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Sex with Dr. Jess


September 7, 2023

3 Sex & Relationship Lessons From “Lifestyle” Couples

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Sex Toy Advent Calendar by Womanizer & Lovehoney 24-piece sex toy calendar for ongoing sexy couple's playSex Toy Advent Calendar by Womanizer & Lovehoney 24-piece sex toy calendar for ongoing sexy couple's playCouples in The Lifestyle (AKA Swingers) practice a form of ethical non-monogamy that usually involves sex play with other singles and/or couples.

In this quickie episode, Jess and Brandon discuss advice from three swinger couples who share their insights for happier relationships (and, by extension, hotter sex).

If you’re here for the Womanizer X Lovehoney Advent Calendar, CLICK HERE, and be sure – to use code DRJESS to save.

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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.

3 Sex & Relationship Lessons From “Lifestyle” Couples

Episode 333

[00:00:00] You’re listening to the sex with Dr. Jess podcast, sex and relationship advice. You can use tonight.

[00:00:15] Brandon Ware: Welcome to the sex with Dr. Jess podcast. Dr. Jess, how are you feeling today?

[00:00:19] Jess O’Reilly: I’m feeling all right. I’m feeling good. Talk to me. Why is that? We have just disembarked the Desire Cruise, and I don’t know if this was maybe number six for us in terms of Desire Cruising, but we just came off a week in Greece with one stop in Turkey.

[00:00:33] Jess O’Reilly: It was a lot of fun, but it was pretty intense.

[00:00:34] Brandon Ware: Yeah, it was intense.

[00:00:36] Jess O’Reilly: Lots of socializing.

[00:00:38] Brandon Ware: Yeah, that’s an understatement. I always like to party. Oh my gosh. I can’t keep up. I don’t know. I gotta, I gotta tell you, I don’t know how they do it. They’re up at like seven in the morning and they party hard until like three in the morning.

[00:00:49] Jess O’Reilly: Is that, is that their schedule? I don’t know. I’m asleep long before

[00:00:52] Brandon Ware: that. I’m, I’m, I’m impressed.

[00:00:55] Jess O’Reilly: But it’s super friendly crowd. Oh yeah. Like it’s so much fun while you’re on, but then, you know, when you come off of something that’s so highly social, at least me. Oh, I feel like a total drop. I just need to be quiet for a bit.

[00:01:07] Jess O’Reilly: Need some time to chill. Yes. Now we are also on route to Atlanta for Sex Town South via Toronto. Very excited for this. So this is definitely a quickie episode because we just don’t have a lot of time. We’re stopping in Toronto overnight. So that I can feed my dad and see my mom and my stepdad. Check on my plants.

[00:01:26] Jess O’Reilly: Yeah, drop off my cleats to my friend’s house because I’m gonna, I need her to carry them to a tournament for me in Montreal. But what for? What are you playing? We’re not talking about that right now. Okay, I play Ultimate and Brandon likes to make fun of it.

[00:01:39] Brandon Ware: Hope Adam’s listening right now. Adam Maurer.

[00:01:41] Jess O’Reilly: Oh my gosh.

[00:01:42] Brandon Ware: I feel like we’ve bonded over this.

[00:01:43] Jess O’Reilly: Brandon calls it Frisbee. If I call it Frisbee, people who play Ultimate are going to get mad at me, but it’s the least Ultimate. It’s Ultimate. Anyhow, we have a short amount of time, so we are going to get in to three lessons that I learned from lifestyle couples on the cruise.[00:02:00]

[00:02:00] Jess O’Reilly: Three lessons from swingers, basically. These couples are swingers now. Definitely not all the couples on the cruise are swingers or lifestylers. I want to say it’s about 50 50. Yeah, I would, I would say so. But everybody’s pretty open minded. There’s a lot of, you know, playfulness. A lot of flirtation. A lot of flirtation, but not, uh, I don’t know.

[00:02:18] Jess O’Reilly: It feels pretty low pressure to me.

[00:02:19] Brandon Ware: Yeah, I would agree. I mean, nobody’s overbearing. I mean, everyone’s there just to, honestly, just to party and have a good time.

[00:02:25] Jess O’Reilly: Yeah, it, yeah, it was really fun. Hey, before we go on, what was your highlight?

