Rex knelt in his schoolboy uniform with semen dripping from his temporarily sated cock. As Sylvia and Martha sat comfortably and smiled in anticipation at the coming show, Sylvia commented on how refreshing it would be to see other women dominate her son-in-law to complete submission; the three mature dominas were delighted to oblige. Rex was now ordered to strip and was leashed in readiness for his proper introduction to the ladies; the Viagra ensured his cock was already rudely stiff once more. The strict redhead was first; Rex's cock tingled as he viewed the mature woman, with a delightfully severe figure, even in her early sixties and at about 5 feet 8 inches, he knew she would have complete control over him.
"You will address me as Mistress Ruby at all times. First you will have your asshole plugged and then you will have your first caning; you will find the experience most enjoyable." Ruby sneered as she tugged his leash and the buxom brunette stepped up, with cane and shiny black butt plug. She allowed Rex a good view of the mortar shell shaped plug, twisting it before his face and making his anus tingle with fear; at its maximum girth it was twice the width of any turd he'd expelled, he knew it was cause discomfort, and so did she.
"You will address me as Mistress Abigail and will speak only when spoken to. I shall take great pleasure in plugging your anus; you will wear it at all times and will only be allowed to remove it when defecating, which will be supervised to ensure you discharge; you will be thrashed if you fail to crap. The only other occasions will be when you are treated to being used like a woman; and you will know this pleasure, and at any time your mistress allows removal." She smiled with satisfaction as she noted his horror at not even being allowed to shit without being watched over with a cane, and the thought of being 'used like a woman' made his anus tingle all the more, but perversely, made his cock stiffen. Her cunt moistened as she got deep erotic satisfaction at the fresh terror of this new prospect, and Rex could not fail to notice the swelling of her mature nipples as she continued her teasing dialogue.
"When I slip the plug in, you will know you are owned; you will know the penetration that women have to endure and you will endure it permanently. It will be a constant reminder of your submission to womanhood; it will confirm your inferiority." The mature blonde then stepped up, placed her cane on a chair and removed her tight pencil skirt to reveal long elegant legs in silky black seamed tights; the seams curving deliciously around the globes of her ass, alongside her skimpy black silk panties. Despite her advancing maturity, like the other two, her body was firm and in fine shape; Rex was now close to coming again, his cock dribbling in anticipation.
"And finally, I will be addressed at all times as Mistress Samantha; I will achieve endless enjoyment in disciplining you; many men have looked at these legs and learned that they represent the end of their former arrogance. I intend to demonstrate why immediately." Samantha remained with her back to Rex as the stern redheaded ruby made him bend with his face at Samantha's feet, his ass in the air as Abigail approached with a wicked smile. Rex whimpered as the huge plug was squeezed into his anus by the supremely dominant woman; Sylvia and Martha applauded their approval from the comfort of their viewing seats as Rex's eyes openly watered with the pain caused by the wicked intrusion, but his submissive cock bobbed and stiffened with a strange pleasure as his stretched anus fluttered and clamped tight on this new symbol of female ownership. He felt truly owned as he viewed the sexy heels of Samantha's heels and the beautiful seamed calves which accompanied them Abigail made sure it was fully home, with only the retrieving nub evident from his tortured asshole. Ruby then tugged his leash and had him kneel erect once more; the five women sneered and smiled with much satisfaction as Rex's expression of pain showed how being in an erect position increased the pressure of the plug as his cheeks closed over it. Rex now thought long and hard on his position as his anus began to enjoy the feeling of permanent and tight intrusion; his cock dribbled as any movement nursed his prostate, exciting him sexually and emphasising his total submission to women. Ruby now passed the leash to Samantha whose rear view, as she stood dominantly before him, had Rex ready to submit to any torture. Ruby announced his first punishment in her bitchy but sincere tone.
"As an introduction to all three tutors, you will worship Samantha's legs whilst caned by myself and Abigail. You will produce a good show under the cane and your new plug will assist with both your pain and enjoyment. You will lick your mess clean and will then be introduced intimately to each of us individually; Samantha will take you to her room first as she will not have had the pleasure of caning you." Rex was in heaven now, as he was ushered forward on his knees and Samantha parted her glorious mature calves slightly to accommodate his stiff and eager cock. She pulled his leash taut to ensure he knew she was instrumental in his punishment, despite not wielding a cane on this occasion, and clamped her thighs expertly about his cock, letting him know that she would determine whether he was allowed to come or not; she was a much in control of him as the other two. Rex had his wrists bound at the front, with his arms around her legs, and his shoulders nestled against the full round cheeks of her ass; he sniffed uncontrollably at her sweet feminine scent, his cock bulging between the firm calves and soft silky touch of her tights. He jerked uncontrollably as Ruby and Abigail cut the air with their canes, as they strutted dominantly in preparation for the beginning of Rex's treatment, which would ensure his complete and utter submission to all females. Five cunts moistened in readiness as Ruby announced commencement; her cunt, along with Abigail's, oozing and tingling with extra pleasure as they relished inflicting pain on a new subject for the first time. Samantha's cunt buzzed too, as she pulled the leash as taut as possible, to ensure Rex did not sag as the canes bit home. Ruby sneered with delight.
"You shall now have an introductory taste of what is to come; you are ours now." Without further ado, Ruby brought the cane down in a vicious arc; Rex tensed and his cock jutted forward exquisitely between Samantha's firm calves, and she held the leash tight and the delicious impact of the cane was heard for the first time. Rex howled with pain like a child as the red stripe blushed across his cheeks, and before his howl had died completely, the sound of Abigail's wicked delivery cut the air and enhanced the stinging pain he was already experiencing. Rex cried and screamed like a baby as his ass was severely punished by the dominant women externally, while internally his stretched anus clenched at the huge plug and tingled in sweet submissive ecstasy. The two mature women smiled with deep satisfaction as they flexed and twisted their shapely bodies in succession as they delivered stroke after stroke, reducing Rex's ass to a mass of red and purple stripes. Rex humped forward with each stroke and now through the tears, he began to feel the pleasure of submission as his cock slid deliciously between Samantha's calves as he endured the thrashing. Samantha now felt the urgency of his throbbing cock and increased the pressure of her calves slightly; his ass now numbing with the pain and the plug teasing his prostate beautifully, the pleasure afforded his cock had him wallowing in submissive ecstasy. Samantha jerked the leash.