The Girl Next Door

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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Office Blackmail of a Cheerleader Has Been: Partners In Crime

“Our little intern has a nasty little secret,” Anna said quietly as she came into my office, almost falling off her sexy heels as she pivoted to shut my office door. Her eyes were dancing, sexy and powerful, and I felt my cock respond right away to the energy that my office fuck-buddy was bouncing around with.

“Slow down. What secret?” I knew Anna had it out for Lindsay, the cheerleader blonde that I had hired as my summer intern. More than had it out; Anna fucking despised her, for reasons that were far beyond my understanding. But I had to be careful here: fucking Anna regularly was hot but also dangerous given that she, technically, reported to my office (which means, technically, she reported to me). 

“Bottle of tequila, top right desk drawer,” Anna spit out, eyes flashing. “And you know the rules about booze in the office. You should fire her ass,” she said, almost  challenging me. My cock stirred again, wanting to feel Anna take out her energy in other ways. Like riding my now hard shaft til she exhausted both of us.

That is when the light went on.

“I have a much better idea for that ass than firing,” I smiled. “Tell Lindsay, I want to see her in my office right away.” Anna turned, almost running out the door. Talk about fucking hot asses, I thought to myself, watching her tight skirt hug the curves as she headed across the office.

“You know that having that bottle is grounds for termination, don’t you?” I asked Lindsay directly, as Anna sat in the chair next to her. Usually I hate disciplinary meetings, and this one, so far, had gone as usual. Denial (that is not mine, sir), anger, and now fear. Turns out my tight-assed former college cheer queen had lost more than one job due to her little drinking problem, so she saw this as maybe her last chance.

“We went over this clearly when I brought you onto this team, Lindsay,” I said sternly, standing up and moving around the edge of my desk. At 6’3” I literally towered over the red-head and blonde sitting in front of me. “Was I not perfectly clear on policy around drugs and alcohol in this office?”

She could only nod. She had almost given up now, I could feel it. My eyes locked with Anna’s, who was still a bit unsure of what was unfolding.

“I will tell you what, Lindsay,” I started, slowly. “Let’s take this as a warning, and get you in touch with someone that might be able to help a bit rather than simply reacting here.” I felt Anna’s anger rise even as I said this. Lindsay’s eyes met mine, and I could see relief pouring from them. She nodded silently. I could also see clearly that the cheerleader body was still there. No Anna in terms of sexy tits and lips, but not fucking bad, I had to admit.

“But, young lady, there is still the question of discipline,” I said softer now, watching for another type of flicker in her blue eyes. Nothing. I had to do this the hard way, I guess. “Here is the deal, Lindsay,” I was stern again. “I want you to do exactly as you are told right now, or your ass will be out that door by noon. You need this job way more than I need you around here, so are we clear?”

All she could do now was nod. Anna got up, locking my office door.

Lindsay was almost gagging on my hard cock. Cheerleader hot, to be sure, but not so experienced in the deep throating department, obviously. But blackmail was blackmail,  and I was demanding payment in full if this little blonde bimbo wanted to keep her lame job for another few months. 

Anna had her cheap skirt almost down to her ankles now, her panties following. Eyes flashing as she watched her nemesis being force fed my cock, Anna not-so-gently started to finger-fuck Lindsay from behind, making the cheerleader almost leap with surprise. Anna almost kicked her legs wider as she slipped two, then three fingers into the now wet pussy. Months of frustration throbbed in those manicured fingertips, I could almost feel it. Anna’s red-hair was alive with energy as she plunged her fingers deeper, rougher with each thrust.

On my cock, Lindsay moaned, wanting to fight what was building but unable to. I began to fuck her mouth in rhythm with Anna’s fingering. I locked eyes with my red-headed partner in crime, and we both smiled. Anna knew that once I was done with this appetizer, it was her that I wanted for my main course. Bonnie and fucking Clyde must have had the hottest fucking sex in the world, I thought.

