#I HOPE THIS WAS LOSER ABBY UHM

[elsfairy]

i think loser!abby would 100% watch your every move while she goes down on you and always ask for reassurance so she knows that she’s making you feel good…ok anyways

the way my brain short circuited 🫠

When it first happened, you had just assumed it was because it was your first time doing anything together as a couple and that she was just nervous to touch you, in case she was doing anything wrong. The first night— although every night reminds you of the first because even though she was a nervous wreck half the time, she was still gentle with you. It was something you can’t forget. You’d never forget that even if she did have two of her fingers deep in your cunt, lips around your clit, and the pornographic sounds she was able to tear from you, it was heaven for her because you just looked so goddamn pretty all spread on her bed, begging for her. “You’re so pretty, could look at you for the rest of my life—”

It was quick how those weeks of dating had turned to months, then suddenly it was 2 years, and she was still doing it. Abby took in every detail of you. There wasn’t a part of you that she wanted to miss. She loved to watch the way your brows would furrow. How your fingers would curl up in the sheet, and grip a little too tightly that your knuckles turn white. The way your mouth would open, followed by a shaky breath when her fingers would brush against the spot that always sent you crazy and how your thighs would clench around her head. If there was something she loved the most, it would be when you ramble out the continuous strings of “so good, making me feel so good Abs—” and that would send her in her own frenzy. groaning and humming into your cunt, eyes flickering between your eyes, your tits—everywhere.

Now though? watching you as she fucks you and making you cum are the only two things on her mind. Her blonde hair is thrown over her shoulder, wispy parts sticking to her sweaty forehead, and her eyes are just focused on her fingers. Watching as your cunt squeezes around them, and then she’s spewing those small “is that good, baby?” “am i doing okay?” “looks so pretty like this” “prettiest pussy i’ve ever seen” that drives you crazy and she can’t stop blushing & smirking when you’re just nodding frantically, gasping into the arm you’ve got thrown over your face.

And when your hips start bucking up into her touch, she stills in her movements, her mouth is back on your cunt— almost winding you because she’s always been so quick and she’s letting you fuck her face, ride her tongue, whatever you need— but her hooded eyes once more remain on you. and her mouth drools at the sight of you cupping your tits, squeezing them with a whimper.

The sobs of “so good, always so good” fill her ears and she whimpers into your pussy, wrapping her arms tighter around your thighs. Who cares if her jaw hurts? If she’s making you feel this good, getting a sore jaw is nothing. She’s saying something, but you can’t quite make out what— not that she would care if you can understand it, because when your hand is on the back of her head, holding her there while your thighs tighten just slightly, she's starved, eyes rolling into the back of her head because you just taste so fuckin good. And it certainly isn’t until she can hear you gasping breathlessly, body almost collapsing back on the bed that she mewls, happily and contently licking and sucking at your folds.

Every night ends with the same, “was that good baby?”

[whore4abby]

fun lil req…

u and abby are studying together n she’s not doing a good job :(( so u offer some encouragement. for every question she answers right, u take a piece of clothing off. can be loser!abby or pervy!abby or BOTH 😵‍💫🤭🩷

show and tell; abby anderson

you try to tutor abby for an upcoming college asssignment. abby has trouble comprehending the questions…until you think of a little solution.

warnings; tiny mentions of nudity + sex, mndi

wc; 0.6k

abby keeps messing up the simple equations, she feels so stupid and just wants to pound her head against the desk in annoyance. her head beginning to hurt as she's starting to get so frustrated with herself. she throws her pen down onto her desk in anger and groans loudly.

“i can’t believe i’m struggling with this…i’m a complete idiot.” she mutters, putting her hands to her forehead and sighing heavily. the room grows silent for a moment but before abby could complain more about her stupidity she feels your hand on her shoulder.

“you’re not stupid, abby.” you coo and tuck some stray hair behind her ear. she sighs heavily and nods, looking extremely unmotivated and bored.

“i think i have an idea…” you smirk and she removes her hands from her face to look at you, noticing the smugness on your face and raising her eyebrows. “what’s your idea?” she asks softly, her breath hitching as your hand on her shoulder starts to trail down her toned forearm.

