All In The Family. No, Not My Family.

A while back I had gotten into the business habit of keeping a high capacity flash drive on my keychain.  Well, sure enough one of the reasons I no longer do so is because I sometimes, in a rush to head out from my office to appointments, or while finishing up an appointment, forget that the flash drive is still plugged into the computer.  My car is keyless and I keep the fob separate from my keys.  Or at least I did then.  I'm much more organized now.


"Get to the sex, Dolly!"


In case a little voice in your head was saying that to you as you read the first paragraph, not to worry.  The little voice inside MY head was screaming the same thing.  I love writing about my adventures.  Not quite as much as I enjoy the adventures themselves, but....


Okay, so one day I go running back in to my office an hour later, thankfully the appointment was a cocktail hour just two blocks away from the high rise where our offices are located, and it was easy enough to go back to the office and retrieve my keychain, since I hadn't made it all the way home.


And while most of the lights were out, a few were on, so I knew I wasn't alone.


The door to Chuck Smith's office was closed.  But the noise from the other side of the door told me he wasn't alone.


The sounds also told me that Chuck was getting laid, and the gal on the receiving end of Chuck's "hard" work (pun intended) was having a glorious time.


"Oh God Chuck, don't stop, yes, mmmmm, oh fuck Chucky, just like that, right there...."


Did she say "Chucky?"  Oh I had to listen.  "Chucky" was in his early sixties, had practiced law and then become in-house counsel and brokered deals for us, and now he was a senior partner and a rain-maker.  He had a middle aged tummy, nothing terribly obese or anything, had a bald spot that was partially covered with a comb over that wasn't all that bad, and he was maybe five foot eight, barely taller than me and if I wore heels, which I often do, I was taller than him.  He was married, and his wife was old money.  She was a first wife, and the children and grandchildren came by occasionally.  I didn't know "Chucky" played around.  From the sound of whomever his paramour on the other side of the door was, maybe I needed to familiarize myself with Chucky's personal life a bit more.


"Fuck, Chucky, fuck my married pussy, fuck your hot cock into me again and again....oh! aahhhh, mmmm, uuumpphh.... God don't stop."


And then some operatic cries and high notes that made it clear she'd cum.  Hard.


The absence of words made it easier to hear flesh slapping against flesh, some furniture sounds from absorbing the pounding.


I was sooooo wet listening to this.  I'd never had a sexual thought about Chuck Smith before.  And I'd never be able to look at him and not think of "Chucky" the excellent fuck buddy again.


How I kept my fingers out from under my skirt I can't recall. Someone was going to get laid tonight with me.  


"Oh God, not again, mmmm, how the fuck are you still hard?  Mmmmm, ahhh, shit, yes, yes, just ....yes, you own me, keep fucking me, oh Christ I think I'm going to cum again..."


And then the opera started back up.


Not a word from Chucky meanwhile.


Finally, maybe thirty minutes after I'd arrived (30 MINUTES!! Talk about "me love you long time"!) and don't forget, I don't know how long they'd been going at it before I got there, the sex noises, the banging and panting stopped.  A couple more Aria's had been sung by then I should add, and then instead of a fat lady singing (God, I hope the woman getting scrogged in there wasn't a fat lady---I just wanted to use another opera reference about the concluding sounds) I heard a deep voiced man grunt and groan, but no words.  Chucky had earned his orgasm big time from what I heard on the outside of the door.  I slipped away to my own office, and used a hand mirror strategically angled to get a glimpse of who came out of Chucky's office.


It didn't take long.


Angie!  Angie Smith, I should say.  Chuck's daughter in law, holy shit this was hot!  He was fucking his younger son Ted's wife.  How the hell long had this been going on?  My mind was everywhere.  Had Chuck fathered his own grandkid, since Angie had a child of her own from that "married pussy" that she'd given over to her father in law.


So dirty.  So taboo.  Angie was very attractive, a junior leaguer, private school, this was totally unexpected and exciting.  She looked pretty well put back together considering the major fucking she'd just had.  She stepped into the hall, then turned and leaned back in, I guess to say her goodbye to the man who'd just taken her to pleasure-town about four times.  That deserved a good bye kiss, for sure, I thought.


I heard her say, "You outdid yourself this time. Christ, and now I'm sore and horny all at the same time you bastard.  God I love your cock."


Then I heard him, but it was muffled from inside the room, and then Angie spoke again.  "Yes, Teddy has a sleepover that night and as long as you can.  Hey, this was pretty, all the lights of the city coming in from the windows after sunset while you give it to me good.  So glad I sucked you off first, you lasted soooo long inside me."


