Rose's Dolly Pt. 02

Dolly sighed. "Oh, but I don't think I can, though," she said, in a high bratty whine.

"I know you can, if you apply yourself," said Miss Nail, in a firm but encouraging voice. "If you study hard."

"Hm," Dolly replied. "I've been studying you hard." She put her hand on Miss Nail's hand on the desk, running a finger along the back of her hand, up to her knuckle.

Despite herself, a smirk was tugging at the corner of Miss Nail's mouth. (Dylan knew that smirk was genuine, the finger stroke wasn't in the script, and he seemed to have taken Rose by surprise with it. For a split second their eyes met, Rose shot Dylan an unmistakable look of pride and lust.)

But Miss Nail quickly pulled her hand away from Dolly's touch. "What are you talking about, Dolly?"

"Oh, I've seen how you stare at me, Miss Nail. I know you want me."

Miss Nail shook her head. She turned her face away from Dolly to stare at the floor. Her hand went up to nervously rub her cheek. "I think, uh, I think you're imagining things Dolly."

"Oh, I'm sure." Dolly grinned. (A real grin; Dylan knew Rose was acting, but after all the time he'd spent being dominated by her, he couldn't help enjoying the image of her squirming at his advances. Even if it was all a performance, the feeling of power over her was absolutely intoxicating.) "I know all about your secret by the way," he said, and he put a finger on her chin, tilting her head up to look her in the eye. (Another touch he'd added; Rose gasped when he did it and he wasn't sure if that was performance or not.) Dolly's voice dropped to a whisper. "I know all about your cock."

Miss Nail seemed shocked. "How did you find out?"

"That's my secret," Dolly said, still grinning. "Well," and she lifted her skirt to reveal her own cock, "not my only secret." Another giggle.

Miss Nail stared at the cock, conflicted look of lust on her face. She turned away again, biting on her hand. "I can't do this..."

Dolly put a hand on her shoulder. "Have you ever been with a girl like me before? A girl like you..."

Miss Nail sighed wistfully. "Not since I was your age."

"Hm." Dolly put a leg over Miss Nail's legs and sat on her lap straddling her. "Bet you want to again..." She reached behind Miss Nail's head and undid her bun; her blonde hair spilled down, and Dolly greedily ran her hands through it. (Another adlib by Dylan. God, in a weird way this whole scenario was more like what he'd originally wanted with Rose from the first time he'd seen her. He remembered seeing her towering over all the other girls at the party and thinking, I'd like to see her underneath me, her head tilted up toward me. And, God, he couldn't help himself, even if he had a girlfriend, even if he was going to have to take Rose's cock, even if he didn't like being in the skirt and makeup, the feeling of being in control of the situation, Rose of all people putty in his hands, driving a girl mad with lust while she resisted giving into his advances, and still pushing, still pushing... he hadn't felt like this since before he met her.)

Miss Nail bit her lower lip, staring deep into Dolly's eyes. Cautiously, gingerly, the teacher chanced to put her hands on the sides of Dolly's torso and, once contact was made, grabbed her body greedily, running her hands up and down Dolly's body. "Oh God," Miss Nail said, "oh, I shouldn't do this."

"Why not?" Dolly grinned down at her. "Tell you what, I'll ride your cock, but only if you promise to give me a passing grade." Another giggle (it was alarming, Dylan thought, how good he was at these girly giggles). "You don't need to give me an A, trust me, no one expects that from me. Just as long as I get a D."

Miss Nail looked up, longing, agonized. Dolly gave a little thrust, jabbing her now rock-hard cock against Miss Nail's belly. She gasped at that. Dolly moved her face in, getting close to Miss Nail's lips, as if to kiss her, then as her lips extended to meet Dolly's, she pulled her head back. (This, Dylan realized after he did it, was a move he'd stolen from Rose herself. That first night, before Dylan knew Rose had a cock, he'd told her "Fuck, I want you so bad," and moved in for a kiss, and Rose had just pulled her head away and said, "Be careful what you wish for." Good advice, he thought ruefully, but in the moment, God, it had driven him crazy, made him even more determined to have her. Only natural that it would have a similar effect on Miss Nail...)

"So? What do you say?" Dolly asked, running a finger under her chin.

Miss Nail breathed heavily. Rose, Dylan thought, really was an extraordinary actress. You could actually see the exact moment where Miss Nail finally gave into the temptation, just from a minute change in facial expression.

"Oh, I'm going to give you a D alright," Miss Nail said at last, an unguarded grin spreading across her face. She roughly grabbed Dolly by the back of the hair and pulled her face toward hers.

