Straight Male / 41
Boarding School Story
My sophomore year at boarding school was great. I wasn’t a ladies man. But I still got girls. One was enough for me. She was a senior. A local girl from town. She had a little size to her in all the right places and a very pretty face. Once we became sexually active with each other school was fun. We lived in a coed dorm. The sneaking around was exciting. With only a few dorm staff it was easy to be alone with her for hours. So much easier to have quickies with her too. She would always wear small shorts without panties when we’d go for a walk. She’d sit on my lap, grind then slide her shorts over and put my dick in her. From afar it looked like she was just sitting on my lap. It was fun with her. It didn’t last. She was a midterm graduate.
The second semester was less fun sex wise fora time. She was gone. I was being loyal to her. Apparently, she wasn’t being loyal to me. There was a girl from her town that kept me updated on her. She was a sophomore too. We became close. Eventually began flirting and then messing around. I still had a girlfriend and the girl had a boyfriend in another dorm. She would sneak to my room at night. We would only lay together and kiss. I didn’t try to fuck yet. But we both gave in one night.
It was a Saturday night. Midnight to be exact. There was a shift change for the dorm staff. Only one guy came on for the midnight shift. He sent everyone to their rooms. A few minutes later he comes into my room and wants me to do something. I go with him and he tells me the girl wants my help with cleaning the kitchen. I say I’ll help her. He says she’s waiting for me in there. He then tells me that he’s going to another dorm to talk to someone. He’ll be gone for a while and to lock the door after we’re done. I say we’ll lock it when we’re done and he leaves.
When I get to the kitchen it’s locked. She lets me in. She shows me what’s she’s cleaned. I follow her to a part that’s hidden from view. We start kissing. Realizing we’re alone and were left alone. I put my hand inside her shorts and immediately finger her. The way she held onto me tightly and the way she moaned while I did it sticks with me to this day. She reaches in my shorts and jerks off. We’re pleasuring each other. It feels amazing. Then I just turn her around and bend her over the counter. I pull her shorts down then mine. I put it in her and fuck her until I cum in her. We go to our rooms after we’re done.
We did a few things afterwards. Even once in a classroom. That’s a good story too. Not long after I had sex with the hottest girl in school. I’ve shared that one here before. Graduation night I spent with my girlfriend and her friends. That’s another story as well. That’s my dazed and confused moment. For anyone that’s seen that movie knows. Graduation can be awesome.
The second semester was less fun sex wise fora time. She was gone. I was being loyal to her. Apparently, she wasn’t being loyal to me. There was a girl from her town that kept me updated on her. She was a sophomore too. We became close. Eventually began flirting and then messing around. I still had a girlfriend and the girl had a boyfriend in another dorm. She would sneak to my room at night. We would only lay together and kiss. I didn’t try to fuck yet. But we both gave in one night.
It was a Saturday night. Midnight to be exact. There was a shift change for the dorm staff. Only one guy came on for the midnight shift. He sent everyone to their rooms. A few minutes later he comes into my room and wants me to do something. I go with him and he tells me the girl wants my help with cleaning the kitchen. I say I’ll help her. He says she’s waiting for me in there. He then tells me that he’s going to another dorm to talk to someone. He’ll be gone for a while and to lock the door after we’re done. I say we’ll lock it when we’re done and he leaves.
When I get to the kitchen it’s locked. She lets me in. She shows me what’s she’s cleaned. I follow her to a part that’s hidden from view. We start kissing. Realizing we’re alone and were left alone. I put my hand inside her shorts and immediately finger her. The way she held onto me tightly and the way she moaned while I did it sticks with me to this day. She reaches in my shorts and jerks off. We’re pleasuring each other. It feels amazing. Then I just turn her around and bend her over the counter. I pull her shorts down then mine. I put it in her and fuck her until I cum in her. We go to our rooms after we’re done.
We did a few things afterwards. Even once in a classroom. That’s a good story too. Not long after I had sex with the hottest girl in school. I’ve shared that one here before. Graduation night I spent with my girlfriend and her friends. That’s another story as well. That’s my dazed and confused moment. For anyone that’s seen that movie knows. Graduation can be awesome.
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