Wearing the Pants is a Privilege

“Shit!” 

Jack could hear his girlfriend cursing in the other room followed by the sound of glass breaking on the floor. Poking his head around the corner he could see her bent over sweeping up the mess, a dark stain going down the inner thighs of her shorts. She stooped lower, having to pull back her raven black hair to prevent it from falling in the milk that covered the floor. 

“I told you we should start having sippy cups in the house. I can’t trust you with a big girl glass.” 

Steph rolled her eyes and turned to her boyfriend. He stood almost a head taller than her, with green eyes and medium length, wavy brown hair. With his muscle definition and tan skin he was quite the catch, but he had a habit of making fun of her. A large grin was plastered on his face, his eyes locked on her crotch. 

“And what’s so funny? Laughing at your own joke again?”

“No; not yet at least. Mostly just amused at how you must have pissed yourself in shock.”

Jack watched his girlfriend’s expression turn to one of annoyance. An expression he was all too used to and enjoyed quite a bit. Her blue eyes stared back at him seemingly without humor. 

“I did drop a glass of milk you know. Ugh…just laugh it up Jack, come on I need to get changed before the rest of my family gets here.” Steph led Jack by the hand back to her bedroom and amused herself by letting him watch her strip her wet shorts and underwear off. Jack found himself growing erect as his girlfriend pulled her damp yellow panties down around her ankles. The lace dragged on her thighs as they came down.

Searching through her underwear drawer she came across the pair she bought most recently: a pair of super comfy pink cotton panties with frilly leg-holes and waistband. She pulled them to her waist and admired the curves of her own ass in her floor length mirror. She could hear Jack snickering behind her and looked back to see him staring at her ass, his hand lightly kneading his crotch through his jeans.

Steph approaches him slowly, a look of seduction in her eyes. She slips her hand beneath his own and lightly kisses the lower part of his neck, “And what do you find so funny mister?” Jack responds by slapping her lightly covered rear causing her to jump, “Just how adorable those panties are. Did you get those in the little girls’ section? I think it would be wrong for me to be dating someone so…innocent, don’t you?” She frowned at him but found herself unable to pull away as he held her close to his body. She could feel his partially erect member pressing against her stomach through his jeans.

“Oh come on, it’s just a joke babe. You can feel my cock, right? I’m so turned on right now.”

Managing to pull herself from him she scavenged a pair of skinny jeans from her closet and put them on, “Well just contain yourself until after dinner. My parents already think you’re a bad influence as is; don’t need my whole family thinking so.”

Slapping her on the rear again, Jack laughed to himself before peeking out her bedroom door. Steph looked over at him as she pulled on her flats, “What is it?”

“I’ve been hearing stuff, looks like your family has been here a little while.”

“And you didn’t tell me? Fuck, Jack what’s the deal?”

Jack shrugged, “I had a good looking ass in front of me. You know how I am.”

Sighing loudly, Steph led Jack by the hand out of the room and into her bustling living room. Jack looked from person to person finding himself feeling terribly out of place. Steph’s family seemed to be one of little variety; almost every member sharing the dark hair, blue eyes, and soft white skin that made Steph seem so attractive to him. He began to wonder if any of her female cousins were just as attractive.

Steph led him through small clusters of her family, introducing him to those that did not already know him. Eventually they found themselves in the dining room with Steph’s nuclear family and a few of her aunts and uncles. 

“What took you two so long? Figured you’d be bounding out the door once you heard my melodic voice, Steph.” Steph’s face lit up as she hugged her aunt Catherine. Catherine was a relatively young widow that had a young daughter that was still struggling with her potty training. At one point Jack was told that the girl, Steph’s 3 year old cousin Sandy, still needed diapers and rarely left her mother’s side. He could see Sandy clutching her mother’s dress even now; however, the thing that drew Jack’s attention most was just how attractive Catherine was. From her plump rear to her large breasts and soft features he was surprised she hadn’t already remarried. Jack wondered if Steph would end up looking so endowed at her age.

“Baby Stephy here had an accident and needed to be changed, that’s all.”

