Work Text:
A pale arm stretched down, baby-fine hairs dusting it. Long, thin fingers curled around the cylinder atop the sheets, keeping it pressed down, and Taylor whimpered.
“That’s it, baby girl, fuck your toy.”
A strangled sound left her throat, soft hips moving around the white silk encasing her bed. Her legs were pressed tight together, moving in one jerky motion.
Her tongue was pressed to the roof of her mouth, throat constricted. It felt awkward, holding the-- the fleshlight-- as she... her cheeks burned.
“You’re doing so good.” Brian said idly from the chair. He wasn’t even undressed.
Was he hard? Did it make him excited to watch her like this, all long stretches of awkward skin and fumbling with the toy as she whimpered and pressed her penis into it?
“I-- I can’t--” Oh, that was whimpering, and Brian’s soft laughter traveled through the gentle dark over to her.
Despite knowing it was just amused, just enjoying, her shoulders hunched. Her already faltering rhythm stuttered and tears formed in her eyes.
“I didn’t say you could stop, Taylor.”
“Yes, sir.” Taylor shuddered as her hips picked up their pace. Except since she was already pushed into it, she had to drag herself back out slowly, wincing at the feel. Well, panting. Wincing and panting and shivering with overstimulation.
It was too much. Too much.
“You can take it.” Brian encouraged. “One day you’ll be ready for a real cunt. Maybe Alec, hmm?”
Taylor cried out, lip wobbling as she fucked into the toy with unexpectedly fast, short thrusts. Practically humping it. It was so embarrassing. She had to hold it in place, her other hand bracing against the bed.
“Yeah, maybe our pretty boy. Get him all hot and whimpering under you, the two of you all helpless and moaning as you get lost in pleasure. I like watching two submissives kiss.”
“N-not... submissive.” Taylor squinted her eyes closed as she struggled to breathe right, every exhale warbling on a moan, and inhales marred by not-yet-sobbing-whines.
“You, or Alec? Because you definitely are, baby, but he could go either way. Or maybe you want one of the other girls?”
Taylor yelled again, the overly sensitive head dragging over silicone making her wince and fuck and wince and fuck even faster.
“Yeah, you like that idea. Which one did you think of, sweetheart? Rachel? Or Lisa?”
“N-neither.” She tried, only for her breath to shake out on a high pitched, pathetic sound. “Both.”
“Maybe I’ll let you graduate to real pussy.” Brian mused. “Do you think you’re ready yet? Or would you just disappoint them?”
Taylor burned with humiliation. Literally. Her shoulders and chest and face were all pink and on fire, glasses slipping down her nose with the sweat on her face.
Her throat tightened and tingled like she might be about to cry.
“N-not, n-n-not--” She didn’t know if she was even defending herself or not, the other half of the sentence refused to form as she got distracted with the cresting pleasure. Not quite there yet, not quite, but close enough to make her realize, shamefully, that she was going to come from this.
Would Lisa be disappointed? Taylor had gone from lasting only a few strokes to lasting entire minutes inside her toy, and her stamina had improved a little. Running helped somewhat, but sex was an entirely different monster of cardio.
“Of course, Rachel is liable to throw you down and climb on top if you disappoint her.” Brian trailed a finger down Taylor’s leg, leaving behind what felt like real sparks of hot-cold pleasure.
She wanted to be touched. Wanted a warm body. Wanted hot, wet pussy instead of the toy. It was enough to bring anyone to the verge of tears.
“She can.” Taylor ducked her head, trying to stabilize her rhythm. It hurt, it was too fast, too desperate. If she came like that she’d regret it, but trying to slow down when she was so close hurt in a different way.
“Stop.” Brian said, so idly and casual that it took a few seconds to register as a command. She whimpered again, hips pistoning three, four times before she could still them.
When Taylor was sheathed inside the fleshlight, thighs straining with the effort of not moving, Brian tisked.
