Former PlayboyTV Exec Tells All: Group Sex, Sex-On-Camera & Overcoming Body Image Issues

This week, Jess speaks to her friend and former head of programming for Playboy TV, Wendy Miller. Listen to the pair reminisce about their days on set with Playboy TV, and many other shenanigans! This is one of Jess’ favourite interviews to date and not just because of all the talk of wine, gin and tonics, biting and strap-ons. Be sure to listen all the way to the end, as Wendy shares her story about overcoming body image issues as a ‘normal’ woman working in a world of Playboy bunnies.

This podcast is brought to you by Desire Resorts. 

Rough Transcript:

This is a computer-generated rough transcript, so please excuse any typos. This podcast is an informational conversation and is not a substitute for medical, health or other professional advice, diagnosis or treatment. Always seek the services of an appropriate professional should you have individual questions or concerns.

Former PlayboyTV Exec Tells All: Group Sex, Sex-On-Camera & Overcoming Body Image Issues

Participant #1:
So one of the weirdest moments, I think the most awkward moment on set for me was it involved this big, huge, huge dildo, and Ashley was trying to get it inside. I'd have heard. Do you remember that or were you there for that? I saw that. And I can never unsee it. Yes. Yeah. It's called the Great American Challenge. The Great American Challenge. That's it the Great American Challenge, which I think probably has to do with, like, hot dogs.

Participant #1:
I guess so. But a baby is something different, right? Yes. A baby comes out. Yeah, it doesn't go in. So I don't know if that's a Googleable scene or not, but that one was a really tough one for me. But one thing that I found was hard. And I don't know if you found this. I just found there was so much sex, and I was away from my husband for at least a month filming the show. And so I was kind of just bitter about it. I was like, yeah, you all like, sex. You have so much sex screw off by, like, week three. I was miserable. I don't know if you remember that. No, I thought that was just your general demeanor. Yeah. Well, I was going to ask you because I'm sure the people are wondering, other than trying to decipher my Chinese, Jamaican Canadian accent, what was the weirdest or toughest part about working with me? First of all, you are the most self facing person ever. This is a joke because you're the sweetest loveliest person ever. And this is ridiculous. No, there's nothing hard with working up with you. I thought you were going to come up with something like the gin drinking. I do know what it is. You are really, really cheap. And I think that you are overwhelmed with how cheap alcohol is in the US. And probably figuring out how to smuggle booze back into Canadia is how you're probably scheming the whole time. You're like Wendy. Look, I could get this bottle of wine for only $7. So I'm thinking, okay, fine. The bottle into your room would like, fill up with alcohol, and then it would slowly be gone. And you hadn't left, which I didn't understand. And then more alcohol would show up. And I'm thinking, we have to have some sort of intervention at some point. I don't know. Well, you don't know. We actually called my dressing room the Billiards Hall, so I would invite people secretly in. Now that we're done, I would invite people secretly in for a little bit of relief. But again, I'm like an Osmond at an orgy. So, I mean, literally any amount of alcohol, more than one drink a year is a lot to me. So by me saying there's a lot of alcohol in there, it's really a relative thing. Definitely wine, definitely. We're talking about how cheap the alcohol was in the US, that's for sure. Yeah. So as a comedian. When you go to the States and see the cost of wine, it's a very exciting thing. By six bottles, you get like 10% off. And that's a very exciting thing to a Canadian. I would say that's your biggest character flaw is your excitement about the cheapness of wine. Wendy obviously doesn't know me that well. There's way worse things now. Okay, Wendy, I follow you on Facebook, and anybody who follows you on Facebook likes to enjoy for the seven and a half years your post shows you are pitched. So I've got to hear about some of the ridiculous shows. Television shows. People pitched you. That was absolutely my favorite part of the job because for some reason, I don't know. Yes. Alright. Let me restart. I got the most ridiculously stupid pitches on a daily basis, and it was a massive waste of time. And it was also my favorite part of the day. I'm going to give you just a couple of them. And it's all going into the book because it is unbelievable how stupid some of these things were. For instance, some of them were kind of offensive, like a lot of them women were just treated as some sort of object. A lot of guys would come in and they would pitch a show like a game show where a girl was a prize, as if a woman was just sort of not an actual person, but an object that one would win. Or husband and wife have to play a game. And if they don't score enough points, the wife has to have sex with a strange guy. Oh, my God. This is a show that was pitched to me. One guy pitched me a show. He comes in a young guy who did mainstream shows. And he goes, hey, you know, the show 21 blackjack. And I go, yeah, sure. He goes, okay, here's the show. You play blackjack. But instead of using cards, you use girls. Oh, my God. And the hot girls are like the eights and the nines and the ten s in the deck. And ugly girls are like twos and the threes and the fours. Oh, my God. And now we're asking this question. One show, a guy pitched me a show called and I'm obsessed with vintage television. And this guy pitched me a show. He goes, the show is called The Dick and Dyke Show. The Dick Van Dyke Show. He goes, no, the Dick and Dyke Show, the straight guy and a lesbian live together and hilarity, ensues. What that's? My Tuesday afternoon. How is that hilarious? I mean, I have books. Do you want to hear the most offensive one ever? No, but yeah, I do. It. Okay.

