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Confidence Is Key

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“So, what’ll it be?”

You’re not going to respond—you would rather keep your confidence then agree to something so silly. Wilbur was good with his words, making you feel emotions and imagine scenarios that you’ve never thought of or felt before. It’s scary how much of an effect he has on you. It’ll take a lot more than just a few questions to get you to beg like a dog.

Wilbur wasn’t even touching you. He was doing the bare minimum and you already desired for more. “You’re not responding… is it because we’re outside?” he asks. Yes, you both were outside. There was a possibility—a high possibility—that someone could walk out and discover what the two of you were doing. It terrified you, because all that built up pride and that high ego of yours would just fly right out the window.

You wouldn’t admit it, but you already felt like shaking. Wilbur tilts his head, smiling in amusement. “Are you nervous? Nervous that someone will find me and you together?” he went on, his hand now hovering over your clothed stomach.

Your body craved to be touched, to be handled in a way that you didn’t have the courage to say out loud. “You’re dirty. Filthy even.” Wilbur degraded, gliding his fingertips up and up until they touched your throat. The expanse of his palm enveloping your neck, fingers gripping on gently to the sides.

“I’m sure you’d like someone to find out. You’d love it if they watched.” Wilbur’s words were taking a toll on you now, because your underwear was already becoming way too wet. A harsh grip to your clothed cunt tore a gasp from your lungs, your breathing hitching.

The tips of his fingers eased up and caressed your folds, making you whimper in return. He’s aware of how wet you actually are. “Pathetic. You’re enjoying this, aren’t you?” Wilbur’s hand pulls away, and you let out a faint, shaky sigh. His grip on your neck tightened only slightly, but the pressure made you flinch. “Wil—“

“Shut up. I don’t want to hear you talk.” he interrupted. Wilbur stood there for a moment, thinking. Slowly, the hand on your neck moved up until the tips of his fingers rested at your bottom lip. You sent a glare Wilbur’s way, but that only made him smile. “In fact, I don’t want to hear you talk at all. Open.” he ordered.

You stood still, refusing to obey what he said. A dark look crossed Wilbur’s features, and he now harshly gripped at your jaw. The sudden force made you gasp, lips parting just enough for the other to shove both his middle and ring finger inside.

He pressed down on your tongue, forcing you to gag softly on his digits. You still don’t want to talk, let alone make any noise, but it’s so fucking difficult when someone actually knows what they’re doing. Wilbur knows exactly what you want, but he won’t be giving it to you at all. “Much better.” he mumbled. To be closer to you, he parts your legs with his thigh and puts pressure on the spot that you needed it the most, a choked moan leaving your throat in response.

You want to wipe that smug smirk off of Wilbur’s face, but you weren't in control now. “I bet you want me to fuck you with these fingers, make you cum until you’re just begging me to stop, right?” he asked, and you hesitantly nodded. The taller let out a low chuckle, “You’re such a slut. I’m doing bare minimum here and you already want me to fuck you?” he shamed, which had your face heat up in humiliation. Your legs were trembling, because now slowly but surely, you were melting in Wilbur’s grasp.

His fingers unexpectedly moved further into your mouth, causing you to choke and gag. Your hand gripped onto his wrist, eyes tearing up as Wilbur pressed down just a bit harder. The taller’s hand moved to grip at your ass. “Jump.” he commanded. You did just that, carefully moving your legs around his waist and locking them in place. Wilbur presses you against the wall, hips colliding with your soaked cunt. A gargled groan made its way out of your throat, the pressure driving you absolutely crazy.

You could give two fucks now, and even if that big ego of yours was gone, you want more. Oh you fucking crave it. You rock your hips forward, gaining that satisfaction of pleasure once again, but Wilbur lets out a sigh in disappointment. “Look at you. Grinding against me like some fucking dog. Is that what you are? Huh?” he asks, which only fuels him on further. You whined pathetically, which made Wilbur smile.

