Someone who worked for you....
 

Anyone interested in some stories from when I had a young, beautiful blonde work for me? So many upskirts.

Of course :-)

I'll share a story of a legal office assistant who worked with me 8+ years ago. She was in her mid-20's, tall, athletic, very attractive with red hair and large, natural breasts. We were friends, although each of us were in separate serious long-term relationships.

One weekend, I was working (aloe) at the office, and walked into her cubicle space to retrieve a printed document. (One of the office printers was located within her sizable office area.) It was dimly lit at the time, and I accidentally knocked over a large binder. I discovered that the binder contained about 60 CD-ROM disks, with handwritten descriptions of the contents.

It turns out the assistant had used her office computer to transfer thousands of her personal photos on to CD-ROM disks. Out of curiosity I flipped through the CD-ROMs. Most referred to friends' weddings, birthday parties, vacations and similar events. However, there was one inscribed, "Dirty Pictures." On it were fifteen explicit POV photos taken by the assistant's boyfriend of her nude, giving him a blow job, and then fucking him from on top. There was also a two-minute video of the same encounter. They were epic!

OF COURSE, I my a copy of these for myself before carefully returning the binder to its normal place on her desk. For the next two year of her employment, I would periodically explore if she stored other photos. Alas, no luck.

Unfortunately, I cannot share. Over the years, I've lost track of these photos/video.

How could
 

anyone every lose track of something like that??

Unfortunately, yes.
 

I lost some great pics. One Mardi Gras I was invited to a balcony on Bourbon St. by one of our vendors. Of course there were lots of beads to throw to the crowd for 'favors', the 'favors' were usually women showing their boobs. I brought a nice camera to record the festivities.

I looked down and who do I see but 2 attractive ladies from our accounting department. They didn't recognize me because it's dark and all the lights are pointed down to the crowd. I ask the guy next to me to see if he can get their attention with some really nice beads. It works, I'm snapping pics and the ladies are pulling their tops up flashing their ample breasts.

That was about 15 years ago and somehow I lost the pics in a computer swap or hard drive failure.

Apprentice
 

I work at a dealership as a service technician, 3ys ago we had a young girl placed with us through apprenticeship. Wasn't drop dead gorgeous, but not ugly by any means. I was responsible for training her. For 6wks I got some frequent down blouse treats. I would guess a 34b.

I want to know more about this blonde relationships...

She Had the Highest Set of Boobs I Ever Had the Pleasure of Visiting
 

When I first got out of college, I was a computer programmer. I was assigned a "Keypunch Girl" to key my programs on punched cards (it was 3rd Generation equipment). I must say that this girl was a looker from the get-go. However, aside from her beautiful face, she had boobs that sat higher on her chest than any girl I had ever seen. All the programmers had noticed it, and most all said that she was wearing falsies. I said that I didn't think so. They all laughed and said that we would never know. Eventually, we had a party at some apartments with a pool. Everyone was there in their swimsuits. She had a very small bikini on that afternoon, and I studied her well. It was my learned opinion that her boobs were real. As the afternoon turned to evening, everyone changed out of their suit before heading home. This was the early 70's, and most girls didn't wear bras when dressing casually. She was no exception. I could detect pokies under that blouse. Few people were still at the party when I saw my "proof." That following Monday at the office, the conversation turned to her and her bikini. I then said that I had proof that she was real. Everyone laughed when I mentioned the pokies. I was told I was dreaming.

I made seeking the real proof my major mission. We were both married, but I felt that I might have a chance to have a little affair on the side with her. So one day I asked her if she would like to have a drink at a bar after work. She readily agreed. We went to a nearby bar and had a couple of drinks. We were in a back dark corner of the bar sitting side by side in a booth. Pretty soon we were in a very hot make-out session. Fairly rapidly, I had her blouse unbuttoned and her bra unfastened. She was hot as hell and breathing heavily. I found out immediately that her boobs were very definitely for real. I then went for the gusto and started fingering her. She was ready for everything. And shortly she was moaning and climaxing from the rigorous finger fuck. But some patrons were a little jealous of all the vocal sounds she was emitting. One even said, "Get a room." With that she said, "Let's go." She buttoned up, and we headed out. I had gotten the whiff and was not about to stop the process at this stage. I said, "Let's head over to my car in the parking lot." She agreed. Once in the car, we headed into the backseat and had wild, unadulterated sex. I buried my head and face into those magnificent high set boobies. I could have munched on those all night. However, her soft, wet pulsating pussy also demanded attention. We screwed for close to 30 minutes. Eventually, we agreed that we needed to get home to our spouses, but we promised to get together again and as much as possible in the future. The next day at the office I had the proof. Nobody laughed this time. I only heard comments like, "You devil, you!" and "You the man!" It was the beginning of a great 6-month affair.

