I will refer to her only as C. I was in my teens, and inexperienced having grown up in a very strict Christian family.
From a young age, I was good with computers, and a bit of an entrepreneur at heart. It didn't help me in any high school popularity contest, but it did have other benefits. Through a friend that knew our family, I was introduced to C. She was in her mid forties, and after getting laid off from a job that had spanned most of her career, she opted to start her own business - an internet service provider. Not knowing much about computer technologies, she had hired a young alpa-geek - older than me, but still young (early 20's maybe). Like many techies, he turned out to be unreliable and one day C called me desperately needing help with a non-responsive server.
Over a few months, I assisted C on a fairly regular basis. She lived in the next subdivision over, and operated her business from her home. I would come over late in the evening once or twice each week to tweak and maintain her servers (it had to be done late at night because you couldn't take away people's internet access during the day to do this kind of maintenance).
Eventually, we connected on instant messenger, so she could ask me questions when I wasn't there. As time went on, we would chat more and more about personal things - our lives, families, etc. She had 3 children, 2 of which were grown and had moved out. Her youngest daughter, then about 16 still lived at home. She was long divorced. Gradually the conversation dipped into more...interesting...topics, as tangents, but briefly and then they would return to more benign topics. For example, a witty sexual innuendo in response to something might lead to a "have you ever done that?" sort of question, which might prompt a few follow up questions or comments, but then return quickly to whatever topic had been at hand.
Through these IM conversations, I didn't really get the sense she might fancy me, but being young and incredibly chronically horny, those brief conversations still turned me on. At least half the time, I probably was the one taking the conversation to the tangent. Often after an exchange like that, I would masturbate while carrying on the continuing conversation. At one point, I recall making a remark about the conversation turning me on, and asked if they did her too...she only responded with a wink emoticon, and then continued on the non-sexual prior topic. Occasionally she would remark that I was "the kind of guy she would want for her daughter", and I wasn't sure if that was mean to put me off.
Sometimes these server problems would get complex, and from time to time I would end up working non-stop for several hours - sometimes till the wee hours of the morning. I recall at least a few times going over to her house in the evening to work on her systems. As I got exasperated with an issue, she would bring me drinks (she kept her fridge stocked with Pepsi for me), and generally be supportive. Noticing that my neck often bothered me, she would sometimes stand behind me and rub my shoulders and neck (which I'm still a sucker for). I remember at least a few times being turned on by that touch, and ending up stuck in the chair for a while waiting for my throbbing cock to calm. Occasionally she would lean down to see something on the screen in front of me while she was doing this, and I would feel her breath on my ear and neck, and that always sent me into rock hard horny land.
Her remaining daughter at home, K, got used to seeing me around - and became accustomed to me staying late at night. When I would end up there until the wee hours of the morning, I would sleep in the second bed in her room, which her older sister had vacated when she moved out. I was always attracted to K who was closer to my age anyway. Multiple times, I would tiptoe in late at night after having C breathing in my ear and still horny. I would strip down to my underwear, get into "my" bed and admire K asleep in the bed "next door" in her nightie and rub my cock, cumming in my underwear as quietly as I could. But that's another interesting story for another time.
Eventually C requested my help with another problem. She needed her lawn mowed after her son had moved away from the area. Each Saturday, I would dutifully come over in the mid-morning. I had a key to the house, and I would let myself in, get a drink put together and proceed outside to get the mower and get started.
One Saturday I decided to start with the front yard, and began to drag the mower around the side gate to the front. C's room window was at the side of the house, with a sliding glass door at the back. As I dragged the mower past her window, I happened to glance in through her open blinds and...I couldn't be sure with the glare of light off the glass, but I could swear she was laying in her bed...naked, I thought. I tried not to look in obviously, in that brief few seconds, keeping my head averted as if focused entirely on the mower, but glancing up trying to see. I got the mower out to the front, but I wasn't sure. She was definitely topless, I saw her breasts clearly. She was a heavier-set woman and her breasts were very large. I pretended to need something - gas can, trimmer, whatever, and went back by the window again. On my way back through the gate, with the angle I couldn't see anything without craning my head, so I passed inconspicuously. I got what I "needed" from the shed and headed back out past her window again, this time getting a view (though still hampered by the glare on the glass)...breasts definitely exposed...and I thought I saw a patch of pubic hair! My cock was swelling in pants, and my hands trembled with the adrenalin rush. Back in the front yard I fiddled with the mower, mind racing. She was naked on her bed, lying on her back. I wanted to see more.
