How To Plan A Successful Threesome

In Part II of our threesome discussion, we share questions and prompts to consider before you have a threesome — for individuals and couples. We also share some of our listeners’ insights on threesomes and discuss couples’ privilege.

Check out the questionnaires below, and be sure to check out AdamAndEve.com and use code DRJESS50 to save 50% off almost any item with FREE shipping.

Threesomes: Self-Questionnaire

• Why do you want to have a threesome?
• Where did the idea of a threesome come from?
• How do you feel about this source?
• What benefits do you expect to derive from a threesome?
• What are the perceived risks/costs?
• With whom would you like to have a threesome?
• Do you know if they’re open to it?
• How might your relationship with your threesome mates change post-threesome?
• What excites you most about a threesome?
• What motivates you?
• What concerns you about a threesome?
• Do you have any hesitations?
• What emotional elements of a threesome have you considered?
• How will you manage potentially challenging emotions should they arise?
• Do you feel comfortable communicating your desires and boundaries?
• What conditions increase your comfort level with open communication?
• What does your ideal threesome entail?

Consider the setting, relationships, involved parties, sex acts, etc…

Threesomes: Managing Jealousy, Insecurity & Distress

• Am I comfortable admitting to feelings of jealousy, insecurity and distress?
• I tend to feel jealous/insecure/distressed when…
• When I feel jealous/insecure/distressed, it shows up in my body as…(emotional presence)
• When I feel jealous/insecure/distressed, I want to…
• When I feel jealous/insecure/distressed, I can self-soothe by…
• When I feel jealous/insecure/distressed, I’d like you to…
• When I feel jealous/insecure/distressed, I don’t want you to…
• You’ll know when I feel jealous/insecure/distressed when I…

Some other cues to look for include…

Threesomes: Couples’ Questionnaire

• Whose idea was it? Do you feel any pressure?
• Have you (in)directly pressured your partner?
• Why do you/we want to have a threesome?
• What do you/we hope to get out of the experience?
• What are my/our concerns about the experience?
• Have we talked about jealousy, insecurity and other potentially challenging emotions we might encounter?
• What would it look like if it goes well?
• What might it look like if something goes awry?
• How will we communicate and respond?
• What do we value in a third party?
• What type of person do we want to connect with?
• Do we want to involve a stranger, an acquaintance, a friend and/or a sex worker?
• Have we considered our couples’ privilege and how we can ensure that all voices are heard and respected?

And if you have podcast questions, please submit them here. You can find the podcast on Apple Podcasts, Spotify, Podbean, Google Podcasts, Amazon Music & Stitcher!

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.

Episode 337

How To Plan A Successful Threesome

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[00:00:00] Brandon Ware: Welcome to the sex with Dr. Jess podcast. And I’m looking at Dr. Jess with a giant smile on her face.

[00:00:05] Jess O’Reilly: You like that? It’s a Terry Crews smile.

[00:00:06] Brandon Ware: I do like that smile.

[00:00:08] Jess O’Reilly: Okay.

[00:00:08] Brandon Ware: Why are you so happy?

[00:00:09] Jess O’Reilly: Because you walk past my laptop just now and I shut it. So you wouldn’t see what was on it.

[00:00:14] Brandon Ware: I, nothing shocks me.

[00:00:15] Brandon Ware: Nothing surprises me.

[00:00:16] Jess O’Reilly: It’s not porn.

[00:00:17] Brandon Ware: Does it?

[00:00:18] Jess O’Reilly: It’s not. I mean, obviously not.

[00:00:20] Brandon Ware: If it was, I’d been so shocked.

[00:00:21] Jess O’Reilly: It’s for research purposes.

[00:00:23] Brandon Ware: Yeah, me too. Research.

[00:00:24] Jess O’Reilly: No, it was an article that I didn’t want to go to about the Scandinavian sleep method.

[00:00:30] Brandon Ware: Okay. I’m a Scandinavian. I’m going to just assume minimalism, hard woods.

[00:00:36] Jess O’Reilly: You just sleep on flanks of wood.

[00:00:38] Brandon Ware: Yeah.

[00:00:39] Jess O’Reilly: No. So, so it’s this trend that has been popularized as of late on the TikTok. On the TikTok. Where you sleep in a double bed or a queen bed or a king bed. Okay. A matrimonial bed, as it’s called, and you sleep with separate comforters. So you share a bed, but separate comforters.

[00:00:57] Jess O’Reilly: And it’s my greatest fear that you’re gonna see this and want to do this.

[00:01:01] Brandon Ware: It’s, it doesn’t bother me at all because

[00:01:04] Brandon Ware: I don’t, I’m a human heating machine.

[00:01:06] Brandon Ware: Don’t you know this? After 23 years, I I, I have, I’m just, I’m a heating machine.

[00:01:11] Jess O’Reilly: I know, but does coming close to me get you too hot?

[00:01:14] Brandon Ware: Yes, absolutely. Don’t you notice that you’re like spoon me and then I’ll come over, I’ll spoon you, and then 30 seconds later, I’m like, okay, I’m sweating now I have to leave.

[00:01:21] Brandon Ware: And don’t you ever notice I temperature regulate with my leg, the single leg, and it’s like getting too hot. Leg goes out, give me five minutes, body cools down. Is

[00:01:32] Jess O’Reilly: it one leg or is it either leg? Depending on which side you’re on.

[00:01:34] Brandon Ware: It doesn’t matter. I don’t, most of the time, I don’t even know if I need a comforter, a sheet.

[00:01:39] Brandon Ware: Don’t you get, don’t, aren’t you like, why aren’t you sleeping with a sheet between your body and the comforter? And it’s because I don’t care.

[00:01:46] Jess O’Reilly: What drives me nuts is when you pull that one leg out and you put it on the comforter and then I can’t rip the comforter. Comforter away from you. That’s what I’m talking about.