[00:02:28] Brandon Ware: Ooh, so much fun. I mean, I really enjoy the stops. I like to get off.

[00:02:34] Brandon Ware: We get off at the, at every port. So I enjoy, um, yeah. Okay. Yeah. I really enjoyed Mykonos. I thought the water was spectacular in Mykonos and very chill and relaxing day. Um, what else did I enjoy? I enjoyed, uh, Cavala. I enjoyed the meals. The food was, was incredible. So there’s so many highlight meals. And then, uh, you know, on board, uh, I really had a great time at the, the white party night.

[00:02:59] Brandon Ware: It was a fun night where everybody was partying hard out dancing. And the weather was fantastic. Like, oh my gosh, we got such a great week of weather on the boat. So smooth. Yeah, it was just fantastic.

[00:03:12] Jess O’Reilly: My highlight was definitely Mykonos because we just chilled for the day. We were kind of on the edge of a cliff overlooking the ocean.

[00:03:18] Jess O’Reilly: We’d walk down to the ocean, jump in, and it was so clear. And then I think the other was Kusadasi. We’d been to Kusadasi, Turkey in the past and visited Ephesus, which obviously is super fascinating to see such an ancient city and walk its, you know, roads with street lamps that you can’t, thousands of years ago, you think about them lighting up.

[00:03:36] Brandon Ware: Oh, incredible engineering from, you know, thousands of years ago was spectacular, but also in Kavala. I don’t know if I’m pronouncing that right. No, no, no. But I’m saying in Kavala, the other stop finding those local beaches was really cool.

[00:03:48] Jess O’Reilly: Yeah. I thought that was awesome. Yeah. We stumbled upon some beaches were, I mean, they were actually there.

[00:03:53] Jess O’Reilly: Some of them were beaches, but some of them were rock like cliffs where you could swim. And there was one where only two people were there. [00:04:00] They showed us how to safely get in and not step on sea urchins. Yeah, that was really cool. Another highlight. The dog cafe in Cusadasi. What was the name of it? The Hand Coffee Shop.

[00:04:09] Brandon Ware: The Hand Coffee Shop in Cusadasi.

[00:04:11] Jess O’Reilly: Yeah. We’ve been there before and there’s just dogs wandering around.

[00:04:14] Brandon Ware: Yeah. Three owners, three dogs with their three dogs. Always a great way to have a coffee.

[00:04:19] Jess O’Reilly: Yeah, that puts me in a good mood. Okay, so let’s talk about some of the messages, some of the important lessons and reminders that we got from folks who are in the lifestyle.

[00:04:29] Jess O’Reilly: And again, I get it. Not everybody’s in the lifestyle, but I think we definitely all have something to glean from hearing from people who have different. relationship arrangements than our own. Especially ethical non monogamy. And so, yeah, I’m just going to dive into it. So the first, and I posted about this on Instagram, get off the escalator.

[00:04:46] Jess O’Reilly: And I took a direct quote on each of these. So this is from a couple from England. They’re in their 40s, 43 and 46. I think she was the older one. So I think he was 43. She was 46 from England. This is what they said. What I mean is that one thing doesn’t have to lead to another. If you go to a party, it doesn’t mean you have to play.

[00:05:03] Jess O’Reilly: If you play one time, it doesn’t mean you have to do it again. You don’t always have to up the ante. And in fact, pulling back can be even more exciting and will sometimes be necessary for the relationship. I find people are often afraid to try something because they think their partner will just want more and more.

[00:05:19] Jess O’Reilly: But if you’re feeling that kind of pressure in your relationship, then I don’t think the lifestyle is for you.

[00:05:24] Brandon Ware: Yeah, I thought that was a really helpful piece of advice that they shared with the group. And. I think there’s this idea that every time you do something, you have to be able to up the ante, like you said, and do some, do it again or go bigger.

[00:05:34] Jess O’Reilly: Well, I hear people say that, like, if I do this for my partner, especially in cases where they’re like, Oh, I’m not really into this, but I could do it for my partner. I get that they’re into it and I’d love to be a part of it for them, but I often hear, well, my fear is that if I do this, then they’re going to want that.

