Caleb’s Been Broke

Human contact outside family and work was growing rare for Caleb, excluding online groups. The value of human touch was difficult to overstate, particularly as to those intimate, fleeting moments Caleb hadn’t appreciated until they were distant memories of what he had once enjoyed. Caleb’s thoughts on this void in his life were not so refined at this moment, though, and they went instead focused on the struggle between his desire to bend the nerd over the table and his fear of reprisal.

He settled somewhere in the middle: gentle escalation.

He took hold of one of the laptops and gently moved it towards the center of the table, dragging the cables softly across the laminated surface to create the hum that slowly widened Gina’s eyes and wrinkled her brow. “I… I guess I can just work on the front end, for now.”

But soon he was dragging the other laptop away from her, again to the center of the table. She sat at a blank workspace on the giant table, her bag hanging from her chair and her eyes looking longingly at the laptops she clearly needed. “I… I should gather my thoughts, of course, or even… yes, I’ll meditate on the… the…”

Her words slowly trailed off as Caleb walked around and behind her… and just gently laid his hands on her shoulders.

She looked, felt, so small now. This perspective was shared by both parties, but each trembled for very different reasons. Caution pulled the reins back on Caleb and kept his hands there on her shoulders, softly squeezing and massaging as he contemplated the rough texture of her bomber jacket, thick on top of the thick turtleneck and revealing, with a firm squeeze, the petite frame of her. If I can do this…

“Ah… I did need a massage… I’ve been so stressed with the final exams coming up…” Her words were unsure and deliberate, hinting at resistance until that fight melted away.

“Then you want to get this jacket off, right?” Caleb quietly asked.

“E-Eh? N… I mean, that does make… sense-ah!” She exclaimed as Caleb’s hands slipped into the collar of her jacket and began to tug it apart, urging her to comply. She leaned forward as he peeled the giant, olive leather away and left her with…

Well, why stop here?

“Direct contact is important for a massage.”

“D-Direct-?!” Again her surprise caught her off-guard as Caleb, with fire in his face and veins, advanced ever forward. His hands gripped the bottom hem of her turtleneck and, before she could get her glasses off, pulled up. The almost glowing white skin underneath was comical compared to her healthy-colored face, and Caleb didn’t even try to avoid ”accidentally” lifting away her bra. Inch by inch, she was stripped until the whole wad of cloth came over her head and, with her glasses in the mix, lifted from her body.

Finally freed from this brief, confused struggle, Gina spun around, light olive hands covering her tiny white mounds, as she squinted in confusion at the man stripping her nude. “W-Why would I… B-But it makes sense, but I’ve never been n-naked in front of a boy, so please… don’t… return my glasses. I can’t stand seeing you look at me right now?” The explanations she came up with were so dumb it sounded like even she was starting to realize it, but with a firm nod she seemed back onboard.

Caleb, with a turtleneck, bra, and pair of glasses in his hand, just stared in awe. I can do anything. Caleb did not pause for a moral qualm or an ethical dilemma, he thought to none of his female friends to empathize with their trauma, and he certainly did not lose his raging hard-on as he reckoned with what stood before him.

I can do everything. Gentle escalation proved a fleeting plan.

Unceremoniously dumping her belongings on the floor, glasses cushioned by the cloth as it landed on the jacket, Caleb’s hands reached for Gina. She recoiled in clear discomfort, but paused as she did so… or maybe it was just the table behind her leaving nowhere to go. Caleb’s hands grabbed her wrists and then spread out, letting Caleb lord over as he looked upon her tiny, puffy nipples hardening in the cool air. Her face was… complicated, but settled on a pout as she grumbled, “This is… the worst massage I’ve ever had.”

“It’ll get way…” Calm, Caleb. “… more intense soon.”

“I can’t believe I signed up for this… I mean you already have my time, and the best way I can think to make you spend it is to strip me down for a massage?”

“Was it a massage?” he softly inquired as he let go of her left wrist… and dared teasing fingers to streak paths along the side of her left breast. She shivered at this perverse tickle. “Didn’t you want… something more?”

