Sexy Female Bosses
 

I'd be interested in hearing from anybody who had a female boss that they lusted after or had any visual or physical experience with at all, or even heard good rumors about. I personally have three mild stories, no sex.

BOSS DOWNBLOUSE

I was in my mid twenties, a newlywed, and had a commission sales job working for a woman who was perhaps in her mid thirties. She was married, no kids, very attractive in an Audrey Hepburn sort of way; a trim pettite body, short dark brown hair, an upturned nose, small breasts, nice legs, nice butt. While I couldn't help lusting for her, she was a little stuck up, and our relationship was purely professional, our conversations business only. One warm day she was wearing a sleveless summer dress that scooped down some. I was in her office, she leaned over to go over some papers on her desk, I stood over her as her dress gapped open, her left bra cup also gapped open, and I spotted her darker nipple capping her little breast. My one and only female boss titty sighting.

Hot Boss's Boss
 

I am middle-management, one step away from what my company considers executive management. My boss's boss is a slender blond woman in her late forties. Very trim, pretty face, bleached blond hair. She's about 5' 7", and I would guess about 130 pounds. She's sexy enough without knowing anything about her. But she is also brilliant, self-assured and approachable. For me, those things just make her incredibly desirable and hot. (Doesn't hurt that she also makes upwards of a quarter-mil a year.) Unfortunately she never wears anything revealing or sexy, but she is always nicely and professionally dressed. I would guess that she's a B-cup, and has a great little runner's ass from what I can tell when she wears slacks. I run in to her and her husband away from work occasionally, and she even looks nice on the weekends. I SO wanted her husband to be a dick, but he seems to be a great guy and I guess she won't be on the market any time soon.

BOSS LEG RUBBING
 

When I was in my late thirties I took a job that I realized the first week was a mistake and I wouldn't be staying there long. My boss was a woman who was maybe a couple of years younger than me. We were both married, and she was neither attractive (not pretty, and a body that was a little dumpy) nor someone I particularly admired. She wasn't the major problem, but a small part of it. She was nice enough I guess but had that "company lifer" attitude that didn't make her someone I wanted to work for. All the same, she was my boss, a female, not ugly, around me every day, and so I'm sure I had some sexual thoughts about her.

One day she was at my cubicle for a sofware demo. I think that I sat at the computer and she sat next to me. Soon enough when she leaned in to show me something, her knee made contact with mine. I could have backed off, but as is my custom in these situations I left my knee where it was. So she leaned in a little more, and soon got to the point where our thighs were pressed firmly together, I could feel the texture of her pantyhose beneath her long thin skirt as she moved. I was sure that we were both aware of the physical contact, we were both pressing together, there was an aire of sexual tension, and she had that little supressed smile that I've seen before in these semi-taboo situations. That's it. Not a great story, but it was nice to know that I had a female boss that had at least a little sexual interest in me.

I had a female boss for over 10 years, she was actually the trophy wife of the rich old guy that owned the company. She was attractive, a "my shit doesn't stink" type b*tch, didn't know enough to actually manage people, she ran off many good employees, including eventually me.

One day we are going to an industry meeting about 200 miles away, I'm riding with her in her huge Mercedes, she's following her GPS to get to the little town where the meeting is, GPS's were new and she must have set it to shortest distance because it told her to turn off the Interstate about 20 miles before I usually got off. I argued with her and told her to stay on the Interstate but she was bound to follow her new $800 gizmo.

Sure enough we are on some curvey two lane road, it's dark and raining, she's driving too fast and I have no idea where this thing is taking us. I thinking if I die in a wreck with her I hope my wife gets a billion bucks out of this . Sure enough she skids off the road into a shallow ditch and we are stuck. I haven't seen another car in the last 15 minutes and I realize we're in about 1.5' of water and muck, she reached for the door and before I could say "don't open that" she did and now the floor boards have a few inches of water. The cell phone was mounted in the car and luckily we had a signal. Anyway, to make a long miserable story short, a tow truck finally got there, we had to walk through the mud to get to the tow truck, he decided he would need help and will have to come back in the morning for the car. He was nice enough to help us get our 2 overnight bags out of the car and take us to the hotel that we were headed, all the time asking "what 'chall doing way over here, this ain't the way to there", which made me fume even harder at this dumb b*tch.

