Rose's Dolly Pt. 06

"This Nicky, he ever say he loves you?" Dylan asked.

"I don't remember," she muttered.

"Well, you'd probably remember if he had," Dylan said, "given how hot you'd find it."

"Heh. Then yeah, probably not." She grinned. "I remember you saying you loved me."

"I believe I said I loved being your sissy slut," Dylan grumbled, "and I only said that under duress."

"Yeah..." her hand on his shoulder started stroking his arm again, "was it true though?"

"No," he grunted.

She leaned down and planted a wet kiss on his face. He inhaled sharply from excitement when she did that, which she clearly noticed. "Liar," she said into his ear.

"Believe what you want," Dylan said, keeping his tone neutral.

Rose's hand moved up from his shoulder to tousle his hair. "Looking pretty shaggy up there," she said, an amused tinge in her voice. "You've been growing your hair out."

"Yep."

"Any reason why?" She had this enormous eager grin on her face.

"Because you told me to," he muttered.

"Aww," God she was looking smug now. "And why would you do what I told you even after I let you go?"

"I dunno," he grunted, then, "Ah!"

Rose had given his hair a sharp yank, tilting his head up to look into her eyes. "I think you do know," she hissed.

He said nothing.

She gave his hair a painful twist. "I've been on your mind, haven't I? You've been wanting me to take you back."

He shook his head and said, "No!"

"No?" A quiet voice, but her grip on his hair was ferocious, he thought she might yank a chunk of his hair out.

"Ow, ow, ow, okay, fine, you've been on my mind," he blurted out, "I think I've lost the ability to get off to thoughts of other girls."

Goddammit.

"Reeeeeaaaally?" At this point she released his hair, mercifully, but a second later she jumped on top of him, pinning his body under hers on the wood of the porch. "I gotta say Dolly," she said, her enormous grin filling his field of vision, "that's the sweetest thing anyone's told me in a long time."

"Look," he said somewhat crossly, "I wasn't trying to be sweet, just describing reality."

"Aww, you don't gotta be so shy about it, Dolly." She planted a flurry of kisses all over his cheek and neck. Despite himself, his face broke out into a grin at that, which she soon noticed, grabbing either side of his grinning face with her hands and going, "Ohhhh, look at that face! You missed me bad, huh Dolly?"

He exhaled. He hesitated. In a small voice, "Yeah."

"Hmmm, tell you what, how about we go upstairs and I make the fantasies you've been having all summer a reality, huh?"

Sigh. "I don't wanna say yes. I don't know... it still feels weird to, like, agree to it."

"Yeah?" She let out a playful little growl, "And what if you don't have a choice, huh? What if I'm gonna do what I want with you regardless?"

"Well," a wry grin on his face now, "I guess if I don't have a choice it doesn't matter what I do, huh?" So he wrapped his arms around her body and gave her a tight squeeze, just because he wanted to.

She let out a surprised "Oh!" at that. That felt good. He gave her a kiss on the forehead. That felt good too.

Indescribably good. It hit him as he lay there with her on top of him with his arms around her, he'd never let himself just enjoy her before. And it felt great but... if he went upstairs with her, he knew she was going to hurt him. But maybe, just maybe, she'd be willing to give him something he wanted.

"Hey Rose?"

"Yeah Dolly?"

"You know what I might be willing to agree to?"

She had a curious eager look on her face. "What?"

"Fucking the girl I've been obsessed with up the ass," he said.

Ooh, the change that came over her when he said that was distinct. Her enthusiasm seemed to evaporate, she looked away from him. "Oh yeah?"

"Yeah, I don't know. I spent a lot of time fantasizing about that. Probably more time than I spent thinking about the stuff you actually did, if I'm being honest."

She snorted. "Wishful thinking, huh?" She still wasn't looking at him.

"Hey," he chanced to put his hand on the back of her head, and ran it through her hair. "You wanna make me happy, right baby?"

It was interesting watching the series of emotions that crossed Rose's face. There was this deep ominous irritation, a blink and her eyes were enormous, almost pleading, as if silently begging him to stop asking for this. She looked away again, then a smirk tugged at the edge of mouth before she turned her gaze back toward him with this wicked fire burning in her eyes.

"Oh sure, 'baby'. But if I'm gonna let you penetrate me I have some... conditions."

Dylan could feel the fear start to rise in him. "Y-yeah?"

"First," she said, grinning down at him, "I'm gonna have to be on top. Second, I need you to eat my asshole for a while before I let you put your dick in me."

"I'm fine with those," he said. Hell, that actually sounded pretty great.

