Dinah Takes Dictation Ch. 02

(These are the further adventures of Dinah, a full time escort. While not generally presented in series form, to find out how she got started read 'Dinah Might')

With my day job at Ariana's Fantasyland in place I still had reasonable freedom as to when and how much I worked. We were technically independent contractors so if Anna and I had a job together we could both opt out of our day jobs for the afternoon if necessary.

It had been three weeks since my first visit to Eddie Bennett, the business dude who had hired me for the day as his 'acting' secretary. Operating out of his penthouse we had complete privacy to role play all day long while he made a hopeless effort to get real work done. He spent way more time tending to me than his business and I flirted and teased my way through the day but that's what he hired me for.

He texted:

'Once again I need a competent secretary with absolutely no typing skills to pretty up the office and make me bone up on my work. Interested?'

I liked working for him the first time and wouldn't hesitate to return but after running it by Anna last time I wondered if I should pitch both of us, Dinah and Anna, the dirty duo. I decided to at least give it a try since it was always easier to go on a fucking spree with backup.

I texted back:

'Would love to help you get a little more 'behind' in your work. Hehe. Just wondering, considering your load, if you might be interested in two secretaries. My partner in crime, I mentioned earlier in a text, has only one downside, I think she truly knows how to type. It would be worth the extra expense, believe me.'

'Double the cost?'

'Yes, but consider it one of the best write-offs you ever had.'

There was a pause and then he texted, 'It sounds too good to pass up. And if I wear out I can always call in a business associate to help share the work space. Thursday at 9am good for you?'

'Absolutely perfect. See you there, and do us all a favor and make sure, if you do bring somebody in off the bench, he's 'clean' cut.'

That was my not so subtle request but he came back quickly with, 'I'll make sure he's clean as a whistle, that is if I need him. The thought of managing both of you provides a happy challenge.'

I then texted Anna who said, yes, right away. 'What should I wear?'

'Just think secretarial, with the tightest skirt and the highest heels you can handle. Oh, and wear glasses. Underwear is at your discretion. Your name is Miss Johnson. I'll pick you up at 8:30.'

Two days later we were on our way to Eddie's penthouse office and I gave her the abbreviated version of what he liked, what we'd done last time and what to expect.

I parked the car in the building garage in a private space he set up for me and then we took the elevator to his door. When the door opened and he saw both of us I thought he was going to have a coronary and fall over before we even got started.

"Holy shit, that temp agency is really getting good! Please come in girls. Hello, Miss Smith, nice to have you back, and who is this stunning stenographer?"

"Mr. Bennett, this is Miss Johnson." Anna extended her hand and they shook. Anna had gone all sexytary: gray blazer, black skirt ridding up to unsafe booty levels, royal blue blouse unbuttoned halfway down, black patent leather stiletto heels and black thick framed glasses. With Anna's blonde tresses to top it off, she was a horny boss's dream.

Last time I did the blazer but this time I went with a more than form fitting canary yellow pencil dress, so tight even my perky little 32Bs were ready to bust out. It was the way my legs came out of the bottom of that dress that had Eddie salivating. I intentionally left some stray blonde hairs askew to give me that freshly fucked look. I wore round tortoise shell glasses and midnight blue fuck me pumps to complete the ensemble. If your dick was active this is the office you wanted to be in.

Two hot blondes just waiting to be fucked.

The look on Eddie's face was like he just won the lottery. Then that was followed up by a look of concern, 'Can I handle both of these women?' He guided us over to the office and where there was once I single desk there were now two facing one another. Each had a telephone and an answering script similar to the one I read from before. We sat down and Eddie went to his own desk up on the riser, his back against that incredible bank of floor to ceiling windows, looking out over the city.

Shockingly, even though he had two prime pussies at his disposal he actually did work although it's hard to tell how much because he was constantly looking at us and we were flirting like mad trying to see how long he could last.

"Excuse me, Miss Johnson, would you mind bringing me a cup of coffee?"

"Yes, sir, right away," she said, on her way to the machine. "Will you be creaming it yourself or should I bring one?" When she set the cup in front of him she purred, "Is there anything else I can do for you, Mr. Bennett?" When she said it she leaned forward to give him an eye load of cleavage and his gaze went straight for it.

