I turned toward him. “Please don’t say that like it’s easy. Because it’s not. I care about all of you.”
They were all waiting, clearly ready and wanting me, but no one moved or pressured me. They were giving me space, and time, and the chance to make this mine. That meant something.
I took a shaky breath. My chest was tight with nerves, but underneath that, there was still a clear pull. And I knew I was going to go through with it. I just needed a second to be sure.
“I don’t want to stop,” I said again, firmer this time. “I just…need a moment.”
I glanced at each of them again, taking in their expressions. All four of them held something different. Comfort. Desire. Love. Safety. There were reasons for any of them to be the first. But one name kept tugging at the front of my mind.
“Okay,” I said softly. “I think I know now.”
I looked at Tripp, my gaze locking with his. “I want it to be you.”
“Are you sure?” he asked. His hand touched my lower back gently, foreshadowing how careful he would be with me.
“I’m sure,” I nodded. “But…I still want the others close. I want them to hold me.”
It sounded silly once I said it out loud, but it was important to me. I didn’t want to be separate from them. I wanted to be surrounded by them.
“We can do that,” Tripp said simply. He looked over at the others and gave a soft nod. “Sit down.”
They moved to the biggest couch without hesitation, arranging themselves with Dash in the center. Their bodies were bare, showing off just how perfect they all were.
I stood for a second, just taking it in, and then nodded to encourage myself before walking over and settling down between Dash’s legs. He wrapped his arms around me from behind, his chest pressed to my back. Rhys and Ashby moved closer, each of them running a hand over my thighs and arms. They were reassuring me, giving me comfort. That’s how I knew my first time would be perfect.
Tripp had walked away for a moment before returning with a bunch of condoms which he threw onto the coffee table behind him. Then he stood in front of me, stroking himself slowly, his eyes moving slowly over my body as he unwrapped a condom to slide it over his length.
“If anything feels off, if anything changes, say the word. You stop me, and I stop. No hesitation.”
I looked up at him. “I won’t need to. I want this.”
His eyes met mine then, and he nodded. “Okay.”
Tripp leaned over me, his face close to mine before he kissed me softly. I kissed him back, and my mind immediately started racing. I was trying my best to stay calm. I wanted this to be perfect, and I couldn’t let my overthinking ruin this moment.
I told myself to focus on Tripp. On the kiss. On the others’ hands on my body.
Then I felt the tip of Tripp’s cock press gently against my pussy. He wasn’t pushing in. He just rested it there, slid it up and down slowly to give me a feel of it. My body tensed instinctively, even though I’d been wanting this, thinking about it, saying I was ready. Now that it was really about to happen, it felt different and overwhelming. But I managed to stay calm.
He didn’t move away. He just stayed like that. He was close and patient. And maybe that was supposed to be comforting, but it was starting to mess with my head a little. The longer he waited, the more I started overthinking everything. I could feel myself clenching up without meaning to.
My voice came out smaller than I intended. “Is it going to hurt?”
Tripp pulled back just enough to look me in the eye. His expression didn’t change much. Still soft and calm and reassuring. “You’ve had my fingers in you before,” he said gently. “Did that hurt?”
I shook my head, my face heating up although I wasn’t embarrassed. I had liked his fingers inside of me. That had felt nice. “No…it felt good. Really good. But this is different. You’re…well, you’re a lot bigger.”
His mouth twitched. He pressed his lips together for a second, nodding like he understood what I was saying.
“I know,” he said. “And I’m not going to just push in all at once. I’ll take it slow. We’re not in any rush.”
He meant it. I could see it in his eyes. He wasn’t trying to brush off my nerves or pretend this was going to be some perfect, movie-worthy moment. He just wanted me to be okay. That helped. Not enough to make the nerves disappear completely, but enough to let me breathe normally.
“I need you to tell me if anything feels off, alright?” he added, his hand gently resting on my hip. “Even a little bit. You stop me if you need to.”
I nodded. My body was still tense, but something about the way he was talking, so normal and direct, and not trying too hard to make it sound magical, made it easier to stay in the moment.
“Okay,” I said softly. “Just…go slow.”