Strictly Anonymous Confessions - 865 - FETISH FRIDAY: Drew has a Fetish for Much Older Men and Crossdressing

Episode Date: July 5, 2024

Drew has a fetish for older guys and he calls in to talk all about it. When did he first realize he was into guys? When he did he start hooking up with them? And, when did he realize he preferred older men? Tune in to find to plus hear all about his early interest in panties and how that led to cross-dressing, the threesomes he had with his girlfriend and other guys, the scandalous threesome he had with a gay couple while on a family vacation, the time he had sex with a guy outside in front of his house, his Craigslist hookups, his hookups with transexuals, how he likes to deep throat and a whole lot more. Holiday long weekend REPEAT - originally aired 1/2021 **He's looking for cross-dressing advice, you can email him. He gives out his email address at the end of the episode. it's [e-mail] **To see anonymous pics of DREW plus see anonymous pics of 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! MY BOOK IS NOW OUT FOR PRE-ORDER!!!! Strictly Anonymous Confessions: Secret Sex Lives of Total Strangers. A bunch of short, super sexy, TRUE stories. GET YOUR COPY NOW: https://amzn.to/4i7hBCd To Join SDC and get a FREE Trial! click here: https://www.sdc.com/?ref=37712 or go to SDC.com and use my code 37712 Want to be on the show? Email me at [e-mail] or go to http://www.strictlyanonymouspodcast.com and click on "Be on the Show" Have something quick you want to confesss while remaining anonymous? Call the CONFESSIONS hotline at 347-420-3579. You can call 24/7. All voices are changed. Sponsors: https://bluechew.com Get your first month FREE! https://butterwellness.com/ Try the Butter Wellness perineum massager and use code STRICTLY for 20% off your entire order Follow me! Instagram https://www.instagram.com/strictanonymous/ Twitter https://twitter.com/strictanonymous?lang=en Website http://www.strictlyanonymouspodcast.com/ Everything else https://linktr.ee/Strictlyanonymouspodcast Learn more about your ad choices. Visit megaphone.fm/adchoices

Welcome to the Strictly Anonymous Podcast. 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. With real problems. Do 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 rehydrate. whips and shame. Here is your host, Kathy. Hey, welcome to the strictly anonymous podcast with Kathy. If you

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And my Patreon is a really great fun community. that you could join. It is now $7 a month and you get a ton for that. You get all the anonymous picks of all of my guests. Practically every single female has such an sexy hot pick of herself over there. You also get all the anonymous confessions. You also get Q&A's where I answer questions that people have for me. You also get all of my episodes early in ad-free and you get access to my private discord, which is a great community. as well. What's great about Discord is you get to post stuff yourself. Picks, videos, whatever you want. There's a lot of different channels in there, hookup channels, buy channels, general question channels,

picks of guest channels, naughty picks of listener channels. It's all going down to my Discord in order to get access to everything I just told you about, including my Discord. Just join my Patreon at $7 a month. We can't sell at any time. It's patreon.com slash strictly anonymous podcast. I also wanted to tell you about SDC.com. That is the Swinger Lifestyle Dating app that I recommend the most now. And I get to offer all of my listeners a free trial. That's sdc.com. Use my code 37712 or just go to the description and click on a link and you're going to get a free trial of SDC. And what's great about SDC is it's not just a hookup app where you're going to find other like-minded hot people. It's also a place where you're going to get to be in the know of all the lifestyle events and meet and greets and swingers

parties and all that good stuff in your area and you're going to get a free trial so just go to the description click on the SDC link or go to stc.com and put in my code 37712 now i did beg for reviews recently because it was like really close to a thousand and so many people listened i've never begged before i always felt weird about it but now i just should do it all the time because i got so many people giving me really nice reviews. Thank you to everyone that wrote a review. I read all of the reviews and I love them. So thank you for that. And keep doing it. Like I said, even if you can't write a view, just press five stars. So today I'm on a guy named Drew. Drew is, I would say he's a submissive, bisexual guy who's really into older guys, right? And he's got a lot of hot stories. But he also has this other cross-dressing thing going on and he really is looking for advice on that. So wait until the end of the podcast because he gives, out his email. So anybody that has advice for him on how to like fully cross-dress and get more into that, you can send him an email. He's going to give a shout out to it at the end of the show. But before we get to that, he talks all about being by and being into older guys and he gives a lot

of interesting like hot stories. You should hear this story about what he did on a family vacation. He talks about that. He talks about like the first guy he hooked up with. He got into guys and he did a lot of hookups through Craig's list. He also had a girlfriend that knew he was by and they did a lot of threesomes and hooked up with other couples. He's hooked up with transsexuals. He's worn bras and panties while hooking up with guys. And like I said, he has a fetish for older guys. The oldest guy, you'd be surprised. I'm not going to tell you. You're going to listen. He talks about exactly what happened with that guy and a whole lot more. Oh, we also talks about deep throating. I don't know why. I feel like this is the second person I went deep into deep throating with. So I've always

impressed by someone who could deep throw it. I never have been able to. I've never really tried. I don't know. It's not something that interests me, but it's interesting to me that other people can do it. So we talk about that too. So anyway, I'm going to be right back on with Drew. Hey, Drew, welcome to the strictly anonymous parking. Anonymous podcast. How are you today? Good. How are you? I'm good. So Drew, I don't know if your bisexual side is like a secret life. I'm assuming it is because you've had a bunch of girlfriends you said while you were doing all kinds of stuff when you were younger, the gist of what we're going to talk about today is your buy. You've had some girlfriends I would think that didn't have any idea.

