E18: Let Me Ease You Into It | My Ex’s Brother Drew

This fictional story features only adult characters (18+) and portrays consensual interactions throughout.

Recap: Drew said he wanted to try bottoming for me. I kissed him, thinking he was half-joking. But then he got up, stripped off his clothes while walking to the bedroom, and climbed onto the bed like he knew what he was doing. We laughed, we teased and then I spread him open and started licking his hole. The sounds he made? The way he gripped the sheets? He was hooked. And now I’m lubing up my fingers, about to stretch him for the first time.

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Drew lay on his stomach, one arm curled under the pillow, the other bent above his head. His back muscles twitched every time I touched him. His cock was hard, pressed into the sheets, and his ass-arched perfectly with a pillow tucked underneath was already glistening from my spit.

I sat back on my knees and poured lube into my hand, rubbing my fingers together slowly.

He turned his head a little, voice muffled against the pillow. “So, like… what do I do?”

I smiled. “Just breathe.”

“I am breathing.”

“Not like that.”

I leaned forward, kissed his lower back. “Let me ease you into it.”

“Okay.” He sounded unsure. But not unwilling.

I placed one hand on his lower back, just grounding him, then used the other to circle his hole with one lubed up finger. No pressure yet; just touch.

He shifted, barely. His legs parted slightly wider on their own.

“Still good?” I asked.

He grunted. “Yeah. I think.”

I pushed just the tip in. Slowly. Gently. His whole body stilled, then tensed.

“Shit,” he muttered.

“Breathe, Drew. Breathe.”

“Yeah....uh...Yeah.”

I stayed there, letting him adjust. My free hand stroked slow lines up and down his spine. When he finally exhaled fully, I slid in a little deeper.

His hole clenched around my finger like it didn’t want to let go.

“Holy fuck,” he said into the pillow. “That’s… a lot.”

I chuckled softly. “You’ve fucked me without prepping my hole, like, how many times? Now you know.”

He groaned. “You made it look easy.”

“It’s not. But it’s worth it.”

He didn’t say anything for a minute, just lay there breathing. I moved my finger gently, letting him feel it, curling slightly. His hips shifted towards my finger.

When I slid in a second finger beside the first, he let out a surprised noise. Not pain. Not pleasure. Just raw sensation.

“Oh fuck.”

“Too much?”

“No, no. Just--feels insane.”

I kept it slow. Steady. Curling, scissoring. Watching how his body responded. There was something almost surreal about it. This man; this cocky, ripped gym owner who’d been railing me like a machine...was now face down, letting me open him up. And he was hard. Dripping. Loving it.
The video from earlier flashed back in my head. Jason...bent over, taking it from two sides, moaning like he needed it. I hadn’t been able to look away. Seeing him like that did something to me.

Not just because he was getting fucked. But because for the first time, the power had shifted. He wasn’t the top. Wasn’t in control. And fuck… it turned me on.

“Drew,” I murmured, voice low. “You’re doing so good.”

He gave a half-laugh. “Don’t make it weird.”

I smiled. “I’m serious.”

He turned his head toward me again. His expression was soft. A little flushed. Curious.

I added a third finger.

His hips jolted.

“Fuck,” he whispered. “Okay, that I felt.”

“Too much?”

“No, no.. keep going.”

I paused, letting him adjust again, then began slowly working all three fingers in and out. His body shuddered. His legs pressed into the mattress. His cock left a slick patch against the sheets.

“You’re opening up so well,” I said, almost to myself.

He groaned again. “I don’t know how you do this all the time.”

“It gets easier,” I whispered, twisting my fingers gently. “It gets better.”

“I’m gonna lose my fucking mind,” he muttered.

I kissed his lower back. “Good.”

We stayed like that for a few more minutes...him face-down, moaning softly, and me easing him open one stroke at a time.

When I finally pulled out, his hole clenched after me, twitching around nothing. His cock was still rock hard, leaking against the sheets.

I kissed the back of his thigh and whispered, “You ready for my cock now?”

He turned his head again, lips parted. “Yeah. I think I am.”


I reached for the lube again, drizzling a slow line down the crack of his ass . It slid over his rim, catching in the slick he'd already soaked up. I stroked myself with one hand, thick and aching and drizzled lot of lube over my cock and rubbed it. My other hand was rested on his lower back, steadying both of us.

“You sure?” I murmured, leaning over him.

He nodded once, cheek still pressed to the pillow. “I want to feel it.”

I lined myself up, nudged the head of my cock right against him, and paused. His body tensed just slightly.

“I’ll go slow,” I said. “Just breathe.”

“I am breathing,” he shot back...gruff, almost annoyed but I could hear the nerves beneath it.

I laughed quietly under my breath. “Right.”

I pushed my cock in.

Just the tip. Just enough to feel that first tight resistance around the head of my cock. Drew grunted low, his hips shifting once but not pulling away. I rubbed his back in slow, calming circles and waited.

“You okay?”

“…Yeah,” he said after a beat. “Keep going.”

So I did. Inch by inch. His hole stretched around me, clenching tight, hot and brand-new. My cock pulsed as I sank deeper, the grip of him unreal. By the time I bottomed out, he let out a shaky breath that sounded part pain, part disbelief, part fuck yes.

He buried his face in the pillow again. “You weren’t lying. You’re not that big… but fuck.”

I laughed under my breath and gave his ass a light slap. “Wow. Rude.”

Before he could say anything smart, I pulled back and slammed in a little harder.

His whole body jolted. “Uh-oo-ahh--fuckkkk-”

I grinned, staying deep. “Still think I’ve got a small dick?”

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