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Gotta tell someone. I am in my early 20s. I started a new job a few months ago at a small family owned grocery store. My new boss is in her mid forties, a little skinny with small titties and a pleasant face. And so f'ing hot. During my interview I got the feeling she was eyeing me up, but i passed it off to my imagination.

As the days passed I caught her staring at me but again I passed it off as my imagination. Sometimes I would see her from behind in her knee length pencil skit hugging her slender body and my mind would race. Once I got a great view down her blouse and for a moment I thought she was braless. But she wasn't.

I decided to find out if she was watching me. I started staring at her but looking away if she saw me. I was hoping she would notice and think I was trying not to get caught.

Then one day it was my turn to open the store before anyone got there and start setting up. I was crouched down stocking a bottom shelf when I saw her standing right in front of me. She was wearing a shorter skirt thsi time and I could see right up to her panties, I couldnt look away and was sure I would be fired.

But she just kept standing there smiling and we began talking. I stood up and she reached out and fondled and rubbed my bulge as she spo9ke. That was it. But after that I saw her watching me even more.

And then she began flirting with me but in secret so no one else would see. I enjoyed thsi forbidden work place flirting but was afraid of going to far and ending it.

Then came the day she called me into her office.
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So I sat down in the chair on the other side of her desk. She was wearing a buttondown shirt but now had several buttons undone. She leaned across her desk and supported herself on her elbows. The opening of her shirt fell open letting me see everything. She had on a skimpy lace bra. She started by asking how I enjoyed working there and then proceeded with my job review. All the time letting me oggle her tits.
When the review was done, she siad, "We both know that we have been staring at each other so lets not pretend anymore." Her foot went to my crotch and she pumped. I came in my pants. She pushed her bra down so I could see her nipples. "But we have to keep thsi between us". After that we began having more fun than ever.
Oh yeah. She is married and has two daughters. One 20 and one 16.
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chase151992 Novice Jackinchatter

25 posts since 2012-11-20
33 year old
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You lucky son of a bitch. Props to you man. Bagging a cougar is something that is on my list.
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I will tell more later in the week.
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SloStroker Omnipitant Jackinchatter

7249 posts since 2006-08-21
52 year old bisexual male from Nashville, TN
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Never dip your pen in the company ink, but if you're young, single, and can find another job quickly....enjoy yourself.

Maybe you can do what a friend of mine did. He fucked his boss and then fucked her daughter.
Check out my porn blog at https://slostroker.bdsmlr.com/ and my writing blog at https://slostroker.wordpress.com or catch me on Skype as SloStroker
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seatledude777 Amateur Jackinchatter

111 posts since 2012-10-23
60 year old curious
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fuck man.... I'd to be in your shoes !! [email protected]
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Once at closing time I was on my way out the door and she called me into her office. We were the last ones there so she had me get under her desk and eat her out. Gawd I was in heaven!! And without warning, she peed in my face. Made what we were doing even hotter. I liked her dry after that. After we cleaned up the floor we went out separate ways. Luckily it was dark so as I went for my car, no one could see how the front of my shirt was soaked with delicious pee.
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SloStroker said:
Never dip your pen in the company ink, but if you're young, single, and can find another job quickly....enjoy yourself.

Maybe you can do what a friend of mine did. He fucked his boss and then fucked her daughter.


I did have a near encounter with her daughters. But not quite. I will tell the story at a later time.
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JohnnyAplSeed Novice Jackinchatter

71 posts since 2008-11-08
46 year old from southern Maine U.S.
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ya had my attention till the pee part. frown why ya gotta make stuff up?
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Why would you think I made it up?? I have read lots of stuff here on Jackinchat that is way more "out there" than what I am doing. Besides, some people like pee games. There is lots of that stuff on here. I am sure you do stuff that I don't like, but I won't accuse you of making it up and I won't look down on you. Each to his own.
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MrLookieLou Amateur Jackinchatter

353 posts since 2010-10-14
52 year old heterosexual male from San Francisco
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JohnnyAplSeed said:
ya had my attention till the pee part. frown why ya gotta make stuff up?


yeah...how would anyone not notice their shirt was soaked in urine?
Insatiable
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MrLookieLou said:
yeah...how would anyone not notice their shirt was soaked in urine?


It was dark meaning it was late. It was after closing time meaning no other staff was around. But if no one is going to believe what I say I won't say any more. But if you doubt my story, why are you on this website? As I said, there are lots of stories that are harder to beleive than my rather tame tale. If you don't wnat to hear more, your loss.
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boxingoscar Amateur Jackinchatter

469 posts since 2012-01-21
71 year old curious
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Ignore the doubters. Just keep telling your story.
I pity a man with short arms.
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Thanks boxingoscar. I came back to see if I had any support. If I didn't I was going to leave, but thanks to you I will continue. As long as I have more to say. And I do as of yesterday ..... stay tuned.
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I found out I am her ... plaything.
So yesterday we had been eyeing each other all day. She wore a business like pencil skirt that showed her slim curves. But at the end of the day she called me into her office and said she saw how I was ogling her two daughters the day they came to see her at work. I figured I was in shit with here, but she told me to take off my shirt, push my pants and underwear to my ankles and sit in the chair across from her. Whne I sat down my dick began to grow and her eyes was riveted to my boner. She began telling me how a few years ago her hubby began hanging out more with his buddies and ignoring her. She was beginning to think of leaving him when she found his porn stash that showed what he and his buddies were up to without her. Then I came along and she decided to have her own fun instead. She then asked what kind of porn I was into. She said that as I told her she wanted me to be jerking my dick. As ran off a long list of my interests and she asked questions about them. Like have I ever done the webcam thing? I haven't but I do have a webcam. Or have I ever bukakkied a girl?

Anyway I sat there for half an hour stroking my hard on as we spoke and she watched. We were both getting off. The phone rang and it was her youngest daughter. She kept watching me as she spoke to the girl. She motioned for me to come over but stay quiet. As I stood there and she talked to her daughter she jerked me off and I came on her bare shin. The she motioned for me to lick the cum off her as she talked to her daughter.
She had me get dressed and we left and she actually called me her plaything. I am not complaining at all ... I wonder what will happen next??
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