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Summary: My personal headcanons on this rich asshole.
Author’s Note: Nobody asked for this but I WANTED IT. Because unfortunately I want him. And that’s all that really matters.
Warnings/tags: 18+ MDNI, fem! reader, mentions of bd/sm throughout, sadistic tendencies, multiple positions, oral sex, p in v sex, mentions of vasectomies, sugar daddy relationships, exhibition and voyeurism, slight pet play, impact play, degradation and humiliation, toy use, using Bevans to administer punishment, he really is a big asshole, not beta read
A = Aftercare (what they're like after sex)
Shepard’s aftercare could be better sometimes but it’s not nonexistent. He’ll clean you up, maybe cuddle with you but that’s usually it unless he’s been particularly mean or rough. After rounds like that he surprisingly takes aftercare very seriously.
B = Body Part (what's their favorite body part of yours)
He’s an ass man through and through. He likes to grab it, pinch it, etc. Sometimes you have to slap his hand away because he just can’t stop palming at it.
C = Cum (anything to do with cum, basically)
Shepard likes to cum on your face or inside you. He likes to make a mess of you both literally and figuratively. He has no objections when it comes to filling you with his cum because he had a vasectomy long ago (one awful son was enough).
D = Dirty Secret (a dirty secret of theirs)
He secretly gets turned on when you’re mean or even the tiniest bit sadistic. Sometimes he feels like he’s corrupting you with his cruelty. For a normal person that might horrify them snd make them pause, for him…it makes him hard.
E = Experience (how experienced are they? Do they know what they're doing?)
He’s very experienced. This man was married for years and had dated plenty of women before he was married and after his wife passed. He’s well seasoned and knows what he’s doing.
F = Favorite Position (this goes without saying)
Cowgirl. He would blame it on his age but in reality, this is his favorite just because he’s a lazy lover. He likes it when you pleasure him. He loves to watch your face scrunch up from pleasure while he palms your breasts. He’ll circle your clit while you grind above him.
Doggy. He enjoys it because (1) he gets to watch your ass and (2) if you have remotely any hair he can grab on to he’s going to do just that.
Missionary. Don’t be fooled by the cowgirl section, he does focus on your pleasure as well and he thinks this is the best position to do it. There are many benefits to this one but he finds that he actually really enjoys the closeness.
G = Goofy (are they more serious in the moment? are they humorous? etc.)
Unfortunately (and yes, I do mean unfortunately) Shepard can be quite humorous during sex. The issue is that he has a very sadistic sense of humor and his quips are usually only humorous to him. Luckily, he’s not like this every time. There are moments when he can be very serious during sex and his only focus is making love to you, no jokes at the ready.
H = Hair (how well groomed are they? Does the carpet match the drapes? etc.)
He’s very well groomed. He keeps his hair trimmed most of the time. His pubic hair is dark with a light sprinkling of grey much like the hair on his head.
I = Intimacy (how are they during the moment, intimately/romantically speaking?)
It depends on the moment. Sometimes when he’s in a bad mood or he’s punishing you for god knows what he can be rather cold and downright sinister. But he can be as tender and sweet as he is cold. He has a way of melting you with words alone.
J = Jack Off (masturbation headcanon)
Shepard doesn’t masturbate often at all. Why would he when he often keeps you at arm's length, right at his heels? If he’s away from you for an extended period of time on a work trip he might take the time to quickly relieve himself but usually he just waits until he can have time alone with you.
K = Kink (one or more of their kinks)
Exhibition. One thing Shepard can’t deny is that he loves showing you off and he loves claiming you. He would parade you around naked if he could get away with it and honestly, he’s rich enough that he just might be able to. He has, on multiple occasions, let his fingers wander too far between your legs while in public. Sometimes he just keeps his hand there, nestled between the warmth of your thighs and cunt but other times he’d push your underwear to the side and explore you.
Voyeurism. He doesn’t mind people watching. In fact, he quite enjoys it. His wait staff has witnessed (*cough* and participated *cough*) in a lot of his coital practices.
Power play/dynamics. Shepard likes to be in control and the bedroom isn’t an exception.
Pet play. He likes to explore this one when he’s in the mood to punish you. He doesn’t really go deep into the kink but he does enjoy having Bevans put a collar on you so he can lead you around with a leash. It does it to embarrass you and remind you exactly who you belong to.