Jack was the only one that laughed but he made up for everyone else for how boisterous he was. Sandy’s eyes lit up at the thought of her not being the only “big girl” that still needed diapers. Steph scowled at him and explained her dropping the glass earlier. Steph assured Sandy that she’d get the hang of her potty training very soon, took her to the kids’ table, and then dragged her boyfriend over to their seats. 

Dinner started not too long after and everyone began to talk amongst one another, everyone except Steph. Steph was far too preoccupied stroking Jack underneath the table. It was something he had always hoped she would do in public, but she had never wanted to before; the difference now was that she wanted him aroused. For almost as long as they had been together, Steph had a fantasy but had never really wanted to change anything about their relationship in order to put it into motion. Given Jack’s attitude today, she decided that it was long overdue. 

Steph smiled to herself as Jack began to fidget in his chair, she had been teasing him for the past thirty minutes. Whenever he looked like he was enjoying things too much, she would pull back and eat and talk normally to her folks. Soon people were done with their dinners and dessert would be brought out. Now was the perfect time.

Leaning over to him, Steph whispered in Jack’s ear and quietly excused herself. She waited for a moment in her room and eventually Jack opened the door and quickly slid in.

“After all that teasing you better get ready to take this; I’m ready to fucking explode.” Jack began to quickly unbutton his pants revealing his black boxer-briefs underneath. Steph made no effort to bend down or undress; instead she laughed and kissed him, lightly patting his ass as she did so.

“Steph…come on…I’m horny, stop playing.”

“Aww I’m sowwy; maybe I’m too innocent to understand?” 

“Steph are you seriously mad about my little joke earlier? Come on. All I did was poke fun at your panties and your spill. Can you blame me?”

“Yes. I can and I have. I’m just wondering if Baby Jackie would like a taste of her own medicine.”

“What the fuck do you mean? Come one Steph just suck me off or something so we can get back to dessert.”

Jack breathed a sigh of relief as Steph began to pull her shirt up, only to stare in bewilderment as an identical pair of black boxer briefs greeted him around Steph’s waist, “Listen here Jackie; I wear the pants in this relationship now. Do you understand?”

“How the fuck…”

Steph smirked from ear to ear, an expression Jack was entirely not used to. Jack watched as she reached over and lifted his shirt revealing a frilly pink waistband poking out from his jeans. Lifting the shirt further, frills from a matching bra could be seen underneath the fabric of the shirt.

“Wha-what? I didn’t put these on. I swear!”

“I know you didn’t Jackie. I did. I told you; I’m teaching you a lesson. Maybe now you’ll be better behaved.” Jack squirmed at her cupping his butt. She had him pressed against a wall and as odd as the situation was he couldn’t find himself using force against her to stop it. She slapped his ass this time, causing him to jump a bit. He could feel the fabric of his jeans constricting his legs as the tightened to his body becoming a duplicate of his girlfriend’s jeans. 

“Mmm mmm I love seeing your adorable little panties poke out the back of your tight ass jeans babe. You’ve got a great ass. In fact, it’s looking so good, I wanna see more.” Jack yelped as Steph slapped his rear again. Looking for any signs of change his eyes found the fabric of the feminine skinny jeans creeping up his legs until they came to a stop; the leg-holes of which now rested directly next to his crotch. The pockets of the short-shorts he now wore poked out the bottom of the leg-holes, as did the frilly pink bands of his panties.

Having enough of the situation, Jack ducked away before Steph could do anymore spanking, “Alright Steph, I don’t know how you’re doing this, but need to stop right now. Change my clothes back.”

“Or what? Maybe I should just call my folks in her to see what a sissy my boyfriend is, hmm?”

Jack couldn’t argue with her there. He’d have to find some way to make her change them back.

“Steph please…”

Steph moved forward quickly and silenced him with a figure, shushing him quietly as she placed her hand on the crotch of his short-shorts. She kissed him on the lips and moved to his neck; all the while her hands dexterously unbuttoned the shorts. Steph slipped her hands into her boyfriend’s shorts and stroked his cock slowly, “No need to fret, I’m taking care of you.”

