Here is a little story about one of my oldest friends. Jon and I grew up together, and we did a lot of experimenting together. I hope you enjoy the story.
Jon and I first met when he changed schools and became one of my classmates in the fifth grade. He was quiet, and kind of shy at first, but he became quite the little extrovert one you got to know him. We became friends almost instantly. And over the next several years we became the best of friends. We never dated, but he was my closest confidant, and I told him things I never told my boyfriends or girlfriends. But there were some things even he didn't know about me. He knew I wasn't a virgin, but that was all I ever let on. He never knew how anti-virginal I was, and he was too good of a guy to never ask.
It wasn't till our junior year in high school that we ever fooled around together. We were at a party and the alcohol was flowing freely. After more than a few drinks we found ourselves in the corner making out and feeling each other up. He didn't know that I would have stripped right there and ridden him if he had wanted, so he led me to a back room and we had ourselves the first of many good times.
Once he realized our friendship wasn't going to end and that I was willing to have sex with him just about any time he wanted, he was alright with the situation.
Jon wasn't a big guy. About 5'9, but he was very athletic. He played shortstop on the school's baseball team, and was quite good at it. He became quite popular at school, and had a long succession of girlfriends. He and I never stopped being friends, and our benefits never ceased. He never told any of his girlfriends about me, but never ceased telling me about what he was doing with them. I had actually had sex a few times with one of his girlfriends. She was bi, but since she never told him, I didn't feel I should either.
We had a lot of fun together those last two years of school. We fucked at least once a week. At school, work, our respective homes, out in public, and just about everywhere else that could be imagined. The sex was really good, and he wanted a lot of it. But that was just fine by me, because I enjoyed it greatly. He didn't have the biggest cock ever, but it was a decent 7 inches, and he was good at using it. And he was just the right amount of rough when fucking me. Hair pulling, ass slapping, back scratching, and the occasional light choking. I loved it.
We even talked about our fantasies a lot too. He wanted the usual guy fantasies. Group sex, threesomes, and especially to fuck girls in the ass. I don't know why I never told him I was into all those things. I think I just enjoyed having him to myself when we were together. I know it would have been fun to include him in everything I was doing, but I never did. He was really into anal though. More than one of his girlfriends let him, but again, I never let him. I just don't know why.
This all leads up to the true beginning of my story. It was May of our senior year. Graduation was just a couple weeks away. My parents were out of town and Jon and I were relaxing after a day long, fuckfest. That was when he dropped a bombshell on me. He told me he had decided to join the Army. I was shocked. I know he had thought about it, but I had tried to convince him otherwise. There were two wars going on at the time, and he was my best friend. I didn't want him going off and getting killed. But it was too late. He had already signed up, and he said that he was going to be leaving just two days after we graduate. After I got over being shocked, I became pissed. I didn't want him to go, and I want happy about his choosing to. So I became queen bitch. I wish I hadn't done it, but I guess I wanted to hurt him into doing what I wanted. I was angry, and I ended up hurting myself more than him.
I avoided him and ignored him for the next couple weeks. But it became impossible on graduation day. Everybody and their families were milling about at school, in and around the auditorium, waiting for everything to start. I was talking to people, congratulating and being congratulated. I felt a hand on my shoulder, and turned around. It was Jon.
"Can we talk?" He asked.
I nodded and we walked off to a more secluded part of the school where there wasn't anybody around.
"I'm sorry about enlisting. I didn't know you would be as upset as you are."
"No. I'm sorry." I said. "I have been a horrible bitch lately. It wasn't fair to you."
"It's alright. You know that I'm going to be alright, right?"
"Yeah."
"Hey! Cheer up ok?" He said.
"I'm so sorry Jon. I'm sorry I was so mean to you."
I was near to tears, but he laughed and gave me a big hug.
"Well I know one way you can make it up to me." He said. And I felt his hands slide down to my ass.
I laughed a little, "You men and your one track minds."
"Hey, I'm going into the army, and who knows when I'll get the chance to fuck a girl as pretty as you again."
I smiled and slowly shook my head.
"Come on." He said, and he took my hand and led me into one of the bathrooms.
He pulled me in and locked the door behind us. I was excited by the fact that we could get caught and there were hundreds of people around the school.
He took his cap off and threw it onto the floor, and pulled his gown over his head and hung it over the stall door.
I took my cap off too, but he told me to put it back on. He wanted to fuck me with my cap and gown still on. I like that kind of kink in a man.
He pushed me down to my knees in front of him. The tile floor hurt my knees, but I knew he just wanted a short blow job before he fucked me, so didn't complain. I unzipped his jeans and pulled them down. His cock was already making a nice tent of his boxers, so I pulled his cock out through the hole in them and greedily sucked it into my mouth. I heard him groan and felt his hand on top of my cap. I could feel his thumb playing with the tassel as he guided my head up and down on his cock.
After just a few minutes he stepped back and told me to get up. He turned me so I faced the mirror above the sink. My cap was crooked so I took the time to straighten it up, and as I did so Jon fell to his knees behind me. I laughed when I heard his knees knock against the floor, causing him to groan. He told me to hold onto the sinks edge, and he pulled me back so I was slightly bent over. He lifted my gown up and flipped it onto my back to reveal my three inch heels and the light dress I was wearing.
"I've always liked this dress." He said.