The Dickinson Estate

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Stop! Please!" he whined, turning his hips, trying desperately to detach from Maybell, and hide his hips from her not-so-tender ministrations.

Maybell stopped, but only to swat his bottom with the palm of her hand and take firm hold of his little nuggets pressed tight and purple like a plum. She jerked his balls upward as if it were his leash, coaxing him back into position. "We are nowhere near finished, you brat." Her nails dug into his sack like a raptor claw grasping a rodent, her grip threatening to drain the life out of them forever and forcing the wayward delinquent to come to terms at once as she repeatedly paddled him.

The control was terribly exciting and it drew a pained whimper out of him. "No! NO!" he snarled, an ounce of petulance working its way into his voice. Alexander began to struggle and push, but it seemed that Maybell knew just how to handle that sort of behavior as she yanked and squeezed like a vice. Hazel's face changed from a nurturing, almost motherly gaze to a look of disappointment and disgust as she slapped him across the face. "Don'tcha be rude to Miss Maybell now," she told him as she grabbed a tuft of his hair and yanked his head back. "Give her your ass n' say yer sorry," she told him despite his whining and pleading, landing yet another smack on his cheek.

Whatever residual fight he still had was quickly extinguished by the raking hands across his face and ass, a painful lesson to teach him that disobedience was not tolerated. The brave yet broken young man looked up into Hazel's cold eyes and found no sympathy there despite his trembling lip. His compliant butt arched high up into the air again quicker than you could say 'Bottoms-up!', raised and open, ready for further plunder. What passed for his cock trembled and squirmed in its cage, pushing lewdly (but impotently) against the bars of its jail.

"I-I-I..." tears trickled down his handsome cheeks, and he was having trouble speaking, "I-m S-sorry Miss Maybell..." he managed at last.

Maybell nodded to Hazel then turned to her bag. Alexander could hear the shuffling sounds of fabric against fabric, followed by greasy, wet noises. Hazel's plump lips spat directly on the poor boy's face as she held his head up by his hair while her other hand plugged his nose, forcing him to sound nasally and more ridiculous than usual, all for her own amusement. "Say it again ya' bitch, real sweet-like to Miss Maybell." By now the doctor was lining herself up, legs spread wide and her dress pulled up as she pressed the slick, rubbery tip of a strapon against the crack of his bottom. She rubbed it up and down the smooth crevice, then pressed the tip against his sore balls, mashing them. Her assault only continued as she smacked the thick, meaty dildo against his small cocklet and nuts, punishing and humiliating them with her superior-sized dick.

"AH-AH-H... I'm ss-s-s-sorry Missss Maybell!" Alexander called, with feeling this time. His voice was distorted by his Mistresses' efforts, sounding high and strange with his nasal passageway blocked. The poor boy's face was a mess, caked in drool, snot, tears, and now his owner's spit, adding a 'ravished' flavor to his cherubic charm.

"Please!" he stammered. Please! Please! Please! Please what? He didn't know. He just wanted the hurt and abuse to end, and didn't know where to turn or what to do. His ass was up and open as requested, and his poor balls squished and mushed lewdly around Maybell's cock, wherever she pushed, making his purple testes bloat and squirm around in their sack. If there was any doubt about his inferiority or failure as a man, Maybell was doing a good job eroding it.

"P-Please Miss Maybell! I'd love for you to f-f-fuck my butt!"

"Again!" Hazel demanded before pressing his face down into her breasts, smothering him with her womanly mounds. She gyrated her chest, her tits rocking side to side, rubbing them against his face such that his words and whines were muffled and he struggled for each inhale. Alexander replied as prompted, but the words were all but lost against Hazel's chest, which were damp with his various fluids and hot with the rush of breath, rasping pathetically against her in soft sobs. "Pls Msmbl, Fckmmmbt!"

Maybell remained calculated. She leaned over him, somewhat awkwardly, grabbing an arm and pulling it back and under him, then directed his hand to where the sizable dildo, dripping with lube, was pressed against his imprisoned dicklet. "Rest assured I shall. But first, touch," she instructed him, letting him feel the size difference, the thick veins running along the shaft of the fleshy dildo like ridges, and the small, smooth metallic sheath covering his shameful nub, her hand over his, guiding it.

"What do you feel?" Maybell asked.

