Meet the Parents

Jan pulled up in front of the estate. It was a nice, secluded house that had its own dirt road and white picket fence going around the perimeter. She put the Jeep in park and turned to her boyfriend Phil. 

“Just remember to say ‘sir’ and ‘ma’am’, and don’t say ‘God damnit’ in front of my mother, she’s very weird about that religious stuff” Jan coached. As if Phil wasn’t aware that he should be using proper manners and etiquette. 

“Okay, and what’s your Mom’s name again?” Phil asked, trying to make sure he got everything. 

“Carol, but never call her that or you’ll go straight in the doghouse!” Jan cautioned, a little flustered. 

“Okay…and your Dad?” 

“Step-dad. My real Dad died when I was young. But my Step-dad is…well, you’ll see.”

Phillip gulped. Jan’s nerves were making him nervous as well. “Are you sure I should be wearing this?” He asked, adjusting his collar. 

“Yes. It’s very important you make a good first impression!” Jan reiterated for the 17th time. 

“But, how am I supposed to make a good impression in this?” Phil looked down at the ridiculous outfit he had on. It was a pink bouffant dress trimmed in lace and curls. The skirt was said to be “tea-length”, but it didn’t go past his mid-thigh. Which did nothing to hide his fluffy Rearz diaper underneath. He had kneehigh stockings and a pair of black Mary Jane shoes. His hair was curled and done up into two tiny pigtails with ribbons and bows. 

“They’re aware of how we met and they know almost everything about our lifestyle. They are a very kink positive family” She said, trying to console him, but it did anything but. 

Phil had been scouring the internet for someone to treat him like a sissy baby. He had almost given up finding a girl that would embrace all of his kinks. But then one day he got a message on his Tumblr blog from Jan. She said she liked his pictures and the captions he would write. They talked for a while, Jan making him do certain tasks and humiliating routines for her entertainment. When they weren’t being kinky, they developed a codependence in each other. Sharing some of their most intimate secrets with each other. When they finally decided to meet in person, it was only a 3 hour drive for Phil. They had so much fun that first weekend together that he didn’t end up going back home until 2 weeks after. After 2 months of them going back and forth, they decided to make things official and move in together. The rest was history. In the 6 months they had been dating, she had taken him on a journey through real life sissyhood and beyond. 

“Remember that everything you do, or don’t do, is a reflection on me,” Jan said, “I want you to be on your best behavior. Do I make myself clear?” 

Phil nodded, squirming uncomfortably in his pampers and ruffles. 

They both took a deep breath and sighed. 

“Alright,” said Jan, smiling “let’s do this.”

They climbed out of the car. Phil sauntering awkwardly in his outfit. Though he had worn it many times before, he’d only worn it in public a handful of times, and he never wore it when meeting a girlfriend’s parents. 

Jan took Phil’s hand and led him through the gate of the white picket fence and up the stone pathway to the door. He couldn’t tell if it was his hand shaking, or hers. It comforted him to know that she was just as nervous as he was, but he wasn’t sure what she had to be nervous about. 

Jan knocked on the large, blue door, and waited. She tapped her foot and looked around but no one came. She looked at Phil, shrugged, then grasped the handle and opened it. 

“Hello?” She said as they stepped into the large foyer, her words echoing throughout the large two-story house. 

There was music coming from upstairs, so someone was home. “Come on,” Jan said, leading him up the elaborate staircase. 

When they made it to the second floor, Phil noticed the music was coming from the door decorated like a teenage girl’s room. With stickers and Hello Kitty adorning the outside, and Olivia Rodrigo music blaring from the inside. 

Jan knocked on the area just below the “Do Not Disturb” sign scribed in glittery pink letters. The music stopped, there were footsteps, and then the door swung open. 

Phil was relieved to see that the girl wasn’t too young. Probably a little over 18 and just graduated highschool. Her face lit up when she saw Jan. 

“Oh my god!! Hey!!” She squeaked, throwing her arms around Jan and giving her a tight, enthusiastic squeeze. “I didn’t expect you for another couple hours!!”

“Well it’s easier when you don’t have to stop for potty breaks!” Jan laughed as they broke the hug. “This is my boyfriend, Phil. Phil, this is my little sister, Cindy.”

