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  • Posts

    • Jennifer "But now it's time for you to go back to bed little missy." Cindy "Only if I can say hi to the twins first. It wouldn't be fair to leave them out."
    • Jennifer smiles. "I suppose I can't be upset with you for loving your brothers and sisters."
    • As some of you know, Pudding and I were on vacation last week.  And vacations are fun and all, but we had NO writing time!  So on the plane ride home we decided to write a short story.  This one has been up on our Patreon since last week, but we want to share it with DD as well. Please consider supporting us on our Patreon!  We also do commissions now! Enjoy! ~Sophie --------------------------------- Sissy In The Sky With Diapers
      by: Sophie & Pudding “Oh you’re making too much of a fuss about it, Sunny.” His face still screwed up when I called him that, despite the fact I’d been doing it for over a year now. Sunny just had a much nicer ring to it than Sonnet, and with the way our dynamic had developed it was only a natural progression. He shifted uncomfortably in the seat, slinking down into himself, and picking at the tips of his tangerine painted nails and puffed out his similarly glossed lips. It was just a plane full of five hundred people - what was the big deal? “This isn’t fair,” I said again. It was all I’d said for the past hour, until Luna dragged me onto the plane and plopped me down in the window seat. This past year with her was... well, it was an amazing experience. But this was our first vacation together, and she it made clear before we left the house: it would be unlike anything we had ever done. “If it were fair, we wouldn’t be having any fun now would we?” I leaned over and kissed his cheek, using the gesture to slip my hand down the front of his jeans - my jeans, really, that I’d had him wearing for weeks now - and brush my hand over the front of the silken garment I’d coerced him to wear out of the house. He was so damn cute in silk panties, squirming.  If he thought this was bad, he had no idea how much more exciting I was going to make it! I always liked dressing like a girl. It was just one of those things. In high school, I hated it. And in college, I was ambivalent. But this past year, since Luna found out... well I had the opportunity to really enjoy it, without the shame and guilt. And the funny thing was, Luna loved it too! She always had a really strong maternal side, eager to take care of the men in her life. We completed each other, as cliche as it was. And I was just so happy. Or rather, happy when I could hide myself behind the walls of my apartment. Days like this, when Luna put her foot down and dressed me up to go outside, I was all nerves... “You look really cute you know, though I think you’d be a lot cuter in what I’m wearing now.” Which meant a lot of things: the strappy little sundress, cute tights, and lace bracelets. It meant a bra that made it look like my poor under-endowed chest was anything other than modest, and it meant something else I was wearing in place of panties. A garment that I had every intention of transposing upon my little pretty boy. “We need to go to the bathroom.” We. Yes. We hadn’t been in the air more than ten minutes and I was already so embarrassed that I wouldn’t look up from my feet. Any smart person would have thought Luna’s comment about my being cute in her clothes was harmless, but it was anything but.  And as if fate was on her side, the seatbelt light turned off only a second later. She pulled me out of the seat and I tugged her back to sit down. “You want to make a scene?” she whispered at me, and I looked around to find a few people staring. My stomach sank and I followed my girlfriend shyly to the restroom. I practically skipped. Sunny dragged his feet. It was a good analogy for the way we approached our dynamic - I was attracted to his shyness and pretty face, and he was attracted to my carefree confidence... and my pretty face. I opened the door to the cramped little restroom and shoved him inside roughly enough for anybody around to look up and investigate. Before they could, I’d closed the door behind the two of us and pinned his back to the mirror with the force of my lips alone. Spider and prey. Luna and I were the same height, but on days like this, when I wore her panties and jeans, she always wore heels to give herself the advantage. When we kissed, I had to look up. She held my chin to look at her. I tasted her strawberry lip gloss and my eyes fluttered closed. Wow... It was tight and awkward in the bathroom, tiny and oddly shaped, but neither of us were very big anyway, though I was essentially a girl shaped storm. I unbuttoned the jeans he wore, made sure to pull them down to his thighs, made sure when I did it I was standing behind him and he could see himself in the mirror in my peach colored panties. Be blushed. I bit his neck. This was going to be so much fun. Luna’s teeth sunk into my neck and left a small purple mark. That I belonged to her. She would leave hickeys on my neck whenever she felt possessive, and I could never once stop her. I saw in the mirror as her hand drifted over the waistband of my peach panties and I gasped. Mm... “Luna...” “Miss Luna,” I corrected him, and ran my fingers up the front of his panties when I said it to silence any arguments. Nice and smooth, because I made him tuck the way I learned about online. Smooth like a girl. My fingers pressed and pushed and I whispered in his ear. “You keep saying you’re a boy, Sunny, but I don’t feel anything here at all...” One nice side effect was that when I teased him and taunted him, his taped down boyhood would leak between his legs. And I’d tease him more for “getting wet”. “I am a boy, Miss Luna,” I muttered quietly, less sure of myself every day I spent with her. I could live full time as her sissy boy if I wanted. But the idea of going to work like that terrified me. Or what if my brother found out!  