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thecapricunt1616 · 5 months ago

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Very First Time (c.b. one-shot)

𝓢𝓷𝓲𝓹𝓹𝓮𝓽 (𝓶𝓸𝓻𝓮 𝓑𝓣𝓒): “It’s you who wants to kiss me. I told you I’m a better kisser then you, so, if you don’t believe me why don’t you come find out.” He mused and went right back to reading. You sat there for a few moments, dumbfounded. You had a crush on Carmy, but it was only founded when you weren’t together - well, that was a lie, you still thought about kissing him while you were with him but would scold yourself for it that it was weird because he’s your best friend and it’s wrong to think of him that way.

♡ Chapter Inspo: So High School - Taylor Swift ; "You know what you wanted & boy you got her" ♡ Summary: Based on ✩This✩ big brained ask from @carmenberzattosgf ♡ W/C: 9.4K ♡ Posted Date: 06/11/2024 ♡ A/N: Omg I had so much fucking fun writing this you have no idea!!! I hope this satisfies your virgin carmy tooth my dirty olive martini! Also, New look for this one shot how are we feeling yall? ♡ Warnings for BTC: SMUT SMUT SMUT, Characters are 18+, High school relationship, childhood best friend trope, virgin!carmy, Fem!/AFAB!Reader, R has long hair, No use of Y/N (r goes by childhood nickname 'squish'

♡ 𝐌𝐲 𝐋𝐢𝐧𝐤𝐬 ♡ ➵ 𝐂𝐡𝐞𝐜𝐤 𝐨𝐮𝐭 𝐦𝐲 𝐌𝐚𝐬𝐭𝐞𝐫𝐩𝐨𝐬𝐭 ♡ ➵ 𝐂𝐚𝐩𝐫𝐢𝐂𝐚𝐫𝐦𝐲 𝐨𝐧𝐞-𝐬𝐡𝐨𝐭 𝐥𝐚𝐧𝐝𝐢𝐧𝐠 𝐩𝐚𝐠𝐞 ♡ ➵ 𝘊𝘭𝘪𝘤𝘬 𝘮𝘦 𝘵𝘰 𝘳𝘦𝘲𝘶𝘦𝘴𝘵 𝘴𝘰𝘮𝘦𝘵𝘩𝘪𝘯𝘨 / 𝘤𝘩𝘢𝘵 ♡ ➵ 𝐏𝐫𝐨𝐦𝐩𝐭 𝐥𝐢𝐬𝐭 𝐟𝐨𝐫 𝐫𝐞𝐪𝐮𝐞𝐬𝐭𝐬 ♡

2010

You had thought about this year at least monthly since … well - kindergarten. This was your year.

Graduation year.

4 decent years of high school were coming to a close. You were freshly 18 as of last week, and felt exactly the same. You actually felt worse now that your birthday had passed you by. Why? Oh. Virginity. Still having one, that thing.

As far as you knew, all of your friends had lost theirs by now, well - you weren’t so sure. You’d think asking your longest time friend if they were also holding onto their precious dire to get rid of virginity cards as well would be easy, right?

Wrong. Very wrong.

This was because your bestest longest term friend? You’d been concealing a massive crush on him since sophomore year. Well, actually - technically 7th grade, when he saved your volcano from prematurely erupting by pouring borax in the hole from his project about borax crystallization after the nastiest girl in the grade dumped the cup of vinegar in it while you weren’t looking so it would explode prematurely while the teacher wasn’t watching and you’d get zero credit.

But, you told yourself that he was just a really nice person like his sister who had babysat you a few times, so he’d probably heard about you from her and was simply being friendly. Nevertheless, the interaction made you fast friends.

What sealed the deal to you being so close, though, was when a few days later one of the mean boys in the grade tried to make Carmy his newest victim by continually throwing pencils at the back of his head. He did this every class to someone new, and always while the teacher wasn’t looking.

You had waited just until half a second before the pencil flew and “Mrs.Harrison!” urgently left your lips, she quickly looked up, just in time to see the moron let the pencil go, it hit the back of Carmys head, and for Carmy send him a silent glare.

“Jared! That’s a week of detention. It has been you with those pencils. I’m calling home too- this disruptive behavior is unacceptable!” She was so focused on writing out detention slips that she didn’t even remember you had grabbed her attention. Carmy gave you one of his shy close-mouthed smiles that made his adorable dimples show before going back to drawing some pair of cargo jean looking things on the inside of his notebook cover.

This sealed your friendship because you had shown him your loyalty. You have my back, I have yours was always the mentality between you two. By the time you got to high school, you and Carmy were attached at the hip. In middle school, specifically in eighth grade, people would tease you two that you were dating.

The both of you were late bloomers and hadn’t even thought about Carmy or anyone in that way yet, but by sophomore year of high school the teasing really hit home because you did have a crush on him but thought you were absolutely sure he could never like you back, that he saw you as a sister.

Until one fateful June afternoon.

You were laid on your full sized bed together in your childhood bedroom, flicking through a J-14 magazine to get all the latest gossip on the celebrities you follow when you settle on the Ask Sabrina page, a forum where a girl answers dating and love questions.

Dear Sabrina,

I was wondering - what age should you have your first kiss, French kiss, lose your virginity etc? I’m already 16 and I haven’t had sex yet, I had my first kiss at 14 and my first French kiss this year. But I feel like such a loser cause all my friends are having sex, and say it’s so much fun!! Is it really worth the hype?

Jane from California

You roll your eyes. 16 and already had her first French kiss. She was 2 years ahead of you in that sense. You hadn’t had sex yet, either. You hadn’t really kissed a boy for real either. The only kiss you’d had to date was -

Ew!

You had to rectify this situation immediately. The only kiss you’d had to date was Billy Guerrero? In fifth grade?! You couldn’t believe yourself. You’d let time slip away, you’d let your real first kiss prime time slip away. What guy is gonna want a girl at college who was gonna want to date a girl who can’t even kiss properly! You’d bet Carmy had kissed girls, hell he’d probably had sex already. With who you weren’t sure because the only person Carmy opened his mouth to give more then a muttered yes or no were you, and his direct family.

Maybe it was with Claire down the street, she always seemed to you to be sweet on him. He would probably be better for him, anyway. If Mikey wasn’t teasing him about her being his girlfriend, he was teasing about you being his girlfriend. Each time he brought it up Carmy would go red as a tomato and tell him to shut up, and if Richie was around it would get even worse.

You wondered if he liked it, why he didn’t tell you about it - wait - why hadn’t the two of you talked about sex? It wasn’t until this moment you’d realized you’d never breached the topic. You laid your magazine on your chest, flicking the cover of Carmys Spider-Man comic with your nail to get his attention from your position sprawled out over his thighs as your pillow.