Phil stuck his hand out awkwardly, “Hi, nice to meet you” he said with a shaky voice, “i’ve heard so much about you!”

Cindy eyed Phil’s outstretched hand as if it carried the plague. Turning up her nose, “why is he not curtseying??” she asked, disgruntled. 

Phil looked over to Jan for reassurance, but her eyes were wide with horror. She nodded in a way that said “come on! Do it! You’re embarrassing me!!”

Phil gulped and grabbed the fringe of his skirt, throwing his foot back and dipping slightly. 

Cindy just watched as if she were sizing him up. “Needs work.” She said simply, craning her neck to the side so she could see under Phil’s skirt, “is that a…diaper??”

Jan smiled gleefully. As if trying to take control of the situation by establishing her dominance. “Mhmm!! Isn’t it cute?!”

“I guess…” Cindy pondered, “never thought about putting a sissy in a diaper before. Could be fun, but don’t you have to…change him?”

“Yea…but I don’t mind it.” Jan said, shrugging. 

Cindy snapped her fingers and did a twirling motion. Phil hesitated, looking back and forth until he figured out what she meant for him to do. 

He gave a slow, somewhat graceful turn. When he was facing away he felt a hand push him over. 

He bent at the waist, feeling his skirt hiked up, and a hand rummaging behind him. 

Cindy squeezed, poked, and prodded the diaper, with no remorse for neither Phil, nor Jan’s, feelings. Though Jan didn’t seem to care in the slightest. 

“How do you even spank him if he’s in a diaper?” Cindy asked. 

“You hit him on the thighs.” Jan said proudly, as if she answered a question correctly in a classroom. 

Cindy nodded like she accepted the answer. She snapped her fingers again, “go in my room and grab the cane, sissy!”

It was the first time she’d addressed Phil directly. Phil was a bit taken aback by the order, but didn’t dare disobey as he stepped from the hallway into Cindy’s room. 

The inside was done up even more elaborately than the outside. There were posters on the wall of different bands. BTS, One Direction, and some other ones Phil hadn’t heard of. In addition to the butterflies, boas, and other cutesy stuff adorning the room, Phil found an entire wall dedicated to spanking implements. There were paddles, leather straps, whips, riding crops, anything Phil had learned about in his years of surfing sissy porn could be found hanging in Cindy’s room and then some. Phil scanned the various instruments until he finally found a thin, rod-like cane. He whimpered as he scooped it off the hanger and brought it back out to the hall to Cindy, presenting it to her and giving a small curtsey. Hoping that might curb her apparent disdain for him.

But, if anything, it made it worse. “His curtsey is terrible…” Cindy scoffed as she took the cane from Phil. Jan flushed with embarrassment, knowing she should have spent more time training him.

“Turn around and grab the railing,” Cindy said simply, barely sparing Phil a glance.

Phil whimpered, this was not how he expected his meeting with Jan’s family to go. Within only a few short minutes, he was already about to receive corporal punishment. He turned and bent over, grabbing the handrail at the top of the stairs.

With no warning, he felt a sharp crack against his hind legs. He yelped, mostly in surprise. But the sharp sting soon followed. He didn’t have time to dwell on it though, as another crack of the cane came again. And again. And again until Cindy was unleashing a flurry of flicks against his hamstrings. 

The back of the legs are far more sensitive than the buttcheeks. The buttcheeks have more cushion (not even including the diaper) and can absorb the blows over a wider area. The back of the legs has very little cushion, and seems to have more nerve endings that make it much more painful.

Phil was soon rocking and blubbering back and forth as Cindy unloaded on him while Jan looked on evenly. 

Phil was always a weenie when it came to corporal punishment. Jan didn’t use it on him often, and when she did, he would use the safeword rather quickly. 

Phil didn’t dare use it here though, he wanted to make a good first impression, no matter how much it stung.

Finally, after what felt like hundreds of swats, Cindy ceased. “That was fun!” she said with the biggest smile, admiring the red lines she’d painted across his behind. 

“What do you say, Phil?” Jan prompted.

“Thank you Miss Cindy!” He said somewhat enthusiastically through his tears. He gave another weak curtsey. The best he could manage with his thighs on fire. 

She handed him back the cane and he obediently returned it to its proper position with all the other punishment devices while Jan and Cindy caught up on small talk.

“So how have you been? How’s college?” Jan asked.