[00:01:53] Jess O’Reilly: This is why I’m thinking you would like the Scandinavian sleep method because you could take the comforter off and I wouldn’t kind of moan about it, [00:02:00] but, and I don’t want two comforters. I know you’re going to tell me, Oh, you could have my comforter. No, I want you. I want your body. I want your heat. I want your warmth.

[00:02:07] Jess O’Reilly: I want your safety. Anything could get me in the night. If I’m not touching you, I’m scared.

[00:02:11] Brandon Ware: Have we talked about the murder side of the bed? Have we talked about this?

[00:02:14] Jess O’Reilly: I don’t know.

[00:02:15] Brandon Ware: No,

[00:02:16] Brandon Ware: let’s talk about the murder side.

[00:02:18] Jess O’Reilly: Okay. Because we have to move around a lot for work. We’re obviously sleeping in different places.

[00:02:22] Jess O’Reilly: So I know for most couples, one person sleeps on the right and one person sleeps on the left. Not in our house. People tend to have their side. For me, I just put Brandon on the murder side, which means if

[00:02:33] Brandon Ware: someone’s going to break in, I’m the closest to getting murdered first.

[00:02:38] Jess O’Reilly: Okay. But what about at this place?

[00:02:40] Jess O’Reilly: So we’re over in Barcelona, whose side is really the murder side? Because there’s the big, the big balcony doors.

[00:02:46] Brandon Ware: It, you know what? You never know. You never know. You know what? I’m, I’m, I flip flop back and forth.

[00:02:51] Jess O’Reilly: I’m a very scared sleeper. I should probably get some therapy on this. But even when I put my foot down on the ground to get out of the bed, I’m afraid someone’s under the bed and I’m.

[00:03:05] Brandon Ware: I always know exactly which side of the bed I’m going to take.

[00:03:07] Jess O’Reilly: The murder side.

[00:03:08] Brandon Ware: The murder side. It’s the murder side. It’s B’s side. Go on the murder side.

[00:03:13] Jess O’Reilly: Okay. I guess we should get down to this. Let’s do it. Okay. Scandinavian sleep methods. Sleep with separate comforters. Supposed to help you to sleep better.

[00:03:20] Jess O’Reilly: Regulate your temperature better. Thank God Brandon doesn’t want it. Sleep. Don’t sleep on the murder side. Yeah. Something like that. All right. We’re going to dive into the archives. Today for part two of threesomes. So now we’re, we talked last week. Now we’re talking about the how to, the planning, the safety nets, all that jazz.

[00:03:35] Jess O’Reilly: And this was a really popular episode when we first released it years ago. And I’m always being asked about threesomes. Everyone wants to talk about threesomes. So I think you’re going to like it before we get into it. We’ve got a great promo from adamandeve. com. They’ve activated. Code Dr. Jess 50. What is the 50 mean?

[00:03:54] Jess O’Reilly: Thanks, Charles. 50 percent off almost any single item, plus free shipping, [00:04:00] plus free rush handling. They’re going to handle these toys for you.

[00:04:02] Brandon Ware: Handle your package for you before it even arrives.

[00:04:05] Jess O’Reilly: Ship it to you so you can get off fast. And it’s fall sex fest over at adamandeve. com. I was checking out some of their best selling toys.

[00:04:11] Jess O’Reilly: They’ve got the Eve’s rechargeable thrusting rabbit. So it has an outer arm to play against the external clitoris. It’s got an inner curved arm that vibes against the G spot, but it also has a thrusting mechanism. They’ve sold 275, 000 of these. Code DrJess50 is going to get you 50 percent off, free shipping plus.

[00:04:31] Jess O’Reilly: Personalized handling,

[00:04:33] Brandon Ware: clearly they’ve sold hundreds of thousands of this thing with two arms and then a thrusting component,

[00:04:39] Jess O’Reilly: but have they handled all of all of them? Priority handled

[00:04:42] Brandon Ware: according to their website. They absolutely have handled them all for you.

[00:04:45] Jess O’Reilly: They’ve also, if you’re, if you’ve been waiting to try some of those suction devices, Eve’s Ravishing Rose Pleaser is on there again, 50 percent off with our code, Dr.

[00:04:53] Jess O’Reilly: Jess 50. And they’ve got a range of different wands and curves and vibes, and it doesn’t apply to every single item, but many. Most of these items are included. Yeah. Eve was freaky. So check it out. Dr. Jess 50 at Adam and Eve. com.

[00:05:09] Brandon Ware: Amazing. Let’s go and tickle some stuff.

[00:05:16] Brandon Ware: You’re listening to the sex with Dr. Jess podcast.

[00:05:26] Brandon Ware: Welcome to the Sex with Dr. Jess podcast. I’m your co host Brandon Ware here with my lovely other half, Dr. Jess.

[00:05:33] Jess O’Reilly: Hey, hey, just the two of us here to talk. threesomes. This is part two to follow up from last week’s episode with Justin Lehmiller, and I think this is going to be an interesting discussion because we’re going to share two things.

[00:05:47] Jess O’Reilly: One is a set of conversations and reflections to consider before you have a threesome. Sort of the how to prepare. And also, I wanted to share a bunch of your responses on threesomes because I [00:06:00] received a gazillion. So I’m just going to read them at random. I’m not cherry picking them. I kind of just picked a whole bunch out totally at random because yeah, I’m fascinated by what other people have to say about their experiences or their desires.

[00:06:14] Jess O’Reilly: So I had put it out on my Instagram and asked folks who fantasizes about a threesome, who actually wants to have a threesome. And so, as we said last week, the data suggests that many people fantasize about a threesome, but not as many actually do it. And then somewhere in between, there are people who want to do it.

[00:06:29] Jess O’Reilly: But on my IG, and we had thousands of answers actually, 61 percent say they fantasize about having a threesome. 39 percent say they don’t. And then the numbers are pretty much aligned 59 percent say they want to have a threesome. And 41 percent say they don’t, you know, I thought there would be more of a differentiation between fantasy and desire, but for our followers, or at least the people who answered, it was just pretty much aligned, which is interesting to me.

