Meet the Parents - Chapter 4

“Ow! Ow!”

“What?” Jan asked, applying cream to the rash and welts still present on Phil’s buttcheeks and thighs. “I’m hardly even touching you!”

“No no…it’s the cage…” Phil hissed in pain.

“Really? You’re getting hard just from this?” Jan laughed, a little surprised that her touch had so much power.

Phil nodded, biting his lip, shrugging, and turning a shade of pink.

He awoke that morning crying like a baby. Because he was in a cage, Carol allowed Phil and Jan to sleep in the same room, albeit with him in the crib.

When Jan rushed over to see what was the matter, she opened his soggy diaper to find Phil’s cock swelling against the barbs inside the cage from his morning wood.

“I’m really sorry about my mother,” Jan said as she finished carefully applying the cream and a generous helping of powder.

“It’s fine.” Phil said, sucking his thumb for comfort, “it was my fault for spilling the beans so easily.”

“Don’t blame yourself just because my Sisters took advantage of you,” she lifted the front of the diaper up and taped it tight. Careful to not put too much pressure on the cage, knowing the feeling of the padding on his balls alone was enough to get him going. Phil still winced noticeably. “Let’s just get through this day and then we can go back home. Cage free.”

“You think she’ll unlock me?”

“She fucking better.” Jan exclaimed hotly, then sighed, “but just in case, let’s make sure you’re on your best behavior.”

She went over to the closet. “Mother picked out your outfit for today. It’s a little more…extravagant than you’re used to.”

She wasn’t lying. The pink dress was way fluffier and poofier than anything Phil had ever worn. The petticoat skirt would make him and his diapers stick out like a sore thumb.

Phil’s bottom lip started quivering, “Exactly how many people are supposed to be at this Garden Party?”

Jan shrugged nonchalantly, “Probably around…a hundred?”

Phil’s jaw dropped.

“Awww I know honey! But it won’t be that bad! Just try to stay behind the scenes or in the outskirts and you’ll be fine!”

Phil wasn’t so sure.

“You can do it! I promise, and there’ll be a BIG reward for you when we get home!” She said, stroking his chin. “Oh! And I got you something at the mall yesterday too!”

She grabbed something from her shopping bags, handing it to him.

Phil opened the velvet box to find two small, sparkly hoop earrings with diamond studs at the bottom.

“Aren’t they beautiful??” Jan asked encouragingly. “They’ll look so pretty on you!”

Phil really did appreciate the gesture. It always made him feel accepted when Jan bought him something that embraced his feminine nature. Phil never felt like a man’s man. But he spent the majority of his life pretending to be one in order to be appropriate to what society told him a man should be like. It wasn’t until Jan came along and validated his ‘sissy’ lifestyle that he finally was able to be his true self.

“Thank you,” Phil said, trying not to tear up.

Jan helped remove his studded earrings and replace them with the little hoops. Phil felt prettier already.

“Do you want some help with your make-up?” Jan asked sincerely.

“I think I can handle it.”

“Okay, well I’m gonna go see if Mom needs help with anything else.” She gave him a kiss on the cheek. “I love you so much!”

“I love you too.” He said, and he never meant it more than in that very moment.

******

“Lower!” Cindy barked. While everyone else was scrambling to finish last minute preparations for the party, Cindy thought it an appropriate time to work on Phil’s curtseys again. “Kick your right foot back and put the weight on your toe. Dip your head lower, show what a submissive little bitch you are!”

Phil whimpered, his legs burning from the exertion, but he didn’t want to disappoint Jan’s sister and cause her to blister his behind again.

Carol was busy delegating jobs to the catering service and her husband Alice. The wide open field was now interspersed with large, white tents and tables. The fountain at the center had been dyed so that the water was cerulean blue color. Lights were strung from different poles, glasses were stacked into precarious towers, and flowers were arranged for centerpieces.

Phil thought it looked more like a venue for a wedding than a Garden Party. But he couldn’t say he’d ever been to the latter, especially not one set for such high caliber guests.

“You will serve the hors d’oeuvres and fill people’s drinks,” Carol told him after Cindy lost patience with his curtseys.