Yeah, upon hearing that, I did take my hand that wasn't holding the mirror and start frigging myself.  Angie was about 5'4". blonde hair to her shoulders, blue eyes, about a C cup and a trim, fit, figure from going to the Pilates classes and whatever else daughters in law of rich powerful men do.


Okay, wise guy, so I'm the daughter of a rich, powerful guy, and I take yoga and go to the gym and I'm in shape, too.  I'm speaking about other women, not me. 


I heard the final kiss and goodbye.


And then a minute later he came out of his office. Heading in the direction of my office.  My office with an open door.


And it wasn't Chuck Smith!  At least, not Chuck Smith, Sr., the man I'd told you about.  It was Chuck Smith, Jr., the older son, the older brother of Angie's husband, Ted Smith.  I got it now, "Chucky".  Maybe that was the pet name in the family for Junior.  He was in commercial real estate, his father's connections got him started, and his father invested in his deals and they did well.


"Dolly I know you're there, can we talk, please?"


Holy shit!  Busted by the adulterer I was enjoying spying on.


And into my office walked Chuck Smith, Junior.  I think he also went by Chuck and if both Chucks were in the same room, words like Dad, son, junior, and senior helped the two of them and whomever they might be with know who was talking about whom.  Late 30's, trim figure, did 10K's so I'd seen him around, even a mini triathlon if I recall.  Good looking, married, two kids, and fucking his sister-in-law in his father's office.


"Dad's general counsel, he has security camera hookups to his monitors and I left that on when Angie and I got busy.  I know you heard and that you've been here a while, Dolly.  Twenty four cameras per floor, so I had a couple angles on you.  Apparently you like what you heard, you can take your fingers off your clit now, Dolly.


Cocky bastard, ya think?  Just got caught and he's bossing me around.  We'd only met a few times.


Tell you the truth, it was turning me on how confident he was even under these circumstances. 


"How do you even know I'm Dolly, anyway?" I asked him, trying to get control back of this situation.  His chest was still sweaty looking through his unbuttoned shirt, his pants were tight and showed his munchable ass and a decent sized package bulge. "And what's the deal with fucking your brother's wife in your father's office? this isn't your playpen."


Playpen?  Oh, he had me flustered all right.  I was noticing his hands, they looked strong, nicely groomed nails, the type of hands I love to, well, manhandle me during sex.  Could he smell my interest?  Could I, or was I just worried that he could.  I didn't even know.


"Dolly," he started, walking closer, and suddenly taking my hand, the one I'd been touching myself downstairs with, in his, "is there a red blooded man in South Florida running races, entering triathlons, or making up excuses to venture up to his father's office down the hall from you who doesn't know you and wonder what it would be like to fuck you?"


I knew I'd let him have his way with me a moment later when he raised my hand, sticky sex-twiddling fingers and all, to his lips.  He looked me in the eyes as he sucked my pussy flavor off my fingers. Then he released my hand and stepped closer.  Only later did I realize that when he did I placed my hands on his sides, just above where his belt would have been if he'd put his belt back on after fucking the hell out of his sister in law.


"Wanna taste her?" he asked, and I was confused, or just in a trance, what was the difference at that point, as he leaned down to kiss me.


And my confusion went away, it was clear what he meant.  Apparently their sex talk covered the blowjob and I'd heard the fucking, but he'd gone down on her and his mouth was coated all the way around, his chin, lips, over onto his cheeks, with a sexy musky slutty pussy.  I was sucking his top lip, then his bottom.  Shit, was I under a spell?  Did I care anymore?  Hell, I barely realized that the fingers rummaging around in my aching, hungry to be fucked smooth shaved overflowing with desire pussy weren't my own fingers.  And then he fed me his fingers, then used his other hand to get a sampling of me for himself.


"You must have condoms, I know you'll want me to wear one for what we both want to happen."


Not sure why my brain was even needed anymore.  Powerless to resist. Not that he was that hot.  Just that I knew he could fuck like a pro and he was in shape, decent enough looking, give him a 7.5, maybe 8.0 if he cleaned up and was dressed up instead of sweaty and stripping off his clothes.  Oh wait, look over there, he's now tossing my clothes on my office chair and leading me to my sofa.  Hadn't realized he was undressing me.  Seriously, like I was a spectator of my own body.  And approving of the view.


I'd never answered his condom question.  He had the nerve to look in my bag.  My expensive, designer bag, that in fact was a gift from another paramour.  First time a man ever reached inside my bag without permission.  And he found the condoms.


