On Saturday night I find myself all riled up with nowhere to go. I’ve just had a couple drinks with some friends in Hollywood. One of these friends is a DILF on whom I’ve had a persistent crush for quite awhile. The crush remains because there’s just enough flirtation to keep it going and yet absolutely nothing can be done about it because he’s in a committed relationship and has, well, kids. So the crush just lingers weakly in the background and flares up from time to time when conditions are right. This particular night, emboldened by alcohol, I find myself pulling his hair, leaning into him, and generally taking it a little too far.
That chapter ends without incident and I drive home, energized and not at all sleepy. I come to a fork in the road where I can either take a right to my house and my bed, or left to the local dive bar where I always make poor decisions. I head left. I park and purposefully walk into the bar. It is last call and the lights are coming up. The drunk crowd is streaming out. I blow past my friend the doorman and swim upstream towards the bar. The bartender I tried and failed to make out with on New Year’s Eve (he also lives with his gf) is working and I make a beeline for him. He looks happy to see me.
“Where have you been?” He beams.
“Hey John, you still live with your girlfriend?”
“Yes,” he says, “but my brother doesn’t.” He gestures to the bar where his brother sits drinking a beer. I smile and sit down, introducing myself with the line, “I tried to make out with John on New Year’s but he was very resistant.” I laugh. John shrugs.
“Don’t you know that kissing doesn’t count as cheating?” (Side Note: this is something my mom told me when I was 18 and I’ve been using it to my advantage ever since.)
His brother smiles, unperturbed by my verbal diarrhea—I like him already. He is built like a brick shit house, big muscular arms and a wide torso. He tells me he used to work at this same bar, now he’s a trainer in San Francisco. My haven’t-had-sex-in-over-a-month self is happy to see him.
John makes us some delicious lime-tasting shots and the three of us throw them back. The crowd has thinned to real locals and friends of the bartenders. Aggressively loud wall-of-noise death metal blasts from the speakers. One of the bartenders has stripped down to his underwear and is smashing glasses on the floor. I’m not sure why any of this is happening but it’s pretty hilarious. As John counts the night’s tips, I canoodle with his brother. I feel on his arms and put my hands on his chest and back. I ask if I’m bothering him and he assures me I’m not, smiling.
“I have a pretty girl touching me.” Then he adds this feminist-adjacent sentiment, “God knows we objectify you guys [women] enough.” He’s really batting a thousand with me.
John keeps refilling our beers as he counts his cash. At some point I grab his brother’s face and start making out with him. After this first kiss, he looks at John and flips him off.
“Fuck you, man,” he says, laughing.
I join in, also flipping off John. It isn’t very nice but I’m really enjoying this game. Despite the pissing-contest-ness of this moment, the brothers obviously have genuine love and affection for one another. There is the sense that John is happy for his brother in this moment, even if he does have mixed feelings about the scenario. I express this to them, saying that if I had a sibling, this is how I imagine we would be. We would share men and be cool about it.
At some point, John plops down next to me so I’m now sitting between the two brothers who are a year apart in age and both ridiculously good-looking. This night has really taken an excellent turn. John occasionally glances at us sideways, watching us make out, and when I catch his eye sometimes he smiles and sometimes he looks playfully hurt. When his brother walks off to go to the bathroom or to get cash from the ATM for John’s tip jar, John grabs my leg under the bar. I suppose still wanting to stake some claim. I was here first. I really don’t mind.
Both of the boys enjoy dancing and I enjoy watching them. John goes off to take the mini-stage with some of the other bartenders who have now connected a mic to the speaker system and are singing along to music that vacillates between abrasive metal and 90s hip hop. John’s brother stays with me at his seat and dances with his muscular little arms over his head like a go-go boy. It’s absolutely adorable.
While his brother is off peeing or something, I turn to John and ask how he’s doing. He starts talking about the night of New Year’s.
“You know, just because I didn’t make out with you doesn’t mean I didn’t want to,” he says. I know this already but it’s satisfying to hear him say it. I ask how things are going with his girlfriend.
“I’m trying to get her into other girls,” he says. I try to school him that this is not the direct path to what he wants.
“You need to be honest with her,” I say.
“I don’t know if monogamy is for me,” he states the obvious. I ask how long they’ve been together. Two years.
“And you already feel this way?” I want to tell him this is not something that’s going to get better with time.
I tell him, “John, this is my jam. I will be here for you as a friend.” I might be a little drunk.
But then he says, “But I wouldn’t want her to do the same thing.” Wait, what?
“So, you want freedom in the relationship but you don’t want her to have the same?”