[00:05:48] Jess O’Reilly: If I do that, then they’re going to want. Something even more and I love this idea in life that life isn’t an escalator It’s not just where we’re always ascending to something bigger or more dangerous or greater. We’re just [00:06:00] experiencing

[00:06:00] Brandon Ware: Yeah, I mean, I like you just said I think is applicable across the board and there’s always this idea that you’re progressing up But I also think that the couples that had these sort of conversations are the ones who seem a lot happier Like does it is it not the case where you know, they’re having these conversations when they’re not in the heat of the moment They’re They’re decompressing, they’re dissecting, they’re discussing these experiences after the fact.

[00:06:22] Brandon Ware: And it’s those discussions that I feel when these These incredible pieces of advice and insight come out. And that’s what I really found interesting and helpful.

[00:06:30] Jess O’Reilly: Well, that actually leads, and I know not on purpose because I never, I know you never read the notes, but that leads into another piece here, which is bring up the bad when things are good, so many people avoid having serious conversations because.

[00:06:44] Jess O’Reilly: When things are good, you don’t want to ruin it by bringing up something intense. Right. But then when you wait until you’re really upset to talk about that intense thing, you’re not going to be kind of at your best in terms of communicating or emotionally processing or slowing down and taking a beat.

[00:06:57] Jess O’Reilly: So this is what these newlyweds, so these, these folks are in their fifties. So she was 55, he was 59 and they’re from Germany and they just got married. This is what they said. Yeah. Don’t wait until you run into trouble. Instead, talk about the hypotheticals. We learned early on that it’s easier to deal with the hard stuff when you’re not already upset about those same issues.

[00:07:18] Jess O’Reilly: So bring up the difficult stuff, jealousy, insecurity, changing your mind. So they’re talking about swinging here when things are already going smoothly so that you’ll have a better idea of how your partner feels and what they need. If and when the issues actually arise and I love this the talking about, okay, so what if this were to happen?

[00:07:37] Jess O’Reilly: What if that were to happen? What if I freaked out because this does happen in life people pull back they get upset They change their mind. They freak out. It’s actually not the end of the world. And so this applies across the board We always talk about this if you’re going to talk about intense topics difficult topics contentious issues Bring it up when you’re in a good place, make the time for it.

[00:07:56] Jess O’Reilly: Maybe set a time limit on it. Like you don’t want it to get away from you, but [00:08:00] this is really what I do in my work, right? I’m bringing people conversations, conversation tools and starters so that they can actually talk about things before the issues arrive. Arise. It’s like fire prevention.

[00:08:11] Brandon Ware: And I, and I love Germans because they’re always pushing the boundaries.

[00:08:14] Jess O’Reilly: They are. Yeah.

[00:08:15] Brandon Ware: No, for real. I’m serious.

[00:08:16] Jess O’Reilly: These ones have the best outfits.

[00:08:17] Brandon Ware: If you , they have the best. Oh, I do.

[00:08:19] Jess O’Reilly: And this actually leads really nicely into the third piece of advice, which has to do with mistakes. This is to me, One of the most important pieces in relationships when it comes to sex, when it comes to pushing your comfort zone, when it comes to trying new things, not just non monogamy, but just overall embrace mistakes.

[00:08:38] Jess O’Reilly: So this is a younger couple from the States, 38 and 46. They have three kids and they said, if something goes awry, it’s okay. Everyone is always asking, what if? So what if something goes wrong? What if an experience goes sideways? That’s life, whether you’re monogamous or not, don’t let the fear alone hold you back.

[00:08:59] Jess O’Reilly: And they say, imagine we did this with having kids, with moving cities, with taking a new job. There is too much focus on making things perfect and it’s not realistic for vanilla couples. So why do we put pressure on ourselves in the lifestyle? If you have the foundation of loving, happy relationships, you probably feel even closer when you go through the so called mistakes together.

[00:09:18] Jess O’Reilly: And this is something I hear so much. from couples that they’re afraid that if they push their boundary, if they go to a sex club, if they try a new act, if they engage in something that makes them nervous, that it could go wrong. And I’m like, okay, so it might go wrong, but what does that mean? What does it mean?

[00:09:35] Jess O’Reilly: Does it mean that you hate yourself, that you hate your partner, that your relationship falls apart? No. Hopefully you’re not even having these conversations unless you already have the foundation of trust and love and understanding and a willingness to work through things. So, you know, in life things go wrong, right?

