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Unlikely Catch  

CaptainAlex10 56M/53F  
9 posts
2/16/2015 2:21 pm
Unlikely Catch


I went to her house to pick up some papers. We were colleagues consulting to the same firm. Her two both had colds and her husband was out of town so she was working from home. I knocked on the door and she answered looking pretty tired. Normally she was an attractive late 30-something with highlighted blond hair, body that would look great in a bikini, and nice skin. We’d never really flirted at work, but we were friendly and often enjoyed a good laugh. She was one of those people who easily laughed, even if it was at herself. This made her friendly and affable. Just as she answered the door I heard a cry from upstairs. She looked at me like “help!’ and said the folder is on the dining room table, pointed to the dining room and turned to run upstairs. I felt a little awkward in a stranger’s house just letting myself in to dig on her table. The dining room table had a number of stacks of papers as did the coffee table in the adjoining living room. Knowing what her desk looked like at work this didn’t surprise me. But finding a file in all this stuff was going to be tough without becoming more intimately acquainted with my colleague. There was some order to the piles. There seemed to be piles of ’s stuff, pediatrician’s reports and bills. There was another pile of stuff that seemed to belong to her husband (ah, so he is the same way). I dug around and didn’t find the folder or the pile of stuff related to our .
I looked around to the coffee table and saw a couple more piles. So in an effort to remain busy, and get out of her hair as quickly as possible I started working through the coffee table. As I lifted a small stack of magazines off the table, revealing the work pile I was looking for, to my surprise and embarrassment a translucent blue vibrator feel out of the pile of magazines and went rolling across the floor—right up to her foot as she appeared in the doorway. She turned several shades of red, bent down so fast to snatch up the toy that she hit her head on a chair beside the doorway. I immediately went over to her to see if she was ok. She was just about to cry.
“Are you ok?,” I asked.
“Yes. Just mortified. I am so sorry. This is so embarrassing.”
I said, “No. Your head. Is your head ok. I don’t care about the toy. Though I did find it funny,” trying to get her to laugh. She laughed.
“Everybody does it. Nothing to be embarrassed about,” I said, now trying to relieve her embarrassment.
“What?”, she said. “I am sorry. Its supposed to be a private thing. My damn dildo is not supposed to go rolling across the floor in front of a stranger!”
“Who are you calling strange?” I said. Eliciting another laugh from her. “Besides it doesn’t always have to be private.”
She smile awkwardly. I figured I’d gone too far. She put the vibrator in her purse and came over to the coffee table to help me find the file.
She found and handed me the file. “Is this the right one?”
I opened the file and confirmed it was what I had come for.
“What do you mean ‘it doesn’t always have to be private’?”
Now I was embarrassed. She’d caught me off guard.
I stammered a little, but got out that masturbation can be fun with other people around. A little voyeurism/exhibitionism between consenting adults can be fun. She asked if I did that often. I said that I had friends the enjoyed it. I didn’t mention that I play on cam on the Internet for people I’ve never met. Her face was a look of amusement, curiosity, and that tired look she had when she answered the door. She said “I am so stressed with all this work, the being sick, and Ted being out of town, I just need to relax once in a while.” I said that I understood and that with the deadlines at work I often have to get a release. She asked “Do you really do it while people watch?” again. I said I did, that it made it more sexy, a little more like real sex but without the time it takes to have a date, seduce, spend the night, etc. She laughed again. “I think it’d be sexy to watch and be watched,” she confided.
I wanted to ask if she wanted to play together right then, but I didn’t want to push it. She was vulnerable and we were colleagues and I don’t usually get involved with work people—even though she didn’t for me or in my area. I told her that if she’d like to watch there are lots of people on the Internet who play on cam…she could watch guys, girls, couples, whatever. She misunderstood me to mean porn, and I corrected her that there are online cam chat where you can play with a person directly. I could see this was getting her attention. “No! Come on. Really,” she said. I said sure. “I don’t know if I could do that,” she said. I told her she should give it a try and if she didn’t like it, she didn’t have to do anything. She told me that she couldn’t risk anyone knowing who she was. I told her that that was important to both of us and she agreed. “So you cam with people online?” she asked. I realized I’d let the cat out of the bag so I, trying to figure a way out of it, said yes, that I did sometimes. “Come on. Show me” she said. I said “What? Jerk off or what you can find online?” This embarrassed her again and she said “I meant what I could find online. But if you want to show me the other that might be fun too.” The ice was broken.