You had one girlfriend that you had a lot of like male, female, male, threesomes, even fours sums with her, right? So I'm not sure if now you're married and you're in a relationship with someone, they know that you're by, but you're definitely a bi guy. And then you tried panties when you were younger. You would steal them from your mom. you looking to like fully cross-dress now and all kinds of different things we're going to be talking about. But first of the question I had is, are you married now and are you outwardly by or is this a secret life?

I am by. I'm not married. It's kind of a secret but not really a secret. I would say probably less than a handful of people know about anything. So it's not top secret, but it's also out there a little bit. Yeah, yeah, yeah. Okay. And but when you're dating, do you date? women or do you date men or do you date both? I've dated mostly women. I have gone on a few dates with some guys, but nothing serious or long term. But have you ever, what's the longest term relationship you've had with a female? A couple of years.

And when was the last time you dated a woman? I would say the longest, or the most recent long term I had was probably about four or five years ago. I was with a girl for about two, two and a half years. Right. Now, did that girl know that you were by? She did not. And now when you're with these women that don't know, do you cheat on them behind their backs with guys? Or are you able to just keep that on the doubt?

Do you just push that aside when you're dating a woman? A little bit of both early in our relationship. It was just very faithful and just her and I. and probably about halfway through, started, you know, beating some guys on the side and kind of went off from there. Okay. So let's start in the beginning, though, because I know that, and before you even started hooking up with guys, because you hooked up with guys when you were pretty young, too, right? But I know that one of the first stories you told me about was that when you were super young,

you would steal your mom's panties, right? Correct. I would. So let's start from there. Started at a young age. I was about 12. And what did, do you remember that first time that you were like thinking about? Do you remember how it kind of popped into your head? Yeah. You know, when you're around that age, you start getting curious about things and start having different thoughts and feelings about things.

It was the internet age and checking things out. How old are you now? 32. Oh, okay, you're young. So then you start checking things out, and then one day you're home alone, and start getting curious and checking things out, and that was the first time that I tried on panties. It was the Internet age, and 12, 13 years old, you start getting curious,

and just checking out websites and seeing different things on there, and happened to stumble across that, and it got me excited and more curious about it. So one day when I was at home alone and I had an opportunity to try it out myself, and I did. So you go into your mom's drawers and you take out like a G-string or a panty and like you put it on and does it turn you on, do you jizzing it, do you put it back? What does that first, how does that first go down?

The first time I put them on and checked them out. It was a, I still remember it vividly. There was a black lacy thong and just tried it on and poured it around and kind of just sat in it and rubbed myself a little bit and just trying to figure things out and trying to figure myself out. That was all that really happened the first time. So nothing too crazy. Then it progresses. And so go and progress. Tell us how it.

progress. It progresses, so more times when I'm home alone and get a chance to continue to experiment and feel myself out, it progresses into more and more. And then I tried on bras and more just the lingerie things. But were you like getting yourself off at your mom's stuff? And it was like it was when nobody was home. Because I know that you said you grew up with a bunch of brothers, right? So would you have to wait till no one was home?

Were you stealing this stuff in your room when people were around? Like, how naughty were you? I was home alone. So I would go in there and steal them or borrow them. And then, like I said, put them on. And eventually it would progress to where I was getting myself off and wearing just the panties. And then I wanted to see what else I could progress to. Didn't really know really anything about cross-dressing.

or anything like that at that age. But it was something that as I'm doing it and starting to figure some things out about myself, I felt comfortable in it. So it started being more and more comfortable each time. And again, it was that. And then also seeing things with guys and with girls and kind of figuring things out that way. So I guess it was kind of a different way of starting out the sexual experience. Maybe some normal pass?

Yeah, well, I don't know what's normal. It was normal for you. This is like how it started, right? And then, so now I know that when you were young, maybe you were like 17, right? Well, when did you lose your virginity to a girl? Because when you're 17, you lose it to a guy, right? How old were you when you started fooling around with women? When I started fooling around with girls, it was 14, 15, lost my virginity at 16.

Mm-hmm. And then now, how did the guy on guy actions start? So again, part of the internet age, the old school AOL chat rooms, just in there chatting one day. And I would check out mail rooms and those kind of things on my own and going there and talk to people and just happen to find a guy in there that was close to my age and in the same town. And so I met him through. Well, let me ask you this. Did he go to your school or like a school that was close by? He was older than me.

So he was two years older than me. Okay. So he was just out of high school. Found out we didn't know each other. Uh-huh. So for me, I was comfortable with that. Yeah. With my first time and nobody really knowing or me even really knowing what was going on.

Where do you guys meet up and what does exactly happen? Well, the first time, the first time we were supposed to meet up, we were supposed to meet up at a park just to kind of meet and greet and kind of check you other out and make sure that we're legit and we're entrusted and he had kind of known from our conversations that it was something that was very new to me. I'd never, you know, partaking in that. Yeah. Never been with another guy. So we were supposed to meet there and something happened. So it didn't work out that time. And then a ballsy move on my part, the next time we met up, it was in the middle of the night when I had him come to my house.

which was very risky because my parents were home. But again, it was midnight, 1 o'clock in the morning, and I had him come over. You sneak up through the front door, did he climb through a window? We actually met out in my front yard. I had lived in kind of a secluded area a little bit, so we had met out in my front yard in the middle of the night.