“And you will turn over any tips you receive to me!” Marcia interjected, always quick to take advantage of any money-making endeavor.

“Those are nice earrings,” Carol commented, reaching her claw-like hand to Phil’s jaw and turning him sideways for a better view. “Did you get those at Claire’s or Macy’s?” She said it like either answer was beneath her. Phil assumed it was some sort of jab that an average income earner like himself wouldn’t understand.

“Madame,” a servant cleared his throat behind her. He was dressed like Alfred, the butler from Batman. “The guests have begun to arrive and are having their cars parked as we speak.”

Carol smiled and clapped her hands, “Okay! Places everyone! Let’s hope this party goes off without a hitch and earns us some healthy donations!!”

There was a hustle and bustle as the caterers, servers, and servants made their last minute preparations.

“MR. AND MRS. BOUFFET!” Alfred announced as a pair of guests entered. It was all very ostentatious, everyone dressed in tuxedos and expensive gowns. Sipping overly expensive champagne and chardonnay.

“MISTRESS DAVILL AND HER PET MILO!!” Alfred called. Phil thought it a bit odd to formally announce someone’s dog, even at an uppity event like this. But when Phil looked over, he noticed the lady in the expensive fur coat was dragging a leash, but it wasn’t a dog attached to it. It was a man in all black latex with a dog mask on, being yanked by the collar on all fours.

Phil suddenly felt more at ease in his own outfit. He still adjusted his skirt every few seconds, constantly feeling like it was flaring up and out of control. But it was nice to know there was at least one other taboo person in his midst.

In fact, as Phil carried the tray of caviar and crème fraîche tartlets around to the patrons, he noticed that more and more of them were different from the norm.

Some wore masquerade masks like they were ready for an Eyes Wide Shut event. Others had leather or chains integrated into their expensive suits or dresses. There were even two men standing together near the gazebo. Not that being gay was abnormal at all, it was the fox ears, nose, and tails they wore that made them a bit different than the rest.

Phil realized this wasn’t a simple gathering of rich aristocrats. It was a convention of kink positive people.

“Well don’t you look lovely, dear?!” A woman in a dress made of peacock feathers mused as Phil filled her glass of wine. She spared no remorse as she leaned over and lifted Phil’s ruffly skirt to examine his diaper. Phil didn’t know what to do, he felt like an animal getting his hindquarters checked at the vet.

“Minerva!” Carol called, bustling over, “I see you’ve met my granddaughter, Phyllis!”

“Ohhh yes I sure did!” Minerva said, fanning herself with a fan that matched her dress. “She’s quite the cutie! And who does she belong to?”

“She’s my daughter Jan’s slave!” Carol smiled exaggeratedly. Phil didn’t agree with the terminology she used, but he didn’t dare say anything.

“Ah yes yes, your youngest one? Always had an eye for discipline, that one!” Minerva replied.

“No, my middle one, actually…” Carol corrected, shrugging, “She’s always had a motherly instinct, ever since she was little. But I never imagined her fascination with changing diapers would last well into her 20’s!”

“Ohh so he actually uses them, does he?” Minerva said, intrigued.

“He most certainly does,” Carol nodded with her nose held high, “he’s made quite a few messes since he’s been here…messes of all sorts…”

Minerva clapped her hands excitedly. “Well now that is something I would just love to see!!”

Phil assumed she met some time in the future, but they both turned to look at him expectedly, as if waiting for the show they’d been promised.

“Phyllis, lift up your skirt and show the nice lady how you use your diapers” Carol instructed, like she was showing off a new trick her dog learned.

He knew better than to disobey. Even though he’d pissed his diapers hundreds of times before, it was always weird doing it in front of a new audience. Phil raised his ruffled skirt, presenting his pampers to the stranger. She giggled and fanned herself faster. Phil’s face flushed and he tried to stare up at the sky and concentrate. It took several awkward seconds for the flow to begin. It took a few more seconds for them to notice.

“Oh I can see it! It’s swelling!” The woman gasped. Leaning in closer to watch the yellow wetness indicator turn blue. The lady found it absolutely comical. Carol seemed less entertained, just happy her guest was happy.

“All done?” The woman asked after the diaper started to sag under the sodden weight.