“Mm” he hums in response, blue eyes continuing to move across the page. That was something you always loved about Carmy, those large round blue eyes. You loved to tease him that he looked like Flik from bugs life. You’d done very intense studying of those eyes from your many intense staring contests over the summer breaks you two spent together, he would cheat to win, of course - but you liked having an excuse to look at his eyes, so you didn’t mind.

“What was your first kiss like?” You test the waters. Without even realizing what you had done, he mirrored you and laid his open comic on his chest to hold his page so he could give you his full attention.

“First kiss?” He repeats. You couldn’t believe how much better his stutter had gotten over last summer. He had told you he wanted it gone or at least as gone as he could get it by the time you went off to college, so the two of you checked out all the speech pathology books the library had to offer and got to work every day. It was hard work, but after about a month he got the hang of it.

“Very first kiss, well - real kiss” you clarify and by nature he brushed away your bangs that had fallen in front of your eyes from the woosh of air that came from putting his comic down.

“Uh- w-wh-“ he stops himself, closing his eyes and taking a deep breath, focusing really hard on what he was trying to say and a few seconds later he tries again “what’s a real kiss? Like a kiss that’s not just the back of my hand?” He joked and you snorted a chuckle, rolling your eyes playfully.

“Yes dummy like- like a real kiss on a date or something or like…I dunno have you ever had a girlfriend? Well, before you met me? Would a 6th grade girlfriend count?” You thought out loud. You hadn’t ever had a boyfriend before, and Carmy hadn’t said he was dating anyone and spent all of his time with you that wasn’t spent at home or at school, so you could safely assume he hadn’t, but just wanted to be sure.

“n-no- no girlfriend uh- why do you ask?” He cleared his throat that way Richie did after he asked a question he knew was stupid and you shrugged a bit

“So who have you kissed? Claire?” You ask and those big blue eyes go wide as saucers as he shakes his head no like a bobble head

“What - what?! W-why why would you think I kissed Claire? Claire- Claire Dunlap? from down the street?” He clarified, his cheeks heating up

“Woah! Do you have a crush on her?” You sat up and he groaned, rubbing over his face dramatically.

“Squiiish. Not you too” he groaned dramatically. “No! I don’t like Claire! Actually to be f-fucking honest everyone always trying to cram her down my throat makes me hate her!” He huffed

“Well then who have you kissed! A real kiss!?” You question with a laugh, unsure why he was being so secretive over something so small. The two of you could vote in the next election for Christ sake, a kiss shouldn’t be this big of a deal.

“No one!” He blurts, the heat from his cheeks bleeding up to the tips of his ears and down his neck and collarbones. “There. Ok! No one and I sure as fuck didn’t kiss Claire Dunlap.” He crossed his arms, averting your gaze. You were sat there, just staring. You were frankly trying to absorb that, it was surprising to you with such a stud of an older brother - he hadn’t gotten around.

“Me either” you said after a few beats of silence and his eyes quickly found yours again, mouth dropping slightly and he blinked a few times, the way that told you he was trying to digest what you were saying.

“Y-you haven’t kissed Claire-“

“Anyone” you interrupted. His jaw dropped like a trout as he stared at you in shock and you grabbed your magazine, rolling it up and bonking him on the head with it. “Don’t look at me like that! You haven’t kissed anyone either! I technically have you beat because I kissed Billy G. at recess in fifth grade once even though it was just like… a mom kiss you know like a- like” you demonstrate a little puckery peck of your lips.

His eyes narrowed with jealousy and you smiled proudly “Squish, one - Bear? Zero” that was one thing about you two, you were always in a competition of some kind. Who could run farther, who could read a book faster, who could get their homework done first, you never realized it translated into other things too, and that neither of you were in the lead.

“I bet I’m better then you at kissing even though I haven’t done it I’ve practiced more so I’m good when it’s time for me to show my skill” he smirked, picking up his comic again. You scoffed

“Practice? On what, your bathroom mirror? It doesn’t count if it’s not a person, dummy.” You said and he shrugged

“Find out” he said casually, eyes not tearing up from the page. Now it was your cheeks that felt like they were on fire. Find out?! Find out what, does he even realize what he’s offering you right now?!

“Find out? What- you want to kiss me?” You said and he smirked a bit, dimples showing and his eyes flick back to yours.

“It’s you who wants to kiss me. I told you I’m a better kisser then you, so, if you don’t believe me why don’t you come find out.” He mused and went right back to reading. You sat there for a few moments, dumbfounded. You had a crush on Carmy, but it was only founded when you weren’t together - well, that was a lie, you still thought about kissing him while you were with him but would scold yourself for it that it was weird because he’s your best friend and it’s wrong to think of him that way.

But now he was just offering like it was his apple he didn’t want at lunch.

“French or regular?” You ask, trying to play it cool and the astonished look on his face led you to cackle, shoving his shoulder “what?! Stop looking at me like that weirdo!” You said and he smiled, shaking his head and doing one of those slow Carmy blinks as he sighs, a little smirk on his lips. He always reminded you of Natalie when he did that, he must have gotten it from her.

“You want me to stick my tongue in your mouth?” He mused and you nod

“I actually think it goes both ways- and with 0 practice I’d win. Sure of it.” You said cockily and shrugged a bit. He snorts a chuckle

“And how do we determine a winner?” He asked, shutting his comic and resting it on the nightstand next to your bed like he was genuinely weighing the offer in his mind.

You were quiet for a few moments, looking at him carefully - and it seemed like he was serious as you were, so you said “It’s supposed to feel good, right? So…whoever like..moans first?”

“Uh o-okay- okay sure um.” He swallowed thickly, wiping his hands on his jeans that you assumed were clammy now how they got when he was nervous. “So- how- how do you wanna like- sit,” he asked. Fuck. You were just now realizing you weren’t actually sure. Your heart was thumping so hard in your chest, blood was roaring in your ears. This was all going so fast - you were going to do it. You were going to kiss your crush.

“Uh-“ you said stupidly, tucking your hair behind your ears and digging your chapstick out of your pocket, cause guys like soft cherry flavored lips, right? If he was kissing you for a stupid competition you may as well make it good. “Yeah um. I think, maybe criss cross? Right? Like how we would play sailer by the sea” you crossed your legs and sat in front of him

“We should play later I’ve been practicing with nat - I’m totally gonna beat you” he crossed his legs, and you moved in closer so your knees were touching but your faces were still about 2 feet apart, too big a distance for a kiss. “Also- we’re gonna need to be closer” he said plainly. You snorted a laugh,

“Yes - we can play. How am I supposed to get closer?” You asked, and in one fluid motion he stuck his hands under your calves, and uncrossed your legs before dragging you forward quickly and wrapping your legs around his waist. You could feel his breath.

