“I wanted more. I wanted to know what it felt like to have someone inside me.” He pauses, his cheeks coloring slightly. “Remember when we all did that body paint thing for charity? When we got home, I asked Drew to fuck me.”
“How did he respond?”
“He said yes. Obviously. Drew’s not the type to turn down a request for his services.” A fond smirk crosses Jackson’s face. “But he also took it seriously. Way more seriously than I expected.”
I’m leaning forward without realizing it, absorbing every word. “So did it hurt?” I press.
Jackson tilts his head, considering. “Honestly? Yeah. At first.”
My stomach drops.
“But,” he adds quickly, holding up a finger, “not in the way you’re imagining. It’s not sharp pain. It’s not injury pain. It’s more like your body adjusting to something it’s never experienced before. Like stretching a muscle you didn’t know you had.”
“That doesn’t sound pleasant.”
“It’s not, for the first minute or two. And that’s where the other person matters.” Jackson’s voice softens. “Drew was incredible. He went slow. Painfully slow, actually. He used enough lube to fill a swimming pool. He checked in constantly.”
“And then?”
“And then my body relaxed. The discomfort faded, and what replaced it was—” Jackson pauses, searching for the right word. His eyes drift toward the ceiling, and I watch the memory play across his face. “It was fullness.”
“Drew’s not exactly small,” I say, remembering what I’d seen that night in the pool at the beginning of the summer.
Jackson barks a laugh. “No. No, he is not. Which is why the prep matters so much.”
I file this information away, as if I’m studying for an exam. Prep. Lube. Communication. Patience. “And when he actually?—”
“When he pushed in?” Jackson nods slowly. “That was the moment. The stretch was intense. My whole body tensed up, and Drew just held still. He was shaking—I could feel his thighs trembling against mine—but he didn’t move an inch until I gave him the green light.”
“How long did that take?”
“Maybe thirty seconds? Felt longer. But once I adjusted and told him to move—” Jackson’s eyes go distant, and a smile tugs at the corner of his mouth. “Ryan, I’m not exaggerating when I sayit was the best physical sensation I’ve ever experienced. And I’ve scored a game-winning touchdown in overtime.”
“You jocks and your sports comparisons.”
“It’s the only frame of reference I have for peak human experience. Sue me.” He grabs another handful of trail mix. “The point is, yes, there’s discomfort at the start. But with the right person—someone who gives a damn about your experience, someone who’s patient and attentive—the discomfort is temporary. What comes after is worth every second of it.”
I absorb this, turning it over in my mind. The fear doesn’t vanish entirely—I don’t think it can, not until I’m actually in the moment—but it shrinks. It becomes manageable. Knowable.
“Drew also told me something afterward that stuck with me,” Jackson adds. “He said the most important thing isn’t technique or position or any of the stuff you read about online. It’s trust. If you trust the person you’re with, your body follows. It lets go.”
Trust. The word resonates in my chest, vibrating against the memory of Oliver’s voice in the dark.I’ve got you. I’ve always got you.
“I trust Oliver,” I say. It comes out steady. Certain.
“I know you do.” Jackson’s smile is back, warm and uncomplicated. “And Oliver’s going to take care of you. You said it yourself—that man stress-cleaned his entire house before taking you stargazing. He’s not going to half-ass the most important night of your life.”
A laugh escapes me, unexpected and genuine. “Thank you, Jackson. For telling me all of that. I know it wasn’t easy to share.”
“Are you kidding? I’ve been dying to talk about Drew’s dick game for months. You just gave me a legitimate excuse.” He tosses a raisin into the air and catches it in his mouth. “Besides, that’s what best friends are for. The uncomfortable conversations that nobody else will have with you.”
I unfurl from my protective ball, stretching my legs out on the bed. The tension that had coiled in my shoulders since I walked through the door is loosening. The room feels warmer. Safer.
“Now.” Jackson claps his hands together once, the sound sharp enough to make me jump. His eyes are gleaming behind those reading glasses, and his entire body has shifted forward on the bed, trail mix forgotten. “I’ve shared my deeply personal sexual history with you in the spirit of friendship and education. I believe that entitles me to something in return.”
“What?”
“The dirty deets, Ryan.” Jackson’s grin stretches wide enough to threaten the structural integrity of his face. “Every. Single. One. What happened in that park tonight? Start from the beginning, leave nothing out, and if you skip the good parts, I will know, because I am fluent in the language of your facial expressions and I can tell when you’re editing.”
