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LeaveYourHighHeelsOn
Moon
- Joined
- Feb 11, 2025
Long-Form ( 3-5 paragraphs) | Long-Term | Discord or BM DM Friendly | Slow-Burn
Disclaimer - Despite the prompt below, I am open to your character being a MILF, Cougar, GMILF and even a Trans Cougar.
Okay, listen—I get it. You're not gonna believe a word of this. Hell, I wouldn't believe me either if I wasn't the one living it. But trust me when I say this summer was straight-up insane. And the craziest part? I actually landed myself a girlfriend. Yep, that's right—a real, genuine, "please-check-I'm-not-hallucinating" girlfriend. Suck it, haters!
Okay, fine. Maybe calling her my girlfriend is overselling it. It's more of a secret summer fling—emphasis on secret. There's no chance this thing makes it past September. October at the latest. Why, you ask? Well, aside from me being nineteen and her being...let's just say a little more "experienced," there's also one minor detail: she's my best friend's mom.
Yeah. Let that bombshell explode for a second.
Now, before you judge too hard, remember I'm an adult here. Old enough to vote, join the military, pay taxes, and waste money on college textbooks. Totally legal—totally legit.
But hold on, let me rewind. I graduated early from high school—not because I'm some gifted genius, but just because I busted my ass studying. Somehow, against all odds, I got accepted into my dream university—yeah, Ivy League, baby—but it's right here in my hometown. So, I'm stuck living at home, surrounded by people who've known me since I wore diapers. And guess what: college girls? They apparently have zero interest in younger dudes. I drop my age, and they ghost me faster than my motivation to attend morning lectures.
So, out of sheer boredom and borderline desperation, I downloaded this dating app someone recommended—the one aimed at older women looking for younger guys. Figured why the hell not? It's not like I had anything to lose besides dignity, and that ship had sailed a while back anyway. Weeks passed, and the app was a wasteland. Crickets, tumbleweeds, awkward silence. Then suddenly—you showed up.
And before you accuse me of being creepy, let me clarify: I genuinely didn't know it was you when I swiped right. Your profile picture didn't exactly scream "soccer mom on laundry duty." Nah, you looked completely different. Confident as hell, perched on a bar stool in a cocktail lounge, wearing this sleek, curve-hugging black dress that hit your thighs just high enough to tempt the imagination. You were dolled up in a way I'd never seen before—bold makeup, fancy jewelry, nails done in this glossy deep red, and holy hell—those shoes. Nude colored Five-inch platform peep-toe heels with the sexy red bottoms. Your perfectly painted toes just barely poking out, etched into my brain forever. I guess that's when I realized, yeah, I've got a high heel fetish.
You looked real—and I liked that. You had curves, full thighs pressed against the barstool, hips that confidently filled out the dress, and a soft, inviting figure that made me think about stuff I definitely shouldn't be thinking about my best friend's mom. You weren't exactly slim, but you carried it so damn well. Sexy in that totally approachable, "hot-mom-next-door" kind of way.
Then, my phone buzzed:
"OP, seriously, why the hell did you like MY profile?!"
And in that instant, realization hit me like a truck—holy shit, it's you. My best friend's mom. Cue internal panic, existential dread, and a rapid-fire self-interrogation of my life choices. But then, something weird happened. After a few incredibly awkward exchanges, we started chatting—like, really chatting. I don't know, maybe it was the thrill of the forbidden, maybe it was the anonymous vibe of the app, but somehow, we clicked.
Eventually, fueled by reckless teenage courage and sweaty palms, I made my move:
"Wanna grab dinner sometime?"
My hands were shaking like the first time I tried sneaking booze from the liquor cabinet, but you didn't see that through the screen. Your reply was quick:
"Oh, screw it—why not? Everyone else on here is a creep, and honestly, you're probably the smartest guy who's liked me so far."
Cue internal screaming and victory fist pumps. But then you immediately followed up with:
"But you CANNOT tell your mom. Seriously. She'd kill me. Hell, she'd kill us both. Let's pick somewhere discreet—how about The Arbor, that little place near the Ritz?"
