Strictly Anonymous Confessions - 726 - FETISH FRIDAY - Doug is a Bisexual Crossdresser who Can Suck his Own D!

Episode Date: December 1, 2023

Doug is a bisexual crossdresser who can suck his own d and he called in to talk all about it. When he figured out he can suck his own dick? When did he realize he was Into Crossdressing? When did he realize he was into guys? Tune in to hear all the details including how he felt about the fact that he could suck his own d***, how one of his girlfriends found out and how they would suck his d together, the positions he uses to be able to do it, when he realized he was into dressing up and pantyhose, the girlfriend he dated who turned him on to guy/guy porn and how and why he realized he was into it, how he went into chat rooms and pretended he was a chick to talk to guys, the first time he met up with a guy and what exactly went down, the other guys he met up with and how it he always was into oral, the first time he bottomed while wearing pantyhose and what went down, how and why he loved hocking up with guys while fully dressed, how he opened up about being bisexual and a crossdresser to his current partner and how she reacted, their first MMF threesome and how that led to them allowing each other to play solo, his first solo hook up with guy and what went down plus a whole lot more. **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

This message is brought to you by avocado mattress, and if healthy, comfortable sleep matters to you, this is one organic brand worth knowing. That's because what you sleep on actually matters. Most mattresses rely on synthetic foams and chemical materials that trap heat, breakdown over time, or off-gas. Avocado does it differently. Their mattresses are hand-crafted with natural materials,

organic latex, organic wool, and organic cotton, designed to be naturally cooling, incredibly supportive, and long-lasting. They're certified organic by got, and meet multiple non-toxic and safety certifications. Made for people who care about their health and the environment without sacrificing comfort. I love that avocado proves you don't have to choose between comfortable, supportive sleep and your values.

This Memorial Day, discover what it means to truly sleep well. Upgrade and save up to 20% on our award-winning mattresses. Shop the Memorial Day sale now and get up to 20% off at avocado-matress.com or select retailers nationwide. That's avocado-matress.com. Avocado Mattress.com. Welcome to the strictly anonymous podcast. Strictly anonymous podcast.

Conversations with online strangers. We place ads online. The Craigslist is definitely like 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. Your friend know that you're banging her or no?

No, he has no idea. And anything goes. The motto of the show, let your freak flag fly. Probably the only good advice I'll ever give you is to re-holt. hide your whips and chain. Here is your host, Kathy. Hey, welcome to the Strictly Anonymous podcast with Kathy. If you want to follow the Strictly Anonymous podcast on Instagram or Twitter, follow the show at Strict Anonymous.

If you want to be on the show, it's called Strictly Anonymous because I change everyone's voices. I change everyone's names. You can call me from a phony number. You can email me from a phony email. I just want to hear your true story. So if you want to be on the show while remaining anonymous, or you don't have to be anonymous if you have something you want to promote, you have an interesting, naughty secret life or not secret life that you want to talk about. You could go to my website, Strictly Anonymous Podcast.com and click on be on the show or send me an email, strictly anonymous podcast at gmail.com.

If you have a confession, you want to leave on my confessions line, I have one of those. The number is 347, 4203579. That's 34749. You call that number 247. make sure you're in a quiet place. You have four minutes leave a message. If you need more time, just hang up, call back. We edit those together. I change the voices on my confessions. Those are all aired on my Patreon. If you want to hear all the confessions that I've received on that line, there's hundreds of them, as well as get all my episodes early and ad-free, as well as get Q&As where I answer all kinds of private questions, as well as see all the R-rated naughty picks of all my guests,

Plus get access to my private Discord where people get X-rated. I don't get involved with that. But Discord is a place where people, my Patreon members, go in as themselves. They post whatever they want. That's where the X-rated stuff is. You get access to all of that. And because this is a Fetish Friday episode, I have two separate tiers on my Patreon. One for hosers.

Those are guys who love fucking pantyhose. And cross-dressers. Any cross-dressers, if you sign up for the cross-dressing tier, it's $10, but you get access to every. everything, all the Paniho's stuff, all the beginner stuff on the regular tier of the picks of guests and the Discord channel, as well as exclusive cross-dressing episodes. I posted one episode a month on there, but because you're signing up and I've been up and running for years, there's tons of exclusive episodes up that you could go and listen to. The Panios tier is $7 a month. The Crescent tier is $10 a month because you get everything. And if you want to sign up for that, go to patreon.com. slash trickling anonymous podcast. The link to that is in the description. Now today I have on Doug. When Doug originally wrote in, I thought it was going to be just an episode about a guy who cross-dresses and is into panty-hose. But turns out he's got this whole other thing going down, which is he can suck his own dick.

So that's where we start out because he throws that out into the convo very early on. He's also bisexual. He's got a lot of different things going on And we touch upon all of them First we talk about how He could suck his own dick How he figured it out how he does it The positions he does it in All the girls that were down for it

Some of his girlfriend's new and joined in His wife who he's with right now joins in Likes to suck his dick with him Eventually he did get into pantyhose And cross-dressing He talks about that Then he did meet a girl Who was like into watching guy and guy porn

and that kind of got him thinking about guys, and he wound up going online and started chatting with some guys, and then he started experiencing a guy-on-guy action. He eventually met up with a guy who was dressed, and then he started meeting up with guys when he was dressed. He's had full-on penetration and did all that kind of good stuff, and then he met his girl who he's with now, his wife. He talks about how he copped to everything with her.

