Jill the Best Secretary

My name is Bob Bennet, I work for a large insurance company, the main office is in Hartford Conn. While I run a small field office in New York. I had three male agents and one secretary. Who was leaving to have her baby. It was my job to hire her replacement, so to say I was looking forward to it was an understatement.

One application immediately popped out from the rest.

It included a photograph of the applicant, Jill Watson, she obviously thought it was a good idea, and so did I.

It was a picture of her from the waist up. she had a white blouse on that was filled out to capacity by her thrusting tits; her face was sweet with full, pouting lips and just the right amount of makeup. Couple that with black round framed glasses, a perfect smile and blonde hair that framed her face perfectly.

I couldn't wait to see the rest of her. I emailed her and set up an interview, for the next day.

Jill was one interview I was looking forward too.

I was careful to arrange the chair that she would be sitting on, positioning it so as to give me the best view of her legs.

She was a little early, so I told her to take a seat. While I got ready. She perched on the edge of her seat, nervously tugging at the hem of her short dress.

I called her and she came in all smiles and had a confident air about herself,I liked her immediately.

She was overqualified, but since I had the power to set her pay, within reason. I knew I wasn't going to let her go.

She certainly was dressed to impress. Was I ever glad I had moved the chair?

She had on a black form fitting dress that came a couple inches above her knees, with off black nylons and four-inch pumps. The dress had a high neck, but there was still no way of hiding those juicy tits. They were almost too big for her body, which was otherwise petite. I would find out later they were thirty-two d's. What a catch this was for me, a dirty old man.

When I finished, I asked her if she had any questions?

She did, it was all the usual stuff about benefits, vacation and sick days and more. I gave her a packet with all the answers. Then she had one more, the dress code.

Months ago, I had found a dress code from the sixties in one of the closets, and had kept it just for laughs. It stated women are required to wear dresses or skirts with stockings and heels. Try and imagine getting away with that now.

I gave it to her,she read it, I was waiting for a laugh. She must have seen nothing wrong with it and said no problem, she was planning to do that anyway. This was great, good looking and gullible.

I told her she could start immediately. She flashed a brilliant smile, and said you won't be sorry.

As I watched her wiggle out of my office and started setting up her desk, in the process displaying her long legs in sheer black nylons.

I knew already I wouldn't be sorry.

More than once, Jill came back to my office with a question, she was unmindful how her ample chest bounced and swayed walking on those heels. She was the perfect secretary.

I looked forward to every morning; I got there a few minutes early and positioned myself to see her get out of her car. She was one of those girls that took a few minutes to get out of a car.

She usually opened her door, then had to check her makeup and hair. Before swinging her legs out, tugging at her short skirt as she stood up. The best show would be when she would get out of the car with her skirt almost up to her crotch, checking her nylons before pulling the wayward skirt back into place. The only thing better would be if she had stockings on instead of pantyhose.

Who could have guessed then what was going to happen?

Time flew by, Jill was out of the companies probationary period. I was able to give her a small raise without anyone knowing.

We had become close; we sat together for coffee breaks and lunch every day. My wife died five years ago. I was lonely and it was nice talking with her.

Plus, she was a pleasure to look at. Jill had taken to wearing sleeveless tops, my favorites were light weight wool tops, which she seemed to wear a lot. She had to know how she looked in them, and must have been happy with it.

The white one she had on today was so tight; every detail of her over filled bra cups was visible. On days she wore those tops I made up reasons to call her to my desk just to see her walk toward me. Jill had perfect posture; always with her shoulders back, with those magnificent tits jiggling and swaying side to side. All the time with that winning smile. I was starting to wonder what that cute face would look like with my cum all over it. That's the stuff dreams are made of.

Something was wrong at home ; she was starting to complain how much her husband was working. He was a partner at one of those local law firms. I had never met him, always taking for granted he was her age. Not so, it turns out he was in his late forties. So, she married an older man, which was a very interesting fact.

Later she asked to leave early on Friday it was their anniversary, and they were going out to dinner.

I said yes of course.

On Wednesday, Jill came in without a smile on her face, and barely said good morning. From being married that look meant only one thing, trouble at home.

