the time. Right. You were just so into just having a girl, or just figuring that whole scene out that you weren't like, like you were and you didn't have the time or you didn't think to go elsewhere

and remember your other sort of thing that you're into. Exactly. But maybe you just feel really comfortable. Like you and her have a good relationship, I'm assuming, right? Other than, like, and it's not even that this is a problem. I mean, besides this whole thing that you want on the side, is everything with her as far as your relationship okay? Yeah, I think so.

Is she someone that you would want to, marry? Like what, what, I mean, I'm like way older than you and I'm never been married and I'm not necessarily, I don't really buy into the whole thing. But I mean, I like commitment and relationships. I mean, is it, I don't know, do people get married when they're 26 or do you think about that at 26? I know I wasn't thinking about it, but are you, do you think about that or is this a girl that you might want to marry? Um, maybe, like, I don't know. It's like the thought has like kind of crossed my mind that maybe I could be seeing her for a long time. But it's more, or it's not like I'm planning on marrying her or anything like that.

Right, but you feel like she could be the one. That might be nice, maybe, if she is the one. I'm not sure she is, so. Right, but you guys get along really well and your sex is great, I'm assuming. Right. The sex is great. Do you feel like when you think about your future with somebody, do you think like, oh, my God, I could never be like with somebody that wasn't going to do that or live my whole life

if I commit to somebody without like being able to experience this? Or do you feel like if you lived your whole life with somebody and married somebody and were with them for 30 years that they weren't into it that you could be completely fulfilled? Yeah, like I don't know. Part of me thinks like I don't think so. Right. And sometimes, I mean, I don't know. I mean, I always liked role playing with a boyfriend.

and I think that if you have a really hardcore imagination and you're really creative, a lot of times you could, you know, create the scenarios that you want to have in real life that maybe you never would, right? Just in like fantasy with the person and sort of experience it that way. And then everyone's like happy,

but you don't really do it. But if you really go there in your mind and pretend, like it really feels like you did, like it's fun. I don't know if you could do that though because like the thing, you know, role playing a lot of times that I would do it. My boyfriends would be like he was a person and I was a person, we weren't role-playing like, you know,

another person there that wasn't really there, you know, like, could that, you think that that could, like, you somehow, like, do it, like, in a way? I don't know, I don't think so, right? Because it's like, you want another guy there, right? Like, if she were to pretend or you guys were, like, that wouldn't work, right? Yeah, I don't really know how you would do that.

You can't roleplay like a fake dude to come in, right? or you, it's because it's not about like, it's not about her with another guy and you watching, so you can't be the other guy, it's about you, the other guy, and her all interacting. You want that, you want that visual that you have when you were like beneath the other woman where you want her to be fucked by a guy,

doggy style, and you want to be underwatching, right? Yeah. Did you have that same scenario with the other couples that you're with? Not with all of them, but with, I think, like, with three of them I did. Right. And did the other guys ever try to hit on you, or it was only one guy that you had that, like, the buy experience with?

It wasn't that just one guy. It was, let me try and remember. They've all kind of, like, blended together inside of my mind now. But it was two different guys. So two different guys you gave head to? Yeah. but the same thing happened the second time where like a couple minutes into it you weren't into it anymore pretty much right and they were cool with that like they just stopped and then you just got busy doing other things and they didn't try to do it again with you

I kept or when they wanted it again I just did it you did it yeah okay is it hard for you to admit that Is it hard for you to admit that? Because I feel like you kind of left that out before. First you told me like, oh, I just did it once with a guy for a minute. And then I didn't really like it. And I was like, forget it. And then now you're telling me you did it with two guys. And then I said when they wanted you to do it again, you're like you did it again.

But you hesitated for a long time. I'll probably edit out the long hesitation. But you did hesitate for a long time to answer the question. So I'm wondering if you have like a problem with that yourself or you feel weirded out. that you do that? Yeah, I think I do a little bit. I don't know. Like, I didn't particularly, like,

want to, but it's not like a particular, like, didn't want to. It was just kind of like, it was... So is the thing that freaks you out about it, the fact that you sort of did something because somebody else wanted you to, sort of like the way a woman feels if she's being used by a guy.

