18. Masturbation ~ Wilhemina Venable (nsfw)
I've been in outpost three for five weeks and four days now, and I'm terribly crushing on the strict and scary outpost leader, Wilhemina Venable. I always get aroused when I'm in the same room as her, my thighs quivering upon hearing her cane tapping against the floor. And the way she mindlessly caresses the handle of her cane while she eats or talks makes me squirm. I thought about touching myself, but I'm really scared of being caught and punished. I mean, I don't even know if masturbation is against the rules, but I'm not taking any chances.
In the past few days, I've tried multiple times to pleasure myself, but the moment I'd hear any sound or no sounds at all, I would chicken out. I even thought about asking Ms. Venable if it's allowed to pleasure yourself, but I haven't worked up the courage to actually do it.
Currently, there's a gathering in the music room, in which Ms. Venable informs us about the development of our situation, which is non-existent. At the end of the meeting, I'm basically a puddle, because I've observed everything Ms. Venable did in the past thirty minutes intensely. I doubt that I can stand up straight right now, the sexual frustration too much for me to handle.
A while after everyone left, I slowly make my way towards Ms. Venable's office, knocking gently, once I'm there. I enter after hearing a stern 'come in'. Opening the door, I see her sitting in her chair, looking up from an opened file. I swallow and gather all of my courage. "I-I only have a quick questi-"
"Close the door and sit! We are civilized here," she interrupts me, and I do as told, my thoughts running wild, already planning the quickest escape route in my head. "Now what is your question?" Ms. Venable asks and looks at me expectantly. I swallow the lump in my throat and lower my eyes. "I-It's nothing important…I-I should go," I say and make a move to get up, but she is faster, standing behind me and pushing me back down into the armchair.
"Now, you already wasted my time, so you might as well ask what you came here to ask," Ms. Venable almost purrs into my ear, causing me to whimper quietly, clenching my thighs. Her gloved left hand rests on my neck, and my breathing quickens as goosebumps erupt on my skin. "Ask your question, Ms. l/n!" Ms. Venable orders strictly, digging her fingers into the skin of my neck.
"Is masturbation against your rules?" I blurt out.
After realizing what I just said, I place my hand in front of my mouth and panic, ready to run. But Ms. Venable pushes me back into the seat. "Yes, it is indeed. Why, have you already broken this rule?" she questions, her voice laced with both honey and venom as she walks in front of me, towering over me.
"N-no, of course not...but I wanted to," I mumble the last part.
"And why would you like to pleasure yourself, hmm? What makes you so desperate to touch yourself, Ms. l/n?"
I shake my head and try to get away again, but Ms. Venable places her left hand in the middle of my chest and keeps me in place. "Answer me!" she demands, but I shake my head again. "I said ANSWER ME!" Ms. Venable says and grips my chin with her left hand.
"YOU!" My eyes widen in horror as soon as the word left my mouth.
"I beg your pardon?" Ms. Venable says, narrowing her eyes and coming dangerously close to my face. I close my eyes, readying myself for any sort of punishment, but instead she walks behind me again and whispers into my ear. "Say it again."
I moan quietly and rub my thighs together.
"You," I whisper.
"Elaborate on that, Ms. l/n." I gasp as her fingers start to dance over my neck. "Come on, Ms. l/n. Don't be shy now," she says.
"I-I can't get you out of m-my head. Y-your presence in a room is so captivating, and every little thing you do excites me. I-I can't help it."
"Hmm...you have my authorization," she whispers into my ear.
"What?" I ask confused.
"You may pleasure yourself," she purrs against my neck and I shudder. I move to get up, but she keeps me in place. "Here and now, Ms. l/n. And only in my presence so I can supervise," she says, her voice dropping an octave at the last word.
My eyes widen as she leans against her desk, looking at me with her piercing brown eyes. I hesitate but decide that I'm way too desperate to deny myself an orgasm, even if it has to happen in front of her. I lift my skirt and slip my hand into my underwear, moaning softly at the wetness it encounters there. I run my middle finger gently over my clit, twitching slightly.
Then I look at Ms. Venable, staring into her eyes as I circle my clit faster, moaning louder. Sliding a finger inside myself, I close my eyes and imagine the woman who's standing in front of me doing these things to me. I add another finger and start to massage my breast over my dress. In a matter of a few minutes, I'm a moaning mess, pulling my fingers out of me to rub my sensitive clit in fast, tight circles. It doesn't take much longer for me to tumble over the edge, moaning Ms. Venable's name during my climax.
I open my eyes and see Ms. Venable staring at me with flushed cheeks. She clears her throat as she notices that I've opened my eyes. "Leave now," the older woman says hoarsely, and I rush towards the door, exiting the room and basically running to my own room. Once there, I smile lightly as I remember the events from just a few minutes ago.
Tonight at dinner, I can't help but notice that Ms. Venable is looking into my direction more often now than before, making me blush whenever she catches me staring at her. At the end of dinner, my underwear is completely soaked again, after watching Ms. Venable play with the handle of her cane more than usual. I get up and rush to my room, taking a quick cold shower and lying down on top my bed completely naked.
Suddenly, the door opens, and I quickly pull the covers over my body, looking startled at Ms. Venable, who's standing at the entrance of my room, her eyes wide as she takes in my appearance. She then locks the door and walks towards me, her cane clacking against the floor, which makes me shiver.
Ms. Venable comes closer and towers over me. "I want you to touch yourself again, Ms. l/n," she says, and my eyes widen.
