Chapters 1 and 2 tell the story from earlier in the evening.
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They continued to lay in other's arms, enjoying the warmth, the closeness. Face to face, they dozed lightly, occasionally sharing a long, light, intensely pleasing kiss. Mostly, just luxuriating in each others' arms, skin to skin, top to bottom. Eventually the kissing became more frequent, subtly more intense, trading tongues and licks and little bites.
He had to get up and visit the bathroom. On the way back he grabbed lube from his overnight bag, climbed back into the bed, under the warm covers, re-assuming the face to face position up against her bare skin again. The final plans for the evening were ready to unfold.
He reached behind to hold her ass cheek in one hand, gently squeezing, then stroking, top to bottom. He varied his mini-massage, from firm to light, as light as his fingernails, then as firm as deeply into her flesh. She shifted her position, leaning into him a bit and turning her bum more upwards, so he had easier access to more of her assets. Her eyes were closed as she silently enjoyed the attention, relaxing and anticipating his next moves.
Ever so gradually his massage slid closer to her crack. Each stroke, from her lower back to her leg, moved more deliberately to the seam in her ass, so slowly, yet with no question of the final destination. She squirmed as the tease continued, feeling yet again the wetness between her legs, and yet again that tingle of desire starting to grow. After an eternity, his stroking found the middle of her ass, and that one finger he had deployed stroked lightly, right over her asshole. She shuddered, realizing the fun was about to begin.
His finger now stroked the inner reaches of her butt cheek. From the small of her back, down the seam, over the hole, and all the way as far as he could reach to the fringes of her pussy. And then back again, all the way up to her lower back again. Occasionally he reached in her pussy with a finger or two to get a bit of her wetness on his finger, to help the trip back up. She wiggled as he did that, desperately trying to get more pressure on either hole as his fingers traced their passage, but he was elusive and determined, wanting to stretch the tease out as much as possible.
He paused for a few seconds, puzzling her. Why was he stopping? Then he resumed with a cool wetness to the touch and she realized he had applied the lube to his finger. She shuddered, and exhaled unevenly as his finger slid its way smoothly across her pucker, and back again. Another pause, for what she realized now was more lube, and his slick cool finger was back again, laying a smooth path down in between her butt cheeks.
He paused over her hole and danced his finger around, circles at first, gradually entering her with his index finger, slow pressure. She gasped and shuddered involuntarily, clutching him closer, as his finger worked on the millions of nerve endings in her anus. She kissed him warmly, entering his mouth with her tongue, while he continued to slide his finger gently in and out of her ass. Each stroke, he went a tiny bit deeper, until the whole finger was gliding in and out of her. She kissed him even more deeply, lusting for deeper entry, gasping as he pushed harder.