She knows everything. She knows that he's been with guys. She knows that he cross-dresses. She's down with it all. Eventually, he gets a free pass from her to play solo. But they do have a threesome with a guy together. They both hook up with a guy together. He talks about that.

Then they have free passes to play solo. He has played with guys solo. He talks about that. There's a lot of details, a lot of specifics, a lot of different things going down. He's got a lot of fetishes, the cross-dressing, the panty-hose, the guy on guy action while dressed. I don't think it's a fetish to suck your own dick.

I didn't even know that that was possible, but it's possible for him and he talks about that. So there's a lot going on with Doug. So I'm going to get right to it. It'll be right back on with Doug. Hi, Doug. Welcome to the strictly anonymous podcast. How are you today? Not bad. How are you?

I'm good. So listen, Doug, you're a bisexual cross-dresser in an open marriage. Yep. So she knows you're a cross-dresser? Yeah, she knows. She knows. Okay, cool. So listen, Doug, tell me your story. You sound young. How old are you? I'm in my 40s. Oh, you are? Okay. How long have you been married for?

We've been together a little over 20 years. Okay, and let's go back to the cross-dressing. I mean, and being bisexual. Like, which one did you realize you were first? Well, I never really thought of myself as even bisexual. I mean, I started masturbating, I guess, around the typical age. And shortly after that, I discovered that I was always an athlete, always in shape, and build athletic, and hung, which helps. And quickly realized that I was actually able to suck my own cock. So that quickly became part of mine.

Excuse me. Did you put that in the email to me? I don't remember that. I think I did. Oh my fucking goodness. I could just make a whole episode on that. What do you mean? You quickly realize you could do that.

How long was it? And how old were you? Like I said, I typical age, started masturbating. Very slim, very young. And I just like, I remember stretching one morning before we're going out for practice. And I thought, man, I'm like really close. I could probably get it in my both. And with very little effort, I was able to do it the first time.

obviously I got better at it, but. Oh, my God. I mean, is that normal? I always thought that that was like maybe a lie or a made-up thing in porn where they like mock it up or with something fake. I just feel like is the human body supposed to be able to do that? Probably not. Or else everybody would be able to. Yeah, no doubt.

And like I said, I think every, every guy tries at some point. At least that's what they say. But yeah, I was able to do it right away. I'd say probably at least a couple of times. is at my mouth first time. And as I got better at it, I was able to actually suck my cog. Wow. So did you just like never leave your room? It definitely made things easier. That's for sure. Well, it's weird because it's really happened to you very early on. So you don't really

understand every other person's life of like never being able to do that and only be able being able to jerk off with a hand. So you don't really know the difference, right? It just, that was always available for you. So you don't even realize how lucky you were, I don't think, because it was like you could always just blow yourself. No, for sure. It was definitely a heightened, heightened, I guess,

version of masturbating, which was obviously became part of my regular routine because, I mean, why jerk it off when you can suck your own cock, right? So does that tie into the whole bisexual thing? Not really because I was always obsessed with the female form and I usually masturbated to. I pretty much exclusively watched girl on girl porn well into my 20s. Oh, okay. And that was like, again, I knew it was something I couldn't share with everybody, obviously,

and I didn't think people would understand it. And it was just one of those things that if it feels good to do it. Can I ask you how long your dick is that you could do that? How long is it? Yeah, I'm about eight inches. That's it? I mean, are you just limber? I'm very limber, very slim, like I said, athletic.

I know, but there's a lot of slim athletic guys that have eight inch cocks. Like, are you double-jointed or something? I think that eight inches isn't that long. Not that it's, listen, most people don't aren't eight inches and they're like, oh, I wish I was. But it's not like that uncommon, right? But I don't think it's common that guys could do that. So that's where I'm like, how did you do that? It's not about the length.

It must have been about some weird spine that you had or something that you could like contort into this way to be able to do it. Because plenty of people are thin. Plenty people are athletic. Plenty of people are eight inches. Yeah, no, for sure. Again, with little to no effort, I was able to get it in my mouth first time. But I mean, can you do like backbends and flips and stuff? Are you oddly flexible?

I'm very flexible for sure. Yeah, something's going on there. It's a little weird. But interesting, did you realize that this was something that other people didn't do? I mean, I grew up without the Internet age. So, yeah, again, I knew it was something I was going to be able to share with people or ask, hey, can you do that too? But I didn't feel weird about it. I didn't feel like, oh, my God, like, I want to go and suck another dick now.

Like, I just know something I could do to myself and I enjoy doing it myself. Yeah, because if you think about it, listen, whether you're sucking your own dick or playing with your pussy or drinking yourself off. that doesn't mean that you want to go do that to somebody else. Guys are constantly touching their own dicks, but doesn't mean they want to necessarily go out and touch another. So same shit. That makes sense. Okay, but eventually you do turn by,

but let's though stay when you're younger. I'm still obsessed with the fact that you could do this to yourself. Do you ever wind up telling people? Does your wife obviously knows? She knows I was caught once and my ex-girlfriend knew I could do it. We actually have something we would do together. What do you mean, do together?

You would both blow you at the same time? Oh, my God. Does she love it? Yeah, so it was the first time with my ex-girlfriend. Like I said, I was caught once before, but it was something that was never really talked about afterwards. But with my ex-girlfriend, it was just like, I don't know, kind of one of those things were, you know, oh, hey, kind of hinting out a blowjob kind of thing. And she wasn't opposed to getting a blowjob. She did like doing it.

