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Who's The Boss? | analplay | 6

 

The moment she felt my cock press against her asshole, Margaret began screaming into her gag and thrashing her ass around, trying to get away. Of course, there wasn’t much she could do, being all tied up. She only managed to arouse me even more. I held on tight to her ass cheeks and pressed her against the corner of the desk, keeping her from moving too much.

Then I repositioned my cock at her asshole and, without warning, rammed my hips forward. There was just enough lubrication to allow me to pop right inside her virgin ass. The lube, however, didn’t help Margaret with the feeling of being spread so wide for the first time in her life. For me, the feeling was exquisite. I had never before felt anything so tight and velvety soft before. Her ass gripped my cock like a vise, milking it for its cum.

As my cock slid balls deep into her ass, and my pelvis slammed against her ass, Margaret opened her eyes wide and froze. It tool a moment for the pain to reach her brain, but when it did she started screaming into the gag and bucking around on the desk. I just held on tight and enjoyed the ride. The handcuffs prevented her from moving enough to expel my cock from her ass, so all she managed to do was increase the stimulation and make it more painful for herself.

I pulled back and started sawing in and out of Margaret’s ass. Her body shook and trembled with pain, but I just kept on going. I had given her the chance to take it slow, but she decided to fight instead. I wasn’t going to show her any mercy after that.

I continued to fuck Margaret’s asshole, until she slowly calmed down and became somewhat accustomed to the sensation. That was when I pulled all the way out, allowed her anus to constrict back to its normal size, and then rammed it in again. This brought all the pain back to Margaret, and I did that over and over again.

I leaned over her and reached around her chest, grabbing on to her little titties. I clamped down on her nipples, pinching hard as I fucked her ass. This caused her to buck again, slowly bringing me to the edge of orgasm. I started thrusting even harder now, slamming her painfully into the desk with each thrust. I pulled her against me by her nipples with each thrust. Her ass was clenching and unclenching in pain, caressing my cock, bringing me closer.

Finally I felt the cum rising in my balls. I pushed all the way inside her, my balls slapping against her pussy, as my cock exploded in orgasm. I deposited spurt after spurt of cum in Margaret’s recently virgin anus, until my softening cock dropped from her ass with a plop.

I grabbed the video camera and took some closeups of my cum dribbling out of Margaret’s ass, as she sobbed quietly into her gag. Then I walked around to the other side of the desk and pulled the gag out of her mouth, leaving the blindfold in place. I squeezed her cheeks, and shoved my cock into her mouth, ordering her to clean me.

Margaret did her best not to gag as she sucked my cock, which now tasted of cum and ass. When she was done I put away the camera and unlocked her cuffs, pulling the blindfold off last. Margaret squinted in the light, and crumpled to the floor. She curled up and just kept rubbing her sore ass.

“Well, Margaret,” I said to her, “that was a good start. Go home and get a good night’s sleep- we’ll continue this tomorrow. Unless, that is, you want me to give those papers to Bill.”

Margaret looked up at me with hatred in her eyes, but she didn’t say a word. She just gathered up her clothes, got dressed, and walked out of the office.

 

What happens the next day?

 
 
 

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