Dinah Takes Dictation

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

In the 'Men Seeking Women' section of the sex classifieds I found the following: 'Wanted, upscale pretty girl between 20 and 35 for light secretarial work and occasional personal attention. Generous compensation, on call basis.'

On a hunch I texted the supplied number with a reply: 'I may be just what you're looking for. 25, gorgeous dirty blonde, can't type.'

He came back, 'Lol, sounds like an exciting possibility. Send pic?'

I sent a bikini shot. Nothing risqué but self explanatory.

'Oh my,' he texted, 'you're right about the gorgeous part, and the inability to type is a plus! When can you start? I'd like to have you all day Thursday if you're available. You know, regular secretarial hours, 9 to 5.'

He gave the address and spelled out the 'compensation' and it was substantial enough that I said yes. He was clever enough in the ad wording that I had no problem guessing what he wanted. I would be able to figure his financial worth by the time I got to the neighborhood. If it looked risky or felt weird I could always turn around and text him I had other plans.

For my first day at 'work' I picked out a plain white blouse and a very short black skirt that was so tight I'm surprised I still had any circulation to my legs. I pinned my hair up into a makeshift bun and put on the standard black 'fuck me' pumps. I left the blouse open a couple of buttons down to barely reveal the black lace bra I had on underneath. I topped the whole look off with a pair of thick framed glasses and a skinny tie.

It turned out to be a downtown address in a high rise condo building and going up the elevator I was headed right for the penthouse. There was definitely gold in them thar hills! On top of it, the elevator opened to the door of his apartment. He had buzzed me up so he was already standing with the door open when I stepped out of the elevator.

He was good looking, maybe in his early forties with salt and pepper hair and expensive clothes. I extended my hand, "Hi, I'm Miss Smith, your new secretary." He reciprocated with a big smile, took my hand, and "Hi, I'm Mr. Bennett, your new boss."

As he showed me around the apartment he said, "I've got the feeling I've hit the jackpot by hiring you. You're an exquisite woman. It's enough to make me terribly unconcerned about your lack of typing skills. However, you do have other skills I assume..."

"Oh yes," I said, "for instance let's say you were to drop an important paper on the floor." I grabbed a piece of paper off his desk. "Then I would go and retrieve the document for you," and, with my back to him I dropped the paper at my feet. Then I bent over slowly without bending my knees, keeping my sweet rear end upright and prominent, my black panties peeking out and I picked up the paper and handed it to him. "See?" I said teasingly.

"I think I'm going to be dropping a lot of things from now on," he said half laughing, half drooling. "Let me show you to your desk." He led me to a desk just adjacent to his and all that was on it was a telephone, a pad of paper and a pen. "While you're here you can answer my phone and take the occasional dictation. You do know how to take dictation, right?"

Sitting at my desk I said, "Sure I do, come over here and I'll show you." He came and stood in front of me, I swiveled in my chair until I was eye level to his pants, then I unzipped his fly, pulled his dick out and started sucking him until he got hard. Looking up I said, "This is what you mean by dictation, right?"

He could barely make a sentence and just nodded and I went back to sucking his dick and kept at it, taking as much of his shaft as I could handle. When I felt him get close to orgasm I pulled away and said in a sexy voice, "Is that enough dictation or is there more you want to give me?"

He smiled and said, "Ahhhh, ya, that will be all for now."

He zipped up his pants, went over to his desk and was actually making an effort to get something done but he kept looking over at me and I just kept my legs crossed and a naughty little smile on my face. He had written a note with the words I was to use when answering the phone, then I could take a message or, on his signal, turn it over to him.

I took a couple of phone calls and he was writing something on the word processor but he was so ridiculously distracted he couldn't focus on what he was doing. I'd glance over to him and he'd be staring at my legs. I kept mercilessly teasing him, slinking over to the water cooler and bending over to fill the cup. I drank a lot of water that day.

I thought, 'This is what you hired me for and after today you're never going to want another secretary. Hehe.' Once I caught him looking at my blouse so I subtly ran my hand over my breast pretending to adjust the blouse. I heard him breathing audibly. I was eating some crackers and deliberately got some crumbs on my skirt. I stood up to brush them off and kept going over my crotch so seductively he was about to fall out of his chair. He wanted to have my hot bod to lust after all day and I was determined to put on a relentless show.

