Peachy

EXTREMELY into it. Absolutely forces you to watch his dick get red as he thrusts into you. While he prefers to receive than give oral, your period is the one week where he has 0 interest in you sucking him, he is burying his face deep into your cunt and kissing you afterwards. Despite how much he loves it if you ask him for it or if you are too into it he teases you relentlessly. Will be forcing you to panties free during that time. If you bleed into any of your underwear before that rule is enforced he takes it from you and keeps it.

Kylar

#1 period sex lover. As I said on twt : he always is more into giving oral than receiving but if you're on your period he is going to be accidentally overstimulating you. Unlike robin, kylar is actively BEGGING you to let him touch you during your period, his face is buried between your thighs and he is barely coming up for air. You need to shove his head away if you want him to stop. Used underwear gets stolen, except unlike Whitney he does not stop at one pair.

Sydney

Pure sydney is very blushey about it. Curious but mostly doing it because you said it will help you aliviate cramps. Corrupt sydney is another one to be extremely into it. Unlike Kylar or Whitney (who prefer giving oral and thrusting ) he has no preference when it comes to it, you want him to suck you? Actually fuck you? Use his fingers? He is into it all. If he uses his fingers after you cum he is going to lick them in front of you.

Eden

Another one very into period sex. There is a primal thrill to it, his breeding kink kicks in even harder, and it makes him get more rough with you. Actively against you wearing menstrual products, he is weirdly into the throught of your free bleeding. Also another one who while he has a preference for receiving oral, would be continually going down on you (not as much as Whitney tho) during that time.

Alex :

Natural about it. He has grown up in a farm he doesn't get disgusted easily, so while respectful he would be confused (and at low dominance blushey) if you throught he wouldn't want to have sex with you during your period. If you want low dominance Alex to go down on you you'd need to tell him, high dominance Alex seizes the initiative by himself especially if youre feeling shy/unsure if he'd want you during that time of the month. Didn't think he'd be that into it but to a lesser extent than Eden also gets a small primal thrill at watching you paint his dick red while he is deep into you.

Great Hawk and Black Wolf :

You in your period awakens the breeding instinct in them. You are not allowed to leave the cave/castle they need you inside resting and ready to be pounded into. Honestly the only ones to be even more into period sex than Kylar.

Avery :

The love interest least likely to be into period sex. Your sex life at that time strongly depends on your relationship: If Avery just likes you he expects you to be giving him oral without getting anything back. If Avery prizes you, and especially if you are shy on the idea of period sex he is hands on. The idea of it seems icky to him, but after the first time thrusting into you? He starts to come around to it. Still not one to be over the moon over it (and receiving oral from him during that time would be close to if not impossible), but he is ok. If you bleed on any furniture you are getting punished, and if he likes you he forces you to go without menstrual products and makes a game out of watching you try your hardest to not leave a stain in anything least he takes you to the dungeon.

Gwylan

SO into it. Like great hawk and black wolf it awakens the breeding instinct in him even more. Expect to be chased through the forrest (and probs fucked right there, doesn't really have the mind to transport you back to the shop, best he can do is get you back to the garden sometimes) and hear even more talk of you having his kits during that time. He loves giving oral regardless,but when you're on your period? The times he can get himself to wait before he actually gets inside you, he is gonna overstimulate you ( and unlike Kylar, Gwylan is one to know exactly what he is doing) with his tongue. If you cum while he eats you out (and especially if he has already cumed inside you) he is gonna kiss you.

Wren :

The library is still... but still open.

School finished a half hour ago, and the students are long gone – you can’t blame them. It’s a beautiful Friday afternoon and the sun is shining, inviting almost everyone to go outside and enjoy the weather. It’s unsurprising to find Sydney still working. At least that’s what it looks like he’s doing.

Sydney sits behind the counter, as usual – amber eyes downcast over a book. His tongue peeps gently in concentration. He’s so rapturously engrossed, in fact, that he doesn’t notice your approach. He’s caught off-guard as you speak.

“What you reading?” you smile fondly, leaning over to get a good look at whatever has Sydney so absorbed. He’s pleased to see you, letting the book settle against the top of the desk. There’s a magazine inside.

“Just doing some research,” he replies with a gentle, sleepy smile. “This came free with a delivery to Mum’s shop. It’s… an interesting read…”

You don’t doubt it. Lately, Sydney was consuming anything he could find in an effort to expand his horizons – all thanks to you, apparently. As a good girlfriend, you’ve been more than happy to support his journey to enlightenment. Perching on the edge of the counter, you crane your neck to see what had Sydney so immersed this time.

“… Nipple orgasms? That’s… a thing?” your nose wrinkles doubtfully – but Sydney seems quite confident in their newfound knowledge.