Phil nodded, bottom lip quivering.

She clapped her hands excitedly. “Well done! Bravo!” she cheered, like he actually accomplished something worth celebrating.

The woman turned back to her drink and shifted her focus to something else in the yard.

Carol placed a hand on Phil’s shoulder, “That’ll do, dear. Off you go.”

Phil released his skirt and allowed it to fall over his fluffy diaper. He couldn’t see Jan anywhere.  Not knowing what else to do, he scampered back to the kitchen to grab another tray of food to hand out.

Several people commented on his outfit, having him twirl for them and babble like a baby about his diaper for their amusement. The place was filling up with all sorts of kinksters. Some were nice enough to tip, often a significant amount,  but Marcia would appear out of nowhere and snatch the bills up before he could find a place to put it.

There was a tap on his shoulder, probably someone else wanting him to suck his thumb and do a little jig for them. Instead, it was a girl in a fiery red sequin dress.

“I’m so sorry!” Jan exclaimed exasperatedly, “I got hung up listening to the Rockwell’s talking about the 3rd yacht they just bought, and how on Earth they’re going to be able to enjoy it if the new tax laws pass…”

But Phil didn’t hear a word she said.

“What?” Jan asked. Bringing a hand to her face. “Do I have something in my teeth? Don’t tell me I've been fake smiling and laughing with fish eggs in my gums!”

“N-no…” Phil stuttered, not even babbling on purpose this time, “Y-you look…”

“Oh I know…” Jan said, running her fingers through her hair self-consciously, “I didn’t have much time to get ready, I—“

Phil grabbed a hand to stop her. “You look gorgeous.”

“Really?” Her eyes lit up. She’d never felt comfortable in her own skin. Not unlike how Phil always felt uncomfortable in his own.

Phil winced.

“What’s wrong?” Jan asked, concerned.

“The cage,” Phil hissed, squeezing his eyes and legs together.

Recognition flashed across her face. “Ohhh! Haha! I didn’t know I looked that good!”

They both laughed, it helped take his mind off the pain of Phil’s growing erection.

“How’s your diaper?” Jan inquired, not bothering to wait for a response but instead lifting up Phil’s petticoats for him. “D’aaaww!!” She cooed, poking and prodding his pissy pamper, “did somewon get a visit from the sog-monster??”

“Yea, thanks to your Mom,” Phil winced again. “And you’re not helping the whole ‘erection in the cage thing’ haha…”

“Ohp! Sorry!” Jan laughed sympathetically. “Do you wanna go change your diaper? Or do you wanna go find a place for you to go squat and make pushies first?”

Phil was just about to say he didn’t need to “make pushies” when another couple came up and joined them.

“Hello,” the man said in a British accent. He was wearing a top hat, black tuxedo, and even a monocle. Like he was cosplaying as the Monopoly man.

“My wife and I were interested in your slave here.” The man said, smiling beneath his handlebar mustache. He put an arm around the woman he was with which, Phil noticed, was probably a trans woman.

“Wh-what are you interested in?” asked Jan, caught off guard.

“Well it’s just so hard to find good help these days,” he said, “Especially ones so…amusing.”

He emphasized that last word with a pinch of Phil’s cheek. Phil visibly cringed, but the man seemed unperturbed.

“So!” the man said with a dramatic clap of his hands, reaching inside his jacket pocket and pulling out his checkbook, “I am prepared to make you an offer!”

“An…an offer?” Jan looked at him quizzically.

“Yes, of course! What do you think? Shall we say…twenty—no—thirty thousand dollars?”

“For what?”

“For his rights, of course” The man chortled as if it were obvious.

Jan was still dumbstruck. “He’s…he’s not for sale.

“You drive a hard bargain! $40,000 then?”

“He’s my boyfriend.” Jan said hotly, getting really tired of having to explain that to people.

The man chortled heartily at that. “No, seriously, what will it be? $50,000? Final offer!”

“No, seriously,” Jan repeated. “He’s my boyfriend and he’s not for sale!”

“Perhaps the two of you, then? We have a nice guest bedroom you can stay in, and a wonderful little cage in the basement that can be retrofitted to look like a crib. It will be—“

Phil didn’t hear the rest of what he was saying because Jan was dragging him away.