“Out of the little pussy toy, you insatiable thing.” He said it as though scolding a particularly stupid dog, gentle yet exasperated, and Taylor’s eyes prickled with tears as she forced herself out of it.
Her wet and straining cock hit the cold air and she shivered, miserably naked and excited on the bed. He was looking, of course, eyes gazing over her from head to toe. Was he coming closer? Was he going to touch her!?
Taylor leaned into it, hoping, heart beating loud in her chest.
Brian gripped her chin and held her tight, forcing her to look where he wanted.
Her eyes got lost in his and he smiled, charming despite the words and darkly amused tone. Her heart fluttered.
“Put your cock back in the toy, Taylor. Slow.”
Her palm was sweaty as she pushed the fleshlight into the mattress, holding it still for her. She had to guide in with her hips alone, which felt-- clumsy. Stupid. Something about having her face gripped in that iron touch made it feel even awkwarder-- and a thousand times hotter.
The moan she gave was stuck between her teeth because she couldn't open her jaw.
After a few bumbling attempts to push in, she got her hips at the right angle and blushed hard. He’d been watching her this whole time, but watching her face from up close, holding her gaze, was so much worse!
Then she forgot to panic about that as friction pulled her in, as she sank deep with a haggard groan and squeezed her eyes shut.
When she bottomed out her cock spasmed, the head brushing against the fake-cervix or whatever shape was in there at the back of the fleshlight, and her hips jerked with tiny motions. It was too much, too sensitive. Her hips moved like they couldn't decide to push in further or pull out, her every exhale was a whimper, and the clear toy showed quite clearly the round red flesh of her balls pushed against the opening.
“So desperate for it.” Brian chuckled. Her eyes opened, blinking a lot, lashes wet with tears as he came into focus slowly. “Don’t you want to come, Taylor?”
His thumb stroked over her lip, which parted for him.
She tried to nod, knowing he’d feel it-- even if her jaw didn’t go anywhere.
“Pull out just an inch.”
Taylor was already moving before the order landed, desperate. She barely eased out before pushing back in, mouth opened as far as it could with his strong grip, and saliva starting to pool and escape.
How embarrassing. How utterly fucking--
“Beautiful.” Brian praised, voice so dark, and Taylor fucked forward in a shallow thrust, accidentally making it far too long and drawn out once she was in, desperate to stay clutched within perfect grippy plastic that wasn’t enough.
She strained to push farther, drawing it out, and each thrust took so long because of it.
Her balls kissed the soft mouth of the toy and she cried, pelvis straining to push deeper, to get more. She ground into the toy with tears finally falling down her cheeks.
“So gorgeous when you cry for me.” Brian said, like he was complimenting her blouse, in public, not like she was this desperate-humping thing making a pathetic mess of herself.
She moved her hips from side to side because she couldn’t thrash her head like she wanted, no matter how hard she tried to pull away from his hand, and the rocking motion made it worse/better, so she did it again, pushing pink into the flesh sleeve and whining.
Taylor ground against the opening so hard it hurt, her balls wincing, but she couldn’t stop, couldn’t pull away, just adopted a circular motion to try to spread the pain so it wasn’t too overwhelming. It felt like a painful massage and her throat burned as real sobs escaped, great gasping breaths that she couldn’t breathe through.
“Please.” She begged, voice hoarse with it, “Please, Brian, please, please--”
“Begging?” Brian thumbed over the corner of her mouth, through the wetness there. “You’re so pretty when you beg, too. Keep going.”
“Brian,” Taylor gasp-sobbed, but he was merciless, and her body interpreted his order in two ways. A litany of please-please-god and diriter spilled from her mouth, barely legible without the ability ot move her jaw, and her hips kept grinding so painfully into the toy.
She couldn't pull out, didn’t want to leave the hot grip, just wanted to stir her penis around in it forever, feel the cushiony hold, keeping her soft and safe and cherished and--
Taylor spilled sobbing into the plastic, buttocks clenched tight, arching into it, and face clenched tighter by Brian.
