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Welcome to Playboy Undercover—where our anonymous columnists give you a peek of what’s really going on, well, under the covers. From the curious to the downright kinky, our guides are pulling back the curtains on desire. Wanna invite us undercover? So long as it’s between two (or more!) consenting adults, we’re game. Send your story to [email protected].
On my first date with the beautiful boy who helped me get out of my marriage, I fed him breastmilk. “You did a good job,” I said, “get on your knees.” I pointed to the floor next to the bed. He held my gaze while he knelt silently. I reached up my shirt, squeezed milk into my hand, and offered it to him. He sucked it off my palm like he was about to die of thirst. I wiped what was left across his huge mouth. I wanted to leave him there on his knees and walk out, but I couldn’t. It was the first of many times I wouldn’t manage to leave him when I should have.
I was, at the time, obsessing about whether I was gay. Trying to figure out how to tell my husband. Trying to figure out how to leave my husband. Emotionally and logistically. We had a six-month old baby girl.
I was wondering if I was gay or just wanted to be so that I could feel less guilty about wanting to leave—so that I could leave because I needed to, not because I wanted to. Some days, I was sure I was gay and needed to leave. There was no question that dating women felt better. Some days, I was sure it was just an intrusive thought I could get rid of. Some days, I was sure that leaving him would shatter me.
Some days, I thought I had a great deal, seeing women on the side with a loving husband at home. He took such tender care of me. Giant, loving eyes and unending sweetness. A perfect little family square: mom, dad, dog, baby. I could give her all of that if I could stay and make it work.
Other days, I hated him. I hated the appointment making and meal planning. The diaper-buying and bill-paying and dishes. His inability to take on any of it. He always apologized and never changed. I hated his passivity. Then I would think that I’d never find a man both sweet and functional, so I better be really fucking gay.
He was waiting tables inside but he kept coming outside and staring at me. I was annoyed. It was a rare night away from the baby and I wanted to read my book and drink my wine alone. And I hate art boys. I hate handsome boys. I hate men.
Lalo is 6’ 2” and skinny. Thin but solid. Enormous hands. Enormous feet. Later I’d find out he also has enormous balls. He’s covered in freckles and moles with wavy black hair that parts in the middle and falls down around his pointed eyes. His huge lips are shaped in a permanent pout, the top sticking out further than the bottom. Resting abandonment issues face––even when he’s happy.
His stare was complicit and I started to like it. I found myself smiling back. Still, when he asked for my number, I said no.
Months later, laying next to my sleeping baby, bored and horny, I DMed him. Somehow, within minutes, I was hearing about his traumatic boyhood. Insufferable, I thought. I asked him if he was even 18. He said he was 28 and that his name was Eduardo. I called him Lalo and told him that the apostrophe on his “96’” neck tattoo was on the wrong side. I asked him what he liked. He said spit.
I told him I was married and also gay and would never kiss him or fuck him, but that if he wanted to, he could get naked and read me a story. He said yes and we set a date.
I reached up my shirt, squeezed milk into my hand, and offered it to him. He sucked it off my palm like he was about to die of thirst.
I told him to take a shower, and walked the half hour to his house eating a sticky pastry in the sun. I licked my fingers clean as I approached his building, pleased with myself.
He answered the door clean-shaven in a fresh white undershirt, tailored plaid slacks, and beautiful leather huaraches. He smelled like Winston’s cigarettes and vanilla.
He lived on the side of the highway in a room he rented from an old woman in a dark apartment full of ceiling-high piles of random objects with one shared bathroom and no kitchen.
His bedroom had a creaky wood floor painted red and dimly-colored walls, two violet and two teal. The single curtain on the single window had vegetables embroidered on it. A fluorescent lightbulb dangled from the middle of the ceiling. The apartment upstairs was completely full of dogs that barked in a chorus at random intervals. Their nails clicked against the ceiling.
His bed was tinier than a twin. A monk bed. I think he was longer than it. It had pastel polyester sheets, likely older than both of us, and a pillow that, as I would tell him later when I gifted him a new one, “barely existed.”
The pillow was the first gift. Later, I would buy him a silver bracelet, a silver necklace, an avocado-wood guitar, and a bed.
I stood him up next to the bed, unbuttoned his slacks, and pulled them down with his briefs. He stepped out of them and pushed them aside with his foot. He wasn’t hard or nervous. He seemed impressively calm. I laid back on his bed and said, “Read.”
He read quickly and I said “Slower.”
“Espere que fueras mandona pero no tanto,” he said, annoyed, and did not slow down. I love being read to, but was too fixated on him to pay attention. I had never studied a man’s body, I realized then. Not once.
He stopped to ask if I knew the word “ignominiosa.” I replied, “Yo me sé hablar español,”—a misconjugated way to say “I know how to speak Spanish,” which he repeated back to me whenever I said anything incorrectly for months.
