Chapter 31
RYAN
Who was the genius who installed fluorescent lights in the hallway?
The unforgiving glow illuminates every wrinkle, grass smudge, and—most critically—the dark, unmistakable patch of cum spread across the front of my shorts.
I’d almost convinced myself it had dried enough to be invisible, or at least ambiguous. That I could pass it off as spilled sparkling water.
The hallway light disagrees.
I fumble with my key, hands still trembling from the evening’s events—from Oliver’s weight on top of me, his breath against my ear, the way my entire body had unraveled beneath him in ways I didn’t know were possible.
My fingers are clumsy, operating on a two-second delay, and the key scrapes against the lock plate twice before finding the slot.
The door swings open, and Jackson Monroe is sitting cross-legged on his bed in basketball shorts and a faded BSU Athletics shirt, a mystery novel open on his lap and a bag of trail mix balanced on his knee.
His brand-new reading glasses—the ones he refuses to wear in public because he thinks they make him look like a “nerdy quarterback,” which is exactly what he is—are perched on his nose.
“Hey!” His face lights up the way it always does when I come home, as though my return is an event worth celebrating.
“How was the picnic? Did you guys see cool stars? Did Oliver try to name a constellation after you? Because Gerard texted me saying Oliver was going to try to name a constellation after you, and I told him that’s not how astronomy works, but—”
He stops.
His eyes drop.
The trail mix bag crinkles as his hand goes still inside it.
I brace for impact. The teasing. The howling laughter. The inevitable group text to Drew and Gerard that will ensure I never live this down for as long as I draw breath.
Instead, Jackson’s face does something I don’t expect.
He smiles. Not the mischievous, I’m-about-to-roast-you grin I’ve come to know over three years of cohabitation. A real smile. Warm and genuine and almost proud, the kind a parent might wear at a graduation ceremony.
“Ryan,” he says softly. “Did you have a good time tonight?”
My face is on fire. I can feel the heat radiating from my cheeks, to my ears, to the back of my neck. I’m standing in the doorway of my dorm room, wearing the physical evidence of my first sexual experience on my pants, and my roommate is looking at me with the tenderness of a golden retriever.
“I—yes. It was. The picnic was—yes.”
“Good.” Jackson nods, his smile widening. “That’s really good, Ryan. I’m happy for you.”
“You’re not going to make fun of me?”
“Why would I make fun of you?”
I gesture at my shorts with both hands, the universal signal for look at the catastrophe happening in my crotch region.
Jackson waves a dismissive hand. “Dude. That’s nothing. That’s a badge of honor. You went out there, you had an experience, and you came home with proof.” He pauses. “Phrasing aside.”
“Jackson, I can’t walk to the laundry room looking like this. If anyone sees me—the RA, another student, a janitor with functioning eyes—”
“Give them to me.”
I blink. “What?”
Jackson swings his legs off the bed, setting aside his book and trail mix. “Give me your shorts. And whatever else needs washing. I’ll take them down.”
“You don’t have to—”
“Ryan.” He holds up a hand. “If anyone sees me carrying stained shorts to the laundry room, they’ll think, ‘Oh, there goes Jackson Monroe, that rascal, probably had a great Tuesday with his boyfriend hockey player.’ My reputation can absorb the hit.
Yours can’t. Not because there’s anything wrong with what happened, but because I know you.
You’ll catastrophize it for three days.”
God, I hate that he’s right. I would spiral.
I would construct an elaborate internal narrative in which every person who stayed in our building this summer knows exactly what happened and is silently judging me.
And I’d carry that narrative with me until it calcified into a permanent source of shame.
“You’d really do that?” I ask.
“Brother, I’d tell people I had such a good time with Drew that I ruined two pairs.” He grabs his laundry bag from its hook behind the door. “Now strip. In the non-sexy way.”
I retreat to my side of the room and turn my back, peeling off the khakis the way one handles hazardous materials.