"I don't think so. Oh wait, I dropped a paper clip on the floor and can't find it, could you take a look? Your eyes are surely better than mine."

Anna got on her hands and knees pretending to look for the pen, every so often running her hand along his thigh and glancing off his cock. Of course, I could see the entire thing because his desk was made of clear lucite. I watched her stroke his crotch and eventually unzip his pants and pull out his excited cock as she went kamikaze on him. He fell back in his chair. Anna was a master cocksucker. I know that sounds derogatory but she was so good at giving head that they just came back for more and more.

Her skill at deepthroating sent him into another zone. It wasn't necessary but he kept grabbing the back of her head and forcing her head down on him. He didn't need to because she was already taking him all the way. She didn't stop him though, figuring, I assume, that he enjoyed the control factor. He was so clearly out of his skull that I started to feel a little jealous of her prowess.

Then surprisingly he commanded me: "Miss Smith, I need you up here now!"

I went quickly up to him, he pulled his dick out of Anna mine's mouth, stood up, took me by the hand and placed the palms of my hands on the huge window facing the city. This was his favorite move.

"Just look at the beautiful view," he said poetically. I think he might have been referring to my ass. With his pants down to the floor he hiked up my dress, ripped down my panties and fucked the daylights out of me. Anna's super blowjob let loose the maniac in him and he was banging my rear so hard I pictured myself flying out the window. When he was about to come he pulled out, turned towards Anna and said, "Take a memo, Miss Johnson" and jerked his cum all over her gorgeous face.

"Oh my god, did that really just happen?" he said as he straightened up his clothes and sat back down with a satisfied look on his face. "Thank you Miss Johnson and Miss Smith, that will be all for now."

Anna and I went off to the bathroom to 'freshen up'. I had to help Anna with cleanup since the cum was everywhere; in her hair, on her glasses, on her blouse and, obviously, her makeup would have to be reapplied.

"That was round one," I said to Anna, "this guy has the stamina of a team of horses. Remember, he fucked me to climax four times last visit."

"I wonder how long it will take him to call in backup," she said. "I have the feeling he's not the wasteful type and that includes pussy. At some point, with two girls to satisfy, he's going to ask for help since he probably wants the most out of his investment."

As usual, Anna was right on the money and around 10:45 in walks another suit, tall and handsome, definitely younger than Eddie.

"Miss Smith, Miss Johnson, this is Mr. Hampton. He works for me at another location and I asked him here so that he could enjoy what fine secretaries you both are. Michael's own secretary is on vacation so I thought there was no sense being selfish when I have two. Mr. Hampton, I think I'm going to offer you a choice as to who you'd like to work with first."

Mr. Hampton looked at us like he was buying a new car. He asked us both to stand up and he walked around us and stared at the goods and finally said, "I'll work closely with Miss Smith if you don't mind."

"Great," said Mr. Bennett, "and perhaps we do a swap later this afternoon so we can get a 'broader' experience. Why don't you two use my other office in the den and then we can all go to lunch at Soro's down the block."

"Wonderful," said Hampton, "Miss Smith, after you?

After having been here before I sort of remembered where the den was and lead the way. I glanced back a couple times and he was seriously checking out my profile. Question in my head: will he try to fuck me before we get to the den?

He brought with him a briefcase and the perception of work. The surprise was that when we got there he really had work in the briefcase! He pulled out two stacks of paper and asked me to make copies. I had next to no familiarity with this particular machine but I figured it out. He sat behind the desk, locked in on my ass. I looked over shoulder, smiling. You could take one look at him rubbing his crotch and see that it wouldn't be long before he was humping me. This felt like one of those nature shows where the predator takes an inordinately long time sizing up his prey. I just kept copying.

All of a sudden he was right behind me and his hand reached under my dress and planted firmly between my legs. It wouldn't take a detective to realize that I was wearing crotchless panties. His middle finger found the valuables immediately and pushed up and into my hole while his left hand reached around and pulled down the front of my dress, my lovely tits popping out for him. He massaged my clit and tits while I got progressively wetter. I reached back and felt his raging boner. What did he do, stuff a pair of socks in there?

