Strictly Anonymous Confessions - 1497 - Jason Is Into Very Anal Play & Wants to Hook up with a Guy But He’s Not Into Guys?!
Episode Date: June 24, 2026Jason is very into anal action and wants to hook up with a guy but he’s not into guys and he called in to talk all about it. Tune in to hear all the details including when he realized he was into an...al action, the first relationship he had and what the girl did to him that got him totally into anal sex, the type of porn he went looking for afterwards, the different toys he bought and what he did with them, the toys he enjoyed and the ones he didn’t enjoy and why, the one big toy he bought an how long it took him to “take” the whole thing, how he felt about his sexuality after he started getting into anal on himself, when he started thinking of actually hooking up with a guy and how he feels about guys, how and why he’s also down for a women pegging him, how and why he hasn’t met up with a guy in person yet l, why he hasn’t told any of his new girlfriends he’s into anal play, the places and apps he can go on to hook up with guys, how he can bring ups the fact that he’s into pegging and wants a new girl to do anal play with him plus a whole lot more. 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 or Pre-order audiobook version here To see HOT pics of ELIZABETH plus my other 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! 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 strictlyanonymouspodcast@gmail.com 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: VB.HEALTH - To get 10% off DRIVE BOOST by VB Health, use code: STRICTLY Shamelesscare.com - Use code STRICTLY for $15 of all products https://beduc.at/pd2622-anonymous Click here to take the quiz and get your personalized roadmap to sexual happiness https://bluechew.com — Buy 2 months of Bluechew GOLD and get the third month FREE! Use code: STRICTLYANON https://Rythm.Health/STRICTLYANON for 15% OFF your first month PLUS FREE shipping 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
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Jason. I enjoyed talking to Jason. He's a young guy. He's 32 and he, like a lot of my guys on
my show, is a guy that's, you know, into chicks, but he also realized at some point that he was
kind of into guys. He's into like getting fucked in the ass by a guy. And he talks about like
his progression and how he got into that. He wasn't like when he was younger, he always knew.
and he's still a little confused about some things, and we talk through his confusion,
as well as like we talk a lot about what his next steps are, because he's definitely like,
realize he's into anal action.
He just hasn't taken that next step of being with a guy.
I, of course, tell him all the things I've learned on my show.
So if you're a guy like him and looking to take the next step, you'll get a lot of tips for me,
but by no means that I want to push him in any direction.
So we really sussed out so many different ways that he could live out his fantasy or not live out his fantasy or be with a girl and have her peg him.
That's something that he's into too.
And he just talks about the whole progression of how he got into guys, how he got into the anal action, what he's done by himself, because that's really where he's experienced anal sex is solo.
And he talks about all the toys he bought and all of his experiences with all of his toys, as well as a girl.
girl that he met early on. That's a big part of his story, who is the one who got him really
into anal play. She was the gateway drug into this whole thing that he's into now. And he's at this
place in his life where he doesn't know what his next steps are. It's super interesting. Maybe
you'll have some ideas for him. If so, post comments in Spotify. But if you post comments on
in Spotify, you've got to keep them clean because I can't post them if they're not. Or Spotify will
hide them. But anyway, I'm going to get right to be right back on with Jason.
is the strictly anonymous podcast.
Strictly Anonymous Podcast.
Oh, hey, Jason.
Welcome to the Strictly Anonymous Podcast.
How are you today?
I'm good.
How are you?
Good.
Listen, Jason, you're one of those guys that, like, you know,
you're into hooking up with guys sometimes,
but you're not into guys.
Yep.
So, just for the record, I'm actually,
I've never actually hooked up with a guy before.
Okay.
That's kind of interesting.
That's okay.
I don't mind.
Listen, a lot of times people think,
I just need so much sex in an episode or I won't air it.
I post seven episodes a week.
So I'm fine to have episodes that are tamers, ones that are more explicit.
You know what I mean?
Because I feel like every different story is relatable for a different reason.
I'm sure there's a lot of guys like you who are obsessed with sucking dick and haven't done it yet
and aren't into guys, but they're thinking about it.
Is that how you define yourself?
I don't know.
Yeah.
Yeah, of course.
And I think there's a part of me right now.
It's so everything is, I wouldn't say fresh.
the thought's been on my mind for a long time.
But I guess just having the opportunity to do it and without really going out of my way.
I mean, like I said, I'm not walking around, like, attracted to men.
Like, I don't walk out in public and, like, point out a guy that I'm, like, attracted to at all.
It's a weird thing, right?
And then I just, I guess I, when I do get, like, you know, horny or something or I'm watching porn or, you know, my mind could
go other places than where it's been for, you know, three quarters of my life, you know,
I'm like, I've always been with women. And then, then, you know, as I got older, I've had women,
you know, kind of, you know, play with my ass and, like, do things that are just different.
And that takes my mind to different places. But then it led to, it just got deeper and deeper.
And then all of a sudden, you know, I was watching, you know, really, you know, BDSM,
porn and just like, you know, watching guys get pegged and like, oh, you know, I wonder what a
deal to it feels like. And I wonder. Yeah. And then, and then it just led one thing to a led to another.
And, you know, I played with myself. But yeah, I've never actually hooked up with a guy.
That's okay. But we're going to get that whole story that you just told me in one minute would
fully drawn out. Like how like each thing that led to another and each experience you had and all that
kind of good stuff. Right? Because like I said, you were very not alone. I do have a lot of guys on
the other side of where you're at, where they had all those experiences you're having now,
and they eventually wound up sucking a guy's dick. You know what I mean? You might be there. I don't
know, you know, but I think that there's probably a lot of people like you still out there. The
truth is a lot of guys have this thing where sometimes when they're in the mood or they're horny,
they're like, might want to suck a dick, but they're not into guys. And it can be like super
confusing. It used to confuse me until I had Dr. Joe Cort on who talked about how there's
sexual orientation and that's like, you know, who you're attracted to when it comes to sex. And then
there's erotic orientation, which is, you know, your erotic orientation is like what you're into and what
you'll be down for like when you're in the fucking mood. It doesn't mean anything more than that. You know
what I mean? So your erotic orientation is, yeah, when you're horny, you like dick, but you don't like it
any other time. So you wouldn't consider yourself bisexual or anything like that. Right. Right?
