The following is a work of erotic fiction and is in no way meant to represent real people or events. It is completely written and owned by me, OfStarsAndDreams.
Contents (includes possible spoilers): M/f, cuckolding, manipulation, irredeemable asshole MC, older woman/younger man, homewrecker, casual fucking, gym, public sex (mild), seduction, pick-up artist, massage, over clothes petting, fingering (M on f), oral (M on f, f on M), orgasms, questionable consent, non-consent, mouth fucking, PiV sex, negging, creampie, fluids, coercion, no doesn't mean no, lips that grip, raw sex, bdsm (very mild, controlling M), commands/demands (M to f), begging (f to M), dirty talk, forceful oral (f on M), swallowing, forced down and fucked, rough sex, on phone while fucking, teasing, hair grabbing, dripping cum, caught in the act, clothing destruction, cervix pounding, impregnation (not stated in story, suggestion of it occurring is made)
Let's begin!
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I think most people would agree that I'm not a very good person.
I'm certainly not trying to be.
If it makes you feel better you can blame my dad, or my stint in the military, or whatever other Freudian bullshit floats your boat. Honestly, though? I was probably just born this way. I mean, there are plenty of men like me out there. I'm just more honest about it. At least with some people, anyway.
Which is why, in the start of this recollection, I had come to find myself in a predicament regarding my Thursdays.
You see, I really like getting my dick wet. Who doesn't? But I really hate having to deal with all of the emotions, all the baggage, the women suddenly having expectations of me, so on and so forth. My ideal, then, was someone eager to put out but disinclined to try to work their way into my personal business. No strings attached.
Yeah, me and everyone else, right?
Except, in my case, I'm fit as fuck, hot, charming, and, like I said before, I don't give a shit about what anyone thinks of me. I have no problem pulling pussy and I have no qualms with blocking their numbers after I pop a load off in them, or maybe a few if they're a really good fuck and not especially whiny about shit.
Landing a new girl every night can be a bit of a chore, though, which is why I really came to appreciate my job at the gym. It's like a buffet of neglected, insecure housewives all trying to get in shape so they can pretend they still look as good as they did in their twenties. And they're usually as regular as clockwork. Sharon, for instance, comes in for personal training on Monday mornings and Reba on Monday afternoons, so I could straight up be banging Reba with my dick still wet from railing Sharon and naive little Reba would honestly think she was so special that she was the only piece of ass I was getting there. I mean, that is what I told her, after all.
I could line up one or two holes every day of the week with none of them any the wiser.
Of course when I first started I mostly had eyes on the tight young gym bunnies -- and I'll still snap one up in an instance whenever they avail themselves to me -- but over time I learned to enjoy how reliable, desperate, and incredibly easy to manipulate the older women were. Plus, the young ones have egos like you wouldn't believe. They might be horny but damn do those bitches act like they're doing you a favor. On top of that they always make things so god damn complicated. A married woman, on the other hand, is going to put in the effort to make sure things stay on the down low. Hell, she'll do most of the work for you.
Which brings me back to Thursdays. You see, that was the day of the week I'd assigned to fucking this ex-beauty pageant trophy wife, but I guess the guilt of cheating on her husband finally got the best of her, or else hubby found out and kicked her whore ass to the curb. Who knows. But she hadn't been showing up, and I had realized I needed a new girl to fill the position.
It's always a bit of a careful thing at first -- I have to test the waters, see who's willing, make sure my boxes are checked before making a move, lest one of them freak the fuck out and report me for sexual harassment and cost me my job and, more importantly, my calendar line up of eager pussy.
At the time there had been a couple girls on my radar, but the most promising option was Tammy. She'd hired me as a private trainer, so I had plenty of time with her. She wasn't anything special, a bottle blonde in her fifties, overly concerned about appearances. Her husband was some rich upper-class ex-serviceman, an officer. I won't deny that I find a certain added amusement in the thought of using the wives of rich and powerful men as my personal toys. These men think they have everything, hold all the power, and here I am just walking all over them, dirtying their most prized possessions right under their noses. I'm pretty sure there's even an oblivious CEO out there raising one of my kids.
Just thinking about it gets me a little hard.
Anyway, the first thing I did with Tammy dearest was see if she'd be game for some extracurriculars during our sessions. I put her in positions that got her close to my hard thighs, my bulge in those tight gym shorts, situations that brought my body a bit too close to hers, and each time I noted her reaction. In cases where it wasn't ever going to fly the filly will look uncomfortable or flighty -- they'll edge away, squirm, not look, try to make distance.