“Good! I go back next week and then only have a few weeks left until break.”

“Have you met any cute boys?”

“Yea, but not any that can take more than 20 swats or so with my paddle, so it’s kind of slim pickings…”

The conversation carried on as if Phil wasn’t there.

“Well, I’m gonna go freshen up for dinner!” Cindy said, indicating she was going back to her room. Jan and Phil both nodded and Phil presented her with an awkward curtsey before Cindy smirked and slammed the door shut.

They both moved down the hall to the next room.

There was chatter coming from inside. Jan knocked hesitantly. “Come in!” Said the voice of another girl. 

They tentatively opened the door and stepped inside. This room was decorated much more lavishly than Cindy’s. Everything was orderly and intricate. There was a simple, yet elegant flow to everything from the decor to the bed frame to the expensive art pieces adorning the walls. 

The girl was sitting at her computer with dual monitors and an earpiece in like she was a telemarketer. She held up a finger to Jan and Phil as they entered, instructing them to wait while she finished her conversation. 

“So I'm checking my account and I’m trying to figure out why I don’t have $100 from you today. So who should I send that video of you dressed like a sissy and sucking a dick to? Hmm? Your friends? Coworkers? How about your wife? I’m sure she would love to see how well you deepthroat and how much you moan with a big fat cock in your mouth!”

The girl tapped her fingers impatiently as she waited for a response on the other end. “That’s what I thought. So you now owe me $150 for today. Call it a late fee. And if i don’t have another $100 by Monday of next week you’ll be spending the night in that truck stop gloryhole again, do you understand me, slave? Good. Ta ta!” She clicked the button on her headset.

“Sorry about that,” she smiled at them, “I swear some of these paypigs do it on purpose just to be punished!”

She swiveled in her chair, removed her headset, sighing. 

“Uh..Phil, this is my older sister Marcia” Jan said. 

Phil curtseyed again, Marcia giggled. “He’s cute!” She said as she inspected him. “How much is he paying you?”

Jan looked a bit taken aback. “Wh-what? He’s not paying me at all.” She said, straightening herself up “I keep him around because I enjoy playing with him.”

“Well of course you enjoy it. Every girl loves having a plaything. But that doesn’t mean you can’t get some money out of it.” Marcia said, wagging a finger, “Never do anything for free. Especially when you can take advantage of pathetic sissies. They’re the easiest to exploit. Use their desperation to your advantage. I thought I taught you better than that…”

“He’s my boyfriend,” Jan shrugged, “I'm not going to have him pay me just to date me. It would make me feel like an escort the whole time.”

Marcia looked visibly shaken, as if the idea of not getting paid was as blasphemous as suggesting 2+2=5, or that pineapple deserved to go on pizza. 

“Well, even if you don’t want him paying you, you can still make money off of him. Do you have any…videos of him?”

Phil and Jan side-eyed each other. “We do…but they’re more…private.”

“Then what exactly are you blackmailing him with?”

“I’m not blackmailing him!” Jan said a bit hotly, beginning to get annoyed.

Marcia rolled her eyes in frustration. Phil could see their sisterly rivalry on full display.

“Well…if you ever decide you actually want easy money, take some videos of the stuff you have him do. I’ll upload them on my site and give you 25% of the profits. Actually 30%, seeing as how you’re my little sister and all. There’s a lot of weirdos out there that are into that freaky diaper shit. Trust me.”

Jan tried to change the subject, “So when do you think you’ll be moving out of Mom’s house?” It may have been meant as a dig, so Jan could get the upperhand in the conversation.

But Marcia just shrugged, “I dunno. I’m making good money here, and saving on a rent/mortgage. But I do have this rich slave that I can probably eventually get to buy me a house…”

Just then her screen started ringing. “Oh! That’s him now…” Marcia said, picking her headset up and clicking the call.

A video of a man in a business suit appeared. 

“Hello, Mistress Marcia!” the man squeaked from inside a bathroom stall. 

“Hello, slave. Did you bring what you were supposed to today?” Marcia replied.

“Yes Miss Marcia!!” he said in a pathetic, high-pitched peep. His voice didn’t match his appearance at all. He had a big, rugged beard, a power suit, power tie, everything about him screamed confidence and exuberance on the outside. But when he pulled down his pants and showed her the pink, lacy panties he had on underneath, what he was on the inside became quickly apparent.

