"I... well... yeah... of course I've noticed you. I mean, not that I'm interested in you \just* because of your looks, but... Yeah, I think you're pretty. Okay, that's putting it mildly. You're fucking beautiful, you know that? (Flustered) Oh, shit... I just said all that out loud, didn't I? (Chuckles awkwardly) Oh, god... But... I'm serious.* Do you have any idea how hot you are?"

This was a request by u/BasilissaAugusta that I simply couldn't turn down. I'd been meaning to write something more vanilla lately, and I'd also been wanting to write an older woman / younger man scenario for a while. So, perfect storm.

A quick note on the title: "May December Romance" typically refers to couples with a sizable age gap, although people seem to differ on exactly how wide that age gap might be. In this case, I thought that the speaker might be a college senior, perhaps, while his crush is a working mother. How large the age gap between them should be is up to you. (There's one line about "classmates" which could easily be changed to "co-workers", if you'd prefer to age up the speaking character.)

Tags: [M4F] [Script offer] [Older woman] [Younger man] [College-age guy] [Single mom] [Babysitting] [After A Bad Date] [Secret crush] [Shy] [Romantic] [Body Worship] [Fingering] [Cunnilingus] [Blowjob] [Fucking on the couch] [Creampie] [Stay The Night] [Script request]

Disclaimer: This is a fantasy post written by an adult, intended for an adult audience only. All characters depicted are 18 or over.

My script repository can be found here. As always, thank you for your interest.

Looking for a similar scenario, but with the characters' genders reversed? Here you are.

​

Addendum: This might be my last script for a while. I was planning on doing one more before Christmas, but I'm not sure if I'm going to make that deadline. And I just need to take a break from script-writing, anyway.

Thanks for reading.

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"May, December"

or

"Falling For A Single Mom After She Has A Bad Date"

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(Sound of door opening and shutting in the distance)

Oh, hey. Back already? Thought you'd be out a little longer than this.

Yeah, no worries. The kids are down for the count. Only took me a few tries before the little imps gave up on trying to sneak out of bed. (Pause) Aw, don't sweat it about the money. You can just pay me back whenever.

So, um, I take it your date didn't go as planned, huh? What was that place you were planning on going to again? "La Cascade"? Oh, ouch. I've... (chuckle) ...I've heard things. Friend of mine went there once. She said they served vinegar in place of wine, and that the lobster was so undercooked, it looked like it was ready to walk off on its own, so it's no wonder... um...

(He trails off, noticing how upset she looks. It doesn't take him long to deduce that it must have something to do with her date ending so early)

(Placing a hand on her shoulder) Hey... are you okay?

Your date left before the meal even got there? You're kidding, right?

...He said *what*? (Scoffing) Jeez... what an ass.

(Concerned) So... I take it you didn't eat much?

Yeah, me neither, to be honest. I'm famished.

(Snaps fingers) I've got an idea. I know this place not far from here which does some kick-ass Chinese. We could just order out and watch something trashy on TV. Sound good?

(She asks him if he isn't headed home)

No, I don't mind staying longer. And I'm pretty sure we could both use a break right about now. So, what do you think? (Smiling as she agrees to his plan) All right, I'll call'em up. You just make yourself comfy on the couch.

Oh, hey. While I'm in the kitchen, can I get you anything to drink?

Sure, I know which one you like. Cabernet, right? Be back in a sec.

(A moment passes while he calls the restaurant. He then rejoins her at the couch, handing her a glass of wine before sitting down next to her)

And... there you are. Food's on the way, so all we've gotta do is wait.

No, that's all right. None for me, thanks. I *did* help myself to a beer, if you don't mind.

So... what are we watching? "World's Greatest Fashion Disasters"? (Laughs) Yeah, that sounds pretty trashy, all right. No, I'm not judging. You should see some of the things on *my* Netflix queue. It's nice to zone out over brainless stuff like this sometimes. Especially after a crummy date.

It's been a day and a half, I can tell. So, let's make a deal. No stress allowed tonight. All right?

(With a hint of uncertainty, as he worries that she may find his next suggestion a bit too forward) Hmmm... You seem pretty tense. Um, how about I give you a foot massage? Would that be okay?

(Laughing) Yes, I know you're just paying me for the babysitting, but... come on, I insist. You've been wearing those heels all night. Your feet must be killing you.

(Sincerely) I wanna help you relax. The food's not gonna be here for a while. Might as well make ourselves comfy, right? (Teasing, enticing) Besides, I give world-class foot massages. *Promise*.

(More teasing) I'm not hearing a 'no'... (Encouraging) Go on, put your feet up.

(She finally agrees to the foot massage, placing her feet in his lap, a little uncertain at first, before relaxing and letting out little sighs of pleasure as he gently massages her feet while she watches TV and enjoys her glass of wine)

(Smiling) There you go. Doesn't that feel good?

