Teasing His Old Body

 Source: https://www.pixiv.net/en/artworks/96771192

Teasing His Old Body

Chuck loved his older sister a ton, and he'd been sad when she went away for college. That's why he was super excited when his family was going up to grab her and some of her friends and visit a cabin for a few days. His parent's had invited his friends, but unfortunately they'd all been busy. So that meant he'd finally get to hang out with his sister a bit. What he wasn't counting on was her best friend Tiffany coming too. He had conflicting feelings towards her. On one hand she was a complete bitch to Chuck, never passing up an opportunity to make fun of him. Her kindest name for him and his friends was the "loser patrol." On the other hand Chuck thought she was the most attractive girl ever. He was so physically attracted to her it hurt, but his repulsion towards her personality left him at an impasse. His sister's other friends just ignored him but he knew Tiffany was going to make this trip hell for him. Just when he was debating faking an illness to not go he found the ring. The website promised that he could use the ring to swap two people's positions. It wasn't that expensive, and even if it didn't work the ring looked nice so Chuck bought it. He hoped its powers would put her in his shoes and stop the bullying for the week and packed it along with his things and got ready for the trip.

The cabin was in some sort of swanky resort town and turned out to be huge. Each person got their own room and Chuck found himself looking forward to the stay in spite of the company. Unpacking his things he scooped up the ring and made his way down to dinner. Chuck made sure to "accidentally" bump into Tiffany to activate the ring on the way down. She gave him a dirty look but didn't say anything further so Chuck just sat down to eat. Throughout dinner Chuck noticed things getting weird. It all started off normal enough, but as time went on his sister and her friends started including him in the conversation and tuning Tiffany out. Since she was the queen in every social circle she ran in this obviously baffled both of them. The girls started waiting on his opinions and were soon agreeing with things he said with "That's SO true" and "Of course you would know best." Chuck decided he liked being at the metaphorical top, it felt good to have pretty girls waiting on his every word. He loved the attention so much he didn't question why. Chuck finally realized something was off when Tiffany tried to interrupt him and his mother cut her off.

"I know none of your friends could make it, but you need to leave you sister and her friends alone." Tiffany made a face and started to talk back but his mother was having none of it. "I'm sorry Tiffany, why don't you girls go to be early, and Chuck here can help me clean up tonight." That's when the coin dropped. They all thought he was Tiffany. It seemed impossible but the he remembered the ring. When it said it would swap two people's positions he assumed it meant make her awkward, not have him take over. He decided he liked this development much more as he loved how differential everyone was to him now. Plus it made Tiffany seethe.

"It's ok Mrs. M, I know how boys his age are." Chuck made sure to Tiffany a wink just to piss her off more. Getting up the college girls moved upstairs with him at the center. His sister noticed his phone and quickly nabbed it.

"Looks like you picked up Chuck's by mistake. You usually never let that thing off of you, I'm surprised." She gave him a playful nudge. "Let me grab yours, I know you don't like to have contact with him." She soon returned with Tiffany's phone in hand and Chuck giggled at the expletives he heard from downstairs. "You must be tired Tiff, we'll be in Amy's room if you want to join us but we'll understand if you want to go to bed early." The other girls nodded, reassuring him. Chuck just nodded and found himself led to Tiffany's room.

