His Bisexual Journey

Charles Demuth, SAILORS DANCING, 1917

HER: There were eight of us on the two queen-sized beds that had been pushed together in Jess & Jeff’s hotel room. I had just finished fucking Evan and was cuddling with him when I looked over and saw you enjoying a blow job from Crystal. As she came up for air, Jason placed a gentle hand on her shoulder and said, “Can I take over here?” I wasn’t sure if he was asking you or Crystal, but I think I remember you replying “Of course,” or something like that. I couldn’t pry my eyes away as he took your cock in his mouth and caressed your body with his hands. We had given a talk on bisexuality just that afternoon — with a particular focus on male bisexuality — and now I was watching the theory come to life in the most beautiful way.

HIM: Four years ago we wrote our first article on the subject of male bisexuality. I had just begun to take a few tentative steps in that direction and I was fascinated by a strange contradiction: among the open-minded swinger community, where almost all women proclaimed themselves to be bi-something or other, there was almost complete silence around the idea of their male partners having any interest in each other.

HER: This was frustrating for me because almost nothing turns me on more than the idea of seeing two men together. Here I was with a willing partner, but everywhere we went, we’d see lots of girl-on-girl action, and no guy-on-guy.

HIM: Interestingly, as soon as I came out as bi-comfortable, my admission was followed up by … absolutely no one. Which was fine, because I wasn’t expecting to lead any kind of parade. But it did mean that I had very few chances to explore my newfound interest. That all changed this year, however, when I vowed to be a bit more intentional about seeking out opportunities to explore with men.

HER: It’s funny how that works. Around the same time that you were thinking about more actively pursuing opportunities with men, I decided that I wanted to find a girlfriend, and within a short time the universe brought just the right woman into my path. I know it sounds trite, but there does seem to be a kind of power in the act of declaring exactly what you want.

HIM: It’s kind of hard to argue with that example. I started talking about it more openly here on our blog, and also on Twitter,  and on a personal level with our friends. Something amazing happened. The men, or sometimes their partners, started coming to us to express their interest, and sometimes to tell us shocking stories of their own explorations. A very good friend of mine named Sam, who I would have guessed to be the straightest arrow in the quiver, told me how he gave another man oral at a party and felt twenty years of weight lifted from his shoulders. Twenty years of weight! Clearly he had been aware of suppressing certain feelings for a very long time. I never would have guessed.

HER: Okay, that was incredible, but I had an even more amazing experience. At a party, under the covering din of happy voices, another friend told me of a trip to Mexico where his wife hired a male prostitute to come give him the full ‘gay experience.’ Like, I’m talking every move in the playbook. He said he liked everything but the kissing. I did NOT expect that!

HIM: But it was more than just stories. All sorts of opportunities began to present themselves, leading up to my breakthrough experience with Jason a few weeks ago at Podcast-A-Palooza Encore in Dallas. I would say it all started in March when our friends Kaitlyn & Colin came over to our house in Toronto. Anyone who has read that story would know that one of the many highlights was me giving Colin oral while I was on the massage table.  After that, not every playtime included male-to-male contact, but it became much more common.

HER: My favorite time was in New Orleans in August. As many of you know, we connected with Scott & April of Naughty Gym fame there. While I was busy falling head over heels for April, I was somehow also able to help you and Scott connect. It all started when April confided that Scott had an interest in trying a little bi-play. He thought you would be a good candidate, which, of course, I conveyed to you with much enthusiasm.

HIM: It turned out to be a fascinating situation, reflecting how both he and I had different approaches to bi play, both mediated by our female partners.  When April was giving me oral, he asked if he could join her. They took a team approach to my cock, and it felt amazing. He told me later that this was the explicit plan he had for trying oral sex on a man for the first time.  As for me, I waited until Scott was getting ready to fuck you. He was behind you while you were on your knees with your face in April’s pussy. Seeing him in something of a holding pattern, I asked if I could give him oral in preparation, as if I was playing fluffer for the two of you. It was obvious we both saw our wives as bridging our connection with each other.

HER: And, I want to give Scott huge respect for coming out publicly as non-monogamous and, recently, as bi-curious. We need more men with that kind of courage!

HIM: I agree wholeheartedly.