“Well then, go fuck yourself.” I pat his back. I’ve encountered this before. Men who want to fuck around but can’t deal with the idea of their partner doing the same. The obvious hypocrisy and need for control is infuriating. How do they expect their women to be open-minded about this if they refuse to be?
I return to his brother. We keep making out and now I’m feeling on his crotch. He is very hard in his jeans. He cups my ass and puts his hand up my shirt. I lift my bra so he can slip beneath it. I take his finger in my mouth and suck on it—this is apparently too much for him and he holds me back, which only makes me want to do it more. He suggests we leave and go back to my place. Why not John’s? I want to say this as a joke but think better of it.
For some reason I’m not sure I want to take him home. I’m enjoying the dynamic of making out at the bar with John watching and I’m thinking about the uphill walk to my house. And then there’s the fact that I’m trying to cool it on the one night stands. But he’s leaving on Monday and if I want to have sex, this is probably my only chance. I’m on the fence, trying to decide what I want. I’m not sure why what comes out of my mouth is, “I’m not sure if we should have sex. I actually like you.” He looks confused.
“I mean, I don’t know you that well but I’ve enjoyed our time together,” he says, diplomatically. Then he turns away to talk to another bartender and I think I’ve blown it. Why did I say that? I guess what I meant to say was, “I’m trying not to have sex with strange men because my female body and brain sometimes create attachment feelings that take a lot of energy for me to deal with.” Or, "If I have sex now after having not had sex for so long, I feel like the dam will burst and I’ll need it all the time. And you don't live in town and I am currently without a reliable slam piece. If I just keep not having sex, I won’t need it and will be able to stay more focused on the other, more important things in my life. I’ve got shit to do! And the longer I don’t have it, the less I need it. Also, I haven’t been grooming my lady bits really at all lately."
I don’t say any of these things out loud.
“Give me five minutes to decide,” I say. I don’t know what’s wrong with me. He tells me he feels like a creep for pushing it. This is not the turn I wanted the conversation to take. We keep drinking and making out. Eventually, I decide we should probably just follow the natural projection of where this night is going.
“Okay, let’s get out of here.” He heads for the door.
I turn to John and tell him I’m leaving. He makes a face.
“Because it’s time.”
I lean in to hug him and he grabs my face and tongue kisses me. He tastes like his brother. This is my favorite moment of the night. I turn to leave. His brother hasn’t seen the kiss. He is already outside, apparently without saying goodbye to John.
We walk to my house. He takes my hand but this weirdly feels too intimate and we eventually drop it. We walk up the monster hill I live on. Even though he lives in San Francisco, this is still a struggle for him. In my house, I pour us two glasses of ice water and turn on the fan in my room. I head for the bathroom, where I do some quick crotch grooming. Just a little bit. It’s a rush job so fortunately I have the lights set nice and low in my bedroom.
When I return to my room, he has set up the fan so it’s blasting from the foot of the bed. He is in his briefs. They are tight and accentuate the bulge of his crotch. He looks even better with his clothes off. I crawl on top of him and start kissing down his body. I take off my shirt and bra and run my nipples over his chest. I suck on him and he’s got a really nice penis. He doesn’t go down on me and that’s slightly disappointing. Again, as always, I’m tempted to ask why this is, but I don’t want to ruin the mood. He’s pretty good with his fingers. We have sex and it’s fun but I don’t come. Afterwards, I turn off the light and try to go to sleep. It’s five a.m.
At six a.m, the sky is already beginning to lighten and I’m woken from half-sleeping by him groping me from behind. He spoons me and slips it in. Then he rolls me over onto my stomach and finishes like that. I enjoy the spontaneity.
At nine a.m, I’m fully awake. And I have a splitting fucking headache. I get out of bed, put on my PJs, and head to the bathroom where I take two Advil. My mouth tastes like garbage so I brush my teeth and wash my face and remove my eye makeup. It’s rare that I don’t do this before bed, but I haven’t had that much to drink in awhile. I pound some water and return to bed where he has put on his briefs and is chewing gum and looking at his phone. I crawl in next to him and put my arm across his chest. He moves in closer to me. We start making out again. He lifts my shirt and sucks on my breasts. My PJ pants come off and he crawls on top of me. This time I do come. He’s really good at grinding on top of me in just the right way. He doesn’t do the jackrabbit pounding preferred by so many porn-raised dudes of 2015. The orgasm magically disappears my headache.
Afterwards, I ask if he wants any tea or coffee. He asks what kind of tea I have. I tell him about my hippie selection.
“I’ll take coffee,” he says. I put on my PJs again and head for the kitchen.
I ask if he wants a piece of toast.
“No, thanks. But that’s nice,” he says. I know I’m breaking one night stand etiquette by offering to feed him. It’s an uncomfortable negotiation for everybody.