This one came from someone who just got hired to work with me in the promo Department. Pitched me the show. He was there for about a week, and he goes, I got a show to pitch you. I'm thinking, oh, God. Here we go, he goes, okay. So, you know, MMA fighting, right? And I said, yeah, sure. I watch it. He goes, okay. So there's a cage match, MMA fight, and the two guys fight, and the guy who wins the fight gets to fuck the ring girl. And I go, okay. And the guy who loses has to fuck a fat chick. And that's not easy. And that's not easy. Oh, my gosh. I'm looking at him. Yeah. Did you fire him? I wanted to. I wanted to fire him right there on the spot. This guy is an overweight, unattractive guy who's pitching me this show and looking at me as if this is, like, the best idea ever. He's so incredibly offensive. Oh, my God. What's that? Because he's still a man, right? So it's okay for him to be overweight, but we have to make fat women into objects that are not supposed to be that's absolutely right. That's absolutely right. That's absolutely right. A lot of this is based on that. A lot of this is based on that standard where grotesque guy, fat guys, whatever guys of any sort of shape and size and body maintenance as it were, and more attitudes and terrible attitudes. Yeah. Can come in and pitch shows where women are just judged based on these ridiculous criteria. And yet it does not apply to any of them. And I would have to sit there. And I'm a woman of a certain age. I don't look like a Playboy Bunny, and I have to sit there and have to listen to this stuff. And it's a little soul crushing. And sometimes I would walk out of these rooms and I would be like, pretty offended and pretty angry. And it was really difficult. And there were times when people would pitch me a show, and I would just want to unload on them because they would have no idea. They would think that this is what I wanted to hear. I think sometimes people would come in there with the most outrageous and offensive idea, thinking that's what I wanted. And when someone smart would say, what do you want? I would say, I want to be surprised. I want something that you don't think I want. Don't come in here and pitch me something stupid. Where game show hot girl, like, 100 times. I got pitched a naked cooking show, a show set at strip clubs. I got pitched 500 shows set at strip clubs. Vegan, Strip Club, VA strip Club, black Strip club. I got pitched a show about a stripper competition. I said, I don't want to show about strippers. The guy said, it's not about strippers. It's about stripper poles. I mean, it's like one thing after another. And when someone came in with something that was at least had nothing to do with anything, I would respect them because it was at least a different idea. If you had more time, was there a show you wish you could have produced that you didn't really get to.

Participant #1:
Not really. I think I got to do pretty much everything I wanted to do. There were some shows that I would have liked to do if we had more money. But I got pitched a lot of versions of a show where a girl has sex with three guys and then decides which one she wants to date. And I thought it was a really offensive idea because I thought that once you have this girl who has sex with three guys, I just thought that first of all, that's what everyone wants to build up to. And so it's sort of like, where do you go from there? I was pitched that show maybe 15 times, and everybody thinks that they're the first person to pitch that show. And I thought it was just so obvious, and I wish that I was pitched smarter stuff that would have been nicer, mostly pitch stupid. You were working on a show where you went down to Desire Resorts, correct. And you did a. Yeah. So tell me about that Scout. So I was going to do a spin off of Swing, and we were working with the folks at Desire, and actually, I had spoken with you, and you're such a great brand ambassador for Desire. And I wanted to do something where we were doing something where we had one swing couple, and then we had a newbie couple because oftentimes when people went on swing, they had a couple that they were really hoping would be in the house. You mean Nicki? Yeah. It was always Nicki and Daniel. I'm kidding. I know. Which is why they host Toy Ride for us now because it was like they were, like the penultimate. But I wanted to host a show where people had the ultimate fantasy vacation, and they thought that they were just going away. And then they got there. And their favorite couple from Swing is there to meet them. And it would have been a surprise, and they didn't know about it. That's what we were going to do. Well, you didn't know that I was just going to show up and surprise you, too.