“I bet if I fucked you right now, everyone in a two mile radius would know. You’re so loud.” he muttered, which made you huff. Wilbur knows he shouldn’t give into such temptations, because fucking you now would end this all to quickly.

Carefully, he removes your legs from his waist, you now leaning against the wall with a sexually frustrated glare now aimed at the taller. Wilbur glanced around, now just making sure that there was no way that they could be seen for this next part.

Slowly, he pulled his fingers out of your mouth. He decided that edging you with his fingers would suffice. “The faster you get out of that skirt, the faster you get my fingers.” Surprisingly, the second he said that, you began to unzip and pull down your skirt and underwear.

You were now sheepish, drained of that confidence you once had. It was like you were some sort of teenager, so excited to get the best and first head of your life. The change in temperature made you hiss quietly, embarrassed at how you were now nude in public. Sure, there might not be anyone around now, but it made you nervous.

Wilbur turned you around and pinned you to the wall, which made you grunt. His spit soaked fingers trailed across your hole to tease you, which certainly made you moan in surprise. “You’re such a whore. Feels like you’ve been fucked before. What a shame.” he mumbled, now pushing his fingers in without warning. A shaky breath left you as he moved in, hands balling up into fists. Wilbur manages to spread his fingers apart, which forces a moan out of you. “Fuck—fuck.” you pant, to which Wilbur chuckles at.

“You like that?” he asks, nearing your ear as he moves up against your side. You lean your head back, eyebrows pinched together in pleasure. You can’t find the words to say how good it felt to finally be somewhat full again. So, you groaned shakily in response. Wilbur started to pump them in and out at a steady pace, occasionally shoving them into you to get a reaction out of you. It surely did get him a reaction. “Fuck! Wilbur—please… please.” you suddenly begged, face now all red.

“God, listen to you. You’re so goddamn loud.” he muttered, reaching up with his free hand to shove his fingers in your mouth again. You moaned against them, pushing your hips back on his hand to get more out of him. “You have to be quiet though… what if someone were to walk out here right now?” he teased, making sure to keep the tips of his fingers near that sweet spot within you.

The second that they brushed over that sensitive spot, your whole body jolted. You shakily whined. “Fuck me… Fuck me please.” you begged through Wilbur’s fingers, which made him shove them further into your mouth. “I never said you could talk.” Wilbur lectured, which only made you moan more.

You wouldn’t be allowed to cum, no matter how many times you begged and whined. “Tell me when you’re close.” he said, enunciating on the last word as he slid another finger inside. “Fuck… you’re making it difficult for me to control myself.” he mumbled against your ear. “I bet you want me to knock you up, hm? Breed you like the good whore you are for me?” he asked, a whimper leaving you in response. That did sound really good, and you’re not opposed to it.

Your nails dug into your palms at the new finger added, now trying your best to keep quiet. It was tough, considering that Wilbur hit every perfect spot. Your legs felt like jelly, repositioning your stance every few seconds because it was beginning to become difficult to stand.

Wilbur yanked you back towards his chest, you now shaking and quivering as he pumped his fingers at a rapid rate. “This cunt is mine. Understand?” you bob your head in agreement, willing to do anything he says to have the permission to cum.

Wilbur could feel that you were growing tense, growing so close to that impending release—all until he stopped. You almost sobbed, pushing your tongue up against Wilbur’s fingers so you could talk. “No no, please! Wilbur please. It hurts, please let me cum.” you begged, but Wilbur only chuckled. “Sluts like you don’t deserve to cum.” he replied, to which you whimpered at.

The taller slowly pulled his fingers out, now making you upset that you weren't able to finish. Your eyes were glossed over, jaw clenched. “I’ll be good.” you added on to try and convince him, but Wilbur already moved away. Kindly, he helped you pull up your skirt and underwear, teasingly zipping the back up.

“Meet me here at four tomorrow. You’ll cum on my cock then.” he proposed, ignoring your little pleads. You felt so exposed and shy from doing this out in public, but now that you’ve gone through it once, you’re certain you’ll have the confidence to do it again.

Maybe you won’t be so shy next time.