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So many raw truths have gone unspoken in Six Vulnerable Conversations with Jeff Jacobson, a gay man. What really happened in the One Taste Warehouse? Will monogamy be replaced by polygamy? Six Vulnerable Conversations between a Gay Man (Jeff) and a straight man (Robert) gets down to basics and talk about sex. There are so many questions that arise when talk about the differences of our desires, orientation and experiences, and that juicy Death Trap kissing scene between Christopher Reeves and Michael Caine. Listen to the raw truth as we get real about our views on sexuality.

I’m here with another episode of Six Vulnerable Conversations Season three between myself and Jeff Jacobson, between the straight man and a gay man. In this one, we’re talking about sex. We’re talking about gay sex, we’re talking about hetero sex, and everything in between. His experiences, my experiences, our relationships to jealousy, and growing up in this culture that has such different biases and different sexual identification and their relationship to sexuality. Get yourself comfortable, hopefully it’s a big easy space. Thank you so much for joining us. For more shows, please visit Thank you.

132: Six Conversations 3.2 – Talking about Sex

This is show number two, season three of Vulnerable Conversations between a gay man, played by Jeff and a straight man played by me, Rob Kandell. Welcome to the show, Jeff.

Hi, Rob.

How’s it going?

Pretty good. I know we’re going to talk about sex today. I love the topic and I wonder where it’s going to go.

Any thoughts and feedback from show number one where we revealed a bunch of vulnerable stuff?

There was a part of me that was thinking about my family and friends hearing this. As a writer too, I notice that I’m all censor, then when I dropped the censorship it gets better. I really like reconnecting with you and felt like I had a good talking partner. What about you?

It was great. I haven’t released it yet so I’m waiting a couple of weeks to get it back into this flow. I was like, “I wonder what’s going to happen when it gets released? What are people going to think and say?” I’m just like, “Screw it.” I spent so much of my life hiding and trying to be something. My mom listens to all my podcasts, so I can’t hide a thing from her anymore. My mom can listen. I think my dad listens sometimes. I don’t even know what he listens to. You make the agreement with the universe to be vulnerable and transparent, to be someone who pushes for living unhidden. You got to do it yourself, so shut up or put up.

I’ll use a political speech as an example, and I think, “I can’t feel that person. I wish they’d get vulnerable.” Fine and dandy me wanting them to do it, but if I’m not going to do it then like, screw it. I’m not even kidding.

It’s all about the integrity. I’m doing a lot of guest interviews and I keep saying the same damn thing. Stop lying, stop withholding. To me, it’s a secret of my relationship. It’s secret to who I want to be in this world. We talk about it here, especially around the concept of sex. Let’s get to it. We’re avoiding the topic. Sexuality, straight man, gay man. Do you want to wax the poetic first around a little introduction on thoughts around what sex is for you?

I would say it’s an incredible form of communication. It gives me direct feedback on if I’m connected with myself and my desires or not. It also gives me direct feedback on my unspoken request and resentments and withholdings and victim-hood and over giving and under giving that I notice with my partner or partners.

That felt like ten times the previous. Communication, direct feedback and the things unsaid with the one you’re having sex with.

As well as access to or a lack of access to my vitality. What about you?

Sex has morphed and changed over my existence. I was actually scared of it when I was younger, wanting it so badly and then scared of it at the same time. I was an overweight kid, which really has set the standard for the rest of my life. It’s been a mold. I wasn’t the first boy that girls would gravitate to. In fact, I tended to be the last. I was like the last one picked for the team and sit on the bench. “Pick me,” and then some girls

TL 132: Views on Sexuality

Views on Sexuality: Jealousy is a killer.

did pick me, not many. When I was younger I was scared of it because I felt inadequate. I felt unattractive, and so much desire and so much connotation attached to it. Then I’ve gone through this whole journey where now sex is really two-fold with Morgan, my lady, my wife. It is such a rich way, like you said, to get feedback and feel connected to her and know her. I want to eat her whole soul through her body is kind of this feeling. Then there’s another part of me that’s really not a non-monogamous soul so I struggle with that part, really respecting my relationship and holding container in our mostly monogamous world. Women are so attractive to me, so I flip between the two.

You’ve got that desire and then there’s what, if any, of those desires do you act on?