But it was, for whatever reason that day, it was, wasn't happening. She said, oh, you're big enough. You could probably suck your own cock. And I kind of laughed. And she said, no, seriously, have you ever tried? You probably could do it. I want to see you try. So you've acted dumb.

Oh, let me see if I could try. Exactly. Very hesitant. No, no, no. I don't want to try that. That's weird. And again, it was, basically there's a few positions. There's a sitting position where you can reach your arms around your legs

and pull yourself into. yourself, which makes it a little easier. Then there's a position where you can land your back and throw your legs over your head, which is basically you're using gravity at that point. And that's typically what I would do for facials is I would do it in the sitting position and then throw my legs over my head to come on my own face. Right, after you blow yourself. And the sitting position was I would just stay in a sitting position if I wanted to swallow.

Wow. Okay. So when you would do it with that girl, she was turned on by the fact of watching and seeing you and then she would join in. And that's what you guys would do together. Yeah, she was super, super turned on by it for sure. We actually broke up shortly after her discovery of that. I guess not really discovery, but kind of pulling that on to me. And we were living together and I needed to find another place to stay.

So I did live there for a bit still. And there was a couple situations where it continued to happen. Obviously, you don't live, living together. Yeah, everyone that breaks up. They don't just break up one time. You always go back to full around and shit, especially if the sex is good, whatever. She was still turned on by that, but she didn't want to be with you. You know what I mean?

That happens all the time. Yeah. So when does the whole cross-dressing thing come about? Because we haven't figured out that you're by yet. We know this interesting fact about you. Like you're still young. Are you dressing then? Yeah.

Much doing that to myself. It was, again, short of, yeah. after that discovery. It was a friend of my neighbor of mine. They were going to a costume party. And I got the last minute invite kind of thing. And I thought, oh, geez, I don't have anything to wear. I want to go.

And my mother was always one of those people that if there was a wedding or if there was some new event that she wanted to go, she would buy a new outfit and wear it once and never to be seen from again. So she had this collection of clothes that was just there. I thought, hey, my mom's got all these dresses. and stuff and throw a pair panty hose on and a dress and I already had the long hair to go with it

so I thought it's one of those things like football players dress up as cheerleaders in high school and cheerleers dressed like football players kind of thing I was one of those guys that do anything for a laugh kind of thing and my friends knew that so I thought oh this would be hilarious and got dressed up we went to the party and I quickly realized like okay my friends know I'm doing this

ironically and they think it's funny but now there's all these other people here and they're looking at me and I did have long hair and I was very slim and I started to feel I guess awkward. Uh-huh. And along with that, the panty hose is what really started to arouse me. Oh, you wore panty hose with the outfit. So panty-hose was like your gateway drug.

A lot of times, that's the case with cross-dressing. It's not always. Yeah, totally. Yeah. Yeah, it was very evident that that was what I was being turned on by and being aroused by and I didn't feel comfortable being at the party any longer and decided to leave and it was not close to home so I had to walk home like that. You mean like fully erect you're saying like what do you mean walk home like that?

Oh walk home all dressed up. I mean it was Halloween right? Yes. Okay, but you were still uncomfortable maybe because on some level you knew you liked it and you were thinking everyone else realized because it is Halloween. It's the one time you can walk around and not be uncomfortable like that. You know what I mean? It was definitely me getting inside my own head for sure. And wearing panty hose is something that quickly became part of my masturbatory routine or suck

my own cock. It was something that I would do regularly along with that. I guess. I don't know. You tell me. Yeah. And it was never more than that. Like I never started dressing as a woman or stuff like that.

It was definitely mostly just a panty hose thing. So, yeah, as I got older, I got my own car and got some. I live in a small town. I wasn't comfortable with trying to go buy panty hose or lingerie or stuff where I was from. So I would town over and work up the courage to go into a store early in the morning and try and get something or whatever. But eventually that did happen.

To get more clothes, right? So at this point, though, you're young, you're able to suck your own dick. You're buying panty hose. You like the feel of them. I mean, that and it became like it's a sexual thing for you at that point, right? yeah completely for sure yeah it was a matter of it feels good to it right yeah yeah yeah you can't help it once that like clicks in what like you're gonna keep going back and i think that's what makes it become so powerful because especially if you make that connection early on during the times in your

life when you're just like at home behind closed doors and can jerk off as much as you want when you keep then now doing it with panty hose on now you're like clicked in that's the thing you're gonna put them on going to happen. It's like you train yourself into it kind of. No, for sure. And I moved out and I had roommates. So it's always something that, you know, I tried to, I, there was a lot of buying stuff and purging stuff because, you know, the fear of getting caught with it, right? Yeah. Yeah, yeah, yeah. That's got, that's a big cross-dust thing, the purging. They buy, they purge. They say, I don't want to do it anymore. Did you ever get caught? I did get caught. So yeah, I moved down. I had a few group hates.

I lived on my own pretty much from my late teen years on. And I had a serious girlfriend for a bit and we ended up moving in together probably for about a year, I'd say. And she broke up with me. She moved out. And I had been, I guess, kind of flirting. I've never cheated on any relationship I've ever been. But there was definitely a harmless flirting thing going on with the girl at work. And we had broken up and I'd gone to work a few days later or whatever and run into her. And it was all, hey, what's going on? I'm saying, well, now I want to go out, want to have a drink, blah, blah, whatever.

