Strictly Anonymous Confessions - 372 - Drew has a Fetish for Much Older Men

Episode Date: January 25, 2021

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. **He's looking for cross-dressing advice, you can email him. He gives out his email address at the end of the episode.  **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

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Today I'm on a guy named Drew. Now, Drew, I think I taped a while ago. I'm trying to get all my episodes out. I think I taped him around the holidays. But anyway, 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. Drew, you know, started out, you know, into guys. But he also has this other thing going on where, and we talk a lot about when his younger years,

when he was like going into his mom's room and trying on her panties and getting turned on by that. And then he tried on her bras and getting turned on by that. So he 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 i mean you should hear this story about what he did on a family vacation like he split from his families and went and had a major hookup and 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 craigslist 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 uh 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. The oldest guy he's ever been with. It was pretty old. He talks about exactly what happened with that guy and a whole lot more. So, oh, he 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'm always impressed by someone who could deep-throat. 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. I mean, I know you said you were going to be parking soon. That's why parking was in my head, the word.

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, right? You're, I mean, the gist of what we're going to talk about today because you laid it out in an email to me is your bye. You've had like 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 foursums 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 by guy, right?

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, right? But let's start when you're really little. 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, you know, less than a handful of people know about anything. So, you know, 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, like what's a long term? term relationship you've had with a female? A couple of years.

And when was the last time you dated a woman? Probably early COVID. Oh, so earlier this year, but it didn't last? Didn't last just with everything going on. It made things tough, so. But I mean, when was like your last long-term relationship? Probably about over a year ago. Right.

And how long were you with that woman? probably about nine months no long term I mean years nine months at least I would say the longest or the most recent long term I had was probably about four or five years ago right 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 she did not she did not she did not and now when you're with these women right that don't know. Do you cheat on them behind their backs with guys or are you able to just keep that on the

debt? Like do you just push that aside when you're dating a woman? A little bit of both. You know, early in our relationship, you know, it was just you know, very faithful and, you know, just her and I and, you know,

probably about halfway through you know, started, you know, beating some guys on the side. And, you know, kind of went off from there. Right. Okay. So let's start in the beginning, though, because I know that,

and, you know, before you even started hooking up with guys, because you hooked up with guys when you were pretty young, too, right? But, like, 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. Mm-hmm. And what did, like, do you remember that first time that you were, like, thinking about, like, do you remember how it kind of popped into your head? Yeah. You know, when you're around that age, you're, you start getting curious about things and start having different thoughts and feelings about things. And, you know, is the Internet age and checking things out.

How old are you now? 32. Oh, okay. You're young. Mm-hmm. So then, you know, start checking things out. And then one day you're home alone. And, you know, I start getting curious and checking things out.

And that was the first time that, yeah, that I tried on panties. But now because you had, you know, listen, I grew up in a very different time, right? Because I'm like 51 or whatever. You know, like we didn't have the Internet back then when we were young and curious, right? So now for you, because you did, right? You're 12 years old. Were you Googling like guys in panties or like were you watching like porn with that kind of stuff in it? Like what made you put that connection like, oh, I like girls panties and I want to try them on?

It was. It was the internet age and, you know, 12, 13 years old. You start getting curious. No, but what did you get? I know everyone gets curious, but like I want to know specific like you, you know, as you're 12, like what leads you to seeing men dressed up in pants? or was that something that you went to look for? Did you stumble upon it? Stumbled upon it.

Just checking out websites and seeing different things on there. You know, happened to stumble across that. And it got me excited and more curious about it. So, you know, one day when I was at home alone and, you know, I had an opportunity to try it out myself. And I did. So you go into your mom. drawers and you take out like a G string or a panty and like you put it on and does it turn you on like do you jizzing it do you put it back like what is that first how does that first go down go into detail the first time the first time I put them on and checked them out it was a I still remember vividly there was a black lacy thong and just tried it on and poured around and kind of just sat down and kind of just sat

in it and, you know, rubbed myself a little bit and just, you know, trying to figure things out and trying to figure myself out. And, you know, that was all that really happened the first time. Mm-hmm. So nothing, nothing too crazy, just, you know, trying to, like I said, just trying to figure myself out. But then it progresses, right? Yes. Yep, then it progresses.

