Strictly Anonymous Confessions - 1073 - FETISH FRIDAY: Christopher was “Groomed” to be Into Crossdresser and Into Guys?!

Episode Date: March 28, 2025

Christopher was “groomed” to be into crossdressing and into guys and he called in to talk all about it. Tune in to hear all the details including how and when his male neighbor got him to start ��dressing up,” the girl he met in college and all the freaky things she got him into, their first mfm threesome and exactly what went down, the next threesome they had and how he hooked up with the guy this time, how he then starting hooking up with guys solo and dressing up for his girl,  what she made him do while dressed, how and why he would stop dressing up, how and what got him back into it in his twenties, the blowjob he gave to a stranger while dressed up and exactly how it went down, how he started going out dressed as a girl in Vegas and all the guys he hooked up with while there, his first bottoming experience with two roommates and exactly what went down, the professor in college he hooked up with and how that happened in the first place, how and when he crossdresses now, how he met his sugar daddy and what their arrangement was, the trans girl he hooked up with and what went down, the dom girl he hooked up with and what went down,, the guy friend he hooked up with who didn’t know it was him and what went down plus a whole lot more.  **To see anonymous a pics of my female guests + get TONS of exclusive CROSSDRESSER and or HOSER episodes and content + hear all the anonymous confessions, join my Patreon Crossdresser tier it's only $8 a month for Hosers and $10 a month for crossdressers (you get also get Hoser episodes too!) and you can cancel at any time. You can sign up here: https://www.patreon.com/StrictlyAnonymousPodcast 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 confess while remaining anonymous? Call the CONFESSIONS hotline at 347-420-3579. You can call 24/7. All voices are changed. Sponsors: https://butterwellness.com/ For 20% off your Butter Wellness perineum massager use code STRICTLY https://beducate.me/march2025 Use code anonymous to get an additional 10% off the campaign’s current discount - that’s 60% off 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/Strictlyanonymouspodcas Learn more about your ad choices. Visit megaphone.fm/adchoices

So if you got an interesting, true, naughty story that you want to talk about while remaining Anonymous, send me an email, strictly anonymous podcast.com, or just go to my website, strictly anonymouspodcast.com, and click on be on the show. If you have a confession, you want to get off your back, call my confessions hotline. 347, 4203579. That's 347.47.4-203579. My confessions hotline can be called 247. 4-7. You have four minutes to leave a message. If you need longer, just call back. I will edit the calls together. I change all the voices over there as well. They all get aired on my Patreon and some of them wind up on a Confessions episode. Now listen, since this is a fetish Friday episode, what's great about my Patreon is I also have two separate tiers. Each tier, whether it's the hoser tour or the

Crosschester's tier, it gets one extra episode a month, an exclusive episode. So the hoser tier, it gets one extra exclusive hoser episode and the cross-dressing tier gets one extra cross-tressing episode and the one extra hoser episode. So hoser tier is $8 a month, cross-dust or $10 a month. It's very specific. What's great about that is that you don't just get the episode for the month that you sign up. You get access to all the episodes that I aired before, right? So for $10 a month or $8 a month, You're getting access to probably 50 episodes. I don't know how many years I've been doing Patreon, but you're getting 12 extra episodes a year,

a couple of years. We're talking about like maybe 50 extra episodes, specifically on your fetish available to the minute you sign on, which is a great deal. You also get access to my Discord, which has a hoser and cross-dustre search here as well. Now listen, if you're interested in signing up for SDC, which is like the most popular online dating website for adults,

It's SDC.com, the worldwide. You can now sign up for SDC. If you use My Code 37712, you're going to get a free trial. So if you want to check it out, SDC.com, use My Code 37712, or just go to the description and click on the link. The thing about SCC that everybody loves is it's not just a place to hook up, right? Like you could post picks, it's an online date adult website. But it also has all the munches and the meet and greets and the,

parties and all that kind of good stuff in your area as well as in every area. So if you're traveling and you want to meet other cross-dressers like you, maybe you could look for them over an SDC. You get a free trial, click on the link or use my code 37712. Okay, today I have on Christopher. I have this feeling that, you know, I probably shouldn't have said one word with Christopher. He was just going on and telling his stories. But I did cut him off sometimes and ask him some questions. He was kind of like his kid that was like groomed when he was younger, he used that word. And then he seemed to be groomed for the rest of his life. I don't know. A lot of his stories were kind of fucked up, but crazy. He had one crazy story to tell after another, and he just did his thing on this episode. When he was

young, some guy in his neighborhood got him to like dress up like a girl. And he continued to dress up like a girl throughout his life. He hasn't done it in a while, you know, but he did do it a lot of times. and he hooked up with guys a lot of times. It didn't start out with dressing up and hooking up with guys. It started out with him actually having a freaky girlfriend when he was younger and they had like threesomes with guys and threesomes with girls. And that's when he realized he was into hooking up with guys. And he talks about all those experiences and sucking dick and getting his dick sucked.

And then being a bottom. And then he started going to adult bookstores. I mean, this one crazy freaky girlfriend, he had made him do a lot of things. Eventually he started crossdressing again and dressing up like a girl and going out. And when he did that, he could hook him. up with a lot of guys, which he did. He had a lot of hookups while he was dressed as a girl with a guy. He also hooked up with a professor. That's a fucked up story. Wait till you hear of the professor that he did something with for a passing grade. He also had a sugar daddy that he hooked up with for a year.

Then he also had a trans girl that he also hooked up with. And then he had a Dom girl that he hooked up with. He's full of one story after another. Like I said, I do interrupt him a couple times and ask some questions, but I probably didn't have to because he was a very good storyteller. I do have a picture of him dressed up over on my Patreon. And he will be on my Discord. So if you're freaky like Christopher, I want to meet a guy like him, he's a freak. He's over there. Okay, so signup, Patreon.com slash strictly anonymous podcast. Anyway, I'm going to be right back on with Christopher. Hi, Christopher. Welcome to the Strictly Anonymous podcast. How are you today? I'm fine. How are you, ma'am? Good. Christopher, I'm just going to read what you wrote because it's kind of funny.

