A Night Alone With My Best Friend - Sex Stories

A Night Alone With My Best Friend

... engaged on the ride we were taking.

As the song started, I sashayed into the living room, swaying my hips, and blowing kisses. I lip synched along with Madonna. I started moving towards him, jiggling my chest, and strutting like a whore. He was loving it, laughing his ass off, and making cat calls at me as I lost myself in the moment. In my mind, I was a girl, and he was looking at me like I was Madonna herself.

“Turn around and shake that ass, baby!” said Kyle, sitting up at full attention on the couch, “Let’s see you make it wiggle!”

I replied, “You would like that, wouldn’t you, daddy?!” and began dancing closer to him, shaking my ass as best I could.

He paused the song, and said, “Hold up! Hold up! I’ll be right back!” and he sprinted out of the room, as I was standing there, horny as fuck. I pulled the lipstick out of my pocket and applied it heavily. Kyle came back into the room waving a fistful of dollar bills and had a shit eating grin on his face. His eyes widened when he saw my frosty pink lips.

“I love your sparkly pink lips, baby!” said Kyle, as he sat back down on the couch attentively, and started the song over again.

I acted annoyed that he was starting the song over again (I wasn’t) and pranced off to the hallway again to make an entrance. As the song began, I started my strut. I walked as sexily as I could directly towards him, swaying my ass. He stood up on the couch, and started waving a dollar bill at me. His robe was barely tied around ...

... the waist, and as he pretended to gyrate, I could see his cock flopping wildly through the silky fabric of the robe.

I blew him a kiss and walked right up to him. He folded the dollar bill up and put it between my lips, which made us both laugh. He quickly sat back down and had a request:

“Turn around, slut! Let me see that ass! Grind on me, sexy bitch!”

I gave him my best attempt at sexy, sissy eyes, turned around, and began walking backwards towards him, swaying my ass from side to side.

“That’s it,” he said, “bring that ass down on daddy’s lap!”

In that moment, I just let go of any remaining inhibition I had, and lowered my ass right down on his crotch and began grinding. I could feel his hard cock right between my cheeks, and I massaged it in a circular motion, while bobbing my ass up, down, and all around him. He put his arms around me and out in front of me, and began showing the dollar bills I had just “earned.”

He said, “That’s right, baby, you deserve this cash! Back that ass up, I’m gonna put it in your underwear!”

I was lost in the moment, trying to act like I was laughing with him, but in reality, I was totally turned on and had excitement butterflies swirling throughout my body, so much so, that I completely forgot that I was wearing his sister’s bra and panties as I ‘backed that ass’ up to meet him at eye level. As I was swaying my ass back and forth in front of his face, he began pulling my pants down, then obviously saw my ass draped in ...