“Ughh!” She groaned when they were away from earshot, “these people are insufferable!!”

“We probably could have got 75k out of him.” Phil quipped, trying to lighten the mood. Jan didn’t seem amused, she was still heated, but she eventually cracked a smile.

“So did you need your diaper changed?”

Phil shrugged. “I’m just a little wet, it can probably wait.”

“Hmm…I dunno. You were pretty soaked. Plus I just want to get out of here for a bit anyway…”

She led him by the hand behind the catering tables and scooped up the diaper bag. “Come on. We can use the bathhouse.”

They made their way through the grounds of people. Chatting about stock buybacks and record profits while the rest of the country was arguing about who was causing inflation, all while dressed in their formal, yet kinky, attire.

“And I'm gonna keep paying my laborers minimum wage!” One group cackled loudly as they walked by.

“Darling! There you are!” Came Carol’s sinisterly silky voice. She stepped forward smoothly despite sipping on her 4th glass of Cabernet. “I was just telling the Bridgertons here about your little pet you have.”

Carol’s outstretched hands motioned to Phil with a swish and flick without spilling a drop of her wine.

Jan exhaled exasperatedly, tired of having the same conversation. “You mean: my boyfriend, Mom.”

“Tomato/Tomato, dear.” Carol waved the comment away. “Anyway, Mr. Bridgerton here was rather interested in him for a little…” she pushed her tongue to the side of her cheek.

“What?” Jan asked impatiently, “are they wanting to purchase him too?!”

She said it loudly enough for the couple behind Carol to hear them. The man was wearing a business suit and a latex mask with nails coming out in all directions.

Carol laughed awkwardly, it was the first time Phil had seen her look even somewhat uncomfortable. “If you’ll excuse us for just a moment!” She said to the Bridgertons with a forced chuckle.

She led Phil and Jan a bit further away before tightening her grip and her tone. “Need I remind you that the two of them have made some very sizeable donations to our charity” she growled.

“You mean your charity” Jan retorted. “The one you siphon funds from..”

“Be that as it may” Carol hissedv violently, then poked her head up like a cobra to give the Bridgertons another fake smile, “they have done our family a service, so you will return the favor.”

“What kind of favor?” Jan rolled her eyes, cursing herself for even entertaining the idea.

“Well…” Carol said, hushing her voice and eyeing the Bridgertons again, “Oswald seems rather interested in Phyllis.”

“Interested in what way?”

“Nothing crazy dear, just a little mouth hug, that’s all.”

“A mouth hug?? You mean a blowjob?” Jan was no longer keeping her voice down. So Carol shh’d her.

“If you must be so crass. Yes” Carol admonished. “I sincerely doubt it will be his first time doing so.”

“It would be his first time,” Jan corrected, “on a real one…But I am hardly keen on whoring out my boyfriend to your rich buddies.”

Carol rolled her eyes, “Oh don’t be so dramatic. It’ll hardly take 5 minutes if he does it right. Alice does it in back alleys all the time.”

“Then have Alice do it.” Jan retorted.

“They specifically requested Phyllis.” Carol said, sighing. “Do this, and I'll be in your debt.”

“The only way i’ll allow it is if you remove him from that stupid cage after.”

“Done.”

Jan looked to Phil for confirmation, he nodded, shifting his feet nervously. “And I want to be there while he does it.” Jan announced rigidly.

“You want to watch?”

“I’m not going to miss his first blowjob.” Jan said firmly, crossing her arms to show that she wouldn’t be budging on the matter.

Carol glanced back at the Bridgertons, who were swaying side to side with impatience. She sighed, “I'm sure that won’t be a problem.”

******

Mr. Bridgerton hadn’t said a word since he started following them into the bath house. Mrs. Bridgerton didn’t even come, just hugged her husband as close as the 9-inch nails protruding from his mask would allow and said “Have fun!”.

Phil felt a bit awkward as they made their way into the restroom. He was nervous and a bit overwhelmed by the day, but Jan squeezed his hand as if sensing his trepidation.

“I’m right here.” she whispered, and Phil felt immediately more at ease.

