It Comes Naturally to Some (Patreon)

“Just what are you so bent out of shape for lately, Jack? I can’t go a day without you freaking out about me touching something of yours or looking at your computer. Just what are you hiding from me?!”

“Nothing Steph, just lay the fuck off, alright!”

Steph glowered at her boyfriend. The two had been at odds for the past month and their relationship was starting to feel strained. Whatever Jack had been experiencing over these past few weeks to make him so on edge and secretive, made Steph curious to no end; especially since their sex life had been suffering as well.

“That’s it Jack, if you won’t tell me, I’m going to force the information out of you!” Rolling up her sleeves, Steph prepared an incantation she had been planning on using for a moment exactly like this one. Her arms pointed to her boyfriend’s pants and her fingers danced. Jack yelped in bewilderment as his pants unbuttoned and dropped to the ground. He could feel the band of his underwear dragging down in the back and something enter him from behind. The sound of a large vibrator inserting itself into his ass could be heard behind Jack as he stared ahead in shock. His pupils dilated and his irises shifted to a light purple color; for the moment, Jack was under her control.

“Alright Jack, what have you been hiding? Another girl? Money problems? You’re going to tell me right now.”

Jack answered without hesitation, “I have a secret I’ve been keeping from you. I’m scared that if you find out you’ll want to leave me and I don’t want to lose you. It’s so stupid. I just don’t want to watch you go over something that doesn’t matter.”

Steph instantly regretted her actions, “Oh Jack…you goober...I’d never leave you for something small or stupid.” She walked over to him and lightly stroked his face, “Before I pull you out of this trance, I want to ask you one more thing: do you like what I did to you? Do you like your butt being stuffed by that vibrator?” Jack nodded his head, “It feels amazing Steph.”

Steph laughed and slapped her boyfriend’s rear playfully, “You kinky slut.” Holding her hand in front of his face, she released him from the trance, his eyes fading back to their usual green, “I want to hear you say it of your own free will Jack; what’s the secret you’ve been keeping from me?” Jack almost seemed to die of embarrassment; it seemed his blood was busy trying to decide what part of his body to collect in first: his face, or his growing member.

“Steph...I’m so sorry I’ve been so short with you lately...I’ve just been so torn. I really wanted to share it with you, but what I like and what you want don’t overlap...a-and it’s so embarrassing; if anyone found out, I’d just die.” Jack was staring down at his feet now, his erection had gone somewhat soft despite the vibrator still loudly humming behind him. Steph could see how upset he was.

Steph lifted his chin was her hand and lightly kissed him on the lips, “Tell me babe; I promise nothing bad will happen. No one will make fun of you.” Jack smiled so sweetly that Steph thought she just might melt. He fidgeted and his lips quivered as he tried to work up the courage to speak.

Steph embraced him in a warm hug, “I could use my magic to remove it, if it’s such a problem. We can literally forget any of this happened. Is that what you want Jack?”

She could feel him shake his head no, “Steph...when we first started dating...there was this really cute pair of panties you would wear; the pink ones that had ruffles on the butt. I-I used to take them after you wore them and jerk off in them. I promise that I always cleaned them and put them back!” Steph listened calmly to her boyfriend, running her hand through his hair and stroking his back, “Then I started wearing your bras and dresses while you were out...and then…”

Jack stopped for a moment, “It’s really humiliating Steph…”

“Crossdressing is really common, baby, I bet you looked so sexy.”

He smiled, but shook his head, “It’s not just that...I started liking...wearing...diapers...eventually I stopped wearing your panties at all and just bought diapers to wear under your dresses. I have a pacifier and a teddy bear. I stole one of your dresses and I wear it while I hump my teddy…”

Steph had to admit she was a bit surprised by all this, but it was definitely no where near as bad as it could have been, “Jack, as long as you are enjoying yourself you can engage in your fetishes as much as you like.”

“Do you still love me?”

Steph laughed as she felt her eyes grow wet, “Of course I love you, you weirdo; in fact, I have an idea that I think you’ll just love!” Jack’s expression immediately perked up at his girlfriend’s words, he could barely keep himself from smiling as he nodded and hugged her.

“Okay, I’m going to ask you a few question that you need to answer honestly and then I’m going to wipe your memory of everything that has happened since our argument a few minutes ago, okay? Trust me on this one!”

“Alright Steph, I trust you, ask away!”

