Being married 18 years I have occasionally fantasized about what it would be like to be with another women. When my wife left town last summer to visit her sister for 2 weeks I got my chance...
A woman with whom I work (Karen) and I have had a flirtatious relationship for several years. She is about my age (45) and not a real 'looker'. At 5'5', about 160 lbs, green eyes and brown hair, she could best be described as plain. However her personality makes up for her lack of beauty. Bubbly, outgoing, curious, and definitely into the back-and-forth sexual banter - just a fun kinda gal. We had always kidded about going out for a few drinks to get to know each other outside of work, however my circumstances and hers (single mom of a teen son) never allowed us to go beyond the office flirting. Until I found out that her son was away at camp at the same time my wife was traveling.
We conspicuously arranged to meet for dinner at a restaurant close to the office (and within 10 minutes drive of each of our homes). I had all kinds of nasty thoughts swirling through my head as I drove there. Dinner was fun; we shared a bottle of wine, talked a lot about our backgrounds, families and friends, and Karen lamented several times about the lack of a man in her life and how lonely she gets. During coffee and dessert I wondered to myself what, if anything, might happen next when Karen mentioned that I could stop by when we were done so she could show me her recent home redecorating project. Of course I took her up on her offer and followed her home.
As we entered her home I noticed how welcoming and inviting the decor was, and she had done a fine job with the new furniture and wallpaper. As she gave me a tour, she poured each of us another glass of wine and she brought me downstairs (she lives in a split level home) to see the rec room and adjoining office. The rec room featured a large TV and a large library of videos, which I immediately began to peruse. Karen stepped behind me with her breasts rubbing up against the back of my arm and said, laughing, 'I hope I didnā??t leave any of my dirty ones in there!' Sure enough on the bottom shelf, tucked away in a corner were about 1/2 dozen videos hidden by several volumes of encyclopedias. I pulled one out that was titled 'Self Pleasure Techniques' and as I turned saw that she was blushing. She blurted out, 'Well a galā??s gotta do what a galā??s gotta do, right?' I assured her it was not a problem, I understood what itā??s like to be lonely and that 'everyone does it'.
With that I put the tape back (my mind was of course reeling with possibilities at this point...) and followed her over to her home office. She showed me her new PC, which was equipped with a camera mounted on top of the monitor. I asked her how she liked her new PC (a Dell) and if she used the camera often. Again, more blushing and a moment of awkward silence until she said, 'Well, my sister and I talk online sometimes together, but mostly I use it when I'm in chat rooms'. This was my chance- 'What kind of chat rooms,' I asked? 'Well, you know Mike. You probably chat in some of the same ones' 'Ohhh, THOSE kind of chat rooms. Do you actually, um, show yourself to other people on camera? I always wanted to try that, but, you know, with the wife and kids around its tough'. She was smiling a mischievous smile at this point and said, 'Well, let's have another glass of wine and I'll show y'all (she has a southern accent) the rooms I like to chat in.'
She left to get the wine from upstairs and as she did I moved a second chair in position next to the PC. She was back in less than a minute. We were both dressed in work attire, me with a shirt, tie and trousers ā?? she with a red sweater and black slacks. She took the 'lead position' behind the PC with me immediately to her right, and our legs were touching - taking my growing excitement to the next level. She quickly logged into her chat area (MIRC) and brought up Netmeeting and switched on her camera to show an image of her and me sitting next to each other. 'Your sure you want to see this, Mike?' she asked? 'Of course!' I replied. I was semi hard at this point, and I had barely touched her or saw any hint of flesh. 'Well, hereā??s the rooms I usually go into' and she brought up a listing of rooms with the extension of 's-e-x' attached to them. There were many - teensex, familysex, bifunsex, marriedandlookingsex, and netmeetingsex. She clicked into netmeetingsex and she showed me about 70 people already in the room.
Instantly she received multiple requests for private chats. As she looked at the profiles of each, we talked and laughed about how they were all from men, and how they all sounded so horny. 'Of course they are,' I said. 'They're guys - we're ALWAYS horny'. She found that very funny, and I noticed that her free hand had worked itā??s way down into her lap - not doing anything, just resting on top of her crotch. She pared down the number of men she wanted to chat with to 3, and after about 10 minutes of back and forth messaging, she decided to 'netmeet' with a 22 yr old man from California. A few clicks later and he was up on the screen, wearing only boxers and a tshirt. He of course saw both Karen and I, and he wanted to know who I was. 'Just a friend, hon,' she typed. 'He wants to see what this online stuff is all about'.The man (more like a college kid - I doubt he was even 22) was keenly interested, and quickly wanted to know if Karen wanted him to take off his shirt. She of course said yes, she would LOVE to.
He stripped off his tshirt, leaving him in nothing but his shorts, and through his boxers his erection was pronounced, bulging, and leaving little to the imagination. Next he asked Karen to let him see her breasts since he was letting her see him in just his underwear. As his request was typed across the screen, she looked at me and I said, 'Hey, whatever you want to do. I don't mind' and I smiled at her. 'Isn't that what you usually do when you chat on here'. 'Well, um, well, yes, I guess so. But Iā??m embarrassed with you here. I don't want y'all to see my big old body'. 'Karen, donā??t be embarrassed. I would LOVE to see your body. In fact, I've dreamed of seeing your body for a LONG time. Really, swear to god. If you want to do it, fine. If not, I understand'.She hesitated for what seemed like forever. Then she said, 'Mike, I'm a closet exhibitionist and I get really turned on showing off on the computer. It's anonymous and it's fun and helps me, um, well, uh, you know, satisfy my urges. I feel really comfortable with you, so if you say it's ok then I'll do it.'