People have heard the story a few times, but I’ll say it again. When I met Morgan, right after OneTaste and after an awful relationship, a good person and I was not ready for the relationship. I’m really clear about that. I was screwed up. About seven, eight months later, I met Morgan. It was instant. I said to her, “I’m not a monogamous person. I don’t want to be monogamous. If you want monogamy, you might want to look elsewhere. It’s not who I am.” Then we started dating and I had experiences outside our relationship, and I was always very honest and very straightforward around it. What happened was every time I would go and have an experience without her or with another woman, it would get a little more distant. I would call it the ice frost. It would last come in sooner and last longer.

The distance between you and Morgan?

Yeah. “You can go,” and it just got cold. What happened was after I fell deeply in love with her rather quickly I thought, “This is the most amazing person I’ve ever met in my entire life,” and I still think that. I started to compare and I was like, “These experiences with other women are awesome but not worth the cost of this relationship.” Then I was like, “What do you want? Do you want me to be monogamous? I’ll do anything.” She said, “What I’d like is if you have an experience with another woman, I’d like to be there with you.” I was like, “Okay, I can do that. That’s awesome, best of both worlds. I’m in.”

It didn’t feel that you were compromising?

It didn’t. There are a few things. One, sex with Morgan had taught me the fabulousness of intimacy and sex in the same piece. The other women I was having sexual relationships with were friends and dear people I really cared about. There wasn’t love, there wasn’t that deep in love especially. It was just a different thing. I just preferred the depth of love I felt in the sexual experience with Morgan. I thought I was signing up for play and fun and threesomes and parties. What happened in the almost three years since that agreement, we just haven’t found the right something to have an alternative fun in our relationship. We’ve tried a good dozen times and it’s not Morgan, it’s not me, it’s just the right people and it just hasn’t fit. We’re basically been monogamous for quite awhile now.

Open to the idea of, but in practicality so far it’s like, “No, this is better than us trying something out.”

We tried. Every experience we have is fun for us because we’re just like, “This is not working for us.” We went to a sex party in Beverly Hills and everyone was on cocaine. It was just like, “The vibe here is awful. Attractive people, but awful.” That’s been our sex life.

I was talking to my partner, Terry, about this podcast and about what we’re going to talk about. I said, “I want to talk about some of the stuff with Rob. We’re really looking at being vulnerable and I want to honor our relationship and not divulge stuff that you don’t want me to divulge.” He’s sweet and he and I talk a lot about sex. We talk a lot about sex with other people. He basically said, “How about if you just really focus on your experience and share generalities of our relationship?” Some of the more personal stuff on his side, I’ll talk around or be general or leave out. Even a conversation about having this conversation with you, having that with him was interesting. Slightly confronting, really sweet and awkward and intimate. I definitely wanted body parts inserted in other people’s body parts to have that sense of intimacy, and sometimes it’s those conversations way more than the action that does it.

We are not monogamous. We started off not monogamous. We definitely wanted to keep it that way. Both of us have tried monogamy before. Let me be clear, the way we define it is we are sexually non-monogamous. We’re sexually open but emotionally monogamous. I have been emotionally non-monogamous too. I was in a relationship with a couple, and also dating another man; three people, a couple and this guy. I definitely loved all of them. When I met Terry, pretty soon into it I realized, “I did some digging this guy,” but we know from past experiences and in being honest with each other and our desires and the amount of time that I travel for work, we wanted to stay open sexually and that has been fabulous and a pain in the fucking ass all at the same time.

What has been the challenging part of your non-monogamy?

I would say on both sides jealousy. Learning to burn with jealousy, learning to recognize that we’re feeling jealous versus it wanting to determine how I communicate with him. I think we’re both embarrassed. I’m 49 and he’s 58. We’re like, “Really? We’re still jealous of this shit?” We have this expectation that it’s for teenagers. It’s certainly not for us. Sometimes, it’s jealousy that the other one is having fun with someone else and showing intimacy with them and not us. For myself, I want to be out there having a hot time with a guy or a three way or a group or something at work or whatever. The resentment of my beloved having pleasure. When I say it that way, it sounds awful but it’s true that I feel that at that time.

Jealousy is a killer.

It’s tough. I’m not saying I’m really good at this but when I can just recognize, “Holy shit, I feel jealous.” I want to rage or scream or hit or punch or run around or runaway or whatever and just recognize it versus let it simmer and be in the background, I do a lot better.

I have a PhD in jealousy.

Tell me. I could learn from your dissertation.

