Sex Lives chronicles the evolution of one person's sexual history. This week: Cooper, 36, in San Francisco.
I don't know if you remember the Sports Illustrated Swimsuit Edition with Tyra Banks on it, she has a red polka dot bikini on. That was ‘97 so I would have been in sixth, seventh grade at that point. I just remember thinking this is totally different than like the girls or women that I like. And it makes me feel differently. But I remember looking at that, because my dad had like a stack of Sports Illustrated or something like that. And that was the first time where I was like, Oh, this feeling is different.
I remember very vividly my first orgasm that was masturbation adjacent. So back in the really great days of Limewire you know, at a certain point of looking up music or movies you’re wanting to download, you realize that there's all this porn out there. This is a couple years after me realizing Oh, girls look good in bikinis; I remember being at home and downloading a lesbian video. And I remember having an erection, which at that point was like, it’s inconvenient but it goes away. But then watching that, and not really stimulating myself, but just watching that and having my erection grow more and more and then finally having an orgasm was crazy. I’d never experienced anything like that. Then once I kind of calmed down from This is nuts, I was like, Oh, I get it now. Because my sex education was always like, “Sex is for family planning. This is how you make babies.” No one had told me about the pleasure aspect of it, so after I had my first orgasm, I was like, I could do this myself. The lightbulb went off and if people had told me how good it felt, I probably would have tried it sooner.
I would say the first experience I had with someone else was with my then high school girlfriend. She gave me a hand job in the movie theater. You know Emmy Rossum? It was the Emmy Rossum Phantom of the Opera. The movie was awful, I mean it was much better than I expected, but not because of the movie. It was unexpected because it was my first girlfriend. She was much more experienced than I was even though we were the same age. We went to different high schools. But I didn’t think that sort of thing was going to happen; I was sort of under the impression that you kind of wait to share that with someone. So I was doubly shocked that she was she was down to do that and triply shocked that she was down to do it in a public place.
I didn’t lose my virginity until a few years later, actually. The girl from the movie theater, Sydney, we broke up when we went off to college. I should say she broke up with me. So I dated a few people throughout college, but I think one of the things that was really challenging for me is that I really loved Sydney. I would say, of the women I’ve gotten to know in my life, I've only really loved two: Sydney and now my wife. At the time in college, there were a lot of girls I really wanted to have sex with or be with, but I felt like I really needed to have that connection to make sure my first time was meaningful. You very quickly realize that college goes by fast, and so by the time it was my senior year, I was just like I cannot be a virgin at this point. So I started being more aware of opportunities and going to parties and meeting people. There was a house party where I met someone a few degrees removed from me; she was a work colleague for someone I was very close friends with and we hit it off. We had good chemistry. I was very lucky that the house party was close to my apartment. So I offered and said, “Hey, do you want to come over to my place?” And to my surprise, she said yes. And then that's how I lost my virginity.
We actually really liked each other. It happened over the summer before my last year of college. We were both in the area—she was working and I was taking summer classes. We dated for a few weeks after that and then she broke up with me. I think she realized I was looking for something more serious and she was looking to just have fun and that's okay, but I think it was hard when it happened. As it usually is.
I think the older I get the more I realize I'm just a very shy person. It’s very hard for me to open up to people and be comfortable with people. I deal with my own self esteem issues; I think most people do. I dated a few people between the woman I lost my virginity to and my now wife and I just never really had intercourse with them. Second base type stuff, but it never really progressed past that just because either the person didn't want to or the opportunity didn’t present itself.
On my second date with my now wife, we were at a friend’s house and she had made a joke about how “You know if you really wanted, I could give you a blow job right now.” And then maybe a few hours later after everyone had gone to sleep I said, “Oh, so is that offer still on the table?” and then that kind of happened. I wanted to hook up on our first date, but I was very nervous. I didn't think she liked me very much. I was very surprised to hear her voicemail for a second date.
Our sex life has actually been very tumultuous over the last six months or so. The reason for that is I think that sex is a very fulfilling part of our marriage for me. I love it when we have sex. I think we have very, very good sex. But sometime over the summer, she had approached me about the idea of operating an open relationship, an ethical non monogamous relationship. She wanted to explore other aspects of not only kink but her sexuality. And I said yes to that. I think the framework we had was not really a framework we were on the same page about. I think she wanted a little bit more autonomy and I wanted to talk through things a little bit more before we would execute on them. Just before Thanksgiving she had asked if she could be physical with someone that she had drinks with. I had said yes. I realized as soon as I said yes that I just was not okay with that. And she and I have been working through that for the last few months or so. The holiday season and into this year has been kind of tough for me. We're seeing someone as a couple together for couples therapy and working through that.