He tottered atop Hazel's lap as Maybell seized his wrist and brought it back between his legs, depriving him of its stability. But for good reason, since she forced his hand to come to grips with the sheer size and girth of her faux cock, presenting it as an alternative to his own. And even though it had been months since he'd been allowed to touch his own dick, Alexander knew his own member was a pale shadow of that which the Doctor presented to him. It was thick where he was thin, long where he was small - vascular, ready for conquest. The very realization almost made him shrivel in his cage, as Hazel reluctantly freed him from her breasts

"Your cock..." he managed. "It-It's bigger than mine, Ma'am..."

She was instructive and confident as she led his hand around the dildo which gave a humiliating contrast. "Indeed it is. It's much bigger, in fact. It's a fine specimen, isn't it? Appreciate its generous girth, its length, the wonderful texture along the shaft. Far more filling and desirable than yours could ever hope to be," Maybell told him. Hazel smiled at him and kissed his forehead as the doctor continued. "It's the kind a man would be proud to have and a woman eager to please..."

"Thas right! Thas what a real dick feels like, pumpkin. Why, you should be mighty grateful to feel it," Hazel told him. Maybell brought his hand to his caged cocklet again, nearly overshadowed by the much more prominent dildo.

"Very much unlike yours, of course. Terribly small and undeveloped, and unlikely to develop much more, I'm afraid. 'Tis only good for passing water," Maybell said, her words saturated with disappointment. His member was indeed terribly small and underdeveloped, or at least that's how it felt scrunched up in its cage, quelled by hard steel. He tried to remember how it felt to be stiff and how big he was and whether he compared favorably with others. But truly, he couldn't recall, and he'd never given it much thought until now. And now he was confronted with the terrible reality, or what Maybell wished to present as reality - her cock felt enormous, well-shaped, virile and above all else normal! Not like his...

"Like I been sayin', ain't no woman gonna want that tiny thang. And if it ain't gonna do no woman no good then what businness it's got gettin' hard? So ya can play with it and spurt out a lil bit now n' then? Tsk tsk tsk, no no no darlin'. That's mighty selfish! That ain't no life and no way to make a woman happy, I tell ya. And I know you're wantin' to be a real man and find an honest woman, but that just ain't for ya hun." Hazel's exaggerated tone was emotive with mockery and reassurance, as wildly different from Miss Maybell's pedagogical tone as his small penis was from Maybell's large dildo.

"Understandably," Maybell interjected, "it's normal and healthy for your useless member to be jealous. Embrace it." She began moving his hand up and down along the shaft of his cock cage, encouraging him to stroke it without sensation. "Let it feel more than cold iron. Let it feel envy, anger, despair...this is its natural state. And when I fill you up with it so you may finally appreciate how wonderful a real cock can make a person feel, your pricklet will still long to be inside an ass as tight as yours." She gave his backside a hard slap and backed up a tad, leaving him to fondle his denied dick while she aimed the bulbous head at his tempting ass.

"MMMA'M!!" he cried out, tightening his hold on Hazel, his eyes leaping up towards her porcelain face in crisis. His entire, supple body seemed to tremble and shiver and Maybell had good reason to believe the boy's thimble was filling up nicely with rapidly deteriorating sperm.

"Tell ya what hun," Hazel said to him as she pet his chin. "You just think about havin' a big dick and fuckin' my ass with it while Miss Maybell does her thang, mmkay? Can ya do that for me?" He nodded contently. Then suddenly...

"Aaaa-Ah!" he stammered as Maybell entered him, pushing past whatever token resistance his pink sphincter thought to offer. She seemed to know just how to handle him, wielding her faux cock with skill and technique until he had no choice but to split around it, swallowing her up inch by inch with scarcely a cry. Either Hazel was doing a very good job training her boy's butt, or Alexander was born for this. His face was red and flushed still, but he was being brave, lulled by Hazel's soft words and motherly care to accept the tableaux they forced upon him.

His mind began to immerse itself in the fantasy Hazel provided, buoyed by the novelty of getting to touch[ his cock again, if only by shimmying the outside of the chastity device. It provided just enough friction to spark his imagination and let it run.

