#jonathan would be a wingman whether dio wanted it or not and you can't convince me otherwise

[daisys-gard3n]

ohmygod,, uh nsfw l-lawyer dio headcanons + assistant s/o 😩 pleAse ,,, afab if possible 👉👈

Ngl dio is rlly fuckable if you take away the sociopath

Lawyer Dio & AFAB s/o headcanons

If dio never took jonathan's body and never became a vampire btw

He's the perfect lawyer - cocky, cunning, charming, and great at convincing others. He's called 'the courtroom devil' for this reason

'Brando Law' is the most popular lawyer firm in london, aristocrats pay him lots if money to swindle the judge in their favor - which is where you come in

You're an intern for law school credentials, thousands of people at your college submitted applications to get to work with the Dio Brando and you were the lucky pick

He intimidated you a lot (think when kakyoin first met dio), he was just gigantic compared to you in real life. You looked like a rabbit in front of a lion.

He found it amusing how eager you were to please for a good recommendation

At first, he would just tell you to handle his schedule, make him hot beverages, take letters and telegrams, run small errands in town. Small things, really.

You were clearly frustrated, you wanted to earn experience as a lawyer, not an office assistant. After the initial formality fear melted away, you marched to his desk and (politely) asked him if you could do real lawyer things.

Dio saw how you were standing your ground, you weren’t going to leave him alone until you got your way. He’s amused, but he’s going to make you fight for it. He wants to see the passion and the dominance it takes to be a lawyer, afterall you’re getting paid to argue for someone. You need to sound convincing.

You didn’t leave him alone, like he predicted. You were on his ass, the moment he gave you the slightest bit of chance to witness the law world. You attended court hearings, taking notes as he effortlessly provided enough evidence to prove his client innocent, attended private hearings, tediously went through piles of evidence and fact checking them, and so on. 

He’s impressed, but now it was time to prove yourself: a court-like debate whether or not you were able to take on your own ‘clients’ or not. (the really miniscule clients, like property damage.)

After about a good hour or so, he took notice of your form: the flame in your eyes, how passionate you were arguing your point, your well-collected set of ‘evidence’ you presented...

And how adorable you looked, looking up at him with huffing cheeks like it was threat to him. 

Needless to say, you won and got assigned to actual lawyer business. 

Your relationship grew, from professional colleagues to friends...And more.

He would confined in his personal problems to you, since he didn’t really have anyone else. He had Jonathan, but half of his complaining revolved around Jonathan. Erina wouldn’t hesitate to beat him with an umbrella if he even went near her, that Speedwagon was pretty much Jonathan’s dog, and old man Zeppeli pretty much hated him too. 

“-So the fool knocked over one of the vases because he got distracted when his wife called over to him! Not only that, he had the nerve to track dirt all over the carpet! I’m surprised Jojo has even made this far!”

You just make him tea and listen.

You try to put some input, but he huffs and continues complaining like the diva is. Sometimes he tries what you tell him to do.

You guys get pretty close, then uh oh-FEELINGS

you’re super conflicted about having feelings for someone who is pretty much your boss

Dio would be in super denial because of how prideful he was.

He would would accidentally confide in Jojo about his feelings towards you and regret every word that came out of his mouth because Jojo put him in a strangling hug with sparkles in his eyes

“Oh, I’m so happy for you, Dio! Don’t worry, your brother is here to help!”

“L-LET GO OF ME, JOJO! I CAN’T BREATHE!”

Jonathan would then tell Erina, who would be more than happy to help him (not Dio). They would plan double dates or for you and Erina to hang out so she could get some intel. Speedwagon and Will help out too.

the feelings only get stronger

One night, you were invited to a candle-lit dinner by Dio (all planned by Jonathan). You were pretty mesmerized by how suave Dio was, enjoying the company until the final blow:

at the private balcony, looking up to the moon he would just drop:

“(L/n), come apply for a real position under me.”

“Hm? Why this all of a sudden?”

“Because...The thought of you with some other hooligan makes my skin crawl.”

Basically, said I love you and you accepted the offer with a kiss

Somewhere in the distance, Jonathan and Erina are hugging each other with glee.

Now the jooicy part y’all want:

After ya’lls first time, it gets pretty freaky: he didn’t want to scare you off from the get-go

Desk sex: major role in this

for some odd reason, Dio just wants to clear everything off his desk and throw you down on top

normally happens in the later hours of the office

he’s impatient that he has no time to be suave, he calls you over and pushes you down to lay on your back

Likes to be on top and finger you at the same time

You’ll be squirming underneath his touch, how his thick fingers spread your hole out for his cock and his calloused thumb rubbing messy circles over your clit. 

He has a wolfish grin and a glint in his eye as he teases you:

“Darling, is this too much for you? You’ve taken bigger things.”

Spreader

meaning: he likes for you to sit on his lap, he spreads your legs as far as he can before doing an action.

since he’s taller than you, he can peer down to see your tight cunt taking in his fingers or his cock. gets him riled up

He likes it for your back to face him so he can whisper up against your ear and bit your neck.

he’s massive, so he can use you as his cock sleeve.