“for every question you get right…i’ll take something off~” you purr, leaning in close to her ear and staring at the goose bumps forming at the nape of her neck. abby’s eyes light up and her cheeks turn a deep red when she hears your idea she takes a deep breath, nodding her head frantically and smiling shyly.

she moves her focus back to her notebook and takes the pen back into her hand and tries to answer the question again. “alright…uhm…is the answer 9?” abby queries, hoping to god that its right.

“mhm!” you nod, lifting up your arms and pulling off your sweater, revealing your lace-trimmed camisole underneath. abby looks over at you and gulps, feeling the blood rush to her face and her heart rate starting to speed up.

you watch abby working on the math problem. noticing the slight blush on her face and her hands starting to shake a little bit as she clutches onto her pen. you can’t help but grin mischievously as abby looks so cute struggling to figure out the math problem.

“okay…42?” abby asks, her voice slightly broken and high pitched as she points to the question on the paper. you check over her answer and shake your head pitifully, “try again, baby~”

she puts her head back down, her pen frantically scratching against the notepad and her shaky fingers prodding at the keys on her calculator. her voice wavering as she struggles to keep her composure around you, “uhm…is it 45?”

“yeah. good job, abs…” you smile sweetly as abby finally gets the question correct, looking into each of her wide eyes before moving your eyes to look at her lips, quickly ripping your gaze away to pull off the camisole covering your torso.

you’re left in your bra, nipples hardening against the thin lacy material, watching as abby’s eyes dart from either side of your chest, lingering on the fat of your breasts spilling out over the edge of the seam.

you laugh at abby’s reaction, finding enjoyment in watching her become more and more flustered with each minute.

abby tries to ignore it. to ignore the way her heart is pounding and her head is starting to feel dizzy. she can’t help but bite her lip as she stares down at the valley between your tits with absolutely so shame. eyes bugging out of her head as she practically drools, imagining what you would look like without your bra on, tits bouncing in front of her face as you ride her.

“and would you look at that….that was the last question!” you giggle and close over her notebook with a subtle thud before standing up and grabbing your clothes. you quickly slip them back on while she watches, her mouth agape, lips parting and pressing together again as she struggles to form words.

“t-thats not fair!” she splutters and pouts at you, wanting nothing more than to reach out for your hips and to drag you down onto her lap.

“bye, abs~” you giggle and lean over to kiss her flushed cheek before grabbing your things and walking out of her room nonchalantly, looking back over you shoulder and waving at her innocently.

[actuallyknowntobequitevexing]

Dean / New Feelings

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"I can't believe you dragged me into this." Dean huffed, putting the car in park and staring at the fancy dining hall in front of you two.

"Look, you agreed to it, now let's get it over with." you said firmly. You didn't want to be there either, but you felt obligated. It was your friend Abbie's birthday tonight, and her parents were throwing her an extravagant, over-the-top party, as usual. You hadn't been to one of her parties in years (because you absolutely hated them), but you decided to come to this one because it was her 21st birthday. Plus, she really needed you there; you were the only person who she could complain about the party to.

You didn't want to seem like an outcasted loser who's been hunting monsters and hasn't lived a normal life in almost four years, so you begged Dean to come with you. People who went to your high school would be there, and you wanted to seem like you were succeeding in life. The last thing you wanted was to be talked about.

"This dinner that you're paying for better be freaking worth it." Dean grumbled. He shut off the engine and got out of the car. You followed suit, readjusting your new (and really fucking expensive) red floor-length dress. You were annoyed that you had to buy a really nice dress for the occasion, but you couldn't deny that you felt sexy in it.

You and Dean walked up the steps to the dining hall. "Just, be nice, Dean. Please." you plead to him.

"I'll try my best. You know I hate these things." Dean stepped forward and opened the door for you, catching you off-guard. The gesture was simple, but it made your heart flutter.

Wait, what the fuck? you think. That was weird. Why did I feel that?

You've never had feelings for Dean before, but you couldn't ignore the giddy, girlish feeling you felt just now.