HER: A month after New Orleans, and six months since we had last seen them, there was a whole different feel when we met up with Kaitlyn & Colin again. As part of your birthday celebration, we spent the afternoon at Oasis Aqualounge in Toronto. It’s a fantastic club with a uniquely chill vibe. After a prolonged time of flirting in the pool, we went upstairs to the dungeon where we all took turns bent over on the spanking bench, testing our tolerances for the various instruments of punishment we had brought along.

With Colin & Kaitlyn

HIM: At one point, I got hard from spanking you, and Colin got down on his knees to suck my cock. This would be the first time I’d have any sexual contact with another guy in a public space. I felt a moment of hesitation, I have to admit, but I quickly reminded myself that I wanted to be more open about my interest in other men. That was partly because I’m a bit of an exhibitionist, to be honest, but also because I want to do my little part toward normalizing open play among men in lifestyle spaces. While the club wasn’t very busy, some people did peek in to see what was going on. I glanced at their faces for signs of discomfort, but if they felt any, they hid it well.

HER: A few moments later, when it was your turn on the bench, it was clear you weren’t loving the flogger.

HIM: Yeah, it’s not really my thing.

HER: So we all switched to stroking and teasing you, which I knew you’d appreciate more. This, and me giving him a blowjob while he continued to touch you, got Colin close to the edge.  On a whim, I told him he should jerk off on your ass. It seemed like something you’d both enjoy. I hope you didn’t mind.

HIM: I didn’t mind at all because, well, I didn’t even know it had even happened until much later.

HER: What? How could you not notice something like that?

HIM: I don’t know, but I didn’t feel his cum at all. Assuming someone cleaned it up with a towel, it might have just blended in with all the other sensations going on back there that I couldn’t see. But I definitely don’t mind now that I know. I’m interested in racking up all the same-sex experiences I can get — at least the ones I’m comfortable with — to start to get a feel for what does and doesn’t work for me.

HER: Okay, so that brings up an important question: what are your limits when it comes to playing with guys?

HIM: Well, there are a million possibilities, just as there are with women, but one thing I’m not interested in at this point is receiving anal sex. When you and I have played with a strap-on or a dildo it always hurts, even at girths less than the typical male penis. There is no way I could handle that, at least for the time being.

HER: So you wouldn’t mind giving it?

HIM: No, at least not in theory. But you have to remember, anal sex is not exactly a big interest of mine with women. I’ve enjoyed it with you, but if we never did it again I wouldn’t consider it a big loss. Still, I might be interested with the right guy.  You have to remember, I’m way more selective with men than I am with women. If I find four out of every ten women attractive as potential sexual partners, the ratio is more like one out of ten with men. Or even less. Oral sex is the activity I’m mainly interested in with guys right now.

HER: Well, you definitely had the chance to indulge that later that same day in the hotel room with Colin. You both really took your time going down on each other, and Kaitlyn and I loved it. At one point I made a video of you blowing Colin while Kaitlyn used a vibrator on herself watching the two of you. Her tastes are clearly very similar to mine.

HIM: During the next week we got a message from Cate of Wanderlust Swingers saying we had to make a final decision about the subject of our seminar at the upcoming Podcast-A-Palooza in Dallas. While we had originally thought about doing a fun talk on the finer points of erotic photography, it felt like the universe was pushing us towards a discussion on bisexuality. While this was a bit more risky —  some people are still uncomfortable talking about any kind of male-to-male contact — we wanted to deliver a message of substance.

HER: Bisexuality isn’t just about men, of course. Women have obstacles to overcome, too. We are almost always expected to have a sexual interest in each other, even though some women aren’t actually into it.  And even those of us who are don’t want our same-sex attraction relegated to the status of an opening act for the main show. I’ve had some experiences recently, with April and with other women, that have transcended the standard performative model of female bisexuality.  I’ve discovered a level of real emotional connection, and it’s been transformative. I wanted to talk about that in our seminar as well.

HIM: That kind of sealed the deal for me, feeling like we both had meaningful issues to address in Dallas. Our main message was not that everyone should be bisexual, but that everyone should consider it. We felt that too many people were struggling under broad misconceptions: that female bisexuality was chiefly for the benefit of men, and that male bisexuality only makes everyone uncomfortable.  Few of us were fully enjoying the possibilities that the other half of the population had to offer.

HER: Dallas was a whirlwind. Once again, Cate put together an outstanding event with her seemingly unlimited energy and attention to detail. Everything was perfect, including the guests, who were all fascinating, kind, sexy humans. We had so many amazing conversations and made some truly profound connections.