And so go and progress. Tell us how it progressed. progress. So, you know, more times when I'm home alone and, you know, get a chance to continue to experiment and feel myself out, it progresses into more and more. And then I tried on, you know, bras and, you know, more just to lingerie things. Oh, you did go that far into it. 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 like 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 um I was home alone so you know I would I would go in there and steal them or borrow them and then you know like I said put them on and you know eventually it would progress to where I was you know getting myself off and wearing just the panties and then

And, you know, I wanted to see what else, you know, I could progress too. So from there, you know, again, just wearing the panties and then wearing the bra. And continuing to, you know, experiment. Yeah, I get it. But wait, let me ask you. I'm just going to move you along. So are you, are you, like, does this freak you out that you're into this? Like, are you wondering why you are?

put it to get like did you start to also think about guys at this time i did um i did start thinking about guys at that time um it didn't really i don't know if it's normal or not but it didn't really freak me out um no i don't think it that's yeah i always ask that because i wonder i feel like yeah that's great i think some people would be maybe confused you know sometimes there's confliction about it sometimes there's not you know i always like to just ask that question because who knows, you know, I don't know. So you felt comfortable with it. I mean, it was like your own secret thing,

but you were cool with it. Yes, yeah, felt comfortable with it. You know, didn't really know really anything about cross-dressing. Right. Uh-huh. You know, anything like that at that age. But it was something that, you know, as I'm doing it and, you know, starting to figure some things out about myself,

I felt comfortable in it. So, you know, it started being more and more comfortable, each time. And, you know, again, it was that. And then, you know, also seeing things of, you know, 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 experiences and maybe some normal pass.

Yeah, well, I don't know what's normal. It was normal for you. I mean, this is like how it started, right? And then, so now I know that when you were young, I mean, 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, you know, 14, 15, lost my virginity of 16.

Mm-hmm. And then now, how did the guy on guy actions start? So, again, you know, part of the Internet age, the old school AOL chat room. just in there chatting one day and and you know I would check out you know mail rooms and and those kind of things on 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 I mean he was older than me so he was older i thought you said he was your same age yep he was he was two years

older than me okay he was just out of high school um found out we didn't didn't know each other uh-huh so it uh for me i was comfortable with that you know with my first time and and you know nobody really knowing or me even really knowing what was going on yeah and now where are you yeah exactly where do you 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, you know, kind of check each other out and make sure that we're legit and were interested. And he had kind of known from our conversations that it was something that was very new

to me, but never, you know, partaking in that. Yeah. I've never been with another guy. Had he ever been with another guy? He had. Okay. He had. So we were supposed to meet there and something happened.

So it didn't work out that time. And then a balsy move on my part, the next time we met up, it was in the middle of the night. And I had him come to my house, which was very risky because my people, my people, parents were home. But again, it was, it was midnight, one o'clock in the morning, and I had him come over. You sneak up through the front door, or did he climb through a window? I mean, how did he? We actually met out in my front yard.

I 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 up outside? We just, we 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. 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 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 when I 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... Right, okay. And when you're that young, listen, I remember banging guys in, like, their cars, like, my boyfriends in front of our house. Like, I mean, when you don't have any other options and you're super young, like, you do show. like that. Like, I remember doing crazy stuff. You know, looking back, it's like, wow, like, you know, because an older brain thinks things

through more. But I think when you're young, you just don't think, like, oh, my God, like, my mom could wake up and walk right outside, you know, it was like, you know, when you're in it, it just makes sense, right? That's what, that's the only where, 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, you know, anybody can wake up at any time and walk outside and see something that they probably would never, you know, expect. Unsee. Well, they'd never be able to unsee that. So you blow him. Do you see him, like, regularly after that, or was that, like, a one-and-done situation? That was a one-and-done thing.