Degradation/humiliation. Jumping off of that last point, Shepard does like to degrade you when he’s in a bad mood. He can truly be an asshole sometimes. But don’t worry, if he breaks you down he’ll always build you back up.
Impact play. Spanking, whipping, flogging. You name it—he likes it. Administered by him or Bevans because the lazy prick can’t be bothered to dish out the punishment himself sometimes.
L = Location (favorite places to do it)
Anywhere that you’ll let him. The car, the pool, his private beach, the bedroom, the front porch, the balcony. He has no preference really. He does take your preferences into consideration though and doesn’t push exhibition on you if you don’t want it.
M = Motivation (what turns them on, gets them going)
Elegance when it’s not forced and fake. Wearing clothing he picked out, especially heels and lingerie. If you wear makeup, something about dark lipstick turns him on. Teasing, especially when you’re present during the games, makes him want to bend you over and take you right in front of his guests.
N = No (something they won't do)
Although he enjoys exhibition and voyeurism, no one is allowed to touch you without his strict permission and even then there are rules to how far he’ll let it go. He may let others touch you or view you but he’s the only one allowed inside of you.
Making him submit is also off the plate. He may let you ride him but you’re not in charge, he is. If there’s a submissive bone in his body, you’re not allowed to find it.
O = Oral (preference in giving or receiving, skill, etc.)
Shepard prefers receiving. Shocking to absolutely no one. He loves receiving head from you, loves to push you down until you gag. He just can’t get over the sight of your lips wrapped around him or the tears that form at the corners of your eyes. Don’t be fooled though, his enjoyment of receiving doesn’t mean he doesn’t like to give. But he’s a massive tease when it comes to eating you out.
P = Pace (are they fast and rough? slow and sensual? etc.)
Shepard likes to take his time. He’s often nice and slow when he fucks you. That’s not to say he can’t get rough or go fast, he absolutely can and he has before. But he prefers a slower pace.
Q = Quickie (their opinions on quickies, how often, etc.)
He doesn’t mind them but at his age, he would much rather have more time with you. Quickies have their time and place but he doesn’t turn to them often.
R = Risk (are they up to experiment? do they take risks? etc.)
Oh, absolutely. He might not admit it but he is a sadist and he likes to experiment with it often. He’s also open to indulging you and exploring your kinks depending on what they are.
S = Stamina (how many rounds can they go for? how long do they last?)
One, maybe two. Shepard is not exactly the young man he used to be but he’s still in good shape. He can go for a while under the right circumstances.
T = Toy (do they own toys? do they use them? on a partner or themselves?)
He owns a collection actually. All for you. He likes to use toys on you but is not too keen about them being used on him.
U = Unfair (how much do they like to tease?)
He’s probably one of the biggest assholes around. Teasing is his bread and butter. He just can’t stop doing it. He likes to tease both verbally and physically. He likes to make you whine and pout and sometimes will only stop until there’s a nice, angry wrinkle in your forehead (or you’ve started to cry).
V = Volume (how loud are they, what sounds do they make, etc.?)
Shepard does make noise but he’s not super loud. He’ll grunt while he’s fucking you, moan when you go down on him, sing you soft praises when you’re being good for him, hum to himself when he’s exploring your folds with his fingers. He’s definitely not quiet but he’s not making a scene either.
W = Wild Card (a random headcanon for the character)
There’s really no hiding it or beating around the bush. Shepard is a sugar daddy. If being a sugar baby isn’t your thing then being in a relationship with him is probably not for you. There’s no shame in it for him, that’s for sure. He likes the lifestyle. One of his greatest pleasures is spoiling his partner, flaunting his wealth and you, and in return getting pleasure from you.
X = X-Ray (what's going on under those clothes)
Shepard is around 6 inches in length and has a decent amount of girth. He’s circumcised and has several veins running along the length of his cock.
Y = Yearning (how high is their sex drive)
Very high for a man his age. He’s still got it. He wants you and he wants you constantly.
Z = Zzzzz (how quickly they fall asleep afterwards)
Depends on how tired he was before he started. If it’s late he’s usually falling asleep not too long after. But he’s probably not going to sleep if it’s morning or the middle of the day.
Anya is live and ready to show you everything. Watch her strip, dance, and perform exclusive shows just for you. Interact in real-time and make your fantasies come true.
✓ Live Streaming✓ Interactive Chat✓ Private Shows✓ HD Quality✓ Free Actions
Free to watch • No registration required • HD streaming