Serena knew exactly what she was doing. The dominatrix was well aware that Billy was beginning to get sexually excited by this new world she was introducing him to. She understood the consequences of his actions, even though he hadn't. It was not her intent to cause him physical harm, but a good scare would do wonders for his behavior. She enjoyed his fast tongue working on her stubbled vulva; this one had potential and she was going to enjoy actualizing it. Billy suddently felt the first sharp pain as his swelling cock encountered the sharp wires that made up the cock cage. He gasped and his tongue stopped lapping up the moisture that had begun dripping from the old woman's cunt.

He felt her weight increasing as she pressed down harder on his face, making it more difficult for him to breathe. The combination of pain and the panic caused by the growing lack of air had the desired effect and his cock began to shrink back into the confines of the cage. Serena's face broke into a knowing smile as she felt his tongue beginning to once again maneuver itself into one of her special places. This one was learning; perhaps it was time for a little reward for his obedience to her wishes.

"Would my little sissy boy like to stick his nasty tongue into Serena's hot and nasty brownie? I'll bet the sissy boy would love to taste Mistress Serena's asshole, wouldn't he?" She added emphasis to her rhetorical questions by adjusting her body so that his nose was buried in the cleft formed by her plump ass cheeks. Billy's cock once more hardened and this time the contact was longer and even more painful as his mind fought the battle of self preservation versus the forbidden fruit that was within his reach.

Serena was astonished at the rapidity with which he was adjusting to her dominance over him. However she was a wise woman and realized that someone as unformed as this teenaged boy could not be trusted just because he showed a few signs of acting like an adult. He had to be punished and humiliated further so that he would become even more malleable to her wishes and training.

Her decision caused her to once more create a situation where Billy's attention was drawn away from his focus on her and devoted more toward his own well-being. It was an easy matter to shift her body ever so slightly and making breathing most difficult for him. She could not resist wiggling her well rounded bottom back and forth over the boy's face, teasing him unmercifully as she allowed him tiny wiffs of air before suffocating him some more. His cock responded in kind, growing and shrinking to suit the degree of pain and pleasure he was receiving.

Finally Serena looked over to where Lucy was standing, her eyes taking in every move that the dominatrix was making. "I think that Billy needs to be milked some more, or he's going to hurt himself." Lucy nodded in agreement, part of her wishing that Serena had let things go a bit further. It would have been interesting to see how much pain Billy would have allowed himself to endure in order to satisfy her good friend. Then she shook her head to clear it; had things gone further his cock would have been cut in any number of places. She drew the line at such a result.

Serena unhooked her bra and freed her smallish pear shaped breasts. Billy's eyes homed in on the sagging bags of fat and skin, his cock hardening and pressing up against the cage. Lucy was absolutely amazed at his behavior. Here he was surrounded by girls and women, including herself, who were quite well endowed in that department and Billy hardly seemed to notice. Yet the sight of his old woman's sagging breasts was enough to give him an erection. How strange was this?

Lucy hadn't figured out that the key to taming her grandson lay in his secret wish to be dominated by a strong woman, one who he feared and loved at the same time. These desires were hidden deep within his subconscious and were just beginning to surface as the result of Serena's presence. Dominance and submission were the things that this woman was very familiar with; it was her livelihood and her life, all rolled into one.

Billy's cock sprang free of the wire cage and began to stiffen almost immediately. Serena settled herself besides the boy and offered him her tits as Lucy began stroking this hard cock. "I want you to kiss them and make my nipples get nice and hard. Then I want you to lick them all over while your granny tries to get you off. I don't want you to come until I say you can. Now get busy and pay attention to my titties." For many long minutes Billy's mouth was clamped to Serena's tits, suckling them like he was a baby nursing. Lucy was awe struck at what Serena was making him do. It was as if he was regressing, going back to a time when his whole world revolved around his mother's teats to fed and comfort him as he adjusted to this new environment.

Lucy kept stroking her grandson's stiff cock, trying to bring him off. Normally he would have exploded by now, especially after having his cock caged like that. She looked over at Serena who gave her a knowing smile and mouthed the words, "keep going" to her. Lucy cupped the boy's balls in one hand and gave the top of his dick a series of swift short strokes. That approach had never failed her in the past no matter what the size of the dick or the age of its owner. It took three tries before Billy's cock shot an enormous load of hot thick cream all over her hand and up onto her face and chest. She was glad she had stripped down as soon as Serena began working on Billy. At least that blast of boy goo hadn't ruined her clothing.