I confronted it in the most extreme way for thirteen years. It started off with my first wife when we change from normal, boring couple to crazy out there exploration couple for five years. That’s where I learned my chops in jealousy. I had the same rage and insanity. I have the, “I’m going to walk for five miles in the foggy San Francisco night because I can’t stand to feel this much sensation,” or the nights like lying in bed and listening to her having sex with someone else. This is a funny story. I played racquetball. I’ve gotten hit in the ear with a racquetball about three or four days previous this experience. It blew my ear drum out so I couldn’t hear for my right ear. I’m lying in bed while she’s having sex with someone else, stuffing the other pillow into my other ear so I don’t have to hear and feeling grateful for the blowing out of my eardrum. “Thank you, God, that I can’t hear this.”

Thank you for this pierced piece of flesh in my inner canal. That’s when you know the desperation of jealousy.

It’s when you can hear it. Doing that and then going through OneTaste and living in a research warehouse with 50 people, walk around naked, everyone’s swapping beds, your partner having all these sexual experiences, feeling the abundance of everything. Morgan’s got it easy with me. I’m just like, “Please go have whatever experience you want. You’re a free woman. I have no hold on you. You’re free to flirt. Please, be free.” I’ve owned women in the past before. I have perception that I owned them, stopping them from doing what they wanted to do, which felt awful.

Have you had agreements in place or you exerted dominance?

Not even dominance, it was more like whining, “You’re having feelings when you’re having sex with all these people. You can go. It’ll be fine. I’ll just be sitting here slitting my wrist with a nail file.”

I am haunted by the story of jealousy that wasn’t mine personally. This guy I used to work with told me once when he was little, they lived next door to, I don’t know if she’s a single woman or she was married, but apparently she was pretty hot. His mother, accurately or not, was convinced that her husband, my friend’s dad, was lusting after this woman non-stop. They created an entire series of maneuvers or agreements. For example, their driveway ran down the middle between the two houses and I think her bedroom or her bathroom was on the side of the driveway, looking at across the different house. The mom, who worked from home, would back the car out every day and leave it running in the street so the dad couldn’t walk down the driveway and possible get a glimpse of her.

The kids and the mom would always take the garbage out or if the dad did it, he’d have to do this really roundabout way. He’d have to do all the gardening except this one little patch. All this stuff about how he might end up seeing this woman through the window. I remember thinking, “That’s crazy. His mom was nuts.” Sometimes I’m in bouts of jealousy with my exes or with Terry, I’m like, “I totally know what that woman was thinking.” We’re about ready to build a moat around our house just so I don’t have to fill you in.

Is it the hot sex that Terry has with another guy is the possible emotion? What is the loss? What is the feeling that drives you crazy?

It’s the hot action. This doesn’t really feel that accurate but when it’s happening, I’m like a cocker spaniel with my emotions and my thoughts and feelings. Terry is much quieter and more introverted. I have these little fantasies made up that he’s just completely emoting and expressing all this stuff that I wish he’d say to me or tell me about with some stranger or strangers. I actually believe him. I’m not suspicious. I believe him when he tells me that it’s not happening, but when I’m feeling really jealous, I think in my heart I’m wanting that with him. Then if we’ve been fighting or just tired or where I’m out of town or he’s out of town and I’m really wanting naked time with him and skin to skin contact or I want his dick or rest of his body in my mouth and I think of him with somebody else, I just end up feeling lonely, but I think I choose jealousy over that one. Sort of morph it into jealousy, like, “He shouldn’t be doing this.” When I back up and think, “I just really miss him,” I don’t like that that I feel good dependent or missing him right now, so I’m going to be really angry instead.

Let’s shift from jealousy and more into sex because this is a talk on sex. We’re talking about raw sex. I’ll just be transparent. We talked about this bi-curious nature of me and still there’s agitation when I think about oral sex or agitation when I think about same sex. There’s this agitation and I actually think that’s the society’s programs into me. When you were starting to explore your homosexual side, we mentioned that briefly last time, was there a fear about anal sex? Was there concern? Did you feel disgusted by it? What was the emotion as you just start to discover this part of yourself?

Definitely disgust and worry. I was thinking about this earlier knowing we’re going to talk about this. Oftentimes, a lot of jokes about gay men, some of them may be blow job related, but most of them have to do with anal sex. It seemed like society conflates that with anal sex. Anal penetration, a dick in an asshole, not even rimming or toys or external anal play that is in the ass going in and out. That’s how I thought about it too. You asked me about exploring homosexuality and I certainly explored the thoughts of it and I hadn’t done anything with anybody until my early twenties. Thinking your asshole is dirty or shit comes out of it and that’s gross, as well as it must be just disgusting when one man wants to be with another man. I definitely had that. I feel like this can open up so many different windows and conversations. I have tried, I am wide open to the idea of it. I do not really enjoy being penetrated anally. There’s a little bit of a way that I can hold both, “It’s disgusting,” and “I’m not quite gay enough,” at the time. If you were really gay you could take it up the ass.