It’s hard for me to say how good our sex life is though because I love having sex with her. It's great. It's really exciting. It turns me on, it feels safe, it's sensual. A lot of this other stuff that I've been sort of working through recently has made it hard for me to be engaged in that way, though. Because I always wonder if she's thinking about someone else or if she’s sending photos to other people. She said no and we’re on a pause while we’re working though this, but it’s hard.
We still have sex, but not to the frequency that I would like. I don't need it to be every day, but I do think I'd like more of it. She's expressed to me that not always a situation of not wanting to do that with me. I think if she were here she would say, “One of the things that's exciting about that dynamic to me is that because of the open possibilities, my mind is stimulated differently. And therefore I'm able to engage differently and maybe more frequently.” So I go back and forth on whether or not I really believe that but I think I'm in this situation now where if the opportunity to have sex with her presents itself, I definitely don't overthink it.
When we had the conversation to initially open up the relationship, I think the idea appealed to me, at least in the abstract. One of the things that was nice about having that conversation was the feeling of, oh I’m not a dirtbag for feeling attracted to people that I'm not married to. Be it at work or the gym or out. What was kind of nice about it was the idea that I could be a little bit more upfront about things or people that I’m into or find attractive. There was the potential to maybe explore that with some other people that we know in our social circle. Obviously, when you get on these apps again you’re looking at things differently. I was really more open to it until it showed up at my doorstep. I liked the idea of it, but after this, I'm less interested in it. But the idea was that we were both mutually able to explore either together with people in group dynamics or separately. And I think now, I'm less inclined to explore separately. I wish she were less inclined to explore separately, but you know, that's the way it is.
This may sound silly but I actually wish that there was something about me or my wiring where I could be flexible as far as who I'm attracted to. The reason I say that is because I'm straight, but I think because of the way I carry myself, I actually get a lot of male attention. So part of me wishes I could be flexible in that way because maybe it makes thinking about an open dynamic easier; there’s more possibilities. I gotta tell you, being in San Francisco and dating in San Francisco before I met my wife, I think my type was alt girls who ended up being lesbians. I've accidentally been on two dates with men that I didn't realize they had seen as dates. I thought it was just a coffee-and-dinner kind of thing. So part of me wishes that there was more flexibility there because that maybe I'd have more fun, although maybe that's not true if you're just not into something like that.
I don't have a defined bucket list of things I’d like to do sexually, like I think a lot of other people do. I think the idea of a threesome with two women is intriguing to me. That's maybe the only group dynamic that I'm really interested in. Funny enough, my wife and I just recently tried anal sex together. We've been together for 11 years, married for little over six. I think that there probably will be more things we'd like to try, but I don't feel like I have defined things in a way that she might or other people might. What I really crave about sex right now is spontaneity. I have a job that is very demanding, and there's a lot of rigidity in my life professionally. So I look for avenues where I can really feel open and relaxed. So spontaneity, surprise, frequency, those are the things I think right now that I'm looking for more than like “wear this outfit and then we're going to roleplay in this way.” I could be open to that, but that's not necessarily what I'm seeking.
I was really surprised by liking anal. The thing that I think I was most worried about is I'm not circumcised. And so I was worried about the potential discomfort there. It actually felt really nice. It was a way for us to connect and communicate because you really have to go slow to make sure everybody is safe and feeling okay. And I ended up really enjoying that more than I thought I would. So that was a big surprise to me.
Two memories with my wife stand out as the best sex I’ve ever had. The first one, we’d been dating for maybe two months and we were at her apartment and it was just regular doggy style, but we both came at the same time. That's really rare for us. Usually, it's one before the other. What was so wild about it is I don't know that that's a position that we do a whole lot. But there was something about really being in sync that was super hot for me. The second one was when we were just starting to incorporate toys and things like that in our play. She took the Hitachi and she put it right under my balls and I basically had like a prostate orgasm without penetration. We're doing dirty talk, she is playing with me and using the toy. So I come and I'm still rock hard, which was a crazy experience for me. And I said, “please let's keep going. This is so hot.” And then I came again. I've never I've never had multiple orgasms outside of that night. It blew my mind.