When we got in the light of the hotel we were still soaking wet and Miss Priss's white silk $500 blouse was transparent and so was the bra she had on. Was it worth all that shit to see her nips, hell no. When we got back from the trip her husband, my other boss, was upset with me for letting her get in that situation. I only stayed with that company a few more years because they paid me so much and I was saving to open my own business, which I did.

BOSS LEG RUBBING II
 

She wasn't technically my boss, she was the client I directly reported to every day for two years. I was in my early forties, she was the same or a couple of years older. Very attractive mature woman, I thought, perhaps Greek with the black hair and very nice curvy body. Her husband worked for the same company but in a different building. She was nice, I enjoyed working for her, but we never had any real personal conversations, it was all professional. But I heard that she was a belly dancer in her spare time, and some of the older employees recalled a time or two where she was drinking a lot after hours and started moving into a belly dance, so she had her erotic side.

One time she came back to the cubicle where I worked to look at some software. Just like my above story, she sat next to me and rubbed her knee into mine, and I didn't back off. Nobody else could see us but we were within earshot of others, and nothing was said.

Some time after that she again came into my cube to look at some software. This time she stood behind me as I sat at the computer. Soon I could feel her left upper thigh rubbing into my right upper arm and shoulder, my shoulder just a few inches from her pussy. She pressed firmly into me as I pressed back, and there was just enough rubbing going on that I felt that she had to be aware of what she was doing. But again there was no conversation and it didn't escalate. Another mild story, but another time that I had some physical contact with a boss that I had lustful feelings for, where perhaps somebody bolder or a quicker thinker might have been attempted to pursue.

Not a boss, but a vendor to a store
 

I got this second hand, about a woman who represented a company dealing in kitchen equipment. The fellow telling this story had had many adventures with the woman. He said that she was middle aged, and not a real knockout, but had a sexy side. Seems that anytime you were able to give her a good order ($$$), then your reward was getting your dick sucked by a real expert. Said that she could suck the cum right out of your balls.... Obviously, she got a lot of business.:D

Two kinds of sexy...
 

A few years back I worked for a high school. One of the assistant principals was a black woman in her mid-late 30s. She was very pleasant and quite pretty from the neck up. From the neck down, however, she could cause traffic accidents. Wow. She was very toned and extremely shapely on both the top and the bottom, yet she never wore anything remotely revealing (in terms of skin). She was excellent at dressing in a way that flattered her figure while keeping her appearance highly professional. You would hear a lot of the female teachers and students occasionally say something like, "I'd be willing to kill someone if it meant I could have legs and a butt like hers." Most of the guys would just exchange glances when she walked by and say "Day-um" under their breaths.

Contrast this with another teacher about the same age (35-ish). This teacher was a very slender and toned blonde who ran yoga and aerobics classes or something on weekends and the summer for extra money. She frequently dressed in a way I would describe as "business sexy". This is where you take a perfectly professional and respectable outfit, and then you make the heels higher, the skirt shorter, and the neckline deeper. She had those obvious "bolt-on" fake boobs, and frequently when she bent over you'd see the top of her g-string panties peeking out over the top of her skirt's waist.

She taught 9th graders. :eek: :D I have no idea how the boys in her class were ever able to concentrate.

I don't think I ever saw the assistant principal ever wear open-toed shoes. Even in June and August, it was always dressy pumps and stockings. The other teacher was pretty much always bare-legged, and usually wore peep-toe heels and wedges.