They call it catching, right? That’s the term?

That’s a little antiquated. Top and bottom or actival and passival, which I think is interesting. Actival is top, like being active and passival is bottom. A lot of the bottom that I fucked, they are definitely not passive. The Chinese they call it one and zero, like binary. The one goes into the zero. The first guy that I was with, the first man that I had sex with also became my partner. It’s like, “If this will send me to hell, I think I’m going to go to hell because this is fantastic.”

This is your first time you penetrated him?

Yes. Also just playing with each other’s butts and rimming and touching, like an external massage. I did not know there were so many sensations there. It really wasn’t until I started doing classes with Body Electric, which was probably about five years after I met him. Body Electric dealt with erotic massage, sexuality and spirituality similar to OneTaste. In some of the slow, gentle conversations and exercises and stroking and massage that I even loosened up enough to talk about it. Not just to say like, “Yeah, let’s fuck,” but what do I think about this thing? What are my thoughts about my own ass or somebody else’s ass? Also as a gay man, I don’t like being lumped in with anal sex as synonymous, because there’s so many other ways to have sex. I understand why that’s the case and I know that’s how society thinks about it, but it doesn’t feel accurate and I don’t like being conflated.

TL 132: Views on Sexuality

Views on Sexuality: Every single Hollywood movie that depicts gay sex, most of it is entwined with danger and violence.

Every single Hollywood movie that depicts gay sex, most of it is entwined with danger and violence.

Or AIDs or some kind of a disease.

Pretty much is anal sex and oral sex. That’s the extent of what I grew up with media. You’re conflating anal sex with gay sex, to what I grew up with was anal sex, rape and gay sex was all one big horrible sentence.

The guy taking up the asses of the victim, the weaker one gets dominated. That has definitely played out in my community. There are a lot of ways people want to play with rape fantasy or the top is a butch and dominant and calling the shots and the bottom is much more receptive. For some people, that is a total right turn on, but it doesn’t match what everybody out there is doing or wanting to. Let me ask you. You’ve already started talking about this. This is one of our fears that straight men are going to beat us up because we’re disgusting anal whores or something. Does it invoke in you violence or rage or fear that it’s going to happen to you or are you got to bust that up in somebody else? I really wanted to ask you, the straight men, what goes on for you or went on for you when you were younger, when you were confronted with his concept of anal sex?

I was lucky and I will put myself in a very lucky, privileged category. I’ve always been big for my size. I was overweight as a kid. I was large. I was tall. I hit six foot at thirteen or fourteen years old. I was strong. I was an athlete. I also grew up in an upper middle class neighborhood. I went to school with only white kids and Asian kids. No black kids, very few Hispanics. I didn’t really go very far outside of the neighborhoods. I grew up in that bubble where there wasn’t danger.

Then when I got older, I would go to New York City. I grew up in Long Island. I would go to New York City and there would be that little menace or theme or viewpoint or prejudice really when it comes down to that I’m in the city. If I go to a gay neighborhood, then I could be in trouble. If I go to the West Village, I could be in trouble or some guy could just like pick up on me and somehow pull me into an alley and take his way with me. To tell you the truth, it wasn’t really fear. It was just some story when it came down to it. I never felt it, I heard it.

It’s a story that maybe you just heard of, that kind of a general assumption but that wasn’t really a motivator for you.

It was pervasive in movies. That was the way gay sex was. It was just like you’re dominated and you were raped. It’s so interesting that that’s my initial feeling of gay sex was rape and violence.

It’s interesting but I don’t think you’re unique there. Here I was, raised to be straight. At some point, I had sex with women and married one, just one. I’m certain I can be non-monogamous. I’m going to be the man and I’m going to be penetrating this woman and I’m going to be penetrating the weaker sex. Then it’s like, “I think I’m actually drawn to the gender that is taught to be scary and dominating and rape-oriented.” I’m an athlete. I’m in good shape but I’ve never been big. I’m thin and not like the biggest Bruce on the block by any means. I think there was that little bit of like, “That stuff I’ve heard women talking about in terms of men’s violence and physicality and them not feeling safe.” It wasn’t like I didn’t believe it, but I didn’t have a lot of experience on it. It’s like, “If I’m saying yes to this, I’m exposing myself to that. That was creepy.” If I’m going to go from being the dominant one in a male female relationship to possibly being dominated. I’m like, “What the fuck?”

