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Chapter 11 by derprezingdent derprezingdent

Does Tony... go ahead with her request? Ask she take him instead? Something else?

Wait a second...

Seeing Katie presenting herself to him caused a stir of emotions and thoughts inside Tony's mind. Oh my god, she's beautiful; I can't believe we're finally doing this!; Wait, how the fuck do pregnancies even work here?; Say something you idiot! However, one thought managed to work its way to the top of his brain: There's no way in hell that thing will fit inside me. At first he tried to push it aside; after all, he was the one penetrating her. But remembering their blowjob trade, he realized something: This wasn't fair.

"Tony, are you okay?" Katie's worried voice cut through the maelstrom in his mind, bringing him back to reality. She was standing in front of him now, a look of concern on her face. "What's wrong?"

"Katie, I... I can't..."

A look of pain and sadness came over Katie's face, causing Tony's heart to nearly break in two. "Why... why not? Are... are you still... " Katie looked down at her crotch, then back at Tony, with tears beginning to form in her eyes.

"Katie, please..."

"No, it's fine. I... I understand. I can't expect you to... to..." She turned and started gathering her clothes, tears falling down her cheeks.

Tony placed a hand on her shoulder. "Please, let me explain!" Katie brushed it aside and stepped away from him. Realizing just how badly this was about to go, Tony decided to just spit it out. "I want you inside me, Katie!"

At this Katie stopped dead in her tracks. Seizing the opportunity, Tony desperately attempted to explain himself before his best friend and the woman he loved walked out of his life, probably forever. "What you were offering was something special, something magical, and something I can't return. Not yet. And I don't want to take that until I can offer it back to you. It's not fair to you if I..."

He was stopped by a forceful hug as Katie nearly tackled him, her tears now tears of joy. "Tony, I'm sorry. I was so afraid that you couldn't accept my... differences... that I forgot something important about you."

Tony wrapped his arms around Katie, holding her tight, never wanting to let her go. "What... what about me?"

Katie kissed Tony square on the lips, then answered, "You're always thinking of others. And that's why I love you so much."

"I love you too, Katie, and I'm sorry that I keep saying dumb shit that makes you upset."

"Don't worry, Tony." Katie smiled mischievously. "Hearing you say you wanted me inside you made it all better."

Tony smirked back. "I was wondering what was poking me in the stomach."

"That's not the only place it'll be poking you... Let's get you ready for this bad girl."


Tony was on all fours, with Katie kneeling behind him. She spread his ass, exposing his virgin anus to her. Tony nervously stammered, "So, uh, I know I've been saying this a lot, but I've never done this befooooooooohhhhhh god!" Katie ran her tongue along his anus, simultaneously stroking his hardening shaft. Katie gave him a few more licks before pausing to ask, "I take it that you're enjoying yourself?"

"I'm not going to lie, it's kinda weird..." Tony let out an involuntary moan as Katie stepped up her game, pushing her tongue into his ass and beginning to tongue-fuck him. "Fuck, Katie..." Tony hissed. "Keep... keep going..." Katie was happy to oblige her lover, and increased her speed on his ass. Tony bit his lip as Katie pumped his dick faster, matching her tongue's speed. "Oh... Oh god... I'm gonna..."

However, as soon as he said that, Katie instantly stopped. "Not so fast, Tony. We're only getting started."

"O...okay..." Tony muttered in embarrassment. He really needed to work on his stamina. At least Katie was understanding. It also seemed that, due to the shared sexual equipment of both sexes, it was completely normal for a woman to be in charge of an encounter. Although, it wasn't necessarily rare back in his old world, but it was seen as emasculating. That was something he didn't miss about his old world, he realized. As strange as this new reality was to him, he was glad that it didn't have the same weird sex bullshit. In fact...

Katie rudely interrupted his inner musings by worming her finger inside of him. Tony arched his back at the strange sensation. "Wow, Tony. If just a finger is doing this to you..." She pressed down directly on his prostate, sending a tingle throughout his entire body, causing his cock to twitch slightly. "...I can't wait to see what THIS'll do!" She punctuated this sentence by lightly slapping Tony's ass with her titanic member.

Tony bit his lip harder as Katie pulled her finger almost entirely out, before thrusting it back in, hitting his prostate for a second time. A few drops of precum fell onto the floor beneath him as the foreign yet oddly pleasurable tingles shot throughout him again. After a few more finger thrusts, which elicited soft moans from Tony, Katie stopped. "So, how are you feeling?"

"G....good..." was all that Tony could muster.

He couldn't see Katie, but he could hear the smirk in her voice as she asked, "Ready to try another finger?"

"Ready to try another finger?"

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