“Apparently, love,” he stands, planting a chaste kiss against the flat of your neck. The subsequent kisses aren’t quite so chaste. “Maybe it’s something we could try together?” he whispers against your flushed skin, causing the hairs on the back of your neck to prickle.

You hum and lean against him. What a good idea. Idly, you tease at the pages of the magazine, enjoying his soft lips against your neck. It’s clear he’s willing you to react, but you’re happy to let him try a little harder.

A heavy textbook slams against the counter. You’re both startled, and it’s no accident. Neither of you had noticed Whitney approach, and now he looks down at you both with an expression that’s hard to place.

His eyebrows raise as he smiles wryly. “Having fun there, slut?”

You nod, and can’t hide a smile, too. Whitney had never felt threatened by Sydney – or so he said - but they shared sort-of… a mutual rivalry when it came to your affections. You were always very happy to act as mediator.

Whitney leans over the desk, glancing over the article with disinterest. “This got you all hot and bothered?”

Sydney nips at your neck delicately, causing you to yip in response. You feel him smile against your skin, before he turns to Whitney with surprising aloofness.

“Just leave your book in the returns basket,” he drawls – stopping just short of physically shooing Whitney away. The bully isn’t impressed.

“What, you’re gonna give her one?” he scoffs, arms folding over his lean chest. “Fuck right off.”

“Actually, there’s quite a nuanced technique,” Sydney retorts, eyeing Whitney and tapping the magazine with one finger. Even you’re surprised by his conviction, and he’s not even finished. “You’d know that if you’d ever bothered to read about it, Whitney.”

Here we go.

“What, you’re a fucking expert now?” Whitney scorns, moving closer to you and possessively gliding his hands around your waist. You’re sandwiched between them, and it’s easy to feel affected by the prickling intensity with which they hold themselves. Your eyes settle on Sydney, wondering how he might respond.

“If you’re so confident, then you won’t mind demonstrating, will you?”

If Sydney’s intention is to make the bully back down, he’s going about it all wrong. Still, it’s not like you’re complaining. You notice the hint of a smile playing at the corners of Sydney’s lips which suggests he knows exactly how he intends to play this.

Whitney huffs, already unbuttoning your shirt - muttering fiercely and unable to hide his agitation. The tiny buttons of your blouse aren’t fucking helping. “If anyone’s gonna make you cum like that… it’ll be me…”

You can’t suppress a soft whimper. You don’t doubt Whitney’s confidence – you don’t doubt either of them, to be honest – and anyway, it’ll be fun to let them try. Once unbuttoned, Sydney slips your shirt from your shoulders, bunching it and stashing it somewhere out of sight. Your bra soon follows – it’s a clear flex when Whitney unhooks it with a single swift motion. Sydney will want to practice that later.

Gingerly, you scooch into the middle of the desk – levelling the playing field somewhat. Sydney and Whitney flank you, and for a brief moment, their eyes are fixed not on you, but each other. Plainly, they have no interest in hiding their growing contention.

To no one’s surprise, Whitney dives in first; too confidently, as could be predicted. He lowers his head and greedily draws one nipple into his warm, wet mouth. He’s intense, as always – tugging forcefully as he sucks, sweeping the metal of his tongue stud over you ravenously. You can tell he thinks it’s some kind of secret weapon – probably because you’ve never told him any different.

In contrast, Sydney takes his time, fingers skimming delicately over your breast. He leans closer to whisper encouraging words against your ear – you feel yourself melting a little as his long hair tickles your cheek. “Just focus on breathing, love.”

You’re already nodding faithfully in reply. Eventually, Sydney begins to tease one hardened nipple under his fingertips – featherlight as he traces soft kisses down your neck and collarbone. His soft touch invites a whinny of desire from your parted lips.

Not to be outdone, Whitney grips your jaw, roughly turning your head and assaulting you with a deep kiss. It’s all friction, tongue and teeth – hungry and rude, everything Whitney stands for. Then, he’s biting the crook of your neck restlessly as he pinches and pulls at your tit. It’s like he can’t settle down – unlike Sydney, who’s seems to know exactly what sort of delicate treatment is required.

You close your eyes, allowing a shaky breath to rattle from your lungs. There’s a soft hand holding yours. Sydney’s taking his time, still – gently nudging your breast with his nose, dusting soft kisses over soft flesh. The wet, warm blade of his tongue skims over your erect nipple, causing you to arch your back and tip your head upward.

Whitney’s rough fingers leisurely trace small circles along your inner thigh, then up and under your skirt in a familiar journey. Legs part instinctively. "Bet you’re so fucking wet for us, slut…" he growls against skin.

You groan out an answer, but it doesn’t matter – he’ll soon discover he’s not wrong. Whitney’s fingers nudge the slick surface of your underwear, easily finding the outline of your swollen clit - the thin fabric already dense and clinging. But before his fingers can sink into your core, he’s pulled away. You rumble with loss, body twisting against the counter in frustration.