My first job as a manager of people, I had a very competent assistant. She had a decent face, but a knockout body. Absolute 10/10 with lovely big tits. She used to wear low cut and tight tops all the time. Whenever she wanted something (time off/early finish etc) she would lean over the desk, pushing them together with her elbows.

Not once did I refuse her mega-cleavage a single request! :D

Found her on facebook recently...

Lovely Assistant
 

I worked at a large firm at its HQ office heading a mid-sized department. There were a number of attractive young ladies with an average turnover of three years as they left to marry, have a baby, etc.
I noticed one thing not taught in graduate school.
The most attractive ladies were used to using their beauty to get out of any mistakes they made or to get out of criticism. This included showing a lot of thigh, crossing their legs in an unladylike way, opening buttons on their blouse to show cleavage and one, knowing I was upset with her, chose to wear stockings under a short skirt the day I returned from a trip. She had worked for me for more than two years and I can assure you she wore pantyhose in the cooler months and would go bare-legged in the hot months like other ladies on our office. As we had our very serious discussion in my office, the skirt worked itself higher until bare skin was showing.

co-worker and emplyee
 

In Highschool I worked as a day-camp counselor working with school aged children. There was this blond girl that worked with me, she was the same age as me. She was hot and athletic. She was the lifeguard and had this

incredible tan. We flirted a lot but nothing ever happened between us. Fast forward to the mid 80s I was working for another company as the general manager. The blond that came to work there and I was her boss. As soon as she came to work, I felt the attraction between us. She flirted and I flirted back.

One day we were in the back of the building and we were both in a supply closet. We started kissing and I grabbed her ass and she didn’t shy away so I went straight to her tits and pushed up her shirt and bra and went to sucking on her tits. I was surprised how her tits were; way bigger than I thought. They had to be double D or whatever the next size up is. She gave out a low man but not to be too loud. There were people about 15 feet away. It was exciting to be that close to being caught. We straightened ourselves up and went back to work as if nothing happened.

The next day she wore a mini skirt and her legs were still athletic. She was a skinny atheletic with huge tits. As I was looking at her legs, she caught me looking. She gave me the come-hither finger motion. When I did, she whispered in my ear, “I’m not wearing panties.” I almost lost my breath. I went to my office and contemplated what was about to happen. She is my employee and I wondered if it would cause problems for the company. I could not get those legs out of my mind. That denim mini skirt just looked too damn good. The more I thought about it the more I started to lose control over my inhibitions. It wasn’t long before I walked to the storage closet again and she followed without anything being said.

As soon as she walked in, I said prove you are not wearing panties. Without hesitation she lifted her skirt and her pussy was shaved bald. That was a big deal in the 80s. That was not a common thing in those days. Anyway, I reached out and touched her smooth bald sn*tch. I mentioned on how smooth it felt and how pretty I thought it was. We started kissing and I was fingering her and she was rubbing my cock through my slacks. I turned her around and bent her over a table/desk thing and I fucked her hard and fast. She was holding in her gasps and was trying to be quiet. I wanted it to last longer but was afraid I we would get caught So I came in her pussy and we straightened ourselves again and went back to work.
The strangest thing happened next. The owner came in about an hour later. He had been out of town. He called me into his office and proceeded to give me a speech about in office affairs and how it could affect the company. In my mind I was thinking he knew and I was about to get fired. But he finished by saying If is see any of that going on at the company to put it to an end. This was too coincidental I thought. I thought surely, he knows. But he never said anything. I went to her and told her what happened. Her face turned white and I said we need to stop this or we will both get fired. We agreed and about a month later she quit and went to work somewhere else. Fast forward to the mid-90s

I was working for another company and she knew the owner and stopped in to say I to the boss. After her visit with the boss I ran out to her car to see what was up. I stood outside her car and we had a general talk about our lives. She was married, I was in a relationship with another girl. She still looked good. We were both in our mid 30s at this time. Her tits were bigger and she still looked athletic. I was in the gym all the time. Out of the blue she says if you want to get together, she was game. So, we made plans to meet up at a dive bar after I got off work.