It's like, you want to discuss your journey into the kingdom, into kingdom from grooming and MFF, M M M MF to frequent cross-dressing to Dom, Sugar Daddy, trans girls, a professor in college for a passing grade, and more. Okay, oh my God. I'm going to get it all in in this hour. I'm telling you, Christopher, because the word grooming is so fucking funny to me. I haven't talked to a guy who had a sugar daddy, but that's fascinating to me. So let's go.

You know, I don't know if we should start. I don't know who came first, the banging your professor for a passing grade or the grooming or their sugar daddy or their cross-dressing. Where'd I count for us? The grooming? The grooming? Like you were groomed or you're grooming someone? No, no, no, I was. You were grooming. Okay. But let's go all the way back because you also are into cross-dressing. I was the one groomed. Yes.

Okay, okay, but like let's go back to like your cross-dressing. Do you consider yourself a cross-dresser? At one time, I did. Now, now not so much. Really? That's kind of interesting. I've never talked to a crossdester who like had a fetish for crossdressing that it never, that it went away. It's interesting. Well, maybe it went away because I think my body type change a little bit. So you don't, you're not passable anymore? I could be if I shaped and the legs aren't as gorgeous as they were in their teens, 20s and 30s. Yeah, I guess. I don't know. I've talked to many crossdcessors. But listen, you're, oh, I'm always going to hear a new story. That's why I talk to so many people because you never know. Like I said, normally people are born with the fetish. They die with their fetish.

Eventually, some people, like, becomes like a comfort thing and not a sexual thing. But I rarely talk to someone where, like, they're not a cross-dust or anymore. But, like, were you cross-dressing very early on when you were, like, younger? Started with the grooming. Okay. So let's go there. You're obsessed with grooming. I'm kind of obsessed with it, too.

But, I mean, I don't do, like, incest stories. Like, what? I don't know who groomed you. No, no, no. It's nothing. Oh, no, it's nothing like that. So, started on a stormy day, riding my bicycle home. Yeah.

Right in my bicycle home. I'm like 12 years old. Yeah. And riding my bike home and it starts storming. And I'm trying to make it home. I'm soaking wet. My neighbor down the street, who was 17, he motions me to come to the garage. He says, hey, get out the rain.

Do it, don't know. You're going to get wet. And I'm thinking, okay, no problem. It's one of my classmates' brothers. So I pull up over there and he goes, come on, let's get you out of these clothes and put you on something else. I'm not thinking anything. Of course, you're only 12.

Right. I'm 12. We get in the house and I go in the bathroom. And he said, take everything off on my throat in the dryer because that's all we can do. So I'm standing in no clothes on. He comes and hands me a t-shirt and some shorts. I put the shorts on half my asses out. And I'm thinking, okay, this must be some of his sister shorts.

And I have shirt. And he goes, I'm back here. And I'm thinking, okay, it's a dude. It made it smell like a girl seem up. I'm 12. I'm not thinking that, you know, just walking out. Yeah, but this might be an R-A-P-E story, which I don't want to harp on. And I hope that this is, like you're not talking about this like this is hot.

Like, don't, you know. No, no, no. No, it's not. No, it's not anything like that. So I go in the room and he goes, hey, got some magazines on the desk. And he said, and it's like a sports magazine and some car magazines. And I turn around. I'm looking at him. And he goes, don't turn around. What? So you know how you get that bug that? Okay, somebody ranked. I'm 12, but I'm not stupid. So it's real quiet. And I hear something. Then I hear. out. And he gets a run out of the room. I said, that was weird. So he comes back in and he's like nervous. He said, your clothes are almost dry.

Like, okay. He goes, so you're not going to tell anybody this happened. I'm thinking, what happened? He goes, yeah, yeah, yeah, don't worry about it. Tell you what, let me give you $5. Okay. He said, so anytime you come over, you want to put on like those shorts or something, I'll get you $5.

I'm 12. I'm thinking, hmm. I mean, that was a lot of money. Yeah, sure. So I'm going back every day and it did escalate. We were, when I turned 16, it started being like $25. And it turned into lingerie and thigh hines and panties and all the thighs. It went on until I was 17.

And he went off to grad school. I mean, do you think he was like molest, molesting you? I mean, I don't, like, these kinds of stories are horrifying to me because I know, like, maybe by the time you're 16, you think it's consensual, but like you used the word grooming. So on some level, you know that he started to mind fuck you when you were too young to consent. So the whole thing is like fucked up. It is. And so forever, I didn't think of it that way. I just thought, oh, I did. The victim never does. And that's not your fault. It's typical that, you know, you think. And, you know, you think. And, you know, you know, You know, you just think it's like normal or you think it's your fault or you think you had something to do with it. You know what I mean? But on some level, you know it was grooming because you called it that. Well, because my friend who's now a psychologist. Yeah.

She said, when I finally, I told her about him and I was like in my 20s. And she goes, yeah, you were groomed. I said, what is that? She goes, you don't know what grooming. I said, yeah, but nothing happened. She goes, you never got touched. That said, never was touched. She goes.

But there's a psychological. logical part to this. She said, you got really comfortable wearing that stuff. And I said, yeah, but I just thought, you know, it was like, I'm still. I was in theater. I said, I was, you know, getting off on it?

Yeah, it was. Yeah, I mean, that's the whole thing. I mean, it was a sexual thing. Right. And that's what she said. That's what she said. So, so this is why are you to be, so like, really, like, that is, you know, that wasn't you, like, that's not a, like, that's why you're not a cross dress.

right? Because you were not a little kid who saw his mom's clothing and for some reason was like dying to try it on. You were groomed to put on these kinds of clothes and stuff. And so and then it imprints on you. So of course it's the type of thing that could actually leave you at sometime too because it was put on you. It wasn't something you were born with like other people, you know? Correct. Hey guys, guess what? Do you know that you have a G spot? That's right. Guys have a G spot too. And you want to know where it is? It's hidden right underneath your taint. Now, I'm sure most of you know where your taint is, but for those who don't, it's that tiny little super sensitive strip right between your balls and your asshole. Now, listen, callers have told me that if you stimulate your male G-spot, you're going to have what's called a prostate orgasm.