Jack decided that arguing with her now was not the best decision. He arched his back and turned his head to the ceiling, silently moaning at the surprising amount of pleasure a mere over the underwear hand job was giving him. Something about the fabric of the underwear, how wearing them in front of her made him feel, and the prospect of her unlocked door being opened by her entire family at any moment.

Steph cooed softly as she began to feel her boyfriend’s cock twitch. The warm feeling of ejaculate filling his pretty panties satisfied her to no end, “Oh Jackie, you can’t last very long can you? It must be so embarrassing to do this in front of your girlfriend. It’s almost like it was an accident.” Steph kissed his neck and softly stroked his cheek, “But little Jackie can’t help her accidents can she? That’s why she needs a little help.”

Still in a daze from one of the most powerful orgasm of his life, Jack did little to fight his girlfriend turning him around and bending him across her bed. Steph slid her hand between his thighs and lightly patted them. Too caught up in his own thoughts, Jack spread his legs for her slowly. He couldn’t get over how humiliated he was over barely lasting a minute before cumming; it hadn’t ever happened before. Pressing his chin to his chest he could see his softening cock in the cum stained panties. The sight was enough to get him excited all over again.

“Looks like we’ll be a little late for dessert…seeing as how baby Jackie needs to be changed.”

Steph’s hand made a loud smack as it met Jack’s lightly covered rear. Jack winced in pain as he watched the pink panties balloon outward, turning more juvenile in design and shape. A crinkling noise could be heard issuing from his crotch and a pressure was applied that caused Jack to breathe in sharply. He couldn’t cum so quickly next time; not again. 

White, plastic material began to poke out from the frills of the pink, princess print panties. The girly denim shorts changed colors to a soft, pastel pink and began to stretch upward along his skin. Jack watched, bewildered, as the frilly bra he was wearing stretched down to meet it and form a pair of pink, heart-covered shortalls; all the while, his shirt shrunk down to a bib that dangled from his neck. After a moment of reading the upside down text he realized he was now wearing an article of clothing that actually said: “Mommy’s Special Little Sissy.” Lastly a pacifier hung from his chest via a strap of cloth, the nipple of which was vaguely phallus shaped enough to put Jack on edge.

“D-did you put me in diapers? Steph stop this right now…I…I don’t like it.”

Jack couldn’t see her expression, but he could hear her soft laugh, “Oh, Jackie, all I have to do is pat your little diapered crotch to tell how much you love it.” Steph did just that, leaving her hand to gently massage the area. She loved how all talk he was, slowly beginning to hump her hand and moan, “Now, now little sissy. We wouldn’t want you having another accident so soon. It would be so embarrassing for my big, strong adult boyfriend to cum like a pathetic little sissy in his diapers, wouldn’t it?” 

“Y-yeah…I wouldn’t do that babe. I promise.” Jack had slowed his humping and his breathing had turned long and drawn out. He was trying so hard not to cum.

“Are you my big strong boy?” Steph gripped his cock hard through the padding and bent over Jack, pressing her breasts against his back, “If you can keep your diapers clean of your sticky little accidents, I’ll allow you to graduate to pull-ups. How does that sound? Pretty pathetic for a guy your age, but I know how hard you’re trying.”

“I c-can do itttttttttt.”

Only he couldn’t. At first he just whimpered, but as soon as he felt the point of no return he humped her hand aggressively and moaned loudly as his cock emptied its first load into the thick padding. 

“Oh my god, Jackie, you’re really not trying. Well if you like this stuff so much, I guess it’s my duty as your girlfriend to help.” 

Jack’s face was beet red as the pleasure of his cock’s release finally left him. He couldn’t understand it. Normally, Steph would be on her knees deepthroating him or on her back moaning in pleasure; now he was cumming in diapers and weirdly liking it. He needed it to stop. He didn’t want to like this forever and he didn’t want things to get worse.