The kiss was wild, mutually aggressive, their tongues battling for supremacy, Rose clearly hungry to dominate, but Dylan keen to hold onto his newfound sense of power. Rose's hands ran up and down Dylan's back; Dylan, in turn, unbuttoned Rose's blouse, reaching in to fondle her breasts... as his hands moved toward her nipples, she pulled her mouth away from his to hiss, "Be real fucking gentle with them, I'm not joking."

Dylan nodded; very gingerly, very lightly, he caressed the nipples. Even this sensation seemed to be overwhelmingly intense for her, her exhalations were desperate, shuddering. Putty in my hands, Dylan thought. He gave them the briefest little tweak...

"AH! Alright, you're done," she growled, swatting his hands away. "It's time for you to fulfill your end of the bargain you little slut." She opened a drawer on the desk to pull out a small bottle of lube.

"Now, why does a teacher have that in her desk?" Dolly asked, teasingly.

"What, are you complaining?" Rose smirked. "Alright, get off me for a sec." Dylan nodded and scrambled to get up. Rose pulled her skirt and panties down, kicking them off her feet, then squeezed some lube into her hand and worked it onto her cock, stroking up and down, fluidly twisting her hand all around to get the whole shaft covered. She offered Dylan the bottle; he pulled the skirt down and grabbed the bottle, putting a little on his hand and smearing it around the outside of his hole. Rose put up a beckoning finger.

Moment of truth. Huh. He had gotten into the play leading up to it, couldn't deny that, but now that they were here he felt weird about the prospect of, like, actually riding her cock, actually taking in the active role of his own sodomization. He hesitated.

Rose, seeming annoyed, grabbed his wrist to tug him closer. He swallowed. Well, it was going to happen, probably less painful to be on top. He put his leg over Rose's legs, his ass hovering in the air over her cock. Still had some trepidation. "Hey," he said gingerly, "you'll let me take it in at my own pace, right?"

She sucked in air sharply. Dylan could feel the frustration emanating off of her. But when she opened her mouth, she just said, "Sure."

Dylan lowered his ass so that her cock was up against the outside of his sphincter. Still, he found it difficult to move past this point.

Rose raised an eyebrow at him. "Ooh, you really prefer to ride it facing me, huh?"

"Yeah, I don't know," he spent a moment searching for words. Probably, he shouldn't admit this to her, but, "I guess, if I'm gonna have to take a cock, I'd rather get to look at you."

Some emotion flickered across Rose's face at that, though what he couldn't quite identify. She blinked and the emotion was gone. "Alright, back into character Dolly," she said, and she put a hand on his shoulder, not pushing him down onto her cock exactly, but clearly poised to do so.

He started descending. The tip of her cock pushed into his asshole, beginning to stretch it. He gasped. So did she.

"Ohhh, you ride cocks like this all the time, don't you Dolly," she moaned.

"Ah! Uh, yeah..." he felt sheepish again. The mere sensation of his sphincter being stretched, all lubed up, right now felt... tolerable? Nah, fuck that, it felt kind of good. Slowly, slowly, he kept lowering himself, until the whole head was in, then a bit of the shaft. It was sensitive, yeah, but everything was so slippery and he was able to adjust to it and... he could do this.

Rose was biting her lower lip again. "Mmm, so shy about it? In all my other classes, boys talk about you, you know. Talk about how they've all had a turn with slutty Dolly."

He mind raced for something to say. They were past the point where the script ended, he wasn't sure how to keep being this absurd character. It didn't help that he was still focused on this huge cock that he was letting fill him up. God it really did just keep getting thicker, all the way down... He gave a little head shake. "They're all lying, of course," he tried.

"Heh, I'm sure." Her eyes flashed wickedly at him for an instant, and then with the hand on his shoulder she shoved him down on her cock until it was buried all the way inside him.

A rough sensation, to be sure, but when he made a sharp high little "Ah!" noise, he could help thinking he sounded a little bit... delighted? It sounded, if he was being honest, like the kind of noise he'd hoped to hear that girl make that time he'd shoved his cock up her ass...

Rose clearly seemed to enjoy the sound. "Hmmm, that's the sound a real cockslut makes when you shove a dick up her ass, isn't it?" She thrust up into Dylan. "Isn't it?!"

"Ahh! Uhhh," again, Dylan was struggling for words, thoughts were difficult in the face of the sensation of Rose's cock filling him up. "Maybe," he settled on, "I wouldn't know, I'm a good... girl." God he felt dirty. Even in pretending not to be a cockslut, he was still pretending to be a girl. Disgraceful.

