Play a bit with Jess.

Jess grins as you grab the receipt, taking a photo on your phone to make sure you don't lose Anna's number. The buxom waitress is going through your mind, though you find yourself surprised to realize you are thinking of more of what she and Jess will do together. Likely because that's the most obvious possibility you realize. Jess wasn't wrong when she said you might not be involved. You know yourself well enough to know you'll be nervous. But if you're just watching.

You picture Anna biting her lip as Jess slowly exposes her. You don't get much further than that as the elevator door closes, and Jess leans up, kissing you hard. You snap back to reality in moments, and your hand slides up Jess's hip to find her breast. She sighs into your mouth. "Pull it out if you want. Fuck it. Play with my tit," she groans, biting your lip. "You're probably going to get those big ones, too."

Jess's language is provocative enough to flash another image of you with a handful of the busty waitress's tits. You groan and Jess pulls away. "Oh, have at them," Jess encourages you. "Use them for your fun, John." She looks at you, and then whispers into your ear. "You've always wanted a bigger pair of tits. This will be fun for you. I want you to enjoy this as much as I do. Who knows what will happen?" Jess kisses your neck, and you reach down and expose her breast just as the elevator door opens. There is no one there. Jess grins. "Leave it out. If some old guy and his trophy wife see it, maybe you'll get your shot at her, too. My guy, fucking his way through our resort," the speed of Jess's speech jumps, and you realize how turned on she is. "What a terrible person I am," she whispers, even as she pulls your hand. "You ask me to marry you, and now I want you to fuck every woman in here so I can get off watching," she murmurs. You feel your cock lurch at the opportunities she's offering. You make your way to the room, and you're half disappointed that you didn't see anyone on the way. As the door closes, you peel Jess's dress off of her, and push her against the door.

Your hand reaches down to push against her panties, and Jess moans. "Why did I wear these?" she complains as you rub her pussy through the fabric. "I could be fucking you right now, but instead you're just teasing me." You lean in to kiss her, and feel her mouth open eagerly for you. Your hand slips from her hip to her exposed tit and she grunts as you eagerly squeeze and press her breast against her. She pulls away. "I'm so hot and wet right now," she breathes. "Can you please fuck me?"

You shake your head as you lean in to kiss her again, and Jess's mouth melts even as she lets loose a low, mournful whimper into your mouth. When you pull away, you glance at Jess, and reach into the dress to pull out her other tit. "Anna really likes this dress. I think you should keep it on," you tell her. You're only half-teasing. "Make her take it off you," you tell her. "Make her earn her spot between your legs," Jess groans as you ramp up the preparation.

"You want that big titted waitress on her knees for me?" Jess asks, watching as your hands squeeze her smaller breasts. You groan as you realize that you're going to marry her, and Jess reaches for you. "You want to see me eaten, baby? Another woman? Her big, hanging tits swinging as she tongues me?" You groan as she reaches down and pulls her panties aside. "I'm so wet," she repeats. "Can you put your cock inside me?"

You wonder if it would help to keep Jess in some control to give her some relief until Anna joins you, or if you'd rather see her almost overwhelmed when the busty waitress comes in. It seems pretty obvious what Jess wants.