Unprotected Sex

B Tompkins Fuck Painting no52 2014
Betty Tompkins, FUCK PAINTING no 52, 2014

HIM: The subject of unprotected sex is an open and closed case for most lifestyle commentators. Just never, ever do it … except with your long-term, exclusive partner. The risk of an STD is simply too great. It’s an easy, one-size-fits-all approach that is criticism proof. But like most easy answers, the reality is somewhat messier.

HER: Reality certainly got messy last night! In the heat of the moment, with no dicussion in advance, you and I both decided to have unprotected sex with Jonathan and Tammy.

HIM: Yeah, it was amazing. But it didn’t come out of nowhere. The question of ‘to condom or not to condom’ began years ago with our first threesome partner, your ex-boyfriend Derrick. After a few times together, everything was going well but I noticed that he was struggling to orgasm. I guessed that the condoms were to blame, so I asked you about it.

HER: I had noticed the same thing. I was worried about STDs, but there were a couple of things about Derrick that made me open to considering it. First, he’s a doctor, so he understands the risks. Second, he’s a germophobe, and an anxious personality to boot. Third, he lamented many times that his love life was zero, and that I was his only outlet. Fourth, and maybe most importantly, since we had dated and remained friends many years after, I trusted him.

HIM: I have to admit that I had another thing in mind beyond concern for his enjoyment. I don’t know where that came from, but I had started to fantasize about him coming inside you and then fucking your creamy pussy afterward.

HER: The word creamy in relation to pussy is kind of nasty. You’re such a bad boy.

HIM: Baby, I don’t go looking for these fantasies, they just kind of find me. Anyway, we talked to him about it and, let’s just say, it didn’t take much convincing. And when we finally tried it, it was fantastic.

HER: But I thought it was something we could never do with another couple. The one-in-a-million combination of circumstances that made Derrick safe for unprotected sex would be at least twice as rare to find in a couple. But we did talk about it a lot.

HIM: Yes we did. I had a fantasy about a weekend getaway where we would invite a small group of trusted friends to the cottage, maybe ten people in total, and each of them would get tested in advance. In that way, you could have unprotected sex with anyone (or everyone) throughout the weekend, confident that you weren’t endangering yourself. It might be challenging to coordinate, but we would have our own garden of earthly delights.

HER: I think they did something like that for the Life on the Swingset Desire takeover. I saw them posting their test results on Twitter. That would make for a very fun vacation. My own version of that fantasy would depend on the same kind of preparation. I picture myself as a kind of ‘party favor’: tied up and blindfolded on a mattress where any man who wanted to could have sex with me.

HIM: That’s ridiculously hot.

HER: Yeah, but the truth is that neither of us have taken any steps toward making those fantasies come true. It is challenging enough to throw a regular lifestyle get-together without making sure that everyone is both certifiably clean and absolutely fuckable.

HIM: I will make it happen.

HER: Well, you are a planner, so if anyone can arrange it, it’s you. But as you know, most of the best things that have happened in our lifestyle adventures were completely unplanned. That was definitely the case last night. On the way to the hotel party, we were talking about who we might play with that night, and we both had different answers. In fact, we weren’t sure if it was the kind of party where there would be any sex at all.

HIM: But just in case, I told you before arriving that you could feel free to do whatever you wanted with whomever you wanted whenever you wanted, and you wouldn’t have to check with me first. That concept was in my head because the last time we went to one of these parties you told me something that kind of blew my mind. You said afterward that you had thought about taking the host into the washroom to give him a blow job and let him come in your mouth. Then, you would find me, give me a long kiss, and only then tell me what you had done. It turned me on like crazy that you had even considered doing something that was so bad in so many ways! And not asking for permission was a big part of what excited me.

HER: There wasn’t anything particularly sexy going on when we arrived, but as soon as I saw Jonathan and Tammy I felt something. They are a really nice couple we have known for two years. I had played with them a couple times (most notably at one of our pool parties), but we have never seen them with any kind of regularity because their kids and jobs don’t allow them much free time.

HIM: I like them a lot, too. He is a really sweet guy with, as you pointed out before, an astonishingly nice cock. She is short and pretty, with very beautiful breasts. I have also fooled around with her before but I was never sure if she was attracted to me or just being nice.

HER: After a fair amount of socializing, things jumped into high gear when I slipped away to get a drink while you were talking to a new couple. A woman in fishnets and lingerie had just been the subject of a ropes demonstration. I complimented her on her ropes, and she said I had too many clothes on. She pulled the top of my dress down and we started kissing and playing with each other’s breasts. She turned to Jonathan, who was standing beside me, and started undressing him too. She got his cock out and went down on him. She pulled me down so we could suck him together. Then another guy, who was standing nearby, figured he should get in on this, and he whipped his cock out. It was a little off-putting to have this guy just barge in uninvited, but my tied-up friend took him on. Then she stood up and I started licking her pussy through her fishnets. The uninvited guy ripped her fishnets open so I could have better access. (The frugal woman in me was horrified at the waste!)