"Nnn..." he stammered, vaguely wanting to say something but nothing fruitful came to mind. How could he resist? Both of these women were so much more wise to the world than he. Alexander was just a silly boy that dreamt of being a man... of finding a woman like Hazel and taking her to bed. He stared up at her, his eyes bleary and full of water.

"I want to be bigger!" he insisted, with force, his little hand tugging at his cage, as though he might somehow transmute his own penis into the throbbing example of idealized manhood Maybell had presented him... or at least pull the cage off. He was locked up nice and tight, and seemed likely to stay that way for a very long time. "Please-" he pleaded, "I don't want to be useless. I-I want to fuck you, Ma'am. I can!"

Maybell paid little attention to his confused babbling and pressed forward, her hands holding him steady by his hips as the tip of her wet and stiff phallus met his fuckhole. She rocked it back and forth, carefully prodding him with the head to soften him up. Judging by the resistance and in spite of Hazel's regular use of his behind, he was still quite tight, and Maybell would take care not to damage his precious body. She was skilled and purposeful, her wide hips adding the slightest tad more length to each slow stroke, giving him time to adjust.

Hazel was motherly with him, wiping his wet eyes and stroking his cheek with her thumb, whispering softly to him with their faces close together. The narrative she spun for him was as disturbed as it was fantastical. "Shhh, it's okay. Ya' are fuckin' me, darlin. Can'tcha feel it? Your dick's pushin' right up against my ass, right now."

The tension soon melted away and Maybell watched as she eased the head further into the beautiful boy's body, the circular ring stretching to fit snugly around the cock, and let it rest there. They were now playing a game of good cop, bad cop with him. "Good, the head is in. Surely you can feel how much it's stretching you, much further than your cock would stretch any hole," Maybell told him.

Hazel shook her head. "Don'tcha let that bother ya now, pumpkin', just keep imaginin' ya' got a big dick like that and it's goin' in my ass, mmm yeah, it shore is! Keep on rubbin'. It feels real good, don't it? How ya' givin' it to me darlin'? Ya' got me bent over? Or ya' got me on my back with my legs all up?" Of course, all he could really feel was the invasion from behind and the constricting metal around his cock with each throb. His psyche felt as if it were being ripped in half as the women pulled his mind in different directions.

"Mmm... Bent over, ma'am..." he told her, relishing the idea. Alexander loved her ass, and wanted to imagine it pushing back against him, her doughy derriere rippling with every thrust. He inched back just a little bit, pushing himself deeper into Maybell's cock. The fantasy continued - "I'm giving it to you. H-hard. You're screaming my name, and about how big I am. I have a hold of your hair. A-And I..." his already flushed face turned just a little redder, this time from blush, "I'm going to give you a spank to make sure you behave."

Alexander closed his eyes, as though to better conjure the fantasy in his mind. Meanwhile his latter hand was tugging quick, pulling on his cage, hopelessly attempting to get his fingertips through the bars to touch his shaft. He made a cute face, tongue sweeping his lips, brow furrowed in concentration...

The doctor's eyes were fixed on the penetration as she increased depth and speed, further wrapping him around the cock. It seemed effortless for her, each thrust employing hip and ab and thigh muscles which had memorized these motions. She fucked like a man and he took it like a woman until the base of the strap-on was tapping his swollen little nuts. It drew satisfied moans out of her as the strap-on pressed into her puffy cunt lips, wet with desire for the sweet boy she was fucking. "What a tight bottom. Absolutely delicious," she said to herself before reaching beneath him, taking hold of his wrist, and guiding his hand away from the useless "stroking" of his caged cocklet. "Don't bother with that little penis, slut boy. The only one that matters here is mine," she told him as she pulled his right hand behind his back, using it as a handle to control him. Her opposite hand took hold of his left shoulder. She used his shoulder and arm to pull him back even closer as she drove the veiny dildo deeper into his butt.

"Ah- No!" Alexander cried as his hand was pulled away from his favorite toy, leaving his inadequate cock entirely unattended now, other than the unyielding sheath that held it quelled and in an obedient posture. He fought against Maybell, but only for a moment and soon she had control of him with one arm pinned behind his back and a firm grasp on his shoulder. He gasped and then groaned as Maybell urged him back, complying dutifully with an arch to his back, pushing against her momentum like he'd been taught.