Grabbing him by the hand, Steph led him to their room, “Where are you hiding all your cute sissy paraphernalia?”

Jack’s face grew redder at the prospect of his girlfriend seeing just how he dressed when he engaged in his secret acts, “The box labeled books at the top right corner of the closet.” He watched as his girlfriend went over to the closet and pulled the box down. She placed it on the bed and opened it, placing its contents one by one on the bed. With each object, Jack felt his cock rise higher. It felt as if his dreams were coming true.

Steph dug through packs of diapers far larger than she had ever seen before, decorated with childish wooden blocks. Baby powder and wipes were present too, making her wonder if her boyfriend had ever actually used them for their intended purpose. Did he fantasize about her changing him? At the bottom of the box she found a few butt toys and a familiar pair of panties she hadn’t seen in awhile; a little more worn than she remembered, but still just as cute.

Steph pocketed the panties and looked up to see her boyfriend still standing where she left him; his pants still around his ankles, his lip bitten in frustration, his cock raised to full attention. She hadn’t seen him so excited in a while, “And the dress? The one you like to wear when humping your teddy. Oh and the teddy. I don’t see him anywhere.”

“The dress I keep in the closet, hanging on the very far right behind all my old coats...I didn’t want it getting messed up...and I keep my teddy under the bed toward the corner of the room so I keep reach behind the headboard and grab him.”

“That just leaves one last thing,” Steph walked back to him, looking around the room and nodding. She pulled the pink, frilled panties back out of her pocket and bent down. Pulling his underwear around his ankles, she tugged both it and Jack’s pants off leaving him naked from the waist down. She stretched the panties out in front of him and looked up, “Go ahead and step in babe.”

Jack breathed in sharply at the sight, desperately trying to contain himself while his girlfriend slowly dragged the frilled fabric up his thighs. Pressing his cock downward into the panties, Steph stretched the underwear around his waist and lightly patted his rear. She embraced him and massaged his cock through the panties, “Does it feel good, baby?” 

“It feels so good Steph...so gooood…” Jack allowed himself to get lost in the pleasure of the vibrator penetrating him and his girlfriend’s hands pleasuring his member. In a matter of seconds he began to ejaculate into the panties; he shook from the orgasm, and took pleasure in the familiar feeling of cum soaked cotton fabric clinging to his balls.”

Steph backed up and giggled, “Is that the face you always make when you dirty up my panties, you naughty little sissy.” Jack could only smile shyly in response, “Alright take ‘em back off, remove that vibrator, put on your clothes, and go stand in the hallway like a good sissy.” Jack did just that; and in the meantime, Steph prepared the spells she would be needing for the rest of the evening.

Standing just as he had a moment before, Jack blinked and found himself face to face with a fuming Steph. He hated to make her upset, but there was no way he could tell her about his being a sissy; she’d leave him for sure.

Steph hoped she didn’t look too angry. She didn’t want to risk messing up such a delicate situation. Having wiped his memory, she would need to go about her plan carefully and not let on how she knew what she knew if she wanted this to go swimmingly. 

“I know what you’ve been hiding from me Jack; and to be honest, I’m a little disappointed in you.”

Jack looked as if he had just seen a ghost, “Wha-what do you mean? I told you, I’m not hiding anything Steph.” 

Steph approached him and pulled a pair of familiar looking panties from her back pocket, “Then would you like to explain to me why I found a pair of my old panties filled with your cum. They looked stretched out Jack. Have you been jerking off in them like some kind of sissy?”

A variety of emotions could be seen across Jack’s face, from fear, to sadness, to happiness; but judging by his obvious boner, Steph was headed in the right direction.

“Tell me the truth, Jack.”

Jack couldn’t meet her eyes as he responded, “Yes...I’ve been wearing them, and cumming in them...like a sissy. You-you’re not going to leave me, are you?”

Steph just laughed, “Leave you? We’ll just have to see...depends on how big a sissy you are. Maybe I’ll find another man, and keep you as a play thing.” Steph grabbed him by the hand and led him into their bedroom, “I was cleaning out the closet earlier today and I thought I’d see if we had any books to put up on our new book shelf. I wonder if you’ll be surprised by what I found?”

Jack remained silent and looked at his feet, “Looks like someone figured out they couldn’t keep making cummies so much without making a mess, so they switched over to diapers; isn’t that right sissy?” Jack nodded in agreement, keeping his hands in front of his crotch to hide his obvious pleasure. Pulling one out of the pack, Steph snapped her fingers and their bed began to transform. 