Like, a lot of times I think women wind up doing sex. sexual things or things sexually with a man that maybe they don't want to do but because they feel pressure too and I think a woman feels that way afterwards like you know and then they feel bad about themselves and I'm trying to figure out is you're feeling bad about yourself because you feel like you kind of were forced to do something you weren't into or do you feel bad because you kind of it confuses you when you wonder like does this mean that I'm gay or not you know where is where's the confusion for you or sort you know where's your feelings of like feeling a comfortable about it come from

I'd say much more so like that I was doing something that I didn't want to help pressured into it. Right, right, right. And that's normal, you know what I mean? And it's like you're just in the heat of passion and it's just happening and you feel like, you know,

you just should because they're there and they want to and you sort of blew them before for a minute. So why, you know what I mean? You don't want to bust up the scene and be like, no, or put boundaries sometimes when you're doing something like that. it could be, you know, hard to say, no, women face that. I think women go through that all the time with men. You know, you don't want to sort of ruin the moment and be like, oh, no, I don't want to do that.

So you say yes to everything, and then, but sometimes you're saying yes to things that you don't want to. So that's just why you hesitated. Because I could tell that you had some weird vibes about it. So you're probably not by, I don't think, because you would like it, don't you think? I don't know, like I did for a little while and then I stopped. Do you watch Gabe? So that's okay. Did you watch,

sometimes you need to figure out whether you're by or not. You need to try it out. You know, you were open. You were like, maybe I am. Let me see what this is like. And then you did it and you were like,

oh, I don't really like it that much, right? Yeah. Yeah. So that doesn't make you buy. That made you buy curious. And then you realize like it wasn't really what you were into. But do you watch like,

besides going on Craigslist and like sort of jerking off to the scenario of like your girlfriend with another. guy. Do you watch gay porn? I don't watch gay porn. Like, like sometimes I go on Craigslist and then I look for like, I look at the Men for Men section. And then

I get off looking at other guys. It's just weird. That's why I kind of think I'm bi. Yeah, I don't think that that's weird. I think maybe you are a little by. Listen, I think that a lot of people it's like a, like, you know, fall on a different end of like a spectrum. Like, I don't think, you know, and I think that's like there's different

percentages and I think it's very rare actually I think to find people that are completely 100% hetero or completely 100% homo but I think you find them of course right but a lot of people and maybe most people fall on those ends of the spectrum but I think a lot of people fall somewhere in the middle men and women I think listen you're being really fucking honest on my podcast because it's anonymous and that's why I do it this way so people really tell the truth and I think a lot more guys if they came on in this scenario would be true about it. I think women admit it more because it's very accepted. You know, women with another woman, every straight girl's like, I have a girl crush,

and they're all like, you know, admitting to being slightly by. But, you know, 20 years ago, nobody was. No women was. But, you know, with men, I think it's still not really acceptable. So a lot of guys keep it sort of under wraps. But I bet you there's a lot of guys that are doing what you do. They just don't admit it. It's not that weird, I don't think, you know.

I have a test that sometimes I want to put. guys through where I'm just like I want you to watch some gay porn I'm going to and then I'm going to feel your pants in the middle of the thing and see if you're hard you know and you know how many guys I've had on my podcast that are completely straight that had gotten blowjobs from trannies and stuff and you know like I believe that there's a lot more slightly bisexual men than admit to it so you might be slightly by you don't have to be totally by you know what I mean you could maybe be by in your imagination but maybe in real life you're like oh oh, that just goes too far for you,

but you like to fantasize it about it in your mind. Yeah, I think that's kind of where I am. Yeah, that's totally fine. And maybe one day you'll get more into it or maybe not. But I don't think that there's that confusing or that weird. I think that sometimes what gets us off in our head is different than what would get you up. And that's okay.