I return with the coffee and he scoots off the bed so as not to spill any on my sheets. He stands and peruses my walls. He asks about a painting of a woman’s naked body from behind.
“There’s a lot of naked people up here,” he says.
“I’m kind of obsessed with nudity,” I explain.
“I’m kind of obsessed with nudity,” I explain.
He asks about a calendar I have of three naked women in different shots doing various tasks backstage of a theatre. I explain that this calendar was a fundraiser I did for a theatre I’m involved with. I point myself out, topless and wearing a giant blond Afro wig. He tells me he too posed for a calendar, for one of his clients who is a drag queen. He takes out his phone and shows me the picture. He is dressed as Santa with his shirt open and is flocked by four drag queens dressed as the Golden Girls. One of them (presumably Blanche) is perched on his lap. He wins so many points with me in this moment.
“You were born to do this,” I tell him.
We finish our coffee and he gets dressed. He goes to the bathroom and I change into shorts and put on a bra under my T-shirt. We walk together down my hill, heading to retrieve my car. As we pass the bar from last night, a guy is opening the door and John’s brother knows him. He crosses the street and gives him a big hug. The guy takes us inside where there is glass all over the sticky floor. And a mirror over one of the booths is shattered. This guy is tasked with cleaning up the mess. We laugh at the wreckage and continue on our way.
I offer to drive him home (to John’s house).
“John’s going to be pissed at you for showing me where he lives,” I joke as I round a corner.
“Are you going to stalk him now? Don’t get weird,” he says, teasing me.
“Last night I thought I was going to roll in, have one drink at the bar, and head home. I had no intention of staying until 5 a.m. and then taking home John’s brother.” I laugh. He does too.
I pull up in front of John’s house and he gives me his number for when I’m next up in the Bay Area. We kiss goodbye and I drive off.
It is not lost on me the fact that I began this night lusting after one unattainable man, only to move on to another unattainable man, only to finally settle on an attainable man whom I wasn’t sure I wanted to sleep with. Why was I unsure about this third man? Because it was too easy I didn’t have to fight for it? Friends of mine have told me that I enjoy the chase, that I like the challenge of an unavailable man. But do I really? That’s not at all what I think I want. But then why is it so tempting for me to try to lure said man out of whatever current situation has him lusting after me and unable to do anything about it?
The last memorably good sex I had was with Burly Man in the elevator—because we both wanted it so badly and we knew we shouldn’t have it (again, his girlfriend), which only made us want it more until the tension built up to such a boiling point that when we finally did fuck, it was explosive. That is what I want—that level of passion and spontaneity that feels undeniable. I want my rational mind to be too overcome to get involved. I want to feel out of control. And what tends to come with that feeling of late is unattainable men in relationships.
When I ask John why he’s still with his girlfriend, he says, “She’s the best person.” Not, I’m so in love with her, or she’s my best friend. But, “She’s the best person.” Burly Man gave me a similar response when I asked about his relationship. And to me this sounds like each of these guys has put their respective woman on a pedestal where they can view her from below as this perfect being. And, not to take this analogy too far, but in this scenario, if she’s the Madonna, I’m definitely the Whore. I guess this justifies why John doesn’t want his girlfriend fucking other guys—if he sees her as this Madonna figure, the idea of her sleeping with other men would spoil her for him.
“I’m not a Madonna and I’m not a Whore. I’m your wife and I’m sexual and I love you.” Forgive me as I quote Sex and the City. When I went to look up the exact wording of this quote, I found that my memory of it was word perfect—either I have watched way too much Sex and the City or this phrase stuck in my mind for some reason. Probably it’s both. Charlotte says this to Trey as she’s trying to get him to have sex with her (he’s having trouble performing in bed, but likes to yank it to Playboy in the bathroom). This is an old story. In Masters of Sex, Bill Masters sees his wife as this perfect woman and the mother of his children—and he can’t bring himself to have sex with her. Meanwhile, he sleeps with flirtatious, sexually-liberated Virginia Johnson at every available opportunity. There’s always a sense in these illicit affairs that once it stops being illicit, the mistress becomes the wife and inevitably the free, spontaneous sex stops and “real life” begins. In this scenario, it is definitely more fun to be the woman outside the relationship tempting the man away from his quaint home life. But even as I’m playing the role of the Other Woman, I can relate to the wife/girlfriend back at home. I can see myself in her shoes and I wonder what’s her story, what are her fantasies? And I hope that she’s having some fun, that she’s taking care of her own needs. And my hope for myself is that when I am on the other side of this equation, I will be with someone who sees me not as a Madonna or a Whore, but as a multi-faceted person who has qualities of both these archetypes, and more.