HIM: Still, I didn’t know what to expect at our seminar. Yes, many individuals had said encouraging things to us privately, but attending our talk would be a whole other matter. I wondered if some men might be nervous being seen by other men attending a talk about bisexuality.

HER: As it turned out, there was nothing to worry about. The audience was surprisingly large, and, even better, keenly engaged. There was a lot of eye contact coming back at us from the crowd, and people didn’t hesitate to share their own thoughts and experiences when we gave them the chance. We also had a group of people who stayed behind after, wanting to thank us for taking this on. It was very gratifying.

A scene from the Dallas orgy

HIM: That night we were invited to attend an orgy with an amazing group of people we had originally met through Twitter. Interestingly, while all of them had responded very positively to our talk, none of the guys had come out directly and said they were interested in bi-play. Which was fine with me, since it’s not something I require. Besides, the women were all spectacularly attractive, so there would be no shortage of fun partners to explore with. So the eight of us — you & me, Evan & Crystal, Jason & Skylar, and Jess & Jeff — decided to convene in Jess & Jeff’s suite, which was ideally set up for an orgy.

HER: The level of play was sensational. These are just such amazing people. And to think we hadn’t known any of them a year ago. We all felt so close. But I think the thing I’ll remember best years from now was your interaction with Jason. So much happened!

HIM: After he took over from Crystal, Jason sucked my cock at length, teasingly, just the way I like it, while I caressed his head and shoulders appreciatively.  At one point when he paused, I beckoned him forward, so that he was kneeling between my legs. I started touching his cock in every different way I could imagine. I think he liked me pressing gently on his opening with the tip of my index finger best, but I’ll have to ask him the next time I see him.

HER: I loved watching the two of you, but I was disappointed that you didn’t also suck his cock. It seemed like he was putting more into it than you were.

HIM: That’s so you — always keeping score. Not in a competitive way, but you always want things to be fair. I’m pretty sure he didn’t feel there was any inequality of enthusiasm. I was really focused on pleasing him. I don’t know if you noticed, but at one point I was tracing the head of his cock around my ass. As I mentioned, I’m not really  open to anal sex at the moment, but I really enjoyed playing with the idea of it. Overall, I was open to going wherever our mutual energy took us, but that just never led to me putting his cock in my mouth.

HER: How did you feel when he kissed you?

HIM: You know, I’ve only really kissed a man on the lips once before, and I have to admit, I found that guy’s goatee distracting. But Jason was smooth-shaven, and he has great lips, so I just went with it. He’s a really good kisser. But it’s all so new that I frequently found myself focusing on being good for him rather than thinking much about my own pleasure. There were definitely moments when I lost myself in the feelings — which is sometimes even hard for me to achieve with a woman — but there were other times when I was strictly in ‘giver’ mode, which of course is a special kind of pleasure in its own right.  I’m sure all that will evolve, though, as I get more experience. That’s why I want us to seek out bi-play opportunities as much as we can.

HER: That’s fine with me. I’m not sure if you noticed with everything you had going on, but Jess rode me while we both watched you guys. That girl has skills! Which isn’t surprising, because I know she dates women independently. So tell me, would you ever just play with a guy on your own?

HIM:  It’s funny you should ask. After we left the orgy and went back to our room, you were exhausted and quickly fell asleep. I, however, was abuzz with excitement. Of course, there were so many other amazing moments besides my time with Jason that we could have written a whole separate story about them. But lying awake in our bed, my mind went to him.

HER: Nice! So what were you thinking?

HIM: Okay, I’m about to do that thing I feel like I’ve been doing more and more lately on our podcast.

HER: What is that?

HIM: I’m going to share a fantasy at a level of detail most smart people generally avoid.

HER: You know you don’t have to do that.

HIM: I know, but I think there is value in speaking the truth, and maybe more value the harder it is. I guess I’m in the mood to test my resolve, so here it goes. I imagined meeting Jason alone in our hotel room the next day, strictly for sex.  He watches me as I get undressed, knowing it’s for his pleasure. I ask him if he wants to do that thing again, where I trace the head of his cock around my ass, and he immediately gets excited. As he kneels between my legs, I let him take his time, enjoying all the sensations. When I think he can’t last much longer, I start jerking us both off with our cocks pressed together, and we orgasm at the same time.

HER: Damn, that’s hot!

HIM: I thought so too, baby. I came really hard.

HER: Um, okay, we need to wrap this up . I’m really turned on and we need to go to bed. Like, now.

 

 

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