You have a proposition for Emma.

You take some time to rest, drink water (lots of water) and simply just catch up on things. You all sit around the huge bed as they ask how the trip went, how Japan was and a few more details about your relationship with Anzu.

On your part, you ask what they did during the break, and you’re very happy to know they spent most of it together. You knew they had been going out as a group, but it seems it was more than just that. The last week was spent working on your place, they say.

“When do I get more details about this trip to the sex shop?” You ask.

“That’s a story for another time.” Emma winks. “We’ll tell you, don’t worry. It’s just that it would take too long.”

“I guess we were so caught up that we forgot to use any of the things we got.” Emily points out.

…

That reminds you. Anzu said she used toys. That she used them for… anal.

…

“Do you… happen to have lube around?” You ask, which is odd considering this is your own home.

“We do, actually.” Megan nods. “We didn’t use it, though.”

You look at Emma and she raises a brow in confusion, not knowing what you have in mind.

“Do you think we’re ready to try that?” You ask her.

“That? Oh! You mean…”

You nod.

Emma bites her lip, thinking for a moment before she nods eagerly. “Yes, I think we are!”

“What am I missing?” Sophia asks.

“Wait. Are you going to…” Mia says, blinking a couple of times.

“Yep, we’re finally doing anal!”

“Oh wow.” Emily says, looking a bit shocked. “I… why did I forget that’s actually a possibility?”

“We’ve been getting ready for MONTHS!” Emma exclaims. “I know for sure I like it now, but the most we’ve done is using his fingers. I’ve used toys to prepare, but I think we’re finally ready!”

“Still, let’s use a condom.” You say.

“I’ll go get it and the lube!” Excited, Emma gets up and dashes towards the bathroom. But when she gets back, she hides behind the door like a shy little girl.

“What is it?” You ask.

“So… you’re all just going to watch?” Emma asks with uncharacteristic embarrassment.

“Of course. Don’t tell me you’re getting shy now?” Mia asks with an amused grin.

“I’m practically losing my anal virginity here. Let me be.”

“Come on! Let us watch! We’re curious.” Megan says.

“Yeah. Who’s to say some of us don’t feel like trying it in the future?” Emily argues.

“That’s right. You’re our teacher, aren’t you?” Sophia adds.

“Alright, fine! But I get to watch when you lose yours, too!” Emma says, coming out with a bottle of lube in one hand and a couple of condoms in the other.

“By the way,” Mia says. “If you’re using a condom, I’ve heard of a trick that if you put a few drops of lube in it before you put it on, it makes it feel a little better.”

“Sure. Let’s try.” You nod.

Emma helps you put the rubber on and is very generous with the lubrication outside, but even so Mia still suggest she use more. You’ve read there’s not such a thing as too much lube for anal, so what the hell.

Emma takes a deep breath and gets on all fours before you get on your knees behind her.

“Go slow, okay?” Emma says.

“Of course. Tell me if it feels bad. We stop the moment you say it.”

“Alright.” She nods. “Go.”

You line up your cock and push it against her rosebud. Slowly, the tip of your dick goes inside, and you stop there for a moment. Emma half-moans, half-grunts at the sensation, but encourages you to keep going.

She grips the bed sheets tightly, but keeps her body as relaxed as she can. The feeling is… strange. It’s even tighter than her pussy, and maybe a little colder, but you wonder if that’s the lube.

“Oh my God! It’s really going inside!” Megan gasps at the sight. She and the others are gathered around you, eyes focused on the place connecting you and Emma.

“Does it hurt?” Emily asks.

“It doesn’t.” Emma says with a soft smile. “Keep going, love. I like it.”

You keep pushing your cock inside her ass, slowly getting used to the new feeling and… starting to enjoy it, even. It’s definitely different, but not at all bad. What’s more, Emma seems to be really enjoying it, if her grunts of pleasure are anything to go by.

Eventually, you’re fully inside her, and that kind of surprises even Emma.

“God, I feel so full!” She giggles nervously. “I didn’t think I’d be able to take it all inside, but it feels really good!”

“I wonder if your trait has anything to do with it.” Sophia mutters.

Huh. You know what, it might.

“You can start moving.”

You pull out slowly before going inside again. It’s gentle, but even then the sensation is intense for both of you. Your hold on her waist gets tighter as you resist a growing urge to get rougher.

Seeing her on all fours, her body giving in to the strange kind of pleasure is… a lot more exciting than you thought. There’s this feeling of domination that you can’t deny. Knowing that all her pleasure is in your hands sends a thrill through your body that only adds to the feeling of being inside her.

The others watch as you slide in and out of her ass, the lube doing an amazing job at making that a non-issue. They’re looking closely while still staying away from the act. Maybe they feel they shouldn’t get involved here? You’re unsure.

“Of fuck… fuck…!” Emma moans. “Yes… Yes…”

Her voice is soft, but you can easily tell how much she likes it. Her body is relaxed and shudders every time you thrust into her. Her breathing is heavy, and when she starts to subconsciously push her ass against you, you know she’s close.

And to be honest, so are you.

“Fuck… I’m gonna come, I’m gonna come, I’m gonna come…!!” She says rapidly, gasping. “Harder…! Fuck me harder!”

You accept gladly, thrusting into her with a more ****.

“Yes! Yes! YES!”

Emma’s body trembles as she reaches her orgasm. Her ass clenches even more around you, making you come inside the rubber with a loud grunt. You stay still until her ass loosens a bit any you pull out.

It was intense. It was different. It was… really good. You watch as Emma catches her breath still in all fours. She stays there, assaulted by small aftershocks of her orgasm.

“How was it?” Emily asks.

“…” Emma gives the blonde a tired smile before answering. “Absolutely amazing.” She then lets herself fall on the bed with a satisfied smile.