Page 31 of Music City Diaries

“I’ve never really done this before. I mean, I’ve done stuff with girls, but I mean here, online. However, if I’m being honest, my experience is limited with girls. My name is pretty accurate. I’m shy in real life, and I usually talk myself into twisted nonsense with girls as pretty as you.”

“Well, believe it or not, I’m not that experienced either.” I bit my lip, hoping he wouldn’t hold that against me.

“Really? I’d never be able to tell. You always seem so confident.”

“It’s just me stepping into that persona. Or, I guess I am confident in general, or I was at one time.” My voice trailed off, going quiet. “Anyway, so we both are new to this. You’re my first private session.”

“Wow, really? I’m kind of honored.”

“Good.” I smiled. “So, what do you want to do? Do we just like talk, or, you know?” I asked, laughing a little.

“It’s kind of freeing to know you don’t have expectations. Would it be okay if we just talked for a little bit?”

“Absolutely.” I wanted to say he was paying for it, so we could do whatever, but I didn’t want to cheapen it. “So, what made you try Cam Girls?”

“It seemed like an anonymous way to become more confident.”

“That makes sense. So, what do you do?”

“Well, would you believe it if I told you I was a cowboy?” He laughed, and his southern drawl became my favorite sound.

“The name makes more sense then.” We talked for ten more minutes, things becoming more relaxed. “So, Cowboy, if this was a real date, what would you do right now?” I asked.

He cleared his throat, taking a breath. “Assuming this is the version of myself that doesn’t screw things up, then I’d kiss you.”

“Oh? That’s a good place to start. How would your lips feel on me?”

“Hm, hard, but soft. I’d want to taste you, but wouldn’t feel like I had enough time.”

I sucked in a breath, his description entrancing me. “That sounds nice. What would you do next after this kiss?”

“I’d want to touch you all over.”

“Like this?” I asked, skating my hands over my breasts, trailing it down my stomach.

He swallowed. “Yeah. You’re so beautiful, Rose.”

“Thank you, Cowboy. You know, you’re not so bad at this. Where would you want me to touch you?”

“Oh, um, I don’t know. I usually focus on the girl because I’m so afraid she’s going to run away.”

I laughed a little. “Oh, Cowboy. This is a fantasy, so let's both get some. Show me where you’d want me to touch you and how.”

“Okay.” He gulped and moved his hands down his stomach. I watched as he rubbed his hand over his boxers. It was hard to see since he was sitting mainly in the dark, but I could make out his shape.

“How far do you want this to go?” I asked, slipping a strap down.

“Um,” he paused, focused on my fingers. “What are you comfortable with, Rose?”

It was the first time a man had ever asked me that I realized. I stopped, thinking about it. I looked on the timer and saw he had twenty minutes left.

“What if we show whatever we both feel comfortable with since it’s our first time?”

“Yeah, I’m good with that,” he said, shaking his head. I still couldn’t see more than his chin, but every now and then, I’d catch his movement.

I sucked in a breath, dropped my other strap, and pulled my bra off. Slowly, I moved it to the side and brought my hand back to my breasts. I was too nervous to look at the screen, though. If I just focused on myself, then it didn’t feel so scary. To be honest, it didn’t feel as terrifying with Cowboy.

Pinching my nipples, I finally decided to brave it and looked up. His hand was inside his boxers, stroking himself. I thought I’d be indifferent to someone else pleasing themselves, figuring I’d have to go to a place in my mind to get off. But as I watched him fist his cock, stroking it as he looked at me, it did something for me.

---