“Absolutely not,” she firmly rejected, “and come to think of it, I don’t even like massages, I don’t even know why I made you-”

Caleb smiled, and then he grabbed her chin and **** his mouth onto hers. There was a brief struggle, a surprised cry as she felt his tongue take the opportunity of her opening mouth to lick it inside--the flavor of a fruity drink, Caleb guessed, stuck to his tongue--before she slowly stopped her vain efforts against "her" own wishes for this perverse kiss. Pure confusion reigned, now, and as her body twitched with questions he didn't let her ask, Gina offered little more resistance as he felt along the hem of her skirt for a button or zipper keeping it on her.

Finally, she pulled her head back enough to evade his probing mouth as she gasped for air and answers. “W-Why?!”

Caleb didn't bother answering anymore; she'd do it for herself in a few seconds, after all, and he had just found and undone her skirt's button.

“W-Why would I kiss you before I graduated?!”

A strange metric, but Caleb rolled with it. “Better question is: why did you make me kiss you?”

She blinked in horror at that, and that was perhaps the distraction he needed to scootch her away from the desk long enough to let her skirt fall to her ankles. She bent down to grab it back up, but Caleb quickly straightened her back up as he pressed against her. Caleb hadn't gotten any of his clothes off yet, but he longed to. “I... I made you kiss... me...?”

Was it so ludicrous that her condition would finally break?

“I... I'm so sorry, I didn't... I don't even want... I'm sorry!” Her eyes were glassy as she looked up at me with something between guilt and... pity?

Holy shit... she thinks she's forcing herself on me right now. Caleb had no intention to correct her, given the only alternative explanation. Suppressing a grin, he whispered, “I can't believe you're going to **** me to... have sex with you, right here on this table.”

“I-I'm not! Please, I would never- eep!” Her trembling, pale body reached for Caleb's wrist as he hooked his thumbs under the hems of her panties and spats in one aggressive grab, but Caleb's blood was too hot to stop now. The spats and panties slid down her ill-kempt legs, each one stubbly from a need for a shave, until Caleb was face-to-muff with an unkempt bush.

No girl Caleb had ever been with--not that he had many--had ever dared be with him, or even be at risk of being intimate with him, without maintenance of some variety. Then and there, he couldn't recall ever seeing a woman in-person with so much as a hairy shin, so this was very new for the 31-year-old. European? Does this count as European? Her pits--visible as she flailed--seemed shaved, so he decided it was not.

“N-No, I-I have a medical condition--I would never! I could never... I don't know what's wrong with me...” Tears welled in her eyes in earnest, now.

Wait a minute... Medical condition? This raised alarms for the man who had his share of STD scares, and he didn't dodge all of those just to get one from a student at his job. “What's your medical condition?” he demanded as he wrenched her foot out of her sneaker and through the discarded cloth on the floor, nearly knocking her over with his roughness. He didn't bother to contemplate the fact that, for all his caution, he was still undressing her.

“W-Whoa, I... why would I ask that aloud, here, in front of you?!”

“You're concerned about giving me whatever you've got,” Caleb offered simply, wondering what this conversation even sounded like to the bizarre girl.

“Y-You can't get vaginismus, why would I even think something so stupid-?!”

Caleb didn't know what "vagistmas" was, but it did sound like a holiday, and that resonated with Caleb who found this crazy gift in the middle of a shitty workday. In barely a minute's time, he had stripped this loony young woman bare in the middle of a windowless room bereft of cameras or witnesses. For all her complaints, he suspected his next attempts to arouse her would be met with another rationalization of why she wanted this and, perhaps, even make her a willing participant. Caleb wasn't looking to make the girl suffer, after all... but as his dick continued to bark orders, her hesitation and panic became less and less reasons for him to slow down.

Which is why he picked her up by her butt, one cheek in each hand, and cradled her briefly before sitting her down on the table, her legs **** to spread to either side of him. If she felt small before, she now felt like she was in the grip of a giant.

With his hands spreading her knees briefly so he could tuck between them, he then dove for her near-flat mounds to give each a gentle squeeze and pinch of the nipples to get her compliance. It didn't quite work, but him pushing her onto her back sure did. Satisfied, he let his hands trail down her flat stomach, past the tiny pale hairs of the space between her belly and hairy mound, and let his fingers slide down to again spread her thighs and let him have a face-to-face meeting with whatever lay below. She tried to sit up, but again he **** her down... as she must have wanted, so she finally complied with a confused groan.