I had to snap out of it.  If nothing else, this haze might interfere with enjoying the sex I was about to partake in.


"Did you wear one with Angie?" I asked, laying on my back, remarkably fully nude, my tan all over body in firm, toned shape, and Chucky's eyes roaming over me with approval, his fingers twiddling me as if I needed more priming of my pump, while he stood, also nude now, between my legs.  No manscaping, he was pretty hairy down there, in fact, and his chest and shoulders were nice, a valley between his abs that made me want to bark like a dog.  "Woof".  I'm pretty sure I just thought about barking, but if I actually did it out loud, he never let on.  But let me say it again, "Woof".


"Your body is fucking amazing, Dolly, chicks a dozen years younger than you, more, maybe twenty years younger, I'm not sure of your age, but younger women would trade bodies with you in a second and holy shit I'd have wanted to fuck you from the time I knew what fucking was, back as a teen whacking off to the Sports Illustrated swimsuit issue, you should have been in that, God you're built to rock."


Then he stepped forward and I had a cock in my face, at three-quarters awake.  "You know you want to suck me."


Again with the confidence.  He was right.


And for the second time I tasted Angie.  He hadn't worn a condom with her.  How did I feel about that?  I was about to protest, maybe my eyebrows were knitted in concern.  But by then, Chuck, or chuck Junior, or Chucky, whatever I was to call him, well, he could read me.


"Yes, I barebacked Angie.  My brother has virtually no sperm, he had cancer and chemo as a kid, he's been fine for like twenty years, but they'd been trying and no luck.  I'm the sperm donor, biologically their child is mine, but legally theirs.  There, not so terrible now, right?"


I'd heard most of that, dick in my mouth and all, tasting a cheating wife's pussy.  Or was she.  Wait....


"So you're fucking your sister in law with approval to give your brother and his wife children?  I'm calling bullshit."  Pretty glad to hear myself speak up with conviction, my consciousness was back.  So at least I'll enjoy the fucking and he's going to wear a condom with me.  But there was no way what was going on was sperm donation.


"No, Ted knows his child came from my sperm and that I've agreed to donate again so he and Angie can have a second.  But the sperm collection process and the implantation and all that, it wasn't working terribly well the first couple tries and I've always thought Angie was cute as hell in her classy, too good for most guys way, and I made an off-hand comment that it was a shame I couldn't just make a direct deposit.  And sonofabitch but she said, "I'm so glad you suggested it first.  Let's just go have a fucking quickie and get me a Smith baby, I'll never tell Ted."


Okay, Chuck's cock flopped out of my mouth when my jaw fell open from the surprise of that story.  Chuck was unfazed, he was now fully hard and he opened the condom.  He held his cock, looked me in the eye, got lined up once the condom was fully rolled over this dick, which upon mouth insertion and close visual inspection was probably just slightly above six inches, maybe six and half.  That made Angie go so wild?  He rubbed his now-protected cock up and down my drippy slit, over and across my clit.  He started talking again as he played with me.


"Well there's a reason you don't play with fire, Dolly, and I was just nervous enough about finally getting to fuck Angie that I couldn't finish.  We fucked a long time.  Or maybe the three times I'd jacked off in the half day leading up to our secret getaway to a hotel kept me from cumming.  But it was long lasting and magic.  She went wild, talking dirty, saying how she felt so slutty, wanted to fuck her husband's brother's raw cock, get knocked up by her brother in law.  Who knew Miss Junior League was a kinky freak?  We tried different positions, and of all things reverse cowgirl was new to her. She was so tight, like I was stretching her, and while I'm thick you can see, I'm not winning any "long duck dong" contests.  Oh god it was fun, Angie kept egging me on, "come on Chucky, Chucky make a fucky, fuck me Chuck, get fucked by Chuck, chucker the sister fucker...."


I laughed at that one.  Check bent over and I bit his lower lip, not too hard, just enough to take control so that he could move his face away.  Which was when I felt his condom clad dick start to wedge itself between my labia.  Oh, the heat was tremendous.


"You like hearing about Angie," Chuck mumbled into my mouth, and half way through that sentence I released his bottom lip from my mouth so he could talk, but I kissed him when he was done saying Angie's name. 


"Yeah, I do, maybe I can fuck her too sometime, but first you should finish what you've started.  Fuck me, Chuck.  That sound enough like Angie for you?  Finish fucking me, and finish the story, too."


