Vol.4 Ch.19 – Slightly Educational
Chapter 19: Slightly Educational
Rachel was starting to really like Jeanne, to an extent that she didn't feel like reflecting on, but sometimes her girl could be a real dumbass. Case in point, the way Jeanne had beaten Abigail in that duel. Rachel understood perfectly why Jeanne had done it but that didn't make it any less stupid.
It was even stupider considering Stollos wanted the girl to be the next one to go through the Oath of Crystal Tears. Knocking her out like that probably hadn't made it any more likely for Abigail to jump into bed with both of them. And that was without even getting into the girl's baggage, which Abigail had a lot of.
Rachel didn't always appreciate her ability to see people's desires. Not so much because she sometimes saw desires in people she would rather not have known (she only wore long-sleeved clothes around Demon Lord Leviathan lest the nutcase get any ideas with that cleaver of his) but mostly because ironically the ability to see desires also came with the flip side of seeing people's lack of desires and the reasons thereof.
And Abigail had a lot of issues to work through. Intimacy did not come naturally to her. Even masturbation was something Abigail only did for stress relief. Romance and desire were things that didn't play a part in her life.
And the worst part was that Rachel barely needed her abilities to see that. It was obvious just from watching Abigail's performances. Songs about loneliness, inadequacy and heartache came naturally to her but whenever she sang about love there was a disconnect there. Her performance was still immaculate but it lacked that little something extra. The emotions just weren't there because love wasn't something Abigail was in the habit of experiencing. Or rather, romantic love wasn't. The girl clearly loved her mother and familial love was easy enough for her to sing about but romantic love was a different story.
There was a kernel there, a desire for love and for someone to rely on, but it was buried under a thick layer of cynicism and apathy. And Rachel hated seeing that in her. Because it was something she was trying her very best not to admit she was feeling as well.
Rachel had already accepted that Jeanne was someone she liked to spend time with, far beyond the scope of her usual fuckbuddy relationships. But admitting that the angel made her feel things she hadn't been feeling for centuries was... difficult. After centuries of not having feelings that ran this deep she had almost managed to convince herself that she didn't feel the same way normal people did but... That stupid headstrong, gorgeous, loyal woman made her reconsider.
She almost snorted but managed to rein it in, not wanting Abigail to think she found her performance silly. Maybe Rachel could help Abigail, talk things through with her and help her reawaken some of those buried desires. And maybe, just maybe, during that conversation she might figure out her own feelings as well.
**
Cassie had had a lot of awkward sexual encounters in his time.
Part of it had been caused by him going out of his way to present as the opposite sex, sometimes a little too successfully. Part of it had been caused by his own complicated sexuality. Figuring that out had taken him a while and he'd gone through multiple partners doing it. It turned out, a lot of self-proclaimed dominant women who wanted to get with a crossdresser weren't too happy with a partner who enjoyed getting fucked as much as they did.
But on his scale of awkward encounters very few of them ranked as high as waiting for his girlfriend's lesbian girlfriend to take an enema in his bathroom so he could teach her about anal sex.
In all honesty, he was thrilled that Alexis had come to ask him for advice. He always felt awkward around the girl and that was both completely his fault and absolutely not his fault.
Alexis was shy and awkward and painfully inexperienced but she was also an outspoken lesbian. She didn't feel terribly comfortable with her girlfriend dating a man and honestly, Cassie couldn't blame her. This was her preference and he wouldn't shame her for that, but at the same time he refused to feel ashamed for simply being a guy.
But apparently Alexis had done her best to try and extend an olive branch by asking him for advice. She could have gone to Evelyn instead. The girl had bragged about the reaming Elaine had given her ass after all. But Alexis hadn't. She'd asked him.
And that was great. What was less great was that Cassie felt like he had to walk on eggshells around her. He didn't want to spook her, didn't want to come across as predatory. He'd done his best to dress up as feminine as possible, to make himself seem as non-threatening as he possibly could, but there was still every chance the girl would get uncomfortable. But she'd decided to extend her trust to him and so he was going to try his best to accommodate her.
Explaining to her how to properly take an enema without offering to enter the bathroom with her and help her do it was part of this accommodation, which was why he was currently sitting on his bed in a babydoll nightie and panties, feeling awkward.
When the door to the bathroom opened and Alexis emerged he saw that the girl was blushing scarlet, letting him know that she'd done it. God, he knew exactly why Elaine had fallen for the blonde. She was cute and pretty, too pretty to ever be called mousy but so awkward the word still somehow fit. Her hair was long and golden blond, her figure slight and small. Right now she was in her underwear and he considered the fact that she didn't try to cover up and hide a good sign, even if she was almost shivering.
“So, what's next?” she asked. She didn't stutter, though her voice did tremble a little bit.
“The next step might be a little difficult,” he said.
She just looked at him.
“Relax,” he said. “You're way too tense.”
“R-right,” she said, then sat down beside him.
He held a hand open, letting her decide whether to place her hand in his. With any other member of Elaine's harem he would have tried hugging her but he didn't want to spook Alexis, didn't want her to think he was about to jump her.
But she did place her hand in his and when he laid down on his back she let herself be pulled along.
“So, why do you want to learn about anal?” he asked once he heard her breathing even out.
“It felt so good when Elaine touched me there that I wanted to know how it feels to...” She trailed off, not wanting to spell it out. “What about you?”
“Hmm?”
“How did you get into that?” she asked. “I mean, I doubt a lot of boys are into this.”
“Oh you'd be surprised,” he said. He'd yet to meet a guy who would turn down a rimjob and not one had ever rebuked him for slipping a finger in during a blowjob. Though Cassie would freely admit that his sample was skewed simply by the fact that all the guys he'd been with were already dudes who were fine with a crossdresser. “But mostly it was because as a kid I read a lot of stuff I really shouldn't have at that age.”
“Books?”
“Manga, mostly,” he said. “It's amazing what they let you buy as a minor so long as the cover shows cartoon drawings.”
“What's it called?” she asked. “Yaoi?”
He chuckled. “God no. I mean yes, that's what it's called, but I was never into that. No, stuff about crossdressers, stuff about futas, that sort of thing.” Also tentacles and other stuff he didn't feel like telling Alexis about. “And eventually I got curious how that kind of thing felt like.”
“I'm not sure if I should ask this but...”
“Shoot.”
“Did you... What came first? Your interest in anal or your interest in crossdressing?”
That question caught him off-guard. In other circumstances it might have been considered rude. Hell, it might have been considered rude if she'd simply asked it in a different tone of voice. But Alexis wasn't judging him, she just sounded curious. “Anal,” he finally said. “The idea that I could look as good as the crossdressers getting fucked came later. At the start I just wanted to feel what they felt.”
“And did it live up to your expectations?”
“No,” he said, then clarified: “It feels way better.”
“Better than it does for girls?” she asked.
He snorted. “I mean, it's not as if I can know how anything feels for a girl. Girls don't have prostates, sure, but I've never been with a woman who didn't end up liking her butt played with.”
“Sometimes I forget that you're bisexual,” she said.
He didn't want to ask her if it bothered her. It might make her reconsider this entire thing. “I mean, I am dating Elaine, same as you.”
“Yeah, but she's kind of a special case, isn't she?”
Oh boy was she. “Yeah.” He knew his next sentence might make her bolt but, in the end, she had brought it up. “And yeah, I have been with girls. But just because I prefer having my ass played with doesn't mean I haven't had sex with women before. Does that worry you?”
“I trust you,” she said and his heart soared.