My Bosses' Halloween Party

Even I couldn't. But I didn't stop trying. Again and again I impaled my throat with it.

"Oh Fuck" Thomas cried out and threw his head back. Spinning and twisting my head as I went, I wanted to be the best cock sucker this glorious dick would ever feel. And I put all the more effort into it with that goal.

He had sat forward, hands down the top of my maid's outfit playing with my tits again when I finally took the whole length down my throat. "Oh fuck!" Thomas said again when his hands flew to the back of my head and he flexed his cock inside me. I sputtered from the move, fighting a choke, and his hands applied more pressure, released some then pressed down again, fucking my face as deeply as he could.

Eventually I truly gagged and had to pop up. He let me. He stared at me breathing heavily.

"Um, thanks. And sorry." He mumbled insincerely.

I shook my head, "No, I'm into you taking control." Then, looking down at my outfit I shrugged coyly, "I'm just the help after all."

Something in his eyes lit up, and suddenly both his hands were in my hair, holding my head firmly as he fucked my face forcefully, slamming it down and pulling it up and slamming it down again. We were well passed the point of glowing in the moment, I was proving myself to a major crush on his beyond glorious cock. I thought he was going to cum, but he pulled me off of him.

"Fuck me you're perfect," he said. My heart melted for him. I blushed and felt awkwardly shy, considering.

He stood, his cock again at eye level, and allowed me the pleasure of tasting it before he pulled me up to a standing position. He reached down and examined his slacks, stained with my juices, and reached under my skirt to feel me. "You cum like a waterfall." He said it very matter of fact. "I'm gonna be fucked explaining these pants. Can you not control it?"

"Not with you I guess," I said, looking at the floor.

"Lets test that."

He took me by the hand and lead me up the stairs and down a hall, and soon was tossing me up on the bed. Jenny's bed. My other boss. He climbed up after me, after taking off my pants, and rolled me onto my stomach. I felt silly still in the cheap maid's outfit with my tits out. It was ripping along the seems from all the man handling and moving. I was very aware how short my skirt was as his hands roamed up my fishnets and over my big dark ass.

He reached over and grabbed Jennys big red pillow and showed it to me. "See this? This is where your boss lays her head to sleep. Sweet loveable Jenny. Do NOT cum on this. There is no way she wont notice. Then he put the pillow between my legs and made me spread myself across it, straddling it, as my pussy literally touching it.

OMG I thought, trying to get off the pillow, but he pinned me down and more swiftly than a man that size has any right doing, he slid his cock deep deep into me. Deeper than most men have gone. Don't cum! My internal voice screamed as he slid further in. The pressure was intense! He fucked me, stroking long and deep into me. "Good God, your pussy feels incredible," he said.

I could feel a bit of dampness on the pillow and I winced. I did not want to face Jenny at work if she saw I came on her pillow. I tried to keep my body up off of it as Thomas kept thrusting in to me, but it was hard to focus on that.

Then he laid on me. He took my arms behind my back and pinned them, putting his weight on my back, and suddenly he started fucking the shit out of me like I had never been fucked before and rarely since. He pounded into me like a jack hammer, and pinned as I was against that pillow I squealed and moaned and panted, whimpered begged and screamed as I came all over it. He stopped fucking, and I didn't have to see the pillow to know I had cum all over it. But he showed me anyway. Laughing, he put it on the bed and shoved my face in it. Hands in my hair ground my face in it.

Fuck I was drunk. And fucked. With work and properly. My body tingled all over.

He hopped up and did something. I heard him rummage around. He came back with handcuffs and a pair of Jennys panties. Expensive looking ones. Wait, he knew where she had handcuffs? Were they sleeping together too?

Soon my hands were cuffed, my heels had fallen off already, so it was easy for Thomas to slide Jenny's panties over my much bigger ass. I was confused, but I was too drunk and dazed to really get what was going on. He put Jenny's other pillow between my legs, with my head still on the cum stained one he stuffed my head into its pillow case. Even my drunk cum coma mind started to think "What the fuck."

Then I heard the click click of his phone's camera from behind me. Fuck. He took pics as I squirmed and flipped trying to hide my pussy, only for my tits to flop around, and my hands were brown so I couldn't cover them.

"What are you doing?!" I yelled, getting my head free of the pillow case. My whole head smelled like my own cum.

"Making memories." He said freely, smiling that smile. Then my head was back in the pillow, my pussy pressed hard into the fresh one, and Thomas pushed Jenny's panties aside as he slit his dick back in to me.

And then he really started fucking me.

The headboard kept slamming against the wall. The whole bed shook. The whole house shook. And spun. My pretty hair was ruined by the wet pillowcase my head was stuffed into. And I started to cum again. And again.

Then he was out of me, and the pillow case was off my head. He rolled me over and showed me the even more ruined pillow in victory. Rolling over made me dizzier than the pillow case had and I fought back a desire to puke. I smiled back at him, trying to act like all this was still ok for my crush. He pulled Jenny's panties off of me, they were beyond wet, and I found myself staring at his huge glistening cock.

"How is it still so hard? So big? How have you not cum yet?" I rambled out drunkenly.

"What do you mean?" he asked. "I came in you twice already." I was too confused to panic. He came IN me?! "Cant you tell?" he asked, and then his dick was in my mouth again. Was I supposed to taste if he came? Clean him off? I didn't know anymore. I just accommodated his magic cock as best I could. Then it was gone and Jenny's wet panties were stuck into my mouth. "Suck these clean too," he commanded. And I did. As I did, he rolled me over and spanked my ass so hard it felt like he hated me. Again and again as I tried to clean my cum.

Then they were gone, and I was on my back, hands still cuffed and now pinned behind me uncomfortably, and he was on top of me again, sliding into me missionary. I had to arch my back to keep my weight off the cuffs which made my boobs stand out ridiculously, he noticed, as he sucked on them and fucked me slowly.

"I just need to cum one more time before I go, is that ok?" he asked, so kind and gently I couldn't even understand the words. Then he started fucking me, faster and faster. Complimenting my hair and my lips and the feel of my pussy and my tits.

"Don't cum in me," I finally managed to gasp out when I sensed him getting close. "I was shocked with how bold I was saying that. It must have been the alcohol and endless orgasms emboldening me.

His hands encircled my throat and my handsome dreamy boss spat on my face.

"Don't tell me what to do," he growled. And then he started fucking me in earnest. My boobs flopping hard enough to give me a concussion if his hands around my throat didn't block them. His gasps as he came couldn't be missed, nor could how I felt him erupt inside of me. I would have felt it if he came before, wouldn't I? Or was I looking for it?

Fuck I was wasted. I just wanted to curl by a toilet and puke. But then he was off of me again, and getting dressed. "Im going to need to go by the 24 hour Walmart and buy some pants." He said, shaking his head. He said it like he was mad but he was smiling that smile. "Then I have to make it downtown and be there long enough to be seen by people and in pictures, so I don't have time to give you a ride home." He put her wet panties into her drawer and put the pillow cases back, stain up. Not that face down would have helped the one. And he uncuffed me, putting those back in the same drawer.

He helped me sit up. Helped me walk into the hall. I was having trouble. "Jenny has a guest room ill tell her you are sleeping in tonight. She wont mind. Do NOT mention how your cum ended up all over the room. If she asks say you don't know what she is talking about. Its more fun that way." He let me flop onto the guest bed, my maid's outfit ripped even more down the side, and I realized all my clothes had been moved to Danielle's car. Fuck.

He brought over a trashcan "in case I puked" and sucked on each of my tits for a bit before he straightened up and just... left. Drove away.

I was asleep in seconds.