Straight Male / 20
I cheated on my girlfriend and lost my virginity to a controlling slut in high school.
This was all 3-4 years ago, during my junior year in high school.
Thanks to a previous relationship with her best friend, I was left with this girl who obsessed over me. She had no friends because she was super hostile to everyone. She had only had one boyfriend, he was a total piece of garbage. Hit her, fought with her, and left her constantly, threatening to kill himself if she didn't take him back. They were both like that. He eventually got her pregnant and they planned to run away together. Obviously, being in fuckin' high school, that didn't happened. She got an abortion and they were more on-and-off than ever until he moved away.
I had just gotten a new girlfriend, but this girl, B, was still obsessing over me. She would do shit like threaten to cut herself if I didn't say I loved her. It was a fucking mess of a situation.
Eventually, she found out I had a serious thing for anal and my girlfriend was a bit of a prude. B offered herself to me, anything I wanted. If I didn't meet her after school, she said she would hurt my girlfriend. I didn't want to meet with B, but I felt I had no choice.
After school one day, B and I snuck off to a stairwell on the far side of the school. She assured me that it was the most private spot in the school. I trusted her and we set our stuff down.
The inner animal awoke in me and I lunged forward, pinning B to the wall. I kissed her as hard as I could. My cock was throbbing hard in my jeans as I pressed up against her. I reached under her shirt and pulled her bra out of the way. I squeezed those big C-cups and played with her nipples. I pulled her shirt up and sucked on her pink nipples, rolling them between my teeth every now and then.
I reached down and undid her jeans. I started fingering B as I kept sucking on her tits. Eventually I got impatient and dropped to my knees. I tugged her jeans and panties down and tried eating her out. She couldn't spread her legs too much because her jeans were around her knees, so I licked at her clit and tried putting my tongue in her. I couldn't reach her pussy, so I spun her around and spread her asscheeks. I went to town on her asshole, pushing my tongue inside and exploring. I tongue-fucked her asshole as I squeezed her pale asscheeks, letting go every few seconds so they'd squish against my face.
After a minute or so, I got back up and whipped out my dick. She hated sucking dick, but she would still do it. She wanted me to sit down and look away because she didn't want to be stared at with a cock in her mouth. I was eager so I did what she wanted. She sat down next to me and stuck her gum in the corner we were sitting in. Then she leaned over and started blowing me.
God DAMN did she know how to suck cock. It felt incredible. She had some buck teeth, and they scr**ed me a little, but the way she worked her tongue made me fucking melt. She was bobbing and licking and stroking my shaft and fuck, it felt so good. For someone who hated sucking dick, she was a fucking pro at it. I had to force myself to not cum. God damn, I wanted to fuck her mouth forever.
After a while, she was done. She stood back up, pulled her pants and panties back down, and bent over. I got up and lined up my cock to her pussy. I grabbed her hips and pulled her back onto me. My cock slid between her pussy lips and I got my cherry popped. I went balls deep, letting her feel all of me. Then I started fucking her with long, slow thrusts. It felt amazing. I pumped her pussy slowly for a few minutes before she told me to grab her sides hard and pound her hard and fast. I didn't have a condom on, so I was a bit scared to, but I managed to fuck her harder. Her ass slapped against my hips, making it echo through the empty stairwell. I was scared a janitor or a teacher would hear us, but I couldn't stop myself. I fucked B harder and faster, almost clawing her sides as I felt my cum start to boil up and I let her know.
B said I could cum in her ass since we had no condoms. I pulled out and starting licking her asshole again, making sure she was lubed up. I rubbed my cock on her asshole and asked if she was ready. She said yes and I pushed forward. She was tight, but she relaxed enough for my cock to enter her ass. I felt the head pop through her o-ring and I nearly came right there. Fuck, it was even better than I imagined. I went slow, pushing the rest of my cock into her asshole, stopping to make sure she was okay. She grunted and groaned a few times, but she said she was fine.
I grabbed B's hips again and started fucking her ass slowly. Feeling her tight asshole sliding along my cock was heaven. I stopped and held her ass against my hips and told her to clench for me. She squeezed her asshole around the base of my cock and I started fucking her again. She was clenching every few seconds and I couldn't hold it back anymore. I started fucking her asshole faster and faster, my balls flying up and smacking her wet little pussy. I thrust in and shot my cum deep in her ass as she clenched on me. I moved my hips little by little, milking every drop of my load into her asshole. It was the best feeling I had ever had in my life.
When I was totally spent, I pulled out. She let out a little wet fart and I giggled like an idiot as she told me to shut up. She got composed and I clung to her with post-orgasm affection, but she wouldn't kiss me because the last thing my mouth was on was her asshole. She did hug me for the longest time, we felt out hearts pound against each other. We checked the time and left.
This went on every week for a good 2-3 months. I hate to admit it, but I loved fucking B behind my girlfriend's back. I would walk her to her bus, go fuck B, then get home and text her like nothing happened.
A few months later, I dumped my girlfriend and dated B. She wasn't as into me by that point, so I guess it was too little, too late. The sex was amazing though.
Sometimes, I feel like an asshole, but sometimes, I just want to be balls deep in B's.