I felt Lindsay quiver as Anna brought her to the edge of probably the first orgasm this prom queen had ever had in her fucking life. I began to jackhammer as Anna pushed hard and deep for the finish. I noticed that Anna’s nipples were hard now. She might hate Lindsay, but was definitely turned on by making her cum.  My cock began to load up now, so I pulled out suddenly. Lindsay gasped for air quickly, but then moaned (almost too loud for this fucking office) as she came hard for Anna. In seconds, she came hard and got a full (and her first) facial. My cum dripped from her face, as she gasped again and again. 

“Anna rules this office, you little bitch,” I found myself saying, as Lindsay collapsed to the carpeted floor, whimpering with a mixture of shock and pleasure. “And if you want to keep pulling a paycheque, you will never, ever forget it.”

Leaning over the quivering body, I gave Anna a deep kiss.

~D.

Anna

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Teasing & Titty Fucking My Best Friends Dad

As I have often told MBA students during my college visits, some of the necessities of being a successful and well-compensated CEO is a passion for hard work, long hours, and a love of making money. What I do not tell them is that one of the benefits is the freedom to work from my summer home as much as I can during the warm months of the year. And the benefits of the summer home, well that is even simpler: Anna, the best friend of my daughter Kaitlyn.

A college friend of my daughter, the sexy red-head has been a regular by the pool and at summer parties for a few years now, and I am not ashamed to say that she has become a regular part of my fantasy life. Many an evening, working late, I have stroked my hard cock just watching her dive into the pool for a midnight swim. Her body was made for the bikini, to be sure, with her shapely ass and gorgeous tits barely covered by the thin fabric. Cold night air made her nipples stand to attention most nights, and as I pulled harder on my cock I could only imagine sliding my shaft between that luscious pair. Long legs and cock-sucking lips rounded out a package that had been the torture of many a college boy, I had only to imagine.

But what really drove me fucking crazy was Anna’s newest habit of walking around the summer house in the sexiest summer heels known to man. Pair after pair, matched with bare legs or light stockings under a flowing sundress (inevitably bra-less and almost see-through) -- it was almost too much for even this boardroom veteran to manage. Sneaking a glance here and there was all I could muster, though, since she was my daughter’s friend, and the last thing I wanted  was the reputation of a creepy old father when my princess brought friends around.

So I stroked in private, sending streams of steaming love juice into a handy towel.

Until last Thursday evening, anyway. I was working later than usual, even for me. It was a particularly complex deal that I was putting together, and the hours had flown by. I was so engrossed in spreadsheets, in fact, that I did not even hear my office door open and close, despite the quietness of the house. But I did hear the lock click shut, and looking up I was more than a little surprised to see Anna standing there. My cock reacted before even my brain to what I saw: Anna’s red hair shone in the low light. Her heels were spectacular, showing off her legs and ass with cock-throbbing effectiveness. The bikini was barely there, covering only her nipples and with her pussy outlined by a wetness that could, I realize, only have come from a midnight dip.

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“Water was sooo warm,” she purred to me, eyes dancing. “I want to thank you again, Mr. Johnson, for allowing me to come here all these summers.” I muttered something about not a problem, and glad that Kaitlyn had a friend like her to spend summer with. I was much more worried about the raging hard on that was threatening to poke out from underneath my hiking shorts at that very moment than I was about what words I managed to string into a sentence at that exact moment.

“I mean,” Anna said, smile on her face as she walked towards my desk, “that I really want to thank you, sir. I have learned so much by watching you working here, successful in business and a great father. It really does amaze me how you manage to juggle it all, so so well.” Sitting on the corner of my desk now, there was no way Anna could not see the obvious. I was ready to fucking explode when she actually let her beautiful fingers dangle lightly along the obvious bulge that was still growing.

“What really amazes me,” she continued, shifting her weight so that her bikini bottom framed her pussy just perfectly, “is how you seem to manage the pressure so easily.”  Her fingers tightened slightly on my shaft as she spoke. My shorts seemed doomed to split open. Again, all I could do was mutter some lame response.

“I know,” she smiled. “I can pay you back for all your hospitality with a bit of pressure relief.” Sliding from the desk, she settled to her knees, facing me, hands on my thighs. I froze, cock upright, holding my breath. I felt my shorts being pulled down, and my hardness springing to attention in the cool night air.