“Steph….I…” She didn’t give him a moment to talk before she spanked his padded rear. Steph watched with great satisfaction as her boyfriend fell to his knees with his arms resting on the edge of her bed, the diaper around his waist expanding and absorbing the material around it, until all he wore was a thick frilled diaper that spread apart Jack’s legs to the point of reducing him to crawling. Along with his clothing disappearing, mitts and booties appeared on Jack’s hands and feet, locking in place and further rendering him helpless. 

Steph leaned down and ran her hands along the thick, pink ruffles, “There, there sissy; that ought to hold all your cummies. Now were you saying something?”

Jack turned over and sat on his padded bottom with a loud crinkle; she had never seen his face so red, “Change me back Steph! I’m sorry I made fun of you…you’re not a baby, or clumsy…”

“Then who’s the clumsy baby from now on? Who wears the pants from here on out?”

Jack’s mouth opened in shock, “Just what do you mean? You go back to your stupid pink panties and you give me my clothes back.” Steph frowned at his response and sighed, “Tell you what Jackie…” she lifted her shirt and undid her bra, tossing it to her boyfriend’s feet, “You suck on my breasts and tell me you don’t like it and I’ll do you one better.”

“I’m listening…”

“I’ll apologize, put myself in diapers and a pretty pink dress, and you can take me out to my family to be properly humiliated.”

Jack imagined that very situation and found himself growing more aroused than ever. He pictured her crawling out of her room and begging his forgiveness in front of everyone, “More than that. You tell everyone that I’m in charge and every night before bed, you beg for a spanking and your diaper.”

“Fine. I promise. Hell, I’ll even call you Daddy in public,” Steph leaned down close, her breasts inches from Jack’s face, “Now sit in my lap little sissy and let’s see how strong you are.”

Jack eagerly watched as she sat on the bed and patted her lap. He needed help getting up with his thick diaper and mitts, but soon Steph had her nipple lightly touching his cheek, cradling him like a child, “Is my little sissy all ready? All she has to do is last ten seconds.”

“TEN?!” Jack couldn’t believe his luck. Now was his chance to make up for all the humiliation he had experienced today, “I’d go ahead and think of some cute outfits you want to wear when you’re put back in diapers young lady; that way Daddy can spank you for each one and leave you naked save for your diaper.” Steph just smirked as she slipped her nipple into his mouth.

One.

He couldn’t believe it. He was getting hard just thinking about all the things he would do. 

Two.

Dresses, diapers, sex toys; you name it, he would use it.

Three.

Obedience would be important. What tasted so good? What was he thinking about? Oh yes, Steph; he would need to be very obedient for her. 

Four…

He would get to wear all kinds of pretty dresses, cute diapers, and get filled with every sex toy Mommy would let him use!

…Five…

If he was a good little sissy for her, would she buy him a crib to keep him in at night? How might she punish him when his pathetic cock came once more in his diapers?

Two?

Would he get to use his diapers? Would she bring her friends to watch him piss himself?

…mmmm…ph…

Steph watched her boyfriend’s eyes glaze over and close part way. Almost immediately he began to moan and clutch at her hand. She watched with a smile as he dragged it to his crotch and then began to hump. She cooed to him and he giggled, milk dribbling down his chin and onto his bib.

“Tell me something sissy, do you like sucking on my tits?”

Jack managed to remove himself from Steph’s breast and looked up confused. A look of pure pleasure washed over his face and drool dripped down his chin.

“I absowwutwe wubb id…Jack…Jackie make cummies! Cuhhhhhmiiiiiies…”

Jack felt a strange fog lift from his mind as his balls became saturated in his own cum. He became terribly aware of what he just did.

“O-okay I made it ten seconds…so s-s-stop it now.” Jack’s face looked like that of a guilty child’s. Steph tsked at him and wagged her finger. You were suckling for eight seconds before you made ‘cuhhhhhmiiiiiiies.’ A definite sign that you absowutwe wubbed it baby girl. Also, congrats on your new record of ‘Quickest Disappointing Orgasm in your Diaper’.”

Jack cringed as the memories of his breastfeeding quickly returned to him. 

