That Was Unexpected

“What’s up?”

The simple little text that popped up on my phone from Brian.

My reply was just as casual and probably a little too nonchalant.

“Not much.”

And that folks, is how the night adventure began.

I softened the tone, kept it feminine and reflective, and faded the scene before it becomes explicit:

Brian and I have been friends for almost two years now. We met through mutual friends, and he was one of the guys at the lake house on Sunday. We kept texting afterward, and at one point he mentioned that he had noticed Justin flirting with me. He admitted it made him think two things. First, that it probably wasn’t right. And second… that he was a little jealous.

That completely caught me off guard.

Brian and I had never done anything before. Honestly, we’d never even really spent much time alone together. Then, out of nowhere, he finally worked up the courage to ask, “Meet me at Ocean Annie’s in thirty?” I was more than happy to get out of the house, especially since I’d been fully prepared to spend the evening alone. So I slipped into a cute little dress, put on my favorite heels, and headed out.

I didn’t know he’d recently gone through a divorce. And if I’m being honest, I had never really stopped to notice just how handsome he was. I may or may not have kept finding excuses to touch his arm throughout the night because… well, it felt nice. We talked about life. We talked about losing my parents. We talked about my plans to travel and the fact that I honestly have no idea how long I’ll be gone. By my second drink, Brian had gotten a little bolder. Every now and then, his hand would rest on my leg, lingering there just long enough to make my heart flutter. I couldn’t deny that I liked the attention. We kept talking, and I kept letting the evening unfold.

Still, I found myself overthinking. Maybe he’s nervous. Maybe he’s not sure what this is. Maybe he’s trying to decide if he should cross that line. Eventually, I let my own courage take over. The next time his hand rested on my leg, I uncrossed them, closing the distance between us just a little.

I think he understood exactly what I was saying. I leaned over and softly whispered, “We can’t just sit here all night. Want to find somewhere else to go?” The moment we walked outside, he took my hand and led me toward his truck. He spun me around and gently leaned me back against the cool metal of the door, sending a shiver up my spine.

This was a different Brian than the one who’d seemed so hesitant earlier. There was something in the way he looked at me that made my heart race. Suddenly, all of the harmless flirting didn’t feel so harmless anymore. Looking back, I think I knew right then that the night had changed. He opened the passenger door and lifted me onto the seat, standing between my legs, and for a moment I stopped him.

Because sometimes “no” is okay. Especially when this isn’t how I wanted it to go.

I smiled and said, “Let’s go to my place.”

His eyes widened and he grinned in a way that made me laugh. He looked almost boyishly excited.

The second we walked through my front door, the energy between us shifted again.

His boots came off. My heels followed. The straps of my dress slipped from my shoulders. And for a brief moment, we simply looked at each other. (More him admiring me than me looking anywhere)

I remember thinking how strange it is that someone you’ve known for so long can suddenly feel entirely new.

I stepped closer, my heart racing, wondering where this unexpected night was about to lead us.

I slowly lowered down onto my knees. Looking up at him. My body almost trembling with excitement, or nervousness. Either way. Trembliing.

My right hand reached up and undid his belt, then the button, then the zipper to his jeans. I could easily see the bulge. Slowly, while not losing eye contact, pulling his jeans down.

“Tight boxer briefs. I like it”… I thought to myself. Then, looking straight ahead I saw what was waiting. The thick bulge that seemed to be growing thicker. One hand, then the other, grasping the waistband of his boxers.

About a year and a half in the making, and it comes to this. I pull down and his cock sprung free, almost slapping my forehead. I let out a chuckle. He didn’t think it was as funny as I did. Then. Oh, his cock. It wasn’t so long as it was thick. Like thick! Wrapping my hand around it, and my fingers couldn’t touch. My thoughts went to “How am I even going to work this with my mouth?!?!”

I looked up at him, my tongue tracing circles around the bulging tip, My hand slowly stroking it. I opened my mouth wide and took the head of it in. I could barely get my mouth around it and I was worried my teeth were going to drag against him. A little more, I can get a little more in. I released, spit on it, and then did it again, now my hand sliding on the shaft that my mouth couldn’t get to. My other hand began going lower down the shaft massing the rest of him.

I remember letting out muffled moans in an attempt to get more of him in my mouth. It wasn’t as if I now had a mission. I felt myself dripping with anticipation but just wasn’t ready to stop this challenge.

He was definitely looking down at me, almost in a comical way. I probably looked like such a freak or such a slut. Just trying to see what I could do.

Grabbing my hand he pulled me up. I couldn’t take my eyes off his cock though. It was just so thick. Surely a top 5 for thickness in my book.