Yeah, I would say that's pretty small.
on. But what was the gateway drug?
Was it like your girl playing with your
ass or was, were you thinking about Dick
way before that?
Well, I guess like
growing up, I don't
know, not in a sexual way, but like
you know, the
guys at a young age
were, you know, fairly open, you know,
changing in the locker room and stuff. And I never
had those thoughts then. Like it was
just like it's
that's why I guess I explain that.
Those thoughts never popped up then.
But like the thought of, you know, having anal sex was always on my mind since I lost my virginity.
And once I had got the opportunity to do that, I've had girls like, let me, you know, eat their ass from behind and stuff.
And that was always really hot to me.
And it took a long time, you know, to find someone willing.
And I finally had anal sex and I kind of loved it.
And that kind of led to me kind of pushing more towards a girl kind of, you know,
going down and eating my ass. And I had a girlfriend at the time who was really willing. And
we had great sucks all the time. And that was part of it. Like I would get head. She would lick my
ass and kind of, you know, stick her tongue in there. Okay. But wait, I'm still want to be before this
girlfriend. Okay. I need to go back to like when you started thinking about Dick. You said it wasn't in
the locker rooms when you were younger or anything like that. I think it's like what you
might have said, which is the first time you lost your virginity you were thinking about.
anal sex. But do you mean anal sex with girls or anal sex for you? I don't know. No. No. And that's why I
explain the girlfriend. Like, and that's why I said like nothing throughout high school. Okay.
And then my that first relationship where like I was open to having like my ass played with and like
she was open to that's what kind of led into me watching like anal porn and and and you know,
after we had split up and stuff and like I said, we had great sex and. And,
That kind of, you know, I had freelance and hooked up with random women at the time,
but I was watching porn too.
And I was starting to watch, you know, BDSM porn and just like, you know, like I said,
guys getting pegged and stuff and I don't even, it led to that.
I have no idea why.
Well, how far.
Okay, let's go back to the girlfriend.
So first she's blowing you and then she's going down like on you in your ass area,
right?
while you're with her. Did you, did she ever start pegging you or put stuff inside of you? Like,
how far did you go? No, she would put, she would, you know, kind of stick her tongue in there. And she had,
you know, she stuck a finger, you know, kind of, you know, I wouldn't even consider it full penetration.
You know, she, you know, played with my ass with her finger and stuff. And that was pretty much it.
You know, I wouldn't say she fingered my ass. Okay, but I will tell you as a someone who has the same body part as you do.
So this is the place where like men and women can.
late, even though you're a guy. I know exactly what that feels like because I'm a girl,
right? And I have the same exact thing going on. Okay. I might not have a prostate, but I have all the
nerves that you have. So I could see how and why if you were open enough to allow a girl to do something
or she was pushy enough to get you to be open to her doing it, that it would make you want it more
because it is a very extremely sensitive part of someone's body. And what a lot of guys don't know that
haven't sort of gone to that area is how sensitive and amazing it is, right? So I think it kind of
makes sense if she was like doing all the stuff to you in the heat of passion and you were feeling,
you know, your nerves were being stimulated because you were, you know, okay with it and you
were able to receive it. That of course you'd kind of want more because it felt really good, right?
Of course. It was, it was an, it was a curveball experience. But one like, one like I just was,
I was definitely okay with.
And I actually can vividly remember, like, getting ready to go to work one time and her giving me head and her licking my ass.
And, I mean, I'm to the point to where, you know, I was literally about to come.
And she wasn't even touching my dick at all.
She was, and my brain told me, like, I don't know why it was just my reaction.
I stopped her.
But I was about to come just from her.
So I can vividly remember the first time I was about to come from like my ass being touched.
Yeah, yeah.
You know, and I kind of, I stopped the moment.
But yeah, anyway, that that moment never left my brain either.
So like after that, like I said, it kind of just, that's those, you know, we spent quite a, I guess a year and a half, two years together of having great sex.
So after that, it was, that's kind of what led into the porn watching and the being curious about more.
know something about more.
Of course.
That makes sense.
You were so close that you're like even more of this would be better.
I mean, I think that that's kind of natural, don't you think?
I mean, you did kind of tell the story like one thing progressed to another and then to another.
And I think that that's typically how it works.
And I'm going to tell you that's the reason I personally think that a lot of guys are afraid
to go and go to that area of their body because they're so afraid that if they do,
the next thing you know, there's going to be a dick in their ass.
But I don't think that's always the case.
I mean, you are a guy who never thought about dick, right, at all.
But like once that area started to be stimulated,
and now you know that you like it.
Now you kind of are thinking of the real thing.
But that doesn't necessarily happen to everybody.
You know, we're going to get your whole progression.
But in the beginning, it was just you were, you were like looking not at porn of guys fucking guys in the ass.
You were looking at porn of like women pegging guys in the ass, correct?
Yeah, yeah, that's where it started.
Yeah.
Yeah, for sure.
Yeah.
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And that, honestly, I guess that came after, I guess I, like, I guess I did play with a
dildo and, you know, I'm like, I don't know if it's just, I listen, I don't know, it's kind of
cute. I don't know if it's because you're from the South and you just say, I know a lot and, like,
you know, that's just the way you talk.
Or you're like almost shy about what you've done.
But it's just like sometimes when you're explaining these experience,
it almost sounds like you're like kind of embarrassed to admit it.
You know what I mean?
I don't know.
Is that true?
Or am I picking up on that or is that not true?
Maybe a little, maybe.
Okay, well, what did you, you, you would, okay,
so after your girlfriend did all that and everything and you,
and you knew that, oh my God, this area is like highly stimulated, I want more.
What did you do?
Did you go out and buy something?
Did you use your, I had a guy once who used his GI Joe doll.
but I'm sure you're older than that at this point.
Like, did you use something around the house?
Like, what did you do to go further with yourself?
Oh, well, originally I used my fingers, you know.