"And third," she paused to suck in air, "I'm gonna need you in handcuffs while we do it."

He blinked at her a few times. "Ooh, okay, not sure about that..."

"Aw, why not?"

"You're gonna take advantage of me being in handcuffs, aren't you? Do something I wouldn't like."

"Who, me? Never." She winked at him.

"Well, why do you want me in handcuffs then?"

She shrugged. "I dunno, if I'm gonna let you penetrate me it's very important to me to not lose control. Oh, you want me to feel safe, don't you Dolly?"

"Stop calling me Dolly," he grumbled.

"Hmmm," she ran a hand through his hair, "when you walked up to the porch, were you expecting me to stop calling you Dolly?"

"Guess not," he muttered.

"But you came over anyway. You know what I am, Dolly, so why resist?" She planted a kiss on his forehead. "Tell you what, if you let me handcuff you, I promise I'll let you put your cock up my ass, okay? No taking it back."

He sighed. At this point, hearing her speak in that warm, coaxing voice she was using, feeling the weight of her body against his, his now achingly hard cock grinding against her belly, her hand stroking his hair... he wanted to give in, give himself to her, but his every nerve ending remembered how bad it would hurt, how degrading it would be.

"Will you promise not to, like, fuck my ass or hurt me?" he asked.

She snorted. "Dolly sweetheart, I want it to mean something when I say 'promise.'" He frowned at that, so she went on, "Look, if you want, I can pretend I'm not gonna do anything to hurt you, and you can pretend you believe me. But I mean, if you turn this down, when do you think you're gonna get a chance at my ass again? Hey, maybe your dick is so amazing I'll be satisfied just riding it. It's technically not impossible. And," here she gripped his hair tightly, nails of her other hand digging into his back, her crotch grinding hard against his, he could feel her cock through her jeans, enormous and rock hard, "I'm sure you realize that if you say no, that doesn't mean you get away. It just means you don't get to fuck me. So, what do you say Dolly?"

He lay there tense beneath her. Of course she got scary again, she always got scary. He hated the idea of submitting to her desires, but there really was no way out. He relaxed his body. "Cuff me then."

"Hmmm," a delighted, hungry growl. "Good girl," followed by a sharp bite on the cheek.

"Ow! Stop calling me a girl."

"Oh Dolly, you came crawling back to your dickgirl mistress, you don't get to pretend you have any manhood left." She pulled herself off Dylan's body and grabbed his hand. "Come with me."

So, soon enough, he was upstairs in Rose's room, peeling off his briefs, when he felt her hand give his ass a sharp smack, then grab his cheek.

"Hmmmm, you've been keeping up with your ass exercises, huh?"

"Yep," he said, feeling tense.

"I can tell!" She ran her hand over to grab his other cheek. "I love it. God, your dick is gonna have to be fucking mind melting to keep me out of your ass tonight."

That made him nervous, but he tried to play it cool. "Well, you haven't experienced my dick yet, so," he shrugged.

"Oooh, she's cocky, huh?" Rose had this delighted grin on her face. "Alright bitch," she held up a pair of handcuffs, by all appearances real ones, heavy silvery metal that clinked together as she dangled them in front of him, holding them by the chain between them, "lay down on the bed. It's lock up time."

She'd actually bought a bed frame since the last time he'd been in here, he thought as he lay down, reddish wood with a spindle headboard. She got on the bed, positioned herself so she was kneeling with a knee on each side of his torso, and she leaned over him to lock his left hand in a cuff, thread the chain behind one of the spindles of the headboard, and then lock his right hand up.

"I've got you now," she purred, and she leaned down to give his nose a nibble.

He grinned at that despite himself, but he was feeling this strange cocktail of anxious emotion, fear and anticipation and this dizzy nervous excitement. The feeling stretched over every inch of his skin; he knew intellectually it was warm in here, but he felt cold, body covered in goosebumps.

It must have been visible on his face, because Rose grabbed his chin and, in a taunting voice, said, "Aww, why so scared, huh? What did I ever do to you?"

That got another smile out of him. "You want a list?"

"Well," she moved his hands down to rest on the sides of his torso a bit below his armpits, "you know what always relaxes me?"

"What?"

"Tickle torture!" and suddenly her fingers were dancing all over his body and up into his armpits, making him laugh and writhe uncontrollably.

"Stop, stop!" he managed through the laughter.

"Hmmm, poor baby. You live such a hard life, you know that?" Mercifully, she pulled her fingers off him. "So Dolly, are you ready for my ass on your face?"

He nodded, "Yes please!" He had to admit, he was in a pretty good mood right now.