“There” he looks at you, eyes fanning from your eyes to your lips and back again. “That’s ok, right?” The low softness of his voice, mixed with the action of him just taking control how he did - it sent this feeling down to your core that felt so good. Like a pleasureful pulsing heartbeat, the only time you got that feeling was when you were alone in bed at night squeezing your thighs together thinking about Carmy.

“Mmhmm” you hummed, unsure what to do with your hands so you settled for placing them on your thighs. “So- uh- ok. I guess um..let’s get started?” Your voice was small, nervous. A definite switch of roles for the two of you. You weren’t sure if this was normal, but you assumed it was for Carmy.

He was being so normal about it, the same normal he was when you got your period at his house - he just went to Natalie’s bathroom, and came back to the guest bathroom with a few pads and tampons for you, as well as feminine wipes - normal. Not weird, like this happens every day for him. Like - periods (or in this case) sex isn’t the most embarrassing thing to teen life. His chill demeanor told you that he strictly saw it as a platonic friendly competition, so why do your panties feel sticky all the sudden?

“It’s ok- we don’t have to-“ he’s interrupted by your lips on his,

Now or never, right?

It was warm, a little messy at first, you found out quickly you should close your eyes since he closed his and once you did it was much easier to just focus on the sensation. His lips were soft, he tasted like the bowl of trix cereal he must have had before he came over. The way his lips moved with yours was… gentle, sweet, unhurried- you found yourself chasing them when he pulled away slightly and that caused you to open your eyes

“You-“ he huffs a small chuckle “you have t’kiss back, Squish. S’like i’m kissing a wall here” he said. You took a shaky breath, not even realizing you were just sat there like a dead fish, unmoving, in awe that his lips were really on yours. If you hadn’t just finished your period a week ago you’d be scrambling to the bathroom to see what was going on because you were gushing.

“Uh- sorry- sorry. I was just warming up” you clear your throat awkwardly, fingers tapping on your thighs nervously “lets try again” you said, leaning in and additionally mashing your nose with his “ow- oh- gosh, sorry” you giggle and he followed suit

“S’not your fault my beak is getting in the way” he joked, gently tilting your face and bringing his lips back to yours. You got the message this time, moving your lips with his and wow. It felt…good. That heartbeat right above your cunt had never pulsed so hard before, it nearly hurt and you weren’t sure what to do about it with him right there.

You’d usually use the firm corner of one of your throw pillows you kept on your bed when this uncomfortable sensation happened, thinking of exactly this - kissing Carmy - and hump it, and hump it, and hump it, until you were frustrated to tears because you still felt like you weren’t finished. That the feeling would never go away unless you stopped thinking about Carmy like that - but it was addictive, and you couldn’t help but think you were chasing something.

It all elevated when you felt his tongue on your bottom lip, it was almost like the sensation in your core was beginning to travel throughout your entire body and that had never happened before. It went from just that strong pulsing in your cunt, travelling to a tightness that was winding up in your stomach, your breasts felt good - as strange as that thought was, the only time you remembered they were there was when they were sore because your period was coming, so the warm gushy feeling in your chest and the pangs of pleasure that were coursing through you from the simple swipe of his tongue was something to be revered.

From there, it was like you were following a script you hadn’t even known you’d memorized. Your hands found his shoulders, before travelling to the back of his neck and rubbing over the little curls at the base. You swipe your tongue over his, fingers sprawling over the back of his head to pull him in closer. You didn’t know what came over you, but you deepened the kiss, and he accepted. His hands found the back of your waist, squeezing gently and trailing up your sides, stopping hard below your breasts.

You pulled away, looking at him. If it was any other day, he’d have thought you were initiating a staring contest, but the blown-out look in your eyes and small pants leaving your lips reminded him of when their family cat had a little too much catnip and started climbing the screen doors, wild. His eyes nearly fell out of his head when the next question left your lips

“Have you had sex before?” your voice was breathy, if you had known better you’d have called it for what it was - horny. The only thing on your mind was Carmy, not how your mom would be home any minute and you forgot to take out the chicken for dinner, not how it probably isn’t a normal thing for best friends or any friends really, to kiss. But you and Carmy hadn’t really ever been ��normal’ friends.

“Uhhh” he tried to find his words. He looked so pretty. His cheeks were the pretty flush pink you loved on him so much, it suited him. His lips were swollen and kiss bitten and red. You realized that the glossiness on them was a mixture of your salivas and that brought a burst of that delicious warmth to your chest. “N-no, haven’t have you- I mean- can you have sex without kissing?” he wondered out loud.

“I don’t want to leave high school a virgin” you blurt out. It was half true, you did feel a bit like a loser, even though you could always lie and tell people you had done it even if you hadn’t. It also felt like the one opportunity was presenting itself for you to have sex with your childhood crush and if he agreed, then a win is a win in your book.

“Alright and- and uh” he sits back on the headboard, huffing a chuckle and rubbing over his mouth as he thought, staring up at the ceiling to try and get a gauge on what he was about to say. It was one of the habits he’d picked up during all of your speech practice together, it was cute, almost like he was stopping the words from falling out of his mouth before he was ready to say them so it didn’t come out all jumbly and stuttered. “And you wan’t help with this- i’m assuming you see it as a problem? Thats why you brought it up, right? You want help with that…issue” he mused.

Suddenly, you felt really, really shy. Shy, stupid, flustered, any synonym for embarrassed and feeling like a complete and utter moron. “I shouldn’t have said anything - i’m sorry, uh- you win” You got up, going over to your dresser and digging out your after-school clothes to change since you were in jeans still. Why the hell would you say that? What, was he gonna just offer to have sex with y-

“I-I mean- I don’t want to, either. I just uh- haven’t… y’know - met anyone who I trusted enough to do it with. But- it- it felt good… the kiss? So, if you wanted we could um..cause- cause I trust you, I trust you more then like…anyone- so, yeah- I-I mean it’s like- like a favor right? You uh…scratch my back- er whatever the saying is- if- if you want to” you looked back at him to see him rambling with his gaze locked on the floor, clearly feeling as stupid and embarrassed as you feel.

Holy shit, this may actually happen.

“Yeah- yeah” you agree, mulling it over in your mind. He’s right, this shouldn’t change your friendship, because from what you’d heard - losing said virginity wasnt fun, it was weird, uncomfortable, and a little gross sometimes, so it was almost like you two could get the awkward first time part out of the way together so you could both hit the ground running in terms of dating and hooking up when it came to college, cause that's what college was supposed to be all about, right? Finding the love of your life?

