Long Walk Home

Hello there dudes and dudettes.

Here is a new caption for all of you lovely supporters!

I hope you enjoy it, and we will see each other next week!

Until then stay safe, happy, and healthy.

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"Come on sis, you can`t be serious, right?" Jack asked his sister Charlotte, looking at her pleadingly.

"Oh, I am dead serious, sis" Charlotte said, glaring at her brother. "But this outfit is so..." the brother began to mumble from the passenger seat while pointing at his attire.  "Feminine? Sexy? Revealing?" his sister answered. "It is supposed to be after what you made me go through!" she said more heatedly, making Jack cover from her glare. "But I said I was sor-" "Sorry doesn`t cut it this time! Now unless you want our parents to find out about your smoking habits you better move your cute little butt out of the car!" she shouted. "...Okay..." the brother answered, hanging his head in shame and opening the car door.

Jack`s troubles began a week ago when his sister just got her driver's license. Their parents were away on a cruise for their wedding anniversary, and they left Jack in charge. When Charlotte got her license she wanted to go out with some of her friends for a drink to celebrate, but she also knew she could not drive herself if she planned to drink. So she asked her brother if he could pick her up when she and her friends were done celebrating, to which he agreed, happy to get the house to himself for a few hours.

Once his sister was out of the house Jack immediately began to do what he always does when he is home alone: He rolled himself some spliffs and began smoking one after the other, deep in thought.

He was only pulled out of his happy little trance when the front door smashed open, and he quickly tried to hide his pot when he saw his sister come inside. "Where were you?!" she screamed, looking furious. "I tried to call you for hours!". Jack just looked at his phone sluggishly, seeing over a dozen missed calls. "Well, you see, I-" he began before he was interrupted by Charlotte. "Where you smoking?" she said, sniffing the air. "You totally were! I can`t believe it, you rather get drugged up than drive your sister home as you promised!" she screamed at his face.

"So what? It could not have been that bad." Jack tried to defend himself, but his remarks just made his sister angrier. "Not that bad? NOT THAT BAD?!" she began, looking ready to strangle him. "The ride to the club took nearly 20 minutes, the walk home took nearly 2 hours. 2 HOURS! IN HEELS! TROUGH THE SEEDIEST PART IN TOWN!" she seethed, making Jack turn away in embarrassment before she stormed off towards her room, slamming the door shut.

The next day Jack was preparing breakfast, and when his sister came down she did not say a word to him, only silently sitting down while grabbing her breakfast. "Come on sis, you can`t seriously still be mad at me for yesterday, right?" the boy asked. "Mad? No, I am not mad, I am fucking furious!" she spat. "Really, you still are hung up on that? Fine, how about I drive you to the mall or something to make it up to you?" Jack said, hoping to get on his sister's good side again. "Oh no, brother, this will not be enough. I want you to experience the same thing I did!"  Jack raised his eyebrows. "So you drive me to the club and I walk home? No big deal, let`s go." "Not so fast" began Charlotte. "I had to go the whole way in a party dress and high heels, so you have to do the same" she continued with an evil smirk. "Forget it" was Jack`s immediate reply while shaking his head. "There is no way I am doing that." "Are you sure?" his sister replied, still smirking "Because I think our parents would be really interested to hear about your little smoking habit".

Jack, knowing that his parents would ground him for months if they found out, was left with no choice but to agree, and his sister immediately dragged him to the bathroom with glee. "Strip" she ordered, and Jack complied, knowing that he was in no position to talk back. Once he got out of his clothes Charlotte grabbed a few dozen waxing strips, covered his whole body in them, and started to rip them off, making Jack howl from the pain. "Don`t be such a baby, bro" his sister just said while rolling her eyes, never once stopping. After a few minutes Jack was completely hairless from the head down, and his sister applied some lotion to his red skin, making it smooth and smell like flowers. After that she grabbed some breast- and hipforms she had from a drama play at school and used glue to attach them to her brother`s body, giving his thin frame some womanly curves. Lastly, she slathered his willy in glue before pulling it back between his legs, giving him a flat front.

"Time to get you ready, Jacky!" Charlotte said with a giggle, leaving the room and returning a few minutes later with some clothes and heels in her hand. First she rolled some sheer lace panties up her brother`s legs, making sure to tease him about his flat front, before doing the same with sheer nylon stockings and attaching them with a garter belt. Next she grabbed a bustier corset which she attached around his torso, before tying it as tight as possible, making his new boobs and ass pop with his now small waist. "You clean up nicely, sis" she teased while looking at the transformed body, making Jack glare at her through the tears of pain from the tight corset. The next piece of the outfit was a black, thigh-length dress with a transparent boob-window which Charlotte pulled over her brother's head, making sure it was sitting just right. The finishing piece was a pair of black 5-inch heels which she crammed onto her brother`s feet.

"And now to make your face match your body" Charlotte said, smiling at her brother as she emptied her makeup bag in front of him, watching his eyes go wide. She started by applying a large layer of foundation on his face, making sure to use the right skintone, before moving on to his eyes. She started by covering his eyelids in a light blue eyeshadow before gluing on some big fake eyelashes which she covered in heavy mascara. After that she grabbed her tweezers and plucked his eyebrows, turning them from caterpillars into thin feminine arches before continuing with his lips, coloring them with nude lipstick. Charlotte finished her brother's transformation by clipping on some hair extensions and using a curling iron to put curls into the ends, framing his face in femininity. She then put a silver chain qround his neck and a watch around his wrist before handing him a pair of sunglasses.

"And, done, what do you think, sis?" Charlotte said while showing Jack a mirror. His jaw dropped as he saw his reflection, not believing that the sexy woman in front of him was himself. "Ha, speechless! But I agree, you look stunning!" his sister said, teasing him again. "Now get your pretty little butt moving, we have places to be" she continued, giving his ass a small smack before leading him to the car and dropping him off at the club.

Charlotte looked on with interest as her brother stepped out of the car. He was still standing right beside it, looking around nervously and wobbling a bit in the heels, unused to the footwear, while gripping the hem of his dress. And that was when she noticed it: In his nervousness, her brother managed to jam part of his new black dress inside the door, and he apparently did not notice it. This gave Charlotte a devious idea, and with an evil smirk she started to rev up the engine. "Should I really do this?" she asked herself, and the answer came immediately. "Yes, I should!". And with that she released the break and sped off. Even over the sound of the engine she could hear the Zrrpp as the black dress was violently ripped from her brother's body, and she could even hear a high-pitched shriek. Looking into the rearview mirror she could see her feminized brother, now only in his underwear, desperately trying to cover his body with his hand while guys approached him or took photos. "Have fun, sis" Charlotte thought to herself, unable to hide her glee. "I bet you can easily find a guy that will give you a ride in this part of town. But I doubt it will take you home!" she snickered to herself as she drove off, leaving her half-naked brother alone for a long walk home.