[00:06:56] Brandon Ware: I would have thought that the number of people who desired a threesome would have been higher just because of its prevalence in the media and TV shows. It’s like everyone always. That’s the fantasy.

[00:07:07] Jess O’Reilly: Yeah. And, you know, according to Justin Laymiller’s research and research that came before it, you’re absolutely right.

[00:07:12] Jess O’Reilly: It’s in the higher, you know, 85, 89 percent range in terms of desire. I wonder too, though, if folks who maybe engage with my profile or, you know, followers. In our community also maybe a bit more reflective about what they want. So they’re not just watching porn and saying, oh, threesome. And I’m not suggesting that there’s anything wrong or basic about wanting a threesome.

[00:07:30] Jess O’Reilly: I’m not suggesting that there’s anything wrong with wanting to have a threesome. I definitely, it’s, you know, it’s a fantasy for me. It’s something that we’ve definitely explored together. But I just thought I’d throw that data out there. And then I’m gonna read through some of your responses, but before I do, I definitely want to announce.

[00:07:44] Jess O’Reilly: This exciting new sponsor with whom we’re working, and that is Love Honey. And you’re probably familiar with Love Honey because they have been in the business of sexual happiness for almost two decades, and I know that they were in the UK, but they’re really becoming a powerhouse [00:08:00] in Canada and the States as well, and obviously I know I work with many brands, but.

[00:08:04] Jess O’Reilly: Love Honey’s a bit of a standout for a couple of reasons. First and foremost, they recently received a couple of awards from the Queen of England. Right. Apparently. Queen’s getting her freak on? I guess so. You said it. I didn’t say it. You’re the Brit here. So. And secondly, they’ve actually been sponsoring my show on TSC all about sex toys.

[00:08:24] Jess O’Reilly: So I’ve become intimately familiar with Love Honey products. Uh, do you remember when the boxes arrived and the boxes were big enough for me to fit in? That’s how many sex toys we received. Boxes and boxes.

[00:08:33] Brandon Ware: copious amounts of sex toys thanks to Love, Honey. Yeah. It was, it was, it was a little ridiculous.

[00:08:39] Jess O’Reilly: Well, I loved it. I had to try them out. And it’s interesting because they seem to carry everything. Like, I have never actually seen such a diverse range of products. Everything from kind of high end brand name toys that you’ll be familiar with. from, you know, my other sponsors. So they carry everything.

[00:08:53] Jess O’Reilly: And they also carry like little tiny pocket sized travel toys with travel locks, which is really cool to me. Their Ignite line, they have lingerie and they have their own line of products, as well as the only 50 shades of gray licensed product line. And I thought I’d bring up one of those toys because it’s, it’s a bit of a standout in that.

[00:09:11] Jess O’Reilly: I haven’t seen a toy like this before and it is the greedy girl thrusting g spot vibe. And I was doing a demo of it on tv the other day and just watching this thing go is so cool. So it obviously has this bulbous head that curves against the g spot but it also is, I wish I could, it’s almost like a gentle spring, so it also thrusts on the inside, and then it has a curved clitoral arm for the outside, so it’s kind of got every single possibility.

[00:09:42] Brandon Ware: So it’s any partner’s perfect Toy because it removes any sort of additional responsibility to help the one partner get off,

[00:09:49] Jess O’Reilly: like lower the pressure. Yeah. And so they, they love honey as a big design team and they have, you know, a gazillion reviewers. I keep using that word, working on constantly improving their toys.

[00:09:59] Jess O’Reilly: So many of their [00:10:00] toys have. All these cool features, whether it’s, I keep going back to the travel locks and travel cases, because that’s really relevant to me since I’m carrying them in my suitcase. But I do highly recommend you check them out and you can check out the links in my show notes or just head to lovehoney.

[00:10:15] Jess O’Reilly: ca or lovehoney. com and you can use code DRJESS10 to save on, I think, pretty much… everything, which is a good deal because usually when there’s these promos, there are many, many exclusions, but this, this one is across the site. So do check them out. Love, honey. And we want to thank them for their support.

[00:10:32] Jess O’Reilly: And with that, it’s time to dive into threesomes. Let’s do it. All right. So last week we talked about the data with Justin Leigh Miller. And this week, I want to talk about considerations and conversations that make for better threesomes. And one thing that we continuously hear, and I think Justin said this, and I said this, and the research shows that when you prep for something, it’s almost always better, right?

[00:10:52] Jess O’Reilly: In terms of the building of anticipation, the excitement, the pleasure, and I think also just the outcome, right? When you’re prepared, it’s not just something you stumble into, you know, because you’ve been drinking in a hot tub.

[00:11:01] Brandon Ware: Yeah. The first time I heard about somebody talking about preparation was actually Luna Matadas at one of the trade shows.

[00:11:08] Brandon Ware: And she was commenting on preparing for King play and having discussions with your partner. And it wasn’t something that I had really thought about before, but when. Luna was explaining it. It made so much sense. You have this open conversation from the beginning. Everyone explains what it is they’re hoping to achieve, what they want to get out of it.

[00:11:28] Brandon Ware: And more importantly, what are we going to do after the sex or the play? Is done, which I just, you think about a threesome and I immediately go to pop culture. People are at a party, people have probably been consuming too much alcohol or whatever and then it happens and then it’s done. But when you think about planning everything and then, okay, who are you staying for food after?

[00:11:49] Brandon Ware: Are you spending the night? Are you leaving? What do you want to get out of it? It could make the whole experience so much better.

[00:11:54] Jess O’Reilly: Yeah, the afterglow or the aftercare is so important and you know, it’s interesting you think about a [00:12:00] party. I think about couples unicorn hunting because that’s who I hear from so often.

