First Time Trust

This is one of those anal sex stories that starts with curiosity and ends with a whole new dimension of intimacy. It's about trust, communication, and discovering that some of the most intense pleasures come from venturing into the unknown together.

My name is Emma Sullivan. I'm twenty-nine, a physical therapist, and I've been with my boyfriend Ryan Martinez for two years. We have a great sex life—or at least, I thought it was great until the night Ryan admitted there was something he'd been wanting to try.

We were in bed after making love, that lazy post-orgasm haze when all defenses are down and honesty comes easier.

"Can I ask you something?" Ryan's voice was hesitant, which was unusual for him.

"Anything."

"Have you ever thought about... trying anal?"

The question hung in the air. I'd been asked before, by previous partners, and my answer had always been an immediate no. Too scary. Too painful. Too... dirty. But something about the way Ryan asked—not demanding or entitled, just curious—made me actually consider it.

"I've thought about it. Never done it."

"Would you be open to exploring it? With me?" He propped himself up to look at me. "I'm not trying to pressure you. I just... I want to experience everything with you. And I've heard it can be really intense for both people, when done right."

"I'm scared it'll hurt."

"It won't if we do it properly. Lots of prep, lots of lube, going really slow. We can stop anytime you want. The second you're uncomfortable, we stop. No questions."

I looked into his eyes—this man who had never pushed my boundaries without permission, who always prioritized my pleasure, who I trusted completely.

"Okay. Let's try."

We didn't rush into it. Ryan—ever the planner—did research. He came home a few days later with supplies: premium silicone lubricant, a set of graduated training plugs, new sheets "because we should make this special."

"We're going to take our time," he explained, laying everything out. "The plugs help you get used to the sensation gradually. We'll use them during regular sex for a few weeks before we try anything more."

"You really researched this."

"I want it to be good for you. That means doing it right."

The first time he used the smallest plug on me was during oral. He was between my legs, his tongue working its magic, when I felt him press the lubricated toy against my ass. Just pressure at first—no penetration.

"Tell me when you're ready."

I nodded, too lost in sensation to speak. Slowly, as his tongue continued its work, he pressed the plug inside. It was small—barely wider than a finger—but the sensation was strange and new. Foreign.

"How does it feel?"

"Weird. But... not bad weird."

He continued pleasuring me with his mouth while the plug sat inside me. When I came, the orgasm was different—deeper somehow, like it was radiating from multiple places at once.

"Oh my God," I gasped. "That was..."

"Intense?"

"So intense."

Over the next few weeks, we progressed gradually. Larger plugs. Longer wear times. Ryan would fuck me with a plug in, and the dual sensation was mind-blowing. I started to crave it—the fullness, the taboo thrill, the way it intensified everything.

The night we finally tried the real thing, Ryan made it an event. Candles. Music. A long, hot bath together beforehand. By the time we got to the bedroom, I was relaxed, aroused, and ready.

"We're going to go so slow," he murmured, positioning me on my hands and knees. "I'll check in constantly. You say stop, I stop. Okay?"

"Okay."

He started with his fingers—one at first, well-lubricated, moving gently while his other hand played with my clit. The sensation was familiar now, comfortable even. When he added a second finger, I moaned.

"More. I want more."

I heard him apply more lube, felt him position himself at my entrance. The head of his cock was bigger than any plug we'd used, and I tensed automatically.

"Breathe, baby. Push out a little, like you're trying to let me in."

I did as he said. Breathed deep. Relaxed my muscles. Pushed out slightly. And slowly, inch by inch, he entered me.

The stretch was intense but not painful. He'd prepared me well. By the time he was fully inside, I felt impossibly full—stuffed in a way I'd never experienced.

"How are you doing?"

"I'm okay. I'm... God, I'm so full."

"I'm going to move now. Slow."

He pulled out slightly and pushed back in. The sensation made me gasp. It was so different from vaginal sex—more primal, more intense. I could feel every ridge of him, every movement amplified.

"Faster," I heard myself say. "I can take it."

He picked up the pace gradually. His hands gripped my hips, and his thrusts grew more confident. When he reached around to circle my clit with his fingers, I nearly screamed.

"Oh God. Oh fuck. Ryan—I'm going to—"

The orgasm that hit me was like nothing I'd ever felt. It started deep in my core and radiated outward, wave after wave, my whole body convulsing around him. Ryan groaned and thrust deep, and I felt him pulse inside me as he came too.

Afterward, we lay together, my head on his chest, both of us still catching our breath.

"That was..."

"Yeah."

"Why was I scared of that for so long?"

"Because it's scary when you don't trust your partner. Or when they don't take the time to do it right." He kissed my forehead. "I'm so glad you trusted me."

"I'm glad too."

We didn't do it every time after that—it became something special, reserved for nights when we wanted extra intensity. But it opened up a whole new dimension of our intimacy. It showed me that with the right partner, the right preparation, and the right communication, things that seem scary can become sources of incredible pleasure.

⏳ Six Months Later

I'm writing this because I know there are other women out there like me—curious but scared, wanting to try but worried about pain or judgment. These anal sex stories you read online often skip the important parts: the preparation, the communication, the trust that has to be there before anything else.

My advice? Find a partner who cares more about your pleasure than their own. Take your time. Use more lube than you think you need. And don't be afraid to explore—your body is capable of pleasures you haven't even imagined yet.

Ryan showed me that. And I'm forever grateful he did.