Again a few more times, I discovered I "needed" more things, and passed back by the window, each time a little slower, thirstily drinking in every visual detail I could see. She was asleep I thought. She hadn't moved. Her head was turned slightly sideways away, and while I couldn't see her eyes clearly, I thought they were closed. I would go back. I would get a better view. I walked quietly back to her window, but standing to the side just in case she was awake. I carefully leaned slightly to get one eye viewing close to the window where the glare would be lessened. She was stark naked. Asleep on her back. My heart raced. I carefully repositioned to look through clearly with both eyes and touched my hard cock through my jeans. So sensitive, it jumped when I touched it. For a minute I watched her before unzipping my pants. I'd better be careful - I had no idea where K was. Just as I eased my cock free of my jeans, suddenly C began to stir on the bed. I ducked nervously, trying to shove my cock back into my pants. After a few moments, I got my nerve back and eased my head back up, ever so carefully. She had shifted, but it looked like she was still asleep. Her shift was one leg (both of which had previously been straight on the bed) - as if she'd bent one knee, keeping her foot flat on the bed, and then fallen back to sleep, allowing the knee to fall sideways - and giving me an uninhibited view of her crotch. But she'd also moved her head and now if she opened her eyes, she'd be looking right at me. Risky. Very risky. But her pussy was exposed. I had to. I brought my cock back out and pumped it hard, my abdomen convulsing as I exploded, squirting all over the siding of the house - all the while never taking my eyes off her. I pumped out the remaining drops of cum, and uncomfortably stuffed my cock back in my jeans. Ducking to head back to the mower, I suddenly realized...her bedroom door was wide open.
For a few more minutes, I fiddled with the mower while my mind spun. Should I not start the mower yet? That would definitely wake her, I thought. I could go inside to get a drink...the bathroom was at the end of that hall where her bedroom door was...I could just innocently be going to the bathroom and pass her door...and there would be no window between us. That seemed the thing to do. What would I do then? I didn't know...I didn't even think about that...it just seemed even more erotic to be in the same room with her naked. I headed back to the back yard to go in through the kitchen sliding door - that wouldn't make any noise. As I passed by her window I strained to see. Abort mission! She was up. Still naked, door still open, back to the window. I turned and headed back toward the mower. The game was over, might as well mow.
I mowed the front yard, and then dragged the mower back through the gate. Again, I couldn't resist having a glance. Of course it would be pointless now, because now awake, surely she was dressed. My quick glance told me otherwise. I couldn't stop to see, but she was still naked, digging in her closet, and the door was still open. I wandered around aimlessly in the back yard for five minutes or so looking for rocks in the yard to toss out, while my mind spun a million miles per hour. I wanted her to know that I saw her naked. I wanted to see her reaction. But I didn't want t get in trouble - she couldn't think I was a creep. It couldn't be through her window. But I could innocently be headed to the bathroom. Nothing would be wrong with that. I went for it.
Into the sliding glass door, quietly through the kitchen - I stepped carefully so my shoes wouldn't squeek on the vinyl floor. On to the living room carpet, now I could see straight down the hall. I could see the edge of her bed. And I could hear some weird noise from her room. I walked quietly past K's room - the door was open (which meant she wasn't in it - she must be gone). I continued down the hall, and it sounded like...really deep breathing...and some low hum. I got to the bathroom door - I could now see her foot hanging off the bed, and part of her leg up off the bed. The back of her leg. I breathed quietly, and leaned forward again, just enough to see. C was up on her bed, on her knees, facing the window....naked, with her ass up - and an electric back massager jammed firmly against her pussy. I was shocked. And fucking hard. She was turned away, she couldn't see me. I was going to watch as long as I could get away with. I remember having a sigh of relief that I hadn't tried to look through the window again - since she was facing it. I watched as she rocked her hips slightly, moving the massager only slightly with each rocking motion - but always ground firmly into her clit so that her pussy actually distorted, and her pussy actually pushed open with every motion. She moaned, and bucked, tensing up occasionally, then relaxing again. Every 30 seconds or so she would rub the massager down the length of her slit and back to her clit, and I could see it get wetter each time. I wanted to get my cock out again, but I didn't dare - just in case she suddenly turned around. I stroked it through my pants, carefully so I didn't drench my underwear with cum. I watched in erotic ecstasy and awe for what was probably another 2-3 minutes but seemed like an eternity and a flash all at at once. She pleasured herself unrelentingly and rode the massager to a moaning orgasm. As she began to cum, she bucked her ass up higher in the air, squeezing the massager between her thighs, her shoulders dropped toward the bed - and her face turned toward me, upside down at an angle. Her eyes were closed, but I couldn't chance it. I quickly took a step backward toward the bathroom doorway. I swear in that moment her eyes opened and she looked at me (though later she would swear that while she knew I was outside and thought she'd seen me peeking in the blinds, she had no idea I was in her doorway watching her). I dodged quickly into the bathroom and shut the door loudly enough she would certainly hear. I freed my cock and it sprang to life like a coiled spring, bouncing and quivering. I came in a matter of seconds, squirting into the sink.