But then did you go inside, or do you hook him outside? We just stayed outside. Oh, interesting. Where? Like in the bushes? Just in my front yard. I had a blanket laid out in kind of a darker area. And right there in my front yard.

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I had a blanket laid out and kind of a darker area. And right there in my front yard. Okay, so when you say you really do live in a secluded area. So there's no other houses. No one could look out their window and see what's going on. Everyone's sleeping. So you have no. No neighbors, right?

So you put out a blanket and then what do you guys do on that blanket? Everything? No, not everything. Actually, it was just me. I was only one that did anything. I gave him a blow job right there in the middle of the yard. Oh, my gosh. Yeah.

Crazy first time. Did that add to the excitement? Or I think when you're just... Okay. And when you're that young, listen, I remember banging guys in like their cars, like my boyfriend's in front of our house. When you don't have any other options and you're super young, like you do shit like that.

Like I remember doing crazy stuff. Looking back, it's wow, because an older brain thinks things through more. But I think when you're young, you just don't think, oh my God, like my mom could wake up and walk right outside. When you're in it, it just makes sense, right? That's the only place you're going to do it, right?

Yes. And I think that's why it only went as far as it did, just because one first time, nervous, but also just the fact that yeah anybody can can wake up at any time and and walk outside and see something that they probably would never you know unsee well they'd never be able to unsee that so that so you blow him do you see him like regularly after that or was that like a one one and done situation that was a one and done thing it's something that he wasn't interested in and we just kind of went our separate ways okay but then now because I know

you have an older guy thing, right? So after him, you hook up with your first older guy, right? Yes, yes. I've only been with one guy that was younger than me. Everybody else has been older than me. So from there, Craigslist became a huge spot for me to visit to try to find. Hookups. Now, did you go looking for older guys, like specifically because you knew that you were

into that or was it just because that's what you found then you got into it like which came first being attracted to older guys just wanted to take out the risky part of or anybody knowing the other side of me older guys i didn't have to worry about it also at the same time was we're guys that i was attracted to and him attracted to and so what's your type so older what else do you look what what else did you typically look for older guys in somewhat good shape. I like the hair of your chest. Just confident older guys that are in good shape.

But do you like guys that were really well hung? Did you like guys from different race? Did you have any of that kind of specific thing? I've had guys of different race. Older guys are guys I'm attracted to. I also like black guys as well. So you do. I've been with some Asian guys.

Who doesn't like a big cock? Yeah, that's what I was getting at. I think most people did. Right. Okay. Are you a top or a bottom? I started out as a top when I started meeting with guys and now I am a bottom. Oh, interesting. So like a switch. That's what they call it, right? Yes. I've learned these things. Yeah. It's been a long time since I topped.

Oh, really? Interesting. Okay. So now let's get back to that first 35 year old. So that guy, where do you meet up with him? You met him on Craigslist, right? And like, where do you guys hook up and where do you meet? And is that the first time you top a guy? He was the first guy I topped. I met him through either an AOL chat room or Craigslist. I think it was through an AOL chat room. Right. I talked to him and then I started going to his house and we were messing around and hooking up for probably almost a year.

Did you have a girlfriend at that time? I did have a girlfriend at that time. So this was like all in the down low? She didn't know. Okay. Nope. So you're hooking up. Now was he a single guy?

Was he a gay man? What was his story? He was a gay, single guy. Oh, okay. He was by himself. And so we had, you know, we had kind of developed a, I guess now you would call a friends with benefits type thing. Yeah. So we would message each other whenever we wanted to meet up and hook up.

and we would do that and we did that for about a year. Okay, and now you would always top, right? He was the bottom. Would you guys have to do oral to each other? That was like mutual kind of a thing? Yes, yeah, lots of oral. I would top him. He taught me a lot of new things

and obviously experienced a lot of new things and it was a fun time for that year. Probably for him too. He kind of like struck gold, right? Here he is like a 35-year-old guy. He's got this young, hot guy, just coming over his house whenever he wants. I think he enjoyed it as well.

Yeah, yeah, yeah. So now would you like make out with him? I did not. Didn't make out with him. I think I was just too nervous too or something new. I've never done it before. We kissed, but never fully made out or anything.

And so you hook up with him for a bunch of times. Now you're like dating a girl. You enjoy women too, right? I do. I do. So you have that girlfriend, you have this guy, And then do you just continue to hook up with guys all through high school and when you get out? I did after we kind of had our thing for a year. During that time, we met a couple other guys as well.

And then Craigslist took over the world looking for different hookups. And from there, I found a lot of different things on Craigslist. Anybody who's ever been on there before knows. At that point, I was out of high school and into college. I tried, met with some couples. I was a single guy. I met with a couples. Met with a male-female couple.

Met with a transsexual female as well. So I tried a few different things. So when you met with the male-female couple, was it that the guy was by or were you both of them? Had both experiences where the guy was by, the husband was by, and then had experiences where the husband wasn't. Okay, and you were just with the wife? Yes. Okay, and now around college, that's when you had the girl that you had all the threesomes and buy stuff with that. She was the first girl that knew that you were into guys, right?

