Jill the Best Secretary Ch. 02

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Jill learns I'm her boss, the hard way.
5.3k words
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Part 2 of the 6 part series

Updated 01/28/2024
Created 07/28/2022
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hoover789
hoover789
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Jill two

The next morning I woke up feeling better than I have in years, being able to play around with and then fuck a drunk, beautiful twenty-five-year-old blonde with a stunning body, really does wonders for you. The best part is, she's married, so no entrapments or her falling in love; plus I have leverage over her consisting of the photos and video of her in her underwear sucking my cock.

Her phone started ringing, it was her husband again, this time I answered it. I thought I was pretty cool, considering his first words were "Who the hell are you?" I explained I was Jills boss and how she went to lunch with her friend and had too much to drink. So I had offered to drive her home and she must have dropped the phone in my car. I didn't find it until this morning and was in the process of returning it. He apologized and thanked me profusely. I told him I was glad to help out and added Jill was upset about something all week, maybe that's what the drinking at lunch was all about. I loved getting a few "digs" in him about his going away. He stammered something about their anniversary and asked me to have her call him as soon as she got her phone. I said,

"No problem and I would be leaving soon."

When I got to Jill's, it was just what I expected from her, she opened the inside door and kept the storm door locked,

"I never want to see or talk to you again after how you took advantage of me last night."

I almost didn't recognize her dressed in sweats, no makeup and I can only guess she had just finished throwing up, judging from her pale complexion.

Whatever color that was in her face drained out quickly when she saw her phone in my hand.

"Can I come in for a minute I just talked with your husband."

"Where was my phone? I've been going crazy looking for it and what could you have said to him?" she demanded.

"Sit down I'll explain everything,"

I told her about finding the phone and explaining to her husband my version of what happened. I told her she could go with the lie or tell him what really happened, but she had to call him now. She grabbed her phone glaring at me and gestured toward the door, then turned to her phone. I think Jill thought that I was going to leave, but instead I went into the kitchen. I could hear her clearly; thank god she went with my version. What a fool her husband was, he actually believed her story and took some of the blame, for leaving her alone on their anniversary . The call was short as her battery was going dead. When it was over, Jill called out to me that I should leave right now, as I walked into the living room, she looked at me and said,

"Thank you for covering for me, but as far as work is concerned, I think it would be better if I quit, don't you think so?"

"I think that would be bad, it would make your husband suspicious, you have a job you like and then all of a sudden you up and quit, for no apparent reason."

Jill reluctantly agreed,

"You're probably right, but I can't talk to you right now; I want you to leave, I have to think about this, plus I'm getting sick. I promise to call you later, I want to resolve this today."

What could I do, I left thinking I would never hear from her again. I couldn't complain, I was getting hard thinking about her passed out on her bed that beautiful face covered with my cum. I went back to my place to transfer the video and photos to my computer.

True to her word, but still surprising to me, Jill called late in the afternoon, she had rationalized what had happened, in her mind we were both drunk and got out of control, so we were both responsible.

The adult thing to do was to put it in the past and never talk about it again. I agreed just to keep her from quitting, I offered to give her a ride to get her car at the office, she accepted and said she would be waiting for me. I pulled up to her house and their she was, dressed in jeans and a bulky sweatshirt, and running shoes., At least she had makeup on ,her hair was in a ponytail tucked under a baseball cap, my dick barely twitched.

Jill got in with that smile on her face, but she wasn't as cheery as she usually was, it probably was just the hangover I hoped. The fifteen-minute ride seemed like hours as very few words were spoken. I dropped her by her car and said see you Monday, she just smiled and closed the door. Her husband wasn't due home till Sunday night. It was only four o'clock Saturday, I couldn't wait till Monday morning to see what I could get away with.

I had a few drinks and called Jill about eight o'clock I was surprised when she answered.

"What's up Mr. Bennet?"

she sounded like her sweet old self, which made me feel guilty, for a couple of minutes anyway.

"Could I see you tonight, at my place or yours, its important."

She replied sounding wary, "Tell me what it is first, and I'll decide where."

"I wanted you to see the video and photos from last night, they're quite good, you photograph well, and I don't know what to do with them. Maybe I should delete them or send them to your husband or maybe your parents? Why don't you come over and help me decide?"