Wait, no, fuck, he wasn't pretending not to be a cockslut, he really wasn't. His character was the one pretending.

"Hrrrgh, I'm sure," Rose growled. "Hey, 'good girl', just one thing: make sure you don't cum on me, okay? These are my work clothes, after all, I can't be seen in the school covered in a student's cum."

"Hah! Don't worry, I won't." Being honest, he preferred not to cum from playing the submissive, it still ate at him that Rose had squeezed a couple orgasms out of him in the past.

"Hmm, good girl," and Dylan's cock throbbed, very distinctly, at those words. He was getting to be really embarrassed by his reactions to this. "Now, ride my cock."

He started off awkwardly bouncing up and down on her cock, and while Rose seemed to enjoy that well enough, it was pretty uncomfortable, stretching his hole excessively on the descent, and high effort besides, difficult to get a steady rhythm going. He eventually found himself adapting to more of a grinding motion, gyrating his hips back and forth on her cock. This was considerably less uncomfortable. Actually...

Well, actually, he had to admit, it was starting to feel pretty good. He could feel her hardness grinding against his prostate, could feel little droplets of precum dribbling out of his cock. Rose seemed to be enjoying herself too; she let out a long, appreciative low growl and roughly grabbed the sides of his ass.

"Hmmm, now you're starting to sound like a good little slut," she murmured.

God, was he? He wasn't paying attention to the sounds he was making, too lost in the moment to be aware of himself like that. Bad sign. He was giving himself to depravity. Being used was one thing, still emasculating, but at least he wasn't the one doing it to himself. This though... he felt he was being corrupted.

"Hey," Rose's voice knocked him out of his thoughts, "I wanna play with your cock. You promise you won't cum on me if I stroke you, Dolly?"

"Ye- AH!" Her lubed hand found his cock, gave it a quick stroke. "Yeah, I won't cum..."

He rarely used lube to masturbate, he always forgot how silky smooth, heavenly wet the sensation was. And the combination of the hand on his cock with the sensation of grinding back and forth on the cock up his ass... it was a more intense sexual stimulation than he was used to, it threatened to consume him entirely. Soon her hand didn't even need to move, he was thrusting his cock hard into her still hand as he ground harder and harder on the beast inside him, the two sensations, the genital pleasure and the anal pleasure, were melding into one, this insane itch he had to keep scratching.

It's funny, at the beginning he really had fully intended to not cum from this, but at some point he turned a corner, gave himself to the inevitability of it, without really choosing he found himself pushing, pushing toward that final peak...

"AH! AHHHHH!" His eyes closed, his mouth opened wide, he threw his head back, and he just let the seed burst out of him, shooting all over Rose's torso...

Wait, he wasn't supposed to do that, right?

He opened his eyes. Rose was looking up at him with this incandescent look of rage, unspeaking.

He winced. "Sorry?"

A moment passed, "You BITCH!"

She threw Dylan onto the desk, hard; he lay there on his back with his legs in the air for a second, wincing from the sharp pain of impact, and then-

"Ah! You're hurting me," he squeaked. Rose had driven her cock deep into his tender hole, much too fast.

"Good," she growled, hands grabbing two fistfulls of his hair, twisting it painfully. "Oh, you little skank, you little hussy, I can't believe I trusted you." As she ranted, she kept dealing him long, deep blows, the sensation was torture on his raw, sore hole.

"Stop," he begged, starting to sob.

"You should have stopped yourself from cumming, shouldn't you you dumb little slut?" she snarled. "You do realize I don't have a change of clothes, right, you little bitch? I'm all covered in your cum, I can't walk out of here like this and keep my job. Ohhh, I'm ruined, ruined you hear me? So," she gave him this truly unhinged grin, and her hands moved down to the collar of Dylan's blouse, "I'm gonna ruin you too. Everyone's gonna see what a depraved little whore you are," and she started tugging hard on the sides of the blouse, popping the buttons off until it was all the way open. She then grasped at the waist of the skirt and, with a deep grunt of effort, ripped the fabric apart. Wild fury in her eyes, she ran her hands all over his exposed flesh, starting with his thighs then moving up his torso to linger on his nipples, which she grabbed and twisted painfully, using them to hold his body in place while she roughly fucked into him.

"Ow! Ow! Please..." The tears were streaming down his face now.

"Heh heh, c'mon Dolly, you got off, it's only fair I should get off as well, don't you think? Ohhh, you took everything from me, but I'm going to get a fucking orgasm out of this. And hey, if I have to walk out of here covered in cum, well, it's only fair that you walk out of here like that too, isn't it?" He said nothing, she grabbed his jaw. "ISN'T IT?"