And you were open with her? Yes. Yep. We had had a bi-we met another bi-couple, and then we had two bisexual threesomes. I think that that's kind of major, that like you finally, this is the first. first person that you're really open about it. Like, how come this girl? Like, how did it happen that you let her know about your secret, right?

Because nobody before this knew. No, and I don't even think she really knew then as well. Well, didn't you fuck guys in front of her? I ended up getting fucked up front of her. It kind of just happened. We were drinking and talking and the conversation of what were some fantasies of yours and what's some fantasies of mine. and just kind of threw out different ones.

And some people will share fantasies that they know aren't going to scare anybody off. Yeah, totally. We got to the point where we just shared our fantasies without worrying that we were going to get judged by the other person. Was she by? She was not by, but she was comfortable with playing with females. Okay. So we were fortunate to find a couple single guys and to find a couple as well that we had. met up with and had and had some experiences with during that time.

So what's your guy's first experience with another guy, you and her with another guy, or was it with another couple? Our first experience was with the other couple. We had met them on Craigslist. The guy and I started talking to kind of get to know each other and figure out what we wanted and what they wanted and if it all matched up. And then from there, we exchanged phone numbers to where him and I were talking. talking and her and my girlfriend at the time were talking about everything. So we were probably

talking for about a week and a half, two weeks before we finally met them for drinks and a night out. And then did you guys all hook up that night? We didn't hook up that night. We made out and touched. We just met out at a bar. Nothing too crazy. Just wanted to get comfortable with each other. There was no bisexual stuff going on that night. But then probably, oh, actually the week later, we had met them at their house for to meet up and hook up. And then that's where first she started playing with him. I started playing with her. And then we would switch.

And then I was playing with him and she was playing with her. Oh, okay. And so did you, was that, did you go all the way with that guy and she did everything with the woman? She got eaten out by her and then fingered her. And then the guy and I both sucked each other. off. And was that like an amazing experience to have that threesome with your girl? Yes. Yes. It was a lot of fun. We both enjoyed it. Again, it was an older couple than us. We were in our early 20s and they were in their mid to late 30s. Okay. So that was the only time we had met them. She had fun and she was

comfortable with it, but she was then interested or wanted to or said she wanted to meet some people that were a little bit closer to our age. Okay. Didn't kind of experience that, but it never worked out that way. But after that is when we had two separate hookups where we met up with two other bisexual guys, single bisexual guys. Right. So at this point, she knows that you had that experience with the guy and you were into it

and you're like, you want to do it again. And now is she turned on by seeing you with another guy? She was. She was turned on. And I still don't think she ever thought that I was fully bisexual and attracted to guys. I think she just thought it was a sexual thing. And one of those things that guys fancised about having a threesome with a girl and watching a girl be with another guy,

I don't think she ever thought that I was fully bisexual. Mm-hmm. So now your next threesome with the other guy, with the two other guys, does she like fuck you both and you and the guy hook up? Is that what's going down in those threesomes? Yep, yep. All three of us played with each other. We had met both times. We met them out for drinks, again, just to get comfortable. And after drinks, we went back to our place. And we all played with each other. And it was when I got, I was a bottom that night, both nights. So you were like a switch when you were younger, right? Because I typically used to think most people really have a preference, right?

They're either top or bottom. And then I talked to some guys and are like, no, like some people could be a switch. They like both. But like you started out like you were a top. But did you enjoy being a bottom more now? Because you say you haven't topped in a long time. I do enjoy being the bottom more. When I'm looking for guys, I mostly look for tops.

I will top occasionally if we got to that point. but I would definitely prefer to be to be a bottom. Okay. So you have those those threesomes with that girl. Why would you break up with that girl? That's what she should have. It wasn't my decision. It was kind of just a mutual thing.

Yeah. You know, we've gone separate ways and been friends, but I'm no other crazy fun experiences after that. At least out with her. And did you have any other women since her that have known about it like she did? Nope. No one else. No other females know anything

about my bisexual side. Okay, so you continue after you guys break up. How many other, did you do it a lot? Or were those only times with her? Those were the only times with her. Those were the only three experiences we had. Okay, and then when you guys break up, you go back to hooking up with guys

and three sons with couples and stuff and you're always getting people on Craigslist? Yeah. Yeah, that was the kind of when everything. thing took off. I was, you know, finding guys on Craigslist and some couples. Didn't you? What happened on the family vacation? Oh, crazy times and Craigslist coming in clutch. So this is when you're younger, right? We're going back a little bit now. Yes. Yeah, I was still in college. Yeah. It was, you know, in the summertime. We were in Florida and, you know, enjoying the weather.

And, you know, at that time, old enough, I'm 21, 22 years old, kind of old enough to enjoy things on my own. Yeah. And so looking on Craigslist and just, you know, looking to see if there's anybody in the hotel. It's a big resort. So I'm looking to see if anyone's on there and happen to find a gay couple that's staying in the same hotel

just on the other end. Oh, wow. Same g-mails with them, and they invited me over to their room. No way. How old were they? They were in their early 40s. Were they attractive? They were.

They were both fit guys, good-looking guys, older and good shape. Uh-huh. And what about you on scale of 1 to 10? Oh, probably about 7.5. Okay. At that time, I was in a little bit better shape than I am now. and in college at 22 years old. So I'm looking pretty good.