I swear to god, Anna purred.

And before I could say a word, her tongue was tracing the length of my shaft, licking my cock and balls as though they were an ice cream cone on a hot summer day. I gave up, leaning back in my chair and simply closing my eyes. Anna’s lips and tongue were magic as she caressed my shaft gently, devouring my hardness as though this was best cock she had ever tasted. Harder and harder I got as she continued teasing me for what seemed like hours. Slow then fast, hard then soft, her fingers stroking my shaft then letting go slightly just before I exploded.

And then, with a quick flick of her fingertips, off popped the bikini top, releasing those tits I had fantasized about for so many hot, sticky nights. Anna guided my body forward slightly, and in doing so positioned my cock head just between her tits. “Fuck them, Mr. Johnson. I know you want to. Fuck them.”

So I did. As Anna squeezed her tits together, I ran my shaft between them in long, slow strokes at first. As I did, my fingers pinched her hard nipples, which made her moan loudly now. Thank god Kaitlyn was a heavy sleeper at the far end of the house. Anna’s moans drove me fucking crazy, and I began to drive my cock faster now, fucking her amazing tits as she gripped the corner of my desk.  

I shot my first stream of cum across her face without warning, catching us both off guard. I drove my cock forward as the next stream covered her face. Closing her eyes, she opened her mouth wide, and I continued, shooting stream after stream of warm cum onto those beautiful lips. When I thought I was almost drained, any took her long fingers and milked me for even more.  I shot load after load. almost passing out from the feelings vibrating down my cock into my body.

I fell back in my chair exhausted. Anna simply giggled, and rising from her knees, leaned over to kiss my lips lightly. The next sound I remember was of her diving quietly into the pool, letting the warm summer water wash over her. I smiled. Business is good.

Owning Anna II

Dominance was not natural to me, but it sure came naturally in my relationship with Anna. From the first time my hand slapped hard onto her amazing, soft ass, spanking had become a go-to for us during any sex. My cock had never gotten harder or thicker than when I spanked her, and I know that Anna had never climaxed more intensely (or loudly) than during one our spanking sessions. The first time we came together as I punished her ass with my hand was so intense that we both found ourselves exhausted to the point of giddiness.

Now things were evolving again.

Having mounted my raging cock in my favorite reverse cowgirl, Anna was riding hard and deep, her moans filling the room. My right hand slapped her ass hard, leaving a red spot and I heard her gasp, her pussy shivering on my shaft. I raised my hips, feeding her my cock now, forcing her to take me deeper still. It was at that moment that I grabbed her long red hair, and snapped her head back viciously. I heard her gasp loudly, but she never missed a beat, driving harder still on my cock, her pussy juices flowing.

Looking in the dresser mirror, I saw what I had created. Her back arched backwards as I pulled her hair harder know, Anna’s glorious tits were on perfect display. Bouncing as she fucked me, they were amazing. Nippples hard, tan lines silhouetting the perfect curves. In that moment I saw Anna’s tits for what felt like the first time. These were the same tits that I had sucked on, played with, pinched many times. But they were also different now: they were my tits, totally under my control and my power. I almost shot my entire load at their magnificence.

Lower in the mirror, the image of her wet pussy sliding hard and fast on my rigid cock, her legs bent back as she slammed harder than ever before. I tightened my grip on her hair, and watched the image in the mirror adjust her balance, putting more of her body in my control and using my cock as her balance. I lifted adjusted my hips, my balls swinging madly as Anna rode harder and harder.

Anna’s fingers moved to her clit as she rode me. I watched her fingering herself skillfully, bringing herself closer and closer to a crashing climax. Pulling her hair hard again, I thrust my cock savagely into her pussy. Her fingers worked furiously, her screams rose.

We came hard together, and I released my grip on her hair just as the first geyser of my cum filled Anna’s pussy. Sitting upright, she settled onto my balls and shaft, her juices covering them. I came for what felt like forever as Anna’s pussy caressed every ounce from me. She was covered in perspiration, exhausted and still quivering on my shaft.

“Oh my god,” was all I heard her say.

~ Sir D.Q.

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