[00:09:51] Jess O’Reilly: We know we make mistakes. We know that we’re like, Oh my God, I can’t believe I said that. I can’t believe I did that. I can’t believe I responded that way. But with sex, we treat it like it’s so [00:10:00] special. Like we need to like put up the bowling alley bumpers to make sure everything goes perfectly. When the worst case scenario is not nearly as bad as you’re probably making it out to be in your mind.

[00:10:10] Brandon Ware: You know, we watched a show the other day and I really liked it. We watched Tet Lasso and one of the last episodes they said something. They said, perfection sucks. Perfection is boring and

[00:10:20] Jess O’Reilly: beard,

[00:10:21] Brandon Ware: beard,

[00:10:22] Jess O’Reilly: beard said it,

[00:10:23] Brandon Ware: but it was just the idea that it’s okay to screw up. It’s okay to, to, for things to go wrong.

[00:10:30] Brandon Ware: And, and I really, it resonated with me and I never thought about it from the perspective of perfection sucks. The idea of trying to be perfect all the time is exhausting. And like, I know how draining it can be. So why am I so afraid to mess up? And it’s going to happen, man. And just embrace it and move forward.

[00:10:48] Jess O’Reilly: Yeah. And I get, obviously, I mean, the flip side of that is in relationships, we have the inclination to protect what we have, right? So if we’ve got this good relationship, we’re afraid that if we go and try something or do something differently or engage, for example, in non monog, ethical non monogamy, that it’s going to ruin the relationship.

[00:11:04] Jess O’Reilly: But I would challenge you to think about why do you think that this one specific act is going to ruin things? Like, why do we think that it’s that thing? But I get it. And it actually, all of these points, even though they’re from three different couples, Tie together. It has to do with, for example, the perception of an escalator, right?

[00:11:19] Jess O’Reilly: That, Oh, if we do this, that’s eventually going to get boring. And we’re going to have to up the ante that we don’t want to have these difficult conversations when things are going well, but I think the, this last one is the most important to me around embracing mistakes, like being okay with the fact that things don’t have to go perfectly.

[00:11:35] Jess O’Reilly: You can have bad sex. You can have a bad experience. You can have a fight, right? Like we see this all the time where couples engage in experiences monogamous or not. That don’t work out and they still come out the other side, either exactly as they were or even better.

[00:11:49] Brandon Ware: Well, I think about the idea of screwing up and I guess I’m also thinking about things from the perspective of a relationship where you have that solid foundation to begin with so that when you do screw up, you know, that it wasn’t intended to hurt the other [00:12:00] person.

[00:12:00] Brandon Ware: You know, that it was. Um, you know, you can kind of, I don’t want to say laugh it off, but you can move forward and understand, okay, that didn’t work. Let let’s try it again, or let’s try something different, or let’s try a different, you know, approach on this, or maybe we don’t try it again. That was something we did and we didn’t enjoy it.

[00:12:15] Jess O’Reilly: Right. There’s always kind of pulling back, taking a left hand turn, taking a right, doing a U turn, whatever it is that works for you. So when I look at actually these, these perspectives or these insights, I think it’s. They really kind of line up for me as reasons why people won’t try new things. So maybe it’s more like hurdles, these notions or these, I don’t want to say limiting beliefs, these, these, um, thoughts that hold us back from trying something new.

[00:12:39] Brandon Ware: Yeah, no, I agree. I agree. All great, great insight though. And these were just a few of the many that I heard kind of come across your plate, you know, during these conversations that, that you were having.

[00:12:49] Jess O’Reilly: Yeah, absolutely. And I want to say also that you don’t have to do everything right. I think that these insights don’t apply.

[00:12:56] Jess O’Reilly: If you don’t have that foundation to which we referred if you have a partner who’s pressuring you, right? So I would never want a partner who wants something and the other partner doesn’t to take it and say oh no No, they said this like it says it doesn’t matter Well, listen, if someone’s not into something like they genuinely are not into it.

[00:13:11] Jess O’Reilly: It doesn’t align with their values It doesn’t align with their identity. They just simply feel so uncomfortable that it would be More distressful than pleasurable. However you define that. That means that maybe that thing just isn’t for you and you don’t have to do everything.