You know, it's something that he wasn't interested in, and, you know, we just kind of went our separate ways. Okay, but then now, because I know you have like 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, you know, and you've talked about it on previous episodes, you know, Craigslist became a huge spot for me to visit. Yeah. to try to find hookups. Hookups and different guys. 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 interested in older guys. So that was like a thing that you were into? Yes, yep. Attracted to older guys. you know just wanted to take out the risky part of you know really anybody knowing the other side of me yeah yeah right so older guys i didn't have to worry about it but also at the same time was

guys that i was attracted to and him attracted to right and so what's your type so older what else do you look what else did you typically look for older guys um in somewhat good shape You know, I like the hair of your chest, you know, just confident, older guys that are in good shape. Mm-hmm. But, like, do you like guys that were really well hung? Did you like guys from different race? Like, did you, you know, did you have any of that kind of specific thing? I've had guys a different race.

You know, older guys are guys I'm attracted to. I also like black guys as well. Right. So you do. I've been with some Asian guys. Mm-hmm. You know, I mean, who doesn't like a big cock. Yeah, I mean, that's what I was getting at.

Right, I think you're right. Most people do, right? Okay. Are you a top or a bottom? I started out as a top when I started meeting with guys and now I'm a bottom. Oh, interesting. So like a switch. That's what they call it, right?

Yes, but 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?

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 topped, met him through either an AOL chat room or Craigslist. I think it was through an AOL chat room. Right. Older guy had met in a male, all-male chat room. 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. Oh, really? And now is this a time when, like, through high school when you're dating? Did you have a girlfriend at that time?

I did have a girlfriend at that time. So this was, like, all in the down, though? She didn't know. Yes. Okay. So you're hooking up. Now, was he a single guy? Was he a gay man?

Like, what was his story? He was a gay, single guy. Oh, okay. lived by himself. And so we had, you know, we had kind of developed, I guess, and how 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. Lots of oral.

I would top him. You know, he taught me a lot of new things. And obviously experienced a lot of new things. a lot of new things and it was it was a fun time for that year probably for him too i mean 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 was like right i think he enjoyed it as well yeah yeah yeah so now would you like make out with him i did not um didn't make out with him um i think i was just too nervous too or something new um i've never done it before i mean we we kissed

but never, you know, never fully made out or anything. Right. 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. You know, after we kind of had our thing for a year, you know, during that time, we met a couple. other guys as well. Mm-hmm. And then, you know, Craigslist took over the world. I'm looking for, you know, for different hookups. And from there, I found a lot of different things on Craigslist.

As anybody who's ever been on there before knows. But you tried all of them? Like, what other things did you find and try? Let's see. I've tried at that point. You know, I was out of high school and into college. I tried, you know, met. with some couples.

I was a single guy. I 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 were both of them? Had both experiences where the guy was by, the husband was by, and then had experience. 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.

But wait, I want to start up with that relationship. because I think that that's kind of major that, like, you finally, like, this is the 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. We, you know, we were dating. Well, didn't you fuck guys in front of her?

I ended up getting fucked up. Okay. So you're saying, like, you didn't just have a conversation and let her know about it, kind of just how. happened? Yes, kind of just happened. We were drinking and talking and the conversation of, you know, what are some fantasies of yours and what's some fantasies of mine? And, you know, just kind of threw out different ones. And, you know, some people will share fantasies that they know aren't going to scare anybody off. Yeah, totally. Uh-huh. We got to the point where we just shared our fantasies without worrying, you know, that we were going to get judged by the other person. Yeah, that's great.

You felt comfortable with each other. She was telling you her fantasies, too. 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 some experiences with during that time.