“Darling, you’re so tight for me. Could it be that I charmed you that much? I’m flattered, dearest.”

“Spread wider, dearest. Show me how your cunt can take all of me.”

sometimes indulges in mirror sex, just for the teasing and degradation factors 

“Look at that expression, it’s befitting of a common whore. Do you really enjoy getting spread open by my cock like this? I bet you love looking at yourself like this, seeing how that tight hole takes me in. You do the wildest things to me, Wench.”

Cockwarming fanatic: he’ll force you on his cock while he does paperwork for the next hour or so while forcing you to stay still, loves it when you whine and beg for him to do something to you.

Exhibitionist 

he’ll be at a dinner with you and some clients, that’s when you feel his hand on your thigh and then start teasing you from the outside of your bottoms.

he’ll manage to weasel his way in to start teasing your clit and fingering you.

He’ll have no qualms about it, casually drinking wine and laughing alongside the guests while you’re shaking and biting your lips in order not to make any noise.

“What’s wrong, (Y/n)? Aren’t you going to speak to our esteemed guests?”

Honestly, fuck him

he’ll make you talk while he fingers you, hitting the sweet spots while you’re mid-sentence. You let out a whine, Dio smiling at the guests: 

“They just stubbed their toe on the table leg, they’re fine.”

it’s worse if Jonathan is around.

something about fucking you in the next room over with Jonathan and Erina unaware of it, the possibility of Jojo walking in makes Dio go feral 

“Imagine if Jojo were to hear us...And to walk on us, to see your sinful expression! Hng, I would love to see his face of embarrassment! I would just continue without a care~! What if he saw this pussy? Dripping all over the place and sucking in my cock? Ah, fuck~! I want more!”

His favorite position, THE MATING PRESS

HE DOESN’T EVEN WANT KIDS, YET HE DOES THE POSITION TO GET SOMEONE THE MOST PREGNANT 

Also likes standing and pounding in you while you lay on a flat surface

Want him to lose it and just fuck you then and there?: give him a blowjob underneath his desk while he’s talking to clients

He’ll have his seemingly unbreakable suave persona as a front to the client while your mouth is wrapped around him, he’ll take his hand and shove your head down so far that you might choke around his cock.

His voices doesn’t break when he talks, but you’ll occasionally get a reaction out of him that you relish in

the minute they leave, Dio peers down at you and dares you with a glare to stop. 

“I hope you’re planning to continue what you started, dearest.”

Yeah, you getting throat fucked, but god it’s worth it to see Dio embarrassed and trying to keep himself composed for once

Cum goes inside you. Birth control methods weren’t really condoned at the time because anyone who could reproduce at the time were taught to reproduce at a given moment.

Can be sweet if you squint

Must dom otherwise his ego is at risk.

If you somehow get him to be sub, he’ll be a bitch about it the whole time.

he’ll probably only do this on special occasions like your birthday or holidays.

no promises.

Punishment

You’re still in school at this point and you ask Dio to help you study for an important exam

leads to you tied up with his ties, clothes ripped open, him teasing you with different tools (spanking with a riding crop, paddle, nothing too bad), and giving you harsh punishment if you get something wrong. 

He’ll be asking you a question while rubbing the flat edge of the riding crop against your sopping cunt, you’re flustered and it’s difficult to think.

“-What is the answer a subpoena, (Y/n)?”

“I-I...U-Um...Somethin’...’bout the witness?”

“Almost, but incorrect.”

WHACK

to either your bum or your pussy

edges you on and on for hours until you’re able to say all of the correct answers, only then does he rub your clit for you cum within two seconds.

He does this with chess sometimes

You want a pussy beating of a lifetime? Make him jealous

if you want it even worse, say Jonathan might be better than him.

Good luck walking for the week.

and having hickies all over your body

Oh yeah, BITEMARKS

when he’s about to cum, he bites your neck or in between your shoulders

bites your fingers too

Alright, your sex life isn’t all whips and bite marks. There are tenderfucking moments where he or you need comfort and somehow goes into soft hand-holding sex or cuddle fucking 

Despite looking and acting so mean, Dio’s pretty good at aftercare.

wraps you up in a blanket or gets a hot bath ready for you, massages the bruised areas, soft kisses to your forehead and lips.

makes tea or a glass of wine afterwards 

Ya’ll better enjoy the sex life while you can, you guys don’t get any privacy after Jorge II is born because he wants to ‘Visit Uncle Dio and (Aunt/Uncle/Some other name) (Y/n)’ and constantly wants the two of you to play with him.

just like his son, Joseph wants to play with you guys too and won’t leave dio alone

And eventually Giorno, Donatello, Rykiel, and Ungalo follow suit because dio has weak pull-out game

Can’t have one moment of sexy times before Rykiel comes crying to you that Giorno buried his stuffed animal in the garden.

“Can’t we have one moment of peace?”

“You were the one who got me pregnant, Dio.”

“Not now, dearest...”