The modern earth-toned blankets and pillows began to lighten in color, juvenile prints of princesses and rainbows slowly began to appear on the fabric, and frills poofed out from their sides. The rich red mahogany that composed the four-post bed was covered in coats of white, then pastel pink paint. Bars began to raise from all four sides of the bed converting it completely into an adult-sized crib. A mobile dangled from the ceiling with designs of ponies and teddy bears slowly rotating above the crib. Finally, the contents underneath the bed were pushed out as room was made for shelves and drawers that were immediately filled with the sex-toys and changing supplies that had filled the ‘books’ box.

“A much fitting bed for a cute little sissy like you, wouldn’t you say?” Steph snapped her fingers again and the contents that had spilled out from underneath the bed were lifted into the air and sorted in their closet. Steph left the bear on the ground, instead choosing to increase its size to almost as large as Jack and then placing it in the crib. 

With a clap of her hands, Jack’s clothing disappeared in a ‘poof’ of pink dust, reappearing on the ground next to him. He yelped as his body was lifted into the air, slowly moving toward his brand new crib. The soft padding of the bed softened his small drop, and his limbs were immediately restrained by soft pink cuffs that extended from both sides. 

Steph ran her eyes over her helpless boyfriend, surprised by how much fun she was having. She lowered the bars of the crib and crossed her arms, looking at Jack with a smirk on her face. Jack’s cock looked as if it were ready to burst. 

“It’s obvious that you enjoy pretending to be a sissy, but let’s see how you like living the dream.” Steph waved her hands over her boyfriend’s body and pink shaving razors and bottles of shaving cream appeared all around him. In a matter of moments, Jack was covered with shaving cream and quickly cleaned of it and all offending hairs on his body.

Steph began to unfold the diaper in her hand, watching Jack’s expression as he did so. She never thought she’d be so thrilled to diaper her boyfriend. He looked as if he was having the time of his life. Steph slipped the diaper underneath his rear and began to hum nursery rhymes as she powdered his crotch and bottom. She lightly teased him, keeping him just enough on edge so that he wouldn’t get release until he was properly ‘protected.’ 

As soon as the tapes were secured, Jack began to moan. Steph just giggled and lightly patted her boyfriends throbbing crotch, “Aww you just keep getting cuter, don’t you sissy?”

“It was just the tight diaper! I’m not that big a sissy. I promise Steph!”

Steph just rolled her eyes and released him from the restraints, “If that’s so true, then prove it. You already wear diapers and sleep in a crib. I’ve seen your cum in my panties; and now, if I’m not mistaken, you’ve proven you cum in diapers too.”

“You made me! Here, I’ll show you.” Jack walked across the room and began to pick up his clothes, “I’ll show you I’m a man.”

“With those?”

Jack looked down to where Steph’s eyes indicated. The jeans, boxer briefs, and t-shirt he had been holding had been replaced. Now Jack clutched a pair of frilly pink rhumba panties, a pair of thigh-high white socks, and a poofy pink dress. His eyes widened at the sight and he stared agape at Steph.

Steph pretended to be exasperated and placed her head in her hand, “What now Jack, can’t dress yourself? You really aren’t doing yourself any favors! Guess Mommy Steph will just have to help her sissy.”

Jack shielded his eyes as he became surrounded with pink smoke. When the dust finally settled he found himself standing in front of their bedroom mirror wearing everything he had just been holding. Steph stood behind him, her arms on his shoulders, looking over him at his image in the mirror. 

Jack could hear the diaper around his waist crinkle as his dick began to get excited again. He desperately wanted to prove that he wasn’t that big a sissy; but the more she transformed him, the harder a time he was having at showing her.

“Oh yes, there’s my boyfriend, every bit the man he’s always been.”

Jack stomped his foot in frustration and turned on his girlfriend, “I’ll show you I’m a big boy!” He quickly stormed out of the room. Steph couldn’t keep her excitement contained as she ran after her waddling, crinkling sissy boyfriend.

Steph eventually found him in the bathroom frantically rummaging through the medicine cabinet. After a moment, he produced his electric razor, “A man can grow a beard! I have to shave everyday. No sissy does that.”

“You’re right about men needing to shave, but you no longer need to. That’s why I had you shaved, baby. I’m not going to deal with random hairs when I bathe or change you.”