The whole time this was happening, I kept watching for you, but you never did come around the corner. When my knees couldn’t handle it anymore, Jonathan helped me up and suggested we find our partners and go to the open room down the hall.

HIM: It was actually another friend who told me that you were up to something, so I was just on my way over when I saw you and Jonathan heading down the hall. I spotted Tammy and she and I started talking. It turns out we both like to take things slower than our Formula One spouses. A nice bond was developing between the two of us. After chatting for a while, I suggested we go into the room and see what you guys were up to. After watching for a while — you and Jonathan really put on a first-rate show, by the way — Tammy and I started making out. We slowly took each other’s clothes off and eventually settled in for some leisurely oral sex.

HER: After a whole lot of fucking and sucking, Jonathan and I were winding down. He took his condom off and I went to clean up. When I came back, we sat together in a chair to take our turn watching you two. I was stroking his cock idly, but I thought we were done. He asked if he could go down on me again, and he got me going quickly. I guess he felt the same way. He knelt in front of me and I played with his cock, which was very hard now. I started rubbing it against my clit and before long I was pretty desperate to have him put it in again. That’s a rare thing for me, to lust after another man like that. I asked if he had another condom and he said he didn’t. I felt in the pocket of your pants, and the condoms weren’t there. I wasn’t sure where your jacket was. I could have asked you, but you seemed to be having some success and I didn’t want to distract you.

So I began my mental calculations.  1. They had been telling us earlier in the evening that our party last summer was the last lifestyle thing they had participated in. 2. I knew we hadn’t had unproteccted sex since being with Derrick a few years ago and we’ve been tested since. 3. They are people we have known long enough to determine that they’re trustworthy and responsible. So I asked Jonathan if it was okay (with them both) for him to put it in. I reassured him that were were clean and safe, and he said they were too. So, much to both our delight and horror, he put it in … without protection.

HIM: I kind of thought that might be what was going on, and it turned me on like crazy, but I couldn’t tell for sure. Eventually, you came over to where I was seated on the couch while Tammy was straddling me while I licked her breasts. You started sucking my cock behind Tammy’s ass, which felt fantastic. Then you rubbed my hard cock against her ass and pussy lips. You asked Tammy if she wanted you to put my cock in her. At that point I asked you if you and Jonathan had done it without a condom, and you said yes. Tammy didn’t seem freaked out by this and said yes, she wanted my bare cock in her. She squatted above me, giving me a perfect view of it sliding in. To say that it was driving me crazy would be an understatement. Then I asked Jonathan if he would do you again beside us on the couch. I wanted to see up close what I had only imagined moments earlier. Watching his bare cock slide into you while Tammy bobbed up and down on top of me transported me to another plane of existence. “I’m going to come,” I said, “right now,” in case she wanted to deploy the ejector seat, but she stayed right with me. It was one of the strongest, longest-lasting, most consciousness-exploding orgasms I have ever experienced. Tammy loved seeing what she unleashed in me, as she told me the next day in a text message.

HER: After, as we all sat panting and sweaty on the couch together, I asked if everyone was okay with what had happened. There was a little nervous laughter, but all of us said yes, that we trusted each other, and we had all wanted it. It might have been ill-advised, but it felt right in the moment.

HIM: That probably for me is the miracle: that four responsible people reached the same conclusion about a controversial course of action in the same moment. Controversial in more than just the logical sense, it was a course of action that could have had serious health consequences. You could say that it was four people in the grip of hormonal madness, but even afterward, as our blood chemistries were settling back down, none of us seemed regretful.

HER: Nope. Sore, but no regrets.

HIM: Okay, well I have one last question for you. You called me a bad boy earlier, and I’ll tell you that doing something bad at least partially fueled the spectacular orgasm I had. Was it a factor for you?

HER: Of course, but it’s not simply that. In the past, I have had two different men try to put it in without a condom and it really bothered me. It was bad, but it felt unsafe, like this was how they did it with everyone, so it was not a turn on. The difference this time was that I trusted Jonathan, I knew from past experience that he always used condoms, and we both agreed to it in the moment (it wasn’t sprung on me without my consent). So, the ‘badness’ was tempered by a feeling of safety. And that seems to be the magic combination for me. I need a framework of trust in order to let go and enjoy the taboo, whether it’s light BDSM or, in this case, bareback play.

So, while readers may be tsk-ing as they read this, all we can say is it felt right. Let’s be honest, this lifestyle is not without risks — physical and emotional — and it very often requires you to make decisions intuitively in the heat of the moment. Sometimes those decisions will end up causing pain, but, if you are sensitive to the character of the people you are with and confident that you know what your partner is comfortable with, then you’ll probably have more pleasure than pain. This time was definitely all pleasure.

HIM: For now, at least. We’ll let you know if we feel the same way in a couple of weeks.


  1. Anonymous says:

    It’s interesting how all kinds of lifestyles coexist within the “lifestyle”. My variant of the lifestyle is one that requires full testing. Specifically, I am tested each and every month, and I only play with those that are also tested. For me, playing with someone that is not tested is unthinkable. I get that unsafe feeling about anyone that is not tested, even in the presence of condom use.

Comments are closed.