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Confessions of a Show-Off: Pt 2, Chat Room

Posted by: Age: 49 Posted on: 3 comments
6 likes 20 views Category: Masturbation Male-Female Tags: Male-Female, Masturbation Male-Female, masturbation, show-off, watching

A Local MILF in a sex chat lets me show her close up.


The late 90’s on the internet were a fun time. Adults discovered that they could converse on a variety of topics with likeminded adults around the globe. As will happen, the topic was often about sex and sexuality.  I was a frequent chatter, at the time, in a chat room, which if I’m not mistaken was just named ‘sexchat.com’ or something similarly straight to the point.  I was at the early stages of my discovery of the joys of masturbating in front of someone, and this place seemed to help scratch that itch.  I soon met a local woman, and we hit it off. She lived very near the neighborhood that I grew up in, and we shared a lot of common interests. We were roughly the same age. She was tall – 5’11” – had a couple of kids, curvy with a pretty face. She also had a pretty pussy. As opposed to typical ‘cyber sex’ (i.e. ‘I slowly unbutton your shirt…..’) we would discuss sex, what we liked, what we would like to try, what we hated.  We would send each other pics, we would web cam when we could get a free moment together. I loved jacking for her live, and equally enjoyed seeing her pleasure herself.  She was married, and this was her outlet for not cheating.  One afternoon, we had each other turned on pretty good.  “I wish you could see how hard I am for you” I said. She responded that It was driving her crazy that my cock was throbbing for her, so nearby, and she couldn’t do anything about it. I suggested we meet.  She balked, “I’m not going to cheat”. “We meet, all I’ll do is pull out and stroke for you – you just sit and watch. Nothing else expected, nothing else will be asked for” I pleaded, trying not to sound too desperate.  She agreed, and I hopped in the car for the longest 20 minute drive of my life.  She was in her car waiting when I arrived at the agreed upon spot.  I jumped into the passenger side. She was prettier in person, and the conversation was as easy as it had been online up to this point.  “No touching” she warned.  “No touching” I agreed as I unzipped my jeans.  My cock had been hard or semi hard for the better part of two hours at this point.  Pre cum had already leaked and my cock head was slick.  There was something about her just sitting there, looking at me. I didn’t touch myself after freeing my cock, but it grew from semi to fully hard with just her stare. “damn, it’s nearly doubled!” she observed.  “well, that’s your fault” I said as my cock visibly throbbed and twitched. I slowly spread precum across my head and let my hand slide down my shaft to my balls, and began a slow rhythmic slide in and out of my fist, like I was slowly fucking my hand.  “want some motivation?” she asked, without breaking eye contact with dick. I was pretty obviously motivated, but what would a little more motivation hurt? “Sure”, I responded. She hiked up her skirt, with no panties on, and revealed a perfectly shaved wet pussy.  She was walking close to the edge for someone who didn’t want to cheat.  She spread her lips and began to pleasure herself.  I fought back the urge to cum where we could enjoy this a bit longer.  “Where are you going to cum?” she asked.  I told her that I hadn’t really planned that far in advance.  She didn’t respond. We both increased the pace a bit, watching each other in silence, until finally I said “If the situation were different, I’d cum in your pussy – fill it full and make it mine”.  That seemed to do the trick as she stiffened and shouted “OH FUCK!”.  I honestly don’t know how I didn’t cum when she did.  Maybe it was just the fascination of watching someone pleasure themselves, or maybe it was the fact that I really wanted her to watch me cum…to see my need for her on display. After she recovered a bit, she leaned over the center console with her head on my chest, watching me jack and throb.  My left arm draped over her back, her fingers dancing on my thigh, inches away from my balls.  “You are so thick” she sighed, “do that thing you were doing, where you fucked your fist like it was a pussy”.  We added some more lube and I gripped the base and begin thrusting my hips up and down.  Each upthrust had the tip of my cock inches from her mouth.  “make it tight, like my pussy, show me how you’d fuck my from behind” She commanded, as I began to fuck my hand quicker, my climax cleared for final approach.  “I like being fucked doggie style, and I like reaching back and playing with balls..” she stated and she cupped my balls…her fingers pointing south. I didn’t remind her of the ‘no touching’ rule. My left hand started playing with her hair as she said “You can’t cum in me, but you can cum on me today”. I gasped, the orgasm was inevitable and fast approaching. Her fingers traced their way south, I gripped her hair harder as I pistoned in and out of my closed fist. When her finger tip finally found my ass, I came instantly.  I couldn’t see it for her head, but I knew that I had sent quite a load in the general direction of her face.  I slowed, and squeezed upward on my shaft, to my head, letting the last remaining semen find it’s way out.  I felt her finger trace my cockhead and then she placed her finger in her mouth.  We went from ‘no touching’ to eating cum…cool. She finally raised up revealing a line of cum from the bridge of her nose down past her chin, and all over her shirt. “wow” was all I managed to say. She giggled, licked her lips, and asked if that was better than the web cam.  It was. Much. We met a couple of more times after that and really pushed the boundaries of the “no touching/cheating” limits.  I suspect we passed them when we were 69-ing with my face smothered by her pussy and my cock at the back of her throat. 

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