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B-U-T-T-E-R W-E-L-N-E-S-S dot com. Go there now and use my coach strictly to get 20% off your entire order. That wasn't you, like that's not a tip, like that's why you're not a cross-dresser, right? Because you were not a little kid

who saw his mom's clothing and for some reason was like dying to try it on. You were groomed to put on these kinds of of clothes and stuff. And so, and then it imprints on you. So of course, it's the type of thing that could actually leave you at sometime, too, because it was put on you. It wasn't something you were born with, like other people, you know? Correct. Yeah. Well, so after that, I thought, okay, that little episode of life is over. I go on meet this girl in college. Meanwhile, I've been having three sons of girls all through high school and get to college, meet this girl

who ran track at my school. I played a sport at my school. And we ended up running to each other, and we kept running to each other. We started dating. She said, one night she said, hey, are you, how kinky are you? I think I'm pretty kinky.

She said, okay, because I'm kind of a prank. Okay, that's ding ding, that's a perfect match. She said, which one of my friends would you like to walk? what? She said, in front of me. She said, we can do a reason. I said, so I said, okay, this is a trap. There's no way she's asking me this. I was 19. And I said, okay, I named the name. She goes, yeah, she's not in the ad. What about someone's though? I said, oh, sure. We started doing that. This is like three months into the relationship. So that went on for a couple months. And we went to, we were going to a Christmas party. at one of her friends' houses. Parents were out of town, and we're at the house, and we're kind of kicking it, and this guy walks in. And she said, God, damn. And I looked at her like, what?

And she goes, that guy, he's hot. I said, okay, well, what, you want to fuck him? And she goes, would you be mad? I said, wait, that's not part of the plan. She goes, but you're fucking my friend. I mean, hell. You know, it just be for fun. I say, sure, I'll go tell him, thinking, there's no way she's going to do this.

I'll bring him over. Of course, I didn't tell him. I'll bring him over. She goes, what did you tell him? I said, I just told him he thought he was hot. And she goes, no, I said, I'd fuck you. And the dude looked shocked. He looked at me, and I looked at him.

And I'm like, oh, this isn't going like I thought. So she grabs both of us and leads us upstairs. And we're at her friend's house. we get upstairs and I'm standing and looking at her thinking she's joking she's joking she's not going to go through with this she sits on the bed on top his pants looking at me and start sucking his dick I should have been mad but actually I was like

oh this is kind of hot stood there and watched her suck his day then she reaches under her fur pulls her panties off and tosses it to me and I'm standing there like oh, what is she reaches in her first, pulls out a condom, puts it in her mouth, and it puts it on a stick with her mouth. She never done that to me, but I was like, damn, that's skills. Well, the dude climbs on top of her, tries a kiss when she said, no, sweetie, grubucking. And he looks all nervous and stuff.

He slides in. He gets in about three pumps and finishes. And she's like, are you done for real? and he's like, yeah, and she goes, well, get up, you're done, just go, bye, go, you can leave. She's really rude to him. So he's leaving the room, you know, pull up his parents, leaving the room looking at me real weird. She gets up and walks over to me, and she said, that was hot, huh? I was like, actually, yeah, so we kiss.

And she whispers then to me, she goes, so how does this dick taste? So what? And she goes, his dick was in my mouth, and you just kiss me. she's grooming you too you're just perpetually being groomed and you have no idea that's funny so so like that

very next Wednesday night she calls and we're talking and she goes hey you ever thought about another kind of the reason like what other kind she goes what about me you and the guy she said because she seemed to enjoy the guy with me the other night yeah that's kind of a one off though she goes no you should try it

She goes, I mean, y'all, you guys don't get to try stuff, and we get to do anything. She said, why don't you try it? Just whatever. She said, you don't have to blow him. He could blow you. You could do whatever. I said, there's no way. Then, of course, she sets up one. I walk, go into a house. We go in, and there's a naked guy sitting on her couch. I'm like, oh, shit, I did not think this was going to happen. And we ended up having a three-sling.

I ended up, while I was. I was down, well, eating her, she's riding my face. He slides in behind her. And I'm like, oh, my mouth is really close to this. This is not planned either. And next thing I know, I'm sucking his steak. And it wasn't bad. You're like, why not? It's there. I'm like, you know, when in Rome, it was a Roman. Yeah, but can I just ask you a quick question? You're a very good storyteller. So I'm just going to let you do your thing. But quick question, before that experience. Like, had you ever thought about guys? No.

Okay. That's what was funny. I never even thought. I said, there's no way. I said the dressing or part, that was different. Right. Okay. So you had never thought about guy sexually, but now there's a dick in front of you.

You wind up sucking in. It wasn't that bad. Right. I was like, oh, okay. So he came and I was like, I felt it about to come. And I'm like, what do I do with? Oh, shit. I'm thinking in my head, the next thing I know, it's in there.

So I swallow it. I'm like, okay, she is ecstatic. She just has a bit. She's like, that is the hottest thing. Well, the three of us ended up all day exchanging. So that became a normal thing with us. Oh, with that guy and that girl. Well, no.

Oh, you and the girl would go out and just fuck other guys and do threesomes with them. Or girls. Oh, okay. That's where the MFF comes into play. So it's the girls and the guys. So the cross dressing came in one night. She's at a track meet. And we're on the phone.

