Jess and Joe on ‘Side Sex’ and What Anal Sex Means to You

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I pegged a boy and I liked it.This week Joe meets Jess, a twenty-something woman, who has a lot to say on the subject of enjoying sex without penetration. This episode, all about sex on the side, pegging and anal sex, deals with the subject of what counts as sex with your partner. Does it have to be penetrative to be sex? Do you have to be a top, or a bottom? If you’re a ‘side,’ is it still sex? What if you just like pegging? As Jess says, “If you have an orgasm, it’s sex!”

Joe Kort:           Welcome to smart sex, smart love. We’re talking about sex goes beyond the taboos and talking about love goes beyond the honeymoon. I’m Dr Joe Kort. Thanks for tuning in.

Joe Kort:           hello everyone. Today my topic is for the show sex on the side, people who enjoy sex without penetration. Now when people hear that, they’re like, wait, what? What do you mean sex on the side without penetration, then you’re not having sex penetration is sex. That’s the way our culture seems to be going these days. That if I ask my clients, actually as a therapist, have you been sexual or have you had sex with the boyfriend or girlfriend that you’re dating? They’ll say, no, not yet. And then they’ll say, but we’ve given lots of blowjobs and oral sex to each other. And I’ll say, well, that’s still sex. Um, it may not be penetration. And so today I’m going to be with my guest here, a woman named Jess. Hi Jess. Hi. How’s it going? Good. Good. We’re going to be talking about when I call sex on the side.

Joe Kort:           So here’s the deal. I wrote an article in, I think it was 2014 for Huffington post about gay men who do not enjoy anal sex. So when would people hear about anal sex? They think, well, anal sex means you’re gay. And if it’s two guys, you’re gay. And if you’re a straight guy getting pegged, which we’ll talk about in a minute by a woman, Oh well I’ll talk about it now. When the woman wears a strap on and she penetrates her boyfriend or husband or male partner that, um, that’s gay, but that doesn’t explain gay men who never have anal sex. So does that mean they’re not gay? So suddenly their bud has to, to say something to them that, you know, they’re not really gay. I always say your anus doesn’t have a sexual orientation. It doesn’t know whether it’s gay, straight or BI.

Joe Kort:           It’s an anus. So it may, if it enjoys it and enjoys prostate orgasms, um, and enjoys, you know, uh, the prostate massage, uh, by fingers, by penises, by dildos. But then, and so when gay men in general are sexual, often they’ll say they’re either a top, they’re a bottom, um, or they’re a top verse or they’re a bottom verse. So let me explain how that, for those of you that never heard these terms, top is a gay man who inserts his penis into his partner’s anus. He does the penetrating, the bottom is identified as the gay man who is being penetrated, um, by the, by the top. Now, some people are versatile. They’ll go either way when there’s sexual with somebody. Now you do me and I’ll do you. Some people are mostly top, so they call themselves top vers, meaning I’m mostly a top, but every once in a while I’ll bought them for the person I’m bottom verse.

Joe Kort:           Um, I’m mostly a bottom, but every once in awhile I’ll, I’ll, um, I’ll top for the right person. So then I said, well, what about those gay men who don’t like anal sex and have never done it? And I call them sides. I made it up, right? If you’re not a top, you’re not a bottom, you’re a side. And I’m going to come out and tell you that I’m a side, that I have never had anal sex. I’m not interested in having anal sex. I don’t want anyone to perform anal sex on me. It’s not an erotic zone for me. And I’ve had people say to me, well, Oh my God, how do you have sex? Like what goes on in the bedroom as if everything else, the hundreds and hundreds of other ways of being sexual with a partner, um, isn’t sex. So I wanted to de-stigmatize this whole concept because I used to feel a lot of shame.

Joe Kort:           Like, if I’m not having anal sex, then maybe I’m not the right kind of gay. Maybe I’m not gay. These were my earlier Joe core days today. I say, Nope, I’m gay. And I’m proud to say that’s just not something that I enjoy and I have no shame around it. And what has happened is that article has taken off where it’s been quoted in various TV shows. It’s been, um, support groups have been developed around the country. When I go around the country, uh, people will say, I had our gay community center, we have our side support group because why do people need a support group? They feel ashamed of not having anal sex. Yeah. Have you ever heard of this?