Eventually he couldn't stand it anymore.

"Miss Smith, could you come here and bring your steno pad?"

"Yes, sir, Mr. Bennett, I'm ready," I said eagerly, pulling up a chair across from him.

"Take a memo: 'Dear Miss Smith, I've been noticing you around the office and have come to the conclusion that I'd like to fuck your brains out. If that's acceptable, please get back to me ASAP because my boner needs attention. Sincerely, Mr. Bennett'

Giggling, I wrote everything down, pretended to read it again and began a reply memo: 'Dear Mr. Bennett, I have noticed you looking at me and, to be honest, it's been getting me hot. I would love to find your cock firmly planted in my juicy pussy. I would suggest that you first have some hors d'oeuvres at my spread. You pick the time. Sincerely, Miss Smith"

I handed him the memo. He laughed, stood up and came around the desk to me. "Miss Smith, please take some more dictation."

I unzipped him again although this time he was already hard and popped out of his underwear. I took his cock in my mouth and really worked it. Then I said, "Would you like to sample my spread?" He picked me up onto the desk, pulled off my black panties, parted my thighs and announced that he'd be taking a quick snack break and then went down on me. "Unnnnnn, ahhhhhh," shit, the orgasm began rolling across my belly. I loved getting paid and getting serviced.

The double entendres were silly but very fun and sexy to play with. We were having as much fun as two consenting adults could have. His snack break turned out not to be so quick and he spent a considerable amount of time applying his tongue to my sweet spot. I easily came twice and was almost delirious after the effort he put to the task. It was so finger fucking good.

He stood up, asked me to place my hands on the giant picture window behind his desk and present my ass to him. As I looked out at the amazing panorama of the cityscape he announced he would be putting his Boss to work in my secretarial pussy. What started gently soon gained momentum, his cock slamming me up against the glass. The view of the city, the risk of being seen and his hard banging brought me to another orgasm. Reaching back he grabbed something off his desk and I soon felt the cold jelly he rubbed on my anus and after that his slow back door entry. I squealed a little but soon got acclimated to his man meat stretching my pink hole. He spent quit a bit of time sodomizing me but then began to enjoy alternating between the two fuck canals. As I learned later this was his favorite perch to fuck his secretaries on. Eventually unable to hold back any longer he gained momentum and exploded into my asshole. "Unnnnnnnnnhhhhh, fuck....fuck....Oh fuck, Miss Smith!!!" Dripping onto his carpet i cupped my rear and made a dash to the bathroom to clean up

I'd given two blowjobs, been fucked hard front and back and creampied in the ass. It was still only 10:30am.

At 11:30 he announced that we'd break for lunch and so we went down the elevator and across the street to a sushi bar where he offered to treat me since I was a 'special' employee. I accepted graciously and then proceeded to torment him (in a good way) by eating the food as sensuously as possible. I looked straight at him with every bite, my tongue lingering on the food, occasionally mimicking fellatio with the chopsticks. It was making him nuts.

He hastily asked for the bill, tossed some cash on the table and rushed me back across the street. I'd like to say we made it all the way in the front door but that was not the case. Two seconds after the door closed, he hiked up my skirt and fucked me in the elevator, a fairly risky move but we got lucky and there were no stops. We were nearly to the penthouse when he, about to blow, stopped short, surely conserving himself for the afternoon.

When we got back to his home office we sat at our respective desks and I, at least, pretended to be doing something meaningful. An hour and a half into my down time, just for fun I called Anna and was telling her about my adventure when Mr. Bennett (still didn't know his first name) came up behind me.

"Excuse me, Miss Smith, but personal calls are not allowed on company time. I'm very disappointed in your behavior and I'm afraid I'll have to take disciplinary action if you want to keep your job. Please say your goodbyes and meet me in the gym."

He had shown me the gym during our walk through and now, apparently, I was being directed there for some sort of punishment. I wasn't quite sure where this was going but played along. This was a big penthouse so it was hard to remember the route but eventually I stumbled upon it. He was there waiting for me with a stern face and a slight smile.

I hadn't seen it the first time around but in the middle of the gym was a padded leather gurney with restraints. Uh-oh. The boss was into BDSM and probably just waiting for an excuse to involve me and he found one.