And she's out of town, of course. And she goes, you miss me? I said, of course I do. She goes, so why don't you go out and suck a dick one night without me? And I said, what? She goes, go suck somebody's dick without me. She said, I know you want to. And I said, actually, yeah, because honestly, after I didn't,

it that first time and the second and third and fourth time that night, I said, oh, this is fun. You liked it? I actually did. And I was like, okay, I like the reactions. So I said, okay, fine. I said, okay, right, I'm just going to go out and find some random guys. I guess that because she goes, well, I have a plan. I was like, okay, you always have a plan.

she said guys are easy they'll fuck a in a tube if they got a chance she said go put on some really short shorts and go to like adult bookstore did she know about your little rendezvous with that guy in your neighborhood or actually no no I told her about okay so she did so she knew like the short shorts is from back then that's where she got the idea from right and she thought well I told her about that after the first MNF yeah No, I get it. But by this point, she's saying put on short shorts because that was your gear back then. Right. Yeah, okay. So she said, I have some blue jeans shorts at the house. And she said, when you get over there, call me. So I went to her apartment, got in, called her. And she said, cut them. What? So I cut them across the pockets. They were super short. Put them on. She said, how much is your ass is out? I said, uh, over half. She goes perfect. She said, now throw on some sweatpants because you don't want to drive around like that. Because if you get pulled up my cop, that's going to be embarrassing. Like, okay. And she said, go to a bookstore and just kind of walk around.

Somebody's going to want to holler. I'm like, a bookstore, that sounds grimy. And she said, call me when you do something. Can you do me a favor and get this girl to call me when we're done talking? I catch this girl. Holy shit. She's got some imagination on her. Okay, so she's directing you. Keep going. Sorry. Right. So I, so instead of driving to something in my town, I drove to a town about two hours away. I get there and I see a window bookstore. I go in and I said, okay, took off the pants, walked in.

And you know, you're getting these strange look from the guys that are looking at you like, why is this dude walking around with his ass out? Then you get to look from some other guys that are looking like, ooh, all that ass. Okay, this is going to be interesting. So one guy comes in, nice looking dude, comes in, and he looks, and he goes over to the section where I was. And he said, I like your shorts. Me, I'm kind of bold at times. I said, do you like my shorts or what's in? He said, the whole package, he said, turn around.

I turned around, and he goes, damn. And I turned around and I said, so what does your package look like? Me being bold, he said, well, I'll let you sit outside. We go outside. We sit in the car. He pulls it out. I blow in. And he says, oh, shit, you want to follow me to my apartment?

And I'm like, no, I think I'm going to go back home. He said, well, here's my number because we need to hook up. I was like, okay, took the number, throw it out, of course, put on my thing. and rode all the way back home, called her and she was thrilled. She liked to hear the stories. She sounds like a dude. You paused if she's not a guy. Was she a trans girl?

No, no, no. She's actually married now. She's a freak. She loved to hear the stories of what went down while you were there. Oh, yeah. Okay. So she was, she has married her and her husband are both by. Okay, cool. Want to have better sex and be more confident in bed every single time you get down and dirty.

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No, no, no. She's actually married now. She's a freak. She loved to hear the stories of what went down. while you were there. Oh, yeah. Okay. So she was, she is married her and her husband both by. Okay, cool.

So I go back home and everything. So that relationship lasts in a while and the real cross-dressing stuff came in around. I was about 23, went to Los Angeles, hanging out with some friends, and it was Halloween. Of course, everybody dresses up for Halloween. So I didn't have a costume. I hadn't planned on being there for all of that. I didn't even think about Halloween.

So I'm hanging out with three of my friends, and it's all girls. And they're like, oh, we have a party to go to. You should go with us. I'm like, okay, cool. They said, but you have to wear a costume, and it's probably too late to get one. So they're brainstorming trying to think of something, and they're like, wait. You could wear like a cheerleader skirt. I'm like, okay, put on a cheerleader skirt.

So they decided, okay, we got to shave you, da-da-da, get you ready, land up. Okay. I had never seen a, what's the thing they spray, like a spray gun to put makeup on? Yeah, uh-huh. Airbrush. So they airbrush makeup on and all that. I looked at myself, I was like, oh, damn, I don't recognize myself. I was pretty passable.

Mm-hmm. They put water balloons in a bra. You're being groomed again. Here you go. Always the innocent victim just being pulled along into all these things. You were just made to be groomed. So we go to the party and it's funny because the water balloons gave it a little bounce. Oh, my God.

That's funny that they put the water in there. That was smart. That was smart. But I was just really funny. It was really funny. I had the time of my life in a little bit. skirt and a sweater and a wig and full makeup. People thought I was really a girl. And did it trigger something inside of you? It was fun. So I was like, okay, this is kind of cool. Because people

were asking me to dance and I would say, I'm a guy. And they're like, no shit. You look sexy. Oh, yes, you don't care. My friend said, they don't care. They're looking at the booty and the legs. and whatever's between your legs, they don't really care at this point. Okay. So we get to afterwards, we go to breakfast. And we're sitting there, and I'm like, I'm in a breakfast place miles and miles away from home and in a damn skirt. And they were like, don't worry, you look like one of us.

Nobody's going to tell. All of a sudden, they got serious, and these guys came walking in, and they said, you're going to whisper. because these guys will beat your ass if they think you're a damn boy. I'm like, oh, look. So my friend goes, oh, you got to stop. She's on her period. And he goes, oh, I'm sorry, sweetie.

But he keeps his hand on my thigh. And I'm like, okay, this is uncomfortable. So we're leaving, walking to the car. And the other friends of mine are all hooking up with the guys. I'm standing there like, what the hell and doing this looking at me talking about So is your mouth on the period? And I'm like, oh, there's he went said.

So he sits on the car and wips his dick out. And I was like, oh, that's nice. And went right to it. Right. And I was at it and really given a porn blow job. My friend sees me doing it. She's a little shocked because she didn't even know. Yeah, of course.

And when he came, I kept going because it was good. And all of a sudden, I got pulled away and we ran to the car. We drove off. And everybody in car is quiet. And I'm sitting there like, okay, what? I said, what are y'all thinking? And she said that that was hot as fucking you'd owe me a whole explanation because I didn't know that was going on in your life. Because obviously that was not your first time.

