Though I listed this as fiction, some of it is based on real experiences
I know I should have just turned around and walked away. The guilt took in an instant as I realized what I was doing. After all it’s probably not a normal thing for a man to stand in the shadows watching his only daughter masturbate. As quickly as the guilt took hold my mind started racing to rationalize my presence there. She shouldn’t be doing that, especially not there on the couch. I had gone upstairs to go to bed well over an hour ago so I’m sure she thought I had long since fallen asleep. But She should have realized that if I were awake and I happened to make my way downstairs again I would see her on the couch long before she saw me or heard any clue that I was coming down.
Maybe she assumed I would turn the light on before I rounded the corner into the alcove that overlooked the living room. Had I done that to navigate my way downstairs she would have had plenty of time to cover up before coming into my view. She had to recognize that I’ve been living in this house since shortly after her mother and I split up nearly 10 years ago. Didn’t she? I haven’t needed that light for years.
However it happened, here I was standing several feet above her in total darkness my form further veiled by the solid safety banister that kept one from falling off the edge of the upstairs hallway into the living room down below. I now know it’s not my fault that I caught her here and for a moment the guilt started to slide away.
It wasn’t the first time I had caught her masturbating. It was however the first time I started to watch. The last time wasn’t my fault either, at least not completely.
The last time was just a few weeks past her 17th birthday. Ninety percent of the time I have the house all to myself so I typically just walk into any room I need to without thinking much about it. When she is with me for the weekend I try hard to respect her privacy and almost always knock on any closed doors before walking in. For this particular instance it wasn’t more than fifteen minutes since I had seen her out by the pool with her friend. I know this for certain because I was trying to avoid what I perceived as one of the several other real benefits of having a pool.
When her mother and I split up I made sure to get a house with a pool for three reasons. 1) I could afford it, 2) Beth, my daughter, had always wanted one and 3) Kelly, my ex-wife, never wanted one. I figured as long as I had a pool my daughter could always find a reason to come and visit me. The decision to get a house with a pool had an unknown added bonus as well. Aside from the fact that I was right about her spending a lot of time here there was the added benefit of her often bringing friends over.
It wasn’t much of a benefit at first. After all her three friends that spent the most time there were aged anywhere from 7-9 years old and though I know some people get excited by that I don’t. Not even close. So it was in fact a bit annoying in the early days having to play life guard to her and her friends.
The first bonus benefit came in the third summer. About a month into the summer I ran into Emily while buying gas at local quick mart. She was headed for the car in the lane next to mine and It took me a few moments to realize it was her when she walked out the door. She caught my eye as soon as the doors opened and I immediately noticed the beautiful rack her tank top barely contained. My eyes next roamed down to her tiny waist that looked way too small to support the heft of her chest.
It wasn’t until she was about half way to me that I took a good enough look at her face to realize who she was. She was the daughter of one of my wife’s friends who several years ago began babysitting Beth whenever Kelly and I went out. I quickly did the math and realized that she must be around 20 years old by now. She had always been an attractive girl. Even at sixteen when she started babysitting for us she just had that look about her that let everyone know she could get just about any guy she wanted to do anything for her. I remember I used to worry a bit about her watching over Beth because I was afraid she’d have boys over at the house while we were away. But she was a responsible kid and to my knowledge had always respected the fact that we were paying her to watch our daughter and she held true to doing just that.
She was always wearing something that was just a bit too revealing or a size or two too small. If you asked me then or even a couple of years ago if part of the reason I liked her babysitting was because she was so good to look at I would have denied it. After all she was only 16, I was happily married (or so I was still telling myself at the time) and I was more 10 years older than her. But I’ve done a lot of things I probably shouldn’t have in the past few years and am not nearly the prude I was back then so I’ll admit it. I really liked it. A lot!
I used to purposely keep my wife out extra late in hopes that it would be too late or she would be too tired to drive back home. I would tell her before she came over that it might be late before we got back and she was welcome to stay the night in the guest room if she didn’t feel like going home. Then nearly every night when my wife and I got home we would find her lying on the couch with the TV on. Sometimes awake other times asleep but she always had something on that caught my eye. Most of the time it was an oversized button down pajama shirt and a pair of tight shorts. On the really good nights it was a longer pajama shirt or a t-shirt that just barely covered her thighs and not much else.
But now here she was a few years later. Twenty years old about 5 foot 4 inches tall with breasts that would stretch a C-cup and I could suddenly feel them pressed against me when she recognized me and came to give me a hug.
