Some more training

Jack fit the middle-sized plug into Anne's shiny, well-lubricated ass. It was roughly half the thickness of his dick, but about equal in length. Anne didn't try to hold back her moaning. At this point, even though everyone outside could hear her, no one cared.

While Jack worked the plug around her anus, stretching her gently, she lay on top of him in a sixty-nine position. She held his hard cock in her mouth while moaning, and he felt the vibrations of her throat.

Jack pressed his tongue against the folds in her pussy while continuing to stretch her ass with the plug, and toy with her clit between his fingers. She couldn't handle the stimulation and spat out his dick, drooling over his balls, gasping loudly as her excitement reached its peak.

When her pussy and ass clenched down in orgasm, Jack quickly withdrew the butt plug, eliciting a deep moan from Anne, and then thrust his tongue as far as it could reach down her anus, forcing her eyes to almost roll-up into her head from the new and intense pleasure. He pumped his tongue in her anus and his fingers in her pussy until she collapsed on him, pressing her breasts against his slick cock.

Jack held her there, happy to make his lover orgasm again, and satisfied to simply massage his hands over her body, squeezing the plump flesh of her ass and hips.

"God, Jack, we don't get any points if I'm the only one who comes." She slowly flipped around until she rested her head on his chest, her legs trembling slightly against his body. She lazily stroked his hard cock with a hand while she rested.

"I have to loosen you up so we can earn points faster in the long run, though," Jack said, slipping a couple fingers into her anus.

"Ugh, you're so obsessed with my butt."

"Sorry."

"Don't apologize. It feels good." Anne smiled at him, teasing one of his sensitive nipples with her free hand. "You think it's ready?"

"Not yet." Jack shook his head. "But maybe we can move to the next size up," he added, waving the larger plug in front of her face. He smiled as she caught it with her mouth and pretended it was his cock.

"What are you waiting for?" she asked, spitting it back out.

Jack rolled her over until she was lying flat on her stomach and poured more lube onto the new toy and her anus. Her toes curled and her feet slapped against his back at the cold sensation, and then she kicked out as he pushed the plug inside her anus. At the same time, he slipped the tip of his dick into her pussy, fucking her between her thighs.

"Ooohh," Anne moaned loudly.

"How is it?" Jack asked, enjoying himself in her.

Anne craned her neck to lock lips with him. "Soo good," she gasped between kisses.

He turned her face back towards the bed and then held onto her hips and started thrusting, hard and fast.

"Cum in me, please!" she cried out, moaning again when he grabbed the plug in her ass and pumped her with it.

Jack kept going, faster, and faster, until he was slamming into her at full ****, and stretching her ass wide with the large butt plug.

"OOohh! I'm coming from my ass!" Anne shouted, forgetting that the others could hear her, and then spasmed on the plug in her ass and the dick in her pussy. Finally, Jack shot his semen into her, and she kept coming together with him, until he was spent, and her pussy was full of his hot cum.

Outside came a tiny giggle from Em, followed by a loud laugh from Letty, and then the others joined in. Anne was red faced, kicking her legs playfully against Jack. "How could you!" she shouted at him, as if it were all his fault that she'd screamed about coming from her ass.

Jack just smiled and laughed at her, grabbing her flailing legs and then pressing forward, ignoring the arms slapping his chest, and quieted Anne with a deep kiss. She went limp, finally losing the strength in her body, and collapsed under him.

She spoke quietly while looking into his eyes, to avoid anyone else hearing. "I love you."

Jack leaned closer and whispered against her ear. "I love you, too, Anne."

She stifled a squeal of delight and hugged him close, before falling back to the bed and snuggling up against him, ready for sleep.

The two were satisfied, exhausted, madly in love, and incredibly happy.