One Chance To Cum

One Chance to Cum
Note to the reader; this is a sequel to my story “putty a Sissy in His Place” which can be found here; https://www.tumblr.com/babybobbysstories/689874434168930304/putting-a-sissy-in-his-place?source=share

After an eventful afternoon with his Nana, Ethan sat in his playpen, the one in the front room, as he anxiously awaited the arrival of Megan coming home from work.
Today was, after all, May 1st, and that meant the diapered sissy was entitled to his once-every-two-months orgasm. To be fair, it wasn’t entirely correct to say he’d get an orgasm, but rather, it was his chance of getting one. Traditionally, Megan would unlock his device, re-diaper him, and then allow him thirty seconds to do his dirty deed. If he failed to achieve a climax in that time, well, that was just too bad. He’d have to wait another two months for another opportunity.
There were certainly no guarantees, since as the last time he had tried, he had failed within the prescribed time and been forced to suffer the humiliation of his Mommy locking his throbbing penis back into his tiny steel chastity device.
So it was with fierce determination that he was going to try again today.
Ethan was only vaguely aware of the wetness in his diapers, as they were still nice and warm, and he’d only been in them for about fifteen minutes. And these days, Ethan didn’t take much notice until they got really heavy with pee, or cool and clammy, stubbornly clinging to his bottom like they often did when he was secured into his highchair.
As he stacked another low wall of plastic blocks in the small area within his mesh-sided playpen, he heard Mommy’s car in the driveway, signaling Megan had finally arrived. Excitedly, he sat up, feeling once again the fat, jelly punishment plug Nana Helen had stuffed into him while changing his diapers. He knew that was going to make cumming even more difficult within his restrictive time limit, he grumbled to himself.
Ethan could hear the brisk click-click-click of Mommy’s high heels as she came to the door and then it was opening, revealing the pretty woman that used to be his wife. That seemed centuries ago now, and he had stopped thinking of her in that way, which was just as well. She had remarried, to her doctor/lover Frank, and they now lived in a separate part of the sprawling house.
“Mommy!” Ethan cried, as he raised himself to the padded rail of his playpen.
“Hi sissy baby,” she replied with her devastating smile.
Walking over, she bent down to kiss him on the forehead, granting him a fabulous view down the low cut top she was wearing under her blazer. His heart beat faster at the sight of her soft skin and tremendous big breasts, pushing against each other in a sexy display that made his mouth water.
Helen came out of the kitchen and wiped her hands on a small towel.
“Hello Megan,” she greeted her daughter, coming over to hug her.
Ethan stole a forbidden glance to see Megan’s breasts mashing against her mother’s chest as she greeted her back.
“How has my little baby been?” she asked.
“He’s been tolerable,” Helen replied, “The little pantywaist has been beside himself, waiting for you to come home so he could get his sissy orgasm.
“I still think you’re being too generous with him–if I had it my way–he’d never get to cum.”
“I know mother, but once every two months is hardly often,” Megan explained patiently, “And he still has to do it in thirty seconds. It seems to be quite a challenge for him.”
Ethan reflected on just how true that was, as he had only been successful twice in the last year. Oh, but how wonderful it had been, to explode in his diapers and release all that pent-up sexual frustration in a delightful discharge of sissy cream. He was so desperately horny all the time that he could scarcely think of anything else.
“Well sissy,” Megan said as she stood over him, looking down at him with her hands on her curvy hips in a classic pose of superior female authority, “I brought the key home from work so tonight is your big chance to impress us.”
Helen giggled at the notion, as if the diaper-wetting pansy was actually capable of doing anything impressive.
Keep your diapers dry for one afternoon and that would impress me, she thought to herself.
Megan went into the kitchen to get herself a glass of chilled Sauvignon Blanc and Ethan waited in his playpen impatiently, knowing his moment of ecstasy, however brief, was at last, close at hand.
Coming back in, she handed the key to Helen, who was the only one nowadays that dealt with Ethan’s intimate parts. Helping him out of the playpen, she reached under his frilly pink baby dress and tugged his plastic panties down off his bulging diapers. Seeing the wet cotton cloth swaddling him, Helen shook her head as she looked down upon the quivering sissy.
“Did Mommy’s little baby wet his diapers?”
“Uh-huh,” Ethan replied as he blushed before the two of them.