Okay, okay.
You know, that was the start.
But I went and bought a butt plug and then...
That's smart.
That's a smart move.
Yeah, I bought a plug and then the extreme side of me was like, well, if I like it,
I would really want like a, you know, something larger around.
So I bought a plug in a bigger-sized dildo my first time, you know, buying anything.
And, yeah, went home and I, you know, kind of put the plug in and I walked around.
And just let it hang out in there for a little while just to see, you know.
And how was it for you?
To me, it felt great in a sense.
But it wasn't like arousing once it was in there.
Like there was nothing about it.
If it wasn't moving, you mean, was it a lot of it?
vibrating plug or was it no okay no it was just the it was it was not it was a glass one it was nice but
like i said it felt good but it just wasn't arousing to the like that it going in wasn't coming out
and that like turned me on of course but just sitting there walking around with it wasn't a true
yeah sitting there like the extreme side of me wanted to feel more like right away yeah okay
so listen you knew you wanted to go a little further because you already you had bought your
second step.
Yeah, I think my mind was already there.
Yeah, you knew.
You were, you were ready.
Okay, so then what happens?
I used the Dildo and it was
extremely intimidating and
I think, you know, I was like,
man, I might be in for a little more than I
expected. Well, how big was
it? Did you, maybe about a too big
like, maybe it was too big.
Yeah, it was, it was 10 inches, but I
I didn't expect to use the whole thing.
It was just.
Oh, my God.
Guys are crazy.
Wait a second.
What was the width, too?
How many inches around?
Do you remember?
Honestly, I'd have to go back and look or something.
What was it?
Thick?
Yes, of course.
Yeah, it was huge.
And yeah, I should have known better.
But like I said, I didn't expect to, like, you know, use the whole thing on myself right
away.
It was, you know, I didn't.
want to buy one too small and not be satisfied and like oh well i need a bigger one well that's a
problem when you're searching for sex toys when you're horny did you go buy those things when you were horny
i feel like every time i talk about this and you know and have these thoughts i'm horny so yeah oh sorry
i hope you're not going to be jerking off while we're talking no i was walking around the store
i'm sure i was extremely horny yeah that's the problem it's like impulse buying you know what i mean
that's why you picked the huge one.
I've done that before, trust me.
Okay, so did you wind up getting it in?
And how was it?
I did in a few inches.
And it was, I really liked it a lot.
Right.
Yeah, I'm sure it was like overwhelming, powerful.
Yeah, very overwhelming.
And honestly, it was overwhelming to the point.
Like, I couldn't, I couldn't really, like, jerk off, like, do anything.
Like, I wanted the calm.
I just jerked off after.
Okay.
Okay. Okay. But yeah, it was. It was overwhelming and intimidating. And I remember, you know, kind of feeling a little sore after. I was like, wow, okay. I just did it.
That thing was a little bigger than I expected. Okay. So how did you progress?
I guess I do have just an extreme side. I mean, like the next time I did it, I just, I was like, I'm going to go for it. And, you know, took as much of it as I could and was, you know, looped up as much as I could.
Yeah, I went all in and I remember.
I was like, I don't know how this thing is so far.
Yeah, I loved it.
I was like, wow, it was like the first time.
I just didn't expect that.
It felt great.
Did you come from like it without like touching yourself at the same time with just that?
Like, do you think you were hitting your prostate and were able to orgasm from it or no?
No, I don't think I was because.
again, it was, I think the times I've gone that extreme, I think, I think with the right
toy and, you know, I'm in the right angle for sure, I would. But it was, I was like how,
I remember being in a certain position and I was like, this thing doesn't not want to go,
go in me. But being positioned a certain way, it felt a lot better. And it would, it would go
and really far and felt great.
So I was like, okay, I just settled where I was comfortable.
I wasn't.
But, yeah, I don't know exactly how much of it I took, but, I mean, yeah, I definitely
pretty much most of it.
I mean, so I was, like I said, it was overwhelming.
And one of those situations I came afterwards.
And, yeah, I don't even know why, like, I haven't came.
Come.
Yeah, I have, I haven't.
it come while doing it.
A lot of people don't, if you're not
playing with yourself at the same time. I think you have
to be hitting your prostate
at the same time. And that's
like a, you know, it's a matter of like kind of
finding that. But let me ask you
this. You know,
you know, here you are a guy who
had never looked at guys before. You still don't
even look at guys and you're into them. And you just had
like a dick at 11 inches
inside of you. Okay. Like, is
there any kind of post nut clarity?
Like, what the fuck am I doing?
weird feelings about weird feelings about it at this point after you're doing this kind of stuff
secretly or are you totally cool with it?
I feel like I'd be lying if I said no, but it wasn't like something that you were going
to stop because of how you felt bother me either.
Yeah.
I don't think.
I just I don't know.
Like I've maybe the more of the question is like did it start to make you question your
sexuality at all?
Do you ever think like, oh, do you ever think like, oh, do you?
Maybe I do like guys out of it.
What is this about?
Or were you like clear with yourself?
Of course those questions popped up.
But the sure side of me is, I'm like, again, I don't wake up and look at another guy and think like, oh, I would suck his dick or I'd let him fuck me.
Right.
But is that confusing?
I would think that might be a little confusing to someone.
That's what I'm wondering.
Yeah.
I feel like somebody would be extremely confused.
I can't say I'm not confused.
there's and I think that's why that's why I've dove into like like I said I've watched like
guys being pegged and stuff and I'm you know you know a girl who would like dom another guy
potential situation I feel like maybe might be better this is also fresh for me kind of so it
was you know these are all feelings that are new and I'm I'm open my own open minded person but again
I guess there is a side of me that I feel like I would
I would suck a dick and I would let a guy fuck me
but I don't think I would just go out searching for it
and I again I don't I've never once I can't
I never want to have been in public and been like oh that guy is
attractive I would definitely blow me like that
No but that's how all the guys are that are into this kind of play
It's really when they're in the mood and they're horny and it's like in the moment, that's when they think of these kinds of things, right?
It's like a hot thing.
It's like dirty.
It is whatever it is.