But did she know that you had been with guys before, Or did you play it off? Right. So you played it off like you were right. Okay, that this would maybe be something that would be hot. 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, 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. I mean, we made out and touched. We just met out at a bar. nothing too crazy just wanted to get comfortable with each other who's making out are you making out with the woman or the guy and she's making out with the girl like when you say making out who's making out with her and she was making out with him

there was no bisexual stuff going on that night but then probably about actually the week later we had met them at their house to meet up and hook up And then that's where, you know, at 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 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. Mm-hmm. And was that like an amazing experience to have that threesome with your girl?

Yes. It was a lot of fun. We both enjoyed it. Again, it was an older couple than us. How much older were they? 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. you know, meet some people that were a little bit closer to our age. Okay.

They 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 you know I still don't think she ever thought that I was you know fully bisexual and attracted to the guys I think she just thought it was a sexual thing and you know 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 that I was fully bisexual so now your next threesome with the other guy

with the 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, you know, and I got, I was a bottom that night, both nights. Oh, so that's when you. first because so you were like a switch when you were younger right because i typically used to think like it's like most people are really have one 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 do 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 um when i you know i'm looking for guys i mostly look for tops um i will top occasionally if yeah Yeah. We got to that point, but I would definitely prefer to be a bottom. Right. Okay. So you have those threesomes with that girl. Why would you break up with that girl? That's what she usually. You should be married. 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, you know, 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. Right.

Okay. So you continue after you guys break up. I mean, how many other, did you do it a lot or were those the 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 or in three things. couples and stuff, like, and you're always getting people on Craigslist?

Yeah. Yeah, that was the, you know, it's kind of when everything took off. You know, I was, you know, finding guys on Craigslist and some couples. Didn't you have something that happened on a family vacation? What happened on the family vacation? Oh, crazy times and, you know, Craigslist coming in clutch. So this is when you're younger, right? We're going back a little bit now.

Yes, I was still in college. Yeah. I think it was, you know, in the summertime. Yeah. Florida. Now, how big is your family? You have a mother and a father, and how many brothers you got? I got three brothers.

Okay, so you're all on vacation someplace. Yep, all on vacation. We're down in Florida and, you know, enjoying the weather. And, you know, at that time, you know, old enough, I'm 21, 22 years old, kind of old enough to enjoy things on my own. Yeah. So I'm looking on Craigslist and just, you know, looking to see if there's anybody in the hotel.

You know, 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 and saying e-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, you know, fit guys, good-looking guys. You know, older, in good shape. And what about you on scale of 1 to 10? Probably about 7.5. Okay. At that time, you know, I was in a little bit better shape than I am now. and, you know, in college at 22 years old. Yeah.

I'm looking pretty good. Right, right. So they're looking for a hookup. You go in to the, you go to their hotel room? Yes. Yep, I went to there. 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? Uh, only saw them once. Um, I was there for about an hour. Um, it was the middle of the day. I was there for an hour. Um, one was a top and one was a bottom. Um, so were you the same, you were in between? I was in between both of them. Oh, wow. Right. So like, uh, so you're fucking one guy in the ass while the other guy's fucking you in the ass. Does that go down? Like a trip. I was getting, I was getting fucked while sucking the other guy. Oh, okay. Mm-hmm. Um, so we, we had done that. I blew both of them. It was the first time. That was the first time I had eaten the guy out and also got eaten out by a guy. Oh, so like his ass?

Yes. Okay. 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 to your brothers, your parents. Like you had just eaten ass, got fucked, fucked guys. Like, I mean, oh my God, if your parents only knew. No, no, no, nobody knew.

Of course, but I'm just saying imagine. Like, you know, you just come back like nothing happened. But meanwhile, you had like a whole hour of like crazy sex with guys. Yes, I don't think, you know, nobody knew. I'm just off on my own and nobody's expected or even ask any questions about where I was. Yeah, of course not. No one would ever think that's going down, right? Nope.

No one thought of 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? Like 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. Right.

