Sissy Tori's Diaper Tale

by: Fahzbehn



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Chapter 1 Halloween. For many, it's better than Christmas. The idea that you can out, dressed however you like, and it's easily dismissed can make many a person brave. In the case of Anthony, or, as most called him, Tony, it would be where he found something far better that just a trick or treat. Tony looked at himself in the mirror nervously. How in the hell had Tiffany, his closest friend and confidant, convinced him to do this? He adjusted the long blond wig on his head and tugged the pink and white skirt down a little. From the front it looked okay, but he knew better. His slender, trim legs had been waxed and, while no one could see them inside the white sneakers, he had let Tiffany paint his toenails pink. Tony trembled a bit, thinking about that, and looked back at his crotch. There was no tell tale bulge, even though, looking at himself this way, he was exceedingly horny. He put the thought of why out of his mind, or tried to. Letting his eyes drift further up his body, he was still surprised by how busty he was. That had been a crazy chunk of change to buy silicon forms as big as they were, but Tiffany had been right: they looked fantastic. On his forty inch chest, they jutted out proudly. Glued to his chest, the silicon forms bounced and jiggled, filling the F-cup bra he was wearing underneath the rest of the pink and white "ABI" cheerleader outfit. Add to that, the makeup that Tiffany had taught Tony how to apply and the corset as well and you'd be hard pressed to tell Tony was anything more than a bouncy, fun, blond bimbo. He glanced back down at his crotch then turned to look at himself from the side. His eyes went to his rear end, which jutted out more than usual. As he leaned over, the skirt rode up and revealed the thick diapers underneath. Tony sucked on his lip and had to convince himself to not rub himself off until he came. When his doorbell rang, Tony jumped a bit. Grabbing the oversized pacifier hanging from a long pink ribbon, he slid the ribbon around his neck and tied it, the pacifier resting between his large breasts. Making his way to the door, he peeked through the spyhole. Smiling, he opened the door for Tiffany. Tiffany, a tall, buxom brunette, squealed in delight when she saw Tony. Dressed as a black cat girl, she quickly hugged Tony before stepping inside. Tony closed the door and smiled, blushing a bit. "For a sometimes cross dresser, you really outdid yourself, Tony." Tiffany smiled and walked around Tony, examining him. "I barely recognized you." Tony's blush deepened. He wasn't just a some times cross dresser. This was, to him at least, a test. He wanted to see if the world would accept him as a woman. It was, admittedly, a little over the top, but the outfit was complete fantasy. Tony turned and wiggled his rear, causing the diaper to peak out from underneath his skirt. Tiffany gasped then laughed. "So, you went the whole nine yards?" Tiffany asked. Tony nodded. "It's really too bad you're a guy, Tony. I'm so tempted to jump you right now." Tony wrapped his arms around Tiffany, his voice a throaty alto in falsetto. "What? Does baby kitty like girls with great, big, titties?" He grabbed Tiffany's ass playfully and groped her, the padding he felt confirming Tiffany had kept her half of the bargain. Both of them were adult babies and Tiffany had promised to wear a diaper under her outfit as long as Tony wore one tonight as well. Tiffany laughed and pulled away. "Well, as it's hard to get this thing unzipped easily, a little extra protection couldn't hurt." She gestured toward the door. "Come on. Time's wasting. We don't want to be late." Tony laughed and grabbed her bookbag, conveniently stuffed with his pompoms, a couple of extra diapers, some baby wipes, and a small bottle of baby powder... just in case. The lights from the fraternity house were as bright as the music was loud. It was all Tony could do to think clearly. The guy at the front door was dressed as a gorilla in a tux. When Tony and Tiffany got to the door, they were waved right in. Tony smiled at some of the guys as he walked in, but he was just being flirty. He actually wasn't interested in any of them. Much like Tiffany, Tony wasn't interested in men. Sure, he'd kind of thought about it, but, really, as a guy, it didn't appeal to him. Mother nature just hadn't provided him with the right equipment, in his opinion, to enjoy both genders properly. Tony rolled his eyes as Tiffany made straight for the booze. Tony was going to be the designated driver and, while the alcohol wasn't free, the sodas were. Asking for two, the girl dressed like a cowgirl, complete with ten gallon hat, smiled at Tony. "Don't let your friends drive drunk, K? Now, if I could just find my heifer." The woman looked around and Tony looked as well. Both of them saw the tall, buxom woman in the spotted bikini top, cowprint spandex pants, and big, floppy cow ears. The cowgirl waved her over and, once she was closer, offered the dairy cow a drink. Tony was about to walk away when the "dairy cow" touched his arm. "Cute cheerleader outfit. Can you give me a cheer?" Tony