So they're looking for a hookup. You go in to their hotel room? Yes. Yep. They gave me their room number and it was on the other side of the resort. So I went over there and took the elevator up to their floor and met them in their room. And what happened? And how long were you there for?

And did you see them more than once? Only saw them once. I was there for about an hour. It was the middle of the day. I was there for an hour. One was a top and one was a bottom. So were you the same? You were in between?

I was in between both of them. Oh, wow. So you're fucking one guy in the ass while the other guy's fucking you in the ass? Does that go down? I was getting, I was getting fucked while sucking the other guy. Oh, okay. So we had done that. I blew both of them.

It was the first time. That was the first time. I had eaten a guy out and also got eaten out by a guy. Oh, so like his ass? Yes. Okay. Mm-hmm. Yeah.

So we had done that. It was the first time I had made out with a guy. Oh, really? Both of them? Both of them, yes. Okay. Yep. So a lot of first during that experiences.

How fucking naughty is that? And then you come back and you're like, hi. You'd show you like your brothers, your parents. You had just eaten ass, got fucked, fucked guys. Like, oh, my God, if your parents only knew. No, no, no, nobody knew. Of course, but I'm just saying, imagine. You just come back like nothing happened.

But meanwhile, you had the whole hour of, like, crazy sex with guys. Yes, I don't think, you know, nobody knew. Yeah. I'm just off on my own and nobody's expected or even asked any questions about where I was. Yeah, of course not. No one would ever think that's going down, right? Nope. No one thought anything of it. And now like your brothers, like in your family,

because like my whole show is kind of like based on the premise that. Like you just never know what people are doing, right? If your brothers knew that you were like constantly hooking up with guys like throughout your whole life, like would they be like no way? Or do you feel like it's obvious in any way, shape, or do people would have no idea? I don't think anybody would have any idea. I don't think there would be any guests or maybe,

I kind of had suspicions and all that, but I don't think anybody would have any clue. So that was a hot experience, I would think. It was. It was. It was a lot of fun. And like I said, a lot of first. And so it opened me up to even more things. Right.

So then what do you go, because they opened you up to other things and all that stuff, like now that you, after that, you know, you're hooking up with guys that are you making out more? Are you hooking up with more couple? like gay couples? Like what did you lead to? It just led to, you know, being more open and experiencing things. Yeah.

I, you know, grew into more to more kinky things, growing into being more comfortable of making out with another guy. I enjoyed eating, eating them out, as well as getting eaten out. So it was,

it just opened me to more things than just blowing a guy and being a bottom. And I'm sure, because you're still on Craigslist at the time, because listen, my show was based through getting guests on Craigslist for a while, and then Craigslist went bust. Yes. But all this time, everything is still happening through Craigslist, right? So now, do you normally put, were you putting ads on Craigslist or were you looking for ads or both? Both. Both. I was looking and as well as posting once I got into college and kind of got more freedom to go out and do things without being questioned.

or asked about where I was going, I started posting more ads and getting a lot of responses. Well, I could imagine. Now, would you get specific into all the kinky things that you were into when you would post your ads? I posted that out of the bottom, but open to trying new things. And obviously asking guys what they're into and asking guys what their fantasies are. because I'm more of a pleaser and submissive. So whatever they told me to do or wanted to do, I was pretty, and still am pretty accommodating. Mm-hmm.

So I was posting those things as well as replying the post that caught my attention. Now, did you ever do any kind of wearing? Because, listen, we started talking. When we first started talking, we talked all about you trying on lingerie and panties and stuff like that. now we've just been talking about hooking up with guys. Now, did you ever put, and now you did hook up with a more than one transsexual guy, right? Or transsexual, right? Correct.

Yes, I've been with about a handful. Now, did you ever dress up when you were with anyone? Did that ever, did you ever bring those two things together? There were some guys that were into panties that wanted me to wear panties and I would. The most that I've worn for a guy is panties in a bra. So, yeah, there was guys, and then that's really what sparked that whole interest, even more was guys being interested in that and wanting to see me in lingerie. And that's what really got things sparked for me.

And then you started doing that? Yes, for guys that were into that, I would definitely wear panties and bra. to when I would meet up with them. And now, did you find them because that's what they put in their ad, or did you put that in your ad? Both. Both I would post it. That is something that I was interested in,

but then also guys would express that as well. Because not everybody's into that. So guys, I would, I really liked it and really enjoyed it. So it was definitely one of the many kinks explored. Right. Now, all these all sound just like hookups here and there, right? Now, when did you meet, like, the guys that you said that you dated for a short time, when did you meet those?

And how come those turned into, or did you just go on dates? We would just go on dates. One guy that I met, he was in his 50s, we would just, we were hooking up quite a bit, but then we would go and grab something to eat or grab something to drink and kind of just hang out while also hooking up. It wasn't just walk in, hook up, do our thing, then walk out. It was a little bit more than that. So I wouldn't call it fully dating boyfriend, boyfriend,

but it was definitely more than just hooking up. Now, did you ever get cop any romantic feelings with any of these guys? He was probably the closest one. Mm-hmm. Just because the guys that I was meeting and talking to, they were looking for just hookups. And at that time, same time, I was too. So haven't really found somebody that wanted more than just a hookup.

Now, did you, like, hook up, quote-unquote, with a lot of married guys? Or, like, what was, what was, like, the demo of most of the guys that you met on Craigslist? Were they typically gay? Half of them were, probably third of them were married. The other third were probably bisexual, a lot like me. And then the other third were probably gay. Right. So a few different demographics, I guess.

