I’ll never forget the first time I felt a hard dick in my tight little asshole.
I’d been dreaming about that cock of his for months. My boss had a certain “reputation” with the ladies, so I was disappointed that during the course of working for him, he had treated me like an employee and nothing more. I finally decided I was going to take matters into my own hands.
As his assistant, I’m usually in his home at all hours, so one day I showed up, in my sexiest lingerie, heels, and just a trench coat over top. I climbed the stairs to his bedroom and peeped inside. I could see the outline of his erection under the white bed sheets.
I stood over the bed, slid the sheet off of his hard cock and as he woke up I opened my trench coat, revealing the lingerie beneath it and as I dropped it to the floor, I told him “fuck me, boss”.
At first he was surprised, but the minute my coat hit the floor I could see his big, fat cock getting harder then ever.
I immediately dropped to my knees and took that big rod of his down my throat, drooling and moaning the whole time, loving every minute of it.
“I always knew you were a big slut” he told me, “could see it in the way your eyes always found my fat cock every time I was giving you instructions. Well now I’m going to instruct you how to take care of this dick”.
“Yes, Sir” I mumbled through the moans of my deep-throating, drool spilling down my face as I spoke.
Suddenly he grabbed me by my hair and told me to get up, and as I did he swung me over the bed and started spanking my ass as he continued to pull my hair “You like that you slut?” he said.
“Yes, sir” I said again, “I want to be your slut, Sir”.
“Oh do you?” he said as he spit on his fingers and shoved them into my asshole.
“Well good sluts can take this big dick in their ass, you think you can handle that?”
I started crying at the thought, both because I had never done something like this before and was afraid it might hurt and also because I wanted to feel his huge, throbbing cock thrusting itself inside me, even if it did hurt.
“Mmm…” He said, “I like those tears, keep it up and you’ll get my dick even harder before it goes inside your tight little asshole”.
Then the next thing I knew I felt a splitting pain from his cock pushing inside of me, but as soon as he started pumping me it started to feel like a raw, intense pleasure.
A kind of pussy wetting pleasure that I knew could only come from giving my body to him, to be his dirty whore.
“I’ve been dreaming about your hard cock inside my asshole for so long, Sir” I cried “I never thought it would feel so good!”
He reached down and grabbed a fistful of my hair again and started pumping into me harder and faster, “what a good girl you are,” he said, “taking my huge cock down to the balls in your virgin asshole, what a good slut you are for me”.
He started smacking my ass again with his hand with every thrust of his dick, hammering it inside of me.
I started crying again it felt so good, “Sir, I’m going to cum with your cock in my asshole, can I please cum for you” I begged.
“You think you earned it?” He said.
“Please, sir, can I please cum with your hard cock pounding inside me, sir”?
“Mmmmm, alright then slut” he said, “show me what a good slut you are taking my big dick in that ass and cumming for me like a good girl”.
I started shaking and crying I was cumming so hard for him. My pussy was dripping all down the sides of my legs with each shudder of orgasm.
Then he pulled out his fat cock from my asshole, and I gasped at the shock of it, he threw me over on the bed and said “now it’s my turn, open wide”.
I knelt in front of him, mouth open, mascara tears streaming down my face from my own pleasure and pain.
“I want to taste you so badly, Sir” I said, “I’ve been waiting so long to taste your hot cum”.
He stood over me, pumping his hard cock onto my tear-stained face as I eagerly lapped at his cum.
I was covered cum as his massive load was in my mouth, and running down my face and onto my tits.
“What a good little whore you are” he said. “ I enjoyed making you cry. Who knew when I hired you that you’d be such a good little anal slut for me, now go clean yourself up”.
Even though that was the day my dream of fucking my boss finally came true, it was really the day that I learned what a good little anal pain slut I am, and I can’t wait to fill this tight little hole again some time soon.