And just like to leave it there and leave it as a fantasy is great. Because sometimes when I've lived out fantasies that I had in my head, in reality they weren't as good as it was in my head you know mean I think that that's fine I wonder like if you I think though because you have had the experience with the couples and you really liked it I think that if you were with your girlfriend with the other people I think that would be a fantasy that you actually really would enjoy in real life too and would be great for your relationship I just I just I just think it's going to be really hard for you to bring it up

and I think like I said I don't think it's 955 I think it's like a flip of a coin It's like a 50-50. You really don't know because when she flipped out about the gay thing, she didn't really flip out because she's like, you like guys, that's weird. You're fucked up. Like, you can't, like, you know, she wasn't like that. It was more about her being nervous that it meant you were gay and you leave her, right? Yeah.

Right. You know, I had a girlfriend that would meet guys that were by. She was very into like rock and roll dudes. And a lot of those guys have made out with guys. And she didn't ever care, you know. And at all. Like she wasn't closed-minded to that. And so I think like she didn't really sort of,

your girlfriend didn't like freak out in the way that made it seem like she's really closed off to you sexually be doing certain things that are a little bit out of the box. She just more freaked out because she was wondering, does that make you like gay or is there more that you're keeping, you know, stuff from her? And you fully like women, right? Yeah. Absolutely. Right. So I don't think that there's anything. I don't think there's anything. I don't think. I think with her you just don't know and you have to do it in the way that the gay thing. You have to wait for some perfect moment. And, you know, that moment will come. If you're smart enough to listen to what she says or say certain things, you could lead into that moment somehow and bring it up and feel her out and just sort of bring it up as if like, would you ever do that? Like, you know what I mean? Maybe bring it up in like, oh, when you had that girl, like girl, did you ever think of a threesome? Did you ever do that? And like a girl and a guy or

two guys and see what she says and then just like, I don't know, feel her out that way. It has to be like a conversation and you have to go into it pretending that or at least starting out with a conversation where it's something that you, you're just wondering about, you know, I wouldn't go into it being like, hey, do you want to do this? Because I've done this in the past and I want to. It can't be that conversation. That's too risky. Yeah, and even if she was, yeah, I completely agree with it. Even if she wasn't, like, approaching it that way, it just sounds weird. Yeah, I mean, right, exactly.

Like, what are you going to draft up a contract next? You know what I mean? It's, like, so formal, you know, and, like, I don't know, direct in a way that, something like that you should, like, sort of, it should come up in, like, a flirtatious kind of sexy way where you guys are just having a conversation about sex or, like, you know, feeling each other out, you know, getting to know her better in that scenario.

And because you're now doing all this new stuff, you know, with the bondage thing, I feel like that there's going to be a time where that's going to be able to come up. You know, you're going to have a window of opportunity where you're going to be able to sort of lead into that. And you just have to go in in the same way you went into the gay thing or the bisexual thing, which is just feel her out with your conversation. I don't think it's, I think it's too dangerous to ever go in and say it or somehow get her to bring it up. Like, I have that skill. I could get people to bring up what I want. to bring up myself. Somehow you have to bring up

the conversation so that she brings up the conversation. You know what I'm saying? Yeah, I know exactly what you're saying. Yeah, you need to... It's difficult. It's not if you get the right lead-in. If you wait for the right moment and you wait for that right lead-in,

it's not difficult. It winds up all working out. It really does, because I've done it before. So you just have to wait for that right lead-in and you have to be smart. Because you know where you're going. You know where you're going. you want that conversation to end. It's just a matter of getting the perfect start. Do you understand?

Once you have the perfect start and you have the ending, it's like writing a book. Like I wrote a book and I wrote all the middle first and then it was like the hardest parts were like the ending and the beginning, you know, but if you know your ending, all you really need is your beginning. Everything in the middle will be easy in that scenario. And because you know what? You can't know the beginning, I mean the middle because your middle is going to change depending on what she says. You just need that lead in thing to start the conversation and then feel her out and see how far you could take it. And you'll know she'll react. You guys are really close. She's very comfortable with you. She'll tell you exactly what she's fucking thinking, right? So you'll be able to gauge her

and see how far you could take it. And hopefully she'll be into it and you guys, and let me tell you something about her. If she is into it, she might feel the same way you do, where she might be afraid, and this is where you're really going to have to read into her, you know, but you know her well, so you should be able to read into her. She might be afraid to be like, oh, yeah, I fantasize about that all the time. I'd love to fuck another guy