Yeah, yeah, yeah. And now, was it the only that one guy that you fucked for like a year? Like, or was there anyone else over those years that you were hooking? Well, guys, did they ever last that long, too? There was a couple guys that lasted roughly a year. Right around there and or guys that periodically, you know, throughout my time, we hook up or occasionally hook up but nobody

I would say probably the longest hookup I've had with a guy it's probably about a year and a half maybe a little bit more yeah now in all of these years of you finding randoms did you ever wind up hooking up with any friends or people that you know or was it always strictly like strangers

one guy I ended up hooking up with was a friend And we had, I was looking up with the guy that he was hooking up with. And then that guy mentioned he wants to have a threesome. They're not going to turn down a threesome with, you know, good looking guys. So, yeah. Said yes. And we both show up.

And I think we're both very surprised to see the other person there. And that was, and he actually is the only person that I've ever hooked up with, the only guy I've ever hooked up with that was younger than me. Oh, okay. So now, who was he, a guy from 10? a guy from high school, a guy from college. Oh, a close friend from college. Wow. And so you, and did you have any idea that he was or no?

No clue. So you're hooking up with a guy. Without you knowing, he's hooking up with that guy. That guy says to you, let's have a threesome. I have another guy that I'm hooking up with. Let's all do it together. You're like down. And then you walk in and it's this fucking guy.

Yep. Completely surprised. And he was just as surprised as I was. Oh, my God. Now, were you turned on? Were you like, was it uncomfortable? I was. I know you walk in and he's naked with a with a nine inch cock.

Oh, my God. I'm shocked and shocked even more and then, you know, obviously having a good time. Shocked because you know him. Shocked because he has a nine inch cock, right? Yep. Yeah, that's interesting. So guys, like you like length too, because I would say as a woman, like I don't want someone that's nine inches. That's just way too long.

I have a cervix. It's going to stop that fucking thing. And I don't like it. to be touched. So I prefer with, I think a lot of women are like me and that. Like we really like thick, right? But too long could be like kind of hurt. I don't know. But it does. Right. For you too. So for a guy like you feel. But so what do you do with the nine inches? Is it more of like a visual thing? A visual thing. Obviously feels different when he was nine and pretty thick as well. Yeah. So obviously blowing him and having a mouth full.

Yeah. Then also I had an ass full as well. Yeah. I was different feelings, yes. Different feelings and obviously felt good. Do you deep throat? I have. You can?

I have. That's a thing. Like, I could never deep throat. I don't, I've never really tried, but I think that, like, do, is that something that you learn? Or is it just something that you could do? I don't even know. I think it, for me, I think it just came from practicing. So you did practice?

With different guys. And obviously some lengths are a little bit easier than others. It makes it a little bit harder the longer they are. But, you know, I've had some success, deep-throating. I more so love being face-fucked. What's that? Well, how is that different being face-fucked? Because you have to be able to deep-throat to be face-fucked, right?

I think so. For me, it's just the pounding of the cock in my mouth and back of the throat. Yeah. And there's no gagging going on. So you must have, because I just wonder, I've never been able to deep throat in my life. I've never went on a mission trying to figure it out. And I've had a couple women talk about it.

And I'm just curious, is it something that you were like, you saw it and you were like, oh, I want a fucking deep throat. And then you looked into how you could do it or how does that happen? Or one day some guy just shoves his dick down your throat and you're okay with it? I think it was a combination of watching porn. but then also had a guy that wanted to do it and asked if you could. And so I tried and enjoyed it. But did you like lean your head back over?

Someone once said this. Like you lean your head back over the bed and then it goes down easier? Or was it just something that or is that not how to do it? Like how would you like how was it taught to you? I've done it where I'm on my knees and I've also done it where I'm laying on the bed with my head off the end of it. Yeah. More so looking up. Uh-huh.

So I've done it in a few different positions. I'm just curious because I don't know how the fuck someone could do it. I've seen it, you know what I mean? And now is it, is it pleasurable for you, I would assume? Because you're like submissive, right? Yes. Yep. I love being told what to do.

Mm-hmm. And whatever guys have asked me to do, I've always done it. Ready, willing, and able. Yes. Right. And now I know that you say that you want to fully crush your. dress now. What's stopping you? And what does that mean fully cross-dressed meeting, leave your house that way? Or? I'm not sure exactly if it's, I want to get fully dressed and leave my

house and go out in public or fully dress and meet another guy. What's holding me up is just the nervousness, but then also not knowing exactly what to do or how to fully dress. And over the last couple months, I've started fully shaving my body and watching a lot of YouTube videos and those kind of things to, I guess, do research. But there's a lot of things that I haven't done that I don't know how to do or even where to start. Like what? So now you had this thing where you were younger and you would go into your mom's drawers and take things. I do remember you saying that you used to steal panties from your brother's girlfriends, too, right? Yes.

Okay. Yep. So did somewhere along the line you stopped doing those kind of things when you moved out and you were on your own and now that you're like locked up in COVID world, you're thinking about it again? Or have you always been dabbling in the panties thing? I've been been into the panties thing. Obviously when I was younger and putting on bras, none of them fit. Yeah. They're all too big for me.