I don't think there would be any guests or, you know, maybe, well, I kind of had, you know, suspicions and all that. But I don't think anybody would have any clue. Right. 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. to even more things. Right. So then what do you go, like, 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 couples, 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. You know, I enjoyed eating, eating them out, as well as getting eaten out. So it was, it just opened me to more things

than just, you know, blowing a guy and being a bottom. Right. And I'm sure, because you're still on Craigslist at the time, because listen, you know, my show was based through getting guests on Craigslist for a while. And then, you know, Craigslist went bust, you know. 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,

you know, once I got into college and, you know, kind of got more freedom to go out and do things without being questioned or asked about where I was going. You know, I started posting more ads and getting a lot of responses. Well, I could imagine. Now, would you get to specific into all the kinky things that you were into when you would post your ads? I posted that, you know, 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. So, you know, and submissive.

So whatever, you know, they told me to do or wanted to do, I was pretty instill in, pretty accommodating. So I was I was posting those things as well as replying to the post that caught my attention. Right. Now, did you ever do any kind of wearing? Because listen, you know, we started talking. When we first started talking, we talked all about you trying on lingerie and panties and stuff like that, right? And 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. Right. Now, did you ever dress up when you were with anyone? Did that ever, like, did you ever bring those two, like,

things together? Um, there, there were some guys, uh, that were into panties, um, that wanted me to wear panties and, uh, and I would. Uh, the most that I've worn for, for a guy is, is panties in a bra. So, yeah, there was guys, and then that's, you know, 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. Right. And then you started doing that? Yes, for guys that were into that, I would definitely wear panties and bras to win. 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, you know, guys, I would, I really liked it and really enjoyed it. So it was definitely one of the many kinks that I had explored.

Lord. Right. Now, you know, all these all sound like, you know, 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, I mean, we were hooking up quite a bit. But then we would, you know, go and grab something to eat or grab something. a drink and kind of just hang out while also hooking up it wasn't just a walk in hook up you know do our thing then walk out it was a little bit more than that so it was uh he said I wouldn't call it fully dating you know boyfriend boyfriend but yeah you know it's definitely more than just uh more than just hooking up now did you ever get cop any romantic feelings with any of these guys uh he was probably the closest one. Mm-hmm.

Just because the guys that I was meeting and talking to, they were, you know, they were looking for just hookups. And at that time, the same time, I was too. Right. So I 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 or 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 and now was it the only that one guy that you'd fucked for like a year like or was there anyone else over those years that you were hugging with guys did they ever last that long too There was a couple guys that lasted, you know, roughly a year. Mm-hmm. Right around there and or guys that periodically, you know, throughout my time, we hook up or occasionally hook up.

But, you know, 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, like 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. How did that happen?

I was hooking up with the guy that he was hooking up with. And then that guy mentioned he wants to have a threesome. I mean, they're not going to turn down a threesome with good-looking guys. So, said yes, and we both show up, and I think we're both very surprised to see the other person there. 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 town, a guy from high school, a guy from your college.

A friend from college. Wow. And so you, and did you have any idea that he was or no? No clue. Right. So you're hooking up with a guy, 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 walk in and he's naked with a with a nine inch cock Oh my god I'm you know shocked in shocked even more and then obviously having a good time. Right.

Shocked because you know him. Shocked because he has a nine inch cock, right? Yep. Yeah, that's interesting. So guys like, like you like length too, because I would say as a woman, right? 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 like what's the nine inches is it so is it more of like a visual thing a visual thing um you know obviously feels different when i mean he was nine and pretty thick as well yeah so obviously blowing him and having a mouth full yeah then also having an ass full as well yeah it was is amazing different feeling yeah different feelings and obviously felt good. Do you deep throat? I have. You can?