“Sure- Uh-” you swallow thickly and toss him one of the many pairs of sweatpants he kept in your dresser for when he slept over as well as a fresh t-shirt and grab yourself a clean pair of panties from your top drawer since although the awkwardness had taken away that dull needy ache, you were still uncomfortably wet and had to get yourself cleaned up and changed. “How about Friday? My parents have their date night so- you could come over after school and we can um…do it?” you ask and he nodded quickly, grabbing the sweatpants and sweatshirt.

“Yeah- perfect, that’s - mmhmm” he swallowed hard, cheeks bright red. You would totally be making fun of him right now if you weren’t absolutely sure you looked just as flustered, the two of you sharing at eachother in silence like a pair of deer in headlights.

“I’m gonna go change” you said and left the room, closing the bathroom door behind you and sighing deeply to yourself, leaning against the door.

And so it was set.

Carmy had exactly 3 days to study up on this topic other than sophomore health class he knew absolutely nothing about. Well- he had found one of Michaels Playboy magazines before when he was 14, it was the first time he popped a boner and it freaked him out so bad since his father wasn’t very present and Mike hadn’t given him the talk yet. It was a solid 2 months of worrying that he had some weird dick cancer because he got hard every time he peeked through said porn-mag before he asked Mike about it, and he still hasn’t lived down the teasing. Thank god Mike kept his word on not telling Richie.

The moment he left your house that day it was straight to the Chicago public library. 3 books, 3 days. He was going to do his homework on this, because he was going to win the game he knew was inevitably pun intended coming his way. It was going to become a competition, and he knew the name of the game in sex was an orgasm, he knew that much at least, thank god.

The 3 titles he’d settled on,

Sex For Dummies ; He’d figured that should speak for itself, it sounded to him like the beginners guide to fucking. He wondered why every teen didn’t get a copy of this book, he’d heard guys talking about how sometimes girls are really bad in bed - so if everyone got one, like the dictionaries they all got in elementary school - he thought their lives would probably be made easier in that department.

She Comes First; and boy, was that a read. He stayed up so late Wednesday night reading it that you had to wake him in homeroom when the bell rang to go to first period. He didn’t know there were so many things to know about a vagina, but he was confident now he probably knew more then any guy in the school about pussys and what gets them going at least on paper once he read all 350 pages in one day.

He comes next; It made alot of sense. This was the breaziest read for him, he sat on the L after school reading it on the ride home. Of course, the front was covered in a brown paper bag he’d taped to it so no one could tell what he was reading, he wasn't a pervert! He was glad he read she comes first, first, because he’d learned that girls can cum more then once, and that when they do - it gets better each time. He also learned that the clit is the best part to touch, and that it actually has like- a tail? Or something? Inside that you can mess with too, and it feels super good for the girl. He wasn’t sure how he was supposed to find something like that with his dick, but he guessed he’d figure it out.

The day was finally here. You had been thinking about it all week long. The prep you were doing was very different then the prep he was. You were making sure your entire body was smooth, plucking your eyebrows, waxing your upper lip, whitening your teeth, shaving your big toe. Literally, anything and everything grooming. You had put on a lacy pink thong that you’d gotten at the mall a year or so ago in preparation for the night you finally did this, but after observing yourself in the mirror you felt insecure about it. It was just Carmy, he wasn’t into you, it would be weird if you tried to be sexy, right? Like you were trying to seduce him or something? So you settled on some plain grey panties, instead, and a black bra.

You heard a knock at the door right at 7. Exactly on time, per usual. Your parents had left for their date 20 minutes ago, so it was perfect timing. When you opened the door, you heart may as well have melted and poured out of your ass to see Carmy standing there with a bundle of red roses. “Hey- uh- so - got you these” he thrust them in your direction. They were already cut, and thornless, ready to be plopped in a vase. You could see a little bandage on the pinky finger of his non-dominant hand that wasn’t there at school today, he must have pricked himself while he was trimming them up.

“Y’get a girl flowers, you trim em’ up, n’for the roses gotta take the thorns off, eh’? Don’t wan’t t’hurt ylady do you? And you trim ‘em cause girls like it, makes em’ all even n’shit. N’it Makes em’ live longer too. Y’givin a gift not a chore heard? Flowers need to be able to be dropped in a vase and that's it, otherwise y’re a prick f’givin’ y’r lady a job t’do” Mikey explained as he snipped the thorns off of the roses he’d gotten for his date. The conversation stuck with Carmy all these years, he promised himself one day he’d put the advice to use.

“Oh- wow - Bear, these are like -” you leaned in, smelling them deeply, the sweet floral sense filling your nose “Wow- this is so sweet of you, you didn’t have to” you stepped back and opened the door wider. He followed you in, shutting the door behind him like usual.

“Mikey says it’s what y’do I guess, so - expect flowers from guys you do this with” he nudged you with his shoulder playfully. The action made your heart flutter but also stomach sink , heavy with nerves. Right. He’s here to just get something over with, like he was probably expecting you to be and the flowers were just a result of him wanting to do things right and not because he had any real, tangible feelings for you other than platonic.

“Mmm, will do. Thanks- I’m gonna go get these in some water, you can get settled” you told him and headed into the kitchen to find a vase. When you came back to the room his hoodie was neatly folded and sitting on your desk, his shoes tucked away beneath it and there was a… towel? On your bed?

“Uh-” you set the vase of flowers on your dresser

“Right- uh- so the towel, they say in the books for your first time, sometimes girls will bleed a little? Or- or if I do it right things can get really wet, so…just trying to be proactive I didn’t wanna make a huge mess y’know?” he explained while staring at the towel and rubbing the back of his neck nervously how he did, heat creeping across the bridge of his nose and onto his cheeks.

“You…studied?” you smile a bit at the idea. You wondered how he did so, did he just watch porn?! You had heard from girls with boyfriends that watch porn - the sex was usually bad, and that they went way to hard and fast. You hoped it wasn’t that.

“Yeah I read some stuff.. How else will I know what the fuck m’doin?” he watched you as you sat down on top of the towel, assuming that was the spot he meant for you.

“Uh- yea…yeah. Ok, well thanks- I guess I should have studied, too. Didn’t even think about it- my legs are soft, though. And I shaved my - um- yeah.” you said, voice getting meeker and smaller by the end. The two of you were never like this, it was usually constant banter and comfortable silence. Awkwardness wasnt something the two of you experienced together up until now.