I can see that transition. Have you question your own masculinity?

Absolutely. At its worse in homophobic mindset, being a faggot is the worst thing you can do. You’re stepping away from your masculinity. You’re being worse than a woman, which is the lowest on the totem pole. Definitely that includes being a bottom, being the receiver of anal sex. From the homophobic sampling, that is the lowest that you could do and it’s disgusting and weak and completely emasculated. When it’s served up that way, it’s like, “Fuck, I don’t want that.” Then confusion when really becoming pro sex and pro-gay and pro queer and pro sexuality in many different ways, it’s like, “Great, now I’m just going to become this huge bottom because I’m not scared of it anymore. It doesn’t mean anything about my masculinity.” It just hurts, the tearing sensation is not good at all.

I’ve had a strap-ons inserted inside of me in sexual experiences and it’s a lot of sensation. Most of them I’ve enjoyed, and recently we’ve tried and it’s been painful. It’s been really painful. It’s really interesting to understand what that feeling is.

How was it for you when you first decided you try that or any other kind of anal sex? What, if anything, did you have to confront?

I have a memory of my first wife having a dildo and her enjoying that on herself and then her saying, “I want you to try this on yourself.”

You inserting it, not herself?

Right. I have this memory of masturbating and anally penetrating myself while standing and her watching. I know that angle was good. It was a lot of sensation. I do remember getting really turned on the way she watched me, like there was a real hunger in her eyes. She liked that.

You liked that she liked that?

I liked that she liked that because again, where I started off using sex with was validation. A lot of straight people and I assume most people, if I’m having sex with a partner, then everything is okay. If she’s putting out for me then she must like me, and everything should be okay with the relationship and that’s not true for women. I didn’t know at the time and I was just like, “Anytime she had sex with me then things will be okay.” If I was doing something to turn her on and look at me with those lustful eyes, then I am a rock star.

You’re validated. You have value. You can add that one to my list of sometimes how I have or still use sex. Validation, attraction, things like that.

We started our first sexual exploration with a group. We met this guy, I’ll just call him Jack. She really liked him and he was bisexual, so she was really excited. This is my first wife. She was very excited to have the MMF three some experience. We’ve mentioned this last show, but I was highly confronted by that. That blew me out basically on my mind.

Like too much?

There was so much sensation. The things I remember the most was that I had sex with her and I orgasm very quickly, a minute, 30 seconds, a minute, very quickly. He went on for fifteen or twenty minutes. What I know now about women and men systems about how they’re connected. I think she just wanted me to come so she could get to him. She started up. She turned the volume up high and it’s just like, “Are you done?” “Now go sex with the guy.” That fifteen or twenty minutes, that was a huge confrontation because he was much better at sex than I was.

Like more valid?

He had vast, more experience. He was a sexual thing his entire life. I was a guy to starting on the sexual journey, so I felt insanely jealous or envious. I thought insanely envious of his skills to last a long time and creates so much pleasure in my wife.

In that MMF, you didn’t experiment with anal sex on you?

No. We did experiment with oral sex, but not anal sex.

What about sucking dick? So many of the jokes that we all make, like guys giving head. Was that confronting for you?

Yes, because there was a desire. It happened for a few moments but I was out of my body, out of my mind. I was crazy. It was nuts.

Which is hard to have sex that way.

We were talking before and I had this memory of the movie Death Trap. Did you see that?

Yeah, with Christopher Reeves and Michael Caine.

I remember Christopher Reed and Michael Caine kissed in the first section of that movie. I must’ve been about fifteen, sixteen years old and Christopher Reeve was Superman. He was the guy you always wanted to be and what a huge thing he did by kissing another man passionately on video. That compared to being in this MMF with this guy, there was this element of, “I had this bias that this is the wrong thing or this is weird or this is different,” in my entire freaking mind.