Jess:                 Uh, no, but it’s confusing to me because whether or not you’re gay, BI or straight, depends on who you’re attracted to, not what orifice is getting stuffed with what. Right. So I don’t understand why that would, you know why a gay person would be like, Oh, well you’re not really gay then if you don’t enjoy anal sex. But there’s plenty of reasons not to enjoy anal sex. And I’m sure plenty of reasons to enjoy it. So it just, cause it’s not for everyone. Doesn’t mean that they’re not gay enough. You know? That’s confusing to me. It’s very, sex is still sex. Oral sex is sex. So I mean if you don’t view it like that, just looking in the terms of someone cheating on you and getting a blowjob, then all of a sudden it’s sex. Right.

Joe Kort:           That’s such a great point. Let’s say that again. So people who don’t think anything but penetration as sex. If they have our partner and they give a blow job or get a blow job, then they know it’s sex.

Jess:                 Right? Yeah. Cause now all of a sudden it’s cheating and you’re angry. While if it’s not sex, then what are you mad about?

Joe Kort:           Yeah. Oh my God. That’s very, very good. Yeah. I, I, what I’m trying to do is dismantle the binary, right. The binary being that I’m somebody is either a top or a bottom or you know, is being penetrated and getting penetrated and there’s so much emotion.

Jess:                 Yeah. That, uh, there’s a lot in between. There’s four play, there’s oral sex, there’s, you know, even just stimulation of like massage, not even, you know, prostate massage, but some of massage your butt long enough. Like you’re going to get excited. Yeah. Nail. There’s tons of nerve endings in there and that’s gonna lead to some sort of sexual intercourse. You don’t have to put it in a specific spot regardless. Something’s going in and out of something that’s still sex.

Joe Kort:           Yes. And I know that there used to be, I used to hear this a lot from straight friends and clients, female who would say, we have a secret in amongst women that if you stick your finger up to your partners, male partners, but I’m a little bit and sort of a do it without even telling them you’re going to do it. It’ll excite him if you say, I’d like to do this, he won’t want it. But if you do it without them knowing it will get them excited. Have you heard?

Jess:                 Uh, I haven’t, but that’s true. So you know it to be true, right? Yeah. Every time I’m like, Hey, you want a finger? Like people shy away from it. But unless, you know, yeah, they shy away from it. But if you just kind of do it, then it’s like a pleasant surprise usually.

Joe Kort:           And why do you think men shy away from it?

Jess:                 Uh, I think they’re under the impression that any sort of anal activity, whatever means that they’re gay, which is also stupid. Why? Again, it’s dependent on who you’re attracted to, not where you stick things. Right. So that has always confused me and frankly it doesn’t even make any sense. I don’t know why it became a widespread thing that people thought.

Joe Kort:           The only thing I can think about is that it’s, um, it came out because of the stigma, right? It’s men are stigmatized if they want to enjoy anything that has to do with two men together, which would be anal penetration. Right. But that doesn’t make any sense. Cause then now of straight couples enjoy painful anal penetration to the female.

Jess:                 Yeah. There’s the thing, it’s called pegging for a reason. Right? Is it called pegging when it’s to a man? To a woman? Not, no. I think it’s just when it’s like a female putting on something fake and using it for penetration on a guy. That’s what I’ve always heard it as like just anal sex if not. Right.

Joe Kort:           Yes. Cause we’re going to soon have, um, a woman who does all of her podcasting about pegging Ruby writers. So she’ll maybe correct us at that point when we do have around, but at this point, yeah. Yeah. It’s sort of confusing and um, but I do think it’s the stigma that a lot of guys think, well then this must make me gay. And actually there’s a book I had Justin Lane Miller on the show. Um, the very first time we did our show and he has a book called, tell me what you want. And in it he studied 4,000 Americans and he found in his study that 60% of men fantasize about receiving pegging. And 40% of females fantasize about giving pegging.

Jess:                 Well, I mean that makes sense. Like women don’t have a prostate, right? Men do. When you milk the prostate, it makes a man orgasm. So why wouldn’t you want all of your pleasant pleasures zones like explored, you know, and if you don’t at least try it, then you’re never going to know how good it feels. Like there is a very big difference between having a regular orgasm out of your penis and then having simultaneous orgasms from your prostate and your penis being, you know, explored at once.

Joe Kort:           It’s nice that you know a lot about this, especially as a female. A lot of women shy away from this information as well.

Jess:                 I’m more open minded.

Joe Kort:           You forgot to get hard jazz shoes,

Jess:                 but I wasn’t always. So you know, I had an Axe to enjoyed being pegged and I had never done it before and I did it. And that for woman, like it’s fun cause then you have all the power, right? You’re the one being, I mean granny you can do that on top too. I mean without, you know, a dildo or a strap on or whatever. But I mean it’s different when you’re the one doing extra. Like, Oh, it’s those weird role reversal like here, you know, but it’s, it’s actually pretty fun. So, and especially when you see like the pleasure that it causes your partner, it’s even more enjoyable.