I took the indirect path. I asked her where her computer was, and she showed me her home office just off the kitchen. It was a cozy little room piled high with what I had already come to know was her organization style. I asked her why she didn’t bring her toy and she looked surprised and immediately left the room and returned with her purse withdrawing the blue plastic cock from it as she entered the room. I brought up Watchers Web and logged on. There were the usual sexy cams…ladies in various states of undress. She watched the chat scroll across the screen. Flirt79 was on screen and the cam scanned downward to reveal her sexy body and shaved pussy. I could feel Jenny loosen up as she saw the naked body. “Wow” she said “I see why you’d get off on this. Do they have guys too?” I said “of course” and scanned the chat to see who was getting most attention from the girls. I brought up “Watch Couple,” knowing that usually it was the guy with a decent body stroking his cock. He didn’t disappoint. She gasped, “Oh my God. Look at that.” I smiled as I nodded. She pulled up a chair and relaxed into it. I could see the stress melting off her body. I saw where this was going and I asked about her . She said they’re upstairs in bed and asleep. I pushed the door closed just in case. We was dumbfounded watching the guy slowly stroke his cock on cam. I was having trouble sharing my attention between her relaxing and Flirt79 who was fiddling with her dildo between her tits and licking the end…as I wish she was licking mine. I must have let out a little gasp as Flirt79 panned down to her pussy with the dildo positioned on it. Jenny smiled and touched her pussy through her jeans. I said “go ahead. I won’t mind.” She said, clearly blushing, “No. You first.” I responded, “I can. That is really hot.” She smiled and nodded. I started to undo my pants and she watched as I slid my zipper down and undid the button. My cock stood hard in my boxers. She let out a little moan and just as Mr. WatchCouple stood up. She seemed to instinctively stand up with him and unbuttoned her pants and slide her zipper down and put her hand into her pants. “Wet,” is all she said, to no one in particular. I smiled as I grabbed my cock through my boxers. Her wet pussy was a foot away from my face through a pair of black silky panties. I could just about feel her heat. The threw her head back as she moved her hand so it went down her panties to her pussy, her other hand on her right breast under her shirt. This was getting good. Flirt79 had a dildo in her sexy pussy and Jenny was right next to me about to do the same thing. My cock came out of my pants and I started to stroke it. Jenny looked down and gasped again. “Oh my God. You are doing it! That is so cool” as she drove her pants to her knees along with her panties, took her shirt off over her head and sat back down in her chair to enjoy her pussy. I said “I love this view.” She smiled and licked her fingers that had been in her pussy. I said “do you have a cam. There are others on here who’d love to see that.” She looked astonished, “Oh my God. No. But could I really do that?” I asked her what she thought these other people were doing. I think if she wasn’t irrationally playing with her pussy at that moment she would have put a webcam on her shopping list.
I watched her and I watched Flirt. Actually, sorry Flirt, I spent more time watching Jenny in the same room. She was deep in her own pussy. I was stroking my cock watching her. I stood up for a moment and reached across her to the table behind her for her dildo, which out my cock within striking distance. She grabbed my cock and slid forward on her chair taking my cock deep into her mouth. I gasped for a moment. That wasn’t the plan, in fact, the plan was pretty much mutual masturbation – after all I worked with this woman. She played with my cock with her tongue. I resigned myself and started her vibrator and starting at her navel, moved it down to her clit. She hummed approval on my cock. Her hand returned to her pussy and I touched the vibrator to her hand so she’d feel it inside on her hand. She moaned and I could tell from her attention to my cock she was about to cum. As she came she took my cock from her mouth and stroked it half heartedly as her attention was on her own orgasm. She came what felt like twice, then she pulled me closer and kissed my belly and pulled me down to her. We kissed and she continued to work her pussy and stroke my cock. She pushed me back on the chair I had been sitting in. She stood up and straddled my legs still holding my cock and aiming right for her pussy. A drop of pussy juice fell on my cock and I about exploded. She sat on my cock, penetrating only a little at first and slowly sliding her whole wet pussy down my hard throbbing cock. Flirt79 continued to play with herself as did Mr. WatchCouple. It was as if they were watching us…that would have made it even better. As my cock bottomed out on her pussy she came again and I could feel her juices gush around my cock and she moaned gently. She touched her clit while my cock slide in and out of her pussy. Another orgasm. She continued to ride my cock. She continued to cum. Finally, as I wasn’t about to take any more of this without cumming I told her. She said, “I really want to see this” and she stood up and sat back in her chair still rubbing her wet and now even a little red pussy. Her little landing strip of hair was sopping wet. I thought how nice it would be to taste that pussy right now and as I did that my cock squirted cum all over my belly and up to my chest…almost to my chin. She came again as she watched. She sat back, now completely relaxed. She no longer looked harried or tired. She literally glowed. Her skin glistened. Her hands moved slowly over her body. She looked over at me and smiled. She looked at the cum on my chest and smiled and said something about needing to clean up. I told her not to worry about it this time. She smiled again. I found some paper towels within reach and cleanup my mess. She didn’t move. She just lay there. As relaxed as could be. We hardly spoke. I eventually got up and put myself back together, packed my cock into my shorts, and back into my pants along with my shirt. I think she’d fallen asleep. I didn’t have the heart to wake her. I stood up, kissed her forehead and let myself out of the office<b> locking </font></b>the door again behind me. There was no sound from upstairs so I figured she have some peace before the needed her again. I started out the door then remembered the file. I went back to the coffee table. I remembered the dildo falling out of the magazines as I moved them aside again and I smiled. I took the file and left the house and went back to the office – myself very nicely satisfied as well. No day could be a bad one after that.

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