It was almost 8 years ago that I moved to this town with my daughter, Lisa. Her mother had passed away the year before, and it just hurt too much to stay in the same house. I was worried about taking Lisa away from where she grew up, but it turned out she wanted to get away as much as I did. Fortunately for us, she made new friends right away.
The first friend she made would also prove to be her longest. Anna and her parents had lived only next door, and while Anna was older than Lisa, they were both in the same grade. Anna was always so sweet and polite, and she was whip-smart too. Since I was a single dad, it was nice to know that Lisa wasn't alone after school while I was working.
Things started to change when the two innocent friends began high school. Both Anna and Lisa blossomed into beautiful young women, but while Lisa stayed somewhat shy, Anna had become as fiery as her hair. As she got older, she became drop-dead gorgeous - a face that could launch more ships than Helen's, long legs that she loved to cap with sexy shoes, an amazing ass that she learned how to tease just enough of to stay "innocent," and a full pair of natural tits that would be more than a handful for anyone. Of course she got plenty of attention from guys, and some from other girls too, but she never seemed really interested. I think that's part of why guys flocked to her - for all her obvious sexuality, she never seemed to date anyone, and everyone knows the forbidden fruit always tastes the sweetest.
Of course, as it turned out, that was part of the problem for me. After my wife died I never regained interest in dating. I threw myself into my work, and when I wasn't working I dedicated myself to being the best single dad I could be. It was the summer after their sophomore year in high school when I first actually saw Anna as a woman. Lisa had talked me into letting her host a pool party, and I had agreed on the condition that it had to be when I could be a chaperon.
I'm relaxing on a pool chair in my swimming trunks, watching the kids playing in the pool, when I realize my headcount is off by one. I had only a few moments to try and figure out who was missing when a dark shape surged out of the water in front of me, and Anna lifted herself out of the pool. As she stood there in front of me, water dripping off of her body, she threw her head back, tossing her hair behind her and thrusting her chest towards me, and my jaw dropped. For the first time, I saw - really saw - my daughter's best friend as the young woman she was. My eyes drifted slowly up her perfect legs, past her hands that were resting on her hips, and finally up to her face, where I saw her looking straight at me. Anna giggled, bit her lower lip, and sashayed towards me, swaying her hips in a manner that only a few moments before I would not have thought of as seductive. This beautiful, newly sexual creature came up and squatted down beside me.
"I wanted to thank you, Mr. Matt, for letting us have this party. I know you wanted to make sure you could be here to keep an eye on us, and I...wanted to let you know how much I appreciated that." She giggled again, then leaned in and kissed me on the cheek. She lingered there, with her lips on my cheek, my breath caught in my throat, before she ran her hand lightly up my belly and chest and pushed off of me with another sexy giggle, before taking a few steps back to the pool and diving in again. I started breathing again, and my voice almost cracked when I asked if anyone else wanted something to drink as I headed inside to cool off. I stood in the kitchen, the refrigerator door open, hoping the cold air would help my raging erection die off so I could go back outside.
It was months before the next event would happen. I usually wouldn't get much alone time until after Lisa went to bed, so often I would stay awake later so I could get some reading done, maybe watch some TV or play a game alone. I was turning out the light one night, getting ready to turn in, when I noticed a flickering light from the house next door. It was real late, so, curious, I took a peek. I could see the light was coming from downstairs, but I couldn't see what it was from my room, so I went downstairs and out to the backyard. We only had a short fence between us and our neighbors, so when I went outside I was able to see clear through their glass back door into their living room.
At first glimpse, I could tell there was someone on the couch watching TV. As my eyes adjusted better, I realized several things in very quick succession. First, it was Anna downstairs. Second, she was watching softcore porn on Skinemax or something. Third, her hand was buried in her pajama bottoms, and it was moving. I felt myself blush when I realized what she was doing, but I found myself drawn closer to the fence. I knelt down, and watched, entranced. When the screen would flash brighter, I could see her beautiful face, contorted with pleasure. As I watched, I could see her hand clutching at and pinching her nipples through her thin t-shirt, and her hand in her bottoms was moving a bit faster. I realized I was rubbing my cock through my boxers as I watched her, and I pulled my hand away.
I briefly struggled with whether or not to go, and just before I got up to walk away, I looked back at Anna. What I saw practically knocked me on my ass - she had pulled her pajama bottoms down, and I could see her long fingers diving in and out of a pussy that made my mouth water just to look at. I watched her fingers trace the outline of her lips, rubbing up and down them slowly. Then, she'd curl her fingers, and slide them inside. I watched, breath catching in my mouth, as I could see her throw her head back, clearly moaning in pleasure. My brain had compartmentalized - a part of me was screaming that she was 17, she was my daughter's friend, that this was wrong, but yet my hand had taken my cock out of my boxers. I was so excited by this vision in front of me that my head was glistening with my precum, and when I wrapped my fist around my cock it slid easily up and down with the lubrication.
I watched Anna's hands work at her body faster - her left hand was under her t-shirt playing with her breasts, while her right continued to fuck herself harder and harder. My fist pumped faster and faster up and down my cock as I spied on my underage daughter's best friend, squeezing the head every time I pulled my hand up. I stopped for a moment and rubbed my index finger around in circles just below the head of my cock, and closed my eyes.
When I opened them, I saw Anna's hands moving like lightning, her body writhing around on the couch. My hand started flying on my cock, eager to stroke myself to orgasm. I panted out loud, breathing hard, and reversed my grip on my cock, with my index finger and thumb around the base and my palm gliding over the slick mushroom tip. Finally, Anna came. She convulsed hard, bending over in half, and then collapsed on the couch. Outside, I could just barely hear her wordless scream of pleasure, and when I did, I met it with one of my own. My seed shot out of my cock like a fire hose, and I painted the fence with it, spurt after spurt. After I caught my breath, and looked up, I saw Anna looking out the door, licking her fingers one by one. I froze, fearing I had been caught, but once Anna cleaned her fingers she turned off the TV, and went upstairs. As soon as she left, I scurried back inside to clean up, forgetting about the load I left on the fence - there's still a stain there today.
I'm still not sure if Anna saw me that night, but if she did, she never said anything. More importantly to our story, she didn't stop masturbating around her house. Over the next year or so, leading up to their graduation, I must have seen her masturbating at night dozens of times. Sometimes it was downstairs, sometimes in her bedroom. Once or twice, she even did it outside. Anna became my favorite masturbation aid. I would hold off on jerking my cock for weeks just so I could explode while watching her, and it got so bad that seeing the TV on in a dark room would cause me to get horny. I probably stroked out pints of my cum to the girl next door, to my daughter's best friend pleasuring herself. I always took great care to make sure I couldn't be spotted, but I always wondered if she had seen me that first night. Had she always masturbated like this, and I just hadn't noticed before? Did she see me that first night, and that's why she's doing this? I tried to push those thoughts away - she was 17, she was my daughter's best friend, she was my neighbor's daughter, there were so many reasons I should not be thinking of her like that, but yet every time I saw the soft flicker of a screen from a room in her house late at night, I always grabbed the lube.
Somehow, I managed to make it through to their graduation without being discovered. Anna had gotten a summer job at Victoria's Secret, so Lisa had been spending a lot of time at the mall. Lisa said she had found some really cute clothes there, and wanted to know if she could get them. I told her I'd need to go with her to see what she wanted to buy first. Little did I know what was going to happen to me that day...
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