[00:12:05] Jess O’Reilly: Couples who want to find a third and the messaging from couples is pretty consistent and also very Predictable and fair. I understand that, you know, when you have something good, you want to preserve it. And so then you want to prioritize it. But in doing so, I think a lot of us, and I think we’ve been guilty of this in the past, don’t really acknowledge and deal with our own privilege as a couple, right?

[00:12:28] Jess O’Reilly: So I think that it’s so easy for a couple to say, Oh, we want to find a third person who will do this and do that. They have this laundry list of wants and demands. But they aren’t really always thinking about the third person. So I think that’s a really important piece that, you know, a threesome isn’t just about adding a third into your existing partnership or play.

[00:12:45] Jess O’Reilly: It involves creating a whole new three way dynamic and connection. And this doesn’t mean that you all have to play or interact in the same way or it needs to be perfectly equal, but you want to attend to the feelings and needs and boundaries and desires. of all parties, right? And having that laundry list of wants and demands from couples is a complaint that we hear from unicorns.

[00:13:05] Jess O’Reilly: And by the way, a unicorn is a single person who will hook up with a couple. Oftentimes it’s a cis woman. Oftentimes they’re expected to be bisexual. Of course, that is not always the case, but that focus on the couple or even the focus solely on one person’s pleasure, right? Like my husband wants this, or my wife wants that.

[00:13:23] Jess O’Reilly: It can make them feel like they’re being used like a prop, like physically being used like a prop or treated like a sex object, right? No affection, no conversation. And I think it’s important that if you are checking in with your partner, like your primary partner, if you’re a part of a couple, that you’re also checking in with this third person, right?

[00:13:39] Jess O’Reilly: Really showing concern for their… emotional and physical needs and other things we, I’ve heard from unicorns in terms of complaints is they don’t want to be hunted aggressively, right? When they’re just being kind of bombarded with messages as though you’re shooting fish in a barrel. Again, it feels very objectifying.

[00:13:53] Jess O’Reilly: And the last complaint I’ve, I’ve heard from unicorns is that they get outed without permission. Couples will sort of use them as a trophy [00:14:00] head and say like, we did this, we, we were with this person when they’re not ready to be outed. So I think it’s just really important that we think about. all three people creating this new dynamic as opposed to it simply being something for the couple.

[00:14:13] Brandon Ware: I mean, I would say that you don’t have to think about the unicorn if you’re willing to pay a sex worker and have the discussion in advance.

[00:14:21] Jess O’Reilly: I mean, you still have to think about them, but yes, it’s not in the same way. I

[00:14:24] Brandon Ware: didn’t mean don’t think about them. But what I mean is you don’t necessarily have to, you know, if you’re clear about you just want to focus on your own pleasure or the pleasure of your partner and not that of the sex worker, could you not then?

[00:14:35] Jess O’Reilly: Make that request and pay for it.

[00:14:36] Brandon Ware: Make that request from the beginning and pay for it.

[00:14:37] Jess O’Reilly: Yeah, absolutely. But while also always acknowledging I think the humanity and the emotional experience of everybody involved, that’s another actually topic I’d love to cover in how we can, how folks who engage sex workers can make sure that they’re being really good clients.

[00:14:52] Jess O’Reilly: And I know we talked about that in the past with Andrea War Hunt from Modern Horror, and I thought her tips were really helpful as well. So I just kind of wanted to put that out there first and foremost, the piece around acknowledging couples privilege and doing something about it. And also, I’m not trying to make people feel guilty.

[00:15:06] Jess O’Reilly: You don’t have to feel badly. You don’t have to feel guilty. It is natural to want to preserve your relationship. It is natural to want to prioritize your own needs and the needs of someone you already know and love. We just have to remember that this is a whole new dynamic. And so I would love to read some of the responses I got around threesomes from folks, and it’s just this huge range of perspectives about whether or not folks want to have a threesome.

[00:15:29] Jess O’Reilly: So one person says, I’m not going to say any names, it’s the greatest gift to give the one you love. Pleasure. Okay. Someone else says, I’m I want to try both MMF and FMF, I think there’s a lot to learn about sex from both. This guy says, if I want to disappoint two people, I’ll just have dinner with my parents.

[00:15:50] Jess O’Reilly: I got a lot of messages from folks who said that they’ve had them and they’re kind of overhyped. This person says, I’ve had them and either I’m so concerned about making sure everyone involved [00:16:00] is happy or I’m the one left out. So it can be kind of hard to engage three people. This guy says, I need to find someone who can last as long as I can so that she can enjoy two guys the same length of time.

[00:16:10] Jess O’Reilly: That’s interesting. So for some people, I’m sure that’s true. For me, that wouldn’t be true at all. Like the lasting, I presume that means like erection prior to ejaculation. I know I make it sound so sexy. Um, I’d be less concerned about how long like that lasts because there’s lots of other things to be done.

[00:16:24] Jess O’Reilly: Somebody says, I’ve done it many times. It’s fascinating. Love when both the girls suck. And then smooches each other. Okay. If you’re in a couple, make sure you debrief after each time and share any newly discovered limits. Okay, good one. You might not know your limits the first time, so use each experience as a learning op.

[00:16:43] Jess O’Reilly: True, true, true. Couple people just said, I love threesomes. I love threesomes. Asking me if I want to have a threesome with you. No thanks. And then just reminders that threesomes can be fantastic, sensual time, but everyone should talk first and get comfortable. Another person says, yes, it’s my dream fantasy to have a threesome.

[00:16:59] Jess O’Reilly: It can be MFF, MMF, love to explore sex always. Some folks are asking how they can convince their wife. And I’ll suggest you go back to previous podcasts about how you don’t convince somebody, you present and discuss. This person says, I’m not sure I could handle that. I’m monogamous and sex is highly emotional for me.

[00:17:17] Jess O’Reilly: So I think it’s really good that he knows his limits. Some folks say it needs to be planned and agreed upon first as to who is doing what. And we’ll get to some of those questions. Ooh, this person says, three months postpartum. I had my virgin threesome with two men, double penetration. And then they just wrote, fun.