Shoving his thumbs into the hairy muff, he groped for the lips he knew hid there and worked to spread them. Embarrassing and degrading as it might be, he was going to take a good look around for any signs of this "vagismusk" or whatever it... was...

... Jesus, how tight is this girl? He tried to spread her labia further, but somehow he found resistance... or else she was just so damn tight that all he could see were the fleshy sides of the vagina and, between them, a spot of black that was the tightly-closed space between. Caleb slathered up his left forefinger and gave it a testing prod, feeling more like the world's worst gynecologist than the sexy beast he imagined he would be by the end of this... but sure enough, even his single finger found resistance. He pushed-

“”AAFHdfdhhhfh!” Gina had covered her own mouth in reaction to her scream, and Caleb was startled by the noise.

He peeked over her pubic mound like a mechanic investigating a clang. “What happened?!”

“Why... why am I torturing myself like this?!” she sobbed.

“You want to say what's... wrong, out loud.” Her condition didn't let him suggest things, but maybe she'd find the self-pep-talk persuasive?

Luckily, she did... sort of. “I-I can't... even if I want to, I can't...”

Christ, she's so tight though, but with enough lube- wait, wait. Think, Caleb! What's she trying to say? He almost put his wet finger back in his mouth until he remembered he wasn't sure this girl was clean, yet. “Maybe if you... explained it in detail, out loud, you'd understand what you're trying to do here.” I'm a fucking genius.

Whimpering, she whined, “I can't be penetrated... it hurts too much, it's just not possible... I... I was too scared to do the treatments, so is this me... trying to **** it? I... I'm such an idiot! You can't just screw away vaginismus!”

The dots were slowly connecting for Caleb... but just to be sure, he kept her pinned to the table with one hand on her pubic mound and the other fishing out his phone. After three attempts by Google to help him out, all while his thumb continued to probe her clit in a likely vain attempt to get her horny anyways, he eventually found the correct spelling of the condition.

He ignored her growing, gentle gasps as he toyed with her this way, focused on his phone as he was. Alright... vaginismus... involuntary tensing or contracting... muscle spasms occur when... oh... ooooh. Caleb groaned in frustration as he looked back at the impenetrable Seal of Solomon winking at him from between the trembling, pale thighs under his care. Fuck... since when could girls be too tight to fuck?!

“Ah... ah...” It took him a moment to realize her whining had turn into soft, panting moans... and looking again, although her pussy remained visibly impenetrable, he did see some building moisture--

Her vagina spat at him, spraying him right in his eyes. “Ack-!”

“Aah~” Her body bucked and shook as he held her down... and after Caleb issued the necessary prayers to hope the pussy juice on his face was not poisonous, he realized what was occurring.

I... I was just playing with her clit, dude. Did she really just...? I mean is that possible? Is she really that sensitive, too? She was quickly rising above her station on the ol' 1-10 scale.

“Oh my... oh my God,” she moaned, “did I just... did I just...?” Apparently she was no less surprised.

“You like this,” he triumphantly declared.

“This is like... the best vibrator... you're real, and... and since I'm making you... I want everything you're... doing... but it's wrong, I shouldn't **** you... to... hah~?!”

He didn't stop molesting her, of course, and now he was testing her clit while gently tickling her inner-thigh and the spaces just outside her pussy.

Alright, Caleb... so she's definitely, absolutely about this weird mental condition. She's also an easy lay. She's also impossible to fuck without hurting her... well, at least in her... He glanced down at her tiny butt, looked back at her gasping mouth... and acknowledged he had options.

But the misogynist in his heart glanced again at the forbidding snatch... perhaps the tightest pussy he would ever find. Painfully tight, unbearably tight... for her, yes. But how bad would it be for him?

But how bad would it be for her?

But how good would it be for him?

Looking at her shaking body as he continued to build up her next orgasm, it was hard not to feel he was due at least a... test run. Besides... what if it helped?

Something in Caleb knew it would not help... but his dick didn't know that, and it was making some really excellent points about the horny nerd spread out in front of him and at his mercy.