With that she sat back in her chair and lifted up her sweater, exposing her bra. While I had fantasized about her, I had never imagined how large her breasts were. They must have been at least 36D, and her bra was very sexy. It was white lace, low cut, and I noticed that the clasp was in the back. She held her sweater up, and her face was flushed, and our friend online typed a comment of encouragement and appreciation.'Take it all the way off!' he typed.She looked at me again and lifted the sweater over her head. I was in heaven. Her body was far from perfect, and she did have a bit of a belly, but seeing her there in her white bra and black slacks had me hard as a rock. She had a very sexual air about her.'Can I see your panties now?' Mr. 22 typed in. On camera he was massaging his hard on through his boxers, and it was only a matter of time before he took it out. Karen snapped out of her trance and commented about how lean his body was, and how 'erect his penis is'.'You mean he's got a big hard-on, right' and I laughed, and she laughed with me. She stood up momentarily to unbutton her slacks and then quickly sat back down. She eased the pants down her legs, revealing her panties. They were white as well, briefs, not terribly sexy in the sense they were a bit matronly, however at the moment they were VERY sexy to me. As she was folding her slacks and placing them over the back of her chair (like a good mom would) I noticed for the first time that her erect nipples could be seen through the material of her bra. When we both glanced back at her monitor we saw that her friend had removed his boxers and was sitting back in his chair with a very impressive erection - at least 7' in length and curving back towards his stomach. He was not yet masturbating, but was leisurely toying with his testicles. Karen seemed mesmerized by this, and as she sat forward to get a better look she crossed her legs with her left hand firmly planted between her thighs. I notice that despite her rather 'plump' build her thighs and legs were lovely, and where her thighs rounded up toward her butt her skin was smooth and firm. After gazing at her naked friend on the computer for a moment Karen looked at me and said, 'Mike, he's got ALL his clothes off, and Iā??m in my underwear, and YOU haven't taken anything off yet'. That's all the prodding I needed - my tie was quickly discarded, my shirt was unbuttoned and removed, and I was unbuckling my belt and pulling off my trousers in less than 60 seconds. Karen discreetly kept alternating glances between me and the monitor, and then I was seated next to her again - both of us in our underwear, with our legs touching.Mr. California had begun pleasuring himself, and Karen told me that watching a man masturbate was a tremendous turn-on for her.
On the monitor the guy took a break and typed in a message: 'You should both get naked now with me!!!' Karen and I were so completely aroused at this point that we didn't need any more encouragement. I was the first to move. I stood up, and my erection in my Jockey briefs was really straining at the material, and it was no more than 12' from Karenā??s face. I walked around behind her and said 'Do you want me to help you with this?' and I reached over and began unclasping her bra. She let out and audible sigh, leaned forward and shucked her bra off her shoulders. Sitting back I noticed how incredibly beautiful (and big) her breasts were; her pink areolas were at least the size of a dollar coin, and her nipples were very erect. Her left hand instinctively moved to her breasts and she began to fondle her nipples. As she did, I deftly slipped off my underwear and sat down beside her. Her eyes locked on my cock, which would probably be considered 'normal' - about 6', somewhat thick - not huge by any means. I was so aroused that the head was slick with pre-cum. I slowly began to masturbate and looked at Karen and said, 'So, what do you think' and I laughed. She said, 'Mike, I love it!!! I canā??t believe Iā??m seeing a naked man after all these years - finally!!!' With that she lifted her hips slightly off her chair and removed her panties. Her pussy was covered with a thick mat of brown pubic hair, and it was very apparent she was wet. Her inhibitions were gone as she pushed the chair back from the desk and spread her legs, moving her right hand down to her pussy and began to feverishly rub up and down her slit. Her groaning became pronounced, and I momentarily glanced at the screen just as our friend was beginning to climax. I quickly said, 'Karen - LOOK!' and pointed at the monitor. This young man shot rope after rope of come all over his chest and belly, and Karen was in her glory. As he began to clean himself up, we turned back to each other. I was in front and slightly to the side of Karen, with our left knees touching. I could clearly see her pussy, and she was obviously working her clit. As she did so I took the bold step of standing up and walking right up to her, my cock just inches now from her face and breasts. I was actually standing between her legs. I reached down and gently pushed her hand aside and replaced it with mine, and I quickly found her pleasure button, and alternately flicked, rubbed and pinched it was she moaned. As her hands were free, she reached up and grabbed my cock and began jerking it furiously, and rubbing it against her breasts.
Moments later she shuddered, groaned and thrashed as she had a very powerful orgasm. As she floated down, she inched forward and began to masturbate me in earnest, and as I was closed to coming she took me in her mouth. It was unbelievable wet and warm (something I hadn't felt in many years...) and she took me all the way in. As she fellated me, I reach down and played with her breasts, tweaking her nipples and rubbing them as they grew hard once again.On the verge of coming, I had her stop. 'Why donā??t you stand up, Karen?' She immediately stood up and I moved behind her. Her butt was large, very white and very round and completely sexy to me. I moved forward and began sliding my cock up and down her ass crack. As I did, I reached around and began to finger her again with my right hand, while my left hand played with her tits. In no time she was bucking again, pressing her ass back against me, increasing my pleasure. Her legs clamped around my hand and she was coming yet again! It was all I could take, and my cock was engulfed in the folds of her ass cheeks, sliding up and down, moistened by the pre-cum spilling from my cock. I then gently pushed her forward, her hands on the desk, and began to erupt streams of come all over her back and ass. I hadnā??t come that much since I was a teenager. Some pooled on the small of her back, while the rest dripped down her ass cheeks and crack. As we composed ourselves, and chatted about what we had just done, she suggested we shower.
Since we both had the night to ourselves, we retired to the bathroom for Round 2 - thatā??s another story for another time.