Mr. Bridgerton turned and rested against the counter, waiting.

Again, Phil glanced at Jan, she nodded. Phil knew what he had to do, he fumbled with the man’s belt and unzipped his slacks, dropping them–and the white/red polka dot underwear.

The man’s penis hung loosely, a little more loosely than Phil expected.

He’s uncircumcised. Phil thought. Not that it was a problem, Phil had just never practiced on one. Granted, he’d never practiced on a real penis at all.

Jan’s hand was on his back again, ready to coach him through. “It’s okay baby, you can do it.” she said softly, “Just put your tongue inside the foreskin, swirl it around and get it nice and lubricated.”

Phil hesitantly followed her instructions, trying not to think about how she knew all this. He wasn’t naive enough to think she’d never had a boyfriend before him, he just didn’t particularly want to think about it while he simultaneously had another man’s dick in his mouth.

“Wrap your fingers around it and gently peel it back, that’s it.”

Phil was slurping and sucking on the head. Mr. Bridgerton was making no indication behind his mask as to whether or not he was enjoying it. It made Phil feel a little let down. He would have appreciated a moan or even a grunt for all the work he was doing.

“Don’t forget the shaft, stroke it with your fingers. You’re doing great, baby!”

At least Jan approved. It was all that kept Phil going. He had no idea how boring and how much work a blowjob could be. Holding his mouth open this long and trying to control his teeth was making his–

“Is your jaw starting to hurt?” Jan asked, smiling. Phil nodded with the dick in his mouth. “I know, hon, that happens. You're just gonna have to push through the pain.”

Phil did, using his left hand to massage the man’s balls while the other stroked the shaft and his tongue slurped around the head. He finally got a sign of life from Mr. Bridgerton, who grunted and started breathing like Darth Vader behind his mask. Phil assumed that was a good thing, and it spurred him on.

He was working everything back and forth as much as he could. Mr. Bridgerton started getting louder. Phil could tell he was getting close.

“Oh my god! I almost forgot!” Jan exclaimed, digging through the diaper bag. She pulled out a large bib, “I know…I know…I’m being such a Mommy, but I don’t want you to ruin your dress!”

Phil already had drool running down his chin, but he didn’t argue as Jan wrapped it around his neck without Phil even having to remove the penis from his mouth.

Mr. Bridgerton’s legs started quivering, the muffled breathing behind the zippered mouthpiece of the latex mask grew louder and faster.

“Do you want it in your mouth or on your face baby?” Jan asked Phil.

“Face.” said Mr. Bridgerton, speaking up for the first time since they’d been here.

Jan shrugged. “Okay, open your mouth and start stroking, don’t lose your progress!”

Phil did as instructed, using his saliva and the extra skin as lubricant to stroke the man back and forth.

He kept his tongue dangling out and his mouth flopped open like a hungry or excited dog. Still stroking, then stroking more, then stroking again.

It felt like it was taking forever. Phil had originally been scared of the imminent cumshot, but now he was growing impatient. His jaw was hurting even more from holding it open.

Just when he thought it was never going to happen, a shot of semen hit him in the eye. Then another on his nose, his chin, his lips, and into his mouth.  The taste was bitter, salty, Phil tried not to cringe as he continued to get blasted by the warm goo.

Mr. Bridgerton continued to spasm almost silently until Phil had milked out every last drop. His breathing was heavy as he pulled up his pants, tightened his belt, and left the room without a word.

“Good job honey!!” Jan squeaked excitedly, using the bib to clean his face of the sticky mess.

Phil tried to gulp down what was in his mouth. He was thankful it wasn’t a full load, he probably wouldn’t have been able to handle it all.

“I’m so proud of you!!” she grinned, going to hug him, but then thinking better of getting jizz on her dress.

Phil felt good to have her approval, but he also felt like a cheap whore that just sucked a stranger’s dick.

“Come on!” she said, “Let’s get back to the party before mother gets impatient.”

******

As darkness descended over the garden, the patrons descended into chaos.

There were more shambles and shenanigans going on. The man dressed as a dog before was now barking and chasing his tail, fetching dildos and performing tricks for the crowd around him.