When I came back out of the bathroom, her bedroom door was mostly closed with maybe a 1" gap. I wanted so badly to peek back in there, but clearly she knew I was in the house now. I didn't dare. I got a Pepsi and finished mowing the lawn.
It was perhaps 2 weeks later that our tryst would start, though her exposure might have been considered foreplay, I suppose. During that 2 weeks, something had shifted it seemed. I wasn't sure - maybe I was just noticing more because now I was hyper sexually aware of her. I would be working late at night in her living room, and she would come out wearing a low cut t-shirt, and obvious lack of a bra. At least a few times I noted that she had come out into the living room in a different outfit - but I'd never heard her bedroom door close or open.
Late one night - very late - I was working on a server problem. As usual, C brought me Pepsi, snacks, and rubbed my shoulders while I worked. As usual by then, I was hyper sexually aware of her, and every breath on my neck, everytime her hands wandered down my back or sides, or lean forward and feel her unrestrained breasts on my shoulder - I was hard for easily over an hour, working with my cock fighting to tear my jeans apart and escape. C sat down next to my chair, on the floor, seeming to pay rapt attention to my work. I was sure she must be able to see my cock straining - it's not small or easily hidden. Precum had also wetted my underwear and was showing through my jeans and was making me uncomfortable. I tried to focus on work, but flashes of her cunt riding that massager kept going through my head, and I could see her nipples under her t-shirt. As time went on, I had to pee. And there was no way to get up without being obvious. Finally, she seemed to be paying attention to something else (maybe a magazine or something) and I excused myself, getting up carefully averting my front to hide the mess at my crotch. I walked awkwardly down the hallway, into the bathroom.
I let my cock loose again, standing in front of the toilet. I was going to have to relax - I needed to pee badly. I had to firmly hold it down toward the toilet - it was so hard it would only point up, and pointing it down actually hurt. It was probably a minute I stood there, and then my nerves jumped. The bathroom door had opened slightly behind me. I turned instinctively toward the door. C seemed flustered for a second. "Oh sorry - I didn't know you were in here!", but she stared at my cock and didn't back out. I knew she knew I was in there, I had excused myself to the bathroom. She opened the door wider and asked "Are you OK?". I nodded, speechless. Her face was sultry, her dirty blond hair around her face and huge breasts tightly in her tee. "Having a hard time peeing with that thing?" she asked softly. I think I remember grinning a little - clearly she knew it was hard to pee with a hard on. "I can imagine..." she went on, "...look at that thing..." She grinned coyly. "Here, I'll hold it for you." She stood behind me, reaching around, she held my cock gently. I took in a sharp breath and it twitched in her hand. She was taller than me, and I could feel her breasts firm in my back, as she stood right up against me. "Relax..." she said softly "...you'll feel much better after you pee..." But, I could not. For probably 2-3 minutes we stood that way with her softly attempting to call me with her words, but letting her hand move just enough to stimulate my cock. Precum dripped into the toilet making a seemingly loud noise. But no pee. There was no way I was going to be able to pee like this. She knew. Using my cock like a handle she turned me slightly, dropped to her knees and pushed my cock up high. She began sucking my balls, and licking them...and then licked up my shaft. More precum oozed as her mouth hungrily wrapped the head of my cock and she ate it like dessert. Very quickly, my cock stiffened and throbbed and my body went numb as I shot my load into her throat. She swallowed moaning and pumping me with her hand, clearly enjoying it. She sucked me dry. A drip escaped her lip and started running down her chin. She used my cock to stop it, and then licked it off, keeping eye contact the entire time. She held my cock in her hand, softly and talked to me while I calmed down and it went flacid. She then took her place behind me again, holding me while I peed.
That's how it all began...