After the story, after I put him on his knees and fed him milk, after I failed to leave, I gestured for him to sit back on the side of the bed. Standing in front of him, I took his huge hand, pulled it under my skirt, and pushed his cupped fingers into me. He started moving them in and out, and I soaked myself. He looked me in the eye, reached his other hand out, and grasped around my neck. It went almost all the way around. I nodded and he squeezed harder. We stared into each other while he fucked me with his huge hand. I wanted to kiss him, but I’d said I wouldn’t.
A few days later, we had sex and I told him he was mine. I’d never said that to anyone. “¿Desde cuando?” he asked. “Desde que naciste,” I told him.
Two days later, he asked me for a necklace with a pendant with the first letter of my name. I got him one and put it in a small jar of breastmilk. I called an Uber moto to bring it to him, but the front door of my apartment building has to be unlocked from the inside, and my sister had left with my key that night, so I couldn’t get out to hand the jar to the driver. I had to ask him to stand under my balcony and catch it. “It’s glass!” I yelled down. “You really have to catch it!”
Not half an hour later, Lalo sent me a video: him, looking into the camera as he drank the whole jar of milk and put on the necklace, still dripping with milk on his chest. “Good boy,” I replied.
He always looked so peaceful when I called him a good boy. It scared me. It felt like I was touching the source code and could fuck up the whole program with one typo.
I was correcting him about something and he interrupted me. “You actually think you know everything!” he said. “I’m thinking of a number! Do you know what that is, too?” Charmed into a stupor, I asked, “Seven?” He widened his eyes and replied, “IT’S FUCK.”
Forever on, whenever I would say “Fuck!” he would say “No, it’s seven.”
He told me how when his mom moved from his pueblo in Oaxaca to the city, she left him behind with his grandma because he was “too bad, too much.” How at 17, he moved in with a friend’s mom, and started getting black-out drunk with her every night. I asked if she ever tried to fuck him. “No,” he said smiling, “but her sister did.”
He told me how he fucked sometimes four women a day––girls from school, his mom’s friends. How he hid under beds from husbands, narrowly escaped fathers running naked from their houses.
He put my clothes back on and refused to fuck me. I was ragingly aroused by this.
He told me how after his fifth bouts of alcohol poisoning, he realized he was going to die, and got sober. How he’d sold everything, and moved to Mexico City with just a guitar. How he’d saved up and recorded an EP. How he’d been feeling peaceful lately.
Laying in bed together, he told me he loved it when I said he was mine because “siempre me he sentido en préstamo.”
Once, we were sitting next to each other reading in silence in a fancy cafe, sharing anchovy toast. He grabbed my face, kissed me, and spit chewed up anchovy into my mouth. I considered screaming and spitting it out, but I swallowed it in silence instead. I looked at him in shock and admiration.
If I’d been out at night without him, he’d get me naked, hold me by the wrists, and meticulously check my whole body for marks before he’d even kiss me. He found bruises once and called me “puta” about six times. He put my clothes back on and refused to fuck me. I was ragingly aroused by this.
One day, short on time, we met up at a cheap love hotel to have sex. After we fucked, I hurriedly stepped into the shower. I don’t remember slipping, only the moment I came to, and saw Lalo’s pale, terrified face. I felt immediate splitting pain in my head, and the room was spinning. I had a concussion. He had to go to work but didn’t want to leave me. I sent him off insistently. Then the hotel room phone rang. It was the front desk calling to make sure I’d been paid before they let him out. I laughed and the laughter hurt my head.
Once, while we grocery shopped, Lalo was telling me a story in which two of his cousins get caught fucking, which was not the main plot. “Your cousins were fucking?!” I asked. “Así es en Oaxaca, Nena,” he answered casually, “I’ve fucked all of my cousins.” When I looked at him shocked, he added, smiling, “only the ones that are older than me.” I pretended to be horrified but I masturbated about it for months.
I took my cousin’s ex-wife to eat where he worked. She’s in her mid 50s, successful, beautiful, and rich. I want to be like her when I grow up.
At some point during the meal, she leaned forward and said, “I don’t know if this is totally inappropriate to say, but our waiter is extremely hot.” I agreed.
She told me that she’d left my cousin because he was not helpful. The labor was uneven. She said she had not remarried on purpose.
I wanted so much to tell her that I wanted to leave my husband for the same reason. But if I said it out loud, it would become too real.
One day, without having fully decided to, I broke up with my husband. I told him I had to leave because I was gay. And because I was mad at him. After seven years of marriage, I gave him four months to move out. He was utterly shattered and all I could think about was how desperately I wanted him not to be mad at me.
During the months before my husband moved out, I sublet a big sunfilled apartment and started leaving my house every other day to stay in it. I let Lalo live there and I called it the sex office.
In the sex office, I hid from my own grief, from my husband’s devastation, from my beautiful but endlessly needy baby.
It was wonderfully quiet.
In the sex office, Lalo cooked for me—excellently. Food from the isthmus that his grandmother taught him to make. Meat stews seasoned with cinnamon, ginger, and avocado leaves. Food that smelled like nourishment. I had never been fed like that.
