I took her virginity and used all three of her holes

I had a girlfriend right out of high school. She was 18 but was still a senior in high school. I must have been 19. She had strict parents, but I was able to hang out with her by pretending to be her tutor. We’d be left alone upstairs and if her younger sister was gone, we'd be able to fool around. I was always anxious about getting caught, but she got off on the idea. I took my role as her tutor a little seriously and when we were trying to study, she'd often try to get my cock out and suck it.

She was a virgin and had the tightest pussy. I was only able to get one finger inside when I tried fingering her. She had an interest in anal and so I'd finger her asshole too, which I found hot. Her asshole was more accommodating than her pussy. I could probably fit 3 fingers in there.

We got really risky one time while upstairs "studying" and she begged me to fuck her. It was spur of the moment, so I didn't have a condom. I really didn't want to get her pregnant and was scared to fuck her raw. But I tried anyways. There was no way my big dick was fitting inside her pussy. She suggested I put it in her ass, and so I spit on my dick more and stuck it in. She loved it.

One weekend we finally got some time alone. Her parents went out of town and took her sister with her. I had prior engagements on Friday but came over that Saturday morning. That Friday night she walked to a sex store and bought a dildo with the intention of stretching out her pussy. She spent a good portion of the night fucking herself and sending me videos.

I know this part isn't sexy but that Saturday was nice. We kind of got to play house. She made me coffee and eggs. Truly she was the kind of girl who wanted to take care of her partner. After breakfast she dragged me upstairs to her room and begged me to fuck her.

She took my pants down and my hard dick popped out. She immediately took it in her mouth and slobbered all over it. That's not what she brought me up here for though. She wanted me to fuck her. She was wearing a big T-shirt and some panties. She laid back on the bed, pulled down her underwear, and didn't even bother taking off her shirt before beckoning me over.

This time I brought condoms, so I took the rest of my clothes off, and put one on. I tapped my dick on the outside of her pussy, rubbed it, and teased her. She was so fucking wet. I pressed my dick into her slowly. She was so fucking tight. She winced a bit, so I checked in with her. She said she was fine and to keep going. So I forced myself into her further- about halfway, before pulling it out slightly and pushing back in.

I worked my dick in and out, every stroke going further in and eventually I was able to make full strokes in and out. She begged me to go faster and so I picked up pace. Eventually I was fucking her as hard as I could. She was screaming out! She started to cum on my dick- I could feel her pussy contract on me, practically pushing me out. I rolled her over and climbed on top, assuming the “prone bone” position. I kept fucking her pussy like that until I was ready to cum. I really can’t cum with a condom on, and so I took the condom off, covered my cock with my spit, and stuck it in her ass. She loved it! I fucked her in the ass for a little while until I couldn't handle it anymore and then forced myself all the way into her ass and came inside her. She pushed the cum out of her ass as I watched in bliss.