Attracted to my 50 year old boss

Whilst I’m confessing my soul to the world, I might as well fill you in on another (slightly embarrassing) confession. Like many younger men before me and, indeed, many younger men after me I’m slightly attracted to my old, wrinkly and generally unattractive boss.

Yes – Yes I do have some serious issues to deal with.
But hear me out …

Whilst she may not be the most attractive 50 year old woman, she does have something about her.

First of all, she’s blonde and – whilst I’m a fan of the younger brunette – I love shacking up with an older more sophisticated blonde woman.

Secondly, she is extra feisty. She yells, screams, throws tantrums and is generally quite miserable. And something about that tantrum throwing just makes me want to take her out the back and spend half an hour making her scream for a completely different reason.

Thirdly, and perhaps the most obvious reason for me wanting to give her some of my bodily love, she’s off limits. I’m never going to have sex with her and that makes me want to do it even more. Any move I make is going to end in a law suit so I have to wait until she makes a move, which will never happen, and that is making her more attractive.

And for those 3 reasons I’m attracted to my ugly, demanding boss.

Sadly, this is not the first time I’ve been in this situation. 2 years ago I was working for a large company in a huge office building. The company I worked for had a flexi-time policy meaning people could come and go as they please provided they did the 30-something hours a week. The main result of flexi-time was that by 4.30pm, 90% of the building was empty. By 6.30pm, it was just me and about 3 other people in a huge building built for thousands … oh, and the cleaners were there as well.

The cleaner assigned to my section of the building was an old, depressingly ugly woman who was a little bit strange. The one thing going for her was her incredibly large breasts. Everyday, whilst working late, she’d work past my desk and I’d imagine touching those enormous boobs. Over the months I was there, the two of us did a little flirting but nothing too obvious.

And one day things changed.

About a month before I was due to leave that company, I stayed extra late until everyone was gone. It was about 7.30pm before I plucked up the courage to make my move. So I wondered over to her whilst she was wiping the bench and spent a good half an hour talking, flirting and talking some more. Arms were grazed. Hands were touched. I went the full nine yards.

Then I suddenly started talking about her dates and how big they were downstairs. Shocked, she didn’t really give away too much. Then I used the old “I’m not quite sure whether mine is big or not … what do you think” and held up my hand with my approximate size.

“Looks like a good size” she said. I had gone too far to go back now so I just went for it and tried my luck.

“Ahhh but I guess you can’t really tell looking at my hand – It’s a bit embarrassing but could you do me a favour? Could you have a look?” I said and wandered over to a dark corner of the room where we wouldn’t be seen.

She came over and I unzipped. She looked down for a minute then slowly ran her hand up and down over my foreskin. She was giggling slightly but didn’t stop rubbing. I kept looking at her boobs and slipped my hand in to feel. They were soft and as big as I’d imagined. Thinking back on it now I still wonder how it all came together.

Trying my luck even further, I asked her if she wanted to join me in the disabled toilet. It was a huge toilet, big enough to stand and have sex.

Unfortunately she didn’t want to. She said we should go out for a drink at the weekend but I knew it was now or never. I was leaving the company soon and didn’t really want to spend my weekend having a drink with her. I wanted the office sex fantasy come true.

Failing to convince her to join me – I took my erection and went to the toilet by myself, before heading home.

Even now, I smile at the thought that I managed to get a great story like that but always feel like I missed out on a trick but not finishing the deal. Then I wonder if some fantasies are best left as just that … a fantasy.

8 Responses to “Attracted to my 50 year old boss”

  1. Great story man. I wish things like that happened to me so I could write about it in my blog. I would love to tell people about these great sex stories or hooking up with girls but alas my love life is empty. Drinking at the bar till I can’t see anymore and I leave to go home alone. Very depressing.

  2. I’d love if you would link to my blog on yours. If not, I’ve already put you on mine since I think you write some great stories.

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  4. this story gves me big smile – i really like your soul- and i hope to hell when i am 50 someone like you appears to put the sun in the sky. i would have tested the disabled loo for sure!

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  8. I have to agree and found this very interesting :-)

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