Pushing the thought aside, you walk into the dining hall. Dean steps by your side, looking just as horrified as you do. Everything was white. The walls, the tables, the decorations, the food, the lights - everything. The dark wooden floor was the only contrast to the blindingly bright room.

You and Dean share a nervous look. He offers his arm to you, and you snake your arm around his. You two start walking through the elegant crowd, populated with people who were dressed a billion times nicer than you two. You felt like you shouldn't even be near such expensive clothing and jewelry. You were careful to not bump into anyone, in fear of ruining someone's dress or drawing attention to yourself.

"So, am I your boyfriend, your friend, your second cousin, what?" Dean asks quietly.

You hadn't thought about that. "Uhm, I guess-"

"(Y/N)!!!" a shrill voice exclaims. Mary, a girl from your high school, runs up to you, bouncing gleefully with (what seems like) feigned delight. She grabs you in an embrace, and you're stunned but awkwardly hug back. "Oh, darling, how are you? It's been so long!"

Mary annoyed the hell out of you. She was one of those girls who thinks that everybody likes her and wants to be her friend. You're pretty sure you've spoke to her, like, twice in your entire high school career, so you're not sure why she's acting all buddy-buddy with you now.

You smile politely and say, "I'm good-"

Mary cuts you off, as if you weren't saying anything. "And, who is this handsome man on your arm?" She pushes a finger against Dean's chest, teasingly.

Dean looks uncomfortable but answers, "I'm (Y/N)'s boyfriend."

Okay, well, this is happening now.

"Oh, how lovely!" Mary exclaims. She leans over to you and whispers, "Nice job, (Y/N)."

You smile nervously. "Thanks. He sure is a looker." You nudge his side.

Dean and Mary laugh uncomfortably.

Uhg, way to go, (Y/N).

"Well, it's great to see you again, (Y/N). We definitely need to catch up sometime over dinner! I'll bring my hubby, and you can bring your man, too." Mary's white teeth are starting to blind you.

"For sure!" you exclaim excitedly. As she turns and walks away, you mutter to Dean, "That's never gonna fucking happen."

He smiles, laughing softly. You notice that he's staring at you weirdly.

"What are you looking at?" you question, raising an eyebrow.

Dean opens his mouth and quickly closes it, like he's just realized what he was doing. "I've just never seen you in a dress before. And all this," He gestures vaguely to your face, "stuff."

"Makeup?" you laugh. He nods, and you roll your eyes. "I wear makeup, Dean."

"Yeah but not like," He gestures to your face again, "this."

"You need to cool it with," You gesture to his face, "this, or I'll smack the crap out of you, got it?"

Dean nods and straightens his posture up, getting back into his role as "your boyfriend". You two walk over to the bar and Dean orders two glasses of Scotch. You gladly down your entire glass, wanting this night to be over. Dean chuckled at you, calmly downing his glass, too.

Someone bumps your shoulder rather roughly, pushing past you to get to the bar. You turn to glare at the person, but realize that it's Abbie.

"Give me the strongest thing you got." she desperately begs the bartender, both arms extended on the bar dramatically.

You roll your eyes at her, poking her side. "Hey, there's people standing here, you know."

Her head whips around and she seems to have just realized that she had pushed past a person. "Oh my god, (Y/N)." She threw her arms around you, leaning her weight against you exasperatedly. "I'm so glad you're here. I'm about to blow my fucking brains out. Seriously, my mom won't stop talking and talking and talking and constantly nagging me about my posture and how I'm acting and my dad is trying to get me internships at all these fancy colleges that I don't really want and-" Her posture immediately straightens, releasing you from her hug. She had just noticed that Dean was standing next to you. She tucked a stray piece of hair under her bangs, bringing her lips inwards, obviously embarrassed.

"Hi." She smiles at him, trying to act as if she didn't just have a pity fit in front of him. She tugs your arm and asks quietly, "Who's this?"

You feel secondhand embarrassment for her, but just laugh because Dean was, luckily for her, not another stuck-up attendee of her party. "This is Dean. My friend."

"Boyfriend." Dean whispers quickly, trying to remind you of your feigned relationship.