“Does your wife know you stole her underwear?” Marcia asked. The man’s face flushed with shame when he shook his head ‘no’. She laughed wickedly.

“And the plug?”

The man held up a rather large, ribbed, buttplug. “I mailed you the button last week, Mistress…”

“And I received it, slave.” She stood up from her chair to a large pegboard. It had a series of numbers on each peg going all the way to 100. Every single one of the pegs contained a set of keys and/or a keychain of sorts. Marcia reached up to the number 76 and grabbed what looked like a small key fob off the peg. She sat back down, turned the fob over, and pressed one of the buttons.

Immediately the buttplug on the screen started to buzz with such intensity that the man almost dropped it onto the bathroom floor. 

“You know where it goes…” Marcia implied. “And it will stay there until the end of the day.”

The man’s jaw dropped, his eyebrows reaching all the way up to his receding hairline. “The whole day?! But Mistress…I have a very important meeting at 1 o’clock!”

“Then you will be buzzing in your little panties the entire meeting! I don’t see a problem...” Marcia roared through the screen. The giant man seemed to shrink down to the size of a pea. “Now you will send me $50 for being an insolent little twerp, then you will thank me for giving your pathetic little prostate some stimulation!” 

The man blubbered and apologized as he tapped on his phone. A small ding on Marcia’s computer indicated she received the $50 payment. “Good gurl! Now put that plug where it belongs!”

The man was still whimpering as he set his phone down. Jan and Phil couldn’t look away as they watched him drop his panties, his swollen, purple balls dangling underneath his chastity device as he reached around and began shoving the plug into his trembling asshole.

A green light lit up on Marcia’s fob once it was in. It must have had a trigger of some sort that told her when it was inserted, perhaps a temperature gauge or pressure sensor? She hit the button once it was in and a deep hum of the vibration could be heard as the man yelped in surprise. “Good gurl! Now pull your panties back up and get on with your day! Have fun in your meeting!” Before he could say another word in protest Marcia clicked off.

“Ughh..” she sighed. “Nothing like a hard day’s work!”

******

Carol was just coming out of her room when Jan and Phil were descending the stairs.

“Hi Mom!” Jan beamed.

Carol had a warm-inviting smile beneath her analytical eyes. Her hair was pinned up in an elaborate bun that showed great attention to detail. 

“Hello, dear” she said softly but with resolve. She reminded Phil of a docile snake that could strike at any moment. Her and Jan exchanged hugs and kisses on the cheek. “And who is this sweet little thing?”

“This is Phil!” Jan said, a hint of nervousness in her voice.

Carol looked down her nose at him, “Phil? A dreadful name. Hardly fitting for one wearing such attire as this.” She grasped the hem of his frock and pulled it down, as if there were wrinkles she were trying to smooth out. That’s when she noticed the crinkly sound of the diaper.

“Oh, and what have we here?” she mused, lifting his skirt with no remorse for Phil’s trembling legs. They both expected Carol to scold them. Another ‘eww why would you put him in diapers??’. But she just smirked and said “The diapers are a nice touch. Helps further emasculate them and plays with their psyche. Plus, I’ve always wanted a grandbaby!”

Jan sighed at that, releasing some of her built-up tension at her Mother’s approval.

Carol hooked one of her fingers and peeked into the front of Phil’s diaper, turning up her nose. Jan assumed that meant Phil must have a wet or messy diaper.

“Why is he not in a cage?” Carol asked disapprovingly.

Jan sighed again, exasperated. “Mother…please don’t start.”

“Boys like him only think about one thing, dear.” Carol pressed anway, “and if you can control that thing, then you can control him”

“I have no problem controlling him!” Jan retorted, getting hot in the face. “And I'm tired of everybody telling me what I can and can’t do with my boyfriend!”

Carol’s eyebrows rose for the first time, “Boyfriend?” she almost choked on the word, “Boyfriend? You mean…you two are…dating?”

“Yes Mother!” Jan seethed.

“Well then I certainly don’t approve of his tiny thing being unlocked! Who knows where he would try to put it?!” Carol raised her head up even higher, as if her word was law. Like a judge passing a sentence.

All Phil could do was stand there awkwardly while Jan and her mother went back and forth.

