Not too long after my first time fooling around with Sean, okay who am I kidding. We didn’t just fool around. I went down on him, sucking his cock until he took over and fucked my tits and it wasn’t long before he deposited his cum all over my face and cleavage. After all of that, it wasn’t long before did more. The following night I snuck over to his house and that time he made sure he had condoms. It wasn’t long before we were having sex at least once a day. The sex was good, sometimes great, but that’s not the story I want to tell you this time.

This time I want to tell you about the night his parents were out of town and I stayed over at his house. We didn’t even pretend to watch a movie this time. We went straight up to his bedroom and practically ripped off each other’s clothes.

We did a lot of things that night. I sucked his cock until he shot his cum into my mouth. He went down on me and made me scream. We fucked a lot. We fucked missionary. I rode him. He fucked me doggy style. By the time we were done and collapsed on to the sheets, he had filled three condoms. It was the most times I’d ever made a guy cum in one night and if we could’ve kept our eyes open, we would’ve kept going.

I woke up first when the sun started coming through the crack in the window drapes. With his naked body next to me, the first thought to my mind somehow was more sex. Unfortunately, my second thought was to check the time. I had to work the morning shift that day at my part time job and I’d have to go home first to shower and get my uniform. So instead of reaching over for his cock, I reached to my phone on the nightstand. The time on my phone said that I had to hurry if I wanted to get to work on time.

I climbed out of bed without waking him and started finding my clothes on the floor. I had only put my bra and thong on when Sean rolled over and looked at me. “What are you doing?”

“I have to go to work.” I said, then pulled on the t-shirt I had worn the previous night.

“Just a quickie?” He pulled back the sheet to reveal his morning wood.

“I can’t.” I couldn’t help but checking out his erection. My body said yes, but I couldn’t risk being late to work. I had already been late twice in the past month and the last time the nice boss even warned me that he would have to write me up if I was late again.

He stood out of bed and I thought he was going to put something on so he could walk me to do the door. Instead he wrapped his arms around me and kissed me. His touch and tongue made it harder to ignore my body’s desires. He slid his hand into my underwear, not stopping until he reached my lips. “Just a quickie.”

“Just a quickie.” I said with a giggle. Hopefully it would be the nice boss working and maybe I could talk him out of writing me up.

Before I could finish my sentence, he had me back on the bed. He used his strength to guide me to my back and climbed on top of me right away. He pulled the thin fabric of my underwear to the side and was ready for us to pick up from where we had left off the previous night.

“Whoa.” I said as I used my hand to block him from penetrating me. “Slow down. Where’s the condom?”

“I’ll come quicker if I can fuck you without it.”

I gave him a disapproving look and he climbed off of me to reach into his night stand. He took out a condom and wasted no time putting it on.

He positioned himself over me and this time I didn’t try to stop him. He pulled my underwear to the side again and pushed into me. I wasn’t quite ready for him, but at the same time I couldn’t get enough of him.

He didn’t take his time, or start of slowly. He filled me, pulled back, then pushed deeper into me. It felt good, but this was definitely for him.

It wasn’t long before we were both breathing hard and starting to sweat.

He drilled his cock into me with the only sounds being our bodies colliding every few seconds.

I expected him to come quickly. Usually the first time, he came quickly, then the second time he would last longer. However, I guess this wasn’t a regular first time. We had just had sex six hours earlier and we had been sleeping most of that time in between.

I need him to come quickly and did more than just lay there. Underneath him, I moved almost as much as he did. On top of him, I rode him as hard as I could. My whole body bounced up and down on his hard shaft. Still, we were nowhere closer to his orgasm.

I slowed down and came to a stop before I asked, “What can I do to make you come?”

“Let me fuck your ass.” I thought he was joking until he grabbed my ass with both hands.

“No way. Anything besides that?”

“Have you ever done it?” He said as he ran a finger between my ass cheeks.

“No.” I said as I pushed his hand away.

“You might like it.”

“Or I might not.” I’d heard from a friend who had done it and her review was very negative. She said she’d never felt anything so painful, so I was in no rush to do it myself. I wanted to get to work quickly, but I thought I could make him come another way.

I returned to riding him, but couldn’t get him any closer. After another minute or two, I stopped again. “Fuck me doggy style.”

He answered by flipping me off of him and on to my hands and knees. He set himself up behind me, but he didn’t push his cock into my pussy as I was expecting. Instead he slid his cock between my ass check. I’ll admit, the feeling made me squirm as the pleasure rushed through my body. Against my better judgment, I didn’t stop him. Instead a moan somehow escaped from my lips.

He pushed me on to my stomach and pushed his head against my asshole. How much could it hurt?

The grin on my face disappeared as he forced his cock into my ass. He didn’t even get more than the tip of his cock into my ass, but it hurt like nothing I had ever experienced before. A sharp pain that ripped through me. I tried to move away, but he held me in place as he tried again.

This time he pushed harder until his cock entered my tight asshole. I felt my eyes starting to water and I closed them.

I should’ve demanded that he stop, but I didn’t. I wanted to make him come one way or another, but it was more than that. I wanted to experience it for myself and deep inside of me I think I liked it, not the feeling, but that I was now the kind of girl that let a guy penetrate her ass.

I could feel inch by inch as he penetrated me. The pain grew as his cock filled me. All I could feel was the pain. It hurt like hell.

The pain didn’t fade away as he slowly pulled back either. It was still there as he started to fuck my ass. My tight, no longer virgin ass. I couldn’t believe that a guy was inside of my ass, let alone Sean. I had a feeling half of the school would eventually find out and I didn’t care. I just wanted to make him come and quickly as possible.

His thrusts were hard and fast, which did little to reduce the pain. After a minute or two, I did start to get used to the feeling, but I wouldn’t say it felt good by any means.

Then as quickly as it started, it was over. He slammed hard into me one last time and came to a stop. He came hard with a deep groan. I’d never felt him or any guy come so hard.

He pulled out and the pain finally started to fade away, however it didn’t go away. It still didn’t seem real. I was no longer an anal virgin and even though it hurt so bad, I wanted to do it again.

What was definitely real was that I had to get up and hurry to work. A half hour later when I walked into work, my ass was still sore. I was also very late, luckily the nice boss was there and I just had to flirt my way off of his bad side. Another thing, the old me would never have done.