[00:17:36] Brandon Ware: They went, they went for it.

[00:17:38] Jess O’Reilly: I love it. I love it.

[00:17:39] Brandon Ware: That’s impressive.

[00:17:40] Jess O’Reilly: This person says, I feel it will ruin things in the long run. Fair enough. And that may be the case for some people. Sorry, they added more. I can’t handle the thought of my wife with another man, and I’m sure the same for her. So it’s good that you, again, know your limits.

[00:17:52] Jess O’Reilly: You don’t have to do everything. A bunch of people just wrote, It’s overrated. There’s a lot going on. I always feel like I need to process a lot after, and like I wasn’t [00:18:00] fully. Present. That really makes sense to me. Like just the overwhelming physical interactions sometimes can be too much.

[00:18:08] Brandon Ware: Yeah, there’s a lot of comments about, I mean, the initial few comments, people wanting to make sure that all parties were pleased.

[00:18:14] Brandon Ware: I think that’s really, it’s just a much more. thought through process that I don’t think I would have been as focused on if I was doing it for the first time.

[00:18:22] Jess O’Reilly: Yeah, absolutely. It can be very distracting, right? Like I hear from a lot of, you know, cis men, for example, who say that they lose their erection in their first threesome because there’s just too much going on and too much pressure.

[00:18:33] Brandon Ware: Yeah, I could totally see that being the case. And there’s just, I did like the response about wanting to disappoint two people going for dinner. That was great.

[00:18:42] Jess O’Reilly: With their parents.

[00:18:42] Brandon Ware: Yeah.

[00:18:43] Jess O’Reilly: So this person says that they used to plan threesomes earlier on in the relationship, but later they started to enjoy them.

[00:18:48] Jess O’Reilly: When they were more random and unexpected. So maybe with experience you can change the way you interact. I don’t think I could handle seeing my partner being intimate with another person. I’m too insecure. That’s fair. And it may not be insecurity. It might just be your own values. A lot of people commenting on communication.

[00:19:03] Jess O’Reilly: Somebody says the Eiffel tower is the best part of the threesome. That’s the sex position. I’ve been there, done that, was fun, but not something I’d consider again. If I was single, I would do it, but my fiance would not. Can you do it with friends? Can you do it with a stranger? So I’m going to suggest you go back to the previous podcast in terms of the data around who people are having threesomes with.

[00:19:22] Jess O’Reilly: Um, somebody says it’s a teenage goal. It’s overhyped experience. It’s fun 100%, but not life altering by any means. I would say that’s kind of my… experience as well. They say most men, it’s their holy grail. They want two women. This person says having sex with two people means overflowing with pleasure. I get totally lost in the moment.

[00:19:41] Jess O’Reilly: It’s absolute bliss. This person, this was a unicorn that says I didn’t like having a threesome with a couple. I wasn’t attracted to the guy at all. And then somebody says, I’m very insecure. I need to work on that first. It’s not where I need to be with my partner yet. Yeah, and I just want to say that you, you know, we all are varying degrees of insecure.

[00:19:59] Jess O’Reilly: Like one [00:20:00] day I might be fine with something and another I might feel really uncomfortable with it. And so you don’t have to necessarily work on that. I mean, if you generally are feeling insecure. To care. Sure, maybe you wanna work on that, but I don’t want there to be any pressure. So then there’s just a whole bunch more about preparing in advance, talking in advance, talking after.

[00:20:16] Jess O’Reilly: And then a lot of people who have done it saying it’s overhyped. So maybe I should put some, uh, polling out on that. Was it really hot or was it really worth it? So I just wanted to share some of that kind of raw notes from the community on threesomes. Before we get into, now, you know why we here, which is some of the questions that I think you can consider either on your own.

[00:20:32] Jess O’Reilly: with a partner with all three people before having a threesome. So I’m just going to go through them and starting really broadly with, why do you want to have a threesome? Because every damn group I work with, every group in the world, always, always, always people are asking me about threesomes. Like my data is 100%.

[00:20:47] Jess O’Reilly: I don’t think I’ve ever done a workshop where I don’t get an anonymous question about threesomes, always. And so my first question is, well, why do you want to do it? Like what appeals to you? about it sexually, physically, relationally, practically. So that’s, I think, an open ended question. So why do you want to do it?

[00:21:01] Jess O’Reilly: What benefits are you hoping to derive from it? Uh, what are the perceived risks and costs? I know people who have put together kind of a cost benefit analysis table. Uh, that’s how I think, so that works for me. I know that’s not everybody’s cup of tea. With whom would you like to have a threesome? Like, have you thought about that?

[00:21:18] Jess O’Reilly: Do you want it to be a stranger? Do you want it to be a friend? Do you want to engage Do you know if that person or those people are open to it. How might your relationship with your threesome mates change post threesome? What excites you most about a threesome? What motivates you? What concerns you? Do you have any hesitations?

[00:21:37] Jess O’Reilly: What emotional elements of a threesome have you considered? Because you heard in our community response that a lot of people talked about insecurity. There were also some notes on jealousy and all those things are fine. It’s okay to feel jealous. It’s okay to feel insecure. That happens and we can’t entirely avoid.

[00:21:52] Jess O’Reilly: negative emotions. And in fact, for some people, those emotions can become turn ons in a threesome. How will you manage potentially challenging emotions should they [00:22:00] arise? So like, what if I do feel jealous? Does it mean that it’s devastating? Does it mean that it adversely affects our relationship? Or do I just say, yeah, I feel a little jealous about that.

[00:22:08] Jess O’Reilly: I’m going to kind of file that for later and maybe go through it. at a later time? Or do I know that when I feel jealous, I become so physiologically flooded that I’m just going to freak out and run away, right? So how do you tend to respond to these, these feelings? Do you feel comfortable communicating your desires and boundaries, right?