Serena's angry response to this occurance took Lucy by surprise. The dominatrix pulled her tits away and muttered that he hadn't asked her permission if he could come. "I am not used to being disobeyed, especially by a sissy boy! I am about to teach you a lesson that you will never forget. Lucy help me get this disobedient sissy boy into the bathroom. We have work to do so that this kind of behavior can never happen again." For some odd reason Lucy felt her cunt beginning to get wet with anticipation of what was in store for her grandson. She could hardly wait to see what terrible punishments her friend would mete out to Billy.

The young stud muffin offered no resistance when he was momentarily freed from his bonds. He obeyed Serena's orders to put his hands behind his back so they could be cuffed. He winced when the dominatrix's hand closed round his scrotum and gave his balls a hard squeeze. "When we are through with you those balls will be the size of beebees and probably be hiding somewhere inside your abdomen. By then you will even look like a little sissy boy with your shriveled little weenie dangling down like a limp piece of meat, all raw and sore."

Lucy was astonished at the boy's reaction to Serena's threats; his cock was hardening. She had evidently tapped into another hidden part of his personality. Lucy's cunt was positively dripping as she fantasized about what she might do to this tamed teen once Serena had turned him over to her tender mercies. In her mind's eye he was naked and securely restrained to his bed which was soaked with his cum and the juices of all the women of the family who were enjoying his tongue and cock regardless of the strain it put on his body, now considerably leaner from all the sexual activity he was being forced to engage in with them and their friends, who now where a legion.

Once inside the bathroom Serena and Lucy busied themselves preparing the first ice water enema that Billy would take. The boy just stood there watching the two naked women mixing the ice cubes in with the cold water from the tap, filling the large red rubber bag until it bulged. He had a tremendous erection by the time Serena had him bend over at the waist as he stood before the tub. She arched her eyebrows in the direction of Lucy and smiled as she readied the nozzle, which would not be lubricated. This was a punishment enema despite his sexual excitement at the prospect of taking it.

Just before she jammed the long black plastic nozzle between his cheeks, Serena slapped his butt and remarked, "Look at how big the sissy boy's dick has gotten. I'll bet he's dreaming that he's eight years-old again and his mommy is going to give him a nice warm, sudsy enema to make his poor tummy all well again. I think she must have played wih his little pee-pee to take his mind off of the discomfort when his poor tummy got so full and those nasty cramps began to hurt his little tummy real bad."

As Serena mimicked the breathless voice of some brain dead drudge of a mother preparing to get her little fantasies satisfied by this kinky method, Billy's cock turned into a bar of high-strength steel, almost vibrating; it was that rigid. Lucy made an O with her lips pushing out from her face, and Serena nodded her approval. Lucy settled her naked body on the edge of the tub and reached for her grandson's super stiff cock, ready to begin sucking it lovingly as his intestines started filling with this icy purge.

Serena pushed the nozzle deep into the boy's asshole, bringing a grunt then a gasp as the dry length of hard plastic pressed past his sphincter and entered his rectum. Lucy captured his balls in her hands and wrapped her mouth around the head of his dick just as the first rush of frigid water entered his colon. His naked body shivered from the cold that began spreading out from his rectal area. Lucy's cheeks hollowed and bulged as she applied suction to his cock to keep it from shrinking as his body temperature grudgingly fell. Her hands gently caressed his balls as they shrank. She heard the slap of Serena's palm against the lower portion of Billy' pale cheeks that were beginning to pebble from the chill.

As Lucy continued to keep her grandson's cock in its erect state, Serena was toying with the boy as well, raking her fingernails across his nipples that were soon like two stones sticking from his chest. She ran her nails across the lower portion of his belly, very close to where Lucy's mouth was working.

"I wonder what used to go on in here when this sissy boy was younger and his mommy would fill his little belly up until he thought he would burst. I wonder if she did more than just hold the nozzle, perhaps she played with his little weenie to get his mind off all those nasty cramps. Maybe she did more than that. Maybe she kissed the head of his little pee-pee or perhaps she licked the drops of precum that kept dribbling out from the tip. I know the type. These are the kind that turn their boys into monsters that don't know any better because mommy was too selfish."