“That’s against the rules, Whitney,” Sydney chides, his voice purring against you. Purposefully, he guides Whitney’s hand back into your lap. You feel the combined weight of their hands settle there – hovering infuriatingly above your centre and almost certainly on purpose.

“You’re just pissed you didn’t think of it," Whitney mutters hotly. His teeth catch against your sensitive skin, making you squeak. Then, he’s gently suckling, almost apologetically, sliding his tongue stud over your nipple and brushing against your soft skin as one rough, possessive hand roams your skin and pulls you closer.

You wish they’d stop talking and just focus. But all the same, a surprising, welcome sensation blooms in your gut, flourishing just below your bellybutton. You hadn’t expected it to feel quite like this – there’s even a gentle, promising tickle in the base of your clit. You close your eyes, narrowing your focus, fanning the embers of your stirring climax. Focus on breathing.

But’s a slow burn. There are irritating moments where they seem more interested in distracting each other than they are with getting you off – bickering annoyingly across you, competitive and vying for dominance in their own distinct way.

Unbeknownst to Sydney, the bully’s gripped your wrist and is now boorishly grinding his erection against your palm through his trousers. You’re not sure if it’s against Sydney’s rules – but you choose not to mention it. Meanwhile, Whitney’s alternating between flicking your nipple with his venomous tongue and sucking on it greedily. “Fucking sensitive, aren’t you slut?” he rumbles against your flesh, noticing you quiver.

Sydney actually scoffs, taking a moment to pull away from your breast, unable to resist a clever comeback. “You didn’t know how sensitive she is?” Sydney can’t help teasing– clearly, he’s emboldened by your reactions, and is feeling quite confident with his technique. To be fair, he should.

Still, you wish they’d shut up and concentrate.

"Please… I really need to cum..." you plead, breath quickening needily. It’s maddening – orgasm feels so close, but infuriatingly out of reach. When you focus too hard, it flutters away, slipping through your fingers like sand. Now, it’s getting hard to think of anything except being fingered roughly against the counter, or being bent over to cum hard on cock… craving release badly now as you slither pitifully against the desk, getting almost no relief thanks to the flat, frictionless surface. You’re at their mercy.

Jolts of sensation flutter and bloom in your chest, just behind Sydney’s diligent fingers. He ghosts his lips against your ear - his warm, encouraging voice eliciting another shiver. It’s possible to hear the smile in his voice. "You’ll cum, my love. Have faith."

You swallow hard, wanting to believe him. But it’s hard.

“I can’t…” you whimper, grinding down on the desk in pure frustration. Sydney places a finger to your trembling lips, but it’s Whitney who shushes you gently, nipping at your jaw, his voice low against your ear.

“Me and Temple boy are gonna make you cream that pretty pussy… so be a good girl, and shut up.”

You’re panting. Yeah, that’ll do the trick. Whitney knows it, too – his gravely dirty talk spinning you darkly closer to the edge. Climax rumbles and threatens within – muscles tightening, knees shaking…

Sydney runs his tongue over your collarbone, tweaking your nipple tenderly. “I can feel you’re close, beloved,” he coos. “Let go.”

You can’t suppress deep, shuddering moan as your orgasm crashes down, splintering through your insides; it’s as though every muscle tightens, dreadful and deep and crushing. Between your thighs, your cunt pulses – starved of anything to clamp down on but twitching delightedly all the same.

It’s surprisingly intense – there’s a moment where you can’t move – settling for gripping their hands gratefully in your own as your shattered breathing settles. Slowly, the thumping in your chest subsides too, but the tingling in your nerves lasts a little longer.

“That was my side, right?” Whitney’s too cocky – instantly, he’s fucking embarrassing sometimes. Practically euphoric, strutting annoyingly around the counter. “I fucking win!”

“That’s… not really how it works…” is all the explanation you can muster – but it’s clear he’s not listening, all-but pumping his fist in triumph.

Sydney gives you a knowing smile. “I know you’re just sparing his feelings.” You’re not exactly sure what he’s implying.  He removes his glasses and wipes them with a cloth – they’re foggy. “I’m a fast learner, don’t you think?”

You smile back. Either way, Sydney will be happy to have added something new to his growing repertoire – and you’re very happy too.

“Come on, slut,” Whitney shoves your shirt rudely against your bare chest. “Get dressed, I’m taking you out to celebrate.” You roll your eyes - as usual with Whitney, it’s not clear if there’s a choice.

“No, she’s coming to Elk Street with me,” Sydney states firmly, turning towards you. He shoots an imploring, flirtatious look that’s now well-practiced and difficult to resist. “Right?”