We chatted for a few minutes about how good it was to see each other again, how much she missed babysitting for us, how much she missed Beth and how happy she was to be home from college for the summer. Apparently she had talked to Beth because her eyes really lit up when she told me she thought it was cool that I had a pool now. Without even thinking about it I let her know that she was welcome to come by and use it when she felt like it. I was usually at work during the weekdays anyways and she had already told me that she usually had to be at work by 3:00 or 4:00 every day so it was really no skin off my back.
Sure enough the next several days I came home and it was obvious that someone had been at the pool. I thought about leaving the backdoor unlocked with a note to her to help herself to any snacks or soft drinks I might have in the fridge but realized she probably didn’t come over alone and though I trusted her I didn’t want strangers walking around in my house while I was away. She didn’t come every day but when she did for some odd reason it always got me a little excited to know that she was here. I found myself wondering what her bathing suit looked like and even once considered setting my web cam to look out over the pool from my window so I could see but that thought seemed creepy even to me.
She must have been doing the typical college partying on weekends because she never even showed up then. I tried to come home early a few times to see if I could catch her there but to no avail. She had either not come that day or had already left by the time I got there.
The first time I even saw her in my back yard was about three weeks later. I had a guest over at the time. A woman I had been sort of dating for a while. I say “sort of dating” because we pretty much just went out to dinner or drinks and ended up at her place or mine for a couple of hours of sex. Sure we got along well and the sex was good but neither of us had any notion that our relationship, for several reasons, would ever progress to more than what it was.
This particular night was an especially hot night so my date and I decided to sit out by the pool for a while before heading inside. We both lay back in the double lounge chair and within a few minutes were already getting started on what we knew would eventually happen. Not long after we lay down my date was straddled in front of me, both of us naked above the waste, and both with unbuttoned pants. I had just released her nipple from my mouth. My hands were in her pants caressing her ass as she began working her lips down my neck. She was kissing my chest and had just wrapped her slender hand around my erection when I heard a car door slam. Here I was about to get a blow job from a woman who had up to that point given me some of the best head I’ve ever had so the sound of the car door barely registered to me but my date thought now would probably be a good time for us to head inside. I pushed her up to her knees, and took one of her nipples into my mouth one last time as I reached a hand farther into her panties. As I slowly pulled my hand out, I made sure to let a finger slip gently between her wet lips and ever so slightly into her hole before withdrawing it the rest of the way between the crack of her ass.
With that, we both stood up, I grabbed the clothes we had already shed, she grabbed my cock and started to lead me inside by her make shift leash. While we walked I pulled myself slightly behind and to her left so she could keep hold of my cock while I wrapped my hand around to fondle her breasts. She squeezed a little tighter as she turned her head so our lips could meet. And that’s how we walked back to the house. That was, that is, until we got to the patio. I’m not sure which of us saw her first but as we broke our kiss to walk up the patio steps we both froze as we saw Emily standing there in her waitress uniform.
Emily must have been freaked out a little bit too because she just stood there like a dear in the headlights. Her eyes moved as if trying to figure out what she was seeing. First she met the gaze of my date then my date’s breasts and onto my date’s hand which was still wrapped around my erection where her eyes lingered for a moment before looking me in the eyes. Emily looked once more at my date and quickly turned away and apologized.
When I finally got my bearings I quickly separated enough garments for me to hold something over my midsection and for my date to cover her breasts. Emily was still apologizing when she turned her beat red face ever so slightly to see if we had covered ourselves. When she looked down and saw that we were more or less covered she turned a bit more toward us but it was obvious she was avoiding either of our eyes.
I didn’t know what else to say so I introduced Emily as a friend of the family and my date as a friend of mine. Emily who looked like she couldn’t decide whether to make a break for it or just jump in the pool and remain under water until everyone was gone apologized again and told us she wasn’t sure if I would be home but since it was so hot out she thought she’d sneak in for a quick post-work dip in the pool. My date said in a tone that I thought was a bit too cold for the situation that we were obviously heading inside for the night. My date then surprised me a bit when she said “But we’re done with the pool now, have fun”.
For a brief moment I thought or maybe just hoped that Emily would actually take her up on the offer but she just apologized and said that it was already getting pretty late and she should get home. She apologized again, looked down at my midsection as if to make sure I did the right thing and covered myself, said “I’ll talk to you later” and was gone almost as quickly as she showed up.