“Thank you- you didn’t have to it’s…it’s just hair. But um…go pee, before we get started- you should pee.” he sat down on the bed in front of you. You looked at him confused, brows furrowing together but before you could ask he added “In the books, they said for girls - it can feel like…like you need to pee, right before the good part if I do it right. So, if I do do it right- I want you to be able to finish instead of worrying if you’ll pee on me, so I figured if you go pee now then-” you held your hand up, shaking your head as you stood.

“No further info needed” you said as you padded off to the bathroom. Even though the shower you had taken not even an hour prior to him coming over was so thorough made you fresh as the day you were born you still wiped up with babywipes before coming back to see 2 granola bars and 2 bottles of water on the nightstand. “Are you planning on making me pass out or something?” you joked, sitting back on the towel like before.

He chuckled a bit “Well if i’m that good my first time it’ll be a record or something I bet” he rubbed his forearm nervously “So um..should we kiss? Like last time?” he asked, averting your gaze. You didn’t know this, but he thought he was genuinely about to have a heart attack, and the only reason he was continuing instead of asking you to call an ambulance was because if he was to die in your bed while making out because of the sheer excitement that came with the potential of you touching his dick, he would have died happy.

The question being asked in that soft, sweet tone of his- syrupy and honest, made your stomach flip- and there was a pang of warmth to your heat that made your heart jump to your throat with anticipation. You couldn’t answer, instead, you just nodded, not breaking his gaze. Jesus fucking Christ those eyes. You had only seen the ocean once, in Hawaii on a vacation. His eyes made you think of the waters in Maui, that was how blue. You could get lost in them like they were the ocean, they often rendered you speechless, like he could peer into your soul. “Okay” he said gently.

This time, the kisses started small. He gently pecked the corner of your lips, before you remembered that yes you had a job to do here as well, and you put your hand gently on the side of his cheek, barely touching him. He could feel you shaking, so he put his hand over yours, gently squeezing your four fingers as his lips captured yours in a tender, affectionate kiss. The feeling was so…different then last time. This time felt much more purposeful, and not in the get it over with way, in the i’ve been meaning to do this, way.

Honestly, the feeling made you dizzy. Not dizzy in the kind of way that immediately made you want to throw up, -

(Carmy learned you got very motion sick very quick at your 15th birthday party when he, Mike, Natalie, and Richie were teaching you how to play dead-man on the trampoline and within 10 seconds of being bounced with your eyes closed by the 4 of them you were scrambling to throw up a mix of cake and pasta)

- but dizzy in the way that you weren't forming any kind of memory of the encounter, and you also weren’t sure what you were doing - but you came to with your shirt off, dry humping your best friend as he laid sprawled over your floral duvet panting into each others mouths as your childhood teddybear watched the two of you manhandle eachother, he honestly looked like he was judging, but you mentally told him to fuck off.

“Yeah-” he breathed, his cheeks were a pretty pink, his pupils “I-I think that was um…better then last time. Do you feel hot? I feel hot” he admitted, swallowing hard as you both caught your breath. You looked down and oh, yeah - he's still fully dressed. You were still mostly dressed, too. Well, your shirt - you hadn’t a clue where it went, but your fluffy pajama pants were still suffocating your thighs and holy shit..

He is hard as a rock against your clothed pussy right now.

You look back up at him, and nod in agreement. “Feels like - wow- yeah. Uh- m’hot” you got up and saw the evidence of his arousal straining against his jeans. “Uh- so…” you trail off

“I think i’m supposed to do that part” he sat up, taking his shirt off in that silly boyish way with one fluid motion pulling it up over the back of his head, his sandy blonde hair becoming ruffled by the action. You look over his chest, not even bothering to not stare. That was the point of this whole thing right, to experience? In turn, he crossed his arms shyly, to be expected. Carmy had been open about his upset that he got more of his moms genes then his dads. He was short, softer-jawed, smaller-lipped, and bigger-eyed, the only thing he got was the big Italian Berzatto nose.

His brother was tall, much broader, was able to grow a full face of stubble by 17. Carmy was still patchy, but he was proud of his little patch of curly brown hair in the middle of his chest. Mike kept telling him he would ‘grow like a weed’ as soon as he turned 20, he didn’t believe it, though.

“Oh- yea? Thats what they said in your sex books” you teased and stepped forward, between his spread thighs, likely to give his dick breathing room. His hands found your hips as he snorted a chuckle

“Shut up” he smiled and carefully pulled down the waistband of your pajama bottoms. “I did read…” he helped you step out of them, hands trailing up the backs of your now bare thighs. The action made goosebumps appear on your flesh, nearly made you shiver. “That you are supposed to cum first, it’s like…a warm up.” he explained, looking up at you as he made his way to hold your hips again. You realized quickly, that his hands were also trembling, and he kept stroking and petting you hoping you wouldn’t notice as much.

Your panties had a dark spot on them that he became fixated on momentarily, his tongue darting out to lick his lips. You felt that twitching at his words, your hole clenching around absolutely nothing. You weren’t sure you could remember what color the sky was if someone asked at that moment, you were so focused on Carmy, it was like you two and this bedroom were the only things in the universe. “I haven’t been able to do it, I don’t think you’ll be able to - but you can try. How do you want to do this should I just lay down and I dunno… you stick it in? I got 3 boxes of condoms, different kinds just in case” you went to open your nightstand and he stopped you, grabbing your hand.

He chuckled a bit, you took it as a you don’t know what you’re doing, let me explain kind of laugh, but really he was just wondering how the following words came out of his mouth “I’m supposed to eat your pussy, could I try?”

You swore your knees went weak. Carmen, Carmen Berzatto wanted to go down on you. Thank god you made sure that department was taken care of so well in preparation. “Uhhh- alright” you sat down on the towel, twiddling your fingers nervously “So- wow uh” you giggle nervously, covering your mouth with your hand.

“Your um..you look pretty, by the way” he said while looking at the duvet. He sounded as nervous as he was when he said that. He had thought you looked pretty from the moment he walked through the door, but was too nervous until you were both literally almost naked to say it. You could hardly believe it, because you did your best to not put in a ton of effort. Sure, you were very well groomed, but you didnt like - dress up or put makeup on or do your hair how you would have wanted, you were in regular bra and panties, and pajamas when he walked in. You were also pretty sure that you had a zit growing on your chin and really hoped he hadn’t noticed.

But, that was exactly why he thought you looked so pretty. He loved that you let him have you like this, well - in both senses. He felt so lucky to be able to see you comfortable, in your element. “Thanks, dork, so do you get the honors of taking my panties too?” you teased. That was the difference between you, when you got nervous you cracked jokes and made fun of him to ease the tension in your own mind - when he got nervous he often got lost in the tension of his own mind causing him to go quiet.