Let me just interrupt myself to say in advance I reached down and between Chuck's stud cocksmanship, knowing how to use and how to work a woman, and my twiddling, I enjoyed three trips to quiver and quake land, a/k/a Orgasm City.


And Chuck did keep telling me the story, even as he'd have to pause the story when my body convulsions and tremors grasped his dick tight and pulled him into me.


"So Angie told me she wanted me to fuck her every day until she got a test to tell her she was pregnant.  I told her I recalled from trying to start my own family that we'd been advised every other day."  Chuck was rocking in and out of me, building up his latest sweat, and mine too.  This was cruise control intercourse, and a fine example of it.  


"I think I missed her cycle and we fucked steadily for five weeks and the second month did the trick.  Then we kept fucking the rest of her first trimester until she told me for everyone's sanity we needed to stop.  She'd wear jewelry he'd given her, wear the same tailored clothes she wore to fund raisers and society functions. Such a damn turn on, making a good girl go bad.  Not like you, Dolly, you're a bad girl from day one, aren't you, not like Angie.  Tell me how I'm doing, you're breathing heavy."


I was so wrapped up in the story and the cock up in me that I didn't realize I was panting.  Then Chuck turned me onto my tummy without dismounting, and he was doing me harder, doggie style, I buried my head and mumbled, "Don't stop, lover, fuck me, fuck me like you fuck Angie."


"Yeah, the way I fuck Angie.  So I thought Angie and I were cool, and she had the baby, and the doctor talked about her procedures and no one seemed to be any the wiser. and then Angie texted me that she needed some help with the computer and Ted was out on the boat and could I come over.  I got there and where was the baby, I asked her."


'Your baby you mean, Chuck, the one you fucked into my cervix, filling me with your seed for months, breeding me.  That baby?  He's at your parents, some grandma and grandpa time.  They seem to like grandchildren.  I just liked how I got that grandchild of theirs"  And then Angie dropped to her knees and took me in her mouth, looking so dirty as she reached up and cupped her tits and tweaked her own nipples as she sucked me to hardness and then jumped into my arms and we fucked standing."


I was so fucking hot listening to this.  I told him, "I need to be on my back this time, I want to wrap all my arms and legs around you and look in your eyes as you tell me about Angie face to face."


And we did.  Chuck fucked me missionary, and he lasted through the three orgasms of mine I mentioned.  His stories of Angie being addicted to his cock all rang true.  How she'd given him her ass, and he laughed and said "how's that supposed to get you pregnant?" and she'd commented, "well maybe I'll have an IRS agent for a kid, aren't IRS agents all the product of anal sex, anyway?"  Chuck continued, "I half snorted and half didn't get it, so she explained her daddy was a CPA and that anal sex joke about the IRS was his kind of joke, and there she and I were talking about anal sex...."


Nnow chuck had me thinking about him taking my ass.  Not that night.  But yes, since then, oh dear God yes.


And Chuck proved he knew how to read me.  "You like it back there, too, don't you?  Anyway, I know Angie and I should stop. They want one more child. And feeling your big D cup tits pressed against my chest like this, Dolly, I've wanted to fuck you since....well, I'd never had sex with anyone other than my wife since I got married until Angie, so I guess these couple years I've been fucking Angie, I've been thinking about you, too."


He was getting close to cumming.  My mind was returning to mush after number three just a few moments earlier.


"Again, why me, how, what?"  I gasped questions while absorbing a terrific fucking.


"Saw you at races, social pages, my dad mentioning how good you look when he talks about work, how clients turn to putty in your presence."


And then he stiffened, and filled his condom.  I held him in me a while, our sex parts twitching against each other's.  For strangers, it was a remarkably intimate fuck.


After he withdrew, and used my office's private bathroom (rank has its privileges!) to flush the condom, Chuck was finishing a text when I returned.  "Your wife, or your brother's wife?"


"My brother's wife.  She's seen you at social events, too, Has heard dad talk about you.  Mom looks the other way, just so you know, they're married a long time and she had some health problems.  In case you might ever be into an older man who taught me everything I know about sexing up a woman during some wildly inappropriate conversations over scotch.  Anyway, Angie, that's who I was texting.  She thanked me, let me know she was home safe, everything was cool, thought about what I said about stopping for good when she has another child, and she said she knew it was the right thing to do.  And then she asked how I enjoyed you and if you'd be into a three-way, she hasn't been with a woman since college."

I looked at him.  And as before, he could read my mind.

And then Chuck texted Angie to meet us at the office the next night.



Purely fictional fantasy for your reading pleasure.

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