I was waiting for her to hang up on me. But there was dead silence, then I heard her sigh and start to sob,

"You bastard, I can't believe you're doing this to me, I thought we had settled this, now you want more, it figures, you pig. Just give me time to get dressed, I'll be over in an hour."

"Just for that "pig" remark, wear something sexy we may have to negotiate, and you better have something to give up."

"What if I just call my husband and tell him the truth?"

"Yea, that's a good idea, I'll make some popcorn and I'll invite him over and we can watch the video together," I laughed. " I'll be waiting" and hung up. I wondered if she remembered when she wished all men were like me, I'll bet she doesn't now.

I should have insisted she wear her corset and stockings, but that would have been pushing it.

As it was, she didn't do bad, a black skirt that barely came down to her knees, sheer black pantyhose and a tight blue knit sweater that was a little revealing, show casing those over ripe tits and of course black heels.

Her expression was a mix of hate and fear, perfect for my plans.

"What do I have to do to get the video and pictures back?" tears were starting to form in her eyes.

"Don't cry Jill, it's not that bad, I figure if you can put up with my needs for a month, then it won't look so suspicious if you quit. I would prefer you stay, but it doesn't matter, and then I'll give you the pictures, video, everything."

She cocked her eyebrow, wiping a tear away,

"What sort of needs?"

"Simple to start out with, like when you come in the morning, if it's just you and me maybe I'll want to play with your tits, or hiking your skirt up to look at your ass while you work , that sort of thing."

"But what if somebody finds out?"

"If we're careful, nobody will know."

She started crying openly,

"You don't know what a mess I'm in."

"If my husband ever finds out what we did, I'm done." She paused for a minute.

"I shouldn't tell you this, you'll laugh at me when I tell you. Everybody told me not to, but I did it anyway, I signed a pre-nup, he will divorce me in a second."

"The way it reads if I commit adultery, I get nothing."

Talk about dumb, and what leverage I had now. Before I knew that, I was going to keep it simple, some stripping and maybe a blow job, but now there was no limit.

My mind was racing, thinking of ways and things I could do to that body, especially those soft tits, which were now heaving from her crying.

She was sobbing and shaking from head to toe, all she kept saying was her married life was over.

I got up and made her a martini, I didn't think she would take it, but she did and downed half of it, coughing a little bit. I tried to reassure her that nobody else knew or would know what happened and if we could work something out between us it would be over in a month. Jill started to calm down, she was obviously trying to figure something out.

I told her we could work out the details later, maybe tomorrow and not to worry. Now, I thought it was time to have some fun at her bodies expense.

She started to regain her composure, finishing her drink she looked at me with those sad doe eyes,'

"I hope your right, maybe this will work out somehow, but I really have to go now, I'll call you in the morning."

Things were moving too fast, all of a sudden, she was giving orders, I had to let her know who was boss. She should have offered me something as thanks for giving her husband that bullshit excuse. It was time to get this started.

"Don't you think you owe me something for fooling your husband, you're the one that stands to lose everything, not me."

Her mouth flew open,

"You want me to do something tonight? After the day I had trying to get your stuff out of my eyes and hair, you're not only a pig, but you're out of your mind!"

I just smiled, "Everything's in my computer ready to be sent, so you decide."

The tears started again; she was going to dehydrate herself at this rate.

"What do you want, I'll try to do it, just remember I still don't feel so good."

Her head hung down she couldn't look me in the eye.

"For starters stand up and let me look at you."

"Didn't you see enough last night; I woke up this morning practically naked."

"Jill, I would never get tired of looking at you, now take your skirt off, and get rid of your top while you're at it."

"This is so wrong; this is not something a married woman should be doing."

I felt bad for a few seconds, but then I wanted to degrade her some more, you know to keep her in her place.

She slowly took her top off revealing a lacy blue bra that showed her full tits perfectly. Next came the skirt, it was tight, and she struggled with it, setting up quite a boob show. Jill stood before me in just her sheer pantyhose and overflowing bra, nervously shifting from foot to foot in her spike heels, ready to do what I wanted. I was like a kid in a candy store. I didn't want to ask for too much too soon, it might make her go to her husband and ask for mercy saying it was rape.