That's a thing. Like, I can never deep throat. I don't, I mean, 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? Well, you know, 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. You know, I more so love being face-fucked, so it's different. 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, you know, 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, like,

because I just wonder, I mean, I've never been able to deep throat in my life. I've never went on a mission trying to figure it out. Like, and I've had a couple women talk about it, and I'm just curious, like, is it something that you were like, you saw it and you were like, oh, I want a fucking deep throat? And then you, you know, looked into how you could do it or how, you know, or how does it 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 lean your head back over? Someone once said this, like you lean your head back over the bed,

like, 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? 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. Right. 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?

Right? I would assume because you're like submissive, right? So there's something about like that person, like you said, being face fucked or just shoving their cock all the way down your throat. If you're submissive, that's probably super hot right? Yes, yep.

I love being told what to do. And whatever guys have asked me to do, I've always done it. Right, ready, willing, and able. Yes. Right. And now I know that you say that you want to fully cross-dress now. Like, what's stopping you? And what does that mean fully cross-dressed meeting, like leave your house that way?

Or, you know. 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, you know, I've 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 like 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. So like 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, you know, been into the panties thing. You know, obviously when I was younger and putting on bras, none of them fit.

Yeah. They're all too big for me. So just, you know, not knowing where to start and, you know, the makeup and the hair and, you know, what looks good in an outfit and those kind of things. You know, I just want to make sure that I do it right. Yeah. And, you know, just make sure everything looks good, you know, 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. Right. 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're dressed up as a guy,

but you have panties on underneath. Just had panties on. Right. And so now you're... 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. So I drove over to his house. What are you wearing on your feet? Just sandals. 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 uh he lived in an area where it was just him okay out in a secluded area so oh okay so worked out perfect but you're driving in the car with nothing on nothing on just just my phone oh my god thank god you didn't speed there right like i mean i would hope you did everything you could not to get pushed up by a cop right Oh, my God. Yes, about more driving rules I ever have.

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 the submissive. I mean, that is a, he's obviously a dumb if he wants a woman, a man coming over dressed in a panties, right? Yes. Yep. So, drive over, knock down 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, you know, rubbing up and down our bodies. And then he gets naked. I start taking, you know, all of his clothes off. So we're in his bed and I'm still in my panties. And he's naked and I blow him again. And he starts, he starts sucking me as well.

And then I turn over, doggy style, and he starts fucking me from behind. Mm-hmm. 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. Very.

So then, so from there we, you know, clean up. There's a thing, you know, my last caller, I don't know if you've listened to my most recent episode I just aired, which is Jamie, right? He's good, it's such a great fucking episode. He talks about a lot of different things. I think you'd like it because, and he had like a lot of, he had, he's by, right? So he talks about a lot of stuff. And he got into, like, come play, he said. And I didn't know what that was.

I had never heard of it. but he said basically that's like, you know, 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, cumbed on. Yeah. It's been, you know, cum swapped or I've had come in my mouth and made out with a guy. Yeah, yeah.

So that's, you know, that's extent of the come play that I've. Right. Yeah. I remember once I had a guy who called in who said like a guy, like, just on his face and he, went home with that and the thought of like having it all over his face was hot and i'm assuming he didn't put that word 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 was just like you know 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 you know 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 that's, yeah, go on. And then that was the end of it and, you know, cleaned up and went back home. Right. And so like 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. Right, yeah, exactly. Thank God by the time Craigslist shut down. Like I have too many, so many people just emailing me to be on the show I don't need it. But first couple of years, that's the way I got callers, right? Is from Craigslist. So now, what are you, like, 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.

Like, if you're a perfect scenario of your future, like, what does your future look like for you? As far as, like, dating? Do you ever want to get married? Did you do you see yourself as like do you have anything like where you could be like transgender or no like I mean 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. Uh-huh.

You know, again, I've gone to stores and tried on clothes and, you know, 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 the future holds. Right. Yeah, because it's interesting because I wonder, and I think a lot of people that don't know a lot about it, wonder if, like, 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. You know it's like

some and I would assume some people don't know right like for you you don't know. Do you feel like a man do you have that feeling where like you're a woman? When I am when I have my panties on I do. Right. I've

enjoyed you know the feeling of having a fully shaved body and the compliments of the guys have given me. Yeah. You know, when I've done that and worn panties and things like that. But, you know, to say that I feel like a fully like a woman, I think I'll know that or confirm that when, you know, the first time I fully dress.

