"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 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."
The End.
Katie's New Job
It was just another Friday. Katie sat at the desk near the front door of the gallery, IMing with a "Master wannabe." Bored, she played along with his demands to play with her clit. A little self-pleasure was better than sitting and doing nothing. After a few minutes, Katie looked up and noticed someone heading towards the front door.
> "Customer. Gotta go," she typed with one hand as she pulled the other out of her knickers.
With a courteous smile, Katie greeted the striking, very tanned blonde as she entered the gallery. "Good morning! Welcome to the gallery. How may I help you?"
"Good morning. I'm Cynthia, the new owner. Are you the only employee here?"
"Very good to meet you, Cynthia. I'm Katie, and yes, I'm the only one here."
"Any customers here, Katie?"
"No, afraid not. It's been a very slow day."
"In that case, please lock the door and hang the 'closed' sign on it. When you've finished that, please come to my office. Um, where is my office?"
Katie gave her the directions to the main office and then set about locking up. While she wondered what was about to happen next, she also thought about the tall, very buxom woman she'd just met. She began to fantasize about being forced to undress and then to crawl on her knees to Cynthia as she waited in her chair. She thought about having her hair pulled and being made to lick Cynthia's pussy. When she realized how wet she was getting, she stopped fantasizing and continued on her way to the office.
When Katie arrived in the doorway to the office, she paused to observe the new owner as she bent over the desk sorting through some papers. Cynthia was a little shorter than herself. Although very athletic looking, she had quite large breasts that appeared ready to fall out of the plunging neckline of her black dress. Katie could see the edges of the black bra that prevented that from happening.
Katie knocked softly.
Cynthia looked up, smiled and invited Katie to come in and sit down. "Make yourself comfortable, Katie. I have a few things I want to ask of you."
As Katie took a seat in the chair directly in front of her, Cynthia sat down in the plush leather chair behind the desk.
"I'll get right to the point, Katie. I'm going to be making a lot of changes here at the gallery and I need someone I can count on to help me do all kinds of things. I need someone who is familiar with what's been done in the past and who is willing to help make changes for the future. I need someone who is attentive to my business needs as well as my personal needs. I need a personal assistant and I want you to be that person. Before you say anything, let me say that I've had my eye on you ever since I saw you at the company holiday party. I know what a dedicated worker you are. I know you keep up with the latest styles. And I must say I'm very impressed by you.
I know you're married and have children, so I took the liberty of calling your husband to see if he'd approve of your going on overnight trips with me, often with very little notice. Jamie said that wouldn't be a problem as long as all of your expenses are covered. I assured him that all expenses for any trips you take will be covered, you'll get bonuses, and you'll get a few additions to your wardrobe, too.
Before I get your answer, I want to make it perfectly clear that in addition to arranging meetings, handling papers and other normal business related activities, you'll also be running errands for me and doing other things that may seem menial or maybe even a little humiliating to you. The plus side, though, is that you'll get to meet all of the artists that will be exhibiting work here. You'll go to parties with me. We'll go shopping together. And, if you do everything you're told with enthusiasm, you'll make me happy, you'll make plenty of money, and you can become an integral part of the success of the gallery. Oh, and you'll get a company car. I think you'd look good behind the wheel of a metallic storm red Mercedes SLK300 roadster, but you can pick any color you want. Actually, you can pick whatever car you want that doesn't cost any more than one of those, but I happen to know there's one available at Worrells if you want it.
Oh, my! I'm getting a little ahead of myself. I haven't even gotten your response yet. One more thing! If you accept the job, you'll have to go to Castlemaine with me tonight to speak with a new artist. What do you say?"
Katie was thinking about a new car and wondering what Cynthia meant by "a little humiliating." After remaining silent for several seconds, she asked if she could ask a few questions first.
"Certainly, Katie. Ask whatever you want. I want you to be comfortable with every aspect of the job."
"Well," Katie began, "I don't have a lot of business experience. If I don't know how to do something, I don't want to disappoint you. Are you willing to help when I need it?"
"Not a problem, Katie! In the beginning, you'll be doing a lot of small tasks, going to pick up things for me, and just generally being a companion for me on the trips. As time goes on, I'll give you a little more to do, but not without giving you whatever support you need. Next question."
"You said if I do everything I'm told with enthusiasm, I'd make you happy and make plenty of money. You also mentioned something about doing things I might think are a little humiliating. Can you give me some examples of what that might entail?"