You know what I mean?
And that's where it stays.
It's in that box and it doesn't.
But you don't think about it in, you know, your regular life, right?
And I think that's a difference between truly bisexual people who are into both men and women, fluid people who would be with anyone.
and guys and maybe even girls that have this too, like you.
Right.
You know, maybe, I don't know.
Maybe you're going to call me up a year from now,
and you are understanding that you're bisexual.
I don't know.
You know, I mean, I feel like it could go many different ways.
But we're not at the point yet in your story
where you start to even really think that you're going to suck a dick, right?
When you're, like, using this thing for the first time, correct?
I think so.
I think when I was interested in, like, you know,
the thought of like you know a big gildo and like using it often and again not it turned
into like okay like the extreme side of me is like what what's next you know well it could either
be a woman pegging me or a guy fucking me and i'm open to either or but you know and i i've uh
i've been into you know the thought of maybe finding a woman that finding one you know or
trying to, you know, go that route was, I don't even know where to begin, but finding a woman who
I would be interested in a dynamic with somebody who, a woman who was like, oh, okay, I'll fuck you
here and there, you know, and you do this for me or whatever. I, I don't know. You just want to be
fucked in the ass by somebody. Yeah, I guess. And that's what I was getting. I think the whole
fascination just comes from being fucked in my ass and you know kind of you know I'd be
extreme side like I said I kind of wanted a big deal to there's a what's next after this
and not you know wasn't satisfied with the first now it's let's move on to something bigger
and you know then I was watching BDSM porn so there's a there's a side of me that's like
oh well I would be open to a dynamic where a girl was like Dom and me or you know
stuff like that.
Like I said,
it's so fresh for me.
But yeah,
I don't,
I don't know.
Well,
how fresh is all this?
I mean,
so you just have
that one dildo and that one thing
and that's it?
Have you blown other?
No,
okay,
let's keep going on.
So that,
all those thoughts had started
and I was playing with toys
and I bought an inflatable dildo
and went to the extreme.
What does that mean?
How did those work?
Explain it.
Oh,
an inflatable?
Yeah,
I've never had one.
You blow them up,
I guess.
Boil them?
But you blow them up.
Oh, blow them.
Sorry.
Blow them up, literally.
I was like, oh, what do you put them in hot water and they expand?
I don't know.
There's a hand pump.
So you just pump this little ball and it blows air into it.
Oh, okay.
But it doesn't say hard or is it like a balloon?
I don't get it.
Yeah, I guess it inflates like a balloon.
Yeah, I guess.
The inside.
But I mean, the outside is hard like a dildo, right?
Like it's not like, yes.
Oh, okay, cool.
So you got an inflatable one because you wanted to see how far you could push it.
Yeah, like I said, the extreme side of me wanted to go further and bigger.
And so I played with that and again and had an enjoyable time.
And so I was like, okay, you know, what my thoughts were always running.
And I'm like, well, I found a, it was like a massage parlor that was like they were dressed.
nice and stuff like that, you know, attractive and all that. And it was just being in there,
like, turn me on. Like, I just was like, oh, my, like, it feel like everything I do, I turn around.
I'm like, these girls, I'm like, I could only think about, like, one of them fucking me or like,
you know, take, take advantage of me in the moment while I was there. And so these thoughts just never,
they would just like never leave. They would always pop up somehow. And even, even in a daily life,
they would end up popping up somehow if I could watch, you know, straight porn with a woman and a man.
And somehow, I mean, it would still, like, cross my mind.
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What would?
Always the thought of you being anally penetrated.
That's what you're talking about here, correct?
Like when you're on the massage table and the woman's, you're not thinking of like making out
with her and going down on her.
You're thinking of this woman, which it didn't happen.
But as she's playing with, like massaging you, you're getting horny thinking that
she's going to dominate you and peg you in the ass is what you're saying.
Yeah.
And I would, I wouldn't.
say no uh i i i do love eating pussy and i do i do love getting fed and like okay you know fucking
women and so those thoughts still come you know come up but uh obviously like my whole life
and i've just started thinking about this stuff so those are those are popping up too and and
they're more relevant because they're so new in my brain but yeah they would just pop up every
day i could see a woman out in public and i'd like what but i'd still see women i'm like wow she's
she's super hot.
But you're not though ever walking around seeing guys and thinking, oh, I wish that guy would
fuck me in the ass.
But you are thinking that about women when you're walking around.
Yeah.
Yeah.
Yeah.
That's not a definite, yes.
Yeah.
No, I'm trying to make sure I'm telling you the truth here.
Yeah, I love that.
I feel like it's a good therapy session for you.
You're getting the truth about yourself right now.
I don't know.
I can honestly say I've never.
I've never had those thoughts.
It's always been like, and even if it was a girl I could see myself with, I would, I would
in a way be like, yeah, I could see myself with her.
And then those thoughts were so fresh, they would pop up like, well, yeah, well, I'd let her peg me too or something, you know.
Yeah, but never with the guy.
My whole point is the guy.
You're never thinking about it with guys when you're walking around still.
Even though at this point in your life, and we're working up to this place, is that right now, you would be okay and down.
and interested in hooking up with a guy?
I don't, I guess define hooking out.
I don't know.
Let's get to there.
Because you told me like 10 times I felt like that you would be open to a guy
fucking you in the ass.
You'd like to suck a dick.
I feel like you did tell me that.
But it's okay.
Let's keep going.
So you buy the inflatable thing.
And then what?
Do you ever get a girl to fuck you in the ass or no, never?
I never have, no.
Okay.
Have you had any girlfriend since that one that you had great sex with?
Yes.
Okay, and did you bring, did they do stuff to you as well?
Did you talk to them about this thing that you're into like on the anal play?
No, I know I always just kept it to myself.
Really?
You don't tell the girl?
No, I've never told them.
Right.
I could see why I think a lot of guys hold that kind of stuff, they don't open up about it.
I mean, my show, I'm always like promoting it and it's like I don't understand why it has such a stigma, you know, for real, but it does.
And a lot of guys do keep that to themselves, right?
