Chapter 1: A Sister's First
Right after my older sister got pregnant I decided to give up my cherry. She was going to get married as soon as they could make the arrangements. I didn't want to get pregnant just yet but I was tired of being alone while helping her sneak her boyfriends into our bedroom at night and then watching her fuck them in the dim light of the street lamp outside the window. I knew she had been fucking several guys, seldom using protection and the boy she was going to marry probably wasn't the father. I also knew with her moving out I would have privacy if I wanted it.
I wanted an experienced guy not like the "also" virgin that popped my sister Lisa's cherry. Lisa told me the story a hundred times. The first time she cried it to me that night but afterwards it got funnier with every retelling.
When the 'I'm ready to lose my cherry' time came Lisa had decided the next guy that got her alone on Flat Top look out, (the towns famous 'make it in the car on Friday night spot') would be the lucky guy.
Unfortunately she picked a kinda dumb hunk that had never really fucked before. She figured with all the girls who dated him because he was a jock a few of them would have let him make a home run. Truth was when a girl gave him a hand job or blow job he would shoot after a couple of pumps or sucks and was finished for the night.
My sister got him to leave the show early and go to Flat Top. She found a nice secluded spot and got him in the back seat. She pulled off her sweater so he could see her nice big tits. She hadn't worn a bra or panties because she wanted him to have one thing on his mind. She pulled up her short skirt, lay back in the seat and spread her legs. Even then she had to tell him what to do.
"Come on Buddy, take off your pants and get your cock out so you can fuck me. You do want to fuck me don't you? I mean it's not every day the head cheerleader lets a guy pop her cherry. You can brag that you fucked me but you better not tell any one it was my first time."
"Duh yeah, um you sure look sexy laying there like that. You gonna play with it a little bit first, You know give me a little mouth action to kinda warm me up?" Always suave Buddy said starting to unzip his zipper.
"No Buddy this is not warm up time! This is fuck time and I want to be fucked. Now hurry up and get that damn zipper undone and get over here so I can put a condom on you. We SURE don't want any little Buddies ruining my cheerleader figure." Lisa said as she watched Buddy fumbling with his zipper.
With his big hands and the small zipper it seemed to take forever and then the zipper jammed. The big lummox had caught his underwear in t.