No, this was private.  Private between me and her, and... 500 passengers on the plan. She pushed between my legs and I whimpered.  Her touch always felt amazing. “You don’t feel like a boy to me... maybe you’re just confused, Sunny? Maybe you need help seeing what I see?” I moved my hand up his hips to the cute little pastel top I’d had him wear - androgynous enough without a bra underneath anyway - and I tugged it up up over his tummy, up over his nipples. “When we get to the island, we’re going to get your tummy pierced.” I ran a finger around his navel as I spoke. “And get you some pretty bikini tan lines that no boy would ever have...” “Miss Luna, please don’t... I have a meeting next Monday, if anybody...” My voice trailed off into awkward whines. Was she serious? It was impossible to tell with her. I would wait until either my belly button was pierced or I was on the plane home. A whole week of this... her constant teasing... could she keep this up for that long? “Please, Miss Luna. I’ll be good.” “A good what?” Oh man, was I embarrassed. The boy in the mirror, in his tight panties, his revealing nipples, and round, pink cheeks... I sure didn’t look like a boy... “A good girl, Miss Luna...” “God I love you, you little airhead.” I pulled the top up over his head and dropped it adjacent to the sink, leaving him in only his panties, standing in front the mirror from which he couldn’t escape. “Do you want to wear my dress, Sunny? Do you want to be allowed to wear my dress and walk back out into the plane, walk allllll the way back to our seats where everybody will see and know what a little sissy you are?” My words weren’t malicious. I knew what worked for his long denied and tortured libido. I looked at her eyes, milky brown and shining with excitement. And I was so nervous. Walking back down that aisle, everyone gawking, calling me a sissy girl, and all the humiliation that went along with it. Automatically, before the consequences could form in my mind, I had already agreed. “Yes Miss Luna. Please may I wear your pretty dress, even though everyone will see me?” “Tell me what you like about it. Tell me your favorite things about it.” I was taller than he was with the grace of my heels and I made sure to stand behind him while I spoke, using his body facing the mirror to obscure mine. There were secrets beneath this dress that he needed to be kept from knowing until the dress was off my dainty shoulders and settled down on his. “It’s.. pink and feminine. Unmistakably. And only a girl would wear something like that. I like the straps and the frill at the bottom and how it accentuates your breasts even though I don’t have any and... and it’s yours and I want to dress like you Miss Luna. Please...” He took my breath away, he really did. We always described this as something we did for him, but it would be a bald faced lie to say I didn’t love it. I took his hand with his painted nails that the gate agent had stared at on the way in, and guided it to his borrowed panties. “Just like I showed you, one finger right down between, touch your cunny, Sunny.” To inspire him to do just that, to rub his restrained boyhood like a girl, I began to pull the dress off the top of my head behind him, revealing the bra that he’d soon be wearing. One finger, exactly where she told me to. A special spot where girls liked to be touched. It took me a little while to figure out the right thing to do, but I had months of practice. I pushed and rubbed with only my index finger against the satin, dampened panties. I was so distracted, I never even noticed Luna undressing. The first time he noticed me was when I needed his arm to push through the strap of the bra, but before he could complain about it I directed him to continue his touching. And he did. Eyes fixated on his chest as the padded bra cupped his soft skin and shaped what wasn’t there into the illusion that something was. I tugged taut, made sure he could feel it, clasped the hooks and let it snap against his lower back. Boys didn’t wear bras. Ergo, he wasn’t a boy. His eyes were more interested in his lace cupped chest than they even were in my naked one. So sexy. The dress would be next, and then something very new. Something I’d yet to share with him. My breathing was heavy and uneven. Every few moments, I would close my eyes and imagine Luna on her knees, with her lips around my... I bit my lip and shook my head. I was a girl.  Her girl.  