“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.
Slipping my hand down, I dipped my fingers into my panties, touching my clit. I moaned at the touch, forgetting where I was. I watched him as he pulled himself free, and I sucked in a breath at his length. My fingers dipped into my core, my juices coating me as I found myself climbing toward a release I didn’t think was possible.
“Oh, shit,” I said. “That’s hot.”
“Hearing you say that makes me want to blow. You’re one to talk, Rose. I think you’re the most beautiful girl I’ve ever seen. Watching you is the best experience of my life.”
“You’re a sweet talker, Cowboy. I’m close. Cum with me.”
I sped up, plunging deep as I rode my own fingers. I was surprised at myself for being able to do this, but it felt safe. I was in control here, and I did trust Cowboy to some degree. He let me lead the session, choosing to do what I was comfortable with, and didn’t make me feel like I owed him anything. Even if he was paying me. It did wonders for my healing.
Crying out, I tightened around my fingers as I came. I was barely able to keep my eyes open as I watched him come, his release squirting out in jets onto his stomach. Those delicious abs that I wanted to lick now.
The thought surprised me, and I found myself pulling back, needing some space.
“Wow, that was um, yeah,” I mumbled, feeling embarrassed now.
“No kidding. I don’t think I’ve ever cum so hard. It makes me wish this was real, you know. But even still, it was the best experience of my life, Rose.”
His voice was so kind, so awestruck, that the humiliation disappeared.
“You’re welcome, Cowboy. Have a good night.”
“Bye, Rose.”
“Bye, Cowboy.”
I turned off the camera, shut the laptop, and I laid back in the bed, replaying everything. I just had my first consensual sexual experience, and it hadn’t sucked. It only took about ten months, but I felt like I was finally on my way toward healing. And a shy guy named Cowboy had helped me get there.
Diary #9
Dear Mom,
I can’t believe it’s been a year since everything happened. I miss Dad. I wish I could talk to him. I miss his hugs and his voice. I want to know how things are, but it makes me worried that it would be worse to know.
I miss Maddox too. Even if nothing ever came of us, I miss his friendship. He was that shadow, that looming presence who was always there, watching over me. Our chats aren’t the same.
I miss motorcycles. The noise, the smell, the way they feel between your legs. The power I had riding on one. I miss it all.