So just not knowing where to start and the makeup and the hair and what looks good in an outfit and those. kind of thing. I just want to make sure that I do it right. Yeah. And, and just make sure everything looks good when I do go out or do meet a guy. And you've never met a guy fully cross-dressed, right? You've done a little bit here and there, right? But never fully cross-dressed. Correct. Correct. The most I've done is I've showed up to a guy's house in panties. And they were underneath your clothes. Like you're dressed up as a guy, but you have panties on underneath. Just had panties on. And so now, Nothing over the top of them.

Oh, so you're outside in the date. This is so I'm assuming it's at night. Tell me that story. Yep, just at nighttime, the guy's fantasy was for me to be dressed in just panties. Okay. So he wants you to come over like nothing else on except panties. He obviously doesn't live in an apartment building, right? He's got his own house.

You're beating him at his house. You're not at a hotel. Okay. Does he have fucking neighbors that can look out the window? He lived in an area. where it was just him. Okay. Out in the secluded area.

Oh, okay. So that's easy. Yeah. Yep, worked out perfect. But you're driving in the car with nothing on? Nothing on? Just my phone.

Oh, my God. Thank God. You didn't speed there, right? Like, I would hope you did everything you could not to get pushed out by a cop, right? Oh, my God. Yeah. Yeah. Yeah.

Yeah. I can imagine. So you get to the guy's house. You have just panties on, right? You knock on the door and then you go in and you're, I'm assuming, because you like dismissive. He's obviously a dumb if he wants a woman, a man coming over dressed in a panties, right? Yes. Yep. So walk, drive over, knock on the door, come in. The first thing he has me do is I suck him right there in the doorway. Right. Start blowing him and then we move over,

we go upstairs to his bedroom and we start making out and start touching each other, rubbing up and down our bodies and then he gets naked I start taking all of his clothes off so we're in his bed and I'm still in my panties and he's he's naked and I blow him again and he starts sucking me

as well and then I turn over doggy style and he starts fucking me from behind and then as he is fucking me he pulls out and then comes on my face. Mm-hmm. And as a submissive, that must be hot to you, right?

Very. Mm-hmm. There's a thing. My last caller, I don't know if you've listened to my most recent episode I just aired, which is Jamie, right? It's such a great fucking episode. He talks about a lot of different things. I think you'd like it.

He's by, right? So he talks about a lot of stuff. And he got into, like, Complay, he said. And I didn't know what that was. I had never heard of it, but he said basically that's people that like to walk around will come on their fate. Like, do you know about that at all? A little bit. I mean, the most that I've done other than getting, you know, cummed on.

Yeah. I've been cum swapped or I've had come in my mouth and made out with a guy. Yeah, yeah. So that's the extent of the come play that I've. Right. I remember once I had a guy who called in and who said like a guy like just on his face and he went home with that. and the thought of having it all over his face was hot. And I'm assuming he didn't put that term to it to come play.

Because when I went looking, Googling for it to post something on my Instagram about it, I was like, oh, my God, all it was just like pictures of people would dry it up come all over the face. I'm like, I'm not going to put a picture of that. But that's basically like what it is. So I was just wondering because you're submissive whether you're into that. But so he jizzed all over your face. Yes. Right.

Yep. And then now is the end of it. and, you know, cleaned up and went back home. Right. And so all these people, now where do you find guys now that Craigslist is not happening? Kick. Kick? Yep.

That's how people meet up and hook up in situations like this. That's how I've done it. Unfortunately, since Craigslist shut down. Yeah, exactly. Thank God by the time Craigslist shut down, I was like, I have too many, so many people just emailing me to be on the show I don't need it. But the first couple of years, that's the way I got it. collars is from Craigslist. So now what are you, because you're young, right, you're 32. I know that

you said you're currently seeking advice on how to go about fully cross-dressing as a female. If you're a perfect scenario of your future, what does your future look like for you as far as dating? Do you ever want to get married? Do you have anything like where you could be like transgender or no? How far does that cross-dressing thing go with you? That I'm not sure of. Right. I want to do it the first time and at the same time I'm nervous but I'm also excited for it again I've gone to stores and tried on clothes and looked at certain things and trying to figure out sizes and style and those kind of things but I think once I fully do dress and have that first time experience I think I'll know from there what what the future holds yeah because it's interesting because I wonder and I think a lot of

people that don't know a lot about it. Wonderful. Is cross-dressing the start of somebody being transgender, but probably not? It's not all the time, right? Because some people like to just cross-dress and maybe they just do it, but it stops there. Some people cross-dress and then they realize that they are transgender and maybe they feel like more as a woman. And I would assume some people don't know, right? For you, you don't know. Do you feel like a man? Do you have that feeling where you're a woman? When I am, when I have my panties on, I do. I've enjoyed the feeling of having a fully shaped body and the compliments that the guys

have given me. Yeah. When I've done that and worn panties and things like that. But to say that I feel like a fully like a woman, I think I'll know that or confirm that when first time I fully dress. And now do you want to put a shit? Because I know that you're like looking for advice on how to go about fully dressing as a female right. I know I've had I know that a lot of people who are going to be listening to this episode are going to find it because they're Googling about this topic because they're into it. Whether they're cross dressing currently or they're thinking about it like you. Would you want to give a shout out to people getting in touch with you to give you advice or to talk to them? I don't really know. But maybe if you're looking for that kind of advice,

maybe there's people listening that could help you definitely and I've watched YouTube videos and Google things and just trying to find out what's what's best for for me and and obviously any advice anybody has is right so now listen if anyone has advice for Drew as far as cross-dressing fully and how to go about it whether it's like the best YouTube video or a blog or a Reddit or you could help and you want to maybe email Drew, right? Do you want to give a fake email or do you have any kind of an email account out there that you'd want to give out? How would you want to go about them giving you advice? They can email me at Drew Smith. I.L at Outlook. Say that again, Drew Smith. Smith. I.L. at Outlook.com. Okay. So it's Drew Smith, I, the letter I and the letter L.