Joe Kort:           I’m so appreciating you’re saying this because a lot of women in my practice, at least they get disgusted by it and they think it’s, um, they start to see the male as less alpha to, did you ever have that?

Jess:                 No, that’s childish. And my, um, that I, I think people get freaked out about taboo things and they let it affect their brain too much. Like you’re enjoying someone’s company or being sexual together. Just do whatever feels good. Who cares? It’s not like you have to tell everyone in the world. So you know, the only people that know are you in that person unless you go and share it with people and then you open yourself up to judgment, you know? But if you’re in the bedroom judging just, I mean you’re in there to let your hair down, right? You might as well go all the way and do it and explore all of the things. I mean, there’s going to be some things that make people uncomfortable. Obviously we’ll just don’t do that again.

Joe Kort:           You’re very open minded. It’s so, it’d be nice if so many more people were like this because the clients in mind, and again, I’m only talking about a clinical population, right? But really they’re in there and they say, well if you, you know, they get the worry that you must be gay if you want this. We have to get so, so the stigma doesn’t just harm men at harms women who then have to rethink men in some negative way.

Jess:                 Well, and then that’s adding even more harm to woman because now his female partners looking at him like he’s gay, but there was no man doing anything sexual to him, which I don’t really understand. That doesn’t mean you’re gay just because you have like it’s a pleasure zone. There’s a ton of nerve endings in there. I don’t know all the things about the prostate, but I know it makes my income. So you know, it’s gotta be serve more of a purpose a than whatever it does medically.

Joe Kort:           I just want so badly for these kinds of podcasts and education for people to understand. There’s nothing wrong with you if you enjoy this kind of Sachs and you would negotiate it consensually with the [inaudible]

Jess:                 partner. Well, yeah. And honestly, why are you getting, why are you even getting naked if you’re not going to enjoy it to its fullest potential? And why would you want to have a subpar, like sex isn’t something that’s supposed to be like, I don’t know, in the dark. And I mean it’s supposed to be fun, right? It’s the funnest thing you basically do. Even if you’re going sky diving, you’re going to get more pleasure from sex than you will from that. So if you’re going to go to the trouble of getting naked and you know, keeping a trim body to stay attractive, why not try everything that you’re curious about? Why not have like the greatest sex of your life? Why would you limit yourself? You know? And that’s really all it is doing. And it’s because of preconceived notions that don’t even really make any sense.

Joe Kort:           That’s so well said. So well said. Thanks. And, but I like it and I want to add that it’s also okay to have limits and to say, I don’t want to do this. Right. So that’s why you know, I, and people say, well, why don’t you want anal sex? What in? And I’ve thought a lot about it. Maybe because I was an enema baby, right? In the old, in the 60s of doctors would tell mothers, Oh, there’s your child’s sick. Maybe he hasn’t had a fresh problem movement. I don’t know what I said fresh four or, you know, uh, so they would give me an NMR. I remember that. I hated it and it was gross and it hurt and I, you know, um, and then later in life I just didn’t find it erotic. You know, parts of me felt dirty about it. Some of it didn’t feel, um, the older, I mean, I have lots of different ideas of why I didn’t like it at first. And it’s just, it’s just not erotic. I’ve tried a little bit with fingers. It just, it doesn’t do it.

Jess:                 Well, I’ll see like, you tried it now, you know, I don’t like it. Don’t do it again. Right. But people would say, I didn’t try it enough that I should try out a full penetration. There no reason to like force herself to be unhappy during sex. Like cause trauma to yourself, right? Clients. It’s enough hemorrhoids and women who say, I’ve tried it and I don’t want it. My husband prefers. And honestly like anal sex, if you’re doing it enough and saved someones members just that beg like there’s people that have had prolapsed anuses like it’s not exactly intended for our hard pounding of vaginas. Mouth can do a lot of, you can take a little bit of a beating, but I mean your anus like your, that’s different. You can’t just go to pound town all the time on an expect that there’s not going to be longterm health issues of some risk right away from that.

Jess:                 You know there definitely is. I know people that have had to be rushed to the emergency room from pegging, you know, so. So they’re not doing it correctly. Perhaps that is probably it. Maybe they didn’t use enough lube. I don’t know. But I don’t know. Is that, I mean it does, I don’t know like all the science about that. But if you do it often and long enough like does it cause longterm health issues or is it just if you’re doing it wrong and you didn’t dump a gallon, a loop in there or something? That’s a great question. And I think that I don’t have the answer to, but I would love to get an expert on them. I’m curious on that.