got a closer look at the dairy cow and tried to quickly avert his eyes from the woman's breasts which were larger than his fake one. "Um, like, sure. Like, what should I cheer for?" Tony replied, giving his best valley girl impression. The two women both giggled. "Um, how about milk?" the dairy cow suggested. "Everybody loves milk, right?" She cupped her breasts a bit, causing the cowgirl to giggle hysterically. "Give me an M!" Tony said, bouncing a bit. "Give me an I! Give me an L! Give me a... umm..." Tony affected a helpless look to the dairy cow, who mouthed the letter K. "Give me a K! What's the spell? MILK!" Tony raised his pompoms high in the air. The cowgirl simply smiled and the dairy cow clapped, her eyes dancing. "Very good. If I need another cheer, I'll definitely come look for you." With that, she walked away. Tony continued to mill and mingle, but, after a few hours, he was certain of three things. First, he'd been hit on by every guy in the place. Second, he couldn't find Tiffany at all. Third, if he drank any more soda, his diaper was likely to leak. He began to ask around, because he didn't feel comfortable going into either the men's or women's bathroom alone, and, finally, someone pointed toward a door upstairs. Heading up the stairs, he caught sight of the rear of the dairy cow from earlier just before she entered the room he was heading to. Quietly peaking into the room, he was surprised to see Tiffany, her hands on the wall, as the dairy cow unzipped the cat suit. "Yep, you need a change, kitten. You should've asked them to send me up earlier. What, did you except your new girlfriend would leave the party to change you." "Sorry aunt Mary. I promise, I'll be a... I'll be... a good... um... what were you saying?" Tiffany stammered, obviously drunk. "Oh, yeah. I need my diaper changed. But I don't have any diapers. Tony's got them in his book bag." Mary, the dairy cow, helped Tiffany down onto one of the beds. "Well, then, little lady, maybe I should go find him. What's he look like?" Tiffany giggled and tried to paw playfully at Mary's breast. "Oh, he's easy to spot. Pink and white cheerleader outfit. Diaper underneath. Can't miss him." Mary stepped back and smiled. "I thought that was a diaper, but the cheerleader is a guy?" Tiffany pointed a finger at Mary. "Hey... don't get... any ideas. He's really nice. He's a big sweety... and a big baby, too." She looked around. "Hey, do you have... you know... something to drink?" Tiffany waggled her brows. "You were always such a nice cow." Mary put her fingers to Tiffany's lips. "Hush. I do, but you broke me of being a submissive, Tiffany. You haven't earned that treat." She turned toward the door. "Now, don't go anywhere. I'm going to go find Tony. That's his name, right?" Looking back to Tiffany, Mary shook her head as the woman was passed out. She should be okay for a moment as the soaked diaper would be enough to throw off almost anyone who got the wrong idea. Tony rushed from the door and paused at the women's bathroom just as Mary exited the room. "Hey, are you Tony?" Mary called. Tony nodded back. "Great! Tiffany said you had a special package in case her... costume was about to spring a leak?" Mary smiled to herself as Tony walked over. "Great costume, by the way. I just love the tits, though, your special panties are a nice touch. Alpha Beta Gamma. It's not quite ABC, but cute joke anyway." Gently shoving Tony inside the room, she locked it behind her, muting most of the outside music. "Tiffany's diaper is soaked and I'm afraid she'll leak at any second." Tony peered over and then offered the bag to Mary, feeling quite shy. "Oh, isn't this the cutest diaper bag. It even matches your outfit." Tony blushed bright red as Mary turned away and began to change Tiffany's diaper. Tiffany moaned a bit, though, it was hard to tell if that was from the alcohol or Mary cleaning her. Finally, the clean diaper was on. Tiffany's head rolled to the side as she began to snore. "Poor dear, all tuckered out." Mary turned and smiled at Tony. "And how about you? Does Tiny Titty Tony need her aunt Mary to change her, too?" Mary's hand shot forward, cupping Tony before he could stop her. "Mmm... definitely wet." Tony moaned as Mary rubbed his cock through the warm, wet diaper. "Definitely need aunt Mary to change you, don't you sweety? Such a cute widdle baby." Mary lisped. "Do you want aunt Mary to help you out of that dress, sweety?" "Yes, please," Tony squeaked out. "Yes, please, aunty Mary." Mary corrected him, swatting his wet, diapered behind playfully. "Yes, please, aunty Mary. Please help me out of my dress." Tony's heart raced. This was not what he expected by any stretch. Further, that Mary, the sexy milk cow, was Tiffany's ex? Obediently, he moved so Mary could help him out of the skirt and top, his pink, lace and silk bra still lifting his F-cup falsies. "Now lay down, like a good girl." Mary instructed. Once Tony had done so, Mary untaped the sides of the diaper. "Wow, you're soaked, sweety." Tony lifted his hips, allowing Mary to withdraw the diaper and begin to clean him. She smiled as Tony twitched while she cleaned his cock. She diapered him again, but, when