A Playdate for two Sissies
A Play Date for Two Sissies
“Aren’t you excited to be having your very own play date this evening?” Kendra said enthusiastically as she pulled up the zipper on the back of Mikey’s baby dress and secured the tiny buttons that were behind his neckline and out of his reach. The toddler-style dress was virgin-white with a delicate pattern of pink butterflies, and it flared out widely to a very short hemline, leaving his fat, sissy diapers clearly visible.
Kendra was busily dressing her charge in anticipation of the arrival of Tiffany, their babysitter, who would be watching Mikey tonight. As the day had been a bit chilly earlier, she had decided to put a stretchy pair of sheer white tights over his smooth, girly legs, and the thin fabric easily revealed the cute nursery print plastic panties he was wearing over his ever-present diapers. For some reason, Mikey found that even more humiliating, perhaps because they had seemed to offer a veneer of dignity, but in reality, only emphasized his babyish outfit.
Fortunately for the incontinent sissy, his diapers were currently still dry.
The two of them were standing before the full-length mirror in the hallway as Kendra made a few last-minute adjustments to his outfit. By now, his hair had grown longer, and she was able to style it into two sassy pigtails, giving him that adorable little girl charm. She kept them in place with two pink satin bows, clipped on either side.
Just then, Tiffany’s Mercedez mini-SUV pulled into the driveway and Kendra clapped with glee.
“Your babysitter’s here, sweetie!” she exclaimed.
They both watched as the tall, statuesque woman got out of the driver’s seat and strode around the front of the vehicle, her sexy, high heeled boots clicking on the concrete.
“She certainly is all woman, isn’t she?” Kendra stated with obvious admiration.
Mikey swallowed hard and nodded his head. The fact was—he was totally intimidated by her. With her long flowing, jet-black hair and piercing blue eyes, she was a beauty by anyone’s standards. Mikey knew in any other circumstances--were they to pass each on the street, she would never have even deigned to look his way, so far out of his league that she was. So ordinarily, in this life, he would never have found himself in close proximity with her. And yet, his last experience with her had resulted in him being bent over her firm lap for a good, sound spanking, as he’d kicked his legs wildly and cried his eyes out before the other sissy cuckold, Francis.
He desperately hoped to avoid repeating that experience this evening.
Opening the front door wide, Kendra greeted her friend, and they hugged as Mikey stood in the foyer feeling both childish and awkward in his fancy baby dress, diapers and Mary Janes.
“Come in, come in—I was just getting Mikey ready to go,” Kendra gushed as she ushered Tiffany inside.
“What do you have planned tonight?” her friend asked as she appraisingly eyed the nervous sissy for the first time. She was wearing a very short skirt that showcased her long, silky legs, chic, high heeled boots, and a low-cut fitted top that did nothing to hide her big, beautiful breasts. She gazed down at Mikey as if he were an insignificant worm.
Looking up at her, Mikey saw her as a powerful, authoritative, maternal figure. Having grown up under the strict, unrelenting discipline of his biological mommy, Mikey held a submissive, cowering respect for strong women, particularly tall ones, like Tiffany.
“Steph and I are going clubbing tonight, and I know we’ll be out late—you okay if I pick him up tomorrow?” she asked.
“Oh sure, my crib is a little snug with the two of them in there together, but these sissies don’t mind—do you sugarplum?”
Mikey cringed at her condescending tone of voice, but he was afraid to contradict her. He could still recall having woken up in her crib last week, next to Francis, and the strong smell of both of their pee surrounding them. It was so humiliating!
“I love that slinky cocktail dress you’re wearing,” Tiffany said admiringly, “You’ll have to fight the men off tonight.”
“Thanks! I just got it this week,” Kendra grinned wolfishly, “And who says I want to fight them off?” she grinned with a mischievous wink.
Kendra was a woman who was definitely aware of her looks, and she wasn’t about to let something like a silly wedding ring get in the way of hooking up with some hot guys.
