"We can stop this at any time, you just have to say the word. I should warn you though, that my ideal candidate should be able to take anything I want her to. Right now, I want my fist in you." Tears started running out the side of my eyes as his entire hand pressed into me harder.
"That's a good girl, just a little more baby girl and you'll be there," he breathed as he pushed further into me. "Such a good little girl; showing me that you can take this you are going a long way to prove you deserve this job."
I cried out as his hand slipped all the way into me. He slid his hand further into me as I panted in a half pain and half pleasure induced haze.
"Fuck! Your tight little pussy took it all."
I could feel his free hand stroking his cock against my leg and the image of this handsome guy with my future in one hand and cock in the other sent me over the edge. My hips bucked as his hand pumped my pussy hard as I slid closer and closer to cumming all over his hand. Suddenly he pulled his hand out of my soaked cunt and pushed his fingers into my mouth.
"Clean them off," he breathed as his cock slipped into my bruised wet hole. I screeched as my pussy was stretched wide all over again and lapped at his fingers. I still hadn't seen his cock knew it had to be a good size if my aching pussy felt like it was being torn all over again. My head could barely keep track of what was happening and I tried to focus on licking his fingers clean of all my wetness.
Without warning he reached for a large binder and jammed it under my tummy. He pulled his now wet cock out of my pussy and started to work it into my ass. I groaned in pain as his wide cock pushed further in. I tried to distract myself from the pain by focusing on cleaning and sucking his lean fingers.
"Aww, baby girl, just a little more. You can take a little more in that tight little ass can't you? I'm sure you can even do it quietly without all the whimpering and sobbing."
I took a solid clean breath and tried not to make a sound. He groaned as he cock slid in and out of my tight tender ass. At regular intervals I could hear and feel him spit onto my ass to help his cock slide even further in. I panted and concentrated on my job of licking his palm, fingers and hand. I could smell and feel the stickiness of my pussy juice and spit all over my face.
"Such a good little girl, I bet you want to cum don't you."
Silently, I nodded my head.
"You don't think it is fair that you cum first though do you?"
"No sir, I will come when you tell me to," I breathed. I wanted to give myself to this guy -- I wanted him to control me. The thought of him controlling when and if I came made me even that much more turned on.
"Such a pretty girl with your makeup all runny and smeared because you fucked the boss in your interview," he groaned as he pumped deeper and deeper into me. "The only thing that would be prettier is my cum all over those pink lips."
With that he pulled out of my ass and brought his cock up into my line of vision. It was a thick easy 8" cock obviously hard and seemed to get bigger as he stroked. Without being asked I opened my mouth wide and looked up at him try to read the look on his face. Our eyes locked and he started to groan deeply and faster pumping his cock with his hand even harder. I felt the ribbons of cum stream across my face in huge wet spasms. I licked at the cum that gushed into my mouth and licked my lips to get the drops from there too. When Andrew ran his fingers through the strings on my cheeks I lapped at his fingers with my eager tongue and felt a pang of disappointment when he pulled his fingers away from my mouth.
Silently he unlocked my restraints and I moved to sit myself up.
"Oh we're not done yet my baby girl. I have a few more things in mind before I send you on your way."
I groaned and my belly tightened with excitement at the prospect of another round of proving my unquestioning compliance to my potential boss's needs. As much as I ached, my mind raced with notions of what he could have planned next.
"Give me your hand," he said.
I held out my hand, he grabbed it and pulled me up. The entire room smelled of sweaty sex, it made the air heavy and heady. I felt almost drunk from the thrill of giving myself to a virtual stranger. I watched him as he opened one of the drawers to his filing cabinet and pulled out a fluffy towel.
"There's a shower stall in the washroom down the hall, second door you can't miss it," he said tossing me the towel. "Take your time, have a shower and get cleaned up. Do you have make-up with you?"
"Yes, the basics a bit of powder and lip gloss," I answered.
He reopened the drawer and pulled out a small black bag.
"This should help," he said handing me the bag. "We're going on a little outing so make yourself up pretty, baby girl."
Without questioning, I headed down the hall and found the shower easily. The bathroom was huge and obviously not used often judging by the sparkling fixtures and slight cleaning product smell. I turned the shower and adjusted the temperature until it was nice and hot. My body ached and the hot water limbered me up again.
I scrubbed myself clean from tip to toe while the smell of the yummy honey soap from the shower filled my nose. I washed off every bit of makeup, cum and sweat from my face knowing full well that a clean face was in all likelihood only temporary. I gingerly washed my raw pussy and ass feeling sure that if anyone would inspect either spot it would be Andrew.