So Drew Smith, I, L at Outlook.com. And so if you're looking, you're looking at. And so if you're looking to help out Drew or maybe hookup, I don't know, like you, you have all these random hookups. Maybe you're going to, I have a feeling that because after people listening to you this episode, they're going to like also be emailing you to possibly hook up over here in the same area. I don't know. But Drew Smith, I.L. at outlook.com, you're looking for advice on how to go about fully dressing, right? Yep.

That's where you're at. Are you looking now, like as far as relationships are concerned, would you want to try dating a guy at some point in your life or do you only see yourself with females? Do you have any idea of what if you could paint your perfect future like what it looks like or the perfect relationship? It could be either a guy or male or female. Whoever you're interested in. Now, if you met a guy that you were totally down with and you fell in love with, would you be ready to come out to your family? At that point, probably. So you feel comfortable and coming out to your friends besides all the people that you hooked up with and that one girl and the one guy friend of yours that you hooked up with by accident.

Does anybody that you haven't, does anyone in your friend's circle know? Nope. Nobody does. Nobody. So it is a secret life because I know why I asked you that earlier and you're like, it's a handful of people to kind of know, but not really. No one that you haven't had sex with knows. Correct. But you would be okay with letting that part of you, putting that part of you out there?

If, you know, for the right person, yeah, definitely. Yeah, listen, I get that. If you're just strictly having sex with people, like it's not like everyone talks about their sex life openly to everyone anyway, right? So what is it anyone's business? But if you're dating somebody that happens to be a guy, like, if you, you know, you have to make a choice whether you're going to keep that on the downlow or not. So you would be comfortable letting people know.

So do you go, are you like on when you're like on dating apps and stuff? Do you have yourself on dating apps for men and for women? Yes. You do? Yes, yep. Mm-hmm. And so you've only gone on a couple dates with guys. How come that has never happened for you?

Just haven't found anybody that, you know, looking more from four more than just a hookup. Right. Okay. But are you always on hookup sites? Like maybe you're on the wrong, like, I don't know. Probably on the wrong sites. Yeah, like maybe kick you're not, they're not really looking for dates, you know, I don't know.

What about females? Like where do you go to hook up with them? Same. I think it's easier or it's been easier to just go out and find females and it is males. Yeah. And were you always using protection with people? Some. Mm-hmm.

You know, I'm tested and everything and been good, but just the difference between protection, not protection. it's been some people I've used protection with and some I have it. Now, when you don't use protection, do you ask about testing or does it just sort of happen? So you do that up front? Yep, we talk about it up front and we make sure that everybody is safe and good to go. That's cool. So listen, I'm going to give your email out again, right, so that people could email you if they want.

Listen, you're into older guys. He's 32. What's the oldest you've ever hooked up with? 70. No way. Yes. How is that? Tell me that story real quick. Let's see. He was 70 and I was 20. Met on Craig's List and met him at his house. I went there as a guy.

Met him at his house. Good shape, tan, kind of taller, fit body. Yeah. A nice hairy chest. Yeah. And another guy that we had made out, he was dominant. He knew I was submissive. So we were making out.

And I was sucking him and I bought him for him. And he came in me. And then he ate me after that. And now were you like, is it a turn on for you that this guy is so much older? Is that like a part of it as well? Or just doesn't really matter? Probably a little bit of both Because he was older

But also because he was attractive And he was attractive But you also like the older thing So you don't have any limits As far as how old a guy could be No No long as I'm attracted to him Age doesn't matter

And now how do you know that you're attracted to these guys Ahead of time Is there typically you swap picks and stuff Yes We would exchange pictures Or meet somewhere Before or whatever Just to make sure that everyone is

Who they're say they are. Right. All right. So listen, Drew, like again, if you want to give, Drew is at the place where he really needs to fully cross-dress, right? So you really, because I really believe, Drew, that you're going to get a lot of emails just from guys that are, like, older that want to hook up with you or maybe send dirty picks, whatever. But what you're really looking for more so is advice, right? Yes. Any advice that anybody would be willing to share. Right, on how to fully cross-dress. There's going to be the great thing about podcast.

First of the email is Drew, D-R-E-W-Smith, S-M-I-T-H-I-L at Outlook. Now, the great thing about podcast is they live on forever once it's posted, right? So you'll get emails after it airs at any time, right? I don't know when I'll air it, but I'll keep you posted. It'll be in the next couple of weeks, right? And then let me know how many people email you. I hope you get a lot of people giving you advice. Well, definitely do.

Okay. Thanks so much for calling in, Drew. Thank you for having me. Okay, take care. Have a nice holiday. You too. Thank you. 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 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. 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. Hey everyone, strictly anonymous podcast is looking for people to call into the show. So if you lead an interesting, naughty secret life that you want to talk about while remaining

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