Mikey ground his teeth as intense waves of jealousy swept over him.
It was only too obvious that his wife had gotten herself dressed to the nines for other men to look at, and definitely not for him. As a bedwetting sissy, he could expect a short evening doing childish activities, under the close, watchful eye of his babysitter, while the adults were downtown having a great time.
“Let’s see,” Kendra said as she went through his big, white and pink diaper bag, “Extra plastic panties, Desitin, jammies, his baby bottle and his favorite teddy bear…”
It was everything an incontinent toddler would need for his sleepover.
Scooping up his big, rubber cock pacifier, she pushed it in between his trembling lips.
“Might as well suck on that for the ride over,” she said with a smirk.
Mikey blushed, his cheeks instantly turning a deep red and he looked away in shame.
“Oh! One last thing!” she exclaimed as he strode down the hallway to his nursery. A few moments later, she returned, carrying a silky pink pair of ruffled rhumba panties in her hand.
“I meant to put these on him and I got distracted,” Kendra explained absently.
As she bent over, Mikey lifted one Mary Jane-clad foot, followed by the other, as he let her guide them through the leg holes. With his girlish tights on, the panties slid right up over his thighs and Kendra easily worked them over his bulging diapers as he steadied himself by holding onto her shoulders. He looked just like a helpless baby girl being dressed by her mommy.
The ambient light shone off his pretty silk panties and the two of them looked down at the diapered sissy baby with amusement.
“Well—aren’t you going to be the envy of every pantywaist in the neighborhood!” Tiffany exclaimed.
Mikey cringed in place as he slurped and slobbered on the fat, rubbery cock filling his mouth.
Bending down, Kendra planted a big wet kiss on his cheek, leaving the red lipstick mark as if to brand him.
“Now I expect you to be on your best behavior tonight, Mikey,” she admonished him like a child as she looked down at his blushing face.’
Mikey’s cheeks reddened further at being spoken to like he was only a child.
“Well come along now, sweetie,” Tiffany said as he picked up his diaper bag and guided the daintily dressed sissy boy out the door and towards her SUV. As he waddled along behind her, he spied Francis secured in one of two child seats in the back. Opening the far side door, Tiffany helped Mikey up and into the pink plastic child’s seat, buckling him in securely. Unfortunately, the seat belt pulled his dress back, making his fat, sissy diapers all the more obvious. Gazing over at Francis, Mikey saw that he was wearing diapers too and he wondered if his wife had decided to throw away all his little girl panties. It was small consolation, he reflected, but at least he could count on them both being in diapers and plastic panties for the evening.
The drive to Tiffany’s house wasn’t long, but it caused a little trauma for the sissies when they happened to pull up at a stop light next to a car with four giggling teenage girls. The moment they looked over, they rolled down their windows to jeer and make catcalls at the trapped pansies. The two of them squirmed anxiously and Mikey began helplessly wetting himself in a flood of panic. As the hoots and condescending questions filled their ears, Mikey could feel the thick, absorbent seat of his diapers growing wet and warm as his bladder released the two baby bottles of warm milk he had consumed earlier.
Ten minutes later, it was with great relief that they pulled into Tiffany’s driveway and were soon led inside. She sat them down facing each other on the floor of the living room before helping herself to a glass of champagne from her fridge.
The smell of pee began to waft up around him and Mikey wondered if Francis could smell it too. Sitting there in his warm, wet diapers, it was mortifying to think he had so little control over his wetting anymore.
“As you can see, Francis’ mommy took away his potty privileges and he’s now in diapers 24/7,” Tiffany said with a smug grin.
Mikey looked down at the shiny white plastic panties with their polka dot design covering his thick diapers and he nodded in sympathy even as Francis blushed furiously.
Kneeling down before them, Tiffany handed Mikey a roll of glossy pink lipstick.
“I want you to put this on your boyfriend,” she instructed him, using her voice that allowed for no argument, “And I don’t need to tell you two sissies what happens if I don’t like the finished results.”
