Sex Short Stories

Very First Time

One day, after spending hours on in at work, I got off. I packed my things and headed to my grandmother's house, but not before making a few stops. On my way to her house, I stopped by the nearby clothing store, I looked around and of course found nothing I wanted. While in there, though, I bumped into one of my old friends siblings. We spoke and I thought nothing of it. I walked out of that store, and into the next store, which happened to be a target. Me being who I am, I ran straight to the makeup, where I bumped into my friend and his mother.

Now, just a small backstory, me and him used to date and last I knew, he didn't like me. But as we talked I sensed he still did. Dressed in cargo shorts and a black U.S. Navy hoodie, he held and iPhone 6 plus. He used a headband to hold back his hair and oh man was he hot. He had really grown up since middle school.

Anyway, as we continued to talk I pulled him onto another isle so we could take a snapchat without other people being in it. He then grabbed me and kissed me, so of course I kissed back. We then exchanged numbers and I went to go leave and he went back to his family.

From that point on we texted a lot, he told me a lot about school and then he started mentioning prom. Now, something you should know about me is, I love being a girl, but I'm not at all girly. I do not look forward to proms or formals or anything where I can't wear pants if I want to. But when he asked me to be his prom date, I didn't hesitate to say yes.

Now, from that point on, all we talked about was prom, and what was going to happen after prom. We named of restaurants and everything. We finally decided we would go out to eat with some other people and probably hang out afterwards. I think we both were thinking of sex, but mentally decided to let the chips fall where they may.

Prom night finally came and lo and behold, it's raining. It literally rained all day. So after prom while we went back to his house to change, the bottom literally fell out. It was storming and everything, so our group just cancelled and we decided to stay inside and watch netflix and order take out.

One thing led to another and instead of watching netflix, it started watching us. We started making out, like most things initiate, then we decided to start groping until finally I was like I want this to go further so I went down on him. He pulled my panties and slid a finger inside my wet pussy.

Now be reminded neither of us were virgins, it's just that I was basically celibate. Sex was not on my brain, but ever since me and him crossed paths it was all that was on my brain.

He slid his finger in and out of me multiple times, earning a soft moan from my lips. I just knew he made a mental note of how tight I was, and for some reason that made me even more horny than I already was. He reached in his wallet and pulled out the condom and slid it on, then he laid me on my bad and slid into me.

That was the most pain I had felt in quite some time, but I didn't tell him cause I didn't want him to stop. I whimpered under him as slowly pulled out and slid back in again. He continued to thrust in and out of my pussy, until the pain went away, and I started to moan loudly. He took that as an invitation to start fucking my brains out, and so he did. I came within the first minute. My pussy had never felt things like this. He continued to fuck me earning moans and making me arch my back when he reached down to kiss me. He then pulled out and said three words.

"Hands and knees"

Now, to be very clear, i'd never had sex in this position but when I played with myself it was always in my fantasy.

I quickly obeyed his request and got on my hands and knees and he took no time getting back into my pussy. I had never come so quickly in my life. He thrusted in and out of my so fast I came like three times back to back.

Since it was our first time together I didn't want to come off as too demanding but I really wanted to swallow his cum. I was to afraid to tell him so I didn't say anything but when he took one last deep thrust inside of me and let out a moan, I knew he was cumming inside the condom inside of me and I came again.

My knees felt weak, when he pulled out of me I completely collapsed. I had never felt something so amazing. I had never had so many orgasms. I watched as he pulled the condom off and threw it away. I put my panties on, and then I had to leave, since my mom hadn't given me permission ahead of time to spend the night. During the ride home, I was so exhausted I fell asleep on his arm.

When he dropped me off, he walked me to my door, and we went inside, after he knew I was safe we kissed goodbye and he left.

But that was just the start of something amazing.