Risky anal. My (f)irst ti(m)e. | 2016

I grew up very sheltered. I had my first kiss, gave my first blow job and fucked a man for the first time, when I was 16...and we weren't very cautious.

This particular night, my boyfriend and I had been having sex for about 2 months. He came over to my moms house, to watch a movie with us. It was late, and my mom, and younger siblings ended up going to bed. My 15 yr old sister and 14 yr old brother were on one couch, and my boyfriend and I on the other under a blanket. We started the movie cuddling, then ended up spooning with him behind me.

He started grinding against me very slowly. I didn't feel comfortable doing anything near my siblings, but, I started getting wet against my better judgement. He started fingering me, and we could both feel how soaked I was. He pulled my pants down to my knees, pushed my thong aside, and started rubbing his cock against my ass.

We had never done any ass play. I knew people did it, I just had never considered it. And definitely wasn't planning on it like this! I could tell my brother had fallen asleep, but my sister was just dozing off. I tried pushing him back, whispered for him to wait. He pushed my legs apart instead, and pushed his dick between them, rubbing against my soaked pussy...I didn't know it, but he was just lubing up.

After he had gotten me even hornier, and I had stopped protesting, he moved back, and started probing my virgin asshole...I'd never had so much as a finger back there.

Nothing happened for a while, just him rocking back and forth gently, and me trying to come to my senses and put an end to it.

Eventually, I relaxed and he felt my ass unclench. As soon as he felt that, he pushed in. As far as he could. He got the head in on the first push, and I clenched back up on him. I had to try so hard not to gasp. It hurt so much. He just rocked back and forth and crooned in my ear about how amazing I was, how good I felt, until I relaxed again, then he ground in more. This went on a few times till he filled me up completely. Then he just grinded inside me until he came. By the time he came, I was getting very into it. I loved feeling his cum fill me up, I think that was the first time he came inside me too.

There really wasn't much movement the whole time, but I still wonder to this day if my sister knew something was going on.