1st time

1st time 1st time

Status: Finished

Genre: Erotica


Status: Finished

Genre: Erotica


Anna's first time.


Anna's first time.


Submitted: March 31, 2012

A A A | A A A


Submitted: March 31, 2012




March, 30th

I’d told my mom I was going to see Brittney, a girl who doesn’t exist. Then I went and met him at the school.

“Hi stranger,” he said wrapping me in his arms. We’d planned to stay at the school but there were people there. “Let’s go toward the ball field instead” so we did. We talked about what had been going on in the week we were apart, Even though we’d texted every day. Once we cut across the church parking lot a brown dog started fallowing us. We walked all the way around the ball field, and then went into a dugout. I laid down my bag which carried 5 dollars and 2 condoms. I knew what he was carrying too, a bottle of lube. He put his arms around my waist and held me close; we talked like this for a while. He was at least a foot taller than me so my head came even with his chest. He ran his hands up and down my sides and back all the way to my hips. “You’re beautiful” he said smiling down at me looking straight into my eyes. He bent his head down and kissed me. It wasn’t our first kiss but it was the first of that day, we continued like that, talking and kissing until we heard the sound of gravel under tires, it was a field maintenance man. We walked back up the hill past the man who was fiddling with the lock on the gate. We didn’t know where we were going but we started walking again. He took my hand, in the shadow on the street I looked like a little kid, probably because he was so much bigger than me.  Eventually we realized we didn’t have any were to go, we started back toward the ball field. The man was still there so we hung around the tree line near the woods.

“I know my way in these woods ya know” I told him, we were seeking more privacy.

“Ok, let’s go” he wasn’t very good with all the underbrush but what did I expect, He was from New York City. Once we got to a clearing he kissed me again. Sliding his tongue in my mouth and wrapping it around mine. He held me close. I could feel him through his basketball shorts, he was getting hard.

“What do you want to do?” he asked, last time this question led to him fingering me.

“You did something for me last time; I’ll do something for you this time.” I said.

“Okay,” he said kissing me “what?”

“I could give head” I suggested like it was nothing even though in reality I’d never done that before.


“Whenever you want me to” he kissed me again sliding his hand down my skirt, he put one finger inside me, then two. It felt good.

“Do you want to now?” he asked. I could tell he was trying to have it sound like he wasn’t making me do anything. But I wanted do.

Without saying anything I dropped down to my knees he pulled down his shorts part of the way and pulled his dick out of his boxers.

“I’m small” he said. He really wasn’t though my first thought was I’m going to have to take this inside me? That’s going to hurt like hell.

“No you are not.” I put my hands on his thighs to keep me up. And slid his dick in my mouth, then back out, I tried to go as far down as I could without choking. After a while I realized his hands were on my shoulders pushing me back and forth.

“Good, bad?” I asked.

“Good” he replied. I continued, soon my mouth was full, not just of spit. He’d come, it dripped down into my shirt on my chest. I swallowed because I heard that’s what you’re supposed to do. We continued like this for a little while. Then he asked “do you want to do 69? I can lie on the ground here.”

“Umm… okay” He lay on his back.

“Do you know how to do it?” I shook my head. “I’ll lick while you give head.”

“Okay…” he touched one of my legs. “Bring this one over here,” I did and I lay with my stomach on his. “Move up a little…” I took his dick in my mouth again; he slid his tongue into me. I could barely feel him but I was worrying about so many other things at that time. Weather he was enjoying this, weather I was getting to heavy laying on him, and worse of all, weather we were about to get caught. Once I calmed down I realized whatever he was doing felt good. I could go down farther on his dick in this position. He lifted up my skirt all the way. I was completly exposed. Eventually I stood up, I was pretty sure I’d gotten to heavy even though he reassured me I hadn’t. “Do you want to do anal?” he asked. This worried me. I was a virgin, he was not. At least he’d know what he was doing. But I also heard that if you do this wrong It hurts really bad.

“Okay” I finally said.

“Are you sure?” I nodded. He took out the bottle of lube. I turned around and put my hands on a branch. He put lube on. Then very gently tried to slide into me, I didn’t work I was too small.  Finally it slid in And pain flowed through me. I took a sharp inhale then moved away. “Are you okay? Did it hurt?”

“It hurt” I say a little panicked


“pretty bad”

“I’m sorry, I’m so sorry” he put his hand on my shoulder.

“I’m sorry” I said leaning on him. 

“We can use more lube.” he suggested, “and I’ll go slow” I nodded. We tried again; it didn’t hurt so badly now, Even though it did hurt. After a while It didn’t hurt at all it actually felt good. He grabbed me at my hips, we moved in sync. After a long time he asked “Am I boring you?”

“No. Are you bored?”

“No.” When he finally pulled out I was spent. I could’ve laid down right there but I didn’t. I checked my phone, it was 12:50.

“I got to go soon”

“Ok” he gave me a hug and kissed me good bye “I love you”

“I love you too”

© Copyright 2019 Jennifer Monroe. All rights reserved.

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