[00:22:25] Jess O’Reilly: Like what holds you back? Are you good at this? Do you know what you want? How do you want to feel in the threesome? That’s always my big question for people, right? Like what is it you want to feel? What conditions? Increase your comfort with open communication. I think that’s a really important one, especially as you’re engaging with new people or a new person.

[00:22:43] Jess O’Reilly: Uh, what makes you comfortable communicating your boundaries? Are there certain triggers that stop you from speaking up? Uh, what does your ideal threesome entail? Right? Like, what is the setting? What is the type of relationship dynamic? Who’s involved? Specifically, what are the sex acts you want to engage in?

[00:22:59] Jess O’Reilly: Right? Like, we’re barely kind of scratching the surface here. What are the things you want to do with your hands? What are the things you want to do with your genitals? What are the things you want to do with your mouth? What are the things you want to do with toys? Where do you want to do it? How do you want?

[00:23:12] Jess O’Reilly: all parties involved? Like, will two people play while one person watches and touches themselves? Or do you want all three people somehow physically engaged? Like, would you feel left out if, I don’t know, they were genital to oral or genital to genital and you were, I don’t know, just playing with their hair or their toes or their chest or whatever it may be?

[00:23:30] Jess O’Reilly: I think we have to think about those specific things. I’m not saying you can plan it out and then it’s going to go exactly as planned, but if you can at least think about Best and worst case scenario, it can help you to decide your desires and boundaries and communicate them. And I think it’s just really important to, to remember that it’s okay to experience a range of emotions.

[00:23:48] Brandon Ware: When you’re asking these questions, I’m thinking about my own situation, what, you know, I’m comfortable with and not comfortable with. And it’s so interesting because as you’re talking through this, number one, all of these questions can. in [00:24:00] themselves become arousing and fantasizing like it’s, it creates a bit of a fantasy just having that conversation.

[00:24:06] Brandon Ware: But you had also made reference to, you know, how would you feel if you saw your partner for the first time and you felt uncomfortable, jealous, or any of those things. And I think even just mentally thinking about that situation kind of, for me, puts me into that situation so that I can think about.

[00:24:21] Brandon Ware: Initiating those feelings so that I can see how I respond rather than just boom, being in the situation and then all of a sudden being flooded with those emotions. So it’s almost for me a bit of a teaser in advance to be like, Oh, you know what? I’m thinking about this, you with somebody else. And yeah, I’m, I’m feeling a little jealous or I’m feeling insecure.

[00:24:40] Brandon Ware: So now I’ve put myself there and I’m already gauging how I respond, which I think would be a really helpful role playing scenario.

[00:24:47] Jess O’Reilly: Yeah, and you’re thinking about it from, like, definitely a coupled perspective because that’s, that’s our experience. But these questions are for everybody, right? So even if you don’t know the two people you’re playing with, you can still feel jealous, right?

[00:24:59] Jess O’Reilly: You can easily feel as though you’re not getting enough attention. You can easily feel as though you’re the third wheel. And so again, I go back to, okay, so what’s the consequence of that? Like, if I don’t get enough attention, is it the end of the world, or do I just feel a little off in this moment? Maybe I lose interest in the threesome.

[00:25:15] Jess O’Reilly: Like, what do I do if I’m no longer turned on because I’m not having my emotional needs fed? And so I think, for couples, I would add some additional questions. So we had, you know, 10, at least 10 there to begin with, which take a while to get through, but if you are in a couple, you want to kind of think about, okay, so how do you anticipate the threesome affecting your interactions with one another?

[00:25:33] Jess O’Reilly: How will you support one another before, during, and after the experience? How will you make sure you support the third party before, during, and after the experience? How will you make sure that you really think about this new dynamic and you don’t just prioritize yourselves? And how will you check in with one another during the threesome?

[00:25:50] Jess O’Reilly: How will you check in with the third, right? And it can be simple questions, like for example, you know, I’m trying to think if we’re gonna play with a group of three people, whether it’s a couple and a single or just [00:26:00] three people coming together, a question like, how will I know if you’re liking it, right?

[00:26:03] Jess O’Reilly: Or what will you do if you want more? Or you know, what are some cues I can look for in your body to let me know that something feels good? Or in the moment, it can be as simple as, do you like that? Like do you want more of that? Do you want less of that? Here or there? Just kind of giving people options and not assuming and actually threesomes must be a really interesting one and I gotta say like I’ve observed this so many times because again all of our models of sex come from porn but especially threesomes.

[00:26:31] Jess O’Reilly: Most people haven’t seen a lot of threesomes. People act really porny, right? I don’t know if you do not remember that from seeing that at parties and clubs like people being a little bit over the top, performative, and I want to be really clear, that’s not a criticism, because if that gets you off, then by all means, go for it.

[00:26:48] Jess O’Reilly: But what I’m trying to say is that, don’t assume that what they do in porn is what you need to do in your threesome, right? Because we have to remember, porn is a visual medium. It’s not a physical one, it’s partially audio, but they’re not focused necessarily on what the actors and performers are feeling.

[00:27:04] Jess O’Reilly: They’re focused on what it looks like for the camera. So even the way the three bodies set up, it’s so that you can see angles and perspectives that the camera likes. And in real life, you don’t have to worry about a camera unless you’re into that.

[00:27:16] Brandon Ware: Yeah, I mean, for me, porn is where I learned, I’ve saw other people having sex.

[00:27:21] Brandon Ware: So my being, when I was younger, the way I responded was based on what I saw in porn because I didn’t know on my own how it was supposed to respond.

[00:27:29] Jess O’Reilly: So were you like a jackhammerer?

[00:27:30] Brandon Ware: Uh, yeah, definitely. When I was younger, it was just like, I’m going to go as fast and as hard as I can, because that’s what I saw.

[00:27:38] Brandon Ware: And clearly I’ve learned. For me, that doesn’t always have to be the way that it needs to go. But I’ve learned that over time, and I’ve learned that by also picking up on cues on how your body responds. So you asked some great questions, which is when you speak to your partner or that individual or the people that you’re having this threesome with, it’s like, what cues can I pick up on?

