"I can't take anymore," I groaned.
"You're almost there, just a little push more and it will be all in your tight cunt," he whispered. I could hear him unzipping himself and knew he would be rock hard. I also knew he was jerking himself off watching me try to take this thing into me.
"Push! Just one more try and it will be there," he urged. I could feel his free hand over mine and before I could blink he pushed his hand down hard and the plug popped into my cunt. I screeched and cried out in blurry pain.
"Baby, you're being very dramatic. Just a few minutes ago I had my entire hand in there and you can't take this tiny little butt plug??"
His hand moved from the plug in my torn pussy to my clit. I was soaked from the lube and my own wetness so his fingers there felt amazing. The harder he rubbed my clit the wetter I seemed to get and more I craved his touch.
"Pull over anywhere, a parking lot whatever, just pull over," Andrew commanded.
The cabbie complied. Andrew grabbed my arm and threw the door open. Spinning me he pushed me over the trunk of the car.
"Come out here and watch if you want. Leave the meter going, don't worry."
The cabbie snuck around the side of the car like at any moment he would be shooed away. Andrew kept telling him to move closer and closer.
"Do you think she's beautiful," he asked.
"Yes, your girlfriend is a very beautiful woman," answered the cabbie.
"You would fuck her wouldn't you?"
"She is very pretty."
"That's not what I asked. I asked if you would fuck her. I saw you watching her with that plug. I bet you're hard now seeing her white ass spread and open. My guess is you'll go home and jerk off thinking about her."
"I would fuck her, yes," the cabbie muttered.
"Here I'll get her started for you," he said pushing my legs apart and sliding his cock right up into my raw ass. Despite the lube, I moaned in pain and total fullness. His cock was big on its own, combined with a huge plug in my cunt it bordered on unbearable...bordered. I found myself pressing back into him taking him deeper and deeper into my ass and with the plug filling my pussy I edged closer and closer to cumming.
Andrew pulled out and motioned to the cabbie.
"Okay, your turn," he said tossing the cabbie a condom.
Andrew came over and leaned down to my eye level.
"You look so pretty spread out for me. I'm going to let this guy make you cum hard I think you deserve it," he said as he stroked my hair. "I'm going to fuck your pretty little mouth while he does it though."
I heard the condom wrapper rustling stop and braced myself for the cabbie's cock. I opened my mouth wide as Andrew stuffed his cock into my mouth and started pumping. I was just getting used to the motion in my mouth when I felt the cabbie press his cock into me. I squealed as my as was forced open yet again. I could tell the cabbie was smaller than Andrew, but I was really tight to begin with and two brutal assaults didn't loosen me up. I howled as the cabbie found his rhythm and Andrew found set his own pace in my mouth. I slid my hand between my legs and started to rub my clit as I got fucked hard from both ends. I panted hard and the cabbie pounded into me pressing the butt plug higher into my cunt and my finger rubbed hard and fast over my clit imagining how another load of cum would taste. I moaned loud and deeply as I came all over the cabbie's cock. This sent him over the edge and he came deep in my ass.
I barely caught my breath as Andrew pulled out of my mouth and took the cabbies place in my ass, unlike the cabbie though he didn't bother with the condom. He pushed his cock into me hard and fast as I begged for more still running on the adrenalin from my own hard orgasm. Pumping into me easily he grabbed my hair and pulled my head back.
"Such a good little slut aren't you," he groaned. "I think I do have a use or two for you and this tight ass."
He barely pumped me three more times before I heard him groan loud and push into me as hard as he could. I felt his cock spasm deep inside me and as I came all over his cock knew there was a huge load filling me up my ass. He half collapsed from the release and I could feel the beat of his heart on my back.
I looked over and saw the cab driver redress and staring wide eyed at us both. Andrew stood himself up, pulled me up and we both dusted ourselves off, redressed and got back into the cab.
"Where do you live," he said as he adjusted his shirt cuff.
"Yonge and Eglinton."
"Let's take the young lady home," he said to the cabbie and without asking I gave him my address.
Turning his attention back to me, "it's a great area. Lots of parks and restaurants aren't there."
"I love the area," I replied.
"You did great tonight. I know you're going to be a little sore tomorrow, I think it was worth it though don't you?"
I really didn't know how to reply.
"Open your legs," he commanded.
I did, but couldn't imagine that he would be even close to ready to go for a third round. He reached between my legs and started to pull the butt plug out, which I had managed to forget about in my own throws of passion so to speak.
"Since you've been a good girl I think you deserve a little treat," he whispered. "Rub your cunt."
As I rubbed my tender clit, Andrew pushed the huge butt plug deep inside me again. My cunt was stretched and full as he fucked me with the plug. I moved my fingers faster and faster in time with his thrusts. I started moaning softly as my entire body started to vibrate closer and closer to the edge.
"That's it baby girl, let Daddy fuck you. You've been such a good girl today," he whispered.
That sent me over the edge. I moaned deep as my body shook with waves and waves of cum. With a swift single motion Andrew pulled the plug from my cunt and instantly I started squirting pulse after pulse of my own cum. My entire body was shaking and shivering in ways I had never felt before.
"Well, I guess we know that you really are a little Daddy's girl," he said with a smile. "You'll be a bit sore tomorrow, but I think you will agree that this was all worth it."
I smiled back not knowing what to say.
"You are on a three month probation, you start Monday," he whispered into my ear. "There will be a courier package sent here for you tomorrow with your wardrobe requirements and your clothing allowance. I expect that you will find every thing on the list and substitutions are not an option. If you cannot find something, text me and I will suggest an alternate."
"Thank you sir you won't regret it," I said feeling a little awkward.
He opened the door for me and reached in to retrieve my bag.
"I've put the make up in your bag for you as well," he said. "I will tell you when, where and how much of it to wear so you must carry it with you at all times."
I nodded my head and put my bag over my shoulder.
"And here," he said handing me the butt plug. "A souvenir of tonight, use it frequently and think of this. And yes, I will ask you if you have."