People quietly lusted after and admired the assistant principal, but they tended to gossip and spread rumors about the blonde teacher.

Yes I've had two!
 

One owned a security company I use to work for on the side,she had a account with a cemetery we would patrol after hours. One night she showed up and wanted to ride around with me,it didn't take her long to start teasing me and getting touchy feely with me,we ended up making out and fucking in the back part of the cemetery by some older graves.

The second one was a manager of a cleaning service which I did some work for,me and her ended up fucking in her office one night,she let me bend her over her desk and pound her from behind. A couple of weeks after that incident we ended up fucking in the back of a UPS warehouse in a area where no one came into after 10 am except the cleaning crew.

Both incidents were a long time ago and about five years apart or so from one another.

I have been luckyto have a few hot female bosses. The best perhaps was a stunning skinny blonde who had the best legs I have ever seen. She mostly dressed conservatively, but in summer she would flaunt those legs in some very short skirts.

Vice President's Jiggling Cheeks
 

The other day I was walking down the hall behind a female vice president, watching her butt cheeks jiggle. She's not in my direct reporting line, but I work with her often and so my job depends on her approval somewhat. She is not a babe, but attractive; forties, not heavy but a little bit of extra thickness. Our office is casual dress, so she never wears skirts, but this day she was wearing dress slacks that clung to her butt nicely, and as she walked I could clearly see her cheeks rise and fall, and jiggle as they fell. The kinds of thing one sees fairly often in public or in stores. But it's a lot sexier, or dirtier, being a subordinate lusting after a woman in a high position of authority's jiggling flesh than an average person, don't you think?

Linda
 

Years ago I took a job very temporarily with a job search firm. The boss, a woman named Linda, was a divorced woman about 10 years older than I, well built, and had a forceful -almost rough attitude about her. We worked together for several months without any particular flirting or other "social" behavior between us. Even though Tampa is a warm place, Linda always wore suits, so there wasn't a lot to look at.

I was married to a woman with some very definite ideas about what was proper and what was not. She definitely didn't think magazines like Playboy or Gallery were proper, and howled like a banshee if she found one in the house. The simple solution was that I kept them in a desk drawer in my office. My wife rationed sex as though it might run out, and I was perpetually horny. We were NOT a good match. That made my masturbation sessions about the only relief I got, and they often happened after work at my office since I had the mags there.

Linda had asked me to accompany her on a Friday to a dinner meeting with the owner of our operation and his area manager to talk about a new office. We met at the office and took one car, since I didn't know the place we were going to. the meeting went well, and when we returned we went back into the office. I told her I had some work to do, and planned to jerk off after she left. She said goodnight and I heard the door close and so took out a couple of magazines. No sooner than they were on my desk top, Linda walked into my office, telling me as she did so that the lights were out in the parking lot and she'd appreciate it if I would walk her to her car.

I hopped up and quickly left the office with her, hoping she hadn't noticed. As we were walking out the door of the building she said, "Going to do a little reading?" Well, busted! I started to apologize, and she said, "Why? What's in those magazines is pretty tame. My husband and I used to swing, so it's not like I've never seen naked women." I was a little taken aback, and figured the only safe thing to do was act businesslike, so I told her that, nonetheless, the magazines probably don't belong in my desk.

She then pretty much took the conversation completely over to sex by asking, "Do you jack off when you look at them?" I was stunned, but managed to say yes. She replied that it's a lot more fun to have a real naked woman to look at. I said, "True, but I have a good imagination." She replied that imagination will only go so far and that I just needed more variety.

By this time, we were standing at her car talking, when she wrapped a had behind my head and pulled me down to her lips. As we kissed she sucked my tongue into her mouth. When we pulled apart, she said "Your wife probably expects you at home, but we need to have a little meeting tomorrow."

When I arrived at Linda's house the next evening, she greeted me dressed in a sheer teddy. I didn't have "Hello" out of my mouth before she was on her knees, getting my cock out of my pants. She gave a GREAT blow job.