Lucy could not believe her ears. Her daughter, the mother of little Billy, may have molested him when he was younger and turned him into this uncaring aggressor that had utterly no respect for women, at least not until Serena had come upon the scene. As these thoughts ran through her mind she continued to suck and lick the boy's cock, bringing him closer to an ejaculation, but still in control of the situation. Serena leaned down and whispered for her to keep him on the edge and do what was necessary to prevent him from coming until she allowed him to.

Lucy's hands began to apply a steady and growing pressure on his shrinking balls, bringing a gasp of pain from him. This sign was all she needed to let her know that she could indeed control him from getting off until Serena allowed it. Billy was about to have a crash course in obedience, and Lucy was already scheming for a way to take over his training and the benefits that would accrue from being in this position of authority over this youthful force of nature.

By the time the contents of the red rubber bag had been transferred to his intestines, Billy's belly was round and full, pressing against Lucy's forehead as she continued to suck his cock but not enough to where it would explode. He grunted and his cock twitched in her mouth when Serena yanked the nozzle from his asshole and slammed a bung into his gaping hole to seal up his bloated body. "Now my little sissy boy, you'll hold this until I decide to let it out. In the meantime I'll play with your little weenie just like your mother used to do, but you will not come until I say you may. If you disobey me his time I will keep you plugged for an hour and all during that time I'll take the crop to that little weenie of yours until it's nice and fat and worth my time to make it shoot off again."

It was with a great deal of reluctance that Lucy let Billy's stiff shaft escape from her mouth. Now she used her hands to keep it hard, but not so hard that it would twitch. Serna joined in at this point and teased his balls with her nails and on occasion would squeeze the head of his cock until it started to throb. This would be the signal for Lucy to squash his balls until that big length of boy-meat calmed down. Somehow Billy managed to retain his composure sufficiently to finally cause Serena to announce that he could now come and she wanted to see a gusher shooting from the tip of his dick.

Unfortunately for the boy, she had one last trick to play on her victim. She signaled Lucy to squeeze his balls as hard as she could when she saw Serena nod. Lucy had to make room so that the dominatrix could take control of Billy's cock and jack it furiously to bring him to the moment that he had been trying to achieve for over an hour. Then she nodded and Lucy clamped his pulsating balls just as they were about to trigger off a stream of cum that had been swirling around within them for what seemed to be an eternity. Billy let out a scream of agony mixed with frustration as the wave of semen that should be rushing to exit into the air was stopped by a wall of terrible pain from the fierce and unending pressure that his grandmother was applying to his sore balls. Billy could not deal for long with this situation and he proceeded to faint dead away, collapsing onto his grandmother.

They rolled Billy into the tub, yanked out the bung and let him foul himself as he lay in a pool of his own wastes. After hosing him off they got the boy back on his feet and prepared another enema for him to take as he mumbled and sobbed in frustration and humiliation. Lucy eagerly suctioned his cock back to full hardness before Serena released another wave of chilled water into his roiling intestines.

This time as she inserted the nozzle, she did it almost in slow motion, pushing it into him slow inch by slow inch, pausing to move it from side to side and teasing his prostate as it was quickly pushed in and out of his asshole before settling back into the original position. Then the process was repeated once more. All the while Lucy enjoyed the sensation of her grandson's cock reacting to all the teasing he was getting.

That hard dick twitched and throbbed, growing harder and if possible a bit longer as the tormenting continued. Lucy began to fear that he would fill her mouth with a huge load of cum even before the enema began to fill his bowels. Then she took some independent action and began to apply pressure to his balls and she was merciless.By the time Serena released the clip to start the flow, his dick was only half-hard as the result of the brutal treatment that his granny had dished out to his sore balls.

This time Serena took over teasing his cock while Lucy made sure that the flow of ice water was properly monitored. She could not help seeing what effect moving the nozzle back and forth within his asshole had on Billy. Lucy discovered that the boy's cock responded when the nozzle was moved to a particular position, meaning that it was contacting his prostate. She had to push it in to a certain depth and then bend it upwards until his cock began that lttle dance as Serena skinned it with practiced skill.

