A commission for WildCirno
It was four forty-five in the afternoon on Friday, and Sheldon, like most of his coworkers, was waiting for five o'clock to hit so they could all go home. So that meant he was mostly just sitting there watching his coworkers walk back and forth throughout the office.
Most of his coworkers were female, and Sheldon couldn’t help but stare at them, not because he was a sexist womanizer, but because he admired them so much. All of them were beautiful in their own ways, and all of them had such unique ways of dressing.
Seeing them always made him quite happy but also envious. He wanted to be able to dress like some of them. To be able to wear a nice skirt with a soft, cute blouse, maybe even a nice pair of heels.
To just walk around like that in the office was his dream, but it could never happen. He was a guy, which meant he couldn’t wear that type of stuff at the office; if he did, he’d get into trouble or, worse, be fired.
So he just tried to ignore it, but on days like today, when he had no work left to do and was just waiting to clock out, he couldn’t help but admire them, thus bringing all those feelings back to the surface.
After watching for a bit, it was time to leave, so Sheldon stood up, tossed his coat over his shoulder and picked up his briefcase. He let out a sigh and then left the office feeling quite empty inside. One train ride and a walk a couple blocks later and Sheldon arrived at his apartment.
He was about to go inside when he noticed there were a couple of packages next to his door with his name on them. He was confused, as he had no idea what they were, but he picked them up and brought them inside with him as he went to his bedroom.
Sheldon placed them on his bed and went to take a shower. When he came back with a towel covering him from his chest to her lower regions, he looked at the boxes again. He still couldn't remember what he ordered, so he opened up the first box.
His face turned bright red as he unpacked a matching bra and panty set. Suddenly the memory of him ordering this came back to him. It was last week after everyone in the office stayed late to throw a party for someone who worked there.
During that party, all his female coworkers were wearing the cutest outfits, and the whole time Sheldon felt a heavy pressure in his chest as he watched them walk around in them. So that night after coming home, Sheldon had a few drinks and ordered a bunch of stuff.
Sheldon felt his face burn as he held the bra and panties, and it only continued as he opened the rest of the boxes. Every single box was from the same order, and all together it made up one very adorable office-themed female outfit.
Other than the bra and panties, Sheldon had ordered a long-sleeved blouse, a thigh-length leather skirt, a pair of two-inch heels, and lastly some easy-to-use makeup, like mascara. Sheldon put all the stuff on his bed and awkwardly walked all the packing to the kitchen to throw away.
He walked slowly because he was deep in thought about the whole thing. He was a bit ashamed of ordering all that stuff, but at the same time he was sort of happy. He really wanted to put it all on, but he was unsure; he wasn’t sure what would happen if he did.
He either thought he’d hate it and no longer desire to wear them, or he’d love it and would be devastated when he had to take them off. When he made it back to his bedroom, he stared at the clothes, trying to convince himself to just put them on.
In the end, he was able to do it. He removed his towel and grabbed the panties, slipping them up and letting them snap against him and tightly secure his package. Just with that, Sheldon already felt his heart fluttering and he loved how it felt.
That gave him more confidence, and he grabbed the bra and slipped his arms through it. He then stumbled around for a few minutes as he tried to get the bra clasped together. At first he just couldn’t figure out how to bend his arms; then it was just him clasping the wrong clips.
Once he had all three clasps together correctly, he looked down and smiled as he looked at the bra, which also made it look like he had a small pair of breasts. It was quite nice, but after looking at it again, Sheldon felt like he was still missing something.
It was obvious what that was, and Sheldon couldn’t do much about that, so he just grabbed a couple pairs of his socks and stuffed the cups with them. That little pressure from the socks stuffing the cups and pressing against his chest was comforting for him.
With the underwear on, Sheldon grabbed the blouse and slipped it on over his head, then he grabbed the leather skirt and slipped it up his legs and pulled it up over his waist. It was a bit tight, so he had to readjust and mess around with his blouse to make sure they were both on properly.
With those on, there was only one thing left for him to put on. So he sat on the bed, grabbed the heels, slipped one on each foot, and then secured them with the ankle bands. With it all on, Sheldon stood up and ran over to his mirror.
He stood there completely excited and happy until that feeling hit again. As Sheldon stared at himself, he looked down and realized that he could never be this; he could never be a woman. The whole room suddenly felt like it was dark and void of light, and Sheldon’s chest felt so tight and hurt.
He was nearly on the verge of tears, ready to collapse and fall deeper into depression, but then suddenly Shelly’s phone started beeping. Shelly lifted her head up and sighed. She slowly walked over to where she had left her briefcase but strangely found a woman's purse there.
Shelly tilted her head and asked where it came from. She didn’t remember unpacking it. As she stared at it, she heard a beep again, and things got stranger as it was clear her cellphone was inside the bag.
Shelly picked the bag up and looked inside. It contained a ton of stuff, including her phone. Shelly, without thinking, took her phone and slipped the purse over her shoulder, then she checked her messages.
It was a group chat with some of the office women, whom Shelly had never been in contact with outside of work before. Shelly looked over the chat history and saw a recent message about adding the cute new girl from the office, and then moments afterward she was added.
Shelly continued to be confused; did the women at her office know her secret? Shelly began to panic and try to come up with an excuse to convince them they were mistaken and nothing was going on, but one of the other women noticed she was online.
She then asked Shelly to take a picture of that cute outfit she was wearing today and then mentioned the white blouse and leather skirt Shelly was currently wearing. Shelly let out a gasp, wondering how on earth she knew about the clothes Shelly had just bought and put on.
Shelly held her head, feeling overwhelmed. She then sat on her bed and took a deep breath. She used the power button on her phone to turn it off for a moment, just to give herself time to think. As the screen faded to black, Shelly noticed her reflection looked off.
She knew she was wearing different clothes, but she didn’t use any of the makeup, so she should still look like a guy. So she turned towards her mirror to see if she was just seeing things. The sight of herself now was unbelievable.
Just a moment ago when she looked at herself, she saw a guy in women's clothing, but now the reflection showed off a cute woman who perfectly fit her outfit. Shelly’s face changed to excitement again, and she had to test if what she was seeing was real.
So she reached into her bra to see if she could pull out some socks, and instead of socks, she found her bra was stuffed with breasts actually attached to her. Shelly quickly took her hand out of it and then let out one of the happiest laughs of her life while she kicked her feet around in the air.
Once she calmed down, she thought about the chat messages. All of them seemed to already know she was a woman now, so clearly whatever transformed her changed more than just her body. To make sure, Shelly pulled out her driver's license.
On the license it showed her current body and her new name; along with that, in her photo she was wearing a cute pink sweater. Shelly’s smile got even bigger as she dropped her license and ran to her closet. She flung the door open and giggled at all the feminine clothes she found inside.
Everything she owned had changed, reflecting that a woman lived here instead of a man, and because of that, Shelly had more cute outfits than she could possibly wear, which was beyond amazing in her mind. Shelly made two fists and once again started to giggle excitedly.
She truly couldn’t wait for the next workweek so she could try on more of her office outfits. She was totally ready for it and every day to come, but before that, she had some new friends who wanted to see a picture of her, so she wasn’t going to keep them waiting.
Riley
2025-10-04 15:19:19 +0000 UTClast_of_workers
2025-09-23 10:32:07 +0000 UTC