"W-why do you w-"
"Don't question me, just do as I say!" Ms. Venable demands, sitting down on the chair next to my bed. I comply and slide my hand under the covers and between my legs, being surprised at how aroused I already am. "Let me see you," Ms. Venable says hoarsely, and I hesitantly push the covers off my body, exposing my naked body to her eyes. Goosebumps erupt on my skin as her eyes roam my body. "Go on," she says as her eyes meet mine again, and I obey.
This becomes a habit throughout the next few weeks. Ms. Venable would visit me after dinner or call me to her office, and I would pleasure myself in front of her. Today, she insisted that I come to her office. I knock and enter after I'm given the permission to do so. Ms. Venable is sitting in one of the armchairs, which are close to the fireplace, and gestures for me to take a seat in the armchair across from her and I do so. She tells me to undress, and I comply without hesitation, because I've already become accustomed to the way this goes once I'm with her.
Once I'm completely bare, I spread my legs to give her a good view and start touching myself, moans and her name rolling off my tongue in no time. After a few minutes, I speed up my movements as I feel myself getting closer to release, but then Ms. Venable says something unexpected. "Stop." I whimper but do as told while looking into her dark eyes.
"Come here," she says in a calm but demanding tone. I hesitantly get up and walk over to her, watching as she leans her cane against the side of the armchair. Once I'm in her reach, she pulls me on top of her and grins at my shocked expression. Ms. Venable takes in my body and grabs my hips with her gloved hands, the coldness of the black fingerless leather gloves and the warmth of her fingertips send shivers down my spine, and I can't help but moan quietly.
She smirks as her hands move upwards and cup my breasts gently.
"Oh God, Ms. Venable," I groan as she plays with my nipples.
"Hmm...do you like that, y/n?" she asks, the smirk still plastered on her face.
"Y-yes," I stutter.
"Yes, what?" she asks, pinching one nipple lightly.
"Y-yes, Ms. Venable," I reply, trying to keep my hips from moving against her, but I fail as she tugs lightly on my hard buds, and I buck my hips slightly against her.
Ms. Venable stops and pulls me down, connecting our lips in a hungry kiss. She pulls me closer, pressing my body tightly against hers, and bites my bottom lip, causing me to moan into her mouth. Then she slides her right hand down my body and slips it between my thighs. "Hmm...so wet for me," she purrs into my ear, and I shiver. Her finger grazes my clit, and I almost jerk in her lap. She chuckles darkly before entering me with two fingers. I moan and grip the backrest of the armchair to stabilize myself as she thrusts into me. Once she starts to rub my sensitive clit with her thumb, I'm a goner. I groan her name and come all over her fingers, panting heavily as I try to come down from my high.
Ms. Venable smirks as she lifts her hand and sucks her digits clean, moaning quietly in the process. After I’ve calmed down a little, I look into Ms. Venable's piercing eyes and chew on my bottom lip. "What are you thinking about, y/n?" Ms. Venable asks, and I debate with myself whether I should ask her or not. But I decide to take my chance and just go for it.
"M-may I pleasure you too, Ms. Venable?" I whisper.
Ms. Venable raises her eyebrow, thinking about my request. "Kneel," she says eventually, and I obey immediately, getting off her lap and lowering myself to the floor. I look up at Ms. Venable as she lifts her skirt and spreads her legs. My eyes focus on her bare, glistening core, and I have to suppress a moan at this sight. "Go on then," she demands, and I move closer to her center, kissing her thighs, which tense under my lips, before I spread her legs a little further and explore her with my tongue.
Her hands grab my hair, pulling me closer against her center. I take the hint and run my tongue through her slit before focusing on her clit. She pulls my hair lightly as I suck the sensitive bud into my mouth, causing me to moan against her. Ms. Venable moans quietly and shifts her hips a little, giving me better access.
After a few minutes, I have her moaning my name as I enter her with two fingers, curling them just right to hit all the right spots within Ms. Venable, while still basically making out with her clit. It doesn't take much longer for her to tumble over the edge, practically growling my name and digging her fingers into my scalp. I lap up all of her juices and only stop when she pulls me up by my hair. Ms. Venable looks into my eyes, her dark brown eyes filled with lust and perhaps something else. She leans in and kisses me hungrily, grabbing my butt to pull me as close as possible.
The next few weeks, Ms. Venable and I have sex so many times that I lose count. But she never takes off her dress, only lifts it up to give me room to work. And I'm curious as to why she doesn't want me to see her upper half. So I decide to ask one time, which is a bad idea, because she shuts me out completely for a couple of days. I apologize every day, until Ms. Venable loses it. She breaks down right in front of me, and yells at me to stop apologizing. "It's not you, it's me! I'm a hideous, ugly, worthless monster, y/n!" she sobs, and I rush to her side, wrapping my arms around her. "You're not! You are the most wonderful, beautiful, and smart woman I have ever seen. You're not worthless, you are the most unique person, and you're worth more than all the treasures of the whole world." Tears gather in her eyes, and she shakes her head, so I pull her even closer and stroke her cheeks gently.
"I'm in love with you, Ms. Venable. And I'm the unworthy one here. You're so far out of my league that I'm surprised you even waste your time on me," I whisper. Ms. Venable's eyes widen at my statement.
"How can you be in love with someone like me?" she asks, her voice barely audible.
"You're special, and your personality just pulls me in. I can't really explain it," I tell her, and to my surprise, she hugs me and whispers words into my ear that I never thought I would hear her say.
"I think, I may be in love with you too."
Soon she opens up about her scoliosis and her insecurity that comes along with it. She eventually shows me her back, afraid that I might never look at her again. But I just tell her how beautiful she is while caressing her spine. Wilhemina tears up, and we cuddle the rest of the night, exchanging sweet words before we fall asleep in each other's arms.
