How to Milk a Sissy by Baby Bobby

[Betty]

How to Milk a Sissy
Author: Baby Bobby, Jun/20/2004 00:45:06 [-04]

Tiffany Johnson, sissy tamer and nanny extraordinaire, sipped from her cup of tea comfortably as she listened to her friend’s words of advice. The lady sitting opposite her in the living room could almost be described as her mentor, Mrs. Payne, a long time acquaintance of many years. They had met on an occasion when Tiffany had been shopping for some baby toys for the sissy in her care, Bobby, a twenty year old diaper wetting pansy. She had immediately developed a repoire with the matronly woman, sharing her philosophies on discipline and her no-nonsense attitude. Both women believed in strict, humiliating treatment of the bedwetting sissies in their care. Both preferred to spank first, and ask questions later.
Mrs. Payne was looking at her younger friend with a mixture of shock and disapproval.
“You mean to tell me that you’re still allowing your little Bobby to have orgasms?” she asked incredulously.
“Well,” Tiffany began hesitantly, “we’ve limited him to one every two to three weeks. We’ve completely eliminated his means of masturbating so that the poor frustrated sissy is kept in a constant state of sexual torture.”
“Hmm,” Mrs. Payne considered, “that would normally be good, except that it seems to me that you’re still giving the pantywaist a free ride.”
Under any other circ-umstances, Tiffany would have felt compelled to argue the point, telling her that Bobby’s life was anything but a picnic, but she had so much respect for Mrs. Payne’s knowledge and opinions that she was intrigued instead.
“What are you suggesting?” she asked in curiosity.
“I strongly suggest that you eliminate his orgasm privileges once and for all. Especially considering that he isn’t contributing one iota to your household.”
Tiffany thought about the endless procession of wet diapers, and plastic panties, not to mention other laundry, baby bottles and other dishes that the sissy created.
“You’re right, as usual,” she admitted.
“What you need to do, is to milk him on a regular basis,” Mrs. Payne stated emphatically, “that way, you need never worry that the sissy can have an orgasm.”
Tiffany looked at her friend skeptically.
“But won’t he get an orgasm in the process?”
“No. Oh no!” Mrs. Payne insisted, surprised that she might think that, “if you haven’t tried my milking technique, you are in for a real surprise. When you’re done with him, he won’t be able to come, even if he’s left alone.”
“Wow,” Tiffany marveled, clearly impressed, “ that’s hard to believe. But does it involve surgery?”
Mrs. Payne frowned disapprovingly.
“Not at all! We won’t harm a hair on your little sissy in the slightest bit.”
“Well then, what are we waiting for?" Tiffany said with a conspiratorial smile.

[Betty]

How to Milk a Sissy, part 2

Author: Baby Bobby, Jun/21/2004 02:52:59 [-04]



Thirty minutes later, Bobby was out of his crib, crouching down on his hands and knees in the living room. Today, he was wearing a light pink summer dress, with a bodice of frilly white lace and short, puffy sleeves. Underneath, his multiple layers of frilly petticoats puffed out the short dress, leaving his now bare bottom on display for all to see. Tiffany had pulled his pink plastic panties down around his ankles and his diaper, which had been soaked from his nap, had been removed.

A large bowl of icewater with an oversized sponge lay to one side while Mrs. Payne readied a strange looking device with a cord that supplied power to it. She lubed it up generously with vasoline and then did the same with her middle finger.

"Okay Bobby,'' she said, ''I want you to stay right where you are for a moment, on your hands and knees.''

Sliding her slippery middle finger along Bobby's crack, she slid it down and into his anus, making the sissy squeal and squirm in surprise.

"Hold still baby boy,'' she instructed as she slid her finger in and out, preparing him for what was to come. Next, she took the coated device which looked like an irregularly shaped dil-do, and coaxed it into Bobby's butthole, which made the prissy pantywaist squirm again.

"Now, I want you sit back but keep your hands on your knees and leave them there, do you understand me?'' she told him in an authoritative tone of voice.

"Mm-hm," Bobby answered meekly as he suc-ked desperately on the fat coc-k pacifier filling his mouth. Guiding him back into a semi-sitting position, she continued to hold the dil-do in place with the palm of her hand while her other hand held the control.

