#captain jenna

You’re fucking your boss, captain Jenna, who you’ve had the hots for ever since you were assigned her team. Unfortunately you just got your period. Fortunately for her, a period ain’t ending nothing but a sentence.

wc: 1.2k

a/n: experiencing homosexual thoughts hnnnggg ignore any mistakes pls and thx

You are to go on a date with her. All dressed and dolled up, you watch her apply the finishing touches to her makeup; a cute, nude-pink lipstick topped with peach scented gloss, and she looks absolutely gorgeous. You’ve been looking forward to this date for almost a week now, so you start feeling a bit anxious. And the anxiety isn’t unfounded, because you start feeling sick right before you’re about to head out the door.

A stabbing pain in your lower abdomen, and a sudden wetness in your underwear no it can’t be— you take out your phone and check— no it wasn’t due for another few days, what the hell. No this can’t be, it was supposed to be a perfect day…

“…Jenna” you venture

“Do you feel ill?”

“…yes. I think… I think I just started my period. I don’t— I don’t know why— it wasn’t supposed to—“ your voice cracks and wavers as tears blur your vision.

“Hey, hey. There, there. It’s alright. Do you want to stay in instead? I can run you a bath and give you a massage”

You just squeak and nod, dejectedly making your way to the bathroom, cursing Mother Nature for cockblocking you so cruelly. You clean up and go to sit on your bed and she joins you shortly with a cup of tea.

“It’ll help with the cramps”

“… thanks,” you take a sip. “I’m… I’m sorry”

“There’s no need to apologise, our bodies can be unpredictable sometimes. It’s not your fault”

You nod pensively and take another sip of the tea. A kettle goes off, and she goes to take it off the heat. She returns with a warm water bottle.

“This should provide some relief” she says placing it on your lower abdomen.

“Better now?”

“Better” you say. You’re still sad at your date being cancelled so unceremoniously, and your pitiful look doesn’t get unnoticed by her. She pushes a strand of hair behind your ear and gently pats your cheek, looking sympathetic.

“It’s ok” she says, and kisses your cheek, leaving a glossy, light-pink lipstick mark there. She looks at it and smiles.

“You look cute” she remarks, making you blush. she shifts so your legs are draped across hers, and continues playing with your hair, so close, oh so close and you can feel your heartbeat quickening as you unconsciously shift closer to her hoping for another kiss. Hopefully on the lips this time.

She looks at you amusedly, and smiles. Her hand snakes to the back of your neck, pulling you closer, making you gasp. She chuckles, and then locks her lips with yours; so soft, and tasting like the peach lipgloss she was wearing. It was a gentle intrusion when her tongue pried open your mouth and explored you languidly, your chest rising and back arching to be nearer to her.

She holds your face in her soft hands; stroking your cheek, tangling in your hair, pulling you closer as your unsure hands ball into fists at your sides gripping the sheets. She takes your arms and puts them around her, encouraging you to touch her in ways you’ve yearned for, for so long. Her kisses trail away from your lips, to your cheek, then to your jaw and down your neck, sliding the strap of your dress down as she worshipfully kisses your shoulder and collarbone

“Let’s get you out of this dress yeah?” She says softly, her voice low.

You take off the straps and she unzips it from behind, helping you out. You’re just in your bra and panties, and her eyes rove over your body, admiringly. Perhaps lingering a little too long on your tits.

“Do they hurt?” She asks. You nod, move back, spreading your legs to accommodate her body as her hands slowly, patiently begin to massage you.

Soon you’re gasping under her touch and her hands slide down the sides of your panties, and you look at her unsure, and she just smiles at you

“I’ve drawn blood from more sinful places. Why would I be disgusted with blood not born from violence?”

-x-

You’re a mess under her. A sweaty, drooling, crying, moaning mess as she snaps her hips forward delivering thrust after dizzying thrust. You’re on your stomach, hugging a pillow, biting it, screaming into it as she continuously pushes into you, grazing that spot with the silicone toy, rhythm unfaltering, her hand at the back of your neck gripping, grounding, present.

You can feel each and every ridge of the fake veins inside you, your walls so sensitive, spasming around the cock, taking you to dizzying heights as your back arched under her lifting up your ass even more as her slender fingers roamed your curves, gripping your hips pulling you back on the strap, making you squeal.

“F- fuck… hnnn…Jenna— ah!~”

“Baby I know” she coos, not slowing down, now her hand in your hair pulling your head back, deepening the arch, turning your head to face her and kissing you deeply, her shallow thrusts kissing your cervix making you moan into the kiss, which are swallowed by her.

“If only you could see yourself right now” she said kneading your ass, watching the strap slide in and out, a bloody, wet mess.

“So, so pretty for me” She kissed the back of your neck, a hand slipping under you to play with your tits. You moaned into the pillow, feeling her so deep, her soft hands on your body, groping, massaging, claiming.

“Fu- fuckfuckfuck— ngh… j-jenna— i- im gonna… I’m gonna— hck!”

“Cum for me baby, make a mess” sure says encouragingly as you start to gush around the strap, dripping down onto the towels she had laid down. She watched you drip as if in a trance, hands still gentle.

You were gone. Hugging a pillow for dear life, stained with tears and eyeliner as it muffled your loud gasps and filthy moans as she dragged her cock languidly in that special spot inside you which made you shudder. Drool streaking down the corner of your mouth, brain dead.

You turn your head back to look at her and your eyes roll back. The sight downright illegal. Sinful. Hot. She’d gotten rid of her top as well, and your eyes dragged along the curve of her waist, down to where the straps were visible, subtly defined abs that glistened under the light, her hips moving rhythmically making you gasp. Her face a picture of serenity as she looked down at you and smiled.

Your eyes shut involuntarily as she dragged slowly inside you, a slow shallow thrust, followed by a few rapid, shallow ones. the same pattern again and again. you felt as though you were being wringed out like a flimsy piece of fabric before you blacked out for a moment, before regaining consciousness.

She held your hips, massaging them, getting all the soreness out, before finally pulling out of you, letting you fall onto the soft mattress. you laid there like a deflated balloon while she cleaned herself and then you. a soft, warm and wet towel gently on your skin, cleaning away the mess of blood and cum on your thighs and tummy.

She was so very gentle with it, her care almost motherly. She wiped your face, streaked with makeup running down your face with a wet wipe, before giving you a couple of reassuring kisses. She had gotten rid of the old towel and put a fresh one down for you to lay on while she got your bath ready. 

Masterlist | More Viper

Home Remedy | Jenna x MC | Prompt: Allergy

Current day. Jenna takes care of MC who is dealing with some extreme allergies. She brings by some...tea. What IS that? Why is it blue?

Achoo! Achoo! Ah! Ah! Ok, I think I’m ACHOOOOO!

“Ugh!” I moaned as my hand stuck out of my blanket cocoon to find out that I no longer had any tissues.

Wait. Maybe there was a box on the floor? I looked, but the only boxes were empty. No! Under my bed! There had to be…

“Lookin’ for this?” Captain Jenna showed up and had a tissue box open for me.

“Oh my gosh, yes! Thank you!” I grabbed one and blew my nose. “How’d you…?”

She chuckled, “Xavier let me in with the spare key. I hear you were really being attacked by allergies, so I thought I’d come over to help out. I brought you some cough drops and allergy medicine and tissue. Do you mind if I use your kitchen?”

Need her to shove my face down between her legs and suffocate me

Need her to be whispering sweet nothings in my ear while she is inside me

I need her to give it to me so hard and so good that I get a pregnancy scare

I need to suck on that strap while she’s wearing it and I want her to pat my cheek saying what a good job I did and then spit in my mouth