(She gives him a smile and a nod, silently urging him to go on)

It doesn't tickle, right? (Grinning) I promise I won't. Scout's honor. (Teasing) Although... I *am* mighty tempted, now that I've got you all vulnerable like this. (Laughing, as she gives him a look) I really won't. Cross my heart. I'll just keep on massaging them like this... How's that?

(He continues to knead the muscles of her feet for a moment, quietly enjoying the sight of her finally let go of all her stress and simply unwinding)

You look way more relaxed. It's nice seeing you like this. You always seem like you're going at a hundred miles an hour, physically or mentally. You've gotta remember to unwind from time to time, you know?

(Shyly) Is it okay if I move up a little further? Yeah? All right, let's move on up to your calves... Does that feel good? (Smiling) Okay, I'll keep going, then.

(Breathy) You're awfully tense... Feels like you really needed this...

(She asks if he isn't getting tired) Tired? Me? No, not at all. I *love* giving massages. (A little flirty) I could keep going all night...

(Realizing that their conversation is turning rather flirtatious, trying to change the subject) So... that date of yours sounds like he was a real toolbag. I mean, who just walks off like that?

Seriously. Don't worry about it, babe. There'll be plenty more dates for you, and we men aren't *all* jerks. You'll see. Hashtag "not all men"! (Chuckles awkwardly)

Hmmm? Me? No, I'm not seeing anyone right now.

That special someone? Not really. No, I mean... there's one or two girls in my class that I like... you know, in a friendly sort of way. But... no-one like that.

Well... since you ask, there *is* someone. I've... kind of had a crush on her for a long time now.

(Chuckles) Anyone you know? I... guess you could say that.

But... I don't know if she'd be interested in me.

(Shyly) Why? Well, she's just... She's a bit older than me, and... it's hard to explain, but... it just feels like she's *way* out of my league. Honestly, I think she might just laugh me off if I ever told her that I'm into her.

Is she pretty? Oh, *yeah*. Like you wouldn't believe. And there's just... (inhales, exhales slowly) there's just something about her...

(A little more casually) But hey, don't worry about me. We were trashing *your* date, weren't we? Or maybe we should start planning your next one? I'm sure you're beating off potential suitors with a stick.

(She brings up her date again, and how he brushed her off)

That guy was an ass. Forget about him. He didn't know what the hell he was talking about. Must've been blind or something...

(She remarks that she's not feeling very attractive after what happened tonight, and wonders aloud if she's simply past her prime)

(Disbelief) "Past your prime"? What are you talking about? Have you *looked* at yourself in the mirror lately? You look even more beautiful tonight than usual.

(She gives him a funny look, and he realizes what he just said)

(Awkwardly) I... well... yeah... of course I've noticed you. I mean, not that I'm interested in you *just* because of your looks, but... Yeah, I think you're pretty.

Okay, that's putting it mildly. You're fucking beautiful, you know that?

(Flustered) Oh, shit... I just said all that out loud, didn't I? (Chuckles awkwardly again) Oh, god...

But... I'm serious. Do you have any idea how hot you are?

Yes... it's you. I've had a crush on you ever since I first saw you. You were playing with your kids in the park, laughing as they kept running around you in circles. You glanced over at me, stood up, smiled and waved. I could've sworn I forgot to breathe then and there. The way the sunlight framed your figure in that pretty summer dress of yours...

And I just kept falling harder and harder for you since that day. It was all the little things. The way you just radiated confidence and... sensuality.

I always wanted to say something, but I just didn't know how. I just figured... you wouldn't be interested in some young, naive guy like me.

I'm not joking. Do you know many guys would kill to be in my shoes? To get to hang out with a smart, confident, sexy woman like you? Do you know how lucky I am right now?

I was drawn to it all. Your looks. Your experience. Your maturity. And, oh god... don't get me started on the way you dress, the way you carry yourself. It's not like you always go for the most revealing clothes, but... everything you pick out to wear just hugs your curves like... (sighs with pleasure) it just... drives me crazy.

(Shyly) ...Can I move a little further up?

("Well, I don't know. *Can* you?", she teases him)

(Chuckles) Sorry, ma'am. *May* I move a little further up?

(Quietly, as she encourages him to move his hands up to her thighs and explore, as the last vestiges of pretense of it being merely a platonic massage fade away) Okay...

(Breathy) Is that good? I can't believe I finally get to do this. To touch you like this... Run my hands up and down your divine body... Do you have any idea how long I've wanted to do this?

(She suddenly has second thoughts about their age difference, and asks him if he's okay with that) I don't care about the age gap. I really don't. I want you. Yeah, you're older, but that just means you're more experienced. Not everyone appreciates that. But I do.

(He moves further up, leaning in close to kiss her) And you are so, very... (kiss) *very*... (kiss) attractive...

(Sounds of making out for a while)

God... your perfume is driving me wild...