So we ended up having fun at the house. I told my friend about it in Atlanta. She said, oh, no, you've got to come dress for me. That started us going out dressed. I would go out with her, and she said, oh, yeah, you are passable. And she said, you don't even need a wig because I'm kind of curly hair. I'm mixed, so I got a curly hair and all that. And so she would make up on.

I would go to Atlanta. Most of them I was in Atlanta. I was a bitch. But when you say your friend in Atlanta, was it that same girl that you were having a threesome with and shit, that same girl or someone else? Completely different girl. Okay. So a new girl, all these girls are just down with you dressing up? It was funny because I just happened to have friends that were, I had kinky-ass friends. Obviously. I think they, you all smell each other. It's like magnets, you know? That's, well, that's what she said. And that's the girl that's actually a psychologist now, which is funny.

Yeah, we all, like, freak smell other friends. Greeks and shit, you know, everyone finds their people. Well, she's actually, when we went to Las Vegas, and we get in the airport, and she goes, we're on the plane and she goes. So I'm going to tell you something. I said, what? She said, the whole town we're in Vegas, you're going to be a girl. Wow. I said, what?

And she said, I want you to be a girl the whole time. We're in Vegas. I said, how's that going to work? She goes, you're passable. You're going to have a slutty clothes. Nobody's going to give a shit. So we did. and nobody cared.

And I was there from Friday till Monday morning and had on nothing but little bitty shorts and skirts and end up sucking off several people. And it was fun. Same girl, we're in Atlanta. We got to a party. Meet a guy. And this is my first anal experience. Meet a guy and told him I was a guy. And he was like, oh, okay, okay.

We ended up talking, and he had my friend's number. He calls my friend the next morning and says, hey, can I talk to your friend? And she says, here, Chris, stop. Get on the phone. He said, hey, you want to come out of house? I'm like, okay, go over there. He's disappointed because, of course, I'm dressed like a dude, right? Yeah.

So he has on shorts and stuff, and I'm like, okay, looks like he'd be fun. I'm only thinking about head because I love doing that. Right. So what these guys ever give you had or are you one of those guys that just likes to suck a dick? Oh, no. The thing that surprised me most of all was the fact that when I started wearing skirts and stuff, that guys wanted to suck me off. Right. They wanted to see what was under and then they wanted to suck me off.

Yeah, it's not like they want to pretend that you were a girl. They love that you look like a girl but also had a dick. Right. Yeah. But the thing, what was, my drawback was I wouldn't kiss anyone. Yeah, okay. But all the blowing was happening mutually. It wasn't like you just blew guys.

Guys blew you too. But this is going to be your first anal experience, right? Right. Okay. Yes. So get over the house and we're talking and he's like, you can tell you disappointed. So I said, oh, I got an idea. I said, where's your restroom?

I go in a restroom, wet my hair, pull it back, and take off my pants and my underwear. and I had on a button down collar shirt. So found some lotion in his, some baby oil, and rubbed it all of my legs and came back out. I said, this is a spanner. He was smiling. So he comes over and tries a kiss, and I'm like, I don't kiss. And he starts kissing on the neck.

And I put his hands on my nipples because that turns me on. So he's doing that. And we're going and there's ripping all over me. And I'm playing with a stick. I pull it and I said, you want me to suck it? And he goes, hell yeah. Give him head. He nuts.

All of a sudden, somebody comes in. He goes, shit, that's my roommate. He hops up runs into the other room and they're in there for a while. And I'm laying across the bed. They come in. He goes, I hope you don't mind. I told my roommate you get a great head. And I turn around, I said, okay, let's do it.

The roommate, like, serious? So I give the roommate head. So while I'm doing it, the roommate's like talking shit. Like, you're a good, oh, you're a little slut. I'm like, oh, this is kind of odd. Oh, boy that I just blew. He's behind me. He's playing my ass.

And he puts a finger in. I'm like, okay, then another finger. Then he leaves and comes back with a condom. and I'm like, wait, I don't think I'm ready for this. And next thing I know, it's kind of a spitbrush thing. It was interesting because it hurt like hell at first. And once I got accustomed to the size and just the pounding thing, because he wasn't pounding at first because I kept saying take it easy.

Right. And once he got used to it, then I started asking him to get it. and both of them basically fuck me two times each at least. Wow. Roommates, quote unquote. Roommates, right. Yeah, so I thought about that afterwards. And my friend, she goes, what happened?

Because, you know, he's straight. I said, well, if he's straight, he showed and act like it today. She's like, okay, my straight parents don't even want to fuck you, huh? I was like, well, yeah, both of them did. And she was like, what? But at this point, what do you consider yourself? Bye. Okay.

Okay, cool. All right. I was just curious. Yeah. Okay. So she thought that, but so those two guys weren't like gay guys living together. This was a guy that was like straight, but yet, you know, he makes a move on you and him and his roommate are doing you together. So obviously, you know, there's a lot of guy and guy action going on in that household.

It wasn't their first rodeo. It definitely wasn't because he knew how to ride the bull. I got it. Do you like the, do you liked bottoming? I did. It was okay. It was like, I joke with my friends. I say, well, Hershey Highway only allows Toyota's and, but we were not taking 18 wheelers.

Nothing big. Nothing big. Okay. Okay. Okay. Seven and a half, eight is no limit. Okay. Oh, my God.

That's kind of big. Anyway, go on. Oh. So, yeah, well, the professor thing was funny because I was graduating college and needed one grade on the dean's list, but I could not pass this fucking class. And so when I asked a professor what I needed, I mean, everybody in the classroom was failing. And he said, well, look, I want, I need people to come to my office and we'll sit down and see what plan we can have to get you guys a pass. And he was the professor. We called him Mr. Howe Professor.

All the girls on campus loved him. So I'm sitting in the lobby waiting, and I'm like, okay, I got here before the other people, why am I waiting? So finally, he calls me in. And he goes, yeah, you're great. I said, what do I need to pass? He goes, you probably need Jesus. I said, oh, God, here we go. So he comes around the desk, and he's standing in front of me.