Cynthia laughed before saying, "It's not as bad as you make it sound, Katie! But since you asked, I'll give you an example of what might happen this weekend in Castlemaine. I want to sign an artist who specializes in photorealistic fetish paintings. All of the works I've seen are of her girlfriend in bondage. She says it's her girlfriend, but I swear she's got to be her slave - the things she has to do! Anyway, in some of the paintings, her girlfriend is performing oral sex with another woman, or she's being fucked with a strap-on, or having all sorts of things stuffed into her pussy or arse. Lesley, the artist, says she likes to get new acquaintances to do things to her girlfriend. She then photographs whatever is done and later paints from the photos. It's conceivable that you'd be asked to do something kinky to or with her girlfriend. If you do it and act like you're enjoying it, it could help to get Lesley signed on with our gallery. Does that explain it better?"
"Um, yes, yes it does," replied Katie. "If I accept the job, you said we'll go to Castlemaine tonight. I have no idea what clothes to pack, or even if I have the right clothes to take."
Cynthia interrupted. "If you say you'll take the job, I'll take you shopping right now and buy you everything you'll need for the trip, all the way down to a toothbrush. And don't worry about deciding what kind of car you want. We'll take care of that after we're back. I'll let you drive my car until you get a new one. It's not as sporty as the SLK300, but it does have room for luggage. It's a black, ML350 SUV."
Katie's mind was racing, thinking about a new Merk roadster, free trips, free clothes, making more money, and the possibility of having some kinky fun. "I'd be a fool not to accept the offer," she told Cynthia.
"Great! Fantastic!" shouted Cynthia. "Now let's go shopping so we can be ready to leave early. You call Jamie and tell him the good news. Here, use my phone."
Katie took the phone and called her husband. As she started to explain about the trip she had to take that evening, he interrupted and said he knew all about it. He assured her he'd take care of everything until she returned, wished her a great time and told her to do everything asked of her.
As she was saying her good-byes, Cynthia patted Katie's bum and said, "Come on, girlfriend! We've got shopping to do!" She handed the keys to Katie, grabbed her hand and pulled her towards the door. "I'm so excited about having you as my personal assistant!"
After both were in Cynthia's car, Katie asked, "Where to?"
"I know this boutique that has the perfect clothes for this trip. Take a left out of the car park and go straight until I tell you to turn."
Katie did as she was told, driving carefully so as not to cause any harm to her boss' vehicle. Cynthia talked a lot, telling Katie of her vision for the gallery. Every now and then she'd ask what Katie thought. Mostly, Katie simply agreed without any explanation.
When they arrived at their destination and entered the store, a salesgirl greeted Cynthia by name. Katie was impressed. "Do you shop here often?" she asked.
Laughing, Cynthia said she probably kept them in business. "We need to look at some sexy, slinky dresses. The kind that leave very little to the imagination! You know I want a blac
k one, but for my new assistant, I'm thinking a deep red would be right."
The salesgirl showed them several different styles before Cynthia picked a black one and a red one off the rack. "Come on. Let's go try these on."
To Katie's surprise, Cynthia followed her into the dressing room. She didn't say anything as she started to remove the dress she was wearing.
"You know, Katie," Cynthia said, "There are so many times I wish my breasts were smaller like yours." Cynthia unhooked Katie's bra and pulled it off. With both hands, she gently squeezed Katie's breasts. "Oh, those are perfect! I'll bet Jamie loves to play with them. I don't know why you hide them under a bra. When you're with me, you won't. I want everybody to know what perfect breasts you have - not like these huge things! I have to admit, though, they do get me a lot of attention." Cynthia removed her bra and let her breasts bounce free. "I mean, really," she continued. "They get in the way when I try to use a water fountain. Whenever I have to wear a bikini, I have to get a custom made top to keep them under control. That's one reason I prefer going to clothing optional beaches, but look at the tan lines they cause." Cynthia raised her breasts up to show the pale skin beneath them. "And feel them. Go on, Katie. Give them a squeeze."
Katie blushed a little. She could feel a rush of warmth through her pussy as she cupped her boss' breasts in her hands and fondled them. Even though she was amazed at what she was doing, she kneaded them and eventually gave both nipples a firm squeeze.
Cynthia smiled and pinched Katie's nipples. "Look how pretty your nipples look - perky and hard. Not mine. You really have to torment them to get them to look good." Cynthia demonstrated by pinching, pulling and twisting her nipples until they stood up like Katie's. "Damn! I'm getting horny! I'd better stop or I'll be forcing myself on you soon!" She laughed out loud before telling Katie not to worry.
"When you wear a slinky dress like this, Katie, you can't wear anything underneath it. Let me help you slip off your knickers so we can see how you look in it."
The Rougher Explicit Collection of Stories Box Set Compilation Page 177