"I'll keep it simple, come over here and stand in front of me, that's good, now turn around and bend over."

She obeyed; her ass was right in front of me her black hose stretched to its limit across her ass showing her black panties. I reached between her knees and stroked her legs moving upward, she stiffened at first but as I got higher, she slowly parted her legs giving me access to her sweet mound. She groaned, as I started rubbing her cunt, whether it felt good, or she was embarrassed, I didn't know and guess what, I didn't care either way. I kept it up and if she was enjoying it, she didn't let me know.

Finally in a whisper she said, "Are you through yet, it's not doing much for me."

I smacked her ass hard for saying that; she jumped and cried "Stop that it hurts!"

"Don't tell me you've never been spanked?"

"No, not even my father."

"That will change soon enough Jill."

I gave her another good slap and she jumped , rubbing her ass.

"Turn around so I can see your tits."

As she turned, I realized her boobs were almost out of her bra from bending down, why not have some fun I thought.

"Shake those tits Jill," she frowned and slowly shook her shoulders causing her tits to sway and wobble, just about out of her blue lace bra, I gave them a playful slap, and she cried out

"No more, I don't like that."

"Tough, you need some discipline."

As I smacked her tits again, this time a little harder.

She cried "I'll do anything you want just stop hitting me."

She tried to cover herself, but I moved her hands

and pulled her bra down, her perfect tits sprang free. I held them together and started kissing and sucking on her distended nipples. She was starting to tremble and moved her hands to the back of my head. I swear she was getting turned on. I stopped abruptly, she said,

"What's wrong?"

I didn't say anything, j just wanted to let her know I could do what I wanted. I let go of her and said,

"You can put your bra back on."

"That's enough for tonight. Jill, tell you what, you can come over tomorrow, and we will talk about your new duties." "Now come here and give me a kiss."

Hanging her head, she whispered

"Where"

I couldn't help but laugh,

"On my lips, but its good you were thinking."

The kiss was gentle, and our tongues probed tenderly, then her mouth sagged open, giving my tongue full access to hers, she moved her hands up, and held my head tightly. She was a good kisser and both of us were responding by pressing our bodies together.

Finally she broke off panting and out of breath, still holding me closely.

She said softly "Let's not get something started we'll be sorry for."

But it still took a few minutes for her to release my head

That's an odd way for a happily married woman to act; it got me to wondering. I was fully ready for her to fight a kiss on the lips, that's more intimate than a blowjob, for most women.

"Now let me get dressed," Mr. Bennet "I'll see you in the morning."

I watched her get dressed, the best part was her wiggling into that tight skirt, her heaving boobs stealing the show. After fixing her hair she gave me a quick kiss on the cheek and said, "We will figure this out."

I was confused, for all purposes I had raped her while she was drunk, lied to her husband, and extorted her to have sex with me and could ruin her marriage with one key stroke of my computer. What was interesting was she almost sounded happy about facing more abuse. This was the last way I expected her to be, it sort of took the fun out of it. The least I wanted was her begging on her knees to do anything I wanted. For some reason it seemed she was expecting to be punished, and was not worried about it.

I started making plans for Sunday.

I told her to be over at ten in the morning, she had no problem with that, she was in fact a little too eager, how she was going to be dressed would tell me a lot.

Ten o'clock the next morning my doorbell rang. Jill was standing there with that winning smile, she looked beautiful. She had on a wraparound tartan plaid kilt, a white sleeveless sweater, sheer brown pantyhose and brown pumps, complete with ankle straps. The kilt ended well above her knees exposing her perfect legs.

"You like?" she said twirling around. Her bras contents jiggling as she stopped suddenly, the bra was clearly visible and her tit flesh overflowing the straining cups trying to break free, she had to realize how desirable she looked. Jill had just the right amount of makeup on, and hoop earrings, All I could say was,

"You look gorgeous,"

I was mesmerized, and she knew it. Then I realized what she was doing. She may or may not have liked what went on Friday night, but I got the feeling she was trying to get control of the situation, using her body to keep me from thinking straight.

" I love this outfit especially the shoes, don't you?"