So you don't push them to play with your asshole or anything like that.
No, but if they're willing, I'm obviously not denying it.
Of course, but you haven't got anyone willing except that first girl.
Yes.
Okay.
So how many toys do you have now?
Where do you go from the inflatable?
Then what do you do?
Did you ever get one that you stick on your wall?
I have one of those.
That was the 10-inch one.
That was the big one.
Oh, okay.
I have that one and the inflatable.
And I don't know why.
I just was interested.
and it just my brain goes to places.
And I had a, a chastity cage just to try it on.
And I was like, this is the most uncomfortable thing in the world.
I don't know why anybody would ever wear this.
But I don't know.
I think you have to get the real expensive ones for it to be good.
Yeah, right.
Yeah, I did buy a cheap one.
Yeah.
So, and I'm sure under different circumstances, it would have made sense.
But anyway, yeah, just the,
inflatable in that big dildo.
Let me ask you this.
Have you ever put any of those in your mouth while you're like having fun by yourself?
The dildos?
Yeah.
No.
Okay.
Okay.
But you would be down to suck a dick or no?
I think so.
And I think the thought of like, I think the thought of doing that before I was fucked by,
it would turn me on.
Yeah.
But I don't know why.
I don't know.
Yeah.
I would.
Yeah.
I would be down to suck it the one that the one that's fucking me for sure yeah
can I ask you why you know now that you're so activated and into this and this is on your
mind you're not currently dating anyone correct are you single okay so you're single you
wouldn't be cheap how old are you by the way you son yeah I'm 32 okay you're 32 you know what has
stopped you from fulfilling your fantasy because it does sound like kind of a fantasy like where
you at with living out your fantasy in real life?
I guess like I said, where to start?
I mean, oh my God.
Let me just tell you something.
When the object of your sort of sexual fantasy, when the object of your sexual fantasy is a male
versus a female, it's a lot easier to make that happen.
You don't understand because you've never hooked up with men.
Okay.
But like, it's a lot harder for you to just like in two seconds find a strange girl.
to come over your house and peg you, then it is a guy, a strange guy, okay?
That can happen in two fucking seconds.
Have you ever heard of sniffies?
I'm obsessed with sniffies.
I don't know.
Someone called into my show.
I mean, just listen to all these guys' episodes that are one step further from you.
I mean, it's pretty easy if you really wanted to, okay, to find a guy to hook up with.
They're not, you know, they roll very different than women.
You know, most, I'm not a woman that's going to go online and just like go and fuck a stranger for
no reason. But like I always tell my guy friends, my straight guy friends, like, you'd be a lot happier
if you were into dudes because dudes will just fuck other dudes like without even knowing them. You
don't even need to know the name. They'll just meet them. They could hook up and see you later.
You know what I mean? Like that kind of shit is a lot easier to make happen than, you know,
hook it up with chicks, no strings attached. You do know that, right? No, obviously.
No? Well, let me ask you this. If five of your girlfriends, do you have any girls that are your
friends. Do you have any girls? Like, do you have any girls are your friends? I live in extremely
quiet life. Okay, let's pretend you had some girls that were your friends. If each one of them
called you have to come over and fuck them, would you say no or would you say yeah? Oh, I would. Yeah. Well,
if I had five guy friends and they all called me up and said, hey, do you want to come over and
fuck me? I'd say no to every one of them. Okay. That's the difference between men and women. Okay.
That's right there. That's the difference. Just as much as you just like, fuck any girl that wanted to,
right? That's how horny you are and that's how easy it is for you to like get hard and fuck a girl
is the way guys, all guys are. Girls aren't wired that way. Some are, okay, I've had them on my show.
Those are my favorite girls or the extreme girls. You know, they're like wired more like guys,
but like typically girls are not like that, you know, but guys are. So it's very easy to set up
a situation where you just like hook somebody up. But listen, sometimes, and I got to find out if you're
this way, sometimes guys are more wired like girls. Like they don't really.
feel like they could meet a stranger and get turned on.
Like they're a little bit more, what's that word, demisexual.
Like they kind of have to like like somebody to feel turned on by them.
You know, maybe that's stopping you?
Or is it just like you feel like shy about meeting a stranger and hooking up with them?
Like what's stopping you from going further?
Because it's definitely not the availability, okay?
You're a young 32 year old virgin, straight guy, okay?
you could get any guy to come over at your house and fuck you just so you know I guess the effort
I don't know maybe I the effort you just said you live a quiet life you have no friends what do you
do what are you doing all day long I just work and jerk off I mean half the time that you're using
Googling porn you can go on to like you can go on to Tinder you know or grinder grinder why wouldn't
you do you know about Grindr?
Yeah.
Okay.
What keeps you from going on Grindr?
I don't know.
Are you shy?
Yeah, I guess maybe.
I mean, because I understand that.
You know what I mean?
Like, even if I was like really horny for a situation, you know, I don't know that I would meet a stranger.
And it's not just because I'm not wired that way, but it's also because like I don't know that I'd ever cross that line.
Maybe I'm a little shy in that sense or whatever.
I admire people that just do shit and don't think about it.
You know what I mean?
Are you someone that thinks a lot?
Because I know I do.
Of course.
Well, not everybody does, you know what I mean?
But I'm an overthinker, so I understand an overthinker.
And overthinkers tend to be a lot more cautious than under thinkers.
Do you know what I do?
I do.
I do overthink.
Yeah, me too.
So we're less fun, I think, because we overthink.
I always admire people that don't think so much.
You know what I mean?
And I'm also, like, completely comfortable just hanging out inside, not going anywhere.
Right.
So I guess that doesn't help.
No, but let me ask you.
like do you feel like this itch that you want scratched is so strong that you will probably wind
up doing it or do you feel like you'd be totally fine never experiencing it like where are you
at with that i guess there's a part of me that that is a questioning like oh well
because because i'm going to have to pursue it in some way you know like i said i'm completely
content just living a normal life, but I do have these crazy desires that came out of nowhere.
I feel like there's a part of me that would be fine.
That's why I say it's confusing.
It would, am I like, am I gay?
I guess.
I don't know.