[00:27:56] Brandon Ware: But it all goes back to having that conversation in advance, which frankly, [00:28:00] for me, would almost feel unnatural before you even had sex. Sex is supposed to be the spontaneous thing that happens as opposed to a planned situation.

[00:28:07] Jess O’Reilly: But what if it’s more playful than that? Like, what if you go for dinner, for example?

[00:28:11] Jess O’Reilly: Uh, and that’s something you want to talk about as well. Like, are you just getting together for the sex or is there going to be dinner before or drinks after or snuggling after? And, you know, I’ve heard from unicorns who say that, you know, when they are with a couple, they want to feel cared for, right?

[00:28:24] Jess O’Reilly: Just like you want to snuggle after, they may want to snuggle after.

[00:28:27] Brandon Ware: I’m not disagreeing with what you’re saying. I, I do very much like the idea of having the conversation in advance.

[00:28:34] Jess O’Reilly: So couldn’t you make it playful at dinner or even via text, like, what are you into? Like, what is it you want to try or what’s your ultimate fantasy or what turns you on?

[00:28:43] Jess O’Reilly: And I think that playfulness. can be a really hot discussion. So it’s not necessarily sitting at a boardroom table and going through a checklist of, yes, I accept pinky fingers in my bum, but not thumbs. I accept two fingers in the vaginal canal, but not three. I love when you play with my right nostril, but not my left nostril.

[00:29:00] Jess O’Reilly: Like it doesn’t have to be so regimented, although it can be too. Like for me, that wouldn’t bother me at all. I’d be happy to go through a checklist with you.

[00:29:07] Brandon Ware: No, I just like the idea of even the dinner or drinks or whatever it is that you’re doing in advance can be the foreplay, like it can be the lead up, the buildup.

[00:29:17] Brandon Ware: So, you know, for those that hour or two or however long. It’s anticipatory, right? Like you’re already getting riled up for what will come.

[00:29:25] Jess O’Reilly: Yeah. And you’re getting to know one another, right? Like you’re picking up on one another’s vibes. Uh, you’re picking up on their communication style. And we, you, I think we see this all the time.

[00:29:33] Jess O’Reilly: Um, not just for threesomes, but for any kind of group exchange. So for example, when we’ve. We’re places where couples are hooking up with one another, you know, you’ll see couples go to dinner and then they often, you know, go dancing after. And then maybe they, if there’s a hot tub, I don’t know why there’s always a hot tub involved, but there’s always a hot tub for these situations.

[00:29:52] Jess O’Reilly: They like go to the hot tub and hang out. And then it’s, it’s literally hours of building and conversation and getting to know them [00:30:00] before you actually. Get down to anything physical. Do you notice that?

[00:30:03] Brandon Ware: Yeah. And, and you know what, it creates some connection. It creates an environment. Like I said, the, the buildup, it’s a lot of fun.

[00:30:11] Brandon Ware: You made reference to something earlier and I’m just reflecting on it now. The idea of a notch on the belt or being just another, like another. And when I’ve had people approach me or us, and I felt like that’s all it is where question, you know, somebody approaches you, says something and then is like, Oh, you’re not interested.

[00:30:28] Brandon Ware: Boom on to somebody else. I’ve. I’ve been like, oh, okay. So yeah, that was, I mean, again, that was just my response, but it was like, yeah, that didn’t really feel that great.

[00:30:38] Jess O’Reilly: Like you’re, they’re only into, they won’t even have a conversation with you unless there’s a chance that you’re going to have sex with them.

[00:30:45] Brandon Ware: Humor me for five minutes, have a conversation.

[00:30:47] Jess O’Reilly: Well, that’s, it’s interesting because you probably don’t experience that much as a guy, but as a woman. We get treated like that by men all the time. Yeah. Right? Like if we’re not giving them what they want, they’re not gonna kind of quote unquote waste their time on us.

[00:31:00] Jess O’Reilly: And I think that’s a sociocultural… I guess norm around sex that you, you just are working to get to one specific goal and there isn’t the rest of the human interaction and connection and I do have a previous episode with Luna Matadas a long time ago where she talks about how unicorns are so often treated that way.

[00:31:21] Jess O’Reilly: Right? It’s just like they’re being hunted so hard. And so I think that’s something for all of us to keep in mind. Like, I will tell you, I remember when I think I was like 20 years old and I had first met you and I like we had talked about threesomes and I admit my only thought was how do we make sure we do this in a way that preserves our relationship?

[00:31:38] Jess O’Reilly: How do we find someone who’s a fit for us? Like nothing on my mind was about well, what? What kind of person, like how do I want to make them feel? What, what are they into? Um, and it was all like fantasy anyway. But I, I think that it’s just an important piece to remember that there’s all this privilege that exists within a couple.

[00:31:56] Jess O’Reilly: And it’s obviously not only when it comes to threesomes. It has to do with taxation. It [00:32:00] has to do with income. It has to do with how we live. That’s why it’s always my rule that if a third party comes out with us, like if one of my friends comes for dinner, I’m like, no, no, no, we pay. If there’s two of us, we always pay.

[00:32:10] Jess O’Reilly: I don’t know. We have dual income. Even though some of my friends have partners at home. It’s just kind of the way I think.

[00:32:15] Brandon Ware: Yeah, I, I, I agree. I mean, the, the focus has shifted over time and I think it’s more of a, I see the human in you, which is, I want to be nice to you. I want to make sure that you’re taken care of.

[00:32:25] Brandon Ware: And like you said, if we go for, for dinner with somebody, I guess that I’ve taken your lead on that, which is if you’re, if a friend or a third person comes along.

[00:32:34] Jess O’Reilly: We’re going to, I mean, my lead is always pay.

[00:32:36] Brandon Ware: Yeah.