"Y-yes..." he nodded vaguely.

"Heh," she gave his face a smack and slid her hand down his torso to his cock. "You're still so fucking hard, you know that Dolly?"

He hadn't realized that, all the other sensations she was inflicting on him were so much more salient, but the second her hand touched his cock he felt it, he was achingly hard. God, he didn't like this, why did his cock? Why did every awful thing she did to him just arouse him?

She began playing with his cock, and almost immediately he could hear a change in noises he was making, from pain to, well, pleasure. Yes, his ass still hurt a lot from her pummeling him, but the hand on his cock felt good, and it seemed to be sufficient to transform the whole experience into an odd sort of pleasure. God, he felt so ashamed, so gross to be enjoying this.

"St- stop," he mumbled feebly.

"Heh, doesn't sound like you mean it," she grinned. "Hey, maybe I'll squeeze some more cum out of you, get it all over you this time instead of me. Then I can just bury my load deep in your guts. How does that sound?"

"Nooo," he moaned, "Don't make me cum, not like this..." but he could tell he was getting closer.

"Heh heh, dumb little slut, you can't resist it," she said. Her voice had now softened to more a purr than a growl. Her hand and her cock kept pushing him closer and closer. "You can't resist me," she added, smug grin on her face. "So cum for me you little whore," and she slammed her cock into him hard and yelled, "I SAID CUM FOR ME!"

And with that hard thrust the semen began spraying from his cock, splashing all over his torso and chest. "Ah! Ahhhhahahah..." he felt ashamed, defeated, so dirty that his very body seemed to obey her commands, but goddamn, even through all the pain and degradation it felt so unbearably good to cum with her cock up his ass, his hole tightening convulsively as the waves of ecstasy wracked his battered body.

But he knew, couldn't forget, what was coming next. Of course when the orgasm ended, his hole and his cock would be freshly raw, tender, sensitive. And of course that wasn't going to stop her. As the last few drops of cum dribbled from his cock, the tempo of her thrusting quickened, she was fucking him harder, more brutally. He winced, letting out a sustained high whining noise.

"Mmm, cute," she said with a sadistic grin on her face. "Hey, check this out," and her hand squeezed his newly sensitive cock, hard, while her other hand moved to start rubbing her dry palm back and forth on the top of the cockhead, dealing him a friction burn on the tip of his cock.

Dylan's mouth was open wide now, voicelessly screaming. His body tensed, his fingers gripped the sides of the desk tightly. Eventually he found it in him to say, "Stop, stop!"

"Mmmm, say it again," she purred.

"STOP IT STOP IT PLEASE I CAN'T TAKE THIS!"

"Haaah, music to my fuckin' ears," she moaned, and then, "Oh! OhhhHHHHH FUCK YES!"

Her mouth opened wide, she threw her head back, her cock throbbed wildly as she rammed deep inside him. He knew that her semen was pouring into his guts, and if her seed could make him more of a sissy... He didn't want to think about it, didn't want to think at all, didn't want to be in this body anymore.

Her hands, at least, lost their grip on his cock, he looked up and could see her hands hovering near his crotch, shaking. Her whole body was shaking, actually, her breathing ragged, shallow. Soon she slumped back into the chair behind the desk, still shaking, as the last couple droplets of cum spurted uselessly from her still-hard cock. She managed a deep breath, which seemed to calm the shaking somewhat, but burst into stunned laughter on the exhalation.

"That was..." she said, disbelieving grin etched onto her face. She seemed to remember herself, slid the desk open to grab a hair tie. She began tying her hair back into a bun. "Ahem, that was very good Dolly," she said, suddenly all clipped and teacherly again. "Almost good enough to be worth getting fired." She stood up and walked toward the front of the desk, grabbing a fistfull of Dylan's hair.

"Ow!"

She looked down at him gravely. "Almost. Have fun walking home like that you little hussy."

Miss Nail gave Dolly's hair one last tousle, and walked out of frame. Rose stepped behind the camera to press some buttons. She gave a satisfied sounding sigh. "Seriously, though, that was fucking incredible," she said, grinning widely at him.

Dylan just lay there in the cum and tattered clothes, unable to find the strength to move. "Th- thanks," he managed. He hated himself for it, but seeing how pleased he'd made her made him feel good. Still, he felt unbearably dirty.

"Uh, sorry for cumming on your clothes," he muttered.

Rose blinked. "Huh? Oh, sweetheart, that was just a bit, I don't actually care, I'll either get them dry cleaned or I won't, you know?"