This was all 3-4 years ago, during my junior year in high school.
Thanks to a previous relationship with her best friend, I was left with this girl who obsessed over me. She had no friends because she was super hostile to everyone. She had only had one boyfriend, he was a total piece of garbage. Hit her, fought with her, and left her constantly, threatening to kill himself if she didn't take him back. They were both like that. He eventually got her pregnant and they planned to run away together. Obviously, being in fuckin' high school, that didn't happened. She got an abortion and they were more on-and-off than ever until he moved away.
I had just gotten a new girlfriend, but this girl, B, was still obsessing over me. She would do shit like threaten to cut herself if I didn't say I loved her. It was a fucking mess of a situation.
Eventually, she found out I had a serious thing for anal and my girlfriend was a bit of a prude. B offered herself to me, anything I wanted. If I didn't meet her after school, she said she would hurt my girlfriend. I didn't want to meet with B, but I felt I had no choice.
After school one day, B and I snuck off to a stairwell on the far side of the school. She assured me that it was the most private spot in the school. I trusted her and we set our stuff down.
The inner animal awoke in me and I lunged forward, pinning B to the wall. I kissed her as hard as I could. My cock was throbbing hard in my jeans as I pressed up against her. I reached under her shirt and pulled her bra out of the way. I squeezed those big C-cups and played with her nipples. I pulled her shirt up and sucked on her pink nipples, rolling them between my teeth every now and then.
I reached down and undid her jeans. I started fingering B as I kept sucking on her tits. Eventually I got impatient and dropped to my knees. I tugged her jeans and panties down and tried eating her out. She couldn't spread her legs too much because her jeans were around her knees, so I licked at her clit and tried putting my tongue in her. I couldn't reach her pussy, so I spun her around and spread her asscheeks. I went to town on her asshole, pushing my tongue inside and exploring. I tongue-fucked her asshole as I squeezed her pale asscheeks, letting go every few seconds so they'd squish against my face.
After a minute or so, I got back up and whipped out my dick. She hated sucking dick, but she would still do it. She wanted me to sit down and look away because she didn't want to be stared at with a cock in her mouth. I was eager so I did what she wanted. She sat down next to me and stuck her gum in the corner we were sitting in. Then she leaned over and started blowing me.
God DAMN did she know how to suck cock. It felt incredible. She had some buck teeth, and they scr**ed me a little, but the way she worked her tongue made me fucking melt. She was bobbing and licking and stroking my shaft and fuck, it felt so good. For someone who hated sucking dick, she was a fucking pro at it. I had to force myself to not cum. God damn, I wanted to fuck her mouth forever.
After a while, she was done. She stood back up, pulled her pants and panties back down, and bent over. I got up and lined up my cock to her pussy. I grabbed her hips and pulled her back onto me. My cock slid between her pussy lips and I got my cherry popped. I went balls deep, letting her feel all of me. Then I started fucking her with long, slow thrusts. It felt amazing. I pumped her pussy slowly for a few minutes before she told me to grab her sides hard and pound her hard and fast. I didn't have a condom on, so I was a bit scared to, but I managed to fuck her harder. Her ass slapped against my hips, making it echo through the empty stairwell. I was scared a janitor or a teacher would hear us, but I couldn't stop myself. I fucked B harder and faster, almost clawing her sides as I felt my cum start to boil up and I let her know.
B said I could cum in her ass since we had no condoms. I pulled out and starting licking her asshole again, making sure she was lubed up. I rubbed my cock on her asshole and asked if she was ready. She said yes and I pushed forward. She was tight, but she relaxed enough for my cock to enter her ass. I felt the head pop through her o-ring and I nearly came right there. Fuck, it was even better than I imagined. I went slow, pushing the rest of my cock into her asshole, stopping to make sure she was okay. She grunted and groaned a few times, but she said she was fine.
I grabbed B's hips again and started fucking her ass slowly. Feeling her tight asshole sliding along my cock was heaven. I stopped and held her ass against my hips and told her to clench for me. She squeezed her asshole around the base of my cock and I started fucking her again. She was clenching every few seconds and I couldn't hold it back anymore. I started fucking her asshole faster and faster, my balls flying up and smacking her wet little pussy. I thrust in and shot my cum deep in her ass as she clenched on me. I moved my hips little by little, milking every drop of my load into her asshole. It was the best feeling I had ever had in my life.
When I was totally spent, I pulled out. She let out a little wet fart and I giggled like an idiot as she told me to shut up. She got composed and I clung to her with post-orgasm affection, but she wouldn't kiss me because the last thing my mouth was on was her asshole. She did hug me for the longest time, we felt out hearts pound against each other. We checked the time and left.
This went on every week for a good 2-3 months. I hate to admit it, but I loved fucking B behind my girlfriend's back. I would walk her to her bus, go fuck B, then get home and text her like nothing happened.
A few months later, I dumped my girlfriend and dated B. She wasn't as into me by that point, so I guess it was too little, too late. The sex was amazing though.
Sometimes, I feel like an asshole, but sometimes, I just want to be balls deep in B's.
- That's Juicy! 10
- Remove It! 0