At lunch we were alone in the break room, when she confided in me. Her husband had to go away for business the whole weekend. She was crushed, she had a special night planned.

I felt sorry for her. But at the same time, I was trying to make this benefit me. She wasn't her usual self. And I didn't push it.

After lunch she asked if she could use the company phone, for a personal call, as her cell was dead. I said of course, take all the time you want. Jill stood up and gave me a kiss on the cheek. With those perfect tits dangling in front of my face.

" Thank you, I wish all men were like you."

No, you don't, I thought as I smiled to myself and imagined those tits naked swinging free. Begging to be mauled.

One of the great things about our company phones I could listen to both sides of a conversation on my computer, without either party knowing. She called one of her friends, she was past the crying stage, now she was resigned to being alone. I closed my door, so she could talk freely. About fifteen minutes later, Jill knocked on the door letting me know she was done.

I started trying to look busy. Then I replayed the recording. First the usual girl stuff, then the bombshell. Jill told her she had bought a new black cocktail dress for their anniversary, but the kicker was that the sales lady had talked her into buying a corset and regular stockings as a surprise for her husband. The worst part for her was the only corset that fit her waist was a full cup size smaller than hers, so her thirty-two d tits were on the verge of falling out of the lace cups. At first, she said no. But the sales lady talked her into it saying he was one lucky guy to have a wife that looked like her. And she had to agree. Jill was standing in the dressing room looking at herself in the mirror. the corset was all black lace, with the bra part pushing her tits up and out, and with her stockings ending just below her firm ass. She had never worn stockings before this. She loved the look and feeling of her garters holding up her stockings. Boy, would her husband like this, she looked at the saleslady and said, " I'll take everything."

Her friend said she ought to wear her new outfit to work Friday, they were both laughing about the effect it would have on me. Then Jill told her, she had caught me checking out her tits and ass on more than one occasion especially in the mornings, when she got out of her car. She said it didn't bother her because I was a nice guy, and pretty harmless. Besides it made her feel good, and women need male attention and approval. The need to be desired.

When Friday rolled around, I took up my post by the window to check out Jill getting out of her car. Sure enough she was teasing up her hair, then the door opened as I held my breath, but no regular stockings. She did have on a super tight blue skirt with suntan panty hose. Jill was aware that her boss was watching her from inside, and decided to give him a little show. She didn't need much help. The skirt she was wearing had ridden all the way up, to her waist.

By swinging her legs out and standing up, her blue panties were exposed. She took a minute to pull her skirt down and closed her car door. Jill walked toward the office, laughing to herself about the show she had just put on.

"Good morning Mr. Bennet", she said with that beautiful smile

"Good morning, Jill you look very nice today"

With that said, we both went to our desks and started to work.

Jill asked if she could take lunch at two today her friend was going to meet her. I said yes of course, it would turn out to be the smartest thing I had done in months.

Jill came back fifteen minutes late and maybe a little tipsy. She swung open the front door and said

"Where's the best boss in the world?"

I was wrong, she was just about drunk.

Jill had on a tight white silk blouse that gaped open at all the buttons.

"Jill, could you come here when you get a chance."

I could see her standing by her desk she was quickly unbuttoning her top two buttons of her straining blouse. "On the way Mr. boss man," she giggled. Knowing what she had just done. She was walking as fast as her heels would allow. Her tits were jiggling up and down trying to pop the remaining fasteners.

"What's up boss," she said breathlessly as she leaned on my desk. Her lacey white bra clearly visible struggling to contain her boobs.

I must have been too obvious staring at her chest.

"Oops I'm showing my undies, what would my mother say," as she made a show of buttoning her blouse. I had made up bullshit reason about seeing her about an account that she had already taken care of. I asked if lunch was good, she just smiled and said her lunch came in a glass.

Jill said, if I wanted her just call, then she blew me a kiss and wiggled her way back to her desk.

While she worked, she was humming and talking to herself, she was definitely high. And I was going to take advantage of it.

I walked up to Jills desk, she swung her chair around to face me, her skirt was all the way up, exposing her nylon covered legs and a small patch of blue panties.

