I Asked my Boyfriend to Hook Up With A Man

Pressed Against the Wall—and My Own Desires

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I never imagined I would be asking my boyfriend for permission to fuck another man, but there I was, pressed against the brick of a sun-warmed wall, making out with Aaron, a drummer I’d met a few weeks earlier, and fucking him was exactly what I wanted to do.

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“God, I wish I could have you…” I moaned into Aaron’s neck as I moved my hips forward to better feel his cock against my belly.

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It was a beautiful, luxuriously thick cock I hadn’t gotten to experience yet fully. On our last date, hiding in the shadows of a darkened street, I wrapped my hand around it and felt it pulse.

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But that was as far as I’d gotten.

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It was earlier tonight, the late-night summer sunset was still splashing the sky with brilliant pink and purple, and people were milling past. I didn’t dare go so far tonight.

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I prayed for a place to magically appear so we could get naked, so I could feel what it was like to have him inside of me, but he was a couch-surfing musician and I lived with my partner.

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Was this an illicit affair? Not quite.

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Both our partners knew about us, about the desire that couldn’t be satiated by only one person. We had their blessing; we just didn’t have a bed.

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My boyfriend was at home, happy to have a day off, and Aaron’s wife was on a date herself… a thousand miles away in Ohio City, Ohio, where she and Aaron were from. He was here for a gig, and if all went well, they’d both move here.

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“Well…” Aaron said, pulling himself away from me and giving me the cutest look through a curtain of shiny, black hair that fell in front of his eyes. “I might have a place tonight. My buddy said he was thinking of going out… I could check.”

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“Really?! I mean… yeah!”

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But my grin faded quickly as Aaron began typing into his phone. I was pressed up against another wall — this one made of words and promises.

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My partner, Scott, and I had a rule: no sex without checking in beforehand… and considering the circumstances, I hadn’t thought I’d be getting laid that night.

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“Yes!” Aaron exclaimed suddenly, lifting his face, a huge grin on it.“He’s out tonight!” He pulled me in for an enthusiastic kiss. “No pressure, of course…” he added, pulling back and biting his lower lip, still half grinning.

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“Oh, yay!” I said weakly. “It’s just that… well, I told Scott…”Aaron’s arms were looped around my waist, still holding me close, and it was hard to say what I was trying to say.

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“Oh, totally. I get it,” Aaron replied, not making me complete my sentence. “There’ll be other chances to be together.” He kissed my neck, more gently, sweetly, sending tingles to my toes.

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In some ways, even more than the passion, it was his sweetness that killed me.

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“Ok, lemme just— do you mind if I just swing by home real quick?”

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“Sure— but seriously, no pressure.” I giggled as I could still feel the pressure of his cock against the zipper of his stone-washed jeans.

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Twenty minutes later, we were in front of my building.

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“Sure, you don’t mind waiting?” I asked. “There are benches in the courtyard…”

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“Yeah, it’s totally fine. It’s a beautiful night.”

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I kissed him again, stars swirling in front of my eyelids before I tore myself away and ran toward the door. I flew under the cherry tree, which was bursting with ripe, blood-red cherries, through the front door, and up the three flights of stairs to Scott's and my apartment.

The Relationship Check In

I paused outside the door, trying to catch my breath and develop a plan before I wished for the best and opened it.

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“Oh! Hey, babe!” Scott exclaimed. He was lounging on the couch, a glass filled with his homemade iced tea on the coffee table. He must have made a new batch.

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With the dexterity of a circus performer, our cat, DeeDee, leaped from the windowsill, touching down for just a moment onto Scott’s shoulder before she landed on the floor in front of me, rolling to her back and stretching out to greet me.

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“Home so soon?” Scott asked.

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I crouched down to pet DeeDee’s belly and avoided looking at my partner’s trusting face.

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“Yeah. I mean, sorta. Um. Well…”

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“You’re out of breath, Hun. Did you run?”

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Scott stood, stretched, and came to me. He looked so comfy in his boxers and t-shirt. Any other night, I’d have loved to get my own glass of iced tea and join him.

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“You ok?” he asked.

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“Yeah. It’s just… well, Aaron is downstairs. He, um, he has a place to himself tonight, and I…” I glanced up at Scott, who was now standing near me. I could see the moment the knowledge clicked and a slow smile spread across his face.

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“Oh really?” he replied, his tone teasing. “You what exactly?”

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“Well, I kinda thought maybe…”

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Scott offered me his hand, which I took, pulling me to standing so we were face-to-face.

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“Maybe you wanted to go there with Aaron?”Scott asked, looking me straight in the eye.

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“Yeah…” I flashed him what I believed to be my cutest, most charming smile.

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“But don’t we have rules? Weren’t you the one who wanted that one little rule… what was it… about not having sex with someone unless we checked in first?”

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“Well, yes. Yes, I did… and. And… and I’m checking in now?”

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“Is that so?” he asked.

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“Mm-hm…” I had come close to him, squeezing myself into the front of his body, the place I felt smallest, cutest, and sexiest all at once, a combination I achieved with no other lover but him.

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He lifted my chin and kissed me. I welcomed his kiss eagerly. I felt charged with the energy of Aaron’s desire for me, of mine for Aaron, but also by the desire that remained strong for Scott and had become even stronger since we’d opened up.

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I was aware of Aaron waiting in the courtyard under the cherry tree. I didn’t like making people wait, and yet, right now… it felt kind of good, the way Scott put his lips to my ear and whispered:

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“I want to have you first.”

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“Okay,” I whispered back.

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He took my hand and led me into our bedroom. I unbuckled my shorts and pulled them and my panties down in one fell swoop before I got onto the bed.

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Scott was already hard as he came to me, kissing me and then grabbing my hips and turning me to my hands and knees.

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He got behind me and reached around to pussy. I moaned in pleasure at his eager fingers.

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“Already wet I see,” he murmured.

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I felt oddly embarrassed but turned on at the same time. I was being so naughty, and my boyfriend knew it. Moreover, he was okay with it.

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Scott put the head of his cock against my opening, and my hips lifted to meet him, my back arching, yearning…

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When he slid inside of me, I cried out in pleasure.

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We were so familiar with each other’s bodies that Scott found the exact angle to begin massaging my G-spot right away. I began riding him, thrusting my hips back again and again as I felt myself already right on the edge.

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Scott moaned, feeling me tighten around his member. Our breath grew louder, together, as the pleasure built.

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Normally, I liked to linger on the edge, but that night, I came quickly.

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A few moments later, Scott pulled out and came, splashing hot cum on my ass.

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After a few moments, he kissed me. “Now you may go, my love,” he whispered. “Go fuck your hot, new drummer boy.”

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I laughed, feeling giddy. “Thank you. You’re too kind.”

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The Moment I Slipped Into the Role of a Woman Having Sex With Another Man

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I cleaned up quickly, kissed Scott one more time, shouted goodbye to DeeDee, and was back out the door, greeting Aaron under the cherry tree.

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“Wow, these are great cherries!” he exclaimed, popping one into his mouth. “I had no idea they grew around here.”

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“I know, aren’t they good?” I plucked one and put it in my mouth, feeling the smooth skin and anticipation of more sweetness to come.