We talked about this last time. You were definitely told that that is wrong even before you even know what sex is. It’s like a horror movie like, “I think there’s something in the basement. I don’t know who’s in the basement.” By the time you might experiment with it, it can be just terrifying. One of the first week long intensive I did with Body Electric, a lot of what they teach you initially is cock massage, different kinds of cock massage that isn’t about stroking up a hard dick until it comes. They basically say, which is really sweet, “You guys already know how to do that. You’ve been practicing it forever. Nothing wrong with that. We’re fans too and let’s try some other stuff.” In the first couple of classes that they teach, which are shorter periods, there is no anal play. They say that’s only for hygiene and because it deserves more time. The teachers are really careful to say, “We are not trying to shame anybody.” In its first intensive I took, there was modality with external and partial internal anal massage. They had the teacher and then there was this really hot demo guy who offered up his butt press to watch as it was happening. There was a lot of joking and nervousness amongst the students. They were always jostling around and try and see what’s happening on this massage table. I’m sitting there and I completely thought I was going to vomit and I burst into tears, and I was experiencing a lot of turn on at the same time.

I remember standing next to this guy. I put my arm around him and he’s like, “Are you okay?” I just put my head down on his shoulders and wept. The vomiting was short lived but it was really this weeping because it was so beautiful. The teacher was so respectful. It’s wasn’t about getting into this guy’s pants or raping him or anything. He willingly is up there on his hands and knees with his butt out and responding to these caresses and different oils and hand gestures and pressure with this palm and this guy’s hand. This was way before anything was even inserted. I was just like, “I had no idea.” Oddly I think I also cried because the man receiving seemed incredibly powerful. That’s not how I was taught to think of somebody receiving anal sex. It blew my mind. Then I had an incredible experience receiving that kind of touch.

That sexological bodywork, straight guys took that too. Then they had to confront touching other guys’ genitals.

Did you take that class?

I did not. I thought about it.

It’s not free of angst but it’s easier for women to consider touching another woman’s body than men doing that.

It reminds me about OneTaste. We would do these demos. We would do male stroking a woman’s genitals. That was our practice. What would happen is a woman will walk up, just take off her clothes. That’s the way we’re trained. Completely naked, lay on the massage table and Nicole or another person would stroke her genitals for fifteen minutes. The crowd would learn. In the first year or the second year, Nicole is like, “We’re going to stroke a guy.” Then she looked at me, “Rob, take your clothes off.”

You’re not seeing this coming?

No, we never talked about it. This is how Nicole is, she likes to raise sensation. She’s like, “Rob, take your clothes off.” As a dutiful student backing the main teacher, I took my clothes off and got stroked in front of fifteen, twenty people. I had my body image. I had my cock getting hard in front of them. I had all this viewpoints about how this was totally wrong but when the woman got stroked, it was normal. It was not really normal but it was normal for me and then to be in this position. Then she was like maybe three or four times over that year. One time, she did a Q&A with me on the table naked for a good 40 freaking minutes. I’m sitting up there naked and she’s like, “Maybe you should put your clothes on.” I’m like, “Yeah, thanks.” It’s a pretty intense, vulnerable place to be.

TL 132: Views on Sexuality

Views on Sexuality: We had to feel within the gay community, how much of the focus is on penetration and fucking or getting fucked.

I love what you said about this idea that for a woman to do that, that’s normal. That’s what we expect. That’s what she’s trained to do. As consumers of sex, that’s our right to be able to see a woman doing that. Then it’s like, “It’s gay sex. Am I going to expose myself that way?” That’s what maybe some of these women had been talking about being objectified. With Body Electric, most of the activities as well as just the hours and hours together, everyone is completely naked, which was very confronting initially. Then after an hour, it just seems so natural.

I have a friend, a gay man, who has never enjoyed giving or receiving any kind of anal play. He feels very fringy in a negative way. We had to feel within the gay community, how much of the focus is on penetration and fucking or getting fucked. He says, “I’m outside that norm. I don’t even feel gay because that’s not something that I enjoy doing with myself or with other people.” I really love to fuck and to recognize I probably have a really strong over emphasis on that, or what would it be like to be here and I could be an outsider?

What are some norms in the gay man world in terms of sexuality? Anal penetration or oral sex? Are there other kinds of sex that is normal as part of that you would consider normal? Normal is a hard word. Common probably is a better word.

Kissing, sucking dick, oral, 69, fingering, rimming and fucking, jacking off each other. I’m going to start to say something that I don’t know if they’re going to be more on the fringe side of gay sex or a more normal side, but it’s within the spectrum of it. Cum is another thing for a lot of people, like swallowing cum, Bukkake.

Why don’t you explain it for the audience?