He always felt very childish when she announced it like that. As if he had no more control than an incontinent three year-old, which of course, he didn’t.
Sitting him down on the waterproof pad she had laid on the floor, Helen unpinned his wet diapers and pulled the thick Birdseye cloth forward between his baby-smooth legs. Ethan fidgeted in anticipation as she inserted the key into the small, restrictive chastity device that now had become like an extension of his physical body. As she grasped it carefully, it felt strange to him, as it always did on those extremely rare occasions when she unlocked him; to feel the small, cap-like cage being slowly removed and the long, flexible urethra tube sliding out of his short, stubby little shaft, making Ethan wince with discomfort.
With practiced ease, Helen swiftly removed the cuff ring from behind his diminutive sack, and his shamefully tiny package was free once again. Megan couldn’t help but giggle at its ridiculous size—it was such a pathetic contrast to Frank’s massive cock. Not for the first time, did she reflect that such a tiny little nub belonged in diapers and chastity permanently.
Ethan squealed with joy and kicked his legs as Helen pulled his thick wet diapers back up and pinned them around his narrow hips. He held the lacy hem of his short baby dress up as Nana tugged his crinkly plastic panties back up his skinny legs and worked them around the pee-soaked cloth.
To be sure, it was extremely humiliating having his wet diapers pinned back around him before these two but he was only too willing to pay the price, if that meant he would be able to cum.
Sitting on his fat, diaper-covered bottom, with his legs on either side of him, Ethan looked up in anticipation at Megan who was smiling down upon him.
“Ready, baby?” she asked him.
“Yes, Mommy,” he replied eagerly.
Gazing down at her expensive watch, she held up her slim, perfectly manicured finger.
“Get ready…set…and–now!” she announced.
Ethan immediately began furiously rubbing the thick, fluffy front of his diapers, the crinkly vinyl crackling loudly in the quiet room. He stared at Megan’s big breasts, drooling over her sexy, tantalizing curves as he struggled to get his tiny little penis hard. Unfortunately, the fat buttplug Nana had stuffed into his back hole was distracting him as it stretched his hole and stubbornly ground deeply into his rectum with his every move. He knew she had done that, just to make his masturbating job that much more difficult.
Beads of sweat appeared on his temples as Ethan rubbed himself before the two of them like a horny, pubescent teenager, struggling to get an erection. As he masturbated frantically, he was surrounded by the shameful smell of pee wafting up from his diapers.
He could feel the seconds slipping by like water through his fingers and he knew that time was running out for him.
Meanwhile, Helen was looking down upon him from her seat on the sofa with that “you better not tell” look on her face.
He thought back, an hour previous, when she had come unexpectedly into his nursery, a glistening rubber enema bag in her hand and in her other hand, a fat dildo nozzle connected to a white hose…
“I know you already had your morning enema today, sissy, but I think it’s a good idea to have you as squeaky clean as possible for your session with Mommy tonight,” she told him.
Ethan squirmed in his seat and his brows furrowed with angst. He knew from experience that during these long enema sessions, he tended to have most of his sissy cream milked from him, especially since Nana insisted on using the fat dildo nozzle on him that filled and stretched his back hole to capacity. Intuitively, he knew Helen was using this as a tactic to defeat his chances of being able to cum later on. She resented his opportunities to reach an orgasm–however rare, and she was determined to do whatever she could to stymie him.
Ethan begged her piteously to refrain from the humiliating purge but she merely ignored him and pulled his rubber panties and diapers down, taking him over her firm lap as he whimpered and whined. Before long, Helen was pushing the over-sized dildo nozzle against Ethan’s sissy pussy, making him squirm and wail helplessly as he struggled to escape the fat, rubbery invader.
“Ohhhhh!” he cried as the big, mushroom shaped head of the dildo finally slipped past his pink, puckering sphincter.
Helen took her time, slowly teasing him with the cock-shaped nozzle to begin the careful process of milking him. After a while, Ethan was moaning and gasping like a little girl as she plunged the fat, rubbery shaft deep in and out of his hole. This was the closest he ever got to any kind of sex, so naturally, he was helpless to her ministrations. He breathed heavily as he bit his lip, feeling from time to time, a little precum helplessly oozing out of the tip of his chastity tube.
He felt so weak and emasculated…his sissy cream leaking out bit by bit, and he knew it was only going to make his ability to reach an orgasm later nearly impossible.