“Buh-bathe me?” Jack’s face reddened again as he dropped the razor in the sink.

“Gotta keep my sissy clean. And bath time is always so much fun for you, isn’t baby? Toys, splashies, and your favorite towel!” Steph held up a large pink and purple towel decorated with images of an ice princess and her sister. She nearly lost her composure when she saw his reaction. 

“I’ll show you!” Jack ran off again. It was almost like a game now; Steph only hoped that Jack was getting as much enjoyment as she was.

“Mommy’s gonna find you! Where did her little sissy run off too?” Steph spoke in a sing-song voice as she slowly approached Jack. He stood in the center of the room, his arms crossed over his poofy dress, “I’m not a sissy! And these prove it!” Steph looked to see where he was pointing and found several magazines sitting on their coffee table. They covered various traditional adult topics like technology, hunting, and world news. Steph just snorted, “What? Your coloring books, sweetie? Just cause Mommy colors with you sometimes, doesn’t mean it makes you a big girl.” 

Jack looked back to the coffee table and began to whimper; before long he slumped to the floor and began to cry. Steph rushed to his side to console him, “Baby what’s wrong?”

“I’m a sissy. Every time I try and prove you wrong I end up looking more like one...and every time I love it. It’s okay if you need someone else to be a man for you…”

Steph pulled Jack into her lap and hugged him, kissing him on the top of his head, “You’re all the man I’ll ever need, sweetheart; and that’s especially because you’re a sissy. I’m not going to leave you, and no one can replace you; understand?”

Jack sniffled as he looked up at her, “Buh-but…” Steph placed a finger to his lips and shushed him, “I have something to show you.” She helped him stand and led him back to their room, which was now completely transformed. The carpet, the walls, the dresser, the mirror; all had been transformed to match the crib. Large toys littered the ground and a pile of stuffed animals covered a rocking chair in the center of the room. 

“Now just one more thing,” Steph snapped her fingers and returned Jack’s earlier memory to him and his worried expression turned to one of joy.

“Oh thank you so much Steph! It felt so amazing being turned into your little sissy; it’s an odd feeling having a fantasy come true.”

“Well it’s still coming true and seeing as how I’ve been the one making changes all night, I figure it’s only fair that I give you the chance to do the same to me...to really make tonight perfect.” Steph handed over a small wand, “It’s only good for one use, so use it well!” Taking a moment to decide, Jack pointed the wand at his girlfriend and watched her become engulfed in smoke. 

Steph rubbed her eyes as her vision cleared and found herself staring face to face with her own reflection in their new nursery themed mirror. The characters on the frame seemed to be looking at her outfit in approval, and Steph couldn’t say she disagreed. Steph wore a matching outfit to Jack, only hers was a pastel yellow. Her hair had been pulled up by yellow ribbons into pig-tails and a thick diaper spread her legs far apart. She looked over to see her boyfriend snuggling with his teddy bear, admiring her from their crib and she smiled.

Jack watched as his girlfriend waddled across their new nursery and crawled into the crib with him, sliding the bars up behind her, “How about tonight, you hump me instead of Mr.Teddy?”

With a bit more magic, Steph lifted the bear out of the crib and placed him among his companions at the rocking chair. She giggled as Jack grabbed her about the waist and playfully tickled her. The two play wrestled for a while before Jack ended up on top of her, his hard cock very apparent through the padding of their diapers. Steph bit her lip, surprised by how wet all this was making her. She couldn’t believe how much she was enjoying her diapers. Before long she joined his motions, pulling him closer to her so that she could feel more of his erection against her padded pussy. 

Jack played with her breasts through her clothing, moistening the fabric as he ran his tongue over the dress that confined her nipples. He began to moan above her louder and louder, and soon Steph joined in. She could feel his cock on the verge of twitching and she watched with delight as Jack arched his back and pressed his diapered crotch into her. He focused all his efforts on gyrating his hips and it drove Steph wild. By the time she felt his cock unloading, Steph had already begun to shake from her orgasm.

It took the two a while to calm down, and even longer to stop talking to one another about their enjoyment of the evening; but eventually Steph was left with a snoozing sissy sleeping on her stomach. She ran her fingers through his hair as he sucked on his thumb, a small puddle of drool forming on her breasts. Eventually she too succumbed to sleep and stuffed her thumb into her mouth, excited for the morning and the rest of their lives.