“There’s my pretty girl, there you go.” Brian murmured increasingly pleased nonsense and Taylor shuddered and trembled through spurt after spurt, crying so hard she couldn’t breathe.
Noisy, snotty sobs wracked her body, but Brian didn’t seem to care, didn’t pull back in disgust.
In fact he leaned forward and kissed her so softly, pulling her in by the fingers under her mouth.
“When you can last more than five minutes without shoving it in and keeping it there so selfishly, then we can talk about starting in on Alec. He’ll be good practice for you. Wouldn't want to disappoint the girls, do we?”
No, Taylor shook her head tiredly, agreeing. She couldn’t speak, throat a vice. She was so sweaty and limp. Her cock spasmed weakly in the fake pussy.
“That’s my girl.” He smiled boyishly again, and Taylor mustered up a tired smile back.
Then his other hand, dangerously free all this time, gripped the toy that still gripped her. Slowly, mercifully slowly, he started pumping it around her encased penis.
The overstimulation took her breath away. Tears immediately started pouring down her cheeks. She clutched at his forearms desperately, begging with her eyes.
“None of that, now.” Brian said sternly, voice a dark warning. “You know we’ve got to work on your stamina, too. It’s pathetic right now.”
She ducked her head, cowed.
He sped up the grip of the pocket pussy, ruthlessly, methodically guiding it on the wrong side of too much, until Taylor was fully hard again-- and wet, and sensitive and pink-- and pressing herself further in the bed trying to get away.
“Shh.” Brian said, hand slipping up to cup her cheek gently, thumb swiping away a tear. “You need this, baby. We’re making you better. It’ll only hurt for a little bit.”
Taylor swallowed a sob and nodded, unable to do anything about the tears that flowed or how hard she gripped his arms.
“Good girl.” He praised, as she held herself very still for it, suppressing every flinch and biting her tongue to avoid pressing back into the sheets, jerking away.
“That’s my good girl.” Brian’s voice wasn’t unaffected, and that made all the difference. He was affected by her, even the pathetic show she gave-- not good enough, never good enough. Yet.
He cared enough to fix her.
Taylor moaned, forcing the sound to be loud, enthusiastic, convincing. It only shook a little bit. It hurt, her penis wanted to cry, but she smiled tremulously and Brian looked so proud.
“Just like that.” He praised, switching up the angle. “Fuck, yeah, two more orgasms and we should be done for the night.”
Taylor swallowed heavily, eyes wide.
“Two?” She gasped, unconsciously rocking her hips into it.
“That’s right, sweetheart. I know you can do it.” Brian smiled at her, working the toy mercilessly on her shaft, and Taylor needed several squirming breaths before managing a tremulous smile back.
It was starting to feel good again, almost more than it hurt.
She nodded, smile losing its hesitancy. She could do this. She could do this. She would!
Brian smiled wider and kissed her, a sweet press of lips that quickly transformed into something messy and devouring, dirty and wet and lewd as their tongues entered the mix.
She felt used. She felt wanted, if not beautiful. Still a long ways to go, but not hopeless. Brian wouldn’t waste his time on someone hopeless.
Gritting her teeth metaphorically-- she was too busy sucking on his tongue and whimpering to do it literally-- she tensed up briefly, every muscle and nerve screaming don’t.
But Taylor had long figured out how to ignore those warnings from her body, and on the next downstroke, she forced her hips up, wincing from the wave of sensitivity that burned through her pelvis.
Brian purred approval, pulling away from the kiss to bite at her lips and jaw and kiss his way to her ear where he could murmur filthy encouragement, sounding so damn proud when she pushed past the pain to meet his strokes, to force her oversensitive dick into where it belonged.
One day it would be Rachel.
One day it would be Lisa.
She just had to get there, first. She wasn’t there yet. Oh, it was so obvious she wasn’t there yet, but she was so much better than she used to be. And she’d made so much progress, it was almost unbelievable.
It was possible. She’d get there one day.
Taylor just had to earn it.
This fic has been converted for free using AOYeet!