Posted on 2021-02-05 07:31 PMalpinedude said:Wow, since so many people like my boss, I worked up the nerve to grab a few screenshots of our last meeting (while I was jerking of course). Let me know what you think!
Also, her professional headshot in case anyone wants to jerk to it:
Posted on 2021-02-05 08:24 PM
tinypenistom
105 posts since 2021-01-04
53 year old from Wilkes -Barre, PA, USA
God you guys have me so hard right now.
I just have to tell you that you got me in trouble just now.
I was reading about the bosses and zoom jerking.
Of course I am playing with my tiny chastity caged penis, a call comes in over the zoom on my laptop, it was my insurance agent.
I didn't think and answered the call, she was on video and saw me sitting there (in my pretty pink chastity cage) playing with it like a teenager in heat.
She is in her 50's, very professional and a hot, horny MILF. She looked, smiled and said "I just took a few screen shots and this call is being video recorded, be in my office Monday, ready to receive punishment or I show the photos and video to your wife and some others." I asked that she not do anything that will get me divorced or really in trouble, then I asked what kind of punishment she planned to give me. She said "Let's just say you won't have to worry about sitting down or using the crapper for a few weeks and our jaw will be stuck open for a while too". (Translation: I know that means a severe spanking and lots of butt fucking in addition to the sucking and eating my jaws will be doing). Thank you guys.
tinypenistom
Posted on 2021-02-07 08:54 AM
alpinedude said:Also, her professional headshot in case anyone wants to jerk to it:
bloody hell... that professional headshot is made to be cummed to
Posted on 2021-02-08 12:59 PM
alpinedude said:Also, her professional headshot in case anyone wants to jerk to it:
This thread has quickly become one of my favorites on this site. This boss in particular has drained my cock more than a few times.
Posted on 2021-02-08 01:08 PM
perve2point0 
942 posts since 2020-06-24
58 year old bisexual male
tinypenistom said:
God you guys have me so hard right now.
I just have to tell you that you got me in trouble just now.
I was reading about the bosses and zoom jerking.
Of course I am playing with my tiny chastity caged penis, a call comes in over the zoom on my laptop, it was my insurance agent.
I didn't think and answered the call, she was on video and saw me sitting there (in my pretty pink chastity cage) playing with it like a teenager in heat.
She is in her 50's, very professional and a hot, horny MILF. She looked, smiled and said "I just took a few screen shots and this call is being video recorded, be in my office Monday, ready to receive punishment or I show the photos and video to your wife and some others." I asked that she not do anything that will get me divorced or really in trouble, then I asked what kind of punishment she planned to give me. She said "Let's just say you won't have to worry about sitting down or using the crapper for a few weeks and our jaw will be stuck open for a while too". (Translation: I know that means a severe spanking and lots of butt fucking in addition to the sucking and eating my jaws will be doing). Thank you guys.
That's some wide angle cam you have on your laptop.
Posted on 2021-02-19 04:06 PM
justadude 
73 posts since 2014-12-13
33 year old
Jerk to her on zoom calls all the time!
Posted on 2021-02-19 05:31 PM. Last edited by MWankin on 2021-02-19 05:31 PM. (1 edits total)
MWankin
177 posts since 2015-01-11
72 year old curious male from D.C./Maryland
justadude said:
Jerk to her on zoom calls all the time!
I would too! A real shame I'm retired. No one invites me to jerk to them under the Zoom mtg table. If they did the carpet would be ruined, lol.
You think the pic of your boss with the donut & her mouth opened means she wants her face glazed like that?
Posted on 2021-02-19 05:32 PM
MWankin
177 posts since 2015-01-11
72 year old curious male from D.C./Maryland
alpinedude said:Also, her professional headshot in case anyone wants to jerk to it:
Jeezus.. tell her your next load is a proxy for my cum load!
Posted on 2021-02-19 06:23 PM. Last edited by MWankin on 2021-02-19 06:27 PM. (6 edits total)
MWankin
177 posts since 2015-01-11
72 year old curious male from D.C./Maryland
How I'd like to see her, lol. Just a quickie.
http://pixxxels.cc/gnFhs0Cy Posted on 2021-02-19 06:27 PM
Unregistered
I am retired from work now, but when I was working I had a very cute female boss, wonderful body and she always wore knee length skirts, used to drive me crazy.Saw her a few weeks ago at a store, and its been about 4 years since I saw her last, and sadly she had put on a lot of weight, had to stop myself from saying what have you done to yourself lol.
Posted on 2021-02-21 07:34 AM
anyone who is sharing such voyeur experiences or fetishes? I am online on skype right now. arthur13506
Posted on 2021-02-25 11:55 PM
Unregistered
need2cumbad said:God I do this all the time. My boss is so demanding and a total alpha woman, I love jerking to her during our Zoom meetings. She has no idea how much she makes me cum during our calls... Here's a few pics to give you an idea...
Incredibly sexy. Love the short hair and incredible legs. Would definitely love to fuck her. The fact she's an alpha only makes it hotter to ravage her.