"Ooh, 'yes please', huh?" Rose got off of him and started getting her jeans off. No underwear underneath, huh. "So, my Dolly is a degenerate ass eater, is that it? You ever dream of being smothered by a pair of ass cheeks?"

"Sometimes," he admitted. "It's not that weird a fantasy, I don't think."

She snorted. "Well hey, maybe I'll forget to let you breathe under there and you'll get your wish, huh?" She climbed back up on the bed so her ass was hovering over his face, big and round, strong muscles slightly tensed due to being held up. Slowly, she began lowering it onto his face. "Open wide."

He opened his mouth and stuck his tongue out.

Rose let out a high little, "Ooh!" noise when his tongue made contact with her hole. Soon after, his face was enveloped between her buttocks. God, he wished his hands were free to feel them. Rose sat the entire weight of her body on his head; heavy, but he liked the sensation. He worked away at her hole, feeling the tight sphincter twitch and loosen from the stimulation of his tongue, pushing his tongue deeper and deeper into her as she opened up to him. And as he ate her hole, he heard her breathing get more excited, felt her rubbing her hard cock back and forth along his chest, felt her hands run greedily up and down his torso until they landed on his nipples...

"Mmph!"

"Ohhh, I can't help myself sweetie," Rose said, and gave his nipples another hard tweak.

"Mmnnh!"

"God, they're so pink and hard right now. Well, they're not the only thing that's hard..." she moved her hand down to grab at Dylan's tumescent cock.

"Mmmhmmm..." A much more pleasurable sensation.

"Ooh you like that huh?" She leaned down and took the head of his cock into her mouth.

As her lips descended his shaft, taking more of his length into the warm wet world of her mouth, he squirmed beneath her in ecstasy, letting out his desperate uneven little breaths into the flesh of her bottom.

"Ha, I'm driving you crazy, huh?" She gave his cock another quick lick, driving him to a shuddering gasp. "Alright, I think both surfaces are plenty wet, let's do this."

She lifted her ass off his face and turned around on the bed so she was facing him, and moved down so that she was squatting over his cock. "It's been a while since I did this, so I'm gonna take it slow."

"Of course you get to take it in slow," Dylan grumbled.

"Of course," said Rose, "I've seen firsthand how much damage it can do to your ass if you don't."

"Ha ha," Dylan said, and then, "Ahh!" The tip of his cock had pushed past the opening of her sphincter.

"Ooh, that feel good huh?" She was slowly, slowly lowering herself onto him, a focused expression on her face, mouth turned into a slight frown, as if she couldn't quite tell if she was enjoying herself or not.

"Yeah," he breathed. He was impatient, so he thrust his cock upward into her, burying an additional inch inside her in a single stroke.

She let out a surprised "Ah!" noise at that; swiftly afterward, her hand reached up to wrap around his throat, squeezing to cut off the air.

"Dolly, sweetie," she said through clenched teeth, "I'm gonna need you to let me take this in at my own pace, okay?" He nodded desperately, so she released his throat.

Deep gasping breaths to replenish the air in his lungs. He didn't want to cross her again, but... the feel of her hole, squeezing so tight around every inch of his shaft that it touched, it required every bit of restraint he had to not thrust into her again, he burned to be balls deep in her.

She was still hovering about an inch above the base of his cock, face scrunched up. "Mmmm, it kinda hurts baby," she muttered, then her eyes lit up. "Lemme try something..."

Her hands reached up to twist his nipples hard; she looked down at him with this malicious lust as his face contorted from the pain. "Ooh yeah, that helps baby," and she descended so that his cock was at last buried. "Ooh... ooooooh..." she shifted her weight on him, gyrating her hips, slowly at first, still visibly adjusting to the cock being in her, then faster, seeming to enjoy the sensation, mouth starting to open, breathing picking up. Her hands had mercifully left his nipples to run up and down his belly, and he was free to just bask in the grip of her hole on his cock, the sight of her magnificent body moving back and forth on him. Her own cock was rock hard and rubbing on his belly as she rode him, and he had to admit that he found that sensation erotic as well. Stupid futa cum, he thought, made him a damn faggot, but... why not just enjoy it?

She looked down at him. "How do you feel, Dolly?"

"Amazing," he gasped.

"Hmm. I gotta stay, this isn't bad for me either. Hey," she began leaning her face down toward him, "kiss me."

He gave his mouth to hers; her tongue filled his mouth, exploring, probing, taking ownership of him.

After a moment she pulled her mouth away from his to whisper in his ear, "You know you've got ass-breath right?"

He laughed. "And whose fault is that?"