So you might be more than a guy that's just into guys.
Like you might actually be into guys a little bit more than you think.
well like I said I think I would just I'd be comfortable not experiencing it at all there's a part of me that would be completely fine and then but I do have these desires but like I don't know I guess there's a if you I've never thought that from that perspective so I I feel like yeah I would be fine if I didn't experience it but and I would the thoughts go away yeah I guess if if I just knew deep down I wasn't going to
going to pursue it, then yeah, I guess I would probably, I probably would just stop thinking about it,
you know? But your thoughts of that maybe you will pursue it is what keeps it kind of like hot to
you? Is that right? Yeah. Yeah, there's a part of me that's like, oh, well, I want to experience it,
and I think I probably will. So it just doesn't go away. But there's, I guess you asking me that,
you know, yeah, I think I could just be okay, content. And I just wouldn't think about it anymore.
But that I don't like have to.
There's nothing forcing me to just not pursue it or not think about it right now.
So that's why I am.
But yeah, it's not like something I'm like so crazy about.
I have to try it.
Yeah.
Right.
But it is kind of new.
And over time, it could get to the point where you want, you have, you really want to
experience it a little bit more than you do now.
You don't know.
But, you know, and I hate to be a pusher because I don't want to corrupt your life or
anything.
But I will also tell you that there are like places where you could go like a,
adult theaters and adult bookstores where you could just like, you know, suck a dick in a
glory hole with no one even knowing or seeing you. You don't have to do anything. You don't even
have to talk to them or put out an ad or anything. I mean, these are things. Like I said,
I don't want to be a pusher and make you two things. But like these are recommendations.
There's grinder. There's sniffies. You could turn that shit on and see where people are
hooking up in your neighborhood and you just show up and hook up. I mean, you don't have to put so much
time into meeting a guy if you don't want to.
You know,
maybe one day in your,
when you're horny,
maybe you'll wind up just going on Grindr
and setting up a profile and just seeing what comes your way
without any maybe commitment.
Like what stops you from like going on Grindr?
I just never, I don't know.
Really, I guess Grindr is something.
I really haven't.
I've heard of it, but I'm not real familiar with it.
but like I've heard of tender.
Yeah, it's like a guy's hit up.
It's like a guy's hookup site.
Oh, okay.
Yeah.
I'm not familiar with,
with Grindr.
Yeah.
Is it better maybe option for you to find a girl that would peg you and have that be in
your world so you could like date that person or something?
Or are you still trying to figure out maybe if you would be into guys a little bit more?
I mean,
because now you,
before you just said maybe you're gay.
So you're confusing me.
As much as you're confused,
I'm confused now too a little bit.
No, I said, I said that's why when I said that there's a, that's why the side of me says I'm
like not gay, but maybe somebody else would say I'm gay.
I don't know.
No, you know, you would know, okay?
You'll, you know.
And you might not know until you do it.
No, I'm like, like seriously, you might have, like, I remember the first time I hooked up
with a girl and that's when I realized, okay, like, I'm definitely not into women in that way.
You know what I mean?
Because I tried it.
But, you know, like, so sometimes you have to like, sort of.
sort of go there to even know.
And that would maybe cure up the 1% doubt in your mind.
You know what I'm saying?
Like it might actually clear the air and say, okay, you know what?
Yeah, I'm definitely not gay.
Or, okay, you might say, okay, you know what?
Maybe I am more fluid than I thought.
Maybe I'm not gay, but maybe like I really am into men as much as I am women.
You don't know.
You know what I mean?
This is all new to you.
Yeah.
You're right.
I guess.
I don't know what, but you, you ask the casual person and they're going to say, you know,
you're gay for thinking it.
Well, I don't talk.
I'm not, I mean, casual, I call that maybe average, you know, is that an average person
thinks that the vanilla world?
I mean, but that's like ridiculous.
Just because you're thinking about hooking up with a guy that means you're gay, that there's
so much between straight and gay that exist, you know what I mean?
Those are two opposite ends of the spectrum and both are completely fine.
You know what I mean?
whether you're gay or straight, you're totally great.
But there's a lot in between gay and straight that people could fall into.
You know, nowadays, I mean, you know, if you were born 10 years later, okay, and you were like 23,
you would be fucking bisexual.
You'd be fluid.
You wouldn't even be questioned it.
You'd be like, I just like whatever, you know what I mean?
Like, that's how all the young people are.
I have a 10-year-old son.
Every show we watch, including Disney.
Everyone's dating everybody.
Nobody cares.
There's no, like, there's no difference, you know?
at all in kind of like who somebody is into.
It's a very different world.
But, you know, I don't think it started as early as your generation.
I think it's like maybe one behind you.
You know what I mean?
But, you know, you might get it cleared up if you ever wind up having that experience.
Or like, what's going on with you and girls and chicks?
Like you're single now.
Are you looking, you know, you're only 32.
You're kind of at that age where you start to think, like, do you want to get married,
have kids?
Do you want a long-term relationship?
Like, what's your deal when it comes to women?
Yeah, I think I do want I do want kids. Yeah. And so are you like dating? Are you on any apps? Like what's going on with like do you want a relationship in your like? When was when was the last time you had one? I just asked you a lot of questions. Yeah. Yeah. I've been in I guess recently I've had some random, you know, hookups and I've hung out with some some girls and that's been about the the most of it. I haven't really my last relationship was probably.
like a year ago.
And how long was that one?
That lasted for a year.
Okay.
Okay.
So that's kind of new to be out.
I mean,
it's not like you've been single five years or six years.
No.
Most of the relationships I've been in have been pretty serious.
Yeah.
And I've kind of always,
I haven't been,
I've been in three random relationships that,
that lasted a long time,
I guess, throughout my 20s.
And so,
you know,
randomly here and there I've been single and have gone on some hookups for he's yeah but that's what
you just haven't right the found the right person but it sounds like you are like typically we were all
like a certain type right like you sound like you're like a relationship type you'll eventually
want to find yourself back in another relationship because that's what's happened to you in the past right
so most likely that'll happen again whenever the timing is right you know I do suggest maybe
you know when you get a new girl you know maybe look for a girl who's a little bit
it more open-minded, like that one girl that you had that great sex with so that you could
get into a little BDSM or maybe be able to talk about your interest in anal action, you know,
with your new girl when you do find one.
