A Date With Sir

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When I was done cumming he pulled his dick out and started stroking it slowly. He bent down and licked my ass. "I hope you're ready for your tight little ass to get filled tonight."

My moment of joy turned into a moment of sheer panic. I know I've wanted this forever, but I'm so scared it's gonna hurt.

He lowered his head again and started teasing my asshole with his tongue. He licked it slowly trying to push his way in, and making sure he was lubing it up very nicely.

He moved his head lower and started working on my pussy. He took his finger and started playing with my asshole, slowly pushing it in a little ways, then taking it out. He then pushed his entire finger into me and let my ass get used to it. Then he pulled it out and slowly worked in two fingers. When he felt like I was relaxed enough he put his cock into my pussy getting as much as my juices as possible on it. He then slowly brought the head of his dick to my ass pushing just the tip in. He sat there for a minute letting my ass get accommodated to the size. He then pushed a little further in.

I screamed into my ball gag. It was the sharpest, most excruciating pain. Seeing as I was tied up and gagged, I couldn't go anywhere and surprisingly, after a minute of him staying still, it didn't hurt so bad anymore, in fact it was starting to feel good.

"OK are you ready?" With that he sunk his cock in my ass, balls deep. I clenched my teeth hard on the gag but it wasn't as bad as my past experiences.

"God your ass is so tight, I'm so glad I'm the one who gets to enjoy this first"

Hearing that made me want to smile. It warmed my heart for a minute, and then he started pumping my ass. Slowly at first, but then he picked up the pace. His breathing became heavier and I could tell he was close to cumming.

"Ok slut I'm going to fill your ass with my cum. I hope you're ready. And you have my permission to cum"

I came instantly at the sound of his words. He slammed his cock deep into me and held himself there.

I could feel his hot cum in my ass, it felt incredible. I can't remember anything I have ever done that felt as good as that did.

He stood there for a few minutes letting his cock soften and fall out of my ass with an spilling a little seed with it. He then took all of my restraints off and the ball gag out of my mouth.

"You did very good kitten" he said.

"Thank you sir, that was amazing."

He then took my face in his hands and kissed me deeply. I closed my eyes and tasted the remnants of my pussy on his lips and in his moustache. I love it when he calls me kitten. And for a while there I felt like I was in another world. He then laid down and I laid next to him and put my head on his chest.

"I'm not done with you yet kitten, but let's take a nap first." I just smiled and drifted off to sleep.

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AnonymousAnonymousover 2 years ago

Okay this had me in the first half

AnonymousAnonymousover 7 years ago
After 13 years

I'm sure he reads this from time to time and reminisces. While the story will never fill the void, it still must bring him some form of comfort and maybe even a smile to live in the "what if", if even just for a second.

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