Maybell had all of him now, her cock proverbially balls deep inside of his well-used ass, splitting his hemispheres right down the middle as they rolled back against her, producing a delightful jiggle with each thrust that rolled up through the fat of his ass and thighs. "Oh! Oh my god...!" Alexander sighed, his eyes glassy and dazed and unfocused. Together the two women were taking him to some new and strange place, where his sexuality could be further molded. Now he actively pushed back against Maybell, returning her thrusts in kind, excited by the soft moan she'd given him, as though the idea of female pleasure excited him, or provided positive reinforcement to his lewd acts.

Hazel continued to indulge the absurd fantasy with him. "Oh it's in me so deep darlin', fillin' me up real well! ... Ya' shorely a real man now, ain'tcha? ... Whatcha' mean pumpkin'? Can'tcha feel my ass squeezin' your dick? Gosh, it's just sooo big!" she said with a detectable insincerity. If he tried hard enough he could maybe imagine the throbbing tightness around his penis was actually Hazel's asshole milking his cock. As Miss Maybell pulled him back and up, arching his back, Hazel found more room to spread her legs wide and lift up her dress, flashing her inviting holes to the boy being taken from behind. She traced the folds of her slit with her fingers, then spread it, then rubbed her asshole before teasing her pussy again, titillating him with these forbidden fruits she fondled.

"Ma'am- MA'AM!" he cried out, struggling as though to keep his head above water, excited by the sight and smell of his Mistresses' heavenly pussy but unable to go to it, because Maybell kept a tight hold on him. Hazel remained just out of reach. "I'm- I'm- I.... AH!" and both women saw it at last, the tightening of his face, the tell-tale shiver that went down his back. Alexander' body began to loosen, and with a shudder his cock began to leak a steady stream of white goop, unassisted by any sort of contraction or explosive pressure. He simply messed the couch below. The thimble had evidently fallen away during his frantic touching, and in any event could not have contained the volume of his produce.

Hazel watched the display and rubbed her swollen clit in circles. Waves of pleasure radiated through her soft pussy as she took in the view of Maybell aggressively taking Alexander from behind, feeding his butt the dildo with power and purpose. All inhibitions had fallen away, overwhelming pleasure writ on all three faces. Maybell panted as she fucked him mercilessly, the moans and slaps of flesh creating a symphony of sex.. He could finally muster no words and was surrounded by theirs.

"That's right, little bitch. Take that dick."

"Fuck his tight ass real good!"

"You love it, don't you? Fucking slut!"

More moans and whimpers and smack, smack, smack.

Maybell pressed it in as deeply as possible and humped the base of the strapon buried in his ass. He winced.

"Your ass is going to make my pussy cum."

"Oh fuck, oh fuck..."

Hazel was soon clenching and shaking and moaning like mad, writhing on the couch in pleasure with her shapely legs still sprawled out. Maybell followed, grinding her cunt against him so strongly that she toppled him into Hazel's lap, where he found himself pressed up directly against Hazel's cunt at last. He tasted her as she came loudly, his tongue lapping up the nectar off her lips as she squeezed his head with her thighs and humped his face. Maybell humped him into her own orgasm as well, both women exploding in mutual rapture on either end of Alexander.

As their cries of joy and ecstatic spasms died down, Maybell withdrew herself, leaving his hole a gaped, wet mess, and Hazel released his head from between her thighs. He slumped to the floor, tired and well-used, with a weak smile on his face.

Just another cool spring morning at the Dickinson Estate.

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
rdoolittlerdoolittleover 2 years ago
Best story in years

This caliber of writing is rare for this site. Please write more.

AnonymousAnonymousover 2 years ago

Good writing, but no real build up as to how he got at this point or as to why he would stay in this relationship? Could he not simply move away to a different state? It feels like it's a period piece so isn't much for proof of blackmail, still seems very non con so please tag it as so thank you.

Share this Story

Similar Stories

She Claimed Him Older dominant female claims her submissive male colleague.in BDSM
Femdom Between Friends Ch. 01 Office friends discover their darkest secrets are compatible.in BDSM
Absolute Torture Tortured by my porn star dream girl and her 3 friends.in BDSM
Tamed by Meg Megan introduces me to the pleasures of being penetrated.in Anal
Praises and Pegging A dom praises her sub and makes him cum hands free!in Erotic Couplings
More Stories