Joe Kort:           Yeah. So when we might get Charlie Glickman, Charlie Glickman is a sex therapist or sex educator and he, all of his books are about anal penetration,

Jess:                 begging. And so in addition, so he’s like the pegging experts. That’s like really right or anal sex expert, I guess.

Joe Kort:           Yeah, he would know that. And uh, you know, I think I should even know that just listening to my gay male clients, sometimes people will say, well, if you don’t have anal sex, how can you help other people enjoy and know how to have anal sex? You don’t have to be the one doing it. You don’t have to be performing the sex acts just to be able to educate people and do therapy, you know? And there’s lots of straight people who don’t want penetration, but they can’t let themselves know it because the gold standard in this culture is painful and a is penetration. The PIV penis and vagina or Pia, penis and anus. Sometimes. Some women are. So I have so much difficulty in so much pain. It’s almost like their vaginas saying to them, I don’t want this. This is, I’m not, it’s not erotic to me. I’d rather it be sexual and other ways. Right. Some men lose their ability to have erections and they can’t accept that because they don’t have other rep other things in their repertoire that they have to learn.

Jess:                 Right. Like how to give a blow job. That’s important. Right? Right. For everyone, gay, straight. Like if you have a manual life, it’s important. People think it’s not. It is. Yeah. You know there’s something dirty to it and a guy’s mind, I guess when you’re doing it, that just makes it hotter. So why not give your partner everything they want, but don’t go out of your way to do things that don’t make you wrong or that make you uncomfortable, you know?

Joe Kort:           Right. I mean, you have five, you have 10 fingers, you have a tongue. There’s lots of other ways to help your partner feel enjoyment and for you to feel enjoyment.

Jess:                 Yeah, absolutely. From your mouth, from hand simulation, like you said, everything doesn’t always have to be, you know, bottom half of your body actual penetration for you to have an orgasm. Like women, we have our strongest orgasms from the outside of our body. You know, there’s nothing that’s even internal that can really match what the clutter is, can actually do. So there’s no penetration involved in that at all.

Joe Kort:           Oh, that’s true. That makes a lot of sense. People need to know that. And with gay men, a lot of times, um, if they’re, uh, aside, they feel so bad about it because, uh, you know, and it might be that they enjoyed anal sex for a while and then stopped lots of gay male couples. We’ll let start Italy penetrating with anal penetration and then over time they’ll stop and then they feel shame about that. And the truth is, and they feel shame because they don’t understand that many people stop engaging in certain sexual acts in longterm relationships. If you can get things back, you can talk about bringing things back or you could decide those days are over for us. Maybe we bring in a third, maybe we don’t, but there’s lots of conversation and openness that people don’t have.

Jess:                 No, I think people are too scared to be judged or whatever. So they just avoid the topic because it’s uncomfortable or maybe they don’t want to upset somebody by, you know, but I mean, if you don’t talk about it, then there’s still gonna be feelings hurt or someone’s confused. So just get it out in the open and get it over with. Rip the bandaid off. Right. Yeah.

Joe Kort:           And I think a lot of people don’t understand that in the kink and fetish community, a penetration is not the gold standard all the time. It’s the roleplay. It’s the power exchange, right?

Jess:                 Yeah, absolutely. It’s definitely the power exchange or, yeah, definitely a of, you know, people who during their day job or you know, from nine to five, they have to be out and be aggressive and be the person who’s in charge. And although that’s their role as a CEO where an attorney or whatever, at the end of the day, like they’re not naturally a dominant personality. So it’s exhausting for them. So when they get around somebody that they trust and you know, you talk about things at a time and they can kind of be the one being dominated, that’s where they truly feel like, I guess a re-energized, you know, because it’s exhausting to be acting outside of your personality all day long, every day. And it may or may not involve penetration. Right. Right, right. Most times. I mean, it doesn’t, yeah. You know, for Dom sub relationship, quite often there’s no penetration, no sex. It’s a sexual fantasy, but also mentally relieving.

Joe Kort:           [inaudible] yes. It’s like therapeutic for them. Right. You know, a lot of porn shows men getting pegged in a dumb sob where she’s the Dom and he’s the sub and he’s, she’s being forcing him. So it’s almost like the stigma is, well, if she’s forcing me, then, um, that can arouse me. I can do it.