And we ended up going out and hitting it off. But it was definitely more right away. It was very clear that it was just a relationship of convenience and booty call kind of thing, friends with benefits, I guess. And she had told me that she was really into watching two guys. And it wasn't about being gay, it wasn't about them being straight. She was super turned on by watching two guys. And that was something she wanted to do with me.

She loved watching Guy on Guy porn. I had pretty much exclusively watched Girl on Girl porn my whole life. And starting to watch this with her, it was like, oh my God. Part of the reason I didn't really watch mainstream straight point, I guess, was because I didn't find the guy appealing, really. and the guys in bi porn or gay porn or whatever were clearly more attractive and fit and nice cocks and whatnot. So I was definitely turned on by it, but wasn't yet comfortable sharing that with someone. But this girl shared it with you.

She was the one that turned you on to it. Yeah, and it wasn't. I didn't really feel like I couldn't share it with her, but it was also a very eye-opening thing. my god, like girls are like this too. Like girls are kind of kinky too. Like I didn't, you don't know that as a young man. You think everything you think is. Oh my God, I'm the only one. Is that weird? Totally. Especially before the internet because you don't have, you don't, you don't, you can't go online and Google and see a million other people talk about the same weird shit. Right. So shortly after our friends with benefits relationship ended, I ended up trying a chat line to, to meet women.

went on a few times, met a few girls for coffee, nothing really panned out. There was never any really real attraction or we didn't get along on an intellectual level or whatever. And I was pretty much ready to give up on the whole channel line thing. And one night I got a message from a guy on the girl's side saying, hey, I'm actually a guy and just looking to suck hawk and that's all I want. No reciprocation needed, blah, blah, blah. And I thought, oh shit, I messaged them back and I'm like, do guys go for that? And he's, oh, yeah, I totally.

And guys love just getting their dick suck. They don't care who it is. So the light bulb kind of went off. And I thought, well, I like sucking my own cock. I know that. I never really thought about being with another guy. But, you know, I've recently been watching guy on guy porn and being super turned on by it and thought, hey, what the hell? If this is working for him, maybe, maybe I'll try this.

So yeah, eventually I got the courage to go on the girls side of the chat line and had to fake my voice or whatever to leave the message. And I would like guys kind of message me first. Why do you go in? Why do guys go in as girls? Like, why not just go in as a guy so you weed out all the bullshit? I mean, like, why not just go in like, hey, I'm a guy looking for a guy? Why would you go in as a catfish people? Like, why do guys do that?

You pretended you're a girl? Well, I mean, again, the, the, this. particular childline was one of those things where it was free for girls but guys had to pay. Oh, okay. So you're, you're getting in because you're cheap, not because you want to catfish people. Because I think that that's a common thing, right? A lot of guys are talking to chicks, they think, online, but they're dudes pretending. And I just always wonder why, like, especially if you're looking for a guy and guy action, why you would go as a girl. Because then you'd, there's a lot of guys that are going to be like, no fucking thank you once they find out you're a dude. Definitely. And I, I heard everything. I've been, you know,

know chewed out and called everything at the book and whatnot. But again, it was also something that kind of fell in my lap and it wasn't, I didn't really have an avenue where I thought, even if this was something I wanted that I could obtain this. Listen, you were not the only one. It's a very common thing that goes down. I've just never talked to anyone with that cop to the fact that they did it. So it's interesting to me. You're honest. And I think a lot of guys, like I said, do it. It's very common. So I was just trying to pick the brain of the guy that does. do it like why would you but I think the fact that it's free I get it that's how I my whole show started I put ads in the personal section for people to call into my show because it was free

that's the only reason so yeah it makes sense I think then too in retrospect I think if I think if there was some way I could have hooked up with another cross dresser or possibly even a she male that I would have I guess internally felt better about it because it was almost like kind of justifying it to myself oh they look like a female so it's cool But again, that was less likely than hooking up with a guy in a small town. Yeah, yeah, yeah, yeah, of course. So what did you find when you went out there as your fake girl profile? Again, a lot of lashback for sure at first.

And a lot of weeding guys out and trying to figure out what exactly I was going to try and get out of it. And there was a lot of arranging meetings that I would chicken out of or whatever. Yeah. And until eventually I actually had the guts to go. through with it and go meet a guy one night. And I was still living at the apartment that I lived with with my ex-girlfriend, decided to take him back to my place. And I guess size wasn't really something I thought about in that moment. And getting him back to my place, when it was finally revealed, he was like five inches, five and a half inches. And I thought,

okay and I started sucking a scog and just like quickly realizing away size is definitely a thing because this is not enjoyable for me so I mean I I finished the job I guess and the next time I went on I made it clear that I was a size king or size queen whatever it was and that was something that was important and I would tell a guy straight out if you're lying about your description if you're lying about your size don't don't waste my time Don't waste your time because it's not going to happen if you show up and you lied. Yeah. And then, yeah, eventually I did it again.

I went to met someone. I thought, I don't want to bring it back to my place because I don't want to be caught in a situation where I'm not my place. And it's not going to work out or I wasn't into it or then having to get rid of them kind of thing. So the next time was more public and then going somewhere outside that was secluded. it and I guess seeing the goods and then going through with it. So you found a guy that was big? I mean, like what happened that second experience? This is the time when you found the right person.