And just like that, our scandalous, secret summer romance was born...
Over the next few months, our characters plunge headfirst into a reckless, hilariously awkward, and deliciously forbidden relationship—packed with clandestine hotel meet-ups, secret dates, adrenaline-fueled near-misses, and daring encounters in the most questionable places imaginable. Yeah, even at my best friend's house (okay, yeah, I know—I'm a shitty friend, sue me). It's messy, it's tense, and it's got some comedic charm.
Our Dynamic
I'm craving something oddly wholesome, but with an unmistakably naughty twist. My character is inexperienced—like embarrassingly, cluelessly innocent—and yours would eagerly step in to help him finally pop that infamous V-card. From there, though, our dynamic shifts in unexpected ways. My character becomes utterly devoted, determined to learn every secret and skill necessary to fully satisfy his "queen." You. Plus, my characters got way more stamina than any other guy your age! Don't believe me, lets test it!
Perhaps your husband has died. You're recently separated. Or even in an affair.
It's a weird match, an unconventional romance forged entirely from unique timing, laughably poor judgment, and undeniable chemistry—but somehow, it just works.
What I'm looking for
I'm looking for a long-term, long-form roleplay partner—someone who thrives on crafting detailed, descriptive, and vividly immersive scenes. If you enjoy writing with some humor, nuance and a bit of playfullness than we're going to get along real well. I love writers who can breathe life into characters, who can balance steamy intensity with laugh-out-loud moments, and who genuinely enjoy building an engaging story together over time. Plus, someone who enjoys writing about fashion, or at a minimum who enjoy wearing high heels will be very appreciated!
If that sounds like you, let's connect—I promise it'll be worth your while.
Kinks - Yes (Not a all-inclusive list, just the heavy hitters)
High Heels - Girls my age don't like to wear them, and I encourage you to wear more of them. Why not, you look hella good! Especially when you wear them casually!
Outfit Play - From dressing up, lingerie, costume parties, roleplaying (in a roleplay), or simply casual outfits - we have our work cut out for us as we accessorize our characters
Seduction - Applies both ways, sure you're the hot MILF. But I've got youth, charm, eagerness and enthusiasm - when was the last time you had something that longed for you?
Dirty Talk - You know the drill
Anal, Vaginal, Oral - I never knew you wanted to try anal?! And you swallow? Can I cum on your face too? What? Why are you walking away?
Sneaking Around - Its going to be frowned upon, making out with your boyfriend if he's 20 years younger than you. So hotels, dive bars, and well...your own house become all fair game
Risky Sex - What? Me going down on you at your own house, with your son in the other room isn't exciting enough for you??
Foot Play - Yeah i know, because ass, tits, pussy and lips aren't enough. Why not?! We're experimenting!
Limits - Scat, Death, Violence, Humiliation, Pain.
High Heels - Girls my age don't like to wear them, and I encourage you to wear more of them. Why not, you look hella good! Especially when you wear them casually!
Outfit Play - From dressing up, lingerie, costume parties, roleplaying (in a roleplay), or simply casual outfits - we have our work cut out for us as we accessorize our characters
Seduction - Applies both ways, sure you're the hot MILF. But I've got youth, charm, eagerness and enthusiasm - when was the last time you had something that longed for you?
Dirty Talk - You know the drill
Anal, Vaginal, Oral - I never knew you wanted to try anal?! And you swallow? Can I cum on your face too? What? Why are you walking away?
Sneaking Around - Its going to be frowned upon, making out with your boyfriend if he's 20 years younger than you. So hotels, dive bars, and well...your own house become all fair game
Risky Sex - What? Me going down on you at your own house, with your son in the other room isn't exciting enough for you??
Foot Play - Yeah i know, because ass, tits, pussy and lips aren't enough. Why not?! We're experimenting!
Limits - Scat, Death, Violence, Humiliation, Pain.