Once, during an argument, he said, “When I get mad at you and then you get mad at me back because you want me to make you feel better, that’s manipulation.” I’d been doing it to people forever, and also arguing like admission of wrong would mean death. Lalo would ask, “don’t you find that exhausting, princesa? Needing to be right that badly?” I did and it wasn’t funny. This time, I just said, “I’m sorry,” and then cried with relief on his chest.
He dreamed about our week-long Oaxacan wedding. I held him at bay insisting I could never be monogamous, reminding him I was just now getting divorced.
But the divorce was an excuse. I did not want to marry another broke artist. Not with a baby. Not without one. No fucking way.
He hated that I was always staring at women. On my birthday, I kissed a girl on the dance floor and he was crushed. We didn’t have sex for a week. When we did, I said, “Tell me I can’t kiss other girls,” in the middle of it and he stopped immediately. Looking wounded, he said, “This is not a game to me, you fucking bitch.” I fucking loved it. It’s all I’ve wanted anyone to call me since.
I still get wet at the sound of a belt buckle jingling.
I started goading him to fuck other girls—something he expressed often that he had no interest in doing. I wanted to beg him not to, wanted him to do it anyway.
He texted me while I was out of town that he was on his way to some gringa’s house. A redhead with a big ass who gave him her number at the restaurant. “You asked for this, and now you’re going to deal with it,” he texted, then described everything he planned to do to her while I begged him not to until I came.
I told him how much I loved him and thanked him for being my “complice en juegos torcidos.” He replied:
“Sueles ser muy abierta y expuesta después de que tenemos una fuerte interacción sexual. Solo te pido que sigas teniendo cuidado. Porque un día puse mi corazón en tus manos.”
Once, I told him a story about tattling on my sister for hitting me. My mom said, “Hit her back!” and I said, “No mommy! Hitting is wrong!” He laughed hard and repeated that line back to me for days.
Weeks later, one night after going out, I’d picked him up from work late and drunk. When we got home, he bent me over the kitchen counter, pulled my pants down, and took his belt off. He folded it in half and then quarters and said, “Te tengo un par de preguntas.” Then, while barking questions about who I’d been with and why I hadn’t answered the phone, he whipped my ass until I had massive blue bruises and red welts. The next day, I sent him pictures with the caption, “hitting is wrong.” I still get wet at the sound of a belt buckle jingling.
I couldn’t even look at him when I said it: “I want to have like… normal sex.” I had never wanted that. He ran his hands softly along my arms and legs and I felt him everywhere. He kissed me and that would have been enough, but when he penetrated me gently, it felt like he’d ripped my ribs apart and entered my entire body.
Friends came to visit from New York. We all went to a nautical themed karaoke bar, and Lalo sang me Almohada by José José. I sat on his lap and got yelling drunk. We stayed til close, dancing salsa both in cowboy boots, as the staff placed chairs upside down on tables around us. We all ate oysters in a fancy hotel bar at 2am. While Lalo and I had sex that night, he refused to kiss me, as a game. When he did, I came.
I came home from New York with bruises up and down my thighs, and Lalo broke up with me on the spot. I was in shock. I’d never been broken up with.
I couldn’t believe he didn’t want to have breakup sex. Walking away from sex like that makes no sense to me. He said it would be too painful. He said, “I’m not a masochist like you are.” But I was just learning to enjoy “normal” sex––without the pain.
I begged him to come back for two months straight, sending pictures of my swollen eyes, promising monogamy. I knew I did not want to be with him and I persisted anyway, begging him to alleviate my pain.
He thought it best we didn’t see each other for a few months. Then, one day when we both had colds, I suggested we go get chicken soup. It was so easy to be with him again. His smell made my heart race. His hand on my back made me wet. I begged him to fuck me, begged him to come back. He said OK.
He immediately saw the panic in my eyes. His eyes got huge, incredulous. “You have to be fucking kidding me,” he said. “You BEGGED ME FOR MONTHS,” he said. I knew it was the worst possible thing to do, but I collapsed into reassurances anyway. So then we were novios.
We were novios for three months, only now it was real life. Me, living in my apartment alone, with a baby half the time. Him, working at a new restaurant a few blocks away. I could not stand him lounging on my couch, eating my food out of the containers with his hands while I worked in the mornings before his shifts. I hated his stinky shoes and how he left wet towels on the bed. So I said he could not stay over on weeknights. I said, “We’re novios, we’re not married. This is my life and you have yours.” He did not like this new arrangement. I said, Fine, go. He did not. But he stopped cooking for me.
One day, after putting my baby down for a nap, I came out, walked to the couch where he was sitting, and told him we had to break up. He asked why, and, nauseous at my own cowardice, I said “because I’m gay.” He stood up silently, went to the balcony, and lit a cigarette.
“I was just a vehicle to get you where you needed to go,” he said flatly, his voice breaking, eyes full of rage and tears. I was on my knees apologizing on a loop, sobbing, telling him it wasn’t true. We both knew it was, but I didn’t want him to know. I begged him to hug me.
“You have to learn to let people not like you,” he said.
Before he walked out, he hugged me tightly one last time, and said “por favor, no me busques.” Not a word from him since.
I hope he knows I loved him.