Jess:                 True. But, um, let’s just keep in mind like, uh, porn is rarely what happens in real life, right? So, you know, it’s just this woman who’s running around stomping on some guy with heels and it’s normally not that aggressive in girl world. Right. It’s all different ways. Those are just one. Yeah, exactly. So I don’t know. That’s interesting.

Joe Kort:           No, it’s helpful for you to be adding to this because a lot of people don’t understand this and having this natural conversation, I’m having all these experts on all the time and it’s nice to have just a regular person talk about this. Who knows what she’s talking about.

Jess:                 Yeah. It’s, it’s a interesting lifestyle to get involved in, but I mean, if you’re somebody who’s out and is out of their element most times during the day, it might be something that might be relieving for you. You know,

Joe Kort:           not in the gay male community. There is a lot of stigma to be in a bottom, the one who is being penetrated and there’s a terrible joke in the gay male community who pays for the wedding, the father of the bottom and really snow now. So massage dentist and so not funny. Uh, and the idea is that he’s more like a female. That’s why they do that. And it’s really upsetting and it’s true. They’re trying to change it in the gay male community to nappy this way. They did a study in a book called a billion wicked thoughts. And in that study they discovered that there are more bottoms than there are tops in the gay male community. So for us to be attacking a group of men who outnumber a group of other men is just so unhealthy

Jess:                 greed. Yeah. I don’t even know why it would matter who’s taking and who’s risk vol. Yeah. Who’s receiving and who’s giving, I don’t understand how that would make a deal.

Joe Kort:           Yeah. It’s a, it’s gotten attached to masculinity and, um, it’s really an unfortunate thing. And, and one thing that I do know amongst gay men, uh, not even thinking about penetration, just thinking anal li, a lot of gay men enjoy a mouth to anus. It’s called anal Lingus or remain where he’s looking the other guy’s anus. And I was on a gay male cruise and I did a workshop on it and I said, okay, I had everybody, uh, stand on one end of the boat if they enjoyed the sex act one out on the boat. If they didn’t enjoy a sex act and stand in the middle, if they were neutral about it. And I went through all these sex acts and then I said, okay, remain. And everybody went to one side of the boat that liked it. The whole boat was on inside [inaudible]. That’s how much gay men enjoy remain. But you have to be careful because sometimes they do it and they go to bathhouses where there are men who are, you know, walking around in towels and looking for group sex, individual sex, couple sex and they’re enjoying rimming each other. But sometimes is can spread, uh, equally and other kinds of problems, uh, if you don’t know where the man’s been or, or what’s happened and how clean he is.

Jess:                 Yeah. I think what’s really important for any sort of ass place. So before, um, with my ax before I would peg him, like he always gave himself like an anima, but it was the net home enema. So you know, the shower thing or whatever, put it up there and then jump on a toilet and let it all rinse out. That way. You know it’s about as cleanli as it can be for a butthole.

Joe Kort:           Yeah. Right. Yeah, and that’s true for gay men too, that the bottom has a little more work to do to be clean. Right. But then again, then there’s sometimes I’ve had clients say, well, in friends it wasn’t so clean and I pulled out and there were feces or whatever, and it’s just part of it. It’s an anus. Yeah, it happens sometimes. Exactly. So yeah. So I dunno, I think this is good conversation. Do you think there’s anything more we didn’t say about penetration or enjoying it or not enjoying it?

Jess:                 I don’t think so. I mean, if you have an orgasm, Oh, it was sex, so in some way or another.

Joe Kort:           Oh my God, I love that too. If you have an orgasm, it was sex. That’s how I see it anyway. Yes. Right. Yup. I think the only time that’s probably not true is when it’s rape. Right? True. Nonconsensual definitely. Right. I just want to make sure people hear that, but otherwise if it’s two consenting partners and you had an orgasm, I’m going to totally borrow that. If you don’t mind, that’s very, very good. And if you don’t like anal sex, there’s nothing wrong with you. If you do like it, there’s nothing wrong with you. That’s the whole goal of my podcast and my work is really judgment free zone and free yourself of your own shame and your own judgment that binds you. Doll this, if you’re aside, come out, if you’re a top or a bottom or versatile or whatever you are, come out. Just be up. Be okay with it, but be selective about who you tell and be real. Realizing that some people can be judgmental towards you.

Jess:                 Mm, absolutely. Which they shouldn’t because again, it’s sex. So anything you want to do should basically go within reason. Well and consent.

Joe Kort:           Yes. Thanks. And thanks for being on the show. A pleasure. Thanks for having me.

Thanks for listening to this episode of smart sex, smart love. I’m dr Joe court and you can find me on Joe court.com that’s J O E K O R t.com. See you next time.

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