I noticed a noticeable lump. And I looked and I was like, okay. And he said, so what are you willing to do to pass? I said, well, whatever I need to do? And he said, really? I looked at him and I thought, okay, I took a chance. I said, this may be his way of telling me, well, here it is. Let's see if you make a move for it because if I make a move, I could get fired.

So I reached and held it and he just looked at me. Oh my God, this is another fucking grooming experience. Here you are having a teacher take advantage of you. I never thought that was a grooming. Well, I mean, you know, he's telling you I'll give you a good grade if you touch my cock. I don't know if it's grooming, but a lot of this shit is like, you know, fucked up a little bit. It's not consensual like, oh, you know, you know what I mean?

It's kind of like shit that happens, but it's very much a pattern in your life. Wow. See, I never thought about that. So I end up doing that and he enjoyed it, of course. And I stood up after he came. I swallowed and left. And got back to class for the final. And he walks by and he puts the paper on my thing and he said, no need.

was across the top of the paper. Oh, my God. Like no need for a grade you swallowed kind of thing? I guess so. Oh, my God. Yeah, so I graduated and walked across stage and everything. I wonder how many other people blew him for a good grade. I mean, maybe that's why he made everyone fail that class.

Like, maybe he made the test so difficult or lied about all your grades so you'd all wind up in the office. And, you know, he just sort of threw shit up against the wall and saw how many people would take that, you know, boner experience. That was like a fucking racket. He was running there, okay? Everyone was failing for a reason. It's not uncommon in college. Really? Oh, it's not.

I mean, there's a hell in high school there guys fucking there on students. Yeah, well, it's just all, it's fucked up if you ask me. Anyway, let's go. It is. What about your sugar daddy? You got some doms. You have a trans woman. Oh, God.

Sugar day. Oh, God. Yeah, it's right. Go on. Yeah, that's funny. I was working. Let me ask you, before we get to the show. Sugar Daddy, though, are you still continuing to dress? And is it only like when you go out?

Like, how far do you take the cross-dressing at this point in your life? So if I go to, if I go out of town, I'm with some home girls that know the whole thing. We will, well, I'll do it with them. Uh-huh. And, or if I do want to just catch, you know, if I want to get some play where I want to suck at the egg or get fucked, I might put on something little or, you know, something that gives that illusion and go to the right spot and know that I will get, somebody will try to holler. Yeah. And something will happen.

Yeah, I've had the guys on your show that holler at you. You know, they like the cissies. You know, they call them cissies, like the guys that are dressed up like chicks looking to submit to them. You know, they love those. Right. Yeah. There's a demand. Yeah.

And if I don't put on the makeup or anything like that, I'll just go out as myself. But I'll have on, I would never do that in my whole town. But I'll dress up, you know, put on some little baby shorts or something and go to a club or something. And you'll get hit on. Right. Yeah, for sure. There's a lot of guys that are into that. Like I said, I've had them on my show many times.

Okay, so you're Sugar Daddy. How does that come about? It was funny. I was working at a job. And it was a dude that worked in the building. And I was probably 23 at this point. and dude worked in the building and we talked all the time and he was like he always said oh man you make a cute girl and i was laughing to myself thinking if only he never so we got to be pretty cool he's a little older and we had some layoffs at our job and i was like

so we're talking about it and he goes well man i can i mean if you need some help or something let me know and I said, oh, you're going to be a shir-a-daddy. He said, that's what you want to call it. And I laughed. He said, okay, what do I have to be if you're going to be a shir-a-day? He goes, so what are you into? And I said, well, what would you like? He said, well, you look like a girl half the time.

He said, I love to see you on some little shorts. I'm like, oh, here we go with the shorts. But why would he say you look like a girl half the time? Did you dress like a girl at work? No, no. And that's the thing. So I think that it was more of a body thing. I played, I always had big thighs and a butt.

And for some reason, that was, that I got attention from the time I was 10 until, you know, my mid-30s, 40s. It was always attention. So, and it was, you did, I just looked at guys like purse when I was younger. But then, you know, we had to deal with the neighbor down the street. So it was like, okay. well, the legs and the butt is getting attention. Right. Okay.

So. You have like a girl's bubble butt or something like that? Yeah. Okay. I play, like I said, I play sports and I had the fat stomach and a small waist. And it was funny. So I even had girls saying, damn, if I was built like you, I'd be naked all the time. Right.

So this guy, though, says, just throws out to you that you look like a girl sometimes like that. Yeah. I kind of laughed at it. And he said, he's looking at me like, okay. And I'm thinking, oh, okay, he wants to take advantage of saturation. Let me see what he's talking about because I'm like, I don't want to move back home. So he goes, what if I pay your rent? I said, well, what have to do?

He said, be available when I want to come by. I said, why would you want to come by? I want to make him say it, right? He said, so what are you into? And I looked at him and I was like, so I'm straight. And he goes, okay. I said, but I will suck the connotation. He goes, would you suck mine?

I'm like, if you came to my apartment, yeah, I'll suck your dick. And he goes, okay. I said, well, you want anything more? He goes, no, he said, but when I come by, I want you like in something sexy. So we back to the dressing again. So every time he came by, I'd have on something little. And most of the time, he just wanted to hang out. Or, you know, me sit on his lap or something.

It was crazy. Right. Interesting. Yeah, that lasts at about a year. But he paid my card note and my apartment note. Oh, okay. So he paid your rent and your car payment. Exactly.

Just for sitting on his lap dressed as a girl. Well, no, there were lots of little jobs, but. Oh, you just said he didn't want anything. No, no, no. I said he wanted it sometimes. Oh, okay. I thought you said, well, maybe he said most of the time he didn't. I thought you said he never wanted anything.

No, no, a lot of the times. A lot of times. he didn't. He would come over and just want to talk and hang out. But there were other times where it was like, okay, let's do something kinky. Okay. And did you enjoy that? I'm really dead.