We get to the bar and we sit in a booth and I sat next to her. We both ordered a drink and as we were talking I put my hand on her thigh. When I did she let out a moan. That told me everything I needed to know. I kissed her and felt her up in the bar. There were a few people there but no one was paying attention so I put my hand in her shirt and felt up her big tits. I said let’s go somewhere. My girlfriend was at my house and her husband was home so I went to get a room and a local motel but it was full so we went to a place to park. By the time we got there she was already naked and I went straight to licking her pussy. I was fingering her and sucking on her clit. She pushed me back and started sucking on my cock. I wanted to fuck her really bad but just as soon as I was about to get on top of her these damn teen age kids came up and started looking in the widows and started teasing us. We lived in a small town and I knew one of the kids, he didn’t recognize me I knew this was going to be dangerous so I said lets meet again and I will have a room ready.

After planning everything I was so excited I got to the motel room early. When she finally got there, she said she didn’t have much time. Damn; again I was not going to get to enjoy her. But damn she looked so good. In her md 30s she was still tight. Her ass was tight and firm. Her tits were huge. Her skin was creamy with a few freckle scatters over most of her body. Her body was firm and still a little athletic. Her pussy was shaved, still. Only a couple of stretch marks on her lower belly from her pregnancy but it looked good on her.

I pushed her down on the bed and started eating her pussy and she asked me to stop and wanted to watch me take my cloths off. I did and went back to the bed and she grabbed my cock and started sucking it with enthusiasm. I went back down on her and was eating her pussy and right in the middle of what I was doing she took her leg and lifted it over my head I did not know what she was doing at first then she got on all fours and arched her back so I started licking her asshole. When I did, she let out a loud moan. At that point I knew I was getting anal that night. I got behind her started fucking her doggy style she was getting loud and was bucking up against me. She was very enthusiastic and came a couple of times. I slapped her ass a couple of time and started pushing my thumb into her ass while I was fucking her. I felt it loosen up as I was fucking her. I went back down on her and I licked her ass and was trying to lube it with my saliva. She was pushing her ass into my tongue and I started tongue fucking her ass. She was moaning and pushing back against my face and tongue. When I thought she was ready I stood up next to the bed and she backed up to me and I put my dick on her asshole and I held firm and let her push. She started rubbing her clit and I held still and felt her push a little at a time until I was fully inside her ass.

She started rocking a little at a time for a little bit, then she started getting into it and was pushing back and then she told me to fuck her harder. I did and she was screaming and getting a little to loud for my comfort but if she didn’t care so neither did I. I told her I was about to cum and she told me to cum in her ass. I grunted and pushed into her she pushed back hard against me and I came hard. I almost passed out. When I was dizzy, I laid down and caught my breath. She cuddled next to me and said this was the last time we could ever meet. I didn’t ask any questions. I already knew. I was just glad I got to see her and finally get to fuck her the way I wanted to. She said she was going to go home and fuck her husband and didn’t want my cum in her pussy.

She said he could never find out and wanted to make sure I was going to be cool. I said don’t worry. I didn’t want my girlfriend to find out either. My girlfriend was a wild sexual dynamo at the time. To tell the truth if my girlfriend would have found out, it might not have caused a problem. But I didn’t want to find out. I have written a few stories about my then girlfriend on oneclick non-fiction forum.

We had a very part-time nanny who was 22yo at the time. She did a lot of late nights for us and even came with us on day-outings, and we all got to know each other very well. She was very professional, never flirted, dressed like an old-style nanny, etc, acted like she was in her 60s rather than 20s.

Her very last day, she came wearing tight jeans, a very thin long sleeve shirt, and a tank top under it but no bra. As I paid her for the last time, she gave me a very long, lingering hug. Very, very long. Tight. Lingering. Hug. I felt her smooth back without brastraps and her incredibly soft braless breasts pressing into me, and I noticed they were much larger than they appeared under her clothes.

My wife, who normally wouldn't mind, was sort of upset by her very long, very out of character hug. I didn't mind. Even though she was very very skinny as a toothpick, her body was very very soft and not bony. Still one of the best hugs I have ever received, and I will remember it forever.

I have a story with an opposite point of view.
I was at the beach with my wife. She received a phone call from a coleague, he was in the same area with another coleague and my wife invited them to join us. After one hour they arrived and they spent a few hours with us on the beach.
My wife is an attractive 40-year old woman, the two guys were about 30-year old and I understood that my wife is their boss. My wife was wearing a bikini like the one in the picture. For me it is very exciting the situation of meeting your coleague (or better your boss) wearing a bikini instead of the formal/business suits used everyday in the office.
But there is something more.
My wife was laying face down and she asked me to put the tan lotion on her back. I reduced her bikini bottom like a thong with the goal of putting the lotion on her skin without touching the bikini with my oiled hands. My real goal was to expose her ass in front of her coleagues and I did it for a couple of minutes.
But again there is somehing more.
She untied the bikini bra to avoid tan lines on her back. She received a phone call, she had some problems in finding the phone inside her bag being face down with the bra untied. Everybody was looking at her, finally she made a mistake and she lifted on her elbows exposing her tits for a few seconds.
I can only imagine the conversation of the two guys on the way back home or at the coffee machine in the office the next day. Trend topics the bikini, the ass and the nipples of their coleague/boss.

