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.