Don't you think that would help or be great?
Yeah, of course.
Yeah, that would be great.
What is the reason why you don't bring it up?
You're afraid of, like, them sort of being freaked out by it?
Yeah, I guess that it would just be, I guess, I guess I've always,
just been like, oh, well, if it gets brought up and they're in, and I can read that they're into it,
you know, then, then maybe I'll kind of throw it out there, but otherwise I'll just play it safe.
Yeah, you can't, you kind of can't play it safe. Only because, and only because, listen,
I'm a girl that, like, always tried to get guys into anal play because I was like, I like it.
Why wouldn't you like it? You know what I mean? And like, but it's not like, and, you know,
some guys I would try it and most of them would be like, get the fuck away, you know? But it's not like,
even though I'm open to it that I have ever put that on the table with every guy either
because I just kind of assume that every guy isn't into it.
So you know,
you might have been sitting across from girls who would be totally down and totally fine with it.
But you just didn't know because they wouldn't bring it up because they think,
oh, this guy's straight.
He wouldn't be into that.
And you're thinking they, you know, won't be into it.
So no one's saying anything.
So you might have to feel someone out.
And you don't have to feel them out by saying,
hey, by the way, I just started thinking about
dicks up my ass and, you know,
I'd love to be with a guy and I'm wondering if you could peg me.
Like, you don't start out there, but you could be like, you know,
hey, I'm like into anal stuff and I had this.
Like, you know, I think the perfect way to bring it up to any girl
that's super okay and is the least, you know, sort of shocking
would be to talk about your previous experience.
Like you had one girl at one time that did was really into this and, you know,
asked you to try it and you did and you really liked it.
You know, I don't think that there's anything wrong with that.
Yeah.
Blame it on her.
Yeah.
You know what I'm saying?
Use her as the stunt domain.
Yeah, yeah.
Use her as like the blame.
You know, make her take all the blame.
Like, oh, when I was younger, like I had this one girl and she did this thing and I was
like, what the fucking, well, like it felt like really good.
Like I'm really into anal stuff.
Are you into it?
Like I would totally be into it if you are, you know, kind of like opening up the
conversation like that.
that is a great idea yeah yeah because listen you don't know that uh uh the the girls that you've been with
wouldn't wouldn't be okay with it a lot of girls nowadays especially even in your age range because
you're probably going to be dating someone a couple years younger even early 30s girls like there's
so much more open-minded nowadays to stuff like this it's not like you're 57 and you're dating
in that range it might be a little bit like different because those people are all fucking born at a
different time, you know what I mean? But you grew up in a much more open time. And people around your
age are much more open-minded. I think it's okay to bring up stuff like that with a girl. And, you know,
and it's not going to be a deal breaker if like if she really likes you. I think a lot of times
if guys think like a girl is just like, you know, going to hear one thing and run. Like if a girl,
especially if it's a girl that likes you and you like them, like as a girl, like if I meet a guy
finally and all the stars align and this is someone that I actually like, one. One
thing is not going to make me fucking leave him.
You know what I mean? Like, that's not going to happen.
It's different with just a hookup person.
If you're just hooking up with someone and you never met them and you throw that out
there the first time, that might be like bye if they're not into it.
But once you get into a relationship with a girl and she really likes you and you like her,
you could bring that up gently and bring up that other girl and talk about that experience
and how you liked it and see if she's into playing.
And if she's not, she'll let you know.
You know what I mean?
Of course.
I think it's a tread lightly situation.
So, but tread.
At least you're trotting.
But yeah, but yeah, it's, it's something that you can kind of nonchalantly bring up for sure.
Yeah.
Or you could just go straight ahead and go on Grindr or sniffies or go to an adult bookstore
and you could just go straight to the, you know, straight to the action.
I mean, that's your, that's your choice.
I feel like deep down you want me to.
No, no, no.
I deep down, I don't like, like, you know, as much as I seem like I love to tell everybody what to do and everything.
Like I don't like to push anyone in one direct.
Like I don't want to corrupt you and force you to go to like a glory hole and you're not like, you know, you just seem so young and innocent.
Like I don't want to be the one to, you know, sort of push you in that direction.
I'm just telling you this stuff that I've heard.
You know what I mean?
And these are the options.
I also do think you could go on Grindr.
You know, there are.
It is quicker and easier to do with a guy because with the guy, the difference with the guy and the girl is with the girl.
You're most likely going to be doing it with a girl that you like and stuff.
you have something to lose with her, right?
Because maybe she's somebody that's going to be your next girlfriend, right?
But if it's with a guy and, you know, most likely you're not gay, you're not going to care.
Like there's not going to, first of all, if you're with him, he's down.
You know what I'm saying?
He knows what you're looking for.
So there's no question that he's not into what you're into and there's no losing anything.
Do you get it?
It's a lot easier of a thing to happen.
I always make jokes that like in the gay world, like the shit that goes down with gay men is like in the straight world.
just would never happen because women are
not wired like guys
and I just think gay men have the best sex
because they're they're you know
they get to have sex with other men who think exactly
like they do. The only reason why
straight vanilla guys don't have that great of sex is
because their girls stop them.
You could find a guy in two seconds if you ever get
the balls to do it you know and
you can there's
non-committal ways to do it like I said
adult theater there's
a little bit more of a commitment
on Grindr, but you're not committed to anything even if you just make a profile. You don't have to put your face in it or anything. You know, do you live alone? Yeah. Yeah, well, you know, listen, you could have a guy this weekend if you wanted, okay? You can. And I don't know why you don't know that. Where do you live? I guess not. Now I do. Yeah. I mean, you know, how did you find my show, by the way? Like, did you find it from like one of the episodes about a guy that's into this kind of thing? Or did you find, like,
what what why listening like what drew you to my show and what episode did you listen to that got you to call in
i i can't say specifically like what episode because i've it's been a while since i first found it
but i've i've been on some random road trips and i listening to that kind of just
kind of kills the time and keep you know i've just found it on pandora scrolling for
random like sex podcast and but was it like a good
Guy on Guy podcast that caught your attention? Or was it like a Swinger or a Hot Wife one? Or is it all of them?
