My First Time Bottoming

I'd been out for three years and had fooled around with enough guys to know I was definitely, unquestionably gay. But despite all of that, I'd never bottomed. Not once.

It wasn't that I didn't want to. The curiosity had been building for years—watching porn, reading stories, imagining what it would feel like. But there was always something holding me back. Fear of pain. Fear of vulnerability. Fear of not being good at it, whatever that meant.

Then I met Noah.

We'd been dating for two months when the conversation finally came up. We were lying in his bed after another round of everything-but, both of us satisfied but me still wondering what I was missing.

"Can I ask you something?" Noah said, tracing lazy patterns on my chest.

"Always."

"Have you ever bottomed?"

My face heated. "No."

He propped himself up on one elbow to look at me, no judgment in his warm brown eyes. "Is that something you want?"

"I think so. I've thought about it a lot. I just..." I trailed off, not sure how to articulate the tangle of desire and fear.

"You're nervous," he finished. It wasn't a question.

"Yeah."

He leaned down and kissed me softly. "That's completely normal. It's a big thing, especially the first time. But Alex..." He waited until I met his eyes. "If you decide you want to try, I'd love to be your first. And I promise I'll take care of you."

Something warm bloomed in my chest. This was why I was falling for Noah. He never pushed, never made me feel inadequate for my inexperience. He just... accepted me, exactly as I was, while leaving the door open for who I might become.

"I want that," I said. "With you. But can we... can we take it slow? Work up to it?"

His smile could have lit up the whole room. "We can take as long as you need."

Over the next few weeks, Noah introduced me to new sensations gradually. First just his finger during oral, circling and teasing, never pushing past what I was ready for. The first time he slipped inside—just the tip of one finger—I gasped at how different it felt from anything I'd expected.

"Good different or bad different?" he asked, pausing immediately.

"Good. Really good. Keep going."

He did, and by the end of that night, I understood what all the fuss was about. The fullness, the intimacy, the way he could press against spots inside me that made my whole body light up—it was a revelation.

We progressed slowly. One finger became two. Two became three. He introduced me to toys—small ones at first, then gradually larger, always letting me set the pace. Through it all, he was endlessly patient, endlessly encouraging.

"You're doing so well," he'd murmur against my skin. "You're so beautiful like this."

And I started to believe him.

The night it finally happened started like any other. We had dinner at our favorite Thai place, walked back to his apartment through streets soft with early spring rain. By the time we got inside, we were both slightly damp and laughing about something stupid—I don't even remember what now.

He kissed me in the doorway, slow and deep, and I felt my body respond the way it always did to him. But tonight there was something else underneath it. A readiness I hadn't felt before.

"Noah," I said when we came up for air. "I think I'm ready."

He searched my face. "Are you sure? There's no pressure—"

"I'm sure. I want this. I want you."

He took my hand and led me to the bedroom, but instead of the urgency I expected, everything slowed down. He undressed me like I was something precious, kissing each inch of skin he revealed. By the time I was naked on his bed, I was already trembling with anticipation.

"We're going to take this slow," he said, pulling off his own clothes. "And you tell me if anything doesn't feel right, okay? We can stop anytime."

"Okay."

He started with his mouth, bringing me to the edge twice before backing off. Then came his fingers—one, then two—slicked with lube and working me open with familiar ease. But tonight he took extra time, extra care, adding a third finger and scissoring gently until I was loose and desperate.

"Noah, please. I'm ready. I need—"

"I know, baby. I know."

He rolled on a condom and positioned himself between my legs. I could feel the blunt pressure of him at my entrance, and my heart was pounding so hard I could hear it.

"Look at me," he said.

I did. His eyes were dark with want, but there was so much tenderness there too. So much care.

"I've got you," he promised. "Just breathe."

He pushed in slowly—achingly slowly—and I felt myself stretching around him. It burned, but not unbearably. Mostly it was just... overwhelming. The fullness, the intimacy of having someone inside me like this. I felt tears prick at my eyes.

"You okay?" Noah asked, freezing. "We can stop—"

"Don't stop. Please don't stop. It's just... a lot. But good. So good."

He leaned down and kissed me, swallowing my gasps as he pushed deeper. By the time he was fully seated, I felt like every nerve in my body was on fire.

"How does it feel?" he asked.

"Full. Like... like you're everywhere. I can't even describe it."

He started to move—tiny, shallow thrusts at first, letting me adjust. Then longer strokes as I relaxed around him. The burn faded, replaced by a pleasure unlike anything I'd experienced before.

When he angled his hips and hit that spot inside me—the one his fingers had found but that felt completely different with his cock—I nearly screamed.

"There?" he asked, hitting it again.

"Yes. God, yes. Right there."

He found a rhythm, steady and sure, hitting that spot with every thrust. I was a mess—moaning, gasping, hands scrabbling at his back. The pleasure built and built until I wasn't sure where I ended and he began.

"Touch yourself," he said, and I wrapped a shaking hand around my cock.

It only took a few strokes. The combination of his cock inside me and my hand on my shaft pushed me over the edge, and I came harder than I ever had in my life. My whole body clenched around him, and he followed seconds later, my name falling from his lips like a prayer.

After, he held me while I cried.

Not from pain—there hadn't been much of that, thanks to his patience and preparation. I cried because of the release, the vulnerability, the overwhelming rightness of finally experiencing something I'd wanted for so long. I cried because I'd been so scared, and it had turned out to be beautiful.

"I've got you," Noah murmured into my hair. "I've got you."

When I finally calmed down, we lay tangled together in comfortable silence. He'd cleaned us both up at some point, and now his fingers traced gentle patterns on my hip.

"Thank you," I said eventually. "For being patient. For making it... for making it perfect."

He kissed my forehead. "Thank you for trusting me."

"I love you," I said. The words came out before I could stop them—we hadn't said that yet, though I'd been feeling it for weeks. "Sorry, I know that's—"

"I love you too," he interrupted. "I've been wanting to say it for a while."

I smiled against his chest. "Yeah?"

"Yeah."

That was six months ago. We've explored so much since then—different positions, different toys, switching roles. But I'll never forget that first time: the fear and the anticipation, the burn and the bliss, the feeling of being completely and utterly seen.

If you're nervous about bottoming for the first time, here's what I wish someone had told me: Find someone you trust. Someone who will go at your pace, who will check in constantly, who cares more about your experience than their own pleasure. Someone who will hold you if you need to cry after.

And don't rush it. The buildup—the fingers and toys and patience—isn't something to get through. It's part of the experience. Enjoy it.

Most importantly: it gets even better. That first time was special, but it was just the beginning. Every time since has been a new discovery.

I'm so glad I finally took that leap.