The second guy was definitely more ideal. He was much larger. It was far more enjoyable doing it. And I quickly realized I think he was so much more appealing in every way that I think I was a little overzealous the second time and it didn't last very long. Because it was too good. Yeah, yeah. He came very quickly and I mean, like I found out to a lot of guys do.

And that was something that I was going to need to be conscious of if I wanted to want it to last a little longer for me to get my enjoyment out of it. Is the enjoyment always oral? That's all I ever put on the table. I'd say probably about the first five or six guys. I hooked up with it was all only oral. And I wasn't cross-dressing with guys at this point. It was just me showing up, suck of their cock.

That was it. And so I'd say it was probably about five or six guys. And eventually I decided to wear stockings to a hookup. And it wasn't for them. It wasn't something I even mentioned on the phone. It was just something I enjoyed. I was doing it for me. And the first time I wore stockings,

I actually got picked up by a guy. We went to his place who it was the next town over. We ended up driving to his house, which was the first time I had actually gone to someone else's house. And I went and changed. I came out of the washroom and he was there in a living room, half hard. And he was huge. Like I'm talking like probably 10 inches at least. And I proceeded to start trying to suck his cock.

and he was big and it was awkward and it was the first time being at someone else's house first time wearing stockings or running someone. So there was a lot of nerves going on. And the size I think made it a little more difficult, I guess. And I guess he could probably maybe sense that. And he kind of threw it out there. He's like, hey, you want to go in the bedroom and have sex.

Oh, so this is going to be your first time. Okay. Now, had you ever played around with any kind of like anal stuff like yourself alone? I hadn't at all. Okay. I never even crossed my mind. Okay.

So yeah, I mean, I thought, oh, shit, okay, this is working out. I've gone to all this effort to meet this guy and here I am all the way next town over at his house. And I wanted this. I didn't feel like I was doing it out of obligation because I wanted something out of it too. Yeah. But I remember that short walk to the bedroom thinking, oh, shit.

Am I doing this? This guy is fucking. big, oh my God, freaking out, right? Mm-hmm. And I got to the bedroom and he was standing at the edge of the bed and I thought, okay, I'm obviously on the bed and I wasn't really comfortable, I guess, getting on all fours and having him behind me. So I guess I thought the only other save option was to lie on my back, which in retrospect

was more awkward for sure because he left the lights on and it was just my first time. And I literally, I know it sounds hokey, but once it started, I really went somewhere else. It was very much stepping outside myself and almost like I was watching myself. And it went on for however long he didn't finish. I don't even think I touched my cock or did anything. And he went on the shower. I went on the shower. I came out and he was again in the living room and he hadn't gotten dressed yet.

He was still sitting there. I thought, okay, let's give this a second goal. A little more comfortable now. been here a while the nerves are passing. So I tried suck his cock again and it was the only time I really had to work for it. Most guys were pretty easy to come. I would recognize the signs and if I wanted them to last longer, I would have to be aware of the signs and slow down or hold off or make it, make it last a little longer. I realized that was kind of up to me if I wanted to last longer and this was the first time I

like I said I really had to work for it and it was just it was a whole new feeling of I guess the sex too it was just very I guess submissive or I don't know if that's the word but yeah it was just it was so different

and you liked it I mean in a good way I did yeah for sure the next guy I ended up with again it was a situation where I had it of going to his house and the first time since the first time that I didn't check out the goods before going with someone and we get all the way to his place and he put some porn on and left

the room and came back and he was naked and I remember thinking like oh shit I hope he's a grower because he's definitely not a shower and he was maybe five and a half six inches and I thought oh shit not again my god I know this is a going to be enjoyable for me kind of thing. I proceeded to start to try and suck his cock and just wasn't into it at all. And I think he could sense that. And he asked, can I suck your cock? And I never considered that before, didn't really, wasn't really part of my agenda.

It wasn't something I thought about. I thought, yeah, sure. Okay, I guess if that's, you know, make this move forward. And if I was hard before he started, I wasn't once he did because I just, I wasn't into it out. And that's that's working through. He's, okay, we could have sex. Right. I thought, okay, well, you're half the size of the first guy I was with.

The last guy I hooked up both. So that's not going to be an issue. And again, it was a matter of, I want to get something out of this experience too. So I thought, sure, okay, let's do that. And he laid back on the bed. And I thought, okay, I'm obviously on top. And I got on top. and I started to ride him.

And I just remember thinking at one point, okay, how long do I do this for? Because I just, I wasn't into it. I wasn't getting anything out. It's the actual sex. And at that point, he started to get really hard. And I could feel it throbbing inside me. And it started to make me hard without actually touching my own cock. And when he came, I exploded.

Mm-hmm. And I mean, that was not something I even thought was possible. A hands-free orgasm. Oh, hands-free? Yeah, I wasn't touching myself at all. Okay. So it was definitely very eye-opening. I thought, oh, shit, wow.

I guess I was very naive, and I really thought, okay, guys do that with each other because that's their only option. And I didn't think the bottom guy got anything got of it. And clearly, they did, because. it was like I said hands free I'd never touched my cock at all during the entire entire episode and I came and I was just like oh my God like it was very I said wow like I can't believe that kind of thing and then the very next guy that was the first time I completely crossed chest in front of someone we went to a secluded place that I knew outdoors

and I started sucking his cock and very early on he started hinting out Oh my God, you're so hot. I really want to have sex with you. He wants to fuck you. He wouldn't stop. He wouldn't like up persisting. And I thought, all right. I was up to scoff it.