Or you're into any kind of stuff? Or BDSM? I had listened to the most random. I think it was a BDSM
episode. I listened to a completely random one just to see what it was about. Okay. And this has been a
long time ago at this point. And then like I said throughout the years, and it's not all the time,
but if I'm on a road trip, I'll throw an episode on and listen to it. So that's kind of
where I found I just stumbled upon it searching.
Listen, I ask that, not because I, you know,
it's more so because I'm wondering if, you know,
if you listen to a lot of the guy on guy ones,
because I do have a lot of episodes that you'd learn all this stuff that I'm telling you.
So that's why I'm thinking maybe you haven't listened to those episodes,
even though you found my podcast, you know, you were listening to other ones.
Because these, all these people talk about all this shit.
Like, you could find out how to do it exactly by listening to like 50,
episodes of guys who have been you before and then you after and you could listen to their journey
and see exactly how they got from like, you know, sort of wanting to experience it, fantasizing
about it and then living it out in reality. Yeah, no, I guess I haven't listened to. Yeah,
that's interesting. That was my point. That's what I was getting at. I was like, yeah,
it's like interesting. You found my podcast. I was assuming you found it because of the guy and guy stuff
because I'm a big promoter of like guys just being okay with it. You know what I mean?
because there's such a stigma around it and it's so stupid. Like I said, I think it's different with
the younger generation, but there is still a stigma around it and so many guys keep it to themselves
and everything. So I do have a lot of episodes on this topic. And I do suggest that, you know,
your next road trip or one hour trip someplace, you start listening to some of those. You could
search on Spotify. If you go into Spotify, that's a great app because you could search at the top of any
podcast. Like if you go to the top, there's a search bar and you could like literally put in
buy or guy on guy you know or guy he guys and you're going to find those episodes super easy i have
over almost 1500 episodes at this point and i have tons of stories of guys like you so you could
you know hear those stories and maybe they'll inspire you to do something or maybe you'll wind up
meeting a girl and you'll be get her into the stuff that you're into you know yeah you know
yeah i'll have to download the spotify i've been a pandora rat for forever well maybe they have it in
Pandora too. I don't know. But, you know, listen, I have those episodes on all the time. So even if you
just scroll back a little bit, you're going to find like five, you know, because I, that's one of
my biggest topics besides the hot wiping things and the cheating stories. You know, I have a lot of stuff on
that's like common. And like, and one of the things I always say that I've learned from my show is that a
lot of guys are into guy and guy action. It's just, they're just not copping to it. But they cop to it on
my show because they are calling in and they're honest about it, you know, just like you here. So I love your
whole story. I'm glad that you called in. I love that you're like one step away from like
doing it for real because like I said, I think it's very relatable and there'll probably be a lot of
guys like you that could relate to your story. So maybe I'm giving them ideas too and corrupting more
people, but I don't want to corrupt anybody. But I hope that you maybe got a little clarity or I don't
know, got some good tips from this call or got what you wanted out of calling in. But I love this episode and
I think it's like super helpful for other people. Yeah. Thank you for having me. Yeah.
It kind of feels good.
Could just be a little open about it too anyway.
But yeah.
That helps, don't you think.
Yeah, of course.
I don't think just sitting around thinking about it all the time, not telling a single
soul does anybody any good.
Yeah, it does.
And wait until you hear it as like your outside.
You might get a lot more out of it.
It's going to be a different experience.
Just wait and see.
Yeah, I'm kind of excited to listen.
All right, cool.
And like, listen, you're going to be super happy because when we hear you.
hang up, my calendar app is going to send you a thank you email. And in that email will be
a link that's going to get you into my Discord, my private Discord, which is fucking fun.
Okay, you're going to love it. So go in there if you want and have some fun. And once your
episode also airs on Patreon, I'm going to give you one month access for my Patreon so you
could see the comments and stuff. So maybe guys will like come in there and comment and give you ideas
too. Or girls. Yeah, that'd be great. All right. Awesome. Thanks so much, Jason. Thanks so much for calling.
And this was fun. Yep. You have a great day. You too. Bye. Hey, y'all. It's Kelly Clarkson with Wayfair.
Ever order furniture online and wonder what if? Like, what if it doesn't hold up? That sofa was four days old.
You should have ordered from Wayfair. With Wayfair, there's no what if. Just style you love and quality
you can trust. Visit wayfair.ca. Wayfair, every style, every home.
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 being girl story.
Like I said, 17 stories. And they're all told in the third person. And they're all true.
I took the interview and rewrote it in the third person. And I wouldn't really call it like
a total erotica book. Think like penthouse letters. It's more direct. It's not so over the top
like erotica. I don't really like that kind of vibe, right? But these are true stories.
of them. They're really short chapters, easy read. You could read, you know, one or two and then skip
around. You could read the whole book. It's available in eback format, paperback format. And finally,
the audiobook is available coming out August 25th. But you could pre-order it now. And if you
buy my book in any format or pre-order it, I will throw in a complimentary link to my Discord.
My Discord does not disappoint. Okay. There's no way you get into my Discord.
any other way than getting the link from me. Okay, I give it to people who buy my book. There's tons of
people in there. Everybody shares content with each other. And that's what you get to do there.
You could post your own pictures and videos. There's tons of channels. We have lots of
contests where you can win a lot of money. It's a super fun place to be. It's a total,
strictly anonymous community and you will love it. I will be giving anyone who buys my book
access to my Discord. It's private, like I said. All you got to do is email me a
screenshot of your purchase, whether you did the audiobook, the ebook, or the paperback.
Send it to me at Strictly Anonymous Podcast at gmail.com.
That's Strictly Anonymous Podcast at gmail.com.
And I will send you the link to Discord.
This is the Strictly Anonymous Podcast.
Strictly Anonymous Podcast.
