Gina and the Penitent Blowjob

As much as his internal drive demanded it, Caleb still managed enough mercy and sense to not try to ram through her near-sealed snatch. Tightness was the only lure, and the likely screaming that would follow was enough to back off.

She’s probably a virgin. This thought didn’t tempt Caleb in the slightest. He had already popped one cherry in his lifetime, and Maria, that lucky bachelorette, had rewarded him with blood, screams, and a dramatic breakup over it, wiping clean all Caleb’s fetishes of being a woman’s first. Focusing on that memory—and imagining how much worse it would be for Gina—he resolved to be the bigger man.

Not wanting to risk the table’s collapse, he grabbed Gina by the waist and pulled her over its edge, forcing her to stand while still in his grip. I can’t make her think or feel certain ways, that much is clear, but if everything I do becomes something she made me do, then any plan I explain would be… Such a plan was being crudely put together as Caleb scanned her body… and her mouth.

“I want to come,” Caleb started… and then his cock **** him to add, “inside you.”

Her eyes, fluttering from bliss, snapped back to full panic. “W-What?!”

“You’re going to suck me off,” he carefully whispered as he brought his face close to hers. He hadn’t noticed until now how red her face had gotten, but his own cheeks burned as he grew excited. “If you don’t get me to come fast enough, though I’m going to… eh, I mean, then you’re going to make me fuck you in the ass.”

Gina had no response, save letting her mouth hang open. As he eyed that pretty hole, she snapped it shut as if in self-defense.

Caleb did his damndest to **** a frown, to feign any kind of lack of delight as his cock raged against his pants. “This is how you chose to make it up to me… the fact that you’re **** me, I mean. But the best you could think of was just **** me more.” He shook his head in feigned dismay. “I have **** or power here.”

“I-I… I’m so… I feel so sorry, I…” Tears welled in her eyes as Caleb finally let her go and started to undo his belt.

Holy shit, she’s really going to walk out of here believing it, too! Now there’s no way she’ll report what happened here, right? Caleb wanted more security on that front before he dicked this clueless woman. “Neither of us will ever speak of this again, me because of your… power over me, and you to avoid being arrested.”

She cried in earnest now as the emotions warred in her mind of guilt and shame. Caleb was startled, but he did his best to rationalize it as just being her buying the B.S. story. Of course he wasn’t being **** here—quite the contrary—and she’d forgive herself in time.

But within Gina, the turmoil was far worse than what Caleb anticipated. She had proven herself an absolute monster the moment she found someone she could toy with the way she had Caleb. What did that say about her? What depravities would she reach through him? More, what did it even mean that she wanted to be punished with anal if she didn’t suck him off fast enough? Her mind worked that one over as his pants opened and the hem of his underwear was soon pinned down by…

… by the largest penis Gina had ever seen in her short career of awkward blowjobs.

Caleb was not huge, not by the standards of porn Caleb had watched or by the erotica Gina had read, but he was a girthy eight inches, enough to earn complaints if wielded crudely. It was more than enough to make Gina losing her anal virginity a truly awful punishment here.

Punishment. It locked into place in Gina’s mind as her mental foray ended on one, logical explanation. It was the only thing that made sense.

This was self-flagellation with the meatiest whip she could find. Where did she grow this need for penile penance? Was it guilt for what she’d done to Caleb? Was it her procrastination in getting back to the project sitting idle in the forgotten laptops behind her? Was it for something broader, like her general outlook and approach to life?

Whatever it was, she sobbed knowing she deserved it. She was a **** now, and in her twisted **** mind she made a mockery of her redemption by using Caleb to do it. Gina felt she was a monster, irredeemable and ever-consuming.

“I’m so sorry-!” She worried Caleb with the exclamation—how soundproof was the room the other way, he wondered—but Caleb’s worries melted slightly as she dove to her knees and put her slim mouth on the head of his dick, sobs and all.

He tasted like sweat and soap, and he swelled slightly in her lips, but Gina was determined to finish this cruelty quickly before she made him escalate to fucking her ass. It would hurt her, and that was all she deserved, but it would also be another terrible degradation of this poor stranger she was imprisoning here. Gina could not embrace this monster inside her; she had to be stopped. Desperately, frightfully, she struggled to impale her head on the offered meat.

Caleb, unprepared for this eagerness, let his eyes roll before he groped blindly for a nearby chair. Plopping himself down while holding her head, he finally let go of the tension in his limbs as his plot succeeded more spectacularly than he ever envisioned. I didn’t even have to… **** it in, holy shit, she ain’t… bad- holy shit. Caleb reveled in the feeling of her gagging on and squeezing his dick as she **** herself down to **** herself with his length. Her tonsils and narrow little airway didn’t unfold to truly deepthroat him, but he was striking the back of her throat into a pocket that felt built for the head of his manhood. He felt her teeth hold back while her tongue hardened and pressed up to massage the underside of his organ, and her lips and throat did their best to inhale and suction him in whenever she pulled back slightly. She only pulled back mere millimeters before she thrust him back into her mouth, causing her to **** audibly, each time the involuntary cough or gag squeezing the head of him. Saliva visibly drooled from the stretched corners of her lips as tears welled in determined, sad eyes.

She was good… maybe too good. As Caleb let the sight and sensation fully absorb into his pleasure center, he forgot to actually try and hold back. The man was a hair trigger if he didn’t think about traffic or sunburns, and it was hard to grab the reins now that she was going to town, gagging herself until he almost worried she’d puke onto his lap. Caleb had never gotten to try anal before, and the blowjob was just supposed to be an excuse for free lube. Now he was really at risk of blasting his biggest load of the day into her stomach.