"What's up boss,"

I'm glad she's not this way all the time, it was getting annoying.

Jill why don't we go out for a drink or maybe dinner tonight after work?

She looked troubled for a minute, then turned toward her desk and pulled her skirt down to her knees. I thought I blew it.

She whispered, "That's sweet, but you know I'm married, it wouldn't be right."

I panicked and tried to save it. I reassured her it was not a "date" just two coworkers having a drink. I told her I realized that she was down about her anniversary, and I didn't want her to be all alone.

"You're right, I'm being silly, I'm flattered, and you've always been a gentleman. So sure, I'd love to."

She wanted to go home to freshen up a little and asked would I mind picking her up at her place, so she didn't have to worry about driving later. I said I didn't think she should drive now, and she agreed. I would drive her home know and then pick her up, in an hour.

It was almost five, so we closed up, and went to my car. What a leg show, Jill got in my car sitting down with her legs exposed. Her skirt was up to her crotch exposing her blue lace panties and in her drunken state she didn't bother to pull it down. Jill was a talker when she was sober, but with a few drinks in her she was nonstop.

I dropped her off and watched her wiggle up her stairs to her house. She turned and waved. I thought "What a fool her husband was, leaving her alone.

I was on my way back to my place to change when my phone rang. It was Jill, good god please don't let her cancel. But she just wanted to know where we are going so, she knew what to wear. I had no idea, so I lied and said it was dressy. I knew what I was wishing for.

I gave her a good hour and then went over, she met me at the door in a floor length terry cloth robe.

"I'm running a little late, I had trouble with my hair, my French up-sweeps skills are lacking," She laughed.

"You look great to me." I said.

Jill blushed; "You're so sweet, I made a pitcher of margaritas, they're in the kitchen, now let me finish dressing."

If she made a full pitcher, then she had plenty to drink already. I got my hopes up for a fun night.

After a half hour, Jill called out "I'm ready"

And it was well worth the wait. She carefully walked out of the bedroom, wobbling slightly on pencil thin four-inch black high heels. Dressed in a knee length skintight black leather skirt and a gray sleeveless sweater, with her hair in a French twist, her long neck highlighted by a black choker. She looked gorgeous.

"How do I look, is this too tight?" she said smoothing her skirt. She looked flawless.

"Now let's get going." She said, Like I was the one holding us up.

"I want to get going before my nosey neighbor gets home and sees me dressed like this."

Jills tits looked like they were going to punch holes in her sweater. They were perfect, round and soft and with every step she took they bounced, like they wanted to break free of her overworked bra.

When we got to the door, she gulped the rest of her drink and grabbed a black jacket and laughed.

"I've got to cover my girls up, they're ready for action. And they have a mind of their own."

I don't know what she meant, but I was enjoying the show.

I held the car door for her, as she swung her legs in, careful to keep her skirt down.

"This is going to be so much fun, my boss man."

I know it would reduce my chances of getting anything from her if she was sober, but this "boss man" stuff was getting on my nerves. The drinks she had were really hitting her.

The first two restaurant's we tried were booked up with a three hour waiting time. I knew she couldn't wait that long, and neither could I.

We finally decided on a bar that served appetizers.

When we got there, I opened her door again, and this time I was treated to a little more of her black nyloned covered thigh. She didn't seemed to mind as I made no attempt to look away.

We sat in a booth, and ordered drinks. Jill was a not an everyday drinker it was almost seven and she was just about drunk.

I ordered appetizers, which she scoffed down. I knew I had to make a move.

Before the waitress came back, I suggested we either go back to my house or hers.

"Just what are you suggesting Mr. boss man have I've been a naughty secretary? " she slurred with an exaggerated wink. " Maybe I need to be punished?"

Without waiting for an answer, she said,

"Let's go to my place, I feel like I'm going to pass out."

I didn't want that to happen, I wanted at least to get her home and then awake or passed out I could have some fun.

Jill took my arm for support as we left the bar, she was unsteady, between the drinks and her high heels, she needed my help to walk.