"If you don't mind, Miss Smith, please strip down."

"Everything?"

"Yes, and then lay face down across the end of the gurney."

I did what he asked and he stripped down as well. Then he secured my wrists and ankles to the gurney so that I was bent over, face down, at a ninety degree angle with my legs about three feet apart. He had a small whip in his hand about the length of a fly swatter, the end of it being a three inch square piece of hard leather. He circled me occasionally snapping the whip in his hand.

"You were a naughty girl and fucked the boss and then broke the rules and made a personal phone call. I don't have a choice...," and he snapped the whip across my bottom and I let out a little yelp. He continued circling me and each time he came around behind he'd snap the whip on my buttocks, thighs or calves. "I'm starting to worry I might have hired a little whore." He stopped and stuck three fingers up my pussy and fucked me while snapping the whip on my ass again. I let out a yip occasionally but there was a weird enjoyment in this. It stung like hell but ended up heightening the level of pleasure and I was close to cumming again.

Each time when he crossed in front I could see his erection coming alive again, getting harder and harder as he got off on dominating and humiliating me. He basically did whatever he wanted. Just to scare me sometimes he'd whack the gurney with the whip close to my head and I'd jump. Other times he'd stop and force his cock roughly into my mouth, pump it a little and move on.

I was wetter and wetter from the punishment until I yelled, "IIIII'mmmmmm fuccccccckkkkiinnnggg cummmiinnggg, uhhhhhhhhhhhhhh..."

"I have to teach my whore..."

As he came behind me he snapped my ass with the whip and then rubbed his cock up and down the length of my crack before thrusting it in me. He grabbed a handful of my hair and really started banging my kitty with the gurney jerking back and forth so hard I thought it was going to break.

This went on for a good fifteen minutes before he stopped, walked away and came back with a large vibrator which he jammed up between my legs. He kept it there until, "Ohhhhhh shit...I'm...I'm.....cummmmmmiiinnnggg, oh fuck!!!" Then he walked around to the front of me again and grabbing my hair once more, pushed his cock down my throat, pumping it some and then he jerked it until, "oh, fuck...uhhhhhhhhhh," he sprayed cum all over my face.

He walked away and left me there for maybe ten minutes, still bound, with cum dripping off my glasses.

He came back with a towel, undid the restraints and cleaned me up as best he could. Then he handed me another bath towel and a robe and showed me to the bathroom where I could shower. Tally as of three o'clock: two blowjobs, fucked me in the window, fucked me in the elevator, whipped me and bondage fucked me in the gym. Secretarial work was harder than I thought. He suggested that I go ahead and keep the robe on.

He noticed I was squirming around so he came over and said, "Miss Smith, I apologize for any extra zeal put forth in your punishment. I hope it was somewhat enjoyable. To try and say thank you, please follow me." We went to his master bedroom ensuite and there he had a hot jetted tub already fired up and removing my robe he helped me into the tub where I went completely limp for the next hour. I'm sure I fell asleep.

It was four when he came to check on me. I woke up with him stroking my hair. "How are you doing?" he asked. "Great. What a treat this was," I said.

"Glad you liked it. I have one more task and then we'll call it a day."

"I figured you might," I said coquettishly.

He took my hand and helped me up, then took complete charge of toweling me off, stopping at points to suck my nipples or stroke my clit. He then dried off my sexy legs, stopping again to eat me. It was all very delicious. Then he guided me to the bed and had me lay back so he could take me to climax. My nails dug into the bedding

That was the task.

After I had put myself back together and gathered my things he walked me to the door.

"That was like the most unbelievable day, Miss Smith," he said with a playful laugh. "I can't tell you how sad I am that it's over. I'm already missing you and your amazing secretarial skills. You're smart, funny, indescribably beautiful with one spectacularly tight pussy. I need you back. Is there any way the temp agency could send you back next Tuesday?"

He kissed me and handed me a wad of cash that far exceeded our original agreement. As I stepped on the elevator I turned and said, "Thank you, I'll have to check my calendar. I'll get back to you." and I blew him a kiss.

As the elevator was sliding closed he stuck his foot in the door and said, "My god, I forgot to ask your first name."

"Dinah. What's yours?"

"Eddie"