5 Childhood friend

Jack had to find a job as a "hero"; he always dreamed of being a hero, but he couldn't compromise his identity and had to be available for Rika and Brandon whenever they wanted, so instead, he became a vigilante.

Every night, Jack would put on a homemade superhero that resembled the one of the Man-Bat and patrol the streets. 

One night, as he patrolled the streets, he had a deranged idea, even more than the others he had.

'What if I make Brandon a mafia boss? That way, I can have him fuck other superheroines and have his henchmen fuck Rika and my future women too.' Jack thought as he beat a mugger in a dark alley; after finishing the poor robber, Jack stole all the man's valuables and returned them to their original owner.

Jack kept the rest of the things he stole to sell them later and give the money to Brandon.

After a long night of patrolling the streets, Jack decided to go back home, but on his way home, as he jumped through the ceilings of his city, he spotted a young woman he knew very well.

'It's Ashly! It's been years since I last saw her. She and my sister used to be such good friends, and I had a crush on her...' Jack thought as he descended from the ceiling; after getting closer to Ashly, he noticed she was wearing a hero uniform.

Ashley was a red-haired woman, extremely tall, standing at 6 feet, and had big breasts for her size, but her most prominent feature was her pump ass.

Jack also noticed Ashley had a camel toe on his hero uniform, but he chose to not say anything.

After coming closer to Ashely, Jack immediately used his hypnosis on her. "You must obey," Jack whispered into Ashley's ear; Ashley immediately stopped and fell like a marionette whose strings were cut from his puppeteer.

"From now on, whenever you talk to me, you'll speak only the truth and nothing but the truth; also, you'll follow my every command no matter how deranged it is." Jack snapped his fingers, and Ashely came back to normal; the moment she noticed Jack, her face brightened up, and she went for a hug.

"Jack! It's been so long! Oh, sorry, you are in uniform too," Ashley said as he pulled Jack into an alley to talk more privately. "Jack, it's so good to see you again! After you became a neet, I lost track of you, I tried spying on you, but your sister told me to stay away... that slut, I never liked her; I only hung up with her to be with you!" Ashley said with a smile as she hugged Jack once again.

"Yeah... nice to see you again, Ashley; you grew a lot," Jack said as he felt Ashley's breast pressing against his face due to the height difference.

"I know, right! I masturbated every day thinking about you!" Ashley said as she pulled out of the hug. "So, how is Rika doing, Jack?".

"Well, I used Hypnosis on her, and now she is addicted to sex with my bully," Jack said, awaiting to see Ashley's reaction.

"Oh? Well, I don't really care if you are into cuckolds and stuff; I love you for who you are, Jack," Ashely said as she grabbed Jack's hands. "Let's go on patrol for a bit, okay?" Ashely said as she blushed, looking away from Jack in embarrassment.

And so, Jack and Ashely went on patrol. They talked about what they missed about each other, how Ashely had graduated from the hero academy and became a legal heroine, even before Jack's sister.

Jack opened up to Ashely about his cuckold fetish and all the superpowers he knew he had; Ashley heard him attentively, not mocking him or feeling creeped out; instead, she gave him some advice.

"Well, if you want, what was his name? Brandom right? well, if you want Brandon to become a villain, and you get stronger every time you get cucked, why don't you ask your system for a quest." Ashley said as she sipped a soda can they bought earlier.

"Well... I don't know if I can't do that," Jack answered truthfully, but a system window popped out.

[Hey >:[, that's because you never ask, idiot.]

[System Quest-Blacked Childhood friend: Make Ashley have sex with a big black cock.]

"..., Ashely, I got a quest," Jack said, dumbfounded, as he looked at his system window.

"You look cute when you are an idiot; what is the quest?" Ashley asked, finishing her soda, slamming the can against her forehead, and folding the can on contact.

"It says you need to have sex with a black cock" Jack answered Ashley. "So, how do you want me to do it?" Ashley asked back.

"Well, I have this fantasy where Brandon starts his criminal empire; you go to stop him, he beats you, and the fucks your brains out, and after he finishes fucking you, he forces you to work for him as a slut, alongside Rika."

Ashely stared at Jack with no expression but then smiled and patted Jack's shoulder. "Whatever my honey asks for, but only on one condition!"

"Which is?"

"After that, we go on a lovely date!"

What should Brandon do?

1. Impregnate Ashley

2. Gangbang Ashley

3. Anal defloration to Ashley

4. Exhibitionism Ashley

5. Get Ashley hooked on something.