I opened the car door and as she sat on the seat, It was my chance, and I took it. I made sure to cup one of her tits as I was trying to get her in the car. Jill didn't say anything, her head was lolling around. So, I got bold and cupped both her tits, rolling her nipples between my fingers. Her tits were big soft mounds, they must have popped out of her bra, because her nipples were clearly outlined against her sweater. She was moaning as I mauled her massive rack. She seemed to be passed out.

All of a sudden, she woke up, a little disoriented.

" Hey, Mr. boss man are you feeling my boobs up?" she giggled. Then added.

"I don't know what the big deal is, there just boobs. You can play with them if you want. Sometimes I do when I'm alone and can't have sex. I play with them I really do. Oh god I'm so drunk please don't listen to me. I just want to go home."

She was sitting on the seat with her feet still on the ground, nodding off.

'Jill I'm going to swing your legs in the car, ok?"

"Sure, just don't feel me up again, I'm a married woman you know, and I know what happens to drunk girls."

I reached down and grabbed her ankles and swung her legs in, inching her skirt higher, she didn't seem to notice. I reached over her to fasten her seat belt in the process rubbing her boobs with my elbow, god they felt great.

"What are you trying to do, boss man?"

" I'm trying to fasten your seat belt Jill, so I can get you home."

She wasn't helping at all, I finally got it fastened making sure to run the belt between her tits. I had gotten away with a little so I thought I might as well reward myself. She was still sort of passed out, her eyes were closed, but she was sitting upright. I grabbed the bottom of her skirt and pulled it up, to my surprise I exposed stocking tops and black garters, wow, who was she dressing for?

I squeezed her tits one more time, pinching her nipples, she leaned back moaned and squeezed her legs together. I was going to have some fun tonight.

When we were pulling up to her house she started waking up.

"Hey,why is my skirt pulled up, you're not supposed to see my new stockings, there for my husband,that lousy bastard, leaving me alone on our anniversary?"

"You had trouble getting in the car, don't you remember?"

"I'll just bet, while you were at it why didn't you take my sweater off too? I'm not dumb I know what guys do when they get a girl drunk."

Thinking to myself, there were too many people around for that, or I would have taken her top off too. We parked in front her house and Jill said.

"See you Monday."

There goes my night. At least I got some free grabs.

Jill opened the door and staggered out almost falling. Her skirt still well above her stocking tops, she wasn't worried about her neighbor seeing her now.

"Please help, I'm going to fall down. Just keep your hands to yourself." she added.

We got up the steps to the front door and went in, I figured she was going to kick me out. But she said, "Come on let's have a night cap."She had no idea what she was saying.

Jill plopped down on the couch showing a lot of leg.

Both of her stocking tops were exposed along with her garter straps, struggling to hold her black nylons up.

She saw I was staring but made no move to pull her skirt down. She was drunker than I thought.

The pitcher of margaritas was still in the fridge, so I poured her one and took it in to her and noticed she hadn't pulled her skirt down.

Making sure to get as close as I could to her, I sat down.

"Why aren't you drinking?" she slurred.

"I left it in the kitchen."

"BULL SHIT, you want to stay sober, get me drunk then fuck me, ya know I'm so wasted now I don't care what you do. I like you, you're a nice guy, so do whatever you want to, just don't hurt me."As she "drunk rambled" on.

Thankfully, with that she seemed to pass out.

Now was my chance, I grabbed the bottom of her sweater and pulled up, Jill sort of moved up, making it easier to pull it off. You talk about "sweater meat," her tits were it. Perfect, round and way out of proportion to the rest of her body. And I was right, they were out of their cups, riding on black lace bunched under them. Next came the skirt, I rolled her over a little to get the zipper and with one move I yanked her skirt off.

Of course, she picked then to wake up.

"What the hell do you think you're doing?"

"Just helping you get out of your clothes, you said I could do anything I wanted."

"Well, you bastard I changed my mind, now take me home."

"I've got news for you; you're already home and I'm just trying to help you."

She just stared at me in a fog, then she realized her tits were exposed. She struggled but finally got her jugs back in the cups, but what a sight it was.