His tiny penis throbbed and swelled inside its steel prison, unable to get hard, yet unable to stop the steady flow of semen being slowly milked from it.
After a while, Helen released the clip on the hose and warm soapy water flowed powerfully into Ethan’s rectum. He moaned weakly and kicked his feet, unable to stop his second punishing enema of the day.
“That’s Mommy’s little baby,” she commended him as she gently patted his bottom. Gazing down at the huge shaft buried in his hole, she was pleased to see how snug the fit was and she knew he was being stretched to the very limit.
Ethan squirmed and moaned as more soapy water flowed into his bowels. To his bitter frustration, he could feel yet more precum oozing out of his shaft, every time he flexed his cheeks trying in vain to expel the gargantuan dildo filling him up.
“Ethan, you are not to tell Mommy about this enema, do you understand me?” Helen warned him ominously.
The sissy gulped hard, certainly not wanting to be a willing participant in her plans to deny him his orgasm.
“If you say anything about it, I’m going to paddle your little bottom every day this week,” she warned him menacingly.
Ethan shivered with fear as he knew she had every means of making good on her threat. She ruled his nursery with an iron fist and her rules were law.
Once again, he realized that she had him exactly where she wanted him and there was nothing he could do about it.
“Y-yes, Nana,” he bleated.
He could only hope that he’d still have enough juice left to be able to get an erection but as more and more soapy water filled his belly, and more and more sissy cream leaked out, he became increasingly doubtful.
Helen smiled to herself as she thought about the condom she’d slipped over the tip of his chastity device before taking him over her lap. She was going to put that semen to good use in his pacifier later on.
A month ago, Helen had purchased a unique and perfect pacifier for Ethan; on one end, was five inches of fat dildo, enough to completely fill his mouth and silence any sort of communication or protest from him. On the other side of the plastic guard, was a squeeze bulb, that she liked to fill with semen from the bank she worked at two days a week. Once the pacifier was stuffed into his mouth, Helen took great delight in squeezing the bulb and forcing a creamy batch of spunk down his throat. Refilling the bulb repeatedly throughout the day, Helen ensured that the taste of semen would be coating her sissy’s mouth all afternoon.
“Ten seconds left, sissy,” Megan announced, interrupting Ethan’s reverie and bringing him back to reality.
The sissy gulped in panic and redoubled his efforts.
Staring at his Mommy’s beautiful, full bosom, he felt his little nub at last starting to stiffen in his wet diapers. He rubbed the puffy front with feverish abandon now, determined to extract an eye-crossing orgasm before the two of them.
“Five, four, three, two, one.
“Time’s up, sissy,” Megan told him.
Ethan gasped in frustration.
“Wa-wait! Just ten more seconds!” he cried desperately.
“Nope. It’s back into your chastity device where you belong,” she said as she stood up.
Helen came over, a smug, knowing smile on her face as she bent over and pushed Ethan’s fat cock pacifier in his mouth. Squeezing the bulb, she ejaculated a huge batch of Ethan’s own accumulated semen from previously into his mouth, putting an abrupt end to his protestations as he gagged and struggled to swallow it.
“Maybe in two more months, you’ll be ready to cum,” Megan giggled.
Ethan was too busy gulping down the thick, creamy load in his throat as Helen pulled his diapers down and began putting his chastity device back on. His little penis twitched helplessly as she carefully eased the urethra tube down his short, stubby shaft and positioned the cap-cage over the head of his penis. In no time, the she mated the cage with the cuff ring, compressing his little nub and locking it securely in place once again.
“There you are, sissy. All safe and secure,” she grinned evilly at him.
Ethan shook his bunched up fists in miserable frustration, knowing that once again, Nana had defeated him and successfully prevented his orgasm.
She giggled with glee, looking into his angry face just as he was forced to swallow yet more of his own cum.
“Aww, poor little sissy. You wanted to cum like a real man but you just can’t, huh?” she teased him.
Ethan wanted to say something in his defense but with his mouth stuffed with fat cock, all he could do was to whimper unintelligibly.
“Well, lets get you back into your sissy pampers where you belong,” she said as she began preparing a fresh set of fluffy soft diapers for him, “You leave the orgasms to real men like Frank, and he’ll leave the wet diapers and plastic panties to you.”
THE END