He can "earn" it...

The text came back almost immediately. So fast, he was sure she was using magic. No human could type that fast.

“So my dear sweet sissy needs some money, fortunately for him, I’m very generous so very generous in fact that I will offer you a continuing deal. You can earn money very easily just by picking a card to level up! Level two gets you $50, three gets you $100, four is $200, and if you level one to max I’ll send you $500. Oh and just for fun you can get $100 to draw a random card from the deck and $150 if you agree to level a card at random!

With love,

Your wonderful sugar mommy The Witch”

He stared dumbly at his phone for a full minute. He felt the air conditioning flutter his new skirt. Cum slowly slid down his leg. He could just pick a Level One card to move to Level Two and pay for his new makeup, finishing the challenge, maybe even with some cash to spare. But then he looked at the cute bras and panties Darla had picked for him, imagining their silk wrapped around him.

He quickly typed “Sweet Speech from Level One to Two and Two to Three please.”

The witch sent back a heart emoji and then he got a notification from his bank app. Opening the app he saw a transfer of $150 he clicked accept and then just like before time paused. This time however Sweet Speech glowed in front of him and two lines of text appeared.

SWEET SPEECH Lv. 2: Justin must speak politely and in a feminine manner. His voice has a natural feminine pitch and tone. He can overcome this with great effort but only temporarily.

SWEET SPEECH Lv. 3: Justin must speak politely and in a feminine manner. His voice has a natural feminine pitch and tone. He will not notice this unless it is pointed out and even then will only be able to stop speaking like this as long as he is actively thinking about it.

He sighed and then nearly jumped as he heard the new pitch of his voice. It sounded so dainty. He looked at himself in the mirror. Skirt sitting around his waist, secret lingerie underneath his clothes.

Just for a second he had the thought: If only I looked a bit girlier, I could really rock this skirt. His dick sprang to life at the idea but he shook his head, unsure what had come over him. He was doing this to get rid of the witch’s changes. He definitely didn’t want more. He picked up the bra and panties sets and slipped out of the changing room only to nearly run directly into Darla.

“Oh sweetie, how were the bras? Did they fit? I was worried they might be too tight.” She asked, getting right up close to him.

“T-they fit so well. Thank you for picking such cute ones Darla, you’re a treasure.” he responded barely even registering his voice’s soprano register.

“OMG are you doing voice training sweetie because that’s so good. You sound so pretty.” Darla squealed with delight. Then she looked at his legs and seemed to notice his skirt for the first time. “Oh honey you didn’t tell me you wanted a skirt it looks super cute on you though.”

The praise was starting to be too much for Justin but fortunately two previous ejaculations meant that his little dick only got hard and he was able to avoid cumming all over his panties for a third time in under an hour.

“Here let's get you rung up, do you know what your budget is now?” said Darla, taking the bra and panties and leading Justin over to a register.

“Yeah, I have about $150 from her and then about $20 of my own money. She also said I can, um, message her if it’s not enough.” Justin explained, his face glowing red at the thought.

“Oh you have such a generous friend, sweetie, maybe give them a little fashion show as thanks when you get home.” Darla said as she scanned the items.

“Looks like you have enough though, total is $152 and I’m throwing in the skirt for free as long as you promise to keep shopping here sweetie.” Darla said pointing to the register display.

Justin nodded dumbly, relieved that she had come up with her own explanation for why he was suddenly wearing a skirt instead of pants. He took out his card, scanned and then found himself standing outside of the store slightly lost about what to do now.

After a moment, he scampered for his car and luckily managed to reach it before he heard the witch’s voice in his ear again. “Good job gurl I’m impressed. That Darla seemed so nice too, lucky you she thought you liked this.”

Justin gulped, he could never say it but he really wasn’t sure that he didn’t like this… or at least that he wasn’t starting to.

“Well you passed! Now you get to swap a card, ditch a card and your next one starts at Level Two or go double or nothing.” she continued.

Justin looked down at the skirt, he couldn’t go back to his dorm in it, they would definitely see. He could just risk the next card being higher level but a little voice in the back of his head whispered to him “That’s a potential $50 you’re throwing away.”

“I-I’ll swap with a new card,” he stammered out. “Get rid of Cute Curtsy.”

“Aw but you looked so cute in your skirt. Well we’ll get you there soon enough.”

Light particles seemed to fly out of Justin and form into a card again and the deck reappeared. Cute Curtsy shuffled itself in and Justin noticed his skirt had turned back into the jeans he had worn in. He reached out to the deck to grab a new card and flipped it.

The picture was a person shrinking and the words read Weakling Waif. As it dissolved into light and entered into Justin he could feel it changing him.

This was the first card to actually change his body and he noticed as he lost at least 2 inches of height and his arms began to become thinner. He pulled up his shirt because his stomach tickled and saw that instead of his light six pack his stomach was now smooth and soft. His legs shrank too just by an inch or so but now the pedals of his car were out of reach. His purse now seemed heavier as he looked over his new shrunk body.

This was possibly going to be harder to hide than the skirt. Yet as he had that thought he could feel his little dick twitch once more with excitement. He looked at the rearview mirror and couldn’t stop his brain from asking a simple question. Would Trent think he looked cute?

CARDS LEFT IN THE DECK: 46

CURRENT MONEY: $21

CURRENT TRANSFORMATION:

LOVELY LIPS Lv. 2: Justin's lips have noticeable filler making them look plump and kissable. He also feels a compulsion to wear noticeable lipstick at all times. Justin will feel happiest when wearing lipstick he thinks of as cute.

LUSCIOUS LINGERIE Lv. 2: Justin does not feel comfortable unless he is wearing a matching bra and panties. Additionally he will feel drawn to wear pairs he considers cute. He can take them off to sleep and shower but otherwise will feel an intense need to wear them at all times.

SMOOTH SKIN: Justin can no longer grow hair anywhere other than his head and his eyebrows.

SWEET SPEECH Lv. 3: Justin must speak politely and in a feminine manner. His voice has a natural feminine pitch and tone. He will not notice this unless it is pointed out and even then will only be able to stop speaking like this as long as he is actively thinking about it.

WEAKLING WAIF: Justin will lose both height and muscle mass until he has the strength and height of an average woman.

HANDBAG HABIT: Justin will use a purse to carry his belongings at all times. He will not notice this is unusual unless someone points it out to him.

Any suggestions for challenges, changes, level ups, or things you want Justin to do are welcome!