Right. And now do you want to put a show? Because I know that you're like looking for advice on how to go about fully dressing as a female, right? 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, right? Whether they're cross-dressing currently or they're thinking about it like you, you know, 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, right? But maybe if you're looking for that kind of advice, maybe there's people listening that could help you.

definitely I've watched YouTube videos and Google things and you know just trying to find out what's you know what's best for for me and you know obviously any advice

anybody has is right so now listen if people are listening on YouTube because that's the easiest place to put information and stuff people could give you like if anyone has advice for Drew as far as like you know cross-dressing fully and how to go about it

whether it's you know like the best YouTube video or a blog or a Reddit right 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 or would you just want them to post information on YouTube for you in the comment section how would you want to go about them giving you advice um they can email me at Drew Smith I.O at outlook.com say that again Drew Smith. Smith.

I.L. at Outlook.com. Okay, so it's Jew Smith I, the letter I, right, and the letter L. So Drew Smith, I.L at Outlook. com. And so if you're looking to help out, Drew, or maybe hook up, which, I don't know. I mean, 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? I mean, do you have any idea of, like, 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. Right. 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 like comfortable and coming out to your friends? Do any of your friends know about it besides all the people that you hooked up with and that one girl and the one guy friend of yours that you, you know, hooked up with by accident? Does anybody that you haven't, like, is anyone in your friend's circle no? 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 Kind of know, but not really. No one that you haven't had sex with knows.

Correct. Right. 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. Right. Yeah, listen, I get that Like 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. And so you've only gone on a couple dates with guys. I mean, 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, you know what I mean? 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 girls, females? Like, where do you go to hook up with them?

Same. Do you have a preference? Like if you would. Just going out. And I think it's easier, or it's been easier to just go out and find, you know, females that it is males. Yeah. And what about in this COVID world? Who have you been fucking lately?

Nobody, unfortunately. Oh, my God. Right. And do you, were you always using protection with people? Some. Mm-hmm. You know, I'm, you know, tested and everything and been good. But, you know, just the.

the, you know, difference between protection, not protection. You know, 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 like, does it just sort of happen, right? 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. Right. That's cool. So listen, I'm going to give, like, 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. Uh-huh. Met on Craigslist. And, yeah, he's been one of the handful older guys that, that, I've been with. No, but like, tell me what happened with him. Met him on Craigslist.

Met him at his house. I went there as a guy. Met him at his house. Was he, like, in good shape for his age? He was. Okay. Good shape. Tann, you know, kind of taller, fit body.

Yeah. He had a nice, you know, hairy chest. Yeah. And, you know, another guy that, we had made out. He was dominant. He knew I was submissive. So, you know, we were making out.

And I was sucking him and I bought him for him. And he came in me. Uh-huh. And then he ate me after that. Right. And now, were you, like, does, is it a turn on for you that this guy's, like, 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. Right, 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, as long as I'm attracted to him,

you know, age isn't... Age doesn't matter. And now, how do you know that you're attracted to these guys ahead of time? Is there typically, like, you swap picks and stuff? Yes, yep. We wouldn't exchange pictures or, you know, meet somewhere before or whatever,

just to make sure that everyone is who they say they are. Right. Do you do a lot like now because it's COVID and no one's meeting up and, you know, and stuff? Do you do, like, online, like webcaming shit with people? No, no, just not. That's not something that I'd much rather have the real thing. Yeah, yeah, yeah. But, you know, hopefully, hopefully COVID can go home down here shortly.

Yeah, yeah, exactly. It's so terrible. All right. and 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, you know, 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, right?

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, you could, the great thing about podcast is they live on forever once it's posted, right?

So you'll get emails all the, you know, 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 letter. 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 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. 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.