Accidental anal with a virgin
At the time, we had both just turned 18. We were inexperienced and so fucking horny. We always looked for ways to get out of the house to meet somewhere to mess around. We would tell our parents that we were going to stay late after school to catch up on some work. We'd pretend we'd have to go to the library to do some research. We'd ask to go to the park. Any excuse to get us out of the house.
That was only the first obstacle. The tricky part was finding somewhere we could be truly alone for an extended period of time. Because of this, we only ever did stuff above the clothes. A lot of touching, grabbing, fingering, stroking, all while kissing.
She had sent me a text message after sending me nudes all day telling me that she wanted me to take her virginity. She said she was so horny and desperate for it. I told her to find a way to go to the park. Both of us lived at home with our parents and neither of us drove just yet, so the park was as good as we could get on short notice.
She got to the park with a group of friends and met up with my friends near a bench. Everyone knew we were talking so nobody cared when we broke away from the group.
Behind the park is a baseball field. It's only ever used in the spring so it was always empty. We managed to climb the fence, ran through the field, and found our way into one of the dugouts.
It was so perfect. We sat on the bench, kissed, touched, you name it. She grabbed my pants and pulled cock out. She stroked it fast then immediately dropped down to suck on it. She was so enthusiastic. She gagged the first time it hit her throat. We both laughed about it, but then I grabbed the back of her head and shoved her back down.
I pulled her up, bent her over, and pulled down her leggings and panties. I reached between her legs and felt how wet her pussy had gotten. Fuck. I was so horny.
We quickly realized we didn't have a condom. We were too horny and not thinking so it didn't even matter at the time. She just kept asking me to fuck her. I grabbed my cock and lined it up against her pussy. Being so inexperienced, I could not find the opening. I'd reach down and finger her, then try to push my cock in the same place. She was still a virgin. She was so fucking tight.
She kept moaning to fuck her and kept moaning how good it felt, even though I wasn't fully in. She loved having my cock feel around her pussy like this.
I tried to push in and she said "go a little higher." She was bent over and I must've thought her opening was lower than it was. I went a little higher and pushed fucking hard. Fuuuuuck. My dick went inside about half way.
"Awwww fuck!!!!" She yelled, but low in volume because she didn't want anyone to hear us.
I grabbed her hips and began to fuck her from behind. It was way tighter than I imagined. Her ass looked so fucking good from this angle. She kept moaning and moaning. She couldn't quite get any words out.
I kept pushing until the full length of my hard cock was inside of her. Once it was fully in, I reached over to kiss her neck.
With all the strength she had, she managed to moan/whisper, "you're in my fucking asshole!"
"Fuck! Sorry!" I tried to pull out but she reached back and dug her nails into me.
"I didn't tell you to stop, keep fucking me!" She said.
Ugh, I was so horny and so turned on by this. I grabbed her hips and began to fucking pound that tight ass. She braced herself with her arm while her free arm reached between her legs and began to rub her clit.
I was so fucking close to cumming, but I wanted to make it last as long as possible. She kept rubbing her pussy, circling her clit while I fucked her ass from behind. Her breathing got heavier and she fucking finished hard. That's all it took for me to fucking explode inside of her.
I gripped her hips hard as I pumped every last drop of cum inside of her ass. I pulled out ever so slowly and saw my cum dripping out of her. I helped her get her panties back on, then we sat together on the floor against the dugout wall.
"My ass fucking hurts," she said. We both couldn't help but laugh until our sides hurt.