Mikey gulped and slurped noisily on his pacifier as he accepted the lipstick and reached forward to put it on Francis.
“Okay, careful now, don’t smear it,” Tiffany giggled as she pulled her cell phone out and started snapping pictures, “This is going to make for a very memorable photo album documenting your first sissy play date!”
As Francis puckered his lips, Mikey applied the lipstick and then on Tiffany’s instruction, handed it over so Francis could do the same.
“And now, how about a nice, sloppy, sissy kiss to show how much you two love spending time together. Mikey—reach around and pat Francis’ s diapered bottom—that’s it, a nice, warm sissy hug.”
Tiffany’s camera continued to click as the two pantywaists embraced each other and kissed passionately, putting on quite the show for their babysitter.
“Okay you two lovers, just keep at it while I go get something,” Tiffany told them.
As soon as she left the room, Mikey stopped kissing Francis who, despite himself, was starting to get aroused by it all.
“Don’t stop!” he squeaked, “She’ll spank us if she comes back and we’re not still kissing!”
Mikey reluctantly agreed and as he planted his pink lips back on Francis’, the sissy sighed with satisfaction.
A moment later, Tiffany returned, striding boldly into the living room, her skirt having been removed and a very large, realistic strap-on dildo harnessed around her shapely hips. It bobbed up and down menacingly and looked truly massive.
“Okay Francis, stand up,” she ordered him as she took a small key from inside the cup of her bra.
The nervous sissy stood up on shaky legs, afraid of what was about to happen.
Pulling down his diapers and plastic panties, she unlocked the sissy’s chastity device and set the pieces aside. Even though he was ashamed to have his tiny little penis exposed, it nevertheless began to harden, quickly rising to its fully erect size of two inches.
“We’re going to have a little fun now,” Tiffany said in a husky voice. Sitting him down on the couch with his diapers and plastic panties around his ankles, she then bent Mikey over the coffee table and pulled his tights and diapers down as well. With a jar of Vaseline, she liberally coated the fat, mushroom-shaped head of her faux cock as she slipped a greasy finger into Mikey’s anus. He squealed helplessly at the abrupt invasion and grew fearful as he saw the look of darkly beautiful determination on Tiffany’s pretty face.
“Even though sissy bois like you two will never get to enjoy another woman’s pussy--ever again, that doesn’t mean your own pussies can’t be enjoyed by others. And today Mikey—I’m going to enjoy stretching yours out until you’re good and sore.”
“No—pl-please, Miss Tiffany,” he begged her, but she was already positioning herself behind him. With her slim hand on Mikey’s back, she kicked his legs apart while the sissy whimpered weakly.
Francis watched with fascination as their babysitter grabbed the massive cock and began pushing it insistently against Mikey’s puckering hole.
“No-no-no!” Mikey cried as she shook his fists, unable to escape Tiffany’s lustful intentions. With a hard push, she rammed the fat dildo past his defeated sphincter, shoving it deep inside his rectum.
“OHHHHH!!!!” he wailed as his eyes widened.
Tiffany grinned victoriously as she pushed her cock all the way in, grinding it hard against him as Mikey’s passage was stretched painfully wide to the very limit. Gasping for air, Mikey sobbed and he struggled to contend with the fat, rubbery monster packing his boi pussy. Tiffany pulled the slippery beast out a few inches before pushing it back again to give the prissy pantywaist every rubbery millimeter.
“There you are sissy…” she grinned, “right where you belong, with a nice, thick cock stretching your pussy.”
Every time she rammed it home, Mikey let out a plaintive squeal, like a helpless little girl as his passage got stretched for all its worth.
Francis was clearly turned on by what he was seeing, and his tiny erection throbbed excitedly, inches before Mikey’s distraught face.