I got to do that. So sure. All right. Let's, let's have sex. And made sure he put a condom on. And I ended up bending over the car. And he actually started going down on me. Like, putting his tongue in my, my ass.

and that was on the left field. I was like, holy shit, oh my God, took me off guard. And I was like, hey, sorry. I'm not sure if I'm either that or okay with that. And he was like, okay, that's fine. He proceeded to start to fuck me. And it was very much, I described, I guess, as the first two times I had sex with guys. The third time, I got fucked.

He bent me over the car. And I was getting, I was starting to get hard. And I remember at one point I tried to push myself back off the car to grab my cock. And he was a little more aggressive and a little more confident. And he kind of forced me back down onto the car. And again, I came without touching my own cock. It wasn't a coincidence. This happened two times a row or down.

I was just like, oh, holy shit, wow, that's something you could do. Not something I ever even thought was possible. So, yeah, this is my mid-20s. So it was still not something I ever usually put on the table. But I found as I started cross-dressing every time, every time I cross-dress, guys wanted to fuck me. that became something that happened more regularly. I ended up getting into another relationship.

It didn't last very long. That's the girl that I had mentioned before, the first time I had sucked my cock before of the girl. And we broke up probably about after a year, and that's when I ended up with the girl that I'm still with today. And it was probably about, I'm going to say, two years into our relationship when I finally opened up to her that I had been with guys,

and I started with that and I really thought to myself like shit telling her I've been with guys is one thing but then I'm going to tell her that I cross-dress too as a guy and as a guy who works up with guys and doesn't really consider themselves even by and also cross-dresses

you don't feel like you can tell that to someone and have them understand that you're not gay or you don't want to be a woman or this or that or whatever and I ended up sharing that with her and she was super into it, turned on by it. And I let that settle. And then I brought up the whole cross-dressing thing. And she was, I think, a little surprised, but open and not judgmental at all.

And it was something that I started doing around her. She was the first girl that pegged me, which was super hot and felt very vulnerable. But it was also, I guess, I turned on at the same time. Uh-huh. She knew you were into guys at this point, right? And now you're doing that. Right. Does she, like, where does this free pass come in?

Because don't you have that with her now? I mean, how do you get to the point where you have an open relationship? And does she, but first, but did you tell her about your cross-dressing too? Yeah. So that's, I struggled with the idea of telling her to sharing her with that, that was her too. Because, again, I thought I already told her those guys. I'm going to tell her on cross-dust. And she's going to think, oh, he's gay or he wants to be a woman.

And that was the big fear. Yeah. And I did share that with her. She was very accepting of it, very open, very whatever. So again, it was just something we would do periodically. You have a cross with a cross chest during sex. And we would suck my cock together or she would peg me or whatever. And as just that went on, it just really opened up the dialogue, which I think that alone really

really improved our sex life. We started sharing past experiences. She was someone who had been with a lot of guys before me. She really enjoyed sucking cock. And I was super turned on by the idea of her sucking up the guy's cocks because I knew the enjoyment one got out of sucking a cock. And I think that made it more of a turn-on for me. And eventually we put the Craigslist ad on.

We had like our own separate ads. I would put a cross-dresser ad up. she would put a single female head up and we would try and we would never, we would never lie, but we would always come right out after guys responded to us saying, hey, we don't, we're actually part of a couple. This is our deal. This is what we want. If you're into that, cool, if not, whatever. And it wasn't something we felt obligated to do.

It was just something we were super, again, the dialogue was open and we were super turned out by it, but we didn't also want to do it just for the sake of doing it kind of thing. eventually we were on a trip out of town and we had had a nat up and we were back at our hotel and a guy responded and he ended up coming over and I put sex on the table for the first time and I thought she knows about that or whatever and I just told him

I said if you want to have sex just make sure you bring condoms because we didn't have any right we were used at that point he ended up coming over to the hotel we he wasn't he wasn't he wasn't one number sex he said and we both ended up sucking his cock together and it was just it was super hot and we were both really into it and after that it just the conversations just grew to being open and just very trusting of each other and thought we're we're so open we're so trusting of each other we thought if it was easier for us to have these encounters separately maybe we should look into doing that

and after that we were totally into her hooking up with whoever me hooking up with whoever as long as our one rule was as long as we share it afterwards oh okay but is it always solo or is it sometimes together well that was actually the only time we did it together we've we've tried to meet up with guys we've gone to clubs I've gone to clubs where I've crushed us and we've gone out together and we've tried to pick up guys. But again, it's not something we need in our relationship. So unless the right guy comes along, we're not just going to jump at it for the sake of doing it. But you don't enjoy watching her. She doesn't enjoy watching you. I mean, it's interesting that it's

like something that you both enjoy, but you both enjoy it solo. You never want to do more together. We would be open to it. It just really hasn't presented itself. I mean, after that incident, I've only ever been with two guys since we've been together after that. Oh, okay. How long have you guys been together? Almost 20 years. So you've only been two guys since then? Yeah, so the guy who's cock we stuck together, that was probably around the 10-year mark.