"Yours, for eating ass. Dirty little freak..." A nibble on his earlobe and she pulled herself upright again, rocking on his dick with renewed urgency.

He looked up at her, helplessly enraptured by her. "Oh, God, I wish I could touch you," he moaned.

"Oh yeah?" Little grin on her face. "If your hands were free, would you play with my cock?"

He looked down at it, rubbing against him, leaking precum onto his chest. It felt weird to think, but it was kind of... beautiful? "Y-yeah," he confessed.

"Yeah?" Oh, she was intrigued now. "You been thinking about my cock? Craving it?"

"Sometimes," he said, but that didn't feel honest. "Often."

"Hmmm, it's been thinking about you too, baby," she murmured. "You been wearing sissy clothes?"

"No," he breathed, "but I've been- Ah! I've been looking at sissy clothes and imagining wearing them with you..."

"Wow..." That grin. He wanted to be mad at how smug she was, but right now, as she rode his cock he was just so happy to have put that grin on her face. "And here I thought I was doing a favor letting you go. I should've kept seeing you, huh?"

"Ohhh God, I wanted you Rose." He didn't want to be making these confessions, but he'd had so much bottled up inside him, so much he'd never admit to anyone else, so much he didn't plan on admitting to her. There was a joy in unburdening his heart, throwing open the door and letting all the secrets out, right now he'd probably tell her anything.

"Hmmmmm. Call me Mistress."

"Mistress." Felt good to say. "My mistress... it tore me up to see you with that other sissyboy, I wanna be your sissyboy." He paused to catch his breath. Damn, he'd really just said that and meant it. He laughed nervously. "God, your cum did a number on me, huh? I'm not the same person I was before you..."

"Hmm, guess not." She looked down at him, this proud imperious expression of ownership. Her finger reached for the tip of her cock and scooped up a drop of precum. "Eat it," she said, and he did, sucking it off her finger. Salty.

"Oh God, you're still dosing me, huh?" he moaned, drunk with lust.

"What are you talking about?"

"Your precum. You're still corrupting me with it. Sissifying me." He looked right into her eyes. "Making me yours."

She blinked. She seemed confused, but after a moment her eyes lit up with recognition. "Oh! That thing I said about futa cum making you into a sissy. Oh, sweetheart, I made that up."

"What?" Didn't make sense, no that couldn't be. "But... I'm different now."

"Hmmm that's the funny thing," a wicked glint in her eye now, "you're the same you've always been. This was always inside you Dolly."

"No..." He didn't have an excuse. He'd needed that excuse. "No, no no... get off me!"

"Rrrrgh." An angry growl now. "What, are you gonna pretend you don't feel all those things now? Nah, Dolly, you want me right here, don't lie."

"I said GET OFF!" he cried out desperately, and started struggling underneath her.

"Hey!" She roughly caught his hair with both hands, leaning down to stare angrily into his eyes. "You asked for this, yeah? So I don't care what you say, what bullshit you're about to throw at me about how you don't want me. I'm gonna ride your cock until you cum and then... I'm gonna do whatever the fuck I want with you."

"No, no, it's not right," he muttered, shaking his head, "it's not me, I can't be like this."

"Hnnn..." she still seemed angry, but she released his hair and sat up again, determinedly bouncing on his cock with a furious intensity. "Well the good news is you don't gotta do anything except lay there and let me use you."

"Just stop, please..." It felt too good, he knew he was getting closer.

"Hmmm, you know the funny thing is I was kinda lukewarm on letting you fuck me before, but now that you're begging me to stop all I wanna do is force you to cum inside me."

"Ah! AHhhh!" The first spurts of semen shot out of him. A rapturous sensation, but with it came a wave of shame.

"Yeah, like that," and she grinned smugly down at him, drinking in the sight of his wide mouthed O face.

Soon enough his orgasm had ended, but Rose was still riding his cock with the same intensity. Unbearable on his newly sensitive cock. It was funny, his response now really threw into sharp relief how fake his resistance a second ago had been. Now it really hurt, now he was thrashing under her, not even capable of words of resistance, just these urgent staccato little whines, face scrunched up into a wince.

"Awww, don't like it anymore?" He shook his head. "Poor baby... you know I actually believe you now, right?" Mercifully, she lifted her ass off his cock, but just as quickly got herself down on the bed so her face was near his cock and took the head into her mouth.

"Hah! Argh, okay..."

Intense suction, unbearable, torture, making exaggerated "Mmm! Mmm!" noises as she did it, as her eyes burned into him, watching his pained expression with a rapt fascination. After a moment she pulled away. "Is that better?"