Tammy, however, did the opposite. She'd blush, and hold still, and linger, and even occasionally shiver at my touch. She'd fidget during sessions, throw me glances and quickly avert her eyes. Play with her fucking hair. It was as good as in the bag.
Once I determined the fruit was ripe for the picking, I decided to step a layer deeper. I put her in a bit of a compromising stretch, something that required a bit more out of her than she was used to giving, and, as a nice bonus, put her ass in the air in those nice tight yoga pants of hers. I could see the way they wrapped around her pussy like the whole thing was vacuum packed. By the look on her face she was probably thinking the same thing.
So I leaned in and teased her a bit, told her that she must not have a very exciting sex life if she couldn't even handle a pose like this.
Her reaction was delightful -- she nearly fell over right there and then -- and I knew my suspicions were spot on. Caught her. She looked away, embarrassed, and anyone with eyes could tell she wasn't getting anything good at home. Maybe not getting anything at all. When was the last time this woman had an orgasm?
Time to start sealing the deal. I put on my most charming but sympathetic face, like I felt bad for bringing it up in the first place, and asked how her husband could resist sleeping with such a pretty lady as herself.
Gag me.
And then I waited a week. You can't rush these things. I gave her time to sit on it, to let it brew inside her, grow and simmer. There's still a chance that a woman will show aversion at this point, escape the hook, and then I'm forced to make a clean break and back off. But I was pretty sure this one was in the bag.
And I knew I'd won the game when she showed back up the following Thursday with a touch of makeup and her hair more carefully arranged. Nothing too serious, nothing to make it clear she was trying, but obviously in an effort to make herself look more attractive.
Which is why I spent the day doing leg exercises, and why afterwards I offered her a nice, deep tissue massage. I started on her lower legs, working them over, positioning myself between them, then moving up her thighs, sliding my hands smoothly over them, running them up alongside the mound of her pussy, up over her hips, grabbing the meat along the inside of them. I could hear her breath increasing, could feel her legs twitching under my grasp, could feel the heat rising from under the crotch of her leggings, the inside seam growing damp with her longing.
And only then, did I finally, slowly, deliberately, run my hands over the mound of her pussy itself. She gasped, shocked and stunned, but didn't pull away. She hadn't anticipated her little fantasy actually coming to fruition, but she was too swept up in it now and didn't want it to end. Maybe she'd feel guilty later but right now she was much too horny to tell me to stop. I dutifully teased and rubbed through the leggings, carefully at first, as if my questing hands were beseeching her, like I was seeking her permission. Not that I gave a fuck. It's just the method. All I care about is keeping them from freaking the fuck out and things going south.
Once her hips were starting to buck, after she'd given herself over to allowing my manipulation of her body, I started sliding my hands down her pants, pulling them, sliding them down her body. Another careful moment, to be handled with calculated precision. She startled again, almost pulling away, telling me no, you can't, and other such useless defenses against my intrusion. It's not like she was doing anything to stop me. I just reassured her, told her everything was fine, soothed her down like some dumb animal, and dipped my fingers between her wet lips.
She gasped so loudly when I stroked her clit that I wondered if the bitch even masturbated.
I fingered her a bit, to get her acquainted with the idea of being touched, then lowered myself to my knees and went properly down on her, hooking my fingers inside her as I lapped at her clit. When she came her thighs squeezed tight around my head and her pussy walls clamped down around my fingers. I kept working her, making sure to keep her machine revved and not let it cool down just yet.
And then I got up and dropped my own pants. She immediately balked. Of course she did, I wasn't exactly surprised. It's one thing to be done unto and another to actively participate in your own act of cheating. I was ready for this though. I moved in close, bringing my cock closer to her face, and stroked her chin and hair, cooing at her. It's only fair, right? I got you off, are you going to leave me hanging like that?
She started saying this wasn't something she did, how she didn't like doing it, but at the same time I was slowly pressing my dick to her lips, and soon her mouth was parting and wrapping around my cock. She was clumsy at it, probably hadn't been lying about not doing it, but it took very little coaxing at all before she let me grab her hair in my fist and start pumping my hips into her mouth. I could hear her little gurgles and chokes, watched as her eyes get a bit misty from fighting her gag reflex as the head of my cock pushed down against the back of her throat.