He lifted me up on the glass of the copier and ate me, making my already wet pussy even wetter, my hand accidentally hit the copy button a couple of times and the bright fluorescent light flowing under my ass while he licked me was a wild feeling.

He was ready. I was way ready.

The only unknown left was how he wanted to serve me up.

He picked me up and carried me to the leather couch. Taking his clothes off completely he took mine off as well and sat on the couch and told me to mount up. Now Anna always told me to be prepared for the unexpected and Mr. Hampton was packing the unexpected; one of those freakishly oversized boners you see in nearly every porn movie. Of course, to see one of these things in person your first thought is 'He's going to fuck me with that?'

I did as he requested but it was like shoving a baseball bat up my vagina. I always had a pretty tight pussy so this would stretch the possibilities.

I eased down and rode him while he caressed my breasts and occasionally played with my nipples. Grinding on him I caught myself quickly coming close to orgasm. What put me over the top was when he put his forefinger between my clit and his body so I kept rolling over it. Taking hold of the back of my neck he drew me closer and kissed me deeply. I came intensely, "Ohhhhhh...uhhhhhnnnnnnnn...fuck me...oh god..."

From what Anna and I understood, most girls in this business avoided kissing but Anna told me she never understood why they wanted to depersonalize something so pleasurable, so both of us went all the way with it. It made guys nuts for you.

"My turn, girl," and he laid me on my back on the couch and put both hands around my neck and rammed my pussy for a few minutes or so, stopping only to withdraw and shoot his cum on my chest. "Ahhhhhh..I'm cummmming...oh fuck, Miss Smith...uhhnnn." He stayed there for a second to admire his handy work and then got up and handed me a wad of tissues from the desk.

"Well, Miss Smith, I think we did a lot of good work today."

"I hope my assistance was adequate, sir."

After we got dressed he walked over to the copier, took one of the ass shots to the desk and asked me to autograph it so he'd have something to remember me by. I signed: 'Mmmmmmm. I hope to see you in your dreams. Love, Miss Smith XOXO'

When we came back to Mr. Bennett's office he was back at it, blasting Anna with his signature move while she faced out to the skyline, the vista of the city as a backdrop for his lascivious travelogue. If any voyeur with a telescope were the least bit curious they would have a nice show at their disposal as Anna's tits slapped against the window.

Mr. Hampton and I sat down and watched them for a bit until he got up, kissed me on the cheek and whispered in my ear, "Gotta get back to the other office. You were lovely. Hope to see you again." He walked out and left me as the sole voyeur. I must admit watching them got me a little turned on. Finally, Eddie shot his load partially on Anna's back and partially on the window.

***

Very matter of factly he pulled on his pants and said, "I feel fantastic. Let's do lunch!"

Anna got dressed and we all hopped into the elevator, Anna and I still with our sex-hair. Nobody seemed to care although the hostess that seated us at the restaurant seemed to know Eddie and from the look on her face I'm sure she surmised what we were there for.

"Say, love, when does your shift end?" he said to the hostess. "Two thirty, why do you ask?" she replied. Looking at Anna and I he turned back to her and said, "Just doing an extra bit of work at my office and thought you might want to make a few shekels helping us."

I looked at Anna and she looked back at me with that WTF look in her eyes. We said nothing and the hostess said, "Sure, that sounds great. See you then."

Then we both simultaneously stared down Eddie.

"What? Just thought I'd throw something extra into the mix...what?" We still stared at him. "Okay, yes, I've fucked her before and since I invited a couple of other associates over today I figured it wouldn't hurt to make it a party."

"Pardon me, Mr. Bennett," said Anna, "but for a good reason we like to know all the players before we play. We let the one this morning slide but you're rapidly changing the game. We're here to make your wet dreams come true but there has to be rules."

"Girls, there's absolutely nothing to worry about. All of these people play a very clean game and I'll personally vouch for them. My associates would turn down the invite if they thought there would be a hint of a problem because they know I'd fire them on the spot. I pay too well for them to risk it. To put a monetary value on my guarantee, and because I'm having a great day thanks to you two, I'm going to sweeten you're fees by a thousand apiece."

We were stunned. We looked at each other and gave the silent ascent and then Anna said, "That's very generous of you and we appreciate it but what about the girl?" "Don't worry about her," he assured us, "I've been nailing that little Taylor for two years now. I would know."