“Why don’t you help out your boyfriend,” Tiffany smirked as she rammed her gigantic cock back into his pouting backside. Guiding his head forcefully, she pushed Mikey forward until his lips were nearly touching Francis’s baby-sized penis. A bead of precum had dribbled down the shiny pink head and Francis smiled eagerly down at his new sissy friend. With another hard push from behind, Mikey squealed aloud, and his mouth opened and closed over the little erection before him.
Of course, Mikey was no stranger to sucking cock, as Kendra’s boyfriend made regular use of his warm, wet mouth on a weekly basis. And by comparison, this was like sucking on a crayon, so small was Francis’ penis.
It twitched and throbbed in his mouth, and Mikey swirled his tongue all around it and savoring the taste of Francis’ precum even as Tiffany continued to slowly pump his stuffed back passage with her monster cock. His own little nub was safely locked away in his chastity device, ensuring that he would get no sexual gratification at all from the pounding he was receiving. He could feel the fat, rubbery head of her cock tease his prostrate but frustratingly, there was nothing he could do to gain any satisfaction from it.
Gazing at Tiffany’s big, sexy breasts, swaying gently within her tight top, Francis was quickly overwhelmed, and he lasted less than a minute. With a weak groan, he came explosively in Mikey’s mouth, his tiny little stick erupting with a warm, creamy load which the sissy cocksucker quickly swallowed. He continued to work the little nub, until he could feel Francis starting to soften within his mouth.
“What a good little sissy,” Tiffany commended him as she pulled her strap-on out of his aching hole, “Make sure you thank him for your orgasm, Francis.”
Francis blushed red but he managed to squeak out his thanks.
There was a changing pad nearby the coffee table and Tiffany instructed Francis to position himself there as she unstrapped the dildo from around her hips. Taking his chastity device, she re-secured the ring around his diminutive genitals and mated the cap-shaped steel cage over the head of his penis, mashing the two parts together and locking it closed.
“There, that’s back where it belongs,” she said firmly as she tucked the key back into her bra.
Taking his diapers from earlier, Tiffany applied a coating of Desitin to his bottom and powdered all over his front area before bringing his diapers up and pinning them around his hips. Now that he had just cum, the idea of being dressed like a toddler held even less appeal than it did normally, and tears of shame filled his eyes. He watched bitterly as Tiffany pulled his babyish polka dot plastic panties back up his legs and fit them over his fat, humiliating diapers.
Snapping her fingers together loudly, she turned to face Mikey.
“Okay, sissy--your turn.”
Mikey was confused but she pulled another key out from the cup of her bra and inserted it into his own chastity device. Unsure of what was about to happen, and with his rectum still throbbing, he was nonetheless excited at the prospect of possibly getting to cum, no matter how it was achieved.
Tiffany unlocked the tiny device and slowly began pulling the cap off, the flexible insert being the last part to come out of his stubby little shaft. It had been at least six months since Mikey’s chastity device had been removed and he let out an audible sigh of relief as the insert was removed, along with the steel cuff ring.
With the cap part removed, his little mushroom head looked more like a bump on his groin than a true penis. He blushed a little as he saw Francis gazing at it in amazement.
“Wow—I’ve never seen one that small,” his sissy friend exclaimed.
Mikey blushed with humiliation, the fleshy little cap of his penis hardly qualifying for the term ‘manhood’.
Placing the pieces aside, Tiffany yanked his wet diapers back up around his hips, tugging at the soggy wet cloth until it was all back in place. She kept his silky rhumba panties and tights gathered around his ankles.
“Okay, Mikey—this is your big chance to cum. I want you, Francis, to bend over the front of the couch. Mikey—you snuggle in behind him…that’s it, place your hands on his hips—good boy.
“Now hump your boyfriend as if you a had a real dick—just like I was demonstrating with you before.”
Mikey’s cheeks flushed red at the prospect of complying with her humiliating command.
Still, it had been months and months since Mikey had felt anything but the cruel grip of steel around the tiny head of his dick and without the urethra insert restricting him, the bunny-soft fabric of his diapers felt wonderful against his baby-sized penis. It brought back guilty feelings of pleasure, when he used to masturbate into his diapers every chance he got.