“Aww…don’t look so glum baby girl. I’ll give you one last chance. Look, you drank a good amount didn’t you? Well if you can finish up. I’ll let you wear big boy clothes over your diapers; diapers that you’ll be wearing 24/7. You can pretend to be a big boy in public, but once we’re in private you’re my little baby, understand?

“Yes.” Jack would rather have anything than this no matter the outcome, “but can you tell me one thing?” Steph cradled his head and brought it back to her nipple.

“What, sweetie?”

“How did you do this to me?”

Jack squirmed as the milk began to flood his mouth once more. His mouth quickly fought his brain’s commands and began to suckle automatically. 

“Well, I’ve always had powers; ever since I was born. I’ve always kept it a secret, but I guess you just made me decide to exert a little bit of it to properly discipline you.” Jack barely understood the last part of her sentence. It was far too hard to focus on such big words. He just wanted to cum.

“Mmmmmph mmmmm hmmmmm…”

Jack shook in her arms as he orgasmed once more. She sighed aloud, a smile on her face.

“You really aren’t much of a boyfriend anymore, are you? Weird fetishes, can’t last five seconds without cumming, terribly immature…no, I believe a few more changes are in order.” Placing her hand on Jack’s crotch, she lightly patted the area, “A certain diaper wearing cousin of mine will greatly appreciate your potty training Jackie.” 

Jack’s expression turned to one of horror for only the slightest moment before a satisfied sigh issued from his lips. She peeked in the waistband of his diaper to see him soaking it, “And seeing as how you won’t be satisfying anyone with that thing anyway, why don’t we give you something a bit cuter!” Jack giggled as his cock shrunk to half its size. Steph smiled and stroked his hair, “Did baby like that? Does she like having a tiny penis?”

“Yeth Mommy! Weawwy widdle.”

“Mommy? That’s so cute! And it gives me a great idea. Seeing as how we’re no longer dating, it wouldn’t be right to take care of you like this; I should probably take you back to your parents…” Jack shook his head ‘no’ as she expected, “Then maybe we should make you a part of the family. Would you like that?”

Jack excitedly clapped as he was switched to Steph’s other breast, “Drink up baby. You’ve got some changes to undergo.” Jack immediately got to work at her other breast while Steph ran her hand over his body. Jack’s tan skin lightened, his hair darkened, his green eyes turned blue, and his overall bulk lowered just a bit until he looked as if he very well could be related to her. 

“Now that we’ve got you looking more appropriate for your attitude, I think it’s time we went back out and saw the family, huh?”

Jack was lifted off her lap and helped to the edge of her bed. He sat there in a daze, sucking on his thumb as his brain tried to shrug off the milk in his system. He didn’t fight as a pink bonnet was placed on his head and a pacifier was strapped securely into his mouth. Steph smiled at her new play thing, watching him waddle with each step and desperately clutching her hand. She could see his face growing red again as he became more and more aware of his situation again. He nearly dropped to the floor when he saw himself in the mirror.

“Mmmmmmphh…”

“I can’t understand you, sweetie, don’t talk with your mouth full. I’ll take your paci out when we get you in your playpen with the other kids.” Jack didn’t like that, but no matter how much he struggled; he was far too easy for Steph to control now. Between diaper rubs, her milk, and now soothing baby talk, Jack was helpless.

Steph bent down and pinched her sissy’s cheek, “Who’s a good sissy? Awe oou? Uh? Oou wike diapies, uh pwincess?” Jack fought her advances at first, but she had him so trained that he began to laugh and agree to her humiliating descriptions of him as she lightly tickled his stomach.

“You gonna behave yourself now, Jackie?” He nodded his head, drool dribbling past his pacifier, down his chin, and onto his bib, “Of course you are.” Grabbing him by the hand, she continued to escort him to her room’s door, “Oh, by the way, do you remember my…our aunt Catherine? The one you couldn’t stop ogling. Well, I told her how adorable you’d be after dinner and she said she couldn’t wait to change your inevitably dirty diapers. She really wants to see just how…cute…you are down there.”

