[Request] Sexy Female Bosses

[Fredox2]

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.

[firedog6]

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!

[legno]

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

[nectcouple]

Originally Posted by PolyPhil

worked at a temp job once for a few weeks, was very good money but was ruined in large part by this woman, who was an absolute ball busting b*tch who I personally blame for costing me some dough, so screw it, here is what I saw when I worked there.

It was summer time and she favored low cut shirts. Several times when she reviewed my work at my computer she would lean over and I would see almost everything. No nipple, but she tended to favor silky bras that didn't offer much support, to the point that I could testify that her big tits were natural and saggy. Anyway, it became so obvious at one point I didn't even have to look at her directly, just watch her reflection in my computer monitor to see her big floppy cow titties.(I didn't want to give her any excuse to can me by claiming I was looking down her shirt... such was our "relationship"). Even then it was so obvious she must have seen her reflection and she pulled up her shirt once. Oh well, no more cow udders.

Part of our problem was that her desk was directly behind mine, so that whenever she decided to "look busy" she would bother me. All good though. If I ever got bored all I had to do was turn my head and invariably I could see her panties showing above the brim of her pants. She favored thongs.. red silk, red lace, and a black silk number I know she wore two days in a row. Not that I was trying that much, god's honest truth, I didn't find her attractive at all and I despised her attitude. Completely unprofessional, self serving and conniving. Not saying that just because she cost me a shot a good job, but initially I made a real effort to be kind and polite to her, but as the pressure of the job mounted she showed her true self, not to mention her titties and panties.

ANyway here is a picture of this b*tch from her Fb page. Years later and I still hate this woman.

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

[Taurus44]

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?