And little she was. Unlike petite Anna and I, Taylor took petite to a whole new level. She was four feet something, a little spinner with dirty blonde hair and an attractive, banging rear end. Then I said, "Okay, we'll take you at your word. Now since we're still your able and talented secretaries I'd like the lobster salad and a martini and, Miss Johnson, what would you like?"

***

On our way back to the office we had a surreal conversation prompted by Eddie's question: "What are some of the wildest kinky things you girls have ever done?" I told him the story of the 'living fuck dolls' party we did not too long ago. The two of us detailed the hottest parts of the evening pretending to be sex dolls that partygoers could use on a whim.

Eddie was almost speechless. "Holy fuck, I wish I could have been there for that," was all he kept saying. By the time we got to the elevator Eddie was so jacked up from our retelling that, risking discovery, he had both of us suck his cock going up in the car.

When we finally got inside his place the first thing he said was, "I wanna host a party like that! We'll build the whole thing around you girls and go all night!"

"Sure, Mr. Bennett, we'll do that soon," said Anna. "Would you like us to generate a memo to that effect?"

"Yes," he said, "leave me a note and we'll come up with a theme and set up an invite list. You know, you girls are better than some actual secretaries I've had. Hehe. Way better."

Then, being frisky funny, she got right in his face, put her hand on his crotch, saying, "Oh, and if you'd like Miss Smith or I to take some of the boss's dictation, your wish is our command. We'll be wet and ready."

Eddie went back to his desk and continued working but Anna and I kept playfully peppering him with sexy memos. Things like: 'Fuck me, it's Secretary's Day!', 'We took a 'pole' of the secretarial pool and you were voted boss we'd most like to have in a three-way!', 'Pussy snack available between my thighs at break time. Xoxo, Miss Smith', 'It's a pleasure working 'under' you! Love, Miss Johnson.'

This goofy shit went on for quite some time and he would laugh sometimes or look at us in that way. He must have had something important to do or he would have tossed it all out the window for another round with us. We waited and teased him some more until a knock at the door. "Could you get that, Miss Smith?"

It was the hostess from the restaurant, Taylor, and she'd done a quick transformation from there to the penthouse. Her thick, curly dirty blonde had been set free from its bun and now hung down to well over her ass. Her makeup had changed and she went from conservative restaurant gear to hottie fashion. That calf length grey skirt had magically receded into a mini that barely covered her treasure. On such a small girl with such a well-rounded rear it had the effect of putting up a billboard with an arrow that said, 'Fuck me here'.

"It's Taylor, sir."

"Oh great, let her in!" And she worked it from the doorway to his desk where she came around and planted a big juicy kiss on the boss. There was lots of history here and so she put on a mini-show for, us, the perceived threat to her sideline income. He likely bought her clothes, gave her spending money and whatever else a twenty or twenty-one year old girl might want from a fifty plus man in exchange for 'privileges'.

What happened next was so unexpectedly weird that I was starting to have doubts about the whole setup. It seems there was no planned foursome in the works. Because that might have made more sense. Nope.

"Look, baby doll," he said, "I asked you to stop by and do sort of an internship. One difference being I'll pay for your time."

She brightened up for the paid part but not so much for the next part.

"These girls you met," he continued, "are experts at satisfying men and so I'd like you to watch them work their magic for the rest of the day."

To say she was visibly crushed would be an understatement. To say we were surprised would be putting it mildly. I couldn't quite decipher what Anna was thinking but I was wondering how in the hell did we end up as mentors for a restaurant hostess aspiring to be a courtesan?

Not knowing when to stop talking, he continued on, "If we're going to make this arrangement work, and I know we will, there's lots more you can learn. Okay?"

The poor girl's ego was severely stepped on but she tried to put a good face on it. "Ya, sure, I'll watch and learn." "That's my girl," he said.

"Miss Johnson, my friends will be here in a few minutes and I hope that you and the lovely Miss Smith will entertain them accordingly."

"Yes, Mr. Bennett."

And almost immediately there was a knock at the door. Anna welcomed them in, three well put together guys who looked like they hit the jackpot when they saw us. Things quickly broke into two groups of three and suddenly Anna was handling two guys and I had another plus Eddie up at his desk.