Gently grasping the fat, plastic covered hips of his sissy friend, Mikey began tentatively rubbing the front of his own diapers against Francis’ soft bottom. As the slippery surface of his plastic panties slid against the fat, padded pampers of his friend’s rear end, Mikey found himself getting extremely excited and aroused.
“That’s it—hump your sissy boyfriend. This is going to make for some great pics!” Tiffany chuckled as she snapped away with her cell phone.
Mikey blushed furiously, knowing that once again, he was being forced to debase himself in front of others. But with the pillowy soft cloth of his diapers caressing his tiny little penis, he felt a powerful orgasm building up. It was mortifying for the sissy cuckold that this was the only way he’d ever be allowed to cum, but as his heart began to pound in his chest and his cheeks flushed with pleasure, the beginnings of a mighty climax were quickly bubbling up.
Gripping Francis’ fat, padded hips, Mikey’s eyes crossed, and he gasped abruptly as the most powerful orgasm of his life shook him. Screwing his eyelids shut, he groaned and whimpered as a year’s worth of unsatisfied sexuality was released into his soft, wet diapers.
It wasn’t much, really. With balls the size of marbles, Mikey’s sissy semen spilled out in just a few dribbles, quickly becoming absorbed in the voluminous folds of his diapers. Still, the relief was immense to the sexually- denied pantywaist, and he nearly passed out from the experience.
“Alright you little sissies, it’s time to get you ready for beddie-bye,” Tiffany said as she gently led Mikey back over to the changing table. Pulling his clammy wet diapers off, she set them aside as she positioned him on a fresh stack of snowy-white cotton. Mikey was in a daze as he watched Tiffany carefully position his chastity device before the head of his penis. It took a couple of tries before the flexible tip of the insert finally disappeared into his urethra and Tiffanny slowly, patiently eased it in until the small metal cap mated with the cuff ring behind his little balls. Inserting the key, she twisted it, locking his baby genitals back where they belonged.
As both of the sissies had come down from their post-orgasmic bliss, they began to feel their humiliating cuckold status all the more acutely, and the mortifying embarrassment of being dressed and treated as babies filled them with deep shame.
Tiffany ignored their emotions as she busied herself slathering Mikey’s bottom with a sticky layer of diaper rash cream. He whimpered weakly as she firmly held his Mary Jane-clad feet over his head, sliding her slippery finger down the crack of his ass to make sure the Desitin got everywhere. Letting his legs down, she powdered his front generously, humming to herself as she did.
“Here you are Mikey. A nice, soft set of diapers to keep the crib sheets dry—that will make sure your peeing stays right where it belongs for mommy’s little bedwetter.”
Mikey blushed with shame and was about to respond when Tiffany pushed the nipple of his baby bottle into his mouth.
“I don’t wanna wear diapers!” he whined bitterly, although the rubber teat stuffed in his mouth muffled his protest, making it sound weak and babyish.
“Hush, little sissy,” Tiffany said dismissively, “We both know you have no control over your wetting anymore. You’re nothing but a big baby,” she told him, her voice taking on the condescending tone meant for a child, “You need diapers and baby panties just like a toddler.
With that, she took a pair of white nursery print plastic panties and after removing his tights and rumba panties, pulled them over his feet to fit them over his fat diapers.
His previous plastic panties, damp and smelling of urine next to him, only further reinforced her words.
“You’re a sissy and a bedwetter and Kendra did the right thing putting you back in diapers permanently—it’s just what you needed.”
Mikey blushed hotly at her patronizing appraisal of him and he sulked as she nursed from his baby bottle.
Reaching into his diaper bag, Tiffany pulled out his jammies, a lemon-yellow top with the script across the chest saying ‘Bedwetters wear diapers’.
“Well, isn’t this appropriate,” she said scornfully as she unzipped his dress and replaced it with the sissy top. Pulling his teddy bear and Ariel doll out from his diaper bag, she gave them to the diapered sissy.