"I'll be alright," he managed to squeeze out, entering a girls room for the first time. Not to mention the room of the hottest girl he'd met and his long time crush. He felt like going through Tiffany's things was an invasion of privacy, but some voice in his head whispered to him that they were his things, after all right now he was Tiffany. This made sense to Chuck and he began to unpack all of Tiffany's things, which turned out to be a monumental task as she had packed a ton of clothing and shoes for what was supposed to be a five day trip. Well, a girl's gotta look her best. Chuck paused when he got to the underwear, but didn't find them a turn on like he thought he would. Just as he finished putting everything away, his new phone chimed. He was wondering how to unlock it since he didn't know Tiffany's password, but his thumbprint unlocked it. Well, magic is certainly convenient. He scrolled her messages amazed at how popular she was. He finally got to his sister's message and a simple "Hey Tiff, shower is free" greeted him. He grabbed a towel and Tiffany's toiletry bag out of habit but froze. He didn't have anything else to wear. He grimaced as he realized he'd just have to wear some of Tiffany's clothes. He grabbed some underwear and what looked like pajamas and made his way to the bathroom. Amy greeted him in just a bra and panties and they exchanged some pleasantries before he entered. Once inside he realized how natural it felt. He'd just seen a pretty girl almost naked and not only did she not freak out, it seemed normal that they would talk like that. Chuck grinned to himself I could get used to this. He quickly stripped out of his clothes, something deep inside him glad to be out of something that didn't make him look cute in any way. As he conditioned and then shampooed his hair he felt it growing out, stopping at his chest. It felt like silk to the touch and looked way better than his old hair so Chuck decided he liked the improvement. Lathering up the loofah, he got to work on his body. As he scrubbed, Chuck noticed his body hair and acne vanished. His skin felt smooth and soft. He used to be proud of his body hair, but for some reason he was now glad to be rid of it. He dried himself off and moved to the mirror. He was surprised to see that his brown hair had darkened to a deep black and his hazel eyes and become bright blue. He also realized he'd gained a few inches of height and as he brushed his teeth he had to blink a few times as his face looked different. At first more like a girl's face, then he realized it had become the angelic visage that Tiffany used to have. Chuck posed in the mirror, giving himself a myriad of silly faces. He reveled in his newly attractive reflection. He finally decided he'd spent enough time admiring himself and started getting dressed. Slipping his panties up Chuck was surprised at how comfortable they were. He held up the pajama shorts. There is no WAY these fit. The narrow waist flared out drastically to fit someone with much larger hips, thighs and butt. But Chuck couldn't walk around nearly naked so he pulled them up. Of the many ways he expected the shorts to fit, snug was not one of them. Chuck turned to look at himself in the mirror and realized from the waist down he now had Tiffany's perfect curves. Chuck wriggled his new toes, marveling at the nail polish that had appeared. He spent a few minutes groping his new ass and thighs, enjoying feeling his hands sink into them. He'd always wanted to do this and now he had full access. He satisfied himself then realized he needed to finish getting dressed. As the pajama shirt settled into place Chuck realized he could no longer see his feet, as Tiffany's impressive cleavage now blocked his view. His new hands explored his cleavage and a soft moan escaped his new lips. It sounded so feminine and sexy. Looking at himself in the mirror it was clear to see why Tiffany had been so vain and why everybody worshiped her. Tiffany was gorgeous. And since right now he, no that didn't sound right to Chuck. With a body like this there is no way I'm a boy any longer. And Chuck is such a drab name, with a body this amazing it's only fair I get the name to go with it. I'm Tiffany now. The new woman grinned to herself. Feeling extra sexy she opened her phone and snapped a few selfies, posting them to instagram. Almost instantly her posts were flooded with likes and comments. She smirked to herself. She gathered her things to leave and realized that the clothes she had discarded had turned into the ones the old Tiffany had been wearing earlier.

As she stepped out of the bathroom she came face to face with her old body. It truly was ugly and pathetic. It was time for some payback. "Hey dweeb, what are you doing on the second floor, don't you know it's for us girls?" He felt a rush of power putting the new Chuck down. He looked like he was going to say something but her glare intimidated him. She then noticed a tent in his shorts. "Oh my god, look at you. You're so pathetic, just seeing a freshly showered girl is enough to get your nerd ass worked up. Well go on, get a good look." The new Chuck looked so ashamed and Tiffany grinned. "Now go on, scurry off to your room and masturbate like a good little loser" she ordered him. Chuck grabbed his crotch and left, clearly forgetting about confronting her. She laughed. This feels amazing. She felt a perverse excitement from humiliating her old body like that. She moved back to her new room, making sure to lock the door. She pulled up several instagram posts from some cute guys she was flirting with and quickly got to work testing out her new equipment. She reveled in the memories flooding in, and finally came with a muffled moan as she realized she had finally taken everything from the old Tiffany. She was now truly Tiffany and nobody could ever say otherwise.

3 Days Later

The other girls had whined when Mrs. M had made Kelsey bring her brother Chuck to karaoke, as that meant they wouldn’t be able to pick up any cute guys. Tiffany pretended to be as upset as the rest of them, but secretly she was thrilled. She had discovered the joys of teasing her old body with her new one. She loved seeing the look on his face as she brushed up next to him, or as she whispered in his ear. Tiffany felt a perverse thrill knowing that he would spend that evening masturbating furiously to her old body, powerless to stop himself knowing full well he had been the owner of that body but not remembering or able to say a single thing about being Tiffany. She made sure to sit across from Chuck and as her beautiful voice drew his attention to her, she slowly moved her stocking-ed foot slowly up his leg watching him squirm. It was only fair after the years of hell she had been through in that body that she got to have some fun at its new owner’s expense. When she got back to college she was going to have to find some new boys to mess with, as this was too fun to give up.