"Tiffany, get some baby lotion and begin stroking his little pee-pee and watch what happens.''

Bobby's diminutive weiner, which was already twitching from the stimulation in his rear, reacted immediately to Tiffany's ministrations. It didnt hurt the fact that as she bent over in front of him, he was treated to a generous view of her fabulous bosum. The perfectly round form of her boobs were showcased within the sheer fabric of her peach colored top. In addition, her lacey 40DD pushup bra created a breathtaking cleavage that clearly had Bobby mesmerized. He stared blatantly at the deep valley between her massive breasts as they rose and fell with each breath she took.

Bobby slobbered and drooled on the big rubber coc-k in his mouth as Tiffany masturbated him. Mrs. Payne responded in kind by clicking on the control box she had in her hand. A soft buzz could be heard from beneath Bobby and his eyelids closed momentarily in exctasy. His cheeks, which bulged with the pacifier filling his mouth, were flushed as was his chest.

As Tiffany stroked his hairless little pen-is with her soft creamy hands, Bobby panted and tensed in anticipation of a shuddering orgasm. Through glazed eyes, Bobby stared up into his nanny's beautiful dark eyes, and then let his gaze wander downward, her big round breasts filling most of his available view.

"Get ready,'' Mrs. Payne told Tiffany carefully, ''...okay...now!''

Just as she switched off the vibrating control, Tiffany jerked her hand off Bobby's pen-is and replaced it with the icy cold sponge that had been sitting in the bowl. His eyes flew open and he gasped in shock as Tiffany held the sponge firmly against his scrotum, looking in his eyes with no sympathy whatsoever.

"Don't even think of moving, Sissykins,'' she warned him sternly.

Bobby whimpered desperately in frustration, his orgasm deprived and replaced with a numbing cold, wet sponge. Whining and moaning, he suffered helplessly, unable to understand why she had denied him so.

After about a minute, Mrs. Payne told her to remove the sponge and put it back in the bowl of icewater, while she lightly dried Bobby's crotch. His tiny bald pecker had shriveled up so much, it looked like a fleshy pair of marbles and a baby carrot.

"Unbelievable,'' Mrs. Payne said disdainfully, as she twiddled his limp member between her fingers like it was a rubber crayon, ''this thing is so tiny I don't even think a midget would find a use for it.''

Tiffany laughed heartily as Bobby pouted and looked down at the floor, utterly mortified.

"You really are pathetic, aren't you,'' Mrs. Payne said in disgust as she shook her head, ''the only place this stubby little thing belongs is tightly pinned into a thick set of diapers.''

A tear of shame trickled down Bobby's cheek as he was made to endure Mrs. Payne's humiliating comments.

"I've babysat first graders with bigger pee-pees than this," she continued.

Bobby wilted under her unremitting glare but remained silent.

"Tell me,'' she said as she turned to Tiffany, ''do you spank him regularly?''

Bobby's eyes widened in fear and he looked anxiously at his nanny.

"Oh yes, he usually finds himself over my lap, three or four times a week,'' she assured her guest.

"Is he naughty that often?"

"No, not necessarily. Sometimes I paddle his bottom just to put him in his place and remind him who's in charge.''

"Good,'' Mrs. Payne said relieved, ''sissies need to be spanked hard and often, especially pathetic pansys like this one,'' she declared firmly.

Bobby shivered as he eyed his nanny pleadingly. He could only imagine what it would be like to be over this fierce woman's lap and he silently prayed he'd never find out.

[Betty]

How to Milk a Sissy, part 3
Author: Baby Bobby, Jun/22/2004 15:22:49 [-04]