in front of you. Like, she might be, feel freaked out to admit that to you, as much as you're, you know, freaked out to admit it to her. So she might teeter as well. Don't you think? You know, because even if that's something that she wants, she'd be

afraid that you, wouldn't be into it. Do you understand? So it would have to be something that would come up where you guys would both be pretending like, oh, I wonder if this is something that we would like. And then, you know, the minute you invite that guy over, you guys are like so horny. And it's obvious that she was always wanting it too. Because you don't know what's in her little head. You didn't know she was into bondage and all this shit. God knows where that bondage story is going to take you. How do you know what else she's into, right? I mean, this is just something that came up in the middle, like, you know, throughout your relationship?

Yeah. Yeah, you don't know because so many people like you, like you say, oh, I do this thing and I go online and, you know, and you feel like you're, you know, confessing something that's so bizarre. I think so many people do stuff like that. So many people have crazy fantasies in their head. A lot of people call into my show and I lead double lives where they're doing a lot more crazy stuff than what you've done or the similar, you know.

And everyone thinks they're the only one. but a lot of people are that way. You know, and you might have wound up with the woman who has the same sort of fantasies. You don't know where her bondage things takes her. And hopefully she's into that, but you'd have to lead into it and it will probably go slowly.

Because like I said, I think she, if she's into it, she wouldn't cop to it either as quickly as you do. Like, you know, in the same way that you guys will both be pretending that maybe it's something. But if she acts like maybe she's into it, I'm going to tell you that that's something

that if somebody says, says maybe they're into, it's something they're really fucking into. Because you know this. No, because you know those things. I don't think those things come up out of nowhere. Like you said you started in college, right? Yeah. But like, was it something that you always sort of fantasized about when you were like

jerking off growing up or something? Or did it just out of nowhere come up into your head? I'm not exactly sure. Like how it all started. But it just like kind of slowly came up inside of the, my head and then my start like I just decided that I wanted to do it so I started looking for it online right and for you to take it there that was like a strong

urge from you that I just think that those things don't just come up out of completely nowhere you know what I mean so like I said if she seems like she'd be open to it to that means that she is really into it as well and you guys are going to have a lot of fun together hopefully you know you sniffed out somebody that is more similar to you than you imagine you just don't know but you can't

you can't just go in and be direct with it you have to go in and you know that sort of tiptoe into the scenario and see if she'll do it and in the meantime keep going on Craigslist and jerking off and living your fantasy out that way okay that sounds good yeah and keep me posted I love when people call me back or they email

me and shit went down in one way or another you know when you do have that conversation or things come up or somehow or you wind up having a couple or whatever like let me know and we'll have you back on the show and we'll discuss that because i like to see how things happen down the line because i think you're getting do you feel like you're getting to a breaking point where you need for to have like you really want to have this conversation yeah i think i'm getting to the point where it's like i want to have these conversations but like you said i have to wait for the right moment to bring the back yeah that's why get your rocks off online as much as possible so that sexual tension doesn't build up and you sabotage and blurt it out or something. Do you know what I mean? Don't be stupid. Yeah. Keep jerking off. Keep going on Craigslist. Keep living it out in your mind so that you could have the patience to wait for the right time to bring it up so you don't ruin your relationship over this little thing that you want to do on the side. That's like, you know, because it's not worth

losing your good relationship for it. But hopefully she'll be into it and you'll find that time and it'll just add to your relationship. Okay, it sounds good. Okay, Jay, so keep me posted and let me know how it goes. If anything ever happened. Okay, talk to you soon. Bye. Thanks for calling in.

Okay, I just want to tell you before you go that my book, it's called Strictly Anonymous Confession, Secret Sex Lives of Total Strangers, is now available not only in paperback and ebook, but you can pre-order the 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.

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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. Do you have a story, lifestyle, or situation you can't talk about to anyone, to anyone? Or do you just want to let your freak flag fly and be on the show? Well, Strictly Anonymous wants to hear from you. Send us an email, Strictly Anonymous Podcast at gmail.com, with your story and your anonymous name. And remember, everything is strictly anonymous. Strictly anonymous.