“If you would just listen to me you can get a lot more benefits out of this little…relationship” Carol spat the last word as if it were something sour in her mouth. “You can get money, LOTS of money like Marcia and I, or you can be like Cindy and have something to take out your aggression on.”

“I don’t want any of those things, Mother! This is my life and my decision so I’m going to do things how I want. Not how you, or Marcia, or Cindy want!”

She grabbed Phil by the arm and jerked him to follow. Phil hobbled behind her, diaper crinkling as they climbed the stairs.

They passed Cindy and Marcia’s room until they came to one more. Jan hurled the door open, shoved Phil inside, slammed the door behind her, and plopped down on the bed.

Jan buried her face in her hands. Not sobbing, but definitely distraught. Phil placed a soothing hand on her back. Still unsure what to do, but wanting her to know he was there for whatever she needed.  Phil could feel how much her nerves were on fire. It was putting him in a precarious position. Was this his fault? He wanted to make a good impression on what could be his future in-laws. He thought dressing like a sissy would be too much, but apparently it wasn’t enough.

He thought about offering to wear a chastity cage. But even he wasn’t so set on the idea of not getting to cum for the foreseeable future. Or maybe he could just wear it when they were around her family? No, they would know.  Someone like Marcia who has over 50 slaves in chastity around the world probably knows exactly what balls that have been deprived of release look like.

So Phil did the only thing he knew would be a surefire way of cheering her up: he started peeing in his diaper.

He had been holding it for the majority of the ride here. He probably could have let it out then, but he didn’t want to meet his girlfriend’s family in an already soggy diaper. Now that that was somewhat out of the way, he allowed himself to relax and release, flooding his diaper with warmth. He felt the padding between his legs begin to swell, and–because he was sitting down– the tiny trickle that ran down his crack due to gravity.

He put on his best pansy voice. “Mommy…”

Jan raised her head off her hands, sniffling and blinking the excess moisture away from her eyes, “Yes dear?”

“I wet my diapy….”

Immediately her face lit up in a huge smile. She always had a profound motherly instinct. She enjoyed playing with Phil and dressing him like a baby girl the same way little girls enjoyed playing with dolls.

“Oh you did?” she said in a soft but feigned concern sort of way. “Let me check the wittle baby’s diaper…”

She lifted Phil’s skirt, placing a hand on his squishy wet crotch. Giving it more of a squeeze than was necessary. “My goodness! You soaked it!”

Even after all this time, it never got old for Phil to get his diaper checked. He loved the way Jan affectionately traced her hands around it. Poking, prodding, teasing him lovingly. It instantly slipped him into subspace.

“Awww! Feels like somewon likes the feel of their wet diapy, huh?” Jan cooed, the scenes from earlier forgotten as she started getting into the scene for her favorite role. She rubbed the outside of Phil’s diaper, feeling the hints of his hardness inside. She painted the area with her fingers, pressed with her palm, grinding it into him to hear him gasp in delight, only to playfully pull it away and listen to him whimper.

“What should we do about this?” Jan whispered in his ear as she nibbled it. Tracing a finger into the waistband of Phil’s Pampers.

Phil was in full-blown submission mode, his voice quivering as he asked pathetically “W-will you change my diapy?”

“Awww, I'm sorry sweetie but the changing bag is downstairs! There’s no wayy we could go get it now…” she purred, “I guess we’ll have to figure something else out…”

She pushed him back flat on the bed. Pulling her panties down her leg and swinging the same leg  over him in one fluid motion. She straddled him and ground her hips into his diaper. Even through all the padding, she could feel his dick throbbing through it.

They were both panting heavily as they locked lips. Kissing each other passionately in a fit of fervor. Jan lifted Phil’s arms and pinned them down by the wrists, making it clear she was still in charge and in control. She was so wet that she was sliding slickly across the crinkly plastic of Phil’s crotch.

“Ohh myy godd!! I need you, NOW!” she groaned.

The head of Phil’s penis was poking out of the top of his waistband at this point. But it wasn’t enough for insertion. Anyone with a diaper fetish knows that one of the hardest things about diapers is to actually have sex whilst still in diapers. There are ways around it, like cutting holes, attaching strapons, or other creative methods. But none of those really work too well in the heat of the moment.