One woman was removing her top in pieces like a jigsaw puzzle, slowly revealing more and more of her skin while the onlookers showered her with very expensive champagne.

Another woman was in a mini-pool getting a completely different type of golden shower…

Phil tried to act like everything was normal as he served Oysters from the tray. He doubted they needed any more of an aphrodisiac, but they took them gratefully.

“Where have you been??” Marcia growled, startling Phil so much he almost launched the tray into the air.

“I…I was…”

“Having a little fun I see…” Marcia smirked, peeling a bit of dried jizz from Phil’s cheek.

Phil blushed, “I…yea…” he shrugged, not knowing what to say.

“Did you at least video it? First time blowjobs sell like hotcakes, especially for sissy losers!”

Phil shook his head. “I was just–”

“Phyllis! What are you doing?” Cindy seethed. “You’re supposed to be serving the guests! And you still haven’t gotten that stupid curtsey down! I swear i’m gonna pull down those pampers and blister your behind so b–”

“Just what is this I hear over here?” Carol glided in, “You girls are supposed to be out garnering donations.” she chided with her nose in the air, then she turned to Phil, “And you,” she seethed, “I heard your little mouth left much to be desired! I can’t believe you’ve been a sissy this long without learning how to properly–”

But Phil didn’t hear the rest of what she said. He had been so overwhelmed by all of them that he was on the verge of having a mental breakdown. But then, in the clearing, he saw Jan. The way the light was hitting her seemed to make her glow like an angel, like the savior he didn’t know he always needed. She smiled at him as he approached, making the area glow even more.

Phil was so drawn to her. Like a moth to a flame he simpered over, and before he knew it, he was on his knees.

“What are you doing?” she giggled.

Phil took her hand in his. “You are…the most amazing woman I have ever met.”

Again Jan smiled that gorgeous smile, albeit a bit bewildered.

“Before I met you, I thought I was a loser. I thought I was never going to find someone who would accept me for who I am. But then you came along, and not only have you embraced every bizarre thing about me, you’ve pushed me to become even more of a sissy baby than I ever thought I could be.”

Jan made to say something, but Phil wasn’t done. He didn’t care that there were people watching now, gathered in a circle around them while he was dressed in such a ridiculous outfit with another man’s jizz crusted on his face.

“You’ve always supported me in everything I’ve tried to do. You’ve never given up on me, even when you had the opportunity to sell me for thousands of dollars, you turned it down.” They both laughed. “And that’s why I’d like to ask you…”

Phil never imagined he’d be doing this while looking like a diapered sissy doll, or with a bunch of pompous, rich aristocrats crowding around to watch. He wished he’d had a ring, but he didn’t exactly plan this. Instead he did the only thing he could think of. He took out one of his earrings. The one Jan had bought for him yesterday while thinking about him. He removed it and grabbed her left hand.

“Jan Brady…will you marry me?”

The words hardly came out as Phil’s voice croaked and his eyes welled with tears. He wouldn’t have thought she even heard him had it not been for her covering her face with her hands the way every girl does when they get proposed to.

It was Jan’s turn to cry now. Phil was a bit worried at that, but her smile reassured him. She opened her mouth to say something, but her sister cut her off.

“Jan…” Cindy said, looking on. “Do you really want to change his diapers for the rest of your life??”

Jan sniffled. Drying her eyes and collecting her breath.

“You’re damn right I do!”

******

“That wasn’t so bad…was it?” Jan asked, playing with Phil’s earring that happened to fit perfectly on her left ring finger.

“What? The party?” Phil asked, turning the wheel of the Jeep so that they were back on the road away from his future in-laws house.

“No, silly!” Jan laughed, “I know that was a bit of a disaster, but I meant meeting my parents. It wasn’t that bad! Right?”

There was a silence that hung for a while between them. Then they both burst out laughing simultaneously.

“Okay, fine. It was terrible!” Jan giggled remorsefully, “But I promise they’ll be better next time. Now that they know they can’t convince me otherwise!”

She patted Phil on his pampered crotch. He wriggled a bit in excitement. Glad to be out of that dreadful metallic cage.

“You think that was bad…” Phil said, “Just wait until you meet my parents!!”

To Be Continued...at a Much Later Date