Nothing changed at work, except that sometimes when I worked late, Linda would come into my office, wordlessly close the door, push me back in my chair and unzip my pants, and suck my cock.

I used to work in a school and a few years ago the headteacher retired. She was married and in her early sixties. I had worked there for about 15 years and had seen her knickers a few times as she often wore shortish skirts. She had nice legs and wasn't unattractive but not the sort who would turn heads in the street. Over the time I worked there she had gradually got more plump and by the time she retired she was quite the 'mumsy' 60 year old. Our interaction had always been totally professional. On the night of her retirement 'do' at a local hotel, as the evening was drawing to a close, I went to say goodnight and wish her well before I went home and found her in the corridor. She was returning to the function room we had hired after visiting the bathroom, and we exchanged the typical hug and peck on the cheek. As I pulled away, she placed her hand on my crotch and gave me a quick squeeze! I was dumbfounded, and before I could say anything, she had a quick look up and down the corridor, then backed me against the wall and gave me a full kiss with her tongue in my mouth. I was still in a state of shock when she guided one of my hands to her bottom and the other between her legs outside her skirt. Then, with her mouth still clamped over mine, she slid her hand down inside my trousers, grabbed my cock and with the other hand lifted the front of her skirt and pushed her crotch into my hand. I slipped my hand inside her tights and knickers and my fingers slipped up into her wet, hairy c*nt. I gave her a quick rub and then, just as I was becoming fully erect, she withdrew her hand, pulled away, adjusted her underwear and skirt, gave me another peck on the cheek and walked away without a word!
I saw her about a year later at another retirement party and she never said a word about it or even gave any indication that anything had happened. Go figure!

mastophilus, that assistant principal sounds incredible. I wish you had some stories to tell about her!

Lol!
 

Yup. I've had female bosses like that. a total waste of a perfectly good pussy and pair of tits!

First Female Boss
 

Over 20 years ago, I applied to and was hired by a defense contractor for swing shift operations in the data center, and then later moved to graveyards. It was a good job for someone in college as I was. My Boss, let's call her Elaine, was a "large" lady, about 5'6" or 5'7" and pushing, if not a bit more than, 200 lbs. She was probably 15 to 20 years older than I. Shortly after I got hired, she was working on a problem at one of the terminals, she stood there, bending over the back of a chair with her dress on and she was of such a size that the back of her dress rose up enough to see more of her legs than I really cared to see. But since I'm a voyeur and she was wearing pantyhose, my Kryptonite, I took it all in as much as possible.

I year or so later, Elaine had gone on a health kick and she and I would play racquetball all the time. At first it was me running her all over the court, but with time, she became quite accomplished and I had to bust my ass to beat her. She also dropped about 60 lbs. Now this mid-40's woman not only didn't look all that bad, she was pretty hot.

One Saturday night she came by work to check and see if there was anything I needed. She was dressed in a parrot blue silk shirt, black leather mini-skirt, black pantyhose and black pumps. She looked totally Fuckable. I guess she must have caught me more than once ogling her. By this time we had a very strong friendship and I had no problem telling her that she looked very nice. I asked her what the occasion was and she stated she was going to dinner with her accountant, I told her he was a lucky guy and she blushed. As she was walking out of the data center I hung by the door and watched her walk down the hall. I gave her a wolf whistle, I couldn't resist. She turned, saw me checking her out top to bottom. Then she asked, "Would you rather I stay here?" I will regret this answer for a long time, I told her, "No, you'd better go, I won't get any work done if you stay." She actually looked a little disappointed, shrugged her shoulders, turned and left.

Stupid Stupid Stupid Stupid Stupid...

I could have totally boned my boss that night but passed on the opportunity. I'd be lying if I said I haven't jerked myself off thinking of how that evening would have gone had I asked her to stay. Oh well, what's life without some regrets?