“I do actually, says the book- so lay down” he shoots back in the same teasing tone, a small smile gracing his lips once again. You, and his brother were the only 2 that could pull him out of his head so fast, and so easily. You shook your head, laying back on the pillows he’d set up and spreading your legs, laying your feet flat on the bed. He sat in front of you, running a hand up your leg and feeling over the soft, smooth skin. “You are really soft” he muttered, almost to himself, feeling up your thigh “Do you mind if I kiss you, here?” he asked gently, running a palm over the inner of your thigh. No one had ever touched you there, so the action made you shiver since the area was surprisingly sensitive.

“Sure” you said quietly, watching his every move with wide, curious eyes. You were sure the wet spot on your panties had grown tremendously due to the way you felt dripping down the curve of your ass, thank god for that towel when they come off or my sheets would probably soak through by the end of this. He started at your ankle, leaving gentle pecks and putting your manicured foot on his shoulder as he continued his journey of kissing up your shin, over your knee, not leaving a single part unkissed. If this is what sex was about, you totally got why all your friends were raving about it, because you were being driven absolutely wild and it hadn’t even really started yet.

He kissed up to your thigh, laying down in between your legs. His forearms were wrapped around the plush of your thighs, hugging them as he left kisses over the waistband of your panties. The action made your stomach muscles clench at how good he was making you feel. You needed something to touch you, though. That was the only thing on your mind, but before you could ask - he beat you to it. “Would you be ok with me kissing your middle here?” his voice was husky, breathy. He was gripping your thighs so his hands wouldn't shake, he was fucking panting like he just ran the mile in P.E. and he wasn’t sure why.

His mouth was watering at the smell of you, he had to fucking swallow a mouthful of spit before he could say something. He felt like a fucking starved animal, but he was gathering every polite, gentlemanly fiber of his being to remain kind, gentle. “Please do” you said and without hesitation, he was essentially making out with your cunt through your panties. The sight was filthy, but so sexy it was making your head spin.

Whines and moans were leaving your throat you weren’t even aware of as you watch him, slack jawed and sucking at the fabric of your panties, grunting and moaning at the flavor. “T-take em off…please-” you weren’t sure where the bedroom voice that came out of you came from, but he seemed to like it at the way his eyes rolled and fluttered shut at the way you were begging for him to eat you out.

He sat up just enough to get your panties pulled off, shoving them in the back pocket of his jeans before laying back down and resuming his position. “Taste so, so good, squish, better than I imagined” he said before kissing your mound. The wet clicking sound of your pussy clenching at his words made heat rush your cheeks in embarrassment, but it made his dick twitch against his jeans. “Can I kiss your clit?” he asked, the casualness of his tone made your head fall back on the pillow, covering your face with embarrassed hands at the vulgarity of it all.

“Go ahead, Bear” you said, smile lacing your voice.

“I liked it when you were lookin’ at me, just so you know” he said, spreading you out with his fingers and looking for just a moment, he found it easily as it had grown nearly twice it’s size, peeking out of its hood. He attached his lips to it, just like the book he’d read said to do, and lightly sucked, before flicking his tongue lightly over it. Your hand clamps over your mouth to stifle the cry that left your throat, hips jerking and you grab his hair with your other hand, not even meaning to but tugging.

This caused a moan to leave his throat, which in turn caused his lips to vibrate, and you looked down at him, vision hazy like a dream at the sensation. “God- oh god- feels so good Bear - wow- you’re so good at this” you said, breath heavy and jaw slack “uh-huh” you whine when he pads his tongue over your clit in wide, wet drags. The sounds his mouth was making as he sucked and kissed and lapped at your juices were absolute sin, the hottest shit you’d ever heard.

“D’you like it more when I kiss your clit like I was doin’ or when I run my tongue on it like that?” he asked, sucking at your folds and nose nudging your clit as he waited for an answer.

“Both - Both- everything feels good - you feel so good” you praised, pushing his bangs from his face. He smiled into you proudly, continuing to lick, and suck, and swirl his tongue. It had been a knot building for a while, and it had been about 30 minutes of him doing this, when you felt it. But, all the activities you’d been engaged in the conversation you had before you started slipped your mind. “Fuck- fuck - sorry- I gotta pee” you told him and tried to tug him off

“Y’dont, trust me, just trust me” he said determined, he had told himself before going into this that if he could make you cum, that it would be his prize because per the books he’d read one of the main complaints with women was that their male partners didn’t bother to be sure they finished, so if you never wanted to do this again - he’d pride himself internally forever on be the very first man to ever make you cum.

You whined, back arching to the ceiling and hips dipping back into the bed. You didn’t want him to stop, so you weren’t sure why you were subconsciously trying to wiggle away. Your eyes had been closed for a few moments, and you felt a hand on your stomach, dancing fingers following it. You opened them to see him looking up at you, and his eyes flicker to his hand that was laying palm up on your belly before meeting your gaze again, in a silent ask for you to hold his hand.

Without thinking, you did so, needing to be grounded in that moment. His thumb rubbed soothing strokes on the back of your hand as he built up the speed of his tongue, running it back and forth and up and down, flicking it, sucking on the sensitive nub until your brain turned to mush, and stars filled your vision.

“Carmy Carmy- Oh shit- Yes”

The grand finale only lasted about a minute or two, but by the end your thighs were shaking and you were gasping for breath. “Y’need to breathe, did you forget humans need oxygen to live?” he teased. You’d usually give him a light punch on the shoulder for that, but your whole body felt like warm jelly.

“Shut up” you pant, looking down when you feel your clit twitching every few moments “I think you broke it its like.. Having a seizure or something” you said and you both burst into giggles. After a few moments of comfortable quiet you nudge him with your foot “Hey” he looks up at you “Its your turn now” you said and his brows raised

“Y-you don’t have t’do that, that was sex, so - congratulations we are both not virgins” he wiped his chin on the inside of his arm and sat up. You furrowed your brow

“No- I want to, I can make you cum, too ” you said, in your mind, it was a challenge - and when it came out of your mouth you realized how it sounded.

“Are you… asking me for permission to suck my dick?” he looked at you carefully. Shyly, you just nod. For whatever reason the nature of the room and this particular situation had the two of you acting out of traditional character roles, and he was the one being bold. “I want you to say it, then you can suck my dick” he said and stood up, unbuttoning his jeans and looking at you, brows raised expectantly as he waited for you to do as he asked.

Your throat suddenly felt dry, and you were starting to drip on that damn towel again. “Bear, I wanna suck your cock, Can I please?” you asked, tone innocent yet laced with a confident determination. His breath got caught in his throat, you swore his eyes could have fallen out. He didn’t know the word cock was apart of your very colorful vocabulary, he could have creamed his boxers with the way that the word rolled off of your tongue.