he went to move, Mary shook her head. "You've been a good girl for Aunty Mary. It's time for your treat." Mary wiggled out of her spandex pants and panties before pulling the diaper down just enough to free Tony's cock. Mary climbed over him, slowly lowering herself around him. "Such a nice big sissy-cock for me." As she began to rock, her hands went to Tony's silicon tits. "You like that, baby doll? Do you wish you had big titties like these for me to play with?" Tony moaned, his head spinning. Lost in the moment, he admitted his secret truth. "No, aunty Mary, I want bigger ones. I want big titties like yours." His eyes widened as Mary reached back untied the bikini, her head sized breasts bouncing freely, white droplet forming on the tips. "Mmmm... I may just keep you," Mary moaned, leaning forward so her breasts hung in Tony's face. "Go ahead. They're really full, baby doll. Suck on my titties and then cum inside my pussy. Aunty demands it." Tony reached up, his hand guiding Mary's breast, his lips finding her nipple. Suckling, he felt his climax nearing, goaded on by Mary's moans until, in a moment of extreme pleasure, his body tensed. His cock twitched inside Mary, only to hear her cry out, her pussy clenching around his cock. Mary rolled over and slid away from Tony. "Oh, yes... definitely a keeper." Reaching for a baby wipe, she quickly cleaned herself off before pulling her costume back on. "I think I want to keep you just like this, so you have something to think about." Tony blushed as Mary pulled the diaper back over his cum covered cock. She wrote something down as Tony pulled the cheerleader costume back on, the folded it up and shoved it down Tony shirt. "You'd such a cutey. I'd like you to consider being my baby girl again. When you get home, email me. If you're serious, I want to see a picture of you wearing the thickest diapers you can. Only then will I set up another... play date." Mary smiled and moved over to sit by Tiffany. "And don't worry about her. I'll get her home. I promise." Tony got up slowly, grabbed his backpack and made his way to the door, the party outside almost forgotten. He quickly made his way through the party and to his car. Sitting down, his head spun, trying to get a grasp on everything that had just occured. Had he just admitted he wanted huge tits? It was true, but to tell a woman, an unbelievably hot woman, that this was what he wanted? A small part of him whispered "Like, no, silly. You want even more." Putting the car into drive he raced home. Once there, his fingers fumbled with the lock, finally managing to get inside. He looked at what he was wearing and smiled. Wiggling out of the skirt he knew just what to do. He went straight after his baby stash. It took him almost ten minutes, between adding layers: two additional diapers, the same size as the one he was wearing at the party, followed by two larger ones he had from a previous experiment. Add to this an oversized pair of pink petti-panties he'd ordered but found too large before. He looked at himself in the mirror as he struggled to pull the cheerleader skirt back over his thickly diapered crotch and ass, then smiled when he realized there was no hiding it. Tony put the pacifier from around his neck into his mouth, sucking on it quietly. As he couldn't walk with that much bulk between his legs, he waddled over to his PC and turned his web cam on. Looking around, he spotted a pair of barrettes and quickly put his wigged hair up in pigtails. Setting the camera to take pictures every five seconds, he grabbed his pom poms and posed. Minutes later, he had sent a dozen pictures to Mary. For a brief moment, panic filled him, thinking she may just use these elsewhere, but a quick reply calmed him: "Good girl, I want to see my baby girl tomorrow, bright and early, so she can spend the day with me. I have big plans for my baby girl. Come dressed as a boy, but be diapered and bring those nice boobies you have. Here's my address. Also, if you want to truly show me you want to be with me, I want you to wear those diapers to bed and just as many when you come to see me tomorrow. LOVE Mommy Mary" Tony looked up the address and realized it was a condo in a very nice part of town. Looking around, he spotted a large pair of white sweat pants. He figured they should be big enough to fit, though, the diaper bulge? There was no way to hide it. Making his way to the bathroom, he took off the wig and cheerleader outfit before carefully ungluing the breast forms and putting them into their carrying case. He waddled back to his bedroom and put the large, F-cup bra he'd worn for the night into the laundry basket and took off the corset as well. Breathing deeply, he rubbed his ribs a bit. He still wasn't used to the corset. Once he was breathing better, he reached into his dresser for a purple chemise he'd stitched foam breast forms into. They still gave him nice sized breasts, maybe a C-cup, but no where as large as he fantasized. Slipping into bed and turning off the lights, his hands wandered to his crotch and fake breasts, fantasizing about his upcoming play date with Mommy Mary.

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