Usually it’s depicted as someone lying down on the ground and men standing around that person jacking off and coming on that person; multiple people coming on. Also BDSM, restraint and being tied up. Some kind of impact play, whether it’s light slapping, spankings, hitting, punching, flogging, those seem to be common. Sometimes I think it’s because our aggression has been overly fed. I’ve done a lot of BDSM work with men and women together. For a lot of women, they talk about how confronting it can feel to hit somebody and also freeing. I would say the BDSM side, frottage, dicks rubbing together and dicks are going to get under dicks, dry humping. I would say exhibitionism and voyeurism and group.

That was my question. As you probably don’t know, group sex or threesomes is a big fantasy of a lot of heterosexual people but not a common thing. Would you call group sex more common on the gay side than in the hetero side?

Absolutely. If I just think about the amount of times I’ve talked with people about that, definitely the gay men that I know and some queer women, their experience with that is much higher than folks in the straight world. Common, yeah, it definitely feels more common. Any queer person I know, if anybody knows that said, “I’ve never had a three-way.” I’m sure there is but I can’t think of that.

You can’t say that with straight people.

The way a lot of gay sex is depicted, it’s like how straight sex is supposed to be depicted. The asshole is like a pussy. As you and I know biologically, it doesn’t work that way. Physiologically, it doesn’t work that way. That’s another thing that I think people suffer from is seeing porn where two guys are kissing, or two or three guys are kissing and then all of a sudden he’s bent over and there’s dick inserted in their ass. It must just be because the guys really hot and turned on, but there’s no lube in an asshole. Done correctly for most people, they need a lot of warm-up time, lube and fingers and caressing and checking in. “Is it too much, is it not,” before there’s ever something as big as a dick inserted. When just playing penis and vagina action is held up as the norm, a lot of people try it that way and they hurt themselves.

Must go slow. Must be well lubricated. PSA, per public service announcement, must use lubrication for anal sex.

Must use toys that have a flared base.

You mentioned toys in the beginning. What toys do you like to use?

Sometimes butt plugs. If I’m really relaxed, I definitely can play with them with guys, with their asses. Fisting is definitely I would say is not as common as blow jobs or sucking, but definitely is in the spectrum of norm. Floggers, I love flogging and being flogged.

I wrote down your list on my little pad. It’s a good thing. I work alone. People would walk by and say, “What he’s doing?” It’s a big list. I was thinking when I think about heterosex, when it comes down to it, it’s a smaller list. It just a smaller range of things than this list. I’m not to saying it’s not enjoyable, it’s just a different dichotomy between the two.

What would you include in that common modality?

Kissing, oral sex, vaginal sex, hand on genitals, BDSM if you’re turned into but I think there’s less and less percentage in the straight world than the gay world, from my experience and what I know. Mutual masturbation, not very common. Fisting, not very common for a guy and girl. Girl and girl, I’ve been told it’s more common because of a woman’s hands, but a guy and girl it’s not as common. Dry humping and cock outside on vagina, that is a thing that happens especially when you’re worried about birth control, that’s something. Not a big difference but it just felt like less in the grand scheme of things.

Someone like you, a straight man who definitely experiment outside the norm, hetero normative experience, probably have a bigger list. Maybe I have a bigger list, or maybe I don’t. It seems like folks that’s venturing into the queer world might experiment with norm modalities. Terry and I have talked about this before, lesbian friends that we have are going to talks that women who have sex with women will talk about and the comments people will make. They’re like, “How does it work?” Everybody’s so used to having a penis has to be present. You either have to have a fake penis or it’s somehow not as valid. You get these women say, “That’s not true,” and then listing all these things and blowing people’s mind.

What’s that great scene in Chasing Amy. I don’t know if you saw that movie. A lesbian character said to Ben Affleck, “What do you mean no penetration?” She waved his hand and his little eyes went to the back of his head. I learned so much from the movies. Do you think it’s easier for gay men to talk about sex than your perception of heterosexual talk, people talking about sex?


I have the same thought.


I think gay people have easier talking than straight people.

Why do you think that?

My bias and my prejudice is that because it’s guy and guy, there’s less shame connected to desires.

Women get more ashamed to talk about their desires.

Men are afraid to show too much of their kinky side. Everyone’s afraid to show their kinky side unless they have permission or a container. It feels like guy and guy is just like straight up, speak the truth. Gay sex also has a bias of an anonymous.

You could add that to the list.

Anonymous sex.

As a turn on, not just as a circumstance.

That’s the movies and that’s the gay clubs, is you meet someone, you bend over, you have sex, you go home. In heterosexual, it’s a lot more complicated, most usually a lot more complicated.