Participant #1:
Yeah. I figured you'd be there. Just knock, knock, knock. Jessica O'Reilly sitting by the pool while we're filming what happens? Makeup are done. So I had to go down to Desire to Scout the location. Now, first of all, Jess, are there any single people that go down to Desire? No, it's for couples, unless you're in their sexy young and wild month, and then you can bring a third party, right? You can bring a unicorn. So I had to go down to Desire as a producer to Scout the location. I'm not the type of person who goes to Nudist Resorts or the Swinger resorts by myself or even with my husband, for that matter. I'll fully disclose that. And so I had to go down to Desire by myself for work. And everyone at work is like, oh, going to a swinger resort. Nice. And I'm kind of saying, oh, I'm going for work. Shut up. So I've got to go down there and I get down there. And for the first few days, I mean, I'm wearing clothes, and I look like an idiot because I basically look like a Narc. And the folks down at Desire could not be lovelier. I'm not on the payroll. And I'm telling you right now, that place is spectacularly beautiful. And the people there are so nice. And my room was amazing. And the food was incredible. And everyone was just more lovely than the next. And I got there and everyone is sort of looking at me like, Why are you wearing clothes? And I'm trying to sort of keep a low profile because I'm just sort of trying to scope the place out without being noticed. Can they stop you there? That's not how you keep a low profile at Desire. You don't walk around wearing clothes. Well, that's what I'm trying to get at it's. Like, if 150 people are naked and I'm walking around wearing a black T shirt, black shorts and black loafers, you're going to stick out. And also, I don't have a gentleman with me. So I'm alone. The first night I'm there. They have theme parties every night. The first night I'm there. The theme party is Playboy Party. Oh, my God. So everyone's wearing Playboy stuff. And I'm just, like, dying. I start to talk to a couple of people. It turns out 20 people are there because of the show Swing. So now people find out that I created Swing, and that's my project. And I start to become like, this little famous person. And all of a sudden, people are like, hanging out around me because they know that I'm the person who runs Swing. I'm the boss of that show and the creator. So now I'm kind of popular. And people are like, Why are you wearing clothes? So now I'm kind of at a crossroads where I'm like, I should probably be naked. So people will leave me alone. Literally. That was my conundrum. If I got naked, people would not notice me, which is hard to wrap your head around when you're someone like me who does not walk around naked on the regular. But I had to do it. And that was scary because I don't normally do that. I've never been to a noodles resort. I'd never done anything like that. And so one day I was like, and so I decided I'm just going to do this. I'm just going to be naked at this place because it's the only way not to be noticed. And so Lo and behold. Day, I guess it was three. I walked out of my room 100% naked and went down by the pool and started talking to people and getting the lay of the land and finding things out and just kind of hanging out 100% naked, and it completely changed everything. It was a really amazing experience. It was amazing. Yeah, being naked around other people is a life changer. It is. And if you have body images, body issues, which I certainly do, they go away.