Maybe 12, 12, I'm going to say. And then there was a couple years after that. And then I ended up trying Grindr. And I'd say about two years ago was my first took up solo. And I met this guy and we went to a park and he took me out to a little wooded area. It was more like his backyard than mine. So I was trusting that he knew somewhere secluded kind of thing. And we went there and I sucked this cock and we almost got caught.

I'm like really, come on like first time I've done this solo and so long and that almost happened. I was just like, oh my God, but whatever. And then the more recently the last guy I hooked up with was it was a black guy. And he was, he was big. He was really big. When you met this big guy, the BBC guy, like you're going dressed. I always dressed with guys now, yeah. Right.

So you never, do you feel like if you, like, would you ever want to be with a guy as a guy? Or is it something that you're only into when you're dressed up, like a lot of cross-dressers? I mean, I would definitely be open to doing it. I think it would be something more. that I'd be okay with if it was me and her hooking up with a guy together. I think solo is something

I feel more comfortable doing. Uh-huh. I don't know if it's, again, psychological part of it, but again, it's just I always view, like when I started cross-dressing hooking up with guys,

I never even told them on the chat lines or the Craigslist. I never even brought that up to that because it always seemed when I brought up to cross-dressing, they would always go straight to, oh, you like dressing up like a little sissy, I'll shoot you like a little bitch, you know, this, little that, whatever.

It always got very derogatory and very humiliating. And I think guys just automatically think, oh, you cross-dress, that must be how you want to be treated. And that's nothing could be further from the truth. Totally. And now, does your wife hook up with other people? She has yet to hook up so well. But we do, like I said, we do go to clubs and we do, we do attempt it.

It's just, again, it's not something we need in our lives. and it's only something that we're both, I guess, willing to do if it's the right situation. And now what happens when you go to these clubs? It's their swingers clubs? Like how far have you guys gone there? We've gone with, like I said, very little success when it comes to actually going out to the clubs. And it's, again, it's been more of going out with no expectations. Do you do anything when you go?

What goes down when you go to them? Yeah. We really haven't. I mean, we've talked about it. There's, there are private rooms and seven private rooms at the, the club we've been to. But again, it's, it's just not something we've, we've, I feel a lot of people in that lifestyle. They show up to those places and they thought, okay, this is who's here. So we have to pick someone on. Well, no, I mean, you don't get horny there like you're seeing all these people. So you just go and you guys never have done anything together and you've never hooked up with anyone. You're just kind of like voyeurs? No. And again, it.

not from a lack of not wanting to or trying. It's just, again, it's always been something that we both, you know, very much have a type. We're both into the same type of guy when it comes to the type of guy we want to hook up with. And it's just, yeah, it's just really never worked out for us. Wow, that's interesting. But when you go, you're not into hooking up with each other, having people watch you, nothing like there's nothing really that it goes down.

We've talked about for sure. It's just it's not something that's happened. We don't get to do it a lot. It's not in the town. we're from it's it's always something that happens when we have a weekend to get away or so it's not something we always have access to yeah yeah now does your wife is your wife into you i'm assuming she knows that you could blow yourself right i mean did you bring that up to her like when did that conversation come up that's something we did together early on i have been able to do it in a few

years i'm getting a little old from not as limber and put on a few pounds so but yeah it's like i said i i really think just the dialogue alone has really made our sex life better for sure because just the openness and the sharing and all that. And how long into that 20 year relationship did the openness and the sharing happen again? I told her about the hooking up with guys and the cross dressing probably around the two and three year mark. Right. And we started we started putting ads up and going on chat lines or Craigslist and stuff like that probably around seven, eight years. And it was about five years before we finally actually, you know, hooked up with that. And we finally actually, you know, hooked up with that first guy together.

Yeah, yeah, interesting. And that's been the only thing together. She's done nothing solo. You've just had those couple of guys. So that black guy that was the most recent experience, what happened there? Why don't we end with that story? Sure. Yeah, I got this message on Grindr from this guy. I immediately shared the picture with her because we went together. I was at work and I shared the picture with her and I said, this guy sent me a message. He wants to hook up. I said, what do you think? What do you? think and she thought, oh wow, he's got a nice body and a really nice cock. And she's like, if you're into it, she's, yeah, go for it. And I was definitely intimidated for sure. She was

super turned on by the idea of it and really kind of, I guess, pushed me in that direction. It's not that it wasn't something I didn't want to do, but I think her excitement of it and her being turned on by it was what made me actually go through with it. Just because he was, like I said, very, very big. It was definitely intimidated, not just size-wise, but he was like this big, huge bodybuilder guy. So there was that too. And I ended up going to his house and he let me in. I ended up using a shower quick and came out and he was in the bedroom already and like half hard. And I remember thinking, holy shit, it looks way bigger in person and it's not even hard yet. I was just like, oh my God, I don't even know if this is going to happen. Like this guy is big, right?

And I'm thinking to myself, how am I going to talk myself out of this or how am I going to get out of this situation? And before I knew it, he had me on all fours. He was very, very aggressive, very, he had his agenda and started slow and really worked up to it. And it was, it was definitely the most submissive encounter I've had. He was, he was definitely very, very aggressive, very dominant. Yeah. And how recently was that? That's, I'm going to say, five, six months ago.

Oh, wow. Okay, but did you enjoy it? I did. I, I can. It was actually one of the rare, a few rare times where I came before they did. Oh, really? Yeah, usually it was a kind of a simultaneous thing, but yeah, on a couple occasions, I have actually orgasm before they did.