You put a hand on his shoulder reassuringly. "It's okay, this is my friend Abbie. She knows we aren't dating."

At your last statement, Abbie raises her eyebrow at you challengingly, as if saying, "Are you sure about that?" You roll your eyes and nod slightly, trying to keep this exchange away from Dean's attention.

"Interesting," she almost whispers. You can see the wheels turning in her head, trying to come up with some elaborate backstory between you and Dean and catch you in a lie. She smiles pleasantly again, takes Dean's hand, and shakes it politely. "Well, Dean, it was very nice to meet you. (Y/N), we'll be talking later. I hope you two enjoy the party." She wiggles her eyebrows teasingly at you, grabs her drink from the bar, and walks away.

You close your eyes, sighing at the thought of having to defend your and Dean's platonic relationship when you talk again with Abbie.

"Well, she seems like a hoot." Dean says, trying to edge you even more. You jab your elbow into his side, and he chuckles, amused at your discomfort at this gathering.

For the next hour or so, you two mingle with most of the party, though most of the interactions were against your will. You and Dean were devestatingly bored with the party, but, every time you tried to leave, another person would come up to start a conversation. Most of them were people who went to your high school, interested in recounting all of their achievements and, ultimately, just hearing themselves talk. You were polite and friendly, and Dean mostly remained quiet. Sometimes, however, he would snake his hand around your hip while you were mid-conversation. His touch never ceased to startle you, and you secretly wished he would touch you more...

What. The. Fuck. Are. You. Thinking.

You shook off any romantic, dreamy thoughts regarding Dean, and tried to focus on faking your way through this party. Dean was only making it more difficult whenever his large, warm hand would find its way to your hip or your lower back. You were sure he was doing this to just add credibility to your two's "relationship", but you couldn't stop thinking about him, and how you never wanted him to leave your side.

At one point during the night, you and Dean wound up talking to a really nice elderly married couple. They looked to be in their sixties, and their names were Sarah and David. While David and Dean began talking about classic cars and rock music, Sarah leaned closer to you, placing her hand on your knee. "So, (Y/N), how did you and Dean meet?" she asked, her eyes gleaming with curiosity and happiness. You could tell she was a romantic.

Well, you couldn't tell her how you and Dean really met, so you decided to tell her the watered-down version. "I was caught up in some trouble a few years ago. I was going down a really dangerous path."

"I'm so sorry to hear that, (Y/N)," A look of worry washed over her face. "I'm glad you're okay now."

"Well, truthfully, I probably wouldn't be okay right now if I hadn't met Dean. He saved me one night when I was in in really deep trouble, and we became really good friends after that. Me, him, and his brother. They've become my family, and I'm really grateful for them." You smiled at your words because you had never acknowledged how much you loved the Winchester brothers until that point. You raised your eyes to look at Dean. He caught your glance, giving you an adorable closed-mouth smile before returning to his conversation with David.

You feel a rush of heat inflame your cheeks, and you turn back to see a smiling Sarah. She gave you such a knowing look, like everything just fit into place in the matter of just a small exchange. She touched your knee once more and said quietly, "Hold on to each other."

You smile once more at her, and she joins Dean and David's conversation, leaving you to your thoughts.

Does Sarah see something that I don't?

You pushed away those thoughts once more, and tried to concentrate on their conversation.

About an hour later, you and Dean decided to call it quits. You both told Sarah and David goodbye and thanked them for the company, then you found Abbie to tell her you were leaving. She reminded you of the conversation she wanted to have with you, and you promised her you would call her soon. You wished her a happy birthday, hugged her goodbye, and made your way to Dean's car.

You two drove in a sleepy yet comfortable silence. You knew you were definitely going to bed as soon as your head hit the pillow. In your sleepy haze, you lazily touched Dean's knee and said, "Thank you for coming with me. I hope you weren't as miserable as you expected to be."

He smiled and reached over to grab your hand, resting them on your leg. "I had fun." He glanced over at you, absolutely melting your heart. His thumb rubbed back and forth on your hand, soothing you and making you sleepier.

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