As she lifted and cocked one leg, balancing on one foot.

"Yes, they're very nice,"

I was starting to feel like she was doing me a favor, this was going to change.

"You look warm, why don't you take your top off, Jill?"

The smile disappeared,

"So this is how it's going to be, no fore play, no small talk, you just ordering me around like a hooker? You didn't even offer me a cup of coffee."

Unbelievable, I was supposed to have the upper hand and now I was feeling guilty.

Her phone ringing slowed down my feeling of anger and amazement. It was her husband, now it was my chance, she motioned for me to give her some privacy, instead I unzipped my pants and pulled my semi hard dick out.

Her eyes went wide as she answered. She was sitting on the edge of the couch, I quickly sat down beside her; Jill turned and glared at me and started to stand up, I grabbed the edge of her skirt and started pulling it. As she fell backwards her skirt opened wide exposing her legs to her waist. She struggled to get her skirt back, but I kept pulling it up as high as I could, all the while she was trying to talk with her husband. She finally told him to hang on. She hissed at me, "What are you trying to do? he knows somethings going on, now leave me alone!"

"Take your skirt off or I'll shout your name, so he can hear."

Jill face flushed a brilliant shade of crimson as she stood up and unfastened her skirt and let it drop to the floor. She carefully stepped out of the kilt, looking fantastic in her sheer to the waist panty hose and tiny red thong. It was a dream come true, on seeing Jill standing in the middle of my living room with her skirt off, trying to sound normal talking with her husband. She turned to look at me stroking my growing dick, I motioned for her to sit by me. She hesitated for a minute and then gave in. As soon as she was sitting, I took her free hand and wrapped it around my dick, starting to move it up and down. I felt sorry for Jill as her eyes were starting to tear up again. But my dick overruled me, and I kept making her jerk me off. When I was hard enough, I stood up, her small hand falling off my dick. I stood in front of her rubbing pre cum on her face and ear, while she tried to talk innocently to her husband about where she was going shopping. Finally her trembling was making it impossible to keep up with her conversation. Jill told her husband the someone was "coming," which was pretty close to the truth, and to call her later.

Jill cast her eyes down and whispered,

"What do you want me to do?"

She was beginning to break.

"Jerk me off for a while, till I decide where to cum."

She flinched; she wasn't used to being told what to do. Between her beautiful body and face, she had always called the shots; probably due to weak men she had dated.

"Please don't get any of your stuff on my sweater."

I smiled and said,

"You better take it off, I can't make any promises, unless you want to swallow." She winced,

"My stomachs not up to that, do you want to do it on my boobs?"

She didn't wait for an answer and pulled her top off, her oversized tits almost bounced free of her demi bra. Jill grabbed my dick and went back to stroking it.

"Put it in your mouth, get it nice and wet." As I poked at her lips. She glared and said,

"I know what you are trying for and I'm not going to give you a blow job, I don't feel like it."

"And give me some warning, I don't want any of your jizz on my face or in my mouth, understand?"

I don't know who she was used to talking to ,but I wasn't going to stand for it.

She had a triumphant look on her face like she won. That was going to change.

I grabbed her head and forced my dick in her mouth, "It needs to be wetter,"

She grumbled and said,

" Ok ,but no accidents, and stop being so rough!"

I forced my cock past those perfect pink lips feeling her tongue darting over the end of my dick. Jill was a good cocksucker, but the added bonus was the fact she was starting to cry, big tears were rolling down that face. I tried to control myself, but it felt so good. I gave up trying, after a few minutes I exploded, the first shot went straight down her throat, she pulled my twitching cock out coughing and spitting, as two streams hit her face and hair. She was gagging and choking, and really mad.

"You bastard, I told you not to shoot it in my mouth and you did it anyway."

I stood over her my dick in my hand.

"You're going to learn I'm in control, young lady." As I smeared my cum around her face with my dick.

She got a terrible look on her face and pushed past me running for the bathroom, just making it before throwing up in the toilet.

The door was open, and she was kneeling on the floor, dry heaving. I almost felt sorry for her. But she looked so sexy in her heels and pantyhose with her tits almost out of her flimsy bra. I should have taken a picture of her.

hoover789
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