“Looks like mommy’s little baby is just about ready for beddie-bye!” she announced.
Just then, the doorbell rang, giving Mikey a start. Seized with panic, he let out an urgent stream of pee into his fresh diapers.
“I’ll bet that’s Taylor,” Tiffany said breezily, “Francis—be a good boy and answer that.”
The sissy looked horrified at the prospect of opening the door dressed like a sissy girl in diapers, but the memory of last week’s paddling was still fresh in his mind. Rising up on shaky legs, he gulped with fear as he waddled over to the front door. Once again, he reflected that he was paying the price for his small, useless penis.
Reluctantly opening the door, he stood back as a pretty young woman strode confidently through the threshold. She was wearing a snug white top under her stylish jacket and skin-tight jeans that showed her fabulous figure.
“So these are the two sissy cucks, huh?” she remarked with a snide tone.
Kendra stood up and hugged her friend.
“Yep, I’m babysitting them tonight while their wives are out with real men,” she replied.
Taylor shook her head as she looked the two of them over, a look of obvious disdain on her beautiful face.
“Pathetic. Absolutely pathetic,” she declared.
The diapered sissies cringed under her scornful appraisal and both their cheeks reddened with shame.
“Do they use their diapers like babies too?” she asked.
“Oh yes. Mikey here has no control whatsoever over his wetting and Francis has just recently started to wet the bed. Of course, while he’s in my home—he’s diapered 24/7, just to be on the safe side,” Tiffany explained.
“No wonder your wives are out with other men,” she said disparagingly.
Francis was mortified to be in this position. He had only wet the bed the one time he had spent the night here, and he hated being lumped into the same category as Mikey, who everyone knew was totally incontinent.
“Well I hope your wives locked up your little pee-pees, because sissies in diapers don’t deserve to cum.”
“Without a doubt. These pantywaists are on a very strict orgasm schedule but I decided on a whim to grant them some relief tonight. Francis here came in Mikey’s mouth and Mikey came in his diapers as he was dry humping his boyfriend.”
Taylor’s mouth opened in shock, but she quickly recovered and she laughed out loud.
“Here—take a look at some of these pics I took,” Tifanny said eagerly as she showed her friend her phone.
Taylor grinned and giggled as she swiped through the various activities the sissies had been engaged in.
“And now it’s just about beddie-bye time for them. Would you mind helping me with their baby bottles?” Tiffany asked.
“Sure thing,” she said as she accepted a bottle of warm milk from her. As Tiffany took Mikey by the hand, she led him over to the couch, sitting down and arranging him across her lap so that his face was mere inches from her big breasts. Taking his bottle, she pushed it between his lips and Mikey began nursing.
Francis was more fussy---unlike Mikey, he wasn’t accustomed to taking a bottle before bedtime and it made him feel even more childish than he already was. He whimpered and whined as Taylor forced him to nurse from the rubber teat, some of the milk dribbling down his chin.
“This one needs a bib,” she remarked condescendingly.
When he finally finished the bottle, he struggled to get up, but Tiffany handed her friend another one, and she grinned as she forced the nipple back into his pouting mouth. Francis squealed and protested—this was surely going to make him wet his diapers again when Tiffany put him down in the crib! He sulked miserably as he reflected on what his wife would say when she picked him up later.
At last, the sissies finished their bottles and Francis was changed into his onesie for bedtime. Taylor laughed when she saw Mikey’s fat cock pacifier, and she pushed it into his mouth, forcing him to acknowledge her superiority.
The two sissies were led into the nursery and Tiffany tucked them in, Francis settling in to spoon against Mikey’s big, bulging diapers. Both were given their teddy bears and encouraged to stay dry, although it was too late for Mikey—the smell of his pee wafted up from under the blankets, even as Francis was starting to feel the need to go himself. He felt babyish and immature as the girls said goodnight and turned out the light.
To be sure, these two diapered sissies were exactly where they belonged.
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