"Okay...it's time to get back to business.''
The intimidating lady clicked on the vibrating control as Tiffany squirted some more lotion in her hand. She resumed her stroking of Bobby's pee-wee which, despite his humiliation, reacted predictably, growing to its full erect glory of almost two inches. Soon, he was staring at Tiffany's breasts again and fantasizing about touching them while the vibrating device hummed away deep in his rectum. He moaned deliriously and Tiffany watched Mrs. Payne expectantly.
"You want to look for the telltale signs of impending release,'' she explained clinically, ''when he's just about ready to ejaculate, you'll see his chest and cheeks redden. If you look in his eyes they'll just start to glaze over and that's when you know it's time.
"...Okay...now!'' she declared.
Tiffany immediately grabbed the icy wet sponge and held it firmly against Bobby's crotch, making him cry out in discomfort, sounding like a little girl. Without thinking, he moved his hand from his knee and tried to pull the wet sponge away from himself. Tiffany immediatly slapped his hand harshly and Mrs. Payne responded as well, delivering a sharp, painful smack to his exposed bottom.
Bobby yelped and cried, tears of frustration filling his eyes.
"You just earned yourself a spanking for that little maneuver, Buster,'' Tiffany told him in a tone of voice that left no room for argument.
He put his hand back on his knees quickly and shook his head whimpering in a futile attempt to change his fate but Tiffany only glared at him and held the freezing sponge to his crotch.
"Okay, I think you'll find that the lotion isn't necessary anymore,'' Mrs. Payne said as she clicked the vibrator on once more. The low hum could again be heard but this time, Bobby's pen-is remained limp.
"Now, with your thumb and index finger squeeze his pecker firmly at the base and work your way up to the tip,'' she explained.
"Oh wait, first remove his pacifier, we'll have something to add a little flavor to it in just a moment.''
Tiffany popped the big rubber coc-k shaped pacifier out of his mouth and held it close at hand while she milked the helpless sissy before her. Sure enough, as her fingers reached the tip of Bobby's tiny pen-is, a white gooey load of c-um dribbled out and she smeared it onto the head of his pacifier. Repeating the procedure, she managed to milk a little more before she was sure he had been drained of his pathetic discharge.
Mrs. Payne yanked the vibrator out of his anus without ceremony and began cleaning it up.
"Time to go back into your diapers Bobby,'' Tiffany said as she plopped the c-um covered pacifier back into his mouth. The sissy grimaced as he was forced to suc-k on his own c-um and his nanny led him over to the vinyl changing table.
"When you've finished, we'll try an experiment,'' Mrs. Payne told her.
Tiffany helped the big baby onto the changing table and taking three soft cloth diapers, she slid them under his pale white rump. The distinct form of a pinkish-red handprint could still be seen on his right cheek, before his nanny pulled up the cloth between his legs and pinned the corners together. Snaking up his plastic panties, she tugged and pulled at them to get them over his fat, bulky diapers.
Sitting up straight, Tiffany offered Bobby a splendid view of her chest, thrusting her breasts forward proudly and straining at the thin fabric of her top.
"Alright Bobby,'' she said as she put her hands on her hips, ''here is your big chance. Let's see if you can manage to masturbate your way to a hard-on.''
Bobby looked around uncertainly, the big dil-do filling his mouth, as if he wasn't sure if she meant in front of Mrs. Payne.
"Come on Sissy,'' she said impatiently, ''we haven't got all day.''
Tentatively at first, Bobby began rubbing the front of his thick diapers, the pink plastic crinkling loudly in the room. His face blushed crimson in embarassment as he fell into a rhythm, rubbing in his familiar circular motion. However, he soon found his efforts were for naught. Normally, it was enough just to glance at his nanny's tremendous breasts to make his little pecker stiffen. And now that he was wrapped snugly in his bunny soft diapers, it should only take seconds for the premature ejaculator to reach an orgasm. Now however, it was clear that he could rub all day, but no amount of stimulation was going to allow him to get hard.
He chewed his rubber pacifier in frustration as the realization hit him that he had been effectively deprived of the ability to masturbate. Finally, amidst the mocking laughter of the two women around him, he gave up in futility.
"'You see, we've made him c-um, but without the orgasm. Now he's totally drained and can no longer play with himself or get into any mischief," Mrs. Payne explained patiently.
"Yes," Tiffany nodded, "we should have done this a long time ago."
Standing up, she walked across the room and took the paddle off of it's peg where it hung on the wall.
"And now, it's time for a good, hard spanking,'' she stated emphatically.
Bobby quivered in fear as she reached down and yanked him up by his wrist.
"Mm-uhm!'' he cried in protest, his fat pacifier limiting his ability to argue.
Without delay, Tiffany took a seat on the 'spanking chair', which was the only chair in the room, and proceeded to wrench the terrified sissy next to her, making his dress and petticoats swish audibly.