During her association with Serena professionally she had never seen the mistress employ her mouth when it came to getting her clients off. This was the situation as she teased Billy to the brink and never let him take that last small step that would have freed his balls of the load of nut butter that churned within. Her hand alternately caressed and squeezed his tight balls, controlling the boy's sexual urge and driving him crazy from the frustration of not being in command.

One of the tricks Serena used to add to his misery was to grip the base of his cock in a grip of steel and then steadily slap the head until the boy's cock was bouncing and bending and little moans of pain were issuing from his lips. Then she would grind the sensitive head against the palm of her hand and listen as he panted and grunted, trying to generate enough friction from this contact to bring himself off.

Midway in this enema Lucy was instructed to refill the bag to its limit. Serena continued to torment the boy's cock and bring him to tears as his belly rounded and grew to the point that he looked as if he were pregnant with at least twins. Billy by then was begging and pleading for relief from the unending pressure that made him feel as if his insides were on the verge of bursting.

Just before the bag was empty Serena struck Billy's cock with a vicious blow that made him turn white. She had used her closed fist to drive her knuckles into his dick at its center causing him to bellow in agony and hop up and down as he tried to do something to reduce the pain. "Be still sissy boy or I'll hit you even harder!" she spat, theatening to give him another punch to his enflamed length of tortured flesh. Billy broke down and began to cry like a baby, his will on the verge of being broken for the first time. It would not be the last if Lucy knew anything about how Serena operated, the standard against which all those in her profession were judged.

The weeping youth was once more plugged and made to wait in agony as Serena and Lucy took turns tormenting his cock, bringing him close but not allowing him to come. At the suggestion of the dominatrix, Billy was given the opportunity to take his mind off the agony that was now being generated by the inexorable force of the water against the walls of his intestines and the internal organs now struggling to accommodate to this intruding menace.

Lucy gingerly stepped into the tub and bent forward, spreading her cheeks with her hands and offering Billy the opportunity to worship her asshole with his tongue. He didn't have to be instructed as to what was expected from him. He dutifully began to kiss that chocolate starfish guarding his grandmother's rectum as she wiggled her bottom to make sure that his tongue worked on those regions that gave her the maximum pleasure despite whatever problems he might have. Serena took a turn massaging his bulging belly, crooning that her little sissy boy looked so sexy now that he was pregnant.

"I'm going to give my little sissy boy a nice treat for being so obedient this time. Mommy's going to give her little sissy boy a good ass fucking with her big fat strap-on dildo once that nasty load of water is let out and her sissy boy can bend over and let mommy do him in the asshole until he shoots off all over the place. Won't that be nice? Don't you just love mommy to pieces for doing that for you?"

Lucy was so enjoying her grandson's tongue worshipping her puckered asshole that she almost missed what Serena was promising her sissy boy. As Serena promised to sodomize her grandson his tongue went wild, stabbing at her anus, then slobbering noisily over her butt cheeks as he licked them like a dog. "My god, Serena has turned Billy into nothing but a sissy slave. I can't believe it but his cock is saying that he can hardly wait for his "mommy " to do his asshole with her strap-on. This is unbelievable!" Lucy was in a quandry for she now realized that Billy's problems stemmed more from Tracy's mishandling of him during his formative years than anything else. She began to plan a suitable penance for her daughter to perform so that she could atone for her terrible mistakes made while bringing up her son.

Serena kept at Billy, promising him that he would love her big strap-on as it split his sissy asshole and made him cry. "Those will be tears of joy by the time I'm done with your sissy asshole. Then maybe, just maybe, I'll let you worship my asshole and cunt for a while. Would my little sissy boy with the little weenie like that?"

Billy's tongue actually penetrated into Lucy's rectum and the feeling was electric. Her head was spinning as the boy's tongue wormed its way deeper and deeper into her dark, moist tunnel, eagerly vacuuming up anything his tongue dislodged. Lucy had visions of Billy bound to his bed, his thick cock coiled inside its cage, his fast tongue working away on the asshole of that Teutonic manhater, Beate, while a long line of well-seasoned, sex-mad women waited impatiently for a turn on the super sissy boy who would do anything his grandmother ordered. Then without warning she had an orgasm, a big orgasm, an orgasm that shook her to the core and made her gush a stream of amber fluid from her cunt as Billy continued to lap away at her asshole which now opened and shut in concert with his sucking and licking.