I turned the shower off and grabbed the fluffy towel to dry myself. I opened the door of the bathroom to let some of the steam out. The cold rush of air teased my nipples back to attention. My mind replayed the last two hours in my head as I towel dried my hair and pulled it back into a ponytail. I put on my powder make up and opened up the black bag. It was filled with high end packets of eye shadow, liner and lipstick -- all unopened and all very bright. My overall style was preppy casual -- lip gloss was "dressed up" for me, so I struggled a bit with the black eyeliner and bright green, gold and fuchsia eye shadow. I had a sneaking suspicion that every item in the bag was meant to be opened and used -- so I did, lining my lips and applying deep red lipstick as precisely as I could.
The makeup looked great and as I tidied up the bathroom I admired how the shadow and liner made my already bright blue eyes seem even bluer. I walked back to the office naked to find Andrew redressed and the office clean. There was a tinge of sex smell still lurking, but unless you'd actually been in the room while we were fucking, you would have never known that just a few minutes ago I was strapped to that desk.
"Put the towel in here," he said holding out a cotton laundry bag. "I'm sending your things out for cleaning and have thrown out the stockings. Don't worry, I'll make sure you have plenty of replacement pairs baby girl, they looked amazing on those legs of yours so I'd be a fool not to. Here put this on."
He handed me a folded rectangle of fine mesh and discovered it was actually a tube dress. I slid the dress up over my full hips and then over my tits noticing that it barely covered either. The mesh itself was actually quite opaque, although I was sure there were parts that were less "opaque" than others. I felt very conscious and Andrew could tell as I fidgeted with the hem of the dress.
"Come here baby," he said motioning. "You look very pretty and this is a test. I need my go to girl to be able to do what I ask when I ask without question. You did a marvellous job with the makeup and brilliant first try."
He smoothed out the mesh of my dress and while it still seemed to ride really high on my thighs, it was manageable. Silently he unzipped the black makeup bag and took out the eye shadow. I closed my eyes without question and could feel him dusting the shadow on my eye lids.
"Done," he announced. "Such a pretty girl and so obedient. I think you have a lot of potential."
He slipped elastic out of my hair and tussled my damp hair. He tossed the makeup bag into my messenger bag and looped it over his shoulder with his briefcase. I took that signal that we were on our way and headed down the original hallway. After he closed the door, Andrew reached and grabbed my hand which made me jump a little.
&nb
sp; "What? Can't I hold a pretty girl's hand," he smiled. "I can't have scared you off the job too much you're still here."
I didn't know if I was there still for the job or just to see what was next. He flagged down a cab, tossed in our two bags and held the door open for me as I slid in. Sliding in next to me he bent over and handed the cab driver some bills.
"Drive until I ask you to stop or tell you where we're going. Don't worry about the meter or my girlfriend and don't ask questions. If you can handle that, I'll make it well worth your while."
The driver flicked on the meter and we started driving. We hadn't gone more than two blocks before Andrew leaned into me.
"Close your eyes and don't you dare open them until I give you the word," he whispered.
I obeyed.
"Pull up here on the right, leave the meter on and make sure she doesn't open her eyes. She's very beautiful but sneaky -- tell me if she opens those baby blue eyes, okay."
I'm sure the cabbie though he was nuts, I thought to myself as I heard the car door open and close. I sat there, eyes closed listening to traffic trying to figure out where we were. I decided then and there I would make a really shitty blind person. The car door opened and I could sense his energy even before he sat back down.
"Okay drive," he said. "Did my girl open her eyes?"
"No sir she did not," mumbled the cabbie.
"You didn't bribe the nice man into lying for you did you," he asked.
"No, I sat here with my eyes closed the whole time," I stated, eyes still pressed shut.
"You have such pretty eyes, such a pretty mouth and I bet you make boys do all sorts of things for you," he continued as his hand started up my thigh. "You are a daddies girl aren't you? Would you like to open your eyes my girl?"
"If you wish sir," I whispered.
"Open them then," he said.
I opened my eyes to come face to face with a large and wide butt plug. I edged away as his hand tapped my thighs open. I relented a bit.
"Open them and oh yeah...change of plan," he commanded. "Panties off, give them to our friend in the front seat and do it nicely and politely like a proper lady."
I didn't argue that proper ladies probably didn't take their panties off in moving vehicles and hand them over to a stranger. I did however slide off the panties, fold them into a neat little square and lean forward to the driver.
"I would like you to have these as a token of appreciation for being a very good cab driver," I stated matter of factly.
Confused he accepted the gift and warned us about the camera that was recording everything.
"So it will see you put this in your pussy then, I guess," he said handing me the giant plug.
I whimpered knowing that it wasn't going to be easy to take this into me. Like the good boy scout he probably had been, he pulled out some lube and a small towel from his bag. He squirted the lube onto the plug in my hands and I smeared it all over. I opened my legs wide and started pressing the tip into me. As it got wider it got more and more painful.
"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 g
o 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."
The End.
All Out
"Sharon!" I yelled. "What the fuck?"
Filthy Daddy's Taboo Erotic Sex Stories Page 126