Life Lesson #2: Freaky People Attract Other Freaky People :)

I was down to my underwear - a basic set of white cotton string bikini panties and a white lace bra. Missy somehow was only in a satin camisole and white knee socks with no panties at all! Missy got on all fours with her ass in the air and I squirted lube on one end of the dildo. I slowly inserted the dildo into Missy’s ass and gradually worked it in and out until it could go at least a third of the way in. I squirted lube on my fingers and pushed them into my ass as far as I could reach to get the lube as far in as I could. I got on all fours with my ass pointing toward Missy’s and inched backward until my ass could just touch Missy’s ass. I pulled the back of my panties down, leaned forward, and placed the top of the dildo in my ass. I slowly leaned back against Missy’s ass and she let out a stream of curse words - “Holy Fucking Shit, Stop!” Apparently, I was not lubed enough and was driving the other end of the dildo deep into Missy’s ass. We reset and this time Missy held the dildo right where it entered her ass and I rocked back and forth driving the dildo in and out of my ass until I was nice and slick. We got a nice little rhythm going, rocking back and forth with our butts pressing together on every back stroke. We were both massaging our own cocks and I could feel the pressure of the dildo against my prostate. Just as I was really getting into it, Missy shouted “What the fuck, Caleb!” and I looked up to see Missy’s 18 year old brother standing over me with his cock in his hand masturbating like crazy. He crouched over me like he was going to sit on me and I felt his warm cum hit my back. Missy and I both got up from all fours and Missy chased Her brother out of the room shouting and cursing all the way. I toweled off to go home and there was more cum on me than I could ever imagine. Basically Missy’s brother had snuck into the basement and had been watching us for a little while. He knew we dressed up and must have liked to watch; but this time he just couldn’t take it anymore. He left a huge pool of cum on my back and some in my hair.