My briefs follow. I fold both items with military precision because some habits are branded into your DNA when your father is Colonel David Abrams, and hand them to Jackson without making eye contact.
“Shirt too?” he asks.
I glance down. There’s a grass stain on the collar and another on the hem. “Please.”
The button-down joins the pile. Jackson stuffs everything into his laundry bag alongside a few of his own items—strategic camouflage, I realize—and slings it over his shoulder.
“Back in twenty. Don’t go anywhere.” Jackson winks and disappears into the hallway, the door clicking shut behind him.
I stand in the middle of the room, naked except for my socks, and process what just happened.
I pull on a clean pair of briefs and a T-shirt from my dresser, then sit on the edge of my bed.
My hands are shaking again. Not from cold or fear, but from the aftershocks of a seismic shift in my understanding of myself.
I had an orgasm with another person tonight. With Oliver. And it was transcendent.
And now I want more.
The door opens seventeen minutes later, and Jackson returns, laundry bag notably lighter. He kicks off his shoes and settles back onto his bed, resuming his cross-legged position, having not a care in the world.
“Machines are running. Your shorts will live to fight another day.” He reaches for his trail mix, pops a cashew into his mouth, and studies me. “You’ve got the face.”
“What face?”
“The ‘I have a question, but I’d rather swallow my own tongue than ask it’ face. I’ve seen it approximately four hundred times since we became roommates.”
I pull my knees to my chest and wrap my arms around them.
The dorm room feels very small and very quiet.
Jackson’s side of the room is its usual disaster—shirts draped over his desk chair, protein bar wrappers forming a small mountain near his wastebasket, a movie poster—Sixteen Candles—with Molly Ringwald watching over us with a benevolent gaze.
My side is immaculate by comparison: books alphabetized, telescope positioned by the window, Mom’s star chart pinned above my headboard.
“I have a question,” I say.
“Shocking. Hit me.”
“It’s about sex.”
Jackson doesn’t flinch. Doesn’t laugh. Doesn’t even pause his chewing. He just nods, gives me his full attention, and waits.
“When Oliver and I…when we do more than what we did tonight…” I trail off, my courage evaporating in real time.
“Take your time,” Jackson says.
I stare at the constellation chart on my wall. Orion stares back, offering no guidance on this particular matter. “Will it hurt?”
Jackson sets down his trail mix. “You mean penetration.”
“Yes.”
Jackson exhales through his nose, leans back against the wall, and crosses his arms. His expression shifts into something contemplative—a look I’ve only seen him wear during film study sessions, when he’s breaking down an opponent’s defensive scheme.
“Okay,” he says. “I’m going to tell you something I haven’t told a lot of people. And I need you to understand that I’m telling you because you’re my best friend, and you deserve honesty, not because I want this getting back to anyone.”
“I would never.”
“I know you wouldn’t. That’s why I’m telling you.” He adjusts his glasses, pushing them higher on his nose. “The first time I got fucked was with Drew.”
My eyes widen. Obviously, I figured as such, but hearing him state it so plainly, so directly, still catches me off guard.
“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 say it 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. ”
“Jackson—”
“Nope. No deflecting. No British-boarding-school modesty. You walked in here with cum on your shorts, and I laundered them for you without judgment. You owe me the full story.” He settles back against the wall, folds his arms behind his head, and assumes the posture of someone preparing for a feature-length film.
“I want the picnic. I want the sunset. I want the moment things escalated. And I especially want to know what Oliver did that made you ruin a perfectly good pair of khakis. Make my toes curl, ol’ buddy, ol’ pal. ”
My face is incinerating. Every instinct I have is screaming at me to deflect, to minimize, to fold the evening into something small and manageable.
But Jackson did tell me about Drew. About fingers and lube, of trembling thighs and trust. He opened a door for me, and the least I can do is walk through one for him.
“Fine,” I say.
Jackson pumps his fist. “Yes. Okay. Go.”