Obviously there are ridiculous extremes, but there’s some truth to them. We talked about this last week that you so you could say in a group of people, “This is my wife,” or she could say, “This is my husband.” People can have a variety of thoughts and reactions and whatever. By queer, I’m also talking about like a trans women or trans man talking about themselves and their relationship or for gay men saying, “He’s my partner, my husband,” or a lesbian says “She’s my wife or partner.” It automatically become sexualized. The queer conversation in the straight world always becomes about sex but straight relationships in the straight world don’t always have to be about sex. You can say, “This and my wife and she’s at the bank and here our kids.” You may think about them sexually or you may not, but because of politics and is queer okay, is it not okay, is it accepted or not accepted, sexuality always gets laid over that person or those people. It’s always a sexualized topic.

The only reason to be in a gay relationship is because you want to have sex.

The reason why it’s politicized and you have hardcore fundamentalist religious groups against it or for it is because an agreement around is that kind of sex okay? It isn’t always part of the conversation when you’re a straight couple. I guess the reason why I’m bringing that up, I can sound a little conceptual. It’s a little bit like talking about gay men, anal sexism is always pun intended, inserted into the mindset as you’re talking about it.

We’ll be talking more about love and relationships in show three. It’s good primer.

Maybe at some point I’ll tell the truth I received anal sex.

TL 132: Views on Sexuality

Views on Sexuality: Anal sexism is always pun intended, inserted into the mindset as you’re talking about it.

Do you want to tell people how to find you?

You can go to

You got an email address you want to give out?

You can do it at

You can find me at Thank you so much for participating and I’m grateful for your honesty. Tell Terry that I’m grateful that he feels comfortable you’re talking about this. It’s really important. Say the same to Morgan.

Morgan is used to me blabbing about relationship nonstop. It’s been two and a half years.

Thanks, Rob. Take care.

Thank you so much for joining us on Tuff Love, Six Vulnerable Conversations. Thank you, Jeff, for your honesty. Thank you for bringing out those parts of yourself that’s really scary to bring out. Learning and educating and helping others and hopefully it will create some space and reality for other people to be more vulnerable by your desires and your experience. For more shows, please visit Thank you so much.

Resources mentioned:

  • Jeff Jacobson
  • OneTaste
  • About Jeff Jacobson

    TL 132: Views on Sexuality

    Jeff Jacobson was born in Seattle in 1968, and grew up enchanted by the lush landscape, the long summer days, and the short winter nights of the Pacific Northwest. Once, when he was a wee kindergartner, his grandmother let slip that she was a “modern witch, who flew on a vacuum cleaner over his house at night to protect him.” Jeff had seen her vacuum cleaner. The cord wasn’t long enough to reach his house.

    But in bed that night, left alone with creaky sounds and branches scraping over window frames, he decided that having a witch for a grandmother wasn’t such a bad thing. Even if it weren’t true. Two years later, his second-grade teacher Mrs. Eliason read spooky ghost stories and hung cardboard decorations of bats, witches, vampires, and spiders from the ceiling of his classroom for the two months leading up to Halloween. With Seattle’s gloomy, wet afternoons as the setting, the spirit of Halloween took root in his heart, just a few inches over from where his grandmother’s witchy identity resided.

    From then on, he did his best to navigate the mundane world of school, chores, and everyday life, while his imagination often ran wild, and he read as many books on witches and All Hallows’ Eve as could get his hands on. In the third grade he spoke Pig Latin and other made-up languages with his friends, creating an early love of sound, linguistic study, and fascination with foreign cultures.

    Sports played a big role in his life. He swam on swim teams, ran track, played soccer and tennis, and was a springboard diver for six years. This, combined with the fact that he didn’t play dress-up as a kid, or stage musicals, gave him the false impression that he was just like every other boy around him (foreshadowing alert!).

    In college he took Asian Studies classes and dove into learning Mandarin Chinese with gusto, spent his senior year studying in 10 different countries in Asia. He went on to live in Taiwan for two years after graduating from college to pursue advanced Mandarin studies.

    In 1994, Jeff moved to California to begin a master’s program in Chinese translation and interpretation, and also joined a men’s group. Three months later he realized two things: that he was much more interested in community-based coaching than he was in being an interpreter, and that it was finally time to come out of the closet. Soon afterward he learned about the wider field of coaching as a profession, and became a certified coach, as well as a faculty member for the Coaches Training

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