Jan made the decision to just rip the tabs off of Phil’s diapers and open it up. Phil could still feel the padding of the diaper beneath his butt, and Jan could proceed to put Phil’s cock inside her.

Jan sighed in ecstasy as she lowered herself on Phil’s cock. Getting back into the rhythm, she ground her hips back and forth scantily. Removing her top and bra so that her beautiful, round perky boobs were on display for her boyfriend. She loved feeling Phil get even harder when she took her tits out. Perhaps his desire to be diapered gave him an exaggeratingly large love for breasts, either playing with them or ‘feeding’ from them. But they had always been her secret weapon for getting him squirming the way she liked.

She bounced and bucked on top of him. Allowing him to put his quivering hands against her C-cups. He was in the process of sucking her nipples when his dick flopped out. 

It was a regular occurance when they had sex. Phil obviously wasn’t the biggest. It usually wasn’t giant dicked men that had a thing for diapers. So Phil was no exception. But Jan didn’t let it kill the mood, she gripped his slimey stick, placed it back inside, and resumed riding him. 

About 30 seconds later, Phil was uttering those pathetic little words: “Can I pwease cum, Mommy?”

Jan wasn’t even close to orgasming, but she knew by now that Phil had no chance of lasting long enough until she was. 

She nodded affectionately, “Yes baby, make your sticky mess inside Mommy’s pussy!”

Jan was on birth control, had been since she was young. But she hoped one day to have a real baby of her own. Just not today. Today, the ‘baby’ she wanted was Phil.

She watched as he crinkled up his face, futilely trying to hide his feelings of euphoria. He groaned and whimpered in that pathetic little way he does. Spasming beneath her as she felt herself fill with his warmth.

“Goo goooo ga gaaaaaaaahhh” Phil groaned. Making the sound of him cumming as he’d been trained. Jan smiled as he pumped the rest of his load inside her. 

“Now it’s time for me to get mine!” Jan teased. She climbed off him a bit, letting his flaccid, sticky dick flop out. She did a quick little turn so that they were in the “69” position. Pressing her pussy down into Phil’s face. She knew Phil had lost his horniness. That when he was in his submissive fits, he would be happy to lick up his own cum. But he wasn’t horny anymore, and she didn’t care. If she wanted to cum (and, more importantly, if he wanted to continue having sex with her) this was how it was going to be.

She could feel his goopy load leaking out of her as she sat on his face. Burying his nose into her butthole while she ground the lips of her pussy against the lips of his mouth. Phil started licking. She could feel his tongue against her clit and twitching back and forth between her labia. It felt amazing. 

Phil had always been good at oral sex. Anyone with a smaller-sized dick that didn’t last long needed to be good at oral sex to make up for it. But after a couple months of Jan’s coaching and communication, Phil had been able to make her melt with his mouth. The same way she could make him melt with her words or gentle domination. 

Phil had apparently licked what was left of his load out of her, as he was now picking up the pace and being more articulate with his tongue. Jan was arching her back, squeezing her hips against Phil’s ears as she moaned and groaned. 

Phil was getting hard again. She could see it poking up in front of her. Wriggling and erecting until it was straight up in the air. She smiled, taking a bit of pride in the fact that she could consistently get him turned on. She took his dick in her hand and rubbed it playfully at first. Teasing it. Listening to him whimper under her hips. She gripped his cock between two of her fingers and stroked. 

Phil became even more vehement with this tongue. Licking her hole and up and down her clit with an intense fervor. 

“Unhhhhh!! I’m gonna cum baby!” Jan moaned. Phil’s muffled response below told her he was close too. 

She bucked her hips, practically fucking his face with her pussy while she pulled up and down on his cock. 

“Yes!  Yes!! YESSS!!” Jan screamed as much as she could without being heard downstairs or down the hall as her body rocked into an intense orgasm.

Phil’s dick started spewing into the diaper below him as Jan collapsed on top of him.

They didn’t even have time to breathe before there was a knock on the door.

“Just a sec!” Jan called, pulling the front of Phil’s diaper over his spent penis and taping it shut with practiced speed and efficiency.

The door opened without further hesitation. It was Cindy. She didn’t hide her disapproving countenance at the scene in front of her. Turning up her nose and smirking.

“Mom says dinner's almost ready.”  Cindy finally said, shutting the door behind her before either Jan or Phil could reply.