I have an interesting one going on now, well not exactly going, I am still on the fence about it all.

She is late 20's and I am 20 years her senior. Knew her a little before we worked together. Originally she was hired as my assistant. She spent three years sharing my office, 4 feet from me. She is engaged, has a child. She is absolutely stunning. I cannot say i have run into any woman like her in my life. She is not my assistant anymore but we work closely in the same department.

During all that time in close proximity we got extremely closer. Literally talked about EVERYTHING. Nothing to this day is off limits. We know everything about each other. She knows I look, I do not hide it. Few times the word "Jesus Christ" has come out of my mouth and she just laughs. If she comes in my office and ends up using my computer it is always bend at the waist RIGHT in front of me. No way she is that oblivious about it and she has to realize what is right in front of me. We spend a ton of time together weekly, even in the car visiting clients for day trips. Always just talk. So as the work husband I get to hear it all about home life. Admitted there are at least two, maybe three porn videos of her in existence with different guys that she said she "just was not thinking" and really does not care. College she was banging one of her professors at another professors house for a while. Few other things (she was a wild one) as well as not getting laid at home now. Which blows my mind. We text occasionally, we go out after work once or twice a month, go to lunch a few times a month so she obviously likes my company. If they make a trip to the beach, I will get a bikini pic or two. One vacation they were on i was getting snapchats of the festivities and there were hearts and stuff on them. "You realize what you were sending me with hearts and kisses?"........"Yeah, i was pretty drunk"

But during these conversations she will always throw in stuff. Professor she was banging was waaaay to into her feet she said. "I do not like that, stay away from the feet".....Joked if its doggie and you pull the hair too hard "I will turn around and punch you. You have to be NICE to me". All kinds of stuff like that, details. A female friend of mine said "She is into you. No way a woman is going to tell you all the stuff she does not like if it was not for future reference".......Oh, I never thought of that. "Plus she is comfortable enough to talk to you like that" Interesting. I am not a bad looking guy, I am in shape, I am told I am one of the good guys so i guess it is not too far fetched thinking she may like me a bit more than a coworker? I did joke one time that older guys are better. We know what we are doing and to be blunt we keep our mouths shut. She just chuckled.

There was going to be an overnight work thing her and I were going to to go, that would have been interesting. But due to covid it got cancelled.

I am always on the fence about her. I could push things slowly i guess and see what happens. The old saying that i have lived by forever "you don't shit where you eat" concerning coworkers is off the table with this one for sure.

I've got two things to say about this.

The good one is that, no matter if nothing ever happens, it reads like a friendly and flirty relation, which is a very nice thing.

The bad one is that, if I were you, I would not push it further. In fact, I would not have let it reach even this point. At my workplace, there's a woman who got in one of the top positions by doing almost exactly what you describe. She got (overly) friendly, and flirty, and sexy with an older medium-level manager for quite a while. Then, as soon as he finally made a move on her, the shitstorm started. At the end, she made a deal (I would call it blackmail), and to avoid a very media-public harassment suit the guy was let go and she was offered one of the top-level manager positions in the company. And by the way, she is a rude arrogant person who takes pleasure in gratuitously (and literally) insulting people, and nobody can tell her anything. So, I'm sorry for being the voice of caution, but... well... I'd be very cautious in your position.

Oh I am old enough to be VERY aware of all of that for sure. We were friends prior to her working at the same place so there was a comfort level prior. She is an interesting one though. People joke that we should be married, and despite what we talk about, she is very reserved at work. It is a male dominated industry we work in, so she stands out being young and looking like she does. We have been places and the entire job site will stop and stare. Which I tease her about. There are a few times she has come to me when someone at work needs a slight attitude adjustment, there are a few that have hit her up privately on social media. That is me being her friend more than anything else.

I always leaned towards the flirty friendship side, just because of how well we know each other and how well we get along. She has to know what she is doing, probably enjoys the attention if she is not getting it at home. I get the privilige of certain things because she is so comfortable with me, and that is certainly not a bad thing at all. Makes the work day a whole lot better.

Remember, sex always changes everything. You seem to value what you have. If you are going to lose it, make damn sure it is worth it.