[00:13:24] Brandon Ware: Well, also, and you talked about that a little bit, just the idea of talking about something before you’re in that situation, it’s like, do I want to do that?

[00:13:32] Brandon Ware: Well, why don’t we have a conversation about it before we do it? And I can tell you how I’m feeling, what I’m thinking, what I’m afraid of, what I’m excited for, and then from there, maybe I want to proceed with it. And you know what, maybe I don’t, and I’m just really happy that we had this conversation. And now you know exactly how I feel.

[00:13:48] Brandon Ware: And, and, and, and again, it just, it strengthens the foundation.

[00:13:51] Jess O’Reilly: And don’t you want a partner who, if you decide to pull back or you say, you know what, I’m not feeling cool with this. It’s like, yeah, absolutely. Like I want, I want to support you. I want to take care [00:14:00] of you. I’m not going to make you feel guilty.

[00:14:01] Jess O’Reilly: I’m not going to put pressure on you. And so it really boils down to having that foundation of a happy, healthy. the loving, caring relationship where you want the best for one another. Because if you don’t have those things to begin with, there’s like no tool, no tip. These three insights may not even apply.

[00:14:15] Jess O’Reilly: Couldn’t agree more. Okay. We gotta go. We are off to Sex Town South, which is the coolest sex conference. So much fun in Atlanta. If you’ve never been look at it for next year, cause you’re probably too late for this year.

[00:14:28] Brandon Ware: Oh, that’s is it? Yes. It’s next year, but I’m sorry, but they’re also doing sex down south in Jamaica as well.

[00:14:33] Jess O’Reilly: Aren’t they? Hedonism in June. I have to get a promo code for that. Cause it’s just very preliminary, but it’s really growing. Yeah, I think it’s June 1st to June 6th or 7th down in Henanism with Sex Down South. The coolest, most fun group of people. For me personally, just my people. Really looking forward to it.

[00:14:49] Jess O’Reilly: And uh, I know that this has been a short one, but the good news is at Sex Down South there are so many brilliant minds, so we’re lining up a bunch of podcast interviews with some really, really brilliant folks. And uh, you’re, I’m gonna love the content. So you don’t have to just listen to our voices. I miss, I miss those interviews.

[00:15:05] Jess O’Reilly: So we’re going to let you go. But before you go, we have a promo from womanizer. com. So womanizer, you know, their technology, Pleasure Air, their sex toy advent calendar by Womanizer and Love Honey. is super discounted. It says 481 euros, but it’s on sale for 180 euros. And I don’t know what it is in us, but I know that the euro and the us aren’t too far off.

[00:15:27] Jess O’Reilly: Sorry for the Canadians because our dollar sucks, but it’s a ton, a ton of value. And it always sells out because last year, I guess the influencers put it on tick talk and it was within a matter of hours, it was sold out even though it’s for the holidays. So it includes. So many products. Okay. So the womanizer classic to clit stimulator, a mini massage wand, penis ring, a body massager, another penis ring, a textured stroker, anal beads, ankle restraints, wrist restraints, sandalwood scented candle, a card game dice, mini paddle mint, mint, orgasm bomb, vanilla massage oil.

[00:15:59] Jess O’Reilly: And much more, [00:16:00] I can’t read it all. There’s a crystal butt plug as well. And there’s a G spot massager and a G spot dildo. There’s a whole bunch of stuff. If you go to womanizer. com, it’s in the sales section. And I have a code, right? Uh, Dr. Jess. Just Dr. Jess. D R J E S S will get you a few extra dollars off.

[00:16:15] Jess O’Reilly: Womanizer. com, as I said, it usually sells out. And I guess it’s really early. It’s not quite the holidays and they’re already launching the advent calendar because hopefully they ordered more, but go check it out.

[00:16:25] Brandon Ware: I was just gonna say, that was the one that that sold out completely last

[00:16:28] Brandon Ware: year.

[00:16:28] Jess O’Reilly: Yeah, it was gone. Yeah, because they ticky talkers. Amazing. . Bye folks.

[00:16:35] Jess O’Reilly: You’re listening to The Sex with Dr. Jess podcast. Improve your sex life, improve your life.