Part 33
Earn it, how? He had already done more than enough to humiliate and degrade himself. Of course, most of that was from before Julia slipped the cage on him. And Amy was clearly treating it as something separate from the ever increasing amount of leverage she had on him.
He just waited for her to explain. Talking like a girl still wasn’t something that came naturally, even if he was getting more and more used to it after being chastised every time he sounded like a boy.
“How about a trip to the mall?” Amy suggested, “You can borrow a pair of my heels.” They were basically the same size when it came to everything else, so it stood to reason that her shoes would fit him as well.
As in, going out in public. While looking like a girl. Even if the transformation was convincing, and they were in a city where he wouldn’t know anybody, it was still a daunting concept when he knew his actual gender despite the nonstop sissy talk.
“Don’t be rude, Chrissy,” Julia said, “Your cousin is inviting you to the mall with her. Doesn’t that sound so fun?”
Wincing slightly, he reluctantly responded in the feminine tone, “So fun.” He was way too flustered to outright demand the key, and knew it wouldn’t get him anywhere when Amy was having way too much fun with him being thoroughly under her thumb. What he really needed to do was find a moment to properly negotiate about the key, which he didn’t want to do in front of all three of the girls.
Amy smiled. “Then ask nicely, Chrissy. To borrow my heels, and to go to the mall with your favorite cousin in the whole world.”
Swallowing his pride, knowing full well that it was going to amuse Amy and her friends, Chris said, “May I please borrow a pair of heels, Amy? And can I go to the mall with you?”
“Hmm, I don’t know,” Amy mused, “Do you like girls, or do you like boys?”
“I-” Chris hesitated. How was that relevant? Not that it mattered. He knew what she wanted to hear, considering everything she and Julia had teased him about recently. “ . . . Boys.”
“Good girl,” Julia said. She was still standing behind him, casually holding his shoulders to keep him faced towards Amy and Sadie. “You like boys.”
“You like boys,” Amy echoed. Not being subtle in the slightest about this round of teasing/conditioning, she nudged Sadie with her elbow.
“Oh!” Sadie giggled, “You like boys, Chrissy.”
Amy stood up and pulled out Chris’s phone from her purse. She must have taken it earlier at some point when he was first being pressured into dressing up like a girl. Approaching him with a smirk, she held out the device and said, “I’m going to find something for you to wear. While we get ready, I want you to find thirty different cocks that you wish you could suck. And they have to be new. No using any of the dick pics already on there.”
Chris definitely wasn’t expecting something like that; it took him a moment to process the task that was said so nonchalantly. Putting aside the implication that he already had such photos on his phone, she wanted him to find thirty?! Even one was too many, when the last thing he wanted to do was look at male genitalia. Despite all the ‘hard cock’ references, he wasn’t actually into all that.
As usual, Sadie seemed particularly amused by everything the other two were throwing at him. It made sense, considering she was a little late to the party compared to Julia. “Thirty good ones, Chrissy!” she said, playing catch-up in terms of including herself in the fun.
“That’s right,” Amy smirked, “Sadie and Julia will judge them. I don’t want to know what my sissy cousin likes.”
With that, the three of them left Chris to figure out what constituted a ‘good’ dick pic. Before all of this, he would have judged them for heading up to Amy’s room as a group to get ready for a trip to the mall. He never understood why girls needed to spend forever touching up their make-up, accessorizing, etc. for an outing that was essentially running errands. He still didn’t understand it, but was grateful for a moment where he didn’t have to deal with any of them teasing/taunting him or making things worse than they already were as ‘Chrissy.’
On the other hand, Amy had set things up so it wasn’t really a break. The task she had left him with was impossible, too. Even if they took a full half hour upstairs, he’d need to find a new photo every minute, and it would have to meet the standards of the girls who actually liked guys.
Chris unlocked his phone, half expecting to find a collection of dick pics already in his photos app. But Amy didn’t know his password, and her tease must have just been a tease about what was already on there. He hesitated after opening the browser, not sure what to even search. When he looked up nudes of girls, he’d use words like ‘topless,’ ‘lingerie,’ ‘naked,’ etc. That didn’t quite work for the opposite gender, when he was specifically looking for shots below the waist.
After a minute of deliberation, as well as reminding himself that no one was looking over his shoulder and that he could always delete his search history, he went with ‘hard cocks.’ That was the phrase that was stuck in his head after so many iterations, including the frequency with which he had to say it himself about what he wanted in both his mouth and ass.
Wincing and averting his gaze at all of the results, which was his habit when it came to visually blurring out the male when it came to porn, Chris forced himself to actually look a few seconds later. That was the only way he’d actually get the inappropriate assignment done.
Looking at the first few cocks, he reluctantly saved one that was high definition and a lot bigger than he was down there. One down, twenty-nine to go . . .
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