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Confessions of a Show-Off: Pt 1. The Start

Posted by: Age: 40-something Posted on: 5 comments
10 likes 27 views Category: Masturbation Male-Female Tags: Male-Female, Masturbation Male-Female, watching, masturbation, male-female, show-off, public

A curvy intern awakens something in me.


My name is Tim and I like masturbating for an audience.  Everybody has something that makes them different than most of the crowd, and I guess that is mine. I love to show someone how hard I get when they watch me stroke. It's always consenual, I never show my cock to someone unsuspecting.  This is the story of how I discovered this hobby. I was a mid level manager at a architecture/engineering/construction firm in the Southern part of the US. I was in my early 30's and pretty career-focused. When I was at work, I was working hard and trying to climb the corporate ladder. I am an introvert by nature - as weird as it might seem that an introvert likes to pull out and jerk off for strangers, it's true.  My job required me to interact with people all day long and I rarely had anytime to myself.  Whenever I could, I would spend my lunch hour at a local park, just trying to grab a few minutes to myself to decompress.  Sometimes I'd walk around, but mostly I'd park under a shade tree in the back cornor of the parking lot, ease the seat back, turn on some music and just relax for an hour.  We had hired several interns for the summer and I was stuck with one over-enthusiastic girl who was assigned my department.  She was bubbly, talkative, had a tendency to ramble on and ask off-the-wall questions that had nothing to do with the subject. She was annoying. She was also, pretty hot.  5'7-ish, curvy, nice legs, blonde, and large bouncy tits.  But, I kept it professional and tended to keep our interactions short and all business.  One day, I had a morning meeting that started at 7AM and ran through 10:30. Afterwards, I went into my office and Intern Girl was there, waiting. "Shit", I muttered to myself.  It was my day to give a lesson on an aspect of the business. So I ran through a quick generic speech as quickly as I could, got up, grabbed my keys and was escorting her out of the office when she asked "What are you doing for lunch?".  "I'm not hungry, I'm wasn't planning on going anywhere" I responded.  She looked at the keys in my hand and back up to me as if to say "really?".   "well", I explained "some days I go over to the park and just relax by myself for a bit".  "That sounds fun! Can I come?".  Really? what part of 'by myself' was she not understanding and who invites themselves along?  But my head was fried and I thought I could at least look at her tits for an hour while she rambled on about something. "Sure, come on". We park under the tree and she starts in on talking.  I zone out. Her fiance is deployed in the Middle East, she misses him, blah blah blah they can only speak a couple of times a week via webcam..yada yada yada and then "but I enjoy watching him jack off".  Wait, what? this really isnt appropriate conversation, but I asked "He...jacks off on camera?"  "Uh-huh, and I show him my boobs and ass, it's fun!" she answered.  I managed to get out "OK, well,cool" not sure how to respond.  "It's a big turn on for both of us. I like men looking at me, i guess i should have been a stripper hehehe".  So, I'm imagining her naked and there is a stir in my pants. She continued "in fact, dont tell anyone, but I go into chat rooms and turn on my cam and let anyone see, I think its hot knowing people are jacking off to me, thinking of me...".  I really shouldn't be having this conversation, I kept thinking, but my mind was racing as fast as my pants were tightening.  And then she said something I would never forget. "I would actually like to see some one jack for me live and not just on camera one day".  I looked surprised at where this had taken us, and against my better judgement I said "well, we have 30 minutes left...".  It was her turn to be surprised. "You mean here?" she asked while looking around the parking lot.  I laughed, said I was joking and as was just about to change the subject to something else when she said "OK!".  She then just took off her blouse and then her bra, and turned in her seat and looked at me, smiling. I think she was smiling, I was staring at her beautiful round D cups that she was tracing with her fingers.  "Well, your turn" she said.  I looked around and wondered how i got myself into this...and unzipped my pantsand slid them down a bit.  I rubbed my now fully erect cock through my underwear and said "so...uhmm..what...uhmmm".  She laughed and said "I showed you mine, now you show me yours" and pointed to my cock.  I slid the boxres down, grabbed the base of my cock and kind of waved it at her.  She leaned closer, smiling, and told me it was pretty. "thanks..so..you just want to..." I wasn't speechless, but I could see it from where i sat.  She grined, and purred in my ear "make it cum for me, please".  And so I slowly started stroking up an down the shaft.  I squeezed upward and let some pre-cum slip out and smeared it around the head. She moaned, and was pinching her nipples.  I don't ever remember being as hard as I was at that moment. My cock was throbbing in my hand. I leaned toward her and whispered "see how hard you made me, how bad my cock wants you"?  "mmmuh huh" was all she said. I stroked faster, she started bouncing in her seat a bit, making her titties bounce and sway.."do you like them, do you like my tits?" I nodded that I did, "well show me how much you like them" she purred in my ear "cum for me, I want to see it" and then she slide her tongue in my ear.  That was all it took. I shout a ropey length of seed n the air and onto my shirt. The next shot hit her right nipple. I lost track of the rest.  And that is all it took. I was hooked on stroking for someone.  Her and I 'went to a lunch' a couple of more times that summer, and i never saw her again.  But it started a hobby of sorts that has lasted almost 20 years. I might write about other women and men who i have stroked for, if anyone is interested.

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