“Sure” he said all too casual and tugged off his jeans, kicking them to the side. He laid down with you, like how he was while you were making out and you got on your knees tugging the waistband of his boxers until his cock came out and kissed his navel, the tip glistening with pre.

“So-” you look at it, mouth watering at the sight. You had never done this, but you were sure that you knew one thing for sure, Carmy had a really pretty cock. You didn’t even realize you were staring until he said

“S’not gonna suck itself, squish.”

Oh, right, that was what you were doing. You grab it and he hissed “Fuckin’ hell- y’tryna rip it off? A little nicer, please” he chuckled a bit and you felt your cheeks heat, loosening your grip.

“Sorry…” you said sheepishly, bending over and licking the tip of it, one slow drag from the back of your tongue to the tip of it, flicking your tongue over the slit your nose scrunching slightly at the new flavor. The action though, had Carm seeing stars and his toes curling.

“Hhhhnnn- oh my fucking god” he rasped. You figured that was a good thing, so you did it again “Squish I-” and again, “yes- fuck” and again, “Squish i-i’m gonna mmmmmffff” he whined, his cock twitching in your hand and leaking pre in a near continuous drip. You had no expirience, so you had no idea what this meant, or that he was trying to warn you. With 3 more slow sensual ball to tip licks, he was shooting cum all over your nose, upper lip, tongue, and chin. You squeak in surprise, sitting up and licking your lips. “Oh- hmmmmfuck- gimme a sec” he groaned, taking over for you and stroking himself, the remainder of his load shooting over his stomach.

You watched in awe as he got himself off, back lightly arched and head fallen back, eyes closed as sexy pants and moans left his lips, along with soft “fuck - thank you, thank you” It was literally the hottest thing you had ever seen. He stopped after a moment, finding his breath and looking up at you, when he saw your milky white chin it both made his softening dick twitch and drew a chuckle from him. “When I keep saying im gonna do something and my dick is leaking like a broken sink it means open up er get out of the splash zone” he joked and grabbed his shirt, wiping your chin and neck.

You laughed, laying back down and sighing contently. “Noted for next time” you said and he fixed his boxers, sitting up and stroking your calf.

“There can be a next time? I mean…. I was hoping so that was really fun, felt really good” he said and you nod, smiling a bit

“Sure, I mean, yeah… but it doesn’t mean we stop like- doing friend stuff, right?” you questioned. As much fun as you had, you could never give up something as treasured as your friendship for something as trivial as sex.

“Oh, absolutely, who else is gonna wait w’me to get the new spiderman comics? And whos gonna feed you when your parents are out of town?” he teased and you rolled you eyes playfully, smiling and shaking your head.

“Love you, dork” you bit your lip as he brought your other ankle to his lips.

“Love y’too, Squish. Can I?” he looked down at your glistening core, before back at you. You bit your lip lightly, you weren’t sure if all men were this enthusiastic about eating pussy - but you were thankful that he was because your mind was still swimming from the last time and you had to experience it again.

“Mmhmm” you spread your legs wider for him and he took your hand, lacing his fingers with yours as he got to work. You had found quickly that when you tell him something feels good or he’s doing a good job that it really got him going. It was cute, truly, how he loved being praised, so you made sure to do it whenever you could get something out that wasn't a babbled, coherent mess since the pleasure he was providing was causing your brain to short circuit.

An hour and a half and 3 orgasms later, after about 10 minutes of trying to catch your breath and cool down since you were boiling from the blood coursing your system like an F1 racetrack, you sit up. “M’gonna go get cleaned up” you said, going to get up on wobbly legs.

“No! No, I got it lay down don’worry” he said and made his way to the bathroom. He came back with babywipes and a wet wash cloth, as well as a dry clean towel to wipe off with after. He helped you wipe up and knowing your bedroom by heart, he went over to your dresser and got you a fresh set of panties and a tshirt, as well as a pair of his sweatpants so you could both be comfortable. After you had both gotten dressed, he laid in your bed after bringing the towel downstairs to the wash for you both as well as your dirty clothes, and you cuddled into his chest as you turned on your little tv, playing the next episode of Glee and he hands you a granola bar after being sure you had a few sips of water to replenish.

“To no longer being virgins, hm?” he smiled a bit, holding his bar up in a silly idea of a toast. You tap yours to his with a grin

“To no longer being virgins”

Part 2 here

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malanasims · 1 year ago

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Taylor Swift Eras themed Legacy Challenge

i wanted to put together two of my favorite things: the sims and Taylor Swift. so i came up with this 10 generation legacy challenge in which each generation is inspired by a different album. I created this challenge for the sims 2 ultimate collection since that is the game i normally play, but i am sure it can be adapted for sims 3 or sims 4. i also implemented the traits project for ts2 but you can easily do the challenge without it using different personality points. i set up this challenge so that each generation alternates genders but you can switch that up. i also chose first names for each generation based on references of the album. also some of the writing is very cheesy and has a lot of references because why not go crazy. this is my first legacy challenge so if you have any critiques let me know. the rules are not strict and cheats can be used as its a story-based challenge.

Debut- Gen 1: Mary

“Take me home where we met so many years before.

We'll rock our babies on that very front porch: After all this time, you and I”

You grew up in a small town where everyone knew each other. Your parents never had the greatest relationship and your mom was always with her best friend. Since birth you and her kid have been inseparable. Will you fall into the same patterns as your parents…or will you find a place in this world?

family/romance

LTW: reach golden anniversary

nurturing, jealous, loves the outdoors, great kisser, family oriented

marry your first love

have 2 children (at least one son)

formal wear is a little black dress

Fearless- Gen 2: Stephen

“You played in bars, you play guitar

I'm invisible and everyone knows who you are”

Your parents raised you well but something about the fact that they only ever knew each other scares you. You want to get out there and make a name for yourself. You know no ones coming for you on their white horse. You’ll have to be fearless to become a superstar: but for now all you have is your mothers eyes and her old guitar.

fortune/pleasure

virtuoso, charismatic, irresistible, ambitious, non-committal

LTW: become rock god

go on at least 5 first dates

have at least one daughter

date a fan

Speak now- Gen 3: Emma

“When Emma falls apart, it's when she's alone

She takes on the pain and bears it on her own”

You often felt overlooked by your rockstar father. He was always busy and you spent most of your time with your mother until her mysterious disappearance. You feel like you grew up too fast, and now you love to travel back to your youth and fantasize about castles and dragons. So you become an actress; a character. Will you break out of your fathers famously destructive patterns, or will you regain your balance on the tightrope and break out before fire can catch you?

popularity/romance

LTW: Become Icon

natural born performer, childish, bookworm, shy, hopeless romantic

your first love doesn't work out/ you break their heart

have at least one son

have a strained relationship with your father but a good relationship with your mother

meet your true love at a party and then never see eachother again

Red- Gen 4: Bobby

“How you took the money and your dignity, and got the hell out

They say you bought a bunch of land somewhere

Chose the rose garden over Madison Square”

You grew up in the starlight of your mothers fame. You two were always close but after suffering from the tabloids and the camera flashes you decide this life is not for you. You move out of the Angel City and start anew. Your mother has given you some funds and you build up a family home. You tell everyone you left because the city wasn’t right for you… but maybe it was partly to run from your playboy/girl ex who you know was trouble. Now you spend your life painting and searching for your muse. Will you stay paralyzed by time or finally begin again?