Because first of all, as a person who work at Playboy, I would spend all day with people who are professionally perfect. I'm not. I'm a regular person. I've had a kid, I'm over 50, like, I'm not professionally perfect. I'm regular. And so it would be difficult sometimes for me to hang out with these people because they're all so spectacular. And I'm not. And I started to get a sort of a stilted concept of what beauty was and what normalcy was. And hanging out with all of these amazing people made me think that I was incredibly busted up and going down to Desire resort. Yeah, there's a ton of amazingly beautiful people there, but there's also a ton of just real people there, which I normally don't get to spend a lot of time with. And suddenly I realized, okay, I'm fine. I'm normal, like everyone else, like, two levels of beauty, right? Like magazine beauty, which is cultural and then just natural human beauty and what we would be attracted to if we weren't told we should be attracted to what we see on the magazines. Well, I found desire to be an incredibly healing experience, which is not at all what I expected. And you kept telling me for years, you kept saying, Go to desire, and I'd be like, Shut up. I don't want to be naked next to Jessica O'Reilly. Look at you. You're like a Barbie doll, and you're like everyone else that I hang out with all day at Playboy. And so I couldn't fathom that. But when I got down there, I met all sorts of people who were just naked and letting it all hang out and sexy and fun and normal and just groovy. And it completely changed everything. For me, it was absolutely an amazing experience, so amazing that you took a naked selfie and sent it to me. It only shows your bare knees. No, look at that picture again. Jess is more than just my name. Okay, I got to go. I don't have my phone right in front of me, but that's going to be my first stop. You had talked about enjoying desire, but we never really had a conversation where you explained why it was so freeing and how it was good for body image. So I'm really glad you shared that. I hadn't anticipated that. That's really cool. I would love to go back there with my husband someday. I would love to go back there and just to hang out with those folks. And honestly, I thought it would be like the set of swing. I thought it'd be like sex everywhere. I thought it was like 90% nudists 10% swingers. It's not banging all over at all. No, that's what I thought it would be. But it's not at all. I'd say it's like 50 50. So it's like 50 people who have some sort of an open relationship, and then the other 50% are just really open minded. And if you want to get in the thick of the sex, like, up at the juice or in the playroom, you can. And if you don't want to, you just don't go to those places. I went up to the Jacuzzi, and I really didn't see that much. And I did not go into the I didn't go into the playroom because why would I go in there? That would have been perverted. But I didn't see much of the Jacuzzi at all. I saw a little bit of contact, but it wasn't like being in the red room. No. Well, to be fair, Wendy, nothing's like being in the red room. Okay. I guess my concept of group sex is probably a little stilted because I produce it. Yeah, exactly. Actually, sometimes at the Jacuzzi, there'll be a lot of action. It just depends on, like, usually later at night. Okay. Or right. I was looking for it. I thought it would be kind of fun, but I didn't see any. Okay, well, then you have to go back. Yeah, definitely go back. All right, Wendy, it's been so good talking to you. I know we could talk and talk and talk, but this has been our longest episode to date, so I want to say thank you. What's next for you? Are you writing the book? I'm writing a memoir about the seven and a half years I spent at Playboy TV. Yes, I hope I can be in it. You are in it. Jessica, will you call me Lord Jess? Can that be my suit in them? Because I don't want you to reveal anything about me, but just Lord Jess. Lord Jess, I think we need something better than that. I think. How about Wino McGee? Nobody will know it's me. How about biting McBites a lot? How about sex? How about the sex bomb? Sex bomb? A. So where can people find you, Wendy? So they can follow along? Because Wendy's hilarious. I don't know how much you do on Twitter, but on Facebook, you're hilarious. Well, thank you. I haven't been posting anything on Facebook lately because I'm not a Playboy anymore, so I have nothing interesting to post. No contract once my book is much more up and interesting, people can find me at the Wendymiller. Com. That's my website. There are many Wendy Miller, but I am the Wendymiller. Com and my Twitter handle is Wendy Miller show, and you're not going to find any updates for a while, though, because I'm very busy writing my memoir. But what does that mean? That's where I'm going to be pushing stuff out soon. If I send you nudes, you can share them out. Okay. They won't be of me, though. They'll mostly be animals. Animals wearing pants, which is basically like humans being nude.

Participant #1:
Exactly. All right, Wendy, thank you so, so much. It's been my pleasure. Thank you, Jess, and thank you again to Desire Resorts for your support of the sex with Dr. Jess podcast. You rock. I know my listeners and followers will be checking you out at Desire Resorts on all social media. And I did not ask Wendy and Desire did not pay Wendy to tell her story about Desire Resorts, but I guess she just couldn't resist. Thanks for tuning in, friends. Please follow me on Twitter, Insta and Facebook sex with Dr. Jess and leave your comments and questions wherever it's most convenient for you. My team will make sure they get directly to me, and I will do my best to get back to you. Have a very sexy week.

Participant #1:
Bye.