My First Boyfriend

It all started when I turned 18. I hadn't been allowed to formally date anyone, let alone call them my boyfriend. Sure, I had been on dates, but they hadn't ever led anywhere - my mother made sure of that.

But a month after my 18th birthday, it happened. A boy, a half year older than me, won me over with a cheesy pick up line.

He had drawn a simple squiggle line on the back of my hand, calling it a river. Next he drew a small dot, labeling it a bunny. I watched intently as the pen left ink across my skin, only looking up when he asked, "How does the bunny cross the river?"

I met his pretty eyes, noticing how unruly his hair was, and answered with an uncertain, "I don't know... How?"

"I don't know, I just wanted to hold your hand."

That's what settled it, we went on a movie date a few nights later. I got dressed up, a tight fitting shirt, a short skirt, and some heels. We watched some superhero movie, and made out afterwards. He grabbed my ass and pulled me closer, I could feel the beginnings of an erection building in his pants.

It was late and he had to take me home, but we would pick up from where we left off two days later.

I was in his room, despite my mom telling me to stay out. Hell, I was responsible and an adult now. We were laying on his bed, spooning, and he started talking about how he liked doing it in the ass - couldn't get girls pregnant that way. I felt something poke my asshole - his finger. I was wearing another skirt, and he was pumping in and out.

It felt... Weird. Not entirely undesirable, but I didn't quite know what to make of it.

I went home shortly afterwards, feeling a bit confused. Though that wouldn't last for long. We saw each other every day for a week at high school - finishing up our last year. We made out in the halls. His tongue down my throat, me pulling his hair, his boner poking me from all directions.

I went back over to his house during the weekend, and again I went into his room. Before I knew it, he had managed to take off my jeans and panties and had begun fingering my pussy.

"Does this feel good?" I remember him asking.

There were no words to describe the feeling. He pushed in and out, speeding up and adding more fingers. I was so wet, and even though I knew it was wrong, I couldn't bring myself to say stop.

In and out, in and out. I had almost reached my climax when his fingers disappeared and was replaced with something much larger. I looked him in the eye, shocked, my mouth slightly gaping.

It hurt, a hell of a lot more than I was expecting. Tears ran down my face as I realized this wasn't what I wanted. I shook my head fiercely. Despite this, he pushed forward, just a little, claiming that it'll get better soon. Still, I protested.

He caved and pulled out, then returned to fingering md immediately. I didn't have time to respond as my body was thrown into a wave of pleasure.

The rest of my time cycled between him pleasing me and him trying to fuck me. My protests grew weaker as I was lost within the way he was making me feel. Eventually, I got the strength to get up and fun out of the room crying. I locked myself in his bathroom, sobbing, and threw up my lunch. I left shortly after.

Our breakup came within hours of me returning home, the regret seconds after the break up. I was alone at home, fingering myself, only to find that I missed his masterful fingers.

My fantasy played out in front of me as I kept doing the movements...

I was back at his house, naked. He was fingering me. His fingers moved faster and faster, until they ceased. He took them out and replaced them with his dick - ready to punish me for ending the relationship so soon.

I stuck in the handle of my hairbrush and began pumping furiously...

Without bothering to ask, he rammed into me. He was done taking things nice and slow if I wasn't going to accept him. It hurt, but he didn't give me time to adjust. He began fucking me fast and hard, forcing little pants and moans to escape my mouth.

A gushing liquid escaped my pussy, soaking the bed. I laid still for a few minutes, wondering if I should apologize and beg him to take me back.