Knowledge/family

LTW: become visionary

artistic, eco friendly, night owl, loves the cold, loner

Have an on and off toxic relationship

Move out of your parents house

Settle down with someone nice

Have 3 children (at least one girl)

1989- Gen 5: Love

“You searched the world for somethin' else

To make you feel like what we had

And in the end, in Wonderland, we both went mad”

You grew up secluded from the world, surrounded by your mothers paintings. Your mom loved the environment but you couldn’t wait to get out of the woods and explore new places. Somewhere along the road, you fell into a rabbit hole of insanity: mascara running in the bathroom and rose gardens filled with thorns. You blow money and string lovers along. You have fantastic delusions until your wildest dreams turn into nightmares. Will you accept the help from your family and abandon your affinity for screaming, crying and perfect storms? Or will every day continue to be a battle?

knowledge/pleasure

LTW: Become space pirate

Insane, unstable, diva, adventurous, jealous

Join the adventurer career

Have 3 loves at once

Have children with multiple people (one must be boy/girl twins)

Lose money in poker

Reputation- Gen 6: Burton (the name is so bad help)

“I don't like your kingdom keys

They once belonged to me

You asked me for a place to sleep

Locked me out and threw a feast”

Yeah, your mother may have done a number on you, but who's counting? Maybe your twin sister… Everything you did, she just had to do better. In the wake of your mother’s madness, you turned to dancing. You found peace in swaying as the room burnt down. Your twin sister on the other hand hated how you were lit up every room you walked into, but you couldn’t help it. There's nothing she hates more than what she can't have… so she turned to sabotage. Just when you think that your life is perfect- you're at the top of your career and you finally found love- your sister starts a rumor that you cheated on your love. Your reputation as a famous dancer goes down in seconds. But to your surprise, your lover isn't reading what they call you lately and your relationship is stronger than ever. Will you get revenge on your sister and become exactly what you despise, or sit back and let karma take over?

Popularity/romance

LTW: Become world class ballerina

Party animal, irresistible, social butterfly, hot headed, unlucky

Be enemies with your twin sister

Never be unfaithful

Have a bad reputation

Have at least one daughter

Lover- Gen 7: Cornelia

“I’d be a fearless leader, I'd be an alpha type

When everyone believes ya, what's that like?”

You've always known you wanted to change the world. Who cares if you were overlooked and discouraged. Snakes and stones won’t break your bones. You never had a big family as your father walked away from his. Sometimes it gets lonely trusting the wicked, and your loyalty was often a fault. You turn to politics to combat your feelings of helplessness, but no one takes you seriously and you feel lost in the light. You have to start from the ground up with the help of your best friend. You start to build your picture-perfect life: the kids, the lyrical smiles and the power. Will you drive away your lover by searching for their dark side, or will you put aside your ways and find the daylight?

Popularity/family

LTW: Become mayor

Good, easily impressed, brave, unlucky, perfectionist

Fall in love with your best friend

Have 10 best friends

Have children (at least one son)

Folklore- Gen 8: James

“I had the shiniest wheels, now they're rusting

I didn't know if you'd care if I came back

I have a lot of regrets about that”

You grew up trying to meet the expectations of your politician mother. Everything had to be picture perfect, even your private life. So she set you up with the daughter of one of the most powerful families in town, Betty. At first you are skeptical, but over time you fall for her integrity and affinity for old cardigans. Along the way you begin to feel stuck, tired of the sensual politics and your mother’s watchful eye. That's when you meet August -the polar opposite of Betty- and some part of you has to know what she is like. You meet in parking lots and dive bars, but after Betty finds out, you realize that summer is dwindling. In wake of losing two girls, you turn to writing: poetry and sad prose. You get lost in your stories, but once you start to gain traction, you can’t help but wonder how different your life could have been. Will you rekindle your wild flame with August or go back to the peace you felt with Betty?

knowledge/ romance

LTW: Publish 5,000$ best seller*

Great kisser, coward, bookworm, brooding, commitment issues

Fall in love with Betty

Fall in love with August

Confess to cheating on Betty

Write novels

Move into a cottage by a lake

Finally choose the one girl

Have at least one daughter with her

Evermore- Gen 9: Ivy

“And the skeletons in both our closets

Plotted hard to fuck this up

And the old men that I’ve swindled

Really did believe I was the one”

You always resented your father because he abandoned the good life for a cottage in the woods and his stories. You don’t want that; you want power and wealth. You don't need love, just a fancy car. So you turn to crime, because it’s easy for you; you love the gold rush. You con men and no one will ever prove it. You marry rich men and inherit their money when their time runs out. But then one day you meet your match, a fellow criminal, and wonder if this life will really bring you happiness. But you realized this a little too late, and now you're forced to drink your husband's wine… but he was the wrong guy. Will you leave the life of crime behind or will you stay frozen in time?

Fortune/pleasure

LTW: Gold digger

Kleptomaniac, genius, charismatic, mean-spirited, rebellious

Go into the criminal career

Marry a rich sim

Fall in love with a criminal and have an affair

Have a son

Midnights- Gen 10: Snow

“And I don't dress for villains

Or for innocents

I'm on my vigilante shit again”

You knew your mom wasn’t the most ethically-correct person. You like to think you inherited her better half; but that isn’t entirely true. You are determined to be different, so you become a spy; you get the satisfaction of working for the good guys and the pleasure that comes with great wars. Being a spy is difficult though, and you never know when things could go wrong. You are constantly burning files and deserting old lives. But you’re a mastermind, nobody can deny that. You finally meet your perfect person, but it's hard concealing your true occupation from them. You have money and respect… But can all of that pay for someone to just know you?

Fortune/knowledge

LTW: Become head of the SCIA

Perceptive, disciplined, loner, proper, daredevil

Join the intelligence career

Move homes at least twice

The rest is up to you since it is the last generation

*50 new LTW mod can be found here

if anyone decides to do this challenge tag me! i'd love to see it

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