Part 25
As in, anal?
The phrase Chris had repeated countless times at this point about what he ‘wanted’ was never meant to be anything beyond satisfying the girls with the blatantly untrue words. He wasn’t into guys. He had never experimented with anything back there. And, because Julia was a girl, the obvious assumption was that he would be fucking her, despite how she had phrased it the opposite.
He hesitated from both the surprise, as well as this being another moment where he had to remember to speak the way she and the others kept insisting. “That’s not . . . I don’t-” What was he supposed to say? Anything that contradicted what Julia had been present for thus far would potentially get back to Amy, and he had gone through such lengths to keep this contained to just her and her friends.
“It’s okay, Chrissy,” Julia smiled, speaking in a reassuring tone, “If you’re not ready, I won’t make you. How about this? Bend over the desk, and we can talk about it.”
That felt like a bad idea. But also, Chris was too off balance to resist her suggestion. Between his recent loss of hair down there, the fact that Julia was just as hot as ever in her lingerie, and how he was used to listening to the mixed girl after everything from downstairs, Chris reluctantly let her walk him over there.
Following her instructions, he placed his arms on the desk and jutted his ass out slightly. It wasn’t a particularly wide desk, plus Julia told him it was better if he had some room to move around back there. He felt his breasts more than ever in the new position, as he wasn’t used to having such weight dangling from his chest. Even with the bra holding them in place, it was quite the contrast compared to a lifetime of not having boobs at all.
He didn’t lose sight of Julia completely. The small mirror from his make-over was still on the edge of the desk, so he had eyes on her lingerie-clad body.
“You know,” Julia said, cupping one of his lower cheeks with her hand, “My ex was curious about anal. Like, with his ass, not mine.” She gave me a squeeze. “There’s something so hot about a guy who’s into stuff like that. And when I found the right spot back there . . . Holy shit, Chrissy. I’ve never heard a guy moan like that.”
It was a conflicting visual. On the one hand, Chris had heard about the g-spot thing back there. He had never been curious enough to experiment with it on his own, nor had any girls brought it up in the bedroom before Julia. At the same time, he didn’t want to picture another guy moaning. He did his best to make her story like porn, where he blurred out the male and pictured himself with the girl instead. Of course, that meant he started thinking about doing something with Julia he had zero experience with.
When he didn’t reply right away, Julia continued, “What do you think, Chrissy? Want to try? It’s important to expand your sexual horizons. I bet you’ll like it, too. I know it will turn me on.”
What Chris really wanted was to fuck Julia properly. But this was apparently something she was into and, while he was still quite hesitant about the concept of being penetrated back there, some small part of him was considering. Not because she had piqued his curiosity, or anything like that; it was mostly a combination of getting a new experience under his belt, as well as impressing Julia with his open-mindedness at the same time.
It didn’t hurt that she was implying that she was thinking about Chris as a guy at the moment, despite his breasts, voice, and everything else. Even an indirect reference to Chris being male was refreshing after all the humiliating ‘Chrissy’ nonsense.
Clearing his throat, which was an endeavor itself when he had to do more of a feminine grunt instead of what he would normally sound like, he felt his blush returning as he continued speaking like a girl. “I . . . don’t know.” It was the truth. Chris had always expected the first time he would be exploring anal would involve the girl’s ass, rather than his own. AS for pushing normal sex, that was a bit difficult while he was bent over and Julia was idly groping him as they talked.
“Hmm,” Julia mused. She gently traced her fingertips up and down his crack, pushing between his cheeks ever so slightly with each pass. “It’s really up to you, Chrissy. Are you a scared little girl?”
“N-no!” he insisted. God, that was so much worse than being called a girl in general. At some level, he knew what Julia was doing, yet that didn’t change the fact that being patronized while half naked with a girl wasn’t preferable. It was difficult enough to feel sexy after losing the last of his body hair, as well as the way his breasts slightly shifted whenever he did. And, since Julia recently brought up what she did think was hot, Chris found himself latching onto that as a way to course correct.
Julia wasn’t being particularly subtle about it, either. Continuing to casually press, she asked, “So, you think you can handle it?”
Such an obvious no-win question, in a moment where thinking clearly was impossible. Julia’s fingers did feel good back there, but she also wasn’t doing much beyond teasing him and getting him used to her presence in a place no other girl had explored him. “Handle- um, handle what?” Chris hesitantly asked. Stalling, but also not sure exactly what the mixed girl had in mind.
“Hmm, let’s start simple,” Julia said, sounding just as nonchalant as ever compared to Chris’s reluctant girl voice, “Relax for me, girl. I’m going to stick my finger up your ass; I want you to imagine it’s a hard cock. Not a very big one, I guess, but you have to start somewhere!”
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