[00:32:37] Jess O’Reilly: I hate being paid for like always pay. Um, and so as we have these conversations, right, and there are so many considerations here, starting with the very broad about why you want to have a threesome and how you want to feel in a threesome to the very specific, right?

[00:32:51] Jess O’Reilly: Like, are you willing to play with the anus? Are you willing to put your tongue here? What is it that you want to do very specifically? I think I also want to offer the reminder that. Most people don’t have threesomes, right? We talked about that data last week, and there are lots of different things you can do, even with these conversations, to kind of facilitate threesome light.

[00:33:12] Jess O’Reilly: Um, with a partner, whether it’s a long term partner or any sex partner, you know, simply just talking about it in bed, right, like talking about what it’s going to feel like, talking about the things you want to do, talking about the people you want to do it with, uh, and that can be very intimidating and very overwhelming.

[00:33:27] Jess O’Reilly: And as you said, that can give you a taste of how you might actually feel in the moment. And you might say, okay, I can push myself far enough where this is a huge turn on because of the risk, because of the jealousy, because, and I’m not that everybody feels jealous. I’m just saying, that’s okay. common experience that the jealousy can be a bit of a turn on on both ends, uh, and just talking about it.

[00:33:46] Jess O’Reilly: And that can give you an indication of whether or not you actually want to go through with it. Uh, there can also be kind of that teasing when you’re out in public, right? Like, um, talking about how you’re going to go talk to someone or maybe flirting with someone in a. [00:34:00] respectful way that you’re not leading them on or being untoward.

[00:34:04] Jess O’Reilly: And I know that flirting really varies from culture to culture, like some of our cultures, flirting is very, very open and normalized. And for others, flirting is something that we’re, we have to be a bit more careful with. Um, it could just be watching a threesome on film, like watching a scene and talking about what you want to do and how you want to do it and how you want to insert yourselves.

[00:34:23] Jess O’Reilly: Uh, some people are having virtual threesomes, right? Interacting with a cam model. In a private room and making sure you pay them generously for their work. It could be that you roleplay, right? So maybe I blindfold you and I play with like my hands and my tongue in a toy and I, I make it so that you can’t physically differentiate between, you know, whose hands are on you, right?

[00:34:42] Jess O’Reilly: I talk about how, how I’m gonna share you and how we’re gonna please you. And, uh, the nice thing about fantasy is that you actually don’t have to consider Anybody’s feelings except for the people in the room, right? So no, you know, you don’t have to worry about somebody else’s emotional needs. You don’t have to worry about whether you hang out after, right?

[00:34:57] Jess O’Reilly: The role play allows it to be whoever’s in the room at the time. Um, for some people, you can go watch threesomes. Like, I mean, I, I really have seen hundreds and hundreds and hundreds of threesomes or group situations. I’m not like counting them and I don’t, for me, whether there’s three of you or four of you or five of you, it’s kind of the same, same jam.

[00:35:14] Jess O’Reilly: Except for that whole couple plus one dynamic, which you have to be aware of. So even just going to a place where threesomes are happening, like a sex club, and not being a part of them, but being just in the vicinity of them, uh, and of course doing it respectfully. There are places where it’s meant to be exhibitionist and voyeuristic, and there are places where people are looking for privacy, right?

[00:35:33] Jess O’Reilly: Like if they’ve tied the curtains around a four poster bed, you’re not going to peek through the little slot. But they, you know, there are. Sex clubs with rooms where there is a, is it a one way mirror? So where you’re intended, where you know you’re going to be watched. Um, it could be that you don’t want to have a physical threesome with a third party, but maybe you just want to engage some watching.

[00:35:55] Jess O’Reilly: It could be that you go for an erotic massage and you [00:36:00] can choose to make it non genital. Right? It can just be erotic. And again, when you are working with professionals, please, you know, show the utmost respect. Learn everything you can. Uh, go back and listen to the Modern Whore episode of this podcast with Andrea Warhun for some perspective on how to honor and really show appreciation for sex workers.

[00:36:17] Jess O’Reilly: And of course, one, the number one way is to show your financial generosity because that’s why they’re there. Pay. Pay. A lot. Pay a lot. Tip a lot. Tip heavy. So we’ve spent two weeks on threesomes, which we don’t usually do. We don’t usually split the episodes, but I wanted to leave you with this. And what I’m going to do is I’m going to put the questions for consideration in The podcast notes, because I have some additional ones for you to consider as well.

[00:36:42] Jess O’Reilly: Some questions, not only on why you want to have a threesome, but also how you’re going to deal with distressful emotions, right? Like, are you comfortable admitting to jealousy, insecurity, distress, what makes you feel? jealous, insecure, and distressed. When you feel jealous, insecure, or distressed, how does it show up in your body?

[00:36:59] Jess O’Reilly: Um, what do you want to do in those cases? How can you self soothe? How can a partner or partners support you? What do you want them not to do? Uh, what are some cues to look for? in partners if you are feeling those emotions. So I’m going to put that questionnaire up there as well, as well as a specific questionnaire for couples.

[00:37:19] Jess O’Reilly: And I didn’t want to spend all the time on that today, but I can kind of quickly go through it before we wrap up. This is a questionnaire for couples to kind of moderate the Threesome within the context of the relationship. So whose idea was it? Do you feel any pressure? Have you indirectly or directly pressured your partner?

[00:37:37] Jess O’Reilly: What do you hope to get out of the experience? What are your concerns about the experience? What would it look like if it goes well? What happens if something goes awry? Like how will you communicate? How will you respond? How will you manage it within the context of your relationship with one another?

[00:37:51] Jess O’Reilly: What do you value in a third party, right? What type of person do you want to connect with? How do you feel about strangers, acquaintances, friends, sex workers? And what are you going to [00:38:00] do about your couple’s privilege? Like, how are you going to make sure that all voices and all desires are heard? and respected.

[00:38:07] Jess O’Reilly: So I think that there are questions that we can all consider and then there are some that are specific to couples. So I’m going to put those three questionnaires in the show notes, the general