I don’t know why I felt enough to guilt to try to explain the situation away to my date. But I did. And she must have sensed my guilt because as we were walking into the house and up the stairs she began to grill me about it. Every time I thought I produced a rational response she would just look at me, smile and say “uh huh” or “sure”. I wasn’t sure what was going on. On one hand she seemed a bit mad that some attractive woman just suddenly showed up behind my house but we were still on course for the bedroom so I eventually realized I should just shut up before I say something stupid.
By the time we got to the bedroom I had already decided that I should do my best keep her interested so as soon as we cleared through the door I turned her around toward me, cupped both ass cheeks in my hands and pulled her close for a deep kiss. After a brief squeeze I started pushing her back toward the bed while I kept my hands in her pants and slowly started to move them around to her hips. By the time we made our way to the bed her pants were down off her midsection as I began to slide them down her thighs. I gently guided her to first sit then lie on the bed. After she was situated I propped myself up with one hand on each side of her and started making my journey down.
As slowly as I could manage I made my way to her neck then let myself drop a bit to my elbows so I could squeeze her breasts together as I sucked in her nipple. First the left one then my tongue moved lightly across her left breast on to the right breast where I found her other nipple, let my tongue roll around it a few times then greedily pulled it into my mouth making sure to give her left nipple a bit of a squeeze at the same time.
The moan that escaped her lips got my heart pumping so much that I wanted to just rip the rest of her clothes off and bury myself inside her. With a self reminder that now was the time for me to be focusing on her desires and not mine, I forced myself to resume my original journey. Shortly after a brief layover at her belly button I found my tongue just above her bushy but well trimmed pubic mound. I was so focused on the journey that I had forgotten to finish removing the rest of her clothes so I stood up , pulled the rest of my clothes off and found a bit of delight when I saw her look first to my flat stomach, then to my rigid cock and back up to my eyes as a smile began to form on her face.
One of the things I liked most about her was she was one of the few women I’d been with who seemed to like to touch herself as much as she liked to be touched. She wasn’t among the better looking women I had found myself with over the years but when she brought both hands up to start pulling away at her nipples with her legs dangled over the edge of the bed at the knees and her legs spread open just enough for me to catch a glimpse of her heavenly maw she was surely amongst the sexiest.
When her hand started to move down that space between her legs I knew it was time for me to get back to work. I reached down pulled both her legs up to rest on my chest and removed what was left of her clothes. Her eyes closed as her hand reached between her legs and a finger started moving up and down over her moist slit. At that moment I felt an undeniable urge to taste her so I quickly kissed licked my way across her ankles her knees and then finally to her thighs. The room felt about 5 degrees hotter as she pulled her finger away from herself, placed her hand on my head, spread her legs wider and allowed a leg to rest on each of my shoulders. I could feel her wetness on my cheek as I began to work both thighs.
By the time my kisses and licks reached her gentle folds her hips had already started moving. The more she tried to center on my face the more I had to resist the urge plunge my tongue in. My tongue pushed up higher between her legs and made one long sweeping pass against the entire length of her slit, all the way down until I felt my nose bury into her pubic hairs. Then slowly back up as I let my tongue snake just a little deeper inside. As I made my way back up to the top I could hear her breath quicken and her hips begin to move with more urgency. Finally my tongue was back to the top where I let my tongue dance just outside the barrier to her clitoris. As I looked up at her, I could feel her hand digging harder into the back of my head while she pinched a nipple with the other. I could almost smell her hunger as I teased her by licking up and down on the shaft of her clit while painstakingly trying not to actually make contact with her now swollen button. And then it was time; time for her to get what her writhing hips had been pushing for. Another long moan escaped her lips as I let my tongue dance across her clit. I moved it everywhere, slowly, up, down, side to side, more quickly all the way around trying hard to avoid any type of pattern.
When I felt her hips press harder against my face I pulled my tongue back into my mouth and gently sucked her clit in to follow. Her hand moved off the back of my head and up to join her other hand to knead her breasts. As soon as I noticed her pinching her nipples a bit harder I sucked her clit in so hard that for a moment I thought her sharp inhale was from pain. When I looked up to her face and saw that she looked completely lost to the world I knew it was not so I brought my fingers up to explore her depths. First one, then two as I gradually started building speed. Her hips were bucking so hard now that it was becoming difficult for me to maintain contact.