(More kissing)

(Soft chuckle) You shivered. Do you like it when I trace little kisses down your neck like that? (Grinning) Maybe I should do it again... (He continues to trace kisses down her neck while touching her full breasts through the fabric of her dress)

(Breathy) God... your nipples are getting so hard... Can I pull down your top?

(She bites her lip and nods. He pulls the top of her dress down, exposing her breasts)

Oh, wow... they're perfect... Does it feel good when I massage them like this?

Can I... suck on them?

(She encourages him to do so, softly pulling him down towards her bosom as he leans down to kiss and suckle on her breasts)

Mmmhhh... they taste so fucking good...

Do you know how often I've fantasized about doing this? How many nights I've been lying in bed, stroking myself to the thought of pleasuring you like this?

You... you want to do something for me? O-okay...

(He tenses up for a moment as she reaches inside his pants, gently stroking his erect cock while he continues to massage and worship her pert breasts)

Oh, fuck... that feels really good... (moans) Your hand on my cock, slowly stroking me off while I... Mmmhhh (breast suckling sounds continue for a moment)

(Spoken as he continues to massage and suckle her breasts, circling her pert nipples and aureoles with his tongue)

Mmmhhh... I could keep doing this all night...

I love the way you taste...

The way you feel in my hands...

Is it okay if I move a little further down?

...Yes, ma'am.

(He slides down to between her thighs, brushing his hands underneath her dress, feeling the wet spot on her lacy panties)

Looks like I'm doing something right. Your panties are getting all damp.

God, you look so cute when you blush like that.

Can I take them off?

No, don't argue. Let me do this for you... Please...

(Sliding off her panties, admiring her exposed womanhood)

It's beautiful... just like you.

Now, let me just get a taste...

(He leans down and slips his tongue inside her wet pussy, licking and fingering her, eliciting deep moans of pleasure from her)

(Breathy) Oh, my god... your pussy tastes like heaven.

I can't believe I finally get to do this.

(She gently holds his head in place, digging her fingernails into the back of his head as he continues pleasure her)

Does it feel good when I finger you while tongueing your clit like this? Yeah?

(She urges him on, cooing at him about how good it feels as he continues to stimulate her to an orgasm)

How about two fingers? Is that too much?

No? You want me to keep going? (Smiles) Okay...

Your pussy tastes so fucking good...

Are you... are you getting close?

Okay... come on... cum for me... it's okay... do it... cum for me... come on...

(He speeds up, urging her to cum. Cunnilingus sounds continue for a while, until she finally reaches her orgasm, writhing and spasming under his ministrations, before finally coming back down)

Holy fuck... that was quite the reaction. I'm guessing it must've been a while since someone went down on you, huh? (Scoffs) Their loss.

(Chuckles) Me? A natural? I don't know about that, but... if it means I get to do this for you more often...

Oh, uh... you want to, um, "reciprocate"? O-okay...

(She raises herself up and pulls him in for a long, deep kiss, before pushing him gently down on the couch and unzipping his pants)

Whoa... you really know how to take charge, don't you?

(He starts moaning as she strokes and licks his cock)

Yeah, it feels good... really good... mmmhhh...

Oh, fuck...

Yeah, keep going, just like that...

(He watches as she continues to bob her head up and down on his cock, easily taking most of it into her mouth and down her throat)

Holy shit... you took it all the way down, and you didn't even gag...

Oh, my god... I'm not be able to last much longer if you keep going like that... fuuuuuckk...

(Breathy) You want to ride me? (Grinning) Hell yeah, I want it, too.

Wait, let's get this dress off you, first. It's only getting in the way.

(He helps her slip off her dress, leaving her completely naked. She leans back down and kisses him while she positions his cock between her thighs)

(Breathing, whispering in her ear, admiring her naked body) I swear to god, you are the single sexiest woman I've ever laid eyes on...

(Moaning as she straddles him, and he begins to penetrate her)

Oh, fuck... Fuck, you feel so good. You're wrapping around me so tight...

(Moaning continues, as they fuck right there on the couch)

God, this feels amazing...

I always imagined how good it might feel, but... fuck... this is even better than I'd hoped...

Feels so fucking good...

Yes, yes, yes... fuck!

(Breathy) Are you close? Yeah, I'm getting close, too... Come on... let's cum together... Yeah... that's it... Oh fuck! Oh fuck!

(She rides him harder and faster, until they finally reach their climaxes together, and she collapses on top of him, with both of them completely spent)

Fuck... please tell me we can do that again sometime...

(Surprised) You... want me to stay the night?

(Relieved) Yeah... I'd love to. For a moment there, I was worried that you were just using me as a rebound.

I'm serious. I meant what I said earlier. I'm into you. I want this to be more than just some fling... if you want it, too, that is.

Sure, we can take it slow. See where things go from here. (Grinning) If you ask me, I think we're off to a pretty good start. Come here, babe...

(Fade out to more slow, passionate kissing)