I actually, I think I threw him off because when I asked him, I said, why don't you bring some friends? He's like, what? I said, bring some friends. Sometimes I want to want a second or more than one guy. He's like, oh, shit, okay. But he never did.

Right, okay, so you never did that with him, but you blew him a lot, and that lasted how long a year? About a year and a half, because it was about a year and a half until I got another job. Right, okay, go on. Yeah, so I just told them, okay, that's it for that. And let's see, I've done... You have a trans girl, and you have some doms we haven't talked about. Oh, Lord, the trans girl. One night out, see this cute girl, I thought was a girl.

we're talking and she says I need a ride home because my people have kept me. I don't know where anybody is and I said, well, where do you live? She told me when she lived, I said, okay, I'll drive you. I'm just thinking she's a cute girl. We get in the car and we're driving

and she looks at me and we're just talking and she goes, wait, you don't know, do you? I said, no one. And she goes, oh shit. She said, I don't want any trouble. I'm like, what's the trouble is going to happen? And she said, I'm a boy. I'll start laughing. And I said, okay. And she goes, no, seriously. I said, oh, okay. And we said, I've got

something to eat, drove back to her apartment, and I go upstairs, and she goes in the room, and she comes out, and drops her robe, and she had it pulled back. And I'm looking, going, there's no way you're a boy. And she takes one step, and bing, it pops out. I was, of course, that wasn't my first radio. So I said, oh, okay. I'd zip my pants and I'm like, what do you want to do? And she just gets on her knees and start sucking me. So after I came, I told her, I said, stand up. And she stood up and I sucked her off and she was like thrown off because she said,

that hadn't happened to her. So that lasted. We did that several times. And after that, I was like, okay, dreams are fun. So I was out trying to find them. And what's really difficult is finding women that are into guys who are into everything. Right. I mean, listen, it sounds like you found a lot of accepting girls of, like, who you were.

The earliest girl really was. But I was wondering, like, during all this time when all this stuff is going down and everything, like, have you had any long-term relationships? Are you in a relationship now? I've had long-term relationships. Right now, I'm not really into one. Right. But when you had them to...

Were any of your girls besides that first one into the stuff that you're into? Not everything, but they were into certain things. Did they allow you to like hook up with guys and shit? Like did you have open relationships with them or not? Well, I like girls. I like bi girls. And a lot of bad girls aren't into that. But then I found one shit, you know, once I knew they were bi or something, I would tell

them, hey, I like to play. And some of them would be turned on and others will be. like, oh, that's the end. Right. Yeah. Or one even said, hey, as long as I don't know about it. Then after a while, she wanted to know about it and it turned her on. She wanted to be there

for all of them. Oh, okay. So that's good. What about the doms? What happened with the doms? You were dominated? Oh, God, yes. I was into a formal one light and ran into get gum.

I'm giving the Clifton version because I you time limited, but ran in to get gum and there was this gorgeous girl in there. And I kept looking going, God damn, but she's tall because I'm like 5-7, 5-8. And I just said, okay, let me get my shit together, get out of here and go to this formal. So I get in my car and I'm opening up the gum and this girl comes and knocks on the door. And she goes, you forgot something. Like what? She has me her number.

I'm like, oh, she said, call me and get home. home. Okay. I said, but it'll be late. So, of course, I called her when I got home because she was just stunning. And we're talking and she said, are you a freak? I said, what would make you ask that? And she said, I don't know I got a vibe. I said, okay. I said, yeah, I'm pretty freaky. She said, okay, we'll see. So she told me to come to her house. When at her house, she answers the door and she says, okay, when you walk in the this door, you're mine. And whatever the fuck I tell you to do, you do. I'm looking at her thinking, I don't think you can ask me to do anything I won't do because you're hot. Walked in and she told me, go in the room, put on what's in there. I go in the room, I said, oh, no, not again.

It was a blue jeans skirt and super short. And she said, no underwear. So I put it on and I come on. She said, good little bitch. I'm like, oh. So I go and she said, sit down. So I sit down and she hands me some loom. And she said, I want you to jack off a nut all over my skirt.

I said, okay. And she said, do you need some help? I said, well, what are you going to do? She pulls out this thing that has these balls on it. Like the balls getting larger. Okay. Like butt bees? And it's like, right.

It's something like that. It's like a stick with these things on it. she goes, so I'm going to put this in your ass. So really? She goes, mm-hmm. She said, you want that? I said, yeah. She said, tell me you want to stick it up your ass. I said, okay, I want you sticking up my ass. And she goes, oh, she puts it in my ass, and I'm stroking. And she says, suck on my titty while you're doing it. I'm having a time of my life. Right. So I came all over her skirt. She was so turned on. She just leaned over and stopped licking it off.

And she said, you're going to be my name. on a pitch. Okay, no problem. So that lasted until she moved. That was a girl for you. That was like your type of girl. Oh man. She was, yeah, she was something. She would invite other guys over and have them all dressed up and it was wild. Let me ask you this. How old are you now? Forty-six. 46. And you've just been having these kind of crazy experiences since the get-go, obviously. Do you have them up until now? And you said you don't cross dress anymore. Like when did you stop dressing up in those little outfits? The little outfits and stuff like that, that had probably my 30s when I started getting really into my profession.

And I knew going out and stuff was kind of risky. So if there's a party, I will do certain things as far as clothes are concerned. If it's a controlled environment, I actually blew a friend that has no idea I blew him. What do you mean? Because you were dressed up and with makeup and chin. You didn't know it was you? Yes. Had no idea. But how did you meet the friend? Did you catfish him? No, no, no. We had known each other since we were in like high school. Right.