She would never get on her knees for me, and she would never put her lips on a part of me that I didn’t have.  The admission that my manhood was not only locked away, but gone, was… overwhelming.  My orange satin panties were dark between my legs. I dropped the dress over his head. I pulled down his borrowed jeans. I left his panties for a moment longer and then tugged those down, too, breaking the spell of his touching with firm words. “You made these so wet, Sunny, soaking wet with Sunny’s cunny hunny, you must be such a girl, girls get wet and the wetter they are the more girly they are. I bet you wanna get even wetter, don’t you?” Even if he could have seen me from his angle, I doubt his unfocused eyes would even have noticed that I was wearing a diaper. A diaper damp and warm with my own arousal.  A diaper I’d be making him wear in only a few more moments. “Mm..” Luna took me by the chin and looked into my eyes. I was still shy, but tempered to her words. One strong swing and she could shatter me. And that’s exactly what she did. “Uh huh, wetter, more girly...” I didn’t know how much the fact I had broader hips and bubblier butt would impact the taping job I’d done on myself when I pulled the diaper up his legs. But his thighs were thicker and his waist was enough for it to be a remarkably snug fit. And enough for me to tease him about. “It fits so well, you must be becoming more like me, Sunny, more of a sissy and less of a boy, a cushy bubbly behind and pretty hips for all the boys to stare at.” I knew he liked that. I knew he didn’t have any attraction to guys, but he was thoroughly smitten with the idea of them objectifying him. Wanting to have him. Defile him. I was sparing when I pulled that string because I didn’t want to wear out the note. Besides, I had more to go on now. “You’re so girly and wet that you need this, you need proper panties to soak up all your girlish hunny, don’t you?” A... diaper? I didn’t understand. She was wearing only a moment before, but with some tight wiggling, managed to slip it off her hips. But why was she wearing it at all?  Why did she slide it up my legs, and why did she try so hard to pull it into place on me? I didn’t wear diapers. I didn’t need a diaper! On instinct, before the thought even came to my mouth, my hands tried to undo the tapes. It only barely fit anyway.  Obviously she made a mistake. I took his hand and moved it from the tapes to down lower. I pushed - helped him feel that he could still touch himself like a girl - and made a very clear distinction. “You’re a lusty little slut, my airheaded little sissy. Far too wet for grown up panties. The wetter you are, the girlier you are. How girly can you be? How much of a sissy will you be for me, Sunny?” I let his hand go. Let him run his course. I was completely naked in front of him. Even after a year, Luna’s body was a work of art. Small and simple. Subtle curves.  Almost plain, if she wasn’t so radiant, like an angel. Almost childish, if you couldn’t see past her hairless skin and into her mischievous eyes. Luna made me stop in my tracks when she was fully undressed, and she knew it. Her lips touched mine. Softly. Testing me. Waiting for me to make a decision. Her, or a diaper. What was more important? What did I want to focus on?  I kissed her back and touched the soft plastic between my legs. “If you’re not rubbing hard enough for me to hear you crinkle like a a fairy, I’ll stop kissing you.” There was nothing romantic about the plane bathroom. Nothing romantic about the way he pushed me back onto the commode once my kisses had combined enough with his touching and made him passionate and wanton. But it didn’t matter about the venue, because we were the very essence of romance itself. A knock on the door brought me out of my stupor and I blushed furiously. I had been grinding my padded crotch into my girlfriend’s knee when it happened. And worse yet, she pushed me off and started getting dressed. “Wait, wait!” I whispered. “Please, Miss Luna, don’t stop now, please!” But she had already pulled on my wet panties and tight jeans. This... this wasn’t fair!!

      He was still whiny when I pulled him out of the bathroom.  While I adored the way the traveler eager to use the restroom looked at us, Sunny looked mortified. Good. In his new dress; the first of many, and his diaper; the first of many, and his bra; a new norm, he was pretty enough to eat up. That would have to wait until we got back to our hotel, though. I sat down in my seat by the window, feeling the stares and whispers of the passengers. Was my dress too short? Had the tights bunched up? Or did I crinkle when I walked? Did they know I was wearing a diaper? Were they laughing at the sissy boy, or the baby sissy boy?  I was almost in tears when Luna leaned in and kissed me on the forehead. “Shh,” she told me. “You’re my good little girl. They don’t matter. You’ll be getting the reward tonight, not them.” Her words warmed my heart and I pushed my face into her chest just as she put her palm on the front of my dress, crinkling the ill-fitted diaper. “And the wetter you are when we get to the hotel, the better the reward.” The wetter I was? Well... I could think of a few ways...