Jack’s stupid grin slowly began to fade as he felt warmth issuing from his crotch. He looked down to see his diaper sag and yellow further as Steph opened the door in front of him, revealing his new sissy attire to his new family. The kids of the family had gathered round to poke at and comment on the status of his soaking wet diaper. The adults came forward cooing and commenting on how adorable he was. 

“Aunt Catherine, Jackie was giving me such trouble in there; I’m going to go wash up, could you change him?” Jack was horrified of the thought of being left alone in here, let alone changed like a baby in front of her whole family. He’d have to use the time to talk to her and convince her to let him go.

Jack followed ‘his aunt’ back into ‘his sister’s’ bedroom and frantically began to point at the pacifier keeping him silent. Looking worried; Catherine took it out, “What’s the matter, princess?”

“Please! You have to believe me, I’m not your sissy nephew. Steph did this to me. I don’t know how bu--,” Catherine leaned over and shushed him with a finger, her breasts close to his face, “Everyone’s fully aware of what happened to you, little sissy. You were being rude, and you’re being taught a lesson. A lesson I don’t think you fully understand yet. Oh and by the way, Steph learned everything she knows from me.” 

Catherine placed her hand on Jack’s stomach and pressed, “My niece swapped your potty training with my daughter’s didn’t she?” Jack nodded slowly, unsure of what she was getting at. “She’s been able to use the potty for her number twos for a while; I don’t think you’ll need that function with such thick diapers.” Jack cried out as he felt a pain form in his lower stomach. It felt almost as if instincts took over as he spread his legs and bend over.

“No no no no no!”

“Shhhhh…everyone will hear you humiliating yourself Jackie. Or maybe you’d like that? Forgive my ignorance, sweetheart, I don’t know why I deprived you and everyone else of the enjoyment.” Catherine stuffed the pacifier back in and adjusted the strap, dragging him back out of the room as he desperately tried to contain the mess beginning to force its way into his diaper. 

Jack struggled and kicked, trying in vain to prevent his most recent and worst humiliation, but only succeeded in looking every bit the child throwing a tantrum.

“Jackie! Behave yourself and lie down on the blanket.” Jack looked where Catherine indicated and found a teddy bear pattern blanket covered in changing supplies, all big enough to properly take care of the family’s newest addition. Jack refused to move; instead, he stared at his ex-girlfriend, pleading with his eyes. Catherine huffed and lightly tapped the back of Jack’s knees with her foot, causing him to fall forward face first, his ass in the air. A loud wet fart sounded from his diaper as he landed and the back began to sag as he messed himself helplessly.

Jack did his best to prove them wrong; to show that he wasn’t a sissy, but as he witnessed Steph trying to contain her laughter, he began to sob. Catherine just chuckled lightly as she rolled Jack onto his back. She undid the tapes and flicked his small, erect member.

“Did someone like making messies? Hmm? Did widdle Jackie get a stiffy?”

Jack melted at the baby talk and began to suck eagerly on his pacifier as he tried to rub his cock. He could hear laughter all around him as pleasure emanated from his groin.

“Little Jackie can’t last long can he?”

“Was this why you’re having so much trouble with him earlier, Steph?”

“I’m glad he’ll be kept in diapers and a crib. A sissy like him is always such a handful.”

“I dunno, I think he’ll listen so long as he’s being treated like a sissy. He loves it!”

Once in a clean diaper, Jack was carried into the next room where all the children had been corralled. A large, locking playpen was in the corner and was clearly meant with him in mind. Catherine placed him inside with a teddy bear and a blanket and patted his diapered rear. The children laughed and poked fun at him for a while as Catherine and Steph talked about any new guys she was interested in.

Seeing her new sissy brother so distressed, Steph bent down and consoled him, “Don’t fret Jackie. I’ll take care of your little accidents. I just think you could use a strong male in your life, your new sissy life. Idn’t dat wide widdle sissy?”

Jack giggled at the baby talk, just imagining watching Steph getting truly satisfied by another man’s cock. The thoughts aroused him to no end. No matter how hard he tried to imagine himself as his old, in control self he couldn’t; instead, he crawled over his teddy bear and began to hump it as thoughts of his new ‘daddy’ filled his head.