So we played, we're on the same team. We played football together. So it was like we were friends, but we were super good friends. We were friends because we're on the same team. Hung out and stuff and all that. So one of the girls had a party for one hour. her friends, one of her, one of my friends had a party and the party was supposed to be for a bunch of guys that were by and you either had to wear like a thong or lingerie. So of course my friend told me to wear a lingerie. So get to the party and my friend walks through the door and I'm like panicking because like what the fuck is he doing here? Oh shit I don't need to be seen like this and

She goes, calm down. Easier, too. I was like, oh, that's true. So I'm standing at the bar talking to my friend, and she said, okay, he's looking at your boat from across the room. I said, oh, he's back out because he got into one of rooms. She said, yeah, he has on the phone. But I was like, okay, that's funny.

So he walks over, he's standing at the bar, and he's standing behind me and pressing up against me. And he said, hi, that's it. said hi, didn't turn around. And he started rubbing and I didn't stop him. And I'm like, this is so funny. My friend is standing there cracking up laughing. Yeah, that's crazy. So he grabs me a hand and we walk over to a couch and he sits on the couch and went to stick out. And I was like, okay, I got on my knees in front of him and did it. And it was funny because after we were finished, there were a couple of the guys standing there holding the next like okay I'm next it's like no it doesn't work that way

so to this day he still has no idea and it was funny because we had gone out with a bunch of other friends he was there so he told the story about this girl he met at a party that gave him head and I was like that was not a girl and you knew that wasn't a girl he told a whole bunch of people that story yeah but he said it was a girl that did it Right, right. But you know that he knew it wasn't. Oh, yeah, because it was clear that everyone in the party did is nothing but guys. And some of the guys look like linebackers and miniskirts. Right. Other guys, you know, were passable.

Yeah. Yeah, so, yeah, so it was like, yeah, you knew what you were doing. Oh, my God. What's in your future? Like, what are you looking for at this point? And you're like, just to continue on doing these freaky things, are you looking for a partner in crime? Like, do you ever want to get married? Oh, definitely.

people who are open-minded. And what's so funny is it's harder to find women who are into stuff than guys. Because guys are just out. Yeah, you could date a guy, though, if you're open to it. That would probably be your perfect match. But no, there's girls out there that are down for what you are. Look, you had them in the beginning. I've had people on my show that have met women that are into that.

So you just got to, you know, be honest about who you are pretty early on. So you could weed out the women that aren't. Yeah. But there's definitely someone out there. that would be into it. We're out there. I have a friend that's in Charlotte that's into it. So we've been talking.

So we don't know what we're going to do. Yeah, well, one of your friends was the one that told you to call in, right? Do you want to send in a picture? Do you want to send in a picture, dress? Do you have any pictures of you when you're, like, dressed up?

Not what your face. Everyone remains anonymous on, but do you want to send some picks like dressed? Yeah. What's funny is I do have, I made sure that no one ever took pictures because pictures are evidence. Yeah.

But recently I found out that one of my friends had snapped a picture. So you have one. And so, yeah, I will get that one. Yeah, get it to me. So I'll put it on my page on for people to see. I love your story. You're a very good talker and telling of the story. Like, I probably didn't have to say one fucking thing.

I might just edit out every single thing. I said, I don't know. But you got to all the stuff that you needed to get. There's a lot of stories there. You were made to be groomed. You were made to, you know, dress up like a girl. You were born for this. It's kind of crazy, the stories.

But thanks for calling in and being so honest and sharing them all with me. Yeah, it's, what's funny is I think I left some out that my friends were telling me. They said, oh, no, no, no, no, we're going to follow whatever. It's okay. You did enough on this episode. You know what I'm saying? Like, you didn't, you kind of like gave us the whole menu. You have a little bit of a lot of stuff, you know?

Some people just do one of the things you're talked about on this episode, and you've done it all. You know, typically I'm talking to one cross-dresser that sucked a dick, but you're a cross-dress that sucked a dick. You had three-sums. You know, you've done it all. So, anyway, thanks so much for calling in and sharing your story. And get me that picture sooner than later, so I have it. And I'll let you know when your episode's going to air. It'll be probably on a fetish Friday.

Oh, that's perfect. Okay. All right. All right. Awesome. Thank you, so what are we calling you? And I'll give you free access to my Patreon to see. for one month to see the comments.

And I'll also give you free access to my Discord. People are freaky over there, so you'll have fun over there, okay? Yay. You're going to meet your people over there. I'll give you free. My tribe. Yeah, yeah, awesome. Thanks, Christopher.

Thanks so much for calling in. No problem. You have a great weekend. You too. 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 one or two and then skip around. You could read the whole book. It's available in eback format, paperback format, and finally, the audio book 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. sent it to me at Strictly Anonymous Podcast at gmail.com. That's Strictly Anonymous Podcasts at Gmail.com. And I will send you the link to Discord. So anyway, thanks so much for tuning in. This is the Strictly Anonymous Podcast.

Okay. Okay, good news. I do have a book out. I wrote a book and it's coming out. The book is called Strictly Anonymous Confessions. Secret Sex Lives of Totally. little strangers. What I did was I picked out the 17 best episodes. That was very hard to do. Okay, I picked like one from each category. And I retold the story from the third person. So it's not

interview style. It's a little bit more erotica. The only place where I took creative liberty was in the sex scene. So it's even hotter than my episodes. Like I said, it's told in the third person. And they're all true, just like my show. I mean, these are real stories from my show, just written out, like I said, in the third person, not an interview style, more like a story, but a true story, a true super hot story. Now, listen, it is available for pre-order now, and it's not coming out until October 14th. And I was like, oh my God, that's a long time away. So I figured I'd incentivize people. If you want to pre-order it now, I will give you free access to my Discord if you pre-order it now. All you got to do is screenshot, a pick of the receipt,

just screenshot it to me. Send it to strictly anonymous podcast at gmail.com. And then I will send you the link to my Discord. So that's a little incentive to pick it up now. It's on Amazon, Barnes & Noble, Simon & Schuster. The link is in the description.

So make sure to click on it. And if you get it, send me the pick of you purchasing and I'll give you free access to my private discord. That is a totally naughty, super hot community with a lot of people over 2500 people over there, having fun. Remember email me the pick.

strictly anonymous podcast at gmail.com.