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I love the summer months and almost daily freeball and wear baggy cargo shorts.
When I'm at work, I pull my shorts to the side before I sit down so I have easy access to my dick anytime I feel like giving it some strokes.
Yesterday, a 40ish milf came in and I stroked it constantly for 20 minutes as we talked and came in my hand as soon as she left.
Anybody else have experiences like this?
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joet Amateur Jackinchatter

248 posts since 2013-02-05
59 year old curious from US-New Hampshire
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i like baggy shorts and no uw too. shows the bulge better, and love getting into postitions where people can see. they think its accidental and i like seeing the looks on their faces. usually amusement/interest
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bigpete Amateur Jackinchatter

366 posts since 2012-12-15
80 year old
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I use to truck all over the us and Canada before I retired

one afternoon in Ft chiswell, va I was sitting in truckstop with shorts on not really paying attention to what was showing as I was leaving another guy came up to me and told me nice pair of shorts. I was lost til he told me wht had happened under the table.

it was a interesting evening
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nudist_jo Amateur Jackinchatter

147 posts since 2007-03-29
28 year old
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Loving going commando. Got me a nice pair of white mesh shorts I like to wear that leaves nothing to the imagination. Fun to wear around all my buds, see the looks on their faces.
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I also did some truck driving, but it was mostly short runs and I didn't have to refuel so I didn't stop in Truck Stops very often.
But, if it was warm weather I was wearing shorts and freeballing.
Played with my dick many times...kept an old sock close by to come in.
Had plenty of jacking material too...flashed by many women...even saw a few fingering their pussies...also saw a few guys stroking as they passed me.
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When I'm working from home I like to wear very thin pyjama-style shorts that are light in colour. Not only are they very comfortable without heavy/tight material on my cock but its also nice to answer the front door for deliveries with a subtle semi going on with the bulge visible under the cloth.
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Ready2Shoot Enlightened Jackinchatter

2931 posts since 2006-07-23
61 year old bisexual from Oregon
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WorcesterBloke said:
When I'm working from home I like to wear very thin pyjama-style shorts that are light in colour. Not only are they very comfortable without heavy/tight material on my cock but its also nice to answer the front door for deliveries with a subtle semi going on with the bulge visible under the cloth.


When I work from home, I just stay naked! Much easier to play with myself while working!
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that's hot, mrhandy
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boxingoscar Amateur Jackinchatter

469 posts since 2012-01-21
71 year old curious
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Love freeballing. Just bought a pair of mesh shorts. Tough to see anything unless you're close, but you could. Like this:

Blue mesh shorts
I pity a man with short arms.
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jack1566hard Professional Jackinchatter

2097 posts since 2012-11-10
55 year old heterosexual male from DC/MD/VA USA
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I do this too but I have to fdo it after work because feeling my cock flop around gets it hard and then I need to attend to it,. I like going commando in shorts and running errands. With every stop, grocery store, gas station, etc the more I walk the more it swings, the better it feels, the harder I get. The last time it was so hard that I drove it the peep show booths in the adult vid store and walked in with my raging hard boner clearly and now very publicly displaying. I got my tokens hit the porn booth and stripped and stroked. within a few seconds someone was at the gloryhole mouth open and sucking me off. came really really hard. just thinking about this has me stroking again.
Working it hard
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Hung10Cop Novice Jackinchatter

16 posts since 2013-08-30
43 year old
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I generally freeball all the time. Really the only time I wear anything under my clothing is when I go running. I will wear compression shorts then just to keep everything in place and not be obscene.
10.75x7 and 8 around the head
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JayGrimm Novice Jackinchatter

93 posts since 2012-09-25
71 year old bisexual male from Connecticut
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I love freeballing in cargo shorts in summer weather. My fav is driving on a long trip in the car. I open all the windows and feel the air blowing up the pants leg. In no time I have a "3rd leg" forming. I raise the pants leg higher until my cock is fully visible. Mmmmmmmmmmmm
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Always naked at home, even to answer door. When dressed, freeball all the time, unless I have to wear a suit for a business meeting. Then I sometimes wear lacy panties. They make me feel more confident and aggressive when negotiating with lawyers. I suppose some men will think this is silly, but it works for me.
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dontpanic2013 Novice Jackinchatter

13 posts since 2013-05-26
49 year old bisexual from Ireland
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Always freeball, jerked a couple of times to chicks I work with behind their back, have a handy hole ripped in my jeans pocket for easy access.
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Dwins Novice Jackinchatter

52 posts since 2013-03-25
33 year old bisexual male from texas
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I was actually freeballing in jeans today at a friend's house. I was lying on the couch with my legs up on the arm and whatnot. His dad came in and gave me a few doubletakes but I didn't think much of it. Then my buddy walks by and from that angle looks over to talk to me and starts laughing. Unknown to me, I had a small hole in the bottom of my jeans and you could see my balls very clearly. I just laughed it off and sat right the rest of the day. And stayed away from his dad.
In brighest day, in blackest night...
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