And, yeah, that was definitely one of them. Wow. So where do you stand with your wife now? You have this free pass. She loves that experience when you tell her. You guys are totally into that. Are you dying for her to have an experience so that you get to hear about it? Yeah.

Again, you know, hearing about her past experiences, she's been with a bunch of guys before me. And Sucking Cock was always a big part of it for her. So, yeah, I've always been super, super turned on about the idea of her hooking up with someone for sure. Wow. I mean, you have a lot going on here, Doug. Okay. You got like you're a hoser. you're a cross-dresser, you're very by, you have an open relationship with your wife,

you're into dudes, you could come without touching yourself, you could suck your own dick, oh my goodness, what am I going to make the, what title am I going to use? I don't even know. Oh my God, I thought we were, I was talking, and I was going to talk to you just about cross-dressing or just about panty hose or just, but it's just a little bit of so much. There's so much there, but it's interesting that I mean a lot of times with the cross-dressing I focus a lot on the fetish and how it makes someone feel and it just seems like that's a part of your life but there's so many other things going on it doesn't seem I mean is it the type of thing where you're always dressing or only when you hook up with guys like how hardcore are you into your cross-dressing I don't I don't do it open public a whole lot it's really something I only do open public when like I said when we go out of town or if we're going to a club or something like that I do it at home and I do it at home and I do it at home and I do it. and it's always just what's never like the dress or everything the full full makeover or whatever is you it's always usually just lingerie or a wig and stuff like that but yeah she's super

into like she she's super turned on pegging me and that that's something she never really ever even thought of or considered and it was uh it was something she was super turned on by the first time we did that so but i mean you continue to do that all the time with her yeah yeah yeah yeah so you live that out with her. It's like something that you do all the time. Yeah, definitely more, more often than not for sure. Interesting. Okay, well, can we get your wife on this to call in? I asked her if it was something she might be interested in doing. And she definitely is thinking of for sure. Yeah, to hear from a woman who's like down with all of this and totally open and gives you a free pass and enjoys it all. I think would be super interesting to hear her side of thing.

And then wonder why she hasn't been able to hook up with anybody or figure that out. Is she into girls at all or just guys? She is, yeah. She is into girls, but never done anything yet? She has before we were together. She's been with a few girls, but yeah, not since we've been together. Interesting. Okay, well, listen, Doug.

Thank you so much for calling in. Like I said, I'm going to have a hard time titling this one because there's a little bit of everything. But it's definitely not just going on my Patreon. It's going to go on my regular episode. But I'm going to edit it a lot so that I take out some of my dumb questions and so that it gets right to the good parts and stuff. So it'll be great. Thank you so much for calling in and sharing your story. All right.

Thank you. Thanks. Bye. Okay. I just want to tell you before you go that my book, it's called Strictly anonymous confession, secret sex lives of total strangers, is now available not only in paperback and ebook, but you can pre-order the audio book. It's still not going to be out until August 25th. you can pre-order it. The book is basically 17 different stories taken from my show.

I kind of picked one story from each category that I talk about on my show. Like there's a hot wife story. There's a cuck queen story. There's a cuck story. There's a gang-bang girl story. Like I said, 17 stories. And they're all told in the third person. And they're all true.

I took the interview and rewrote it in the third person. And I wouldn't really call it like a total erotic book, think like penthouse letters. It's more direct. It's not so over the top like erotica. I don't really like that kind of vibe, right? But these are true stories. 17 of them. They're really short chapters, easy read. You could read, you know, one or two and then skip around. You could read the whole book. It's available in eback format, paperback format, and finally, the audiobook is available coming out August 25th. But you could pre-order it now. And if you buy my book in any format or pre-order it, I will throw in a complimentary link to my Discord.

My Discord does not disappoint, okay? There's no way you get into my Discord any other way than getting the link from me. Okay, I give it to people who buy my book. There's tons of people in there. Everybody shares content with each other, and that's what you get to do there. You could post your own pictures and videos. There's tons of channels. We have lots of contests where you can win a lot of money. It's a super fun place to be. It's a total, strictly anonymous community and you will love it. I will be giving anyone who buys my book access to my Discord. It's private, like I said. All you got to do is email me a screenshot of your purchase, whether you did the audiobook, the ebook or the paperback. Send it to me at Strictly Anonymous

Podcast at gmail.com. That's strictly anonymous podcast at gmail.com and I will send you the link to Discord. So anyway, thanks so much for tuning in. This is the Strictly Anonymous podcast. Hey everyone, thanks so much for tuning in to this week's episode. If you want to follow the show, follow me at Strict Anonymous on Instagram or Twitter. That's at Strict Anonymous. If you are on YouTube, make sure to subscribe.

I love YouTube as a platform for my show because people comment there. And I try to reply back to every single person who post a comment. So even if you're not listening on YouTube and you want to talk about the show, go to my YouTube channel, subscribe and share my videos, a strictly anonymous podcast. If you want to sign up for my Patreon, on my Patreon, you are not only supporting my show, but you will get these episodes early, ad free, and you get to see anonymous picks of my guests. Most of the girls send in anonymous picks, and some of the guys send an anonymous picks. So if you want to see anonymous picks of my guests, as well as support my show and get these episodes early and ad for you. free sign up for my patreon patreon.com slash strictly anonymous podcast that's patreon.com slash strictly anonymous podcast the link is also in the description below thanks so much for listening