I could tell by her squeal she was getting close now so I endeavored to hold on for as long as I could as my fingers once again quickened their pace. Then, all at once, it was there. Her body froze her breath fell silent time seemed to stand still for a moment and she exploded.
I wanted to give her a moment to recover before moving on to my needs so I spent a bit more time nuzzled between her thighs, careful not to make too much contact with her now sensitive clit. I’ve tasted enough women to know two things. One; they didn’t all taste the same and two; I wasn’t particularly fond of the taste. Don’t get me wrong, I greatly enjoy pleasuring a woman like that and the harder she cums or the more she flows the more exited I get. It’s just not a taste that I have ever really enjoyed. Because of this I had a difficult time staying down there as long as I should have and had to start working my way back up.
By the time I made my way back up to begin kissing her mouth her hands were already gently scratching up and down my back. Even though her legs were still over the side of the bed and I was barely laying on the bed she wrapped both her legs around me and started pulling me close. As soon as my cock pressed up against her folds I instinctively knew that if I pushed it in now I wouldn’t be able to last two minutes. Not only that I was feeling a bit selfish knowing how hard I had just made her cum with my mouth and was really hoping for her to return the favor.
One way I could always seem to get her to give me a blow job was to wrap her breasts around my cock. She didn’t have particularly big breasts but they were big enough to bring at least some sensation to me as I moved back and forth between them. Though it felt good it also had the added benefit of looking real hot which got me even hotter. She must have liked the way it looked too because it was rarely very long until she was kissing my tip and moving on to bring me all the way into her mouth. Just as I was about to move up so I could straddle her and place my member between her breasts she surprised me a bit by pushing me up and off the bed.
When I finally managed to stand up she slid off the bed far enough so that she was now squatting in front of me while she supported part of her weight with one elbow on the bed. Her other hand reached around my butt and guided me into her mouth.
She didn’t even have me all the way in before I knew I wouldn’t be able to last long. One thing that made her blow jobs so good was her ability to take me all the way into her mouth until I could feel myself sliding down her throat. Granted, I’m not exactly huge but she was only the second woman I had been with that could take all 7 ½ inches of me in like that without gagging or quickly pulling away. Just the site of me buried all the way into her mouth was often enough to bring me to the brink.
Tonight was no different. I didn’t want to cum yet so I pulled myself out and was about to pull her back up onto the bed to rub myself against her breasts some more when she dropped to both knees and grabbed me by the hips to keep me from pulling further away. She obviously has been with me enough to know exactly why I do things when I do them because she immediately asked me with that mischievous grin on her face why I was ready to cum already. When I told her that she was just getting me hotter than usual she got a curious look in her eye and asked. “Are you sure that’s the only reason?” I honestly wasn’t sure what she meant so when I replied “what else would it be?” I didn’t intend for it to be anything more than a question. She somehow took it a whole different direction and flat out asked “Are you sure it wasn’t because the baby sitter looked so long at this?” She then pulled on my dick and gave it a squeeze for emphasis.
For a moment I thought I should deny it. I wasn’t after all sure that was the real reason, though the way she just said that certainly brought an extra level of excitement. When I realized I was twitching in her hand I knew there would be no way of denying it so I told her that as guilty as I felt for it being true there was in fact some truth to what she said. To my surprise she just smiled at me, told me that if she was into other women then Emily would definitely excite her too. She then sucked me in deep again and began working me for the few short minutes it took me to be ready for release. When I told her I was ready to cum she pulled me out of her mouth and shocked me again by saying “would you like to shoot it on Emily instead”?
I knew better than to answer that verbally but the moan I let out and the solid stream of cum I shot across her chest left no doubt what was on my mind. I knew there was no way Emily and I could ever get to that point but just the image I had in my head of Emily of her on her knees waiting for me to spray all over those young voluptuous breasts was enough for me to have one of the hardest orgasms of my life.
We fucked twice more that night. Although neither of us mentioned Emily again I think we both knew what was turning the heat to a higher level for me. I wanted so badly to hear her talk more about Emily and when I was in the kind of mood I was in I really wanted to just hear anything naughty or sluttly come out of her mouth but the one time I told her that I’d always wanted to try sex like that she made it clear she wouldn’t be the first one to do it. It didn’t matter much that night though, as much as I’ve always wanted to be with someone willing to be a bit of a slut the images of Emily that kept popping into my head was more than enough to help me moan a bit louder or fuck a bit harder.