Emma. She waited the longest.

"I think it's only fair to fuck Emma first, as she has waited the longest", you say.

Kimmy looks disappointed but Natalie and Mary appear relieved.

"Liam will keep the rest of you company while I fuck each of you individually. Suck his cock well and he might even reward you with some cum to swallow."

Liam instantly moves up to Kimmy and you make eye-contact with her as she takes Liam in her mouth. Her eyes are pleading and you begin to seriously consider, if there is a connection between you.

You turn your attention back to Emma and begin to pour lube all over her ass. Then you massage her gently and when you begin to massage her anus she moans softly.

"Looks like someone isn't as uncomfortable as they said Emma", you say playfully.

Emma just moans in response. When you think her ass is as lubed as possible, you position your cock at her entrance. Emma holds her breath and when you begin to push against her hole you encounter more resistance than you thought you would.

"Try to relax sweetheart, it will be more comfortable", you try to say.

You feel her relax and seize the opportunity to push a bit harder. Your cock slides two inches inside with a slurping noise. Emma grunts and tightens her asshole again.

"It's alright, I'm already inside Emma. Just relax"

She reluctantly relax and you try to push further in.

On your right, Liam lets out a loud moan and you hear Kimmy trying to swallow the loads of cum he's shooting down her throat. She doesn't completely succeed and some of his cum leak down onto her face and further down on the bed.

Some of the girls were facing Liam and Kimmy and the sight appears to have turned them on. Natalie is moaning loudly and her body language clearly signals that she's getting close.

Returning to Emma's ass you're not making much progress. Emma doesn't seem to be relaxing and every time you try to slowly move your cock deeper, she grunts and objects. You decide that this is not gonna happen if you insist on being as considerate as you are now.

"Breathe slowly and relax your anus again", you tell her.

Then when she show she first sign of relaxation, you push your cock hard into her ass. Emma screams with a mix of pleasure and pain, and in three thrusts you're entirely inside her ass. It feels amazing. It's tighter that you could have imagined, and her ass is contracting furiously around your cock, massaging it.

Emma is breathing heavily and you decide to pour some more lube on her ass before continuing. That helps. When you begin to slide back out she arches her back and groan. Then you begin to thrust back and forth. Emma is grunting heavily and she appears to be in a lot of pain. She closes her eyes and tightens her hands.

Eventually it gets easier and Emma's moans begin to show signs of pleasure. The vibrator is still inside her and at a certain point, Emma cums when you thrust your cock especially deep inside her ass.

Her contractions are powerful and she squirms with pleasure.

"Mmmmhh fuuck! Fuck my ass James. I'm beginning to enjoy this."

You don't want to cum though as that would mean you'd have to recover, and you don't have that much time in the luxury room.

When Emma finishes her orgasm, you pull out of her ass and she moans disappointedly.

The other girls turn and face you. Kimmy looks at you with a smile but some of the other girls seem both worried and excited.

"How was it Emma?", Natalie says worriedly.

"It's a bit painful in the beginning but it's fine once you learn to relax completely", Emma responds.