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trump4prez Amateur Jackinchatter

118 posts since 2016-03-16
31 year old
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I'm 25 and at my office there are quite a few attractive ladies over 50.

One was actually a former model in the 1980s/early 90s and is now a VP probably raking in north of 200k. I once jizzed in my pants when she was wearing a really short skirt showing off her long legs in heels combined with her big tits and beautiful face. Is it normal to fantasize over being a boytoy for one of these beautiful powerful ladies in the office?

Maybe twice a week, I need to rub one out in the bathroom so bad in order to focus on work. Who else has had similar stories?
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ILikeNiceWomen Novice Jackinchatter

38 posts since 2013-06-02
heterosexual
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I totally know what you're talking about. I worked in a place like that for 3 years and had a hard on cock every day at work. I lived close to my work at the time so I would go home at lunch and rub one out stroke
Gotta love tits!
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NorCalMan Skilled Jackinchatter

558 posts since 2015-05-14
67 year old heterosexual from NorCal
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I worked in a restaurant when I was 19. The owners wife ( 35ish) had huge tits and would flirt with all the young guys. I would jerk off every night fantasizing fucking her.
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Boris21 Enlightened Jackinchatter

2530 posts since 2016-11-28
28 year old bisexual male
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I have a 40yo MILF co-worker who loves to wear sweaters, tight skirts and nylons. She's about 5'6" and I'd guess a 36C. I have to excuse myself and go JO several times a week.
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thickboner4u Professional Jackinchatter

1030 posts since 2008-10-07
70 year old curious from KY
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When I was in college in the sixties I worked at night in a mailroom sending out orders with a MILF who had the biggest tits I had ever seen. She always wear a t-shirt to work and a bra that could barely contain them so they jiggled and shook when she worked. There were only three guys and her that worked at night and she was a constant flirt. She knew that we love seeing her tits jiggle and made no attempt to conceal the fact that she enjoyed the attention. I would often leave work and sit in my car and jack off I was so hot and horny after spending the evening with her. None of us had the nerve to make a move on her since her husband was a captain in the local police force.
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trump4prez Amateur Jackinchatter

118 posts since 2016-03-16
31 year old
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Had to bump this up. That same former model got promoted to senior VP the other day. Had to rub one out so bad after I heard that.

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Jethreaux Novice Jackinchatter

15 posts since 2018-07-07
58 year old curious male from N.Illinois
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When I was 16 the place I worked had a blonde,early 30s, that was thin and nicely proportioned and a brunette, late 30s, whith large breast and nice full ass, they drove me wild. I would slip into the bathroom to jack off several days a week.
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phiilip Professional Jackinchatter

1026 posts since 2011-05-08
68 year old bisexual from UK
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Jethreaux said:
When I was 16 the place I worked had a blonde,early 30s, that was thin and nicely proportioned and a brunette, late 30s, whith large breast and nice full ass, they drove me wild. I would slip into the bathroom to jack off several days a week.


There are plenty of mature women who'd be happy to have sex with a guy of that age.
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I'm in my 50s myself now, but in my first proper job, early 20s, I worked alongside a lovely blonde woman in her 40s, slim, small breasted but gorgeous. Nothing ever happened, but I came most days thinking about her!
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brutpolo Amateur Jackinchatter

304 posts since 2016-10-15
67 year old curious from Dallas, TX
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Back when I was in my mid twenties, worked as a manager in retail business and there was a lovely, petite redhead who was married and 42-43 years old who worked the stores adds, promotions, etc. Much of the displays back then were still hand done. She had an office and layout area on the second floor, off of the stock area. A luvly lady, petite, smooth creamy skin and smallish perky breasts. I used to make a point to get up to the stock area daily and always timed it when I knew she was in her work area to stop an talk to her. Got a bit flirty at times. One day as I was leaving her area, she was sitting at her work station,I bend down and kissed her on the cheek. The reaction was kind of "surprise" on her part. Neither of us said anything. Soover the next few weeks, I did the same kiss on the cheek, with the same reaction. Then, I got the surprise...as I went to kiss her on the cheek, she turned and met my lips full force with lips and tongue. Damn, I was paralyzed as we sucked each others lips, mouth tongue and hands all over each other. Picked the right times and sucked and fucked each other a half dozen times over the next few weeks. Met a few more times at motels. She changed jobs and I changed store locations, so it died down.
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Feminine_MaleLesbian Professional Jackinchatter

1088 posts since 2015-04-17
56 year old heterosexual from Louisville, KY.
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I have had many milfs to fantasize about and jack off to from different jobs in my life.
Love stroking with the women in person, on the phone or on webcam.
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daval Professional Jackinchatter

2239 posts since 2015-04-28
73 year old bisexual male from Aberdeen, Scotland
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I'm retired now, but have many memories of attractive women I've worked beside over my working life. Even from when I was about 16 working in the local farmer's garden. His daughter in her late 20s used to tell me what jobs needed doing and occasionally helped. She was not much of a looker but was buxom with big tits and thick curvy legs. I remember to this day that one time as we weeded, she was wearing black stockings and suspenders. I got the occasional glimpse up her skirt. I wonder now why she was wearing and why she helped me that day. May be she knew I would get turned on and wank later which I did of course. I wonder if workers these days take sneaky pics on their phones of female work colleagues?
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You should sneek some pics of this VP so we can all enjoy stroking to her with you! Always fantasize about powerful mature women!
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pics_spunker Novice Jackinchatter

34 posts since 2018-05-03
70 year old
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What about female teachers or even the principal of the school? Powerful and often sexy I soaked many a pair of pants rubbing my cock under the desk to the cleavage or the glimpse of nylon-sheathed thigh. Try this one for size or maybe too old for this thread
http://www.slutwives.com/threads/is-the-headmistress-too-old-for-porn.86656/

Pm me if you'd like more pics of her.
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tp_cain Skilled Jackinchatter

666 posts since 2017-09-01
54 year old bisexual male from East side Metro Detroit
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I worked at the local, small, family-owned grocery store when I was in high school. Nothing there even remotely attractive...except the guy I was working with. I'm not into guys and I didn't find him attractive, but he was already my suck buddy by then.

Joined the army after high school. Plenty of woman to jack too there, though only a few were REALLY nice.

After that, I wasn't really "young" any more. At this point in my life, I could jack off to a tree, if the bark pattern happens to be shaped like pussy lips, or a knot happens to look like a crinkled butthole. Yup, that's really where I'm at in life. :sigh:
Paul
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