He was determined to have her tight little ass tonight, but she had no idea what he was planning.
Liz lay reading, as usual, and had quickly set aside her book when she'd felt his hand stroke her thigh. She had quiescently lifted her gown up and off, giving him a moment to look at her breasts and belly, before reaching to turn off her bedside light.
He'd removed his t-shirt and boxers as his eyes had adjusted to the moonlight shining into the room through the half-opened window. When he had leaned over to kiss her throat, he heard her typical sigh, and his fingers rubbing over her nipples had elicited the expected soft gasps. She had even wrapped her hands around his hardening cock as he began to lick and suck on her nipples, and then spread her legs for his hand to slide up and down along her soft, wet slit. She mewed slightly when he slid two fingers deeply into her and allowed his palm to press and rub over her swollen clit. She'd already been very wet, and only became more so as he continued sucking her nipples and fondling her pussy.
She'd not even made a token protest when he had lifted his head and removed his hand, wetting one hip with her own juices as he turned her over. She allowed him to pull her up to her knees, and reached her hands to rest on the headboard. She knew how he liked to have her torso stretched long for doggy style, so he could easily lean to kiss her neck, rub her nipples, and move his fingers over her wet clit.
After she positioned herself, he ran his hand from her clit all the way around to the tight little hole of her bottom. He smiled when her lower back dipped, lifting and opening herself to him even more. His fingers gently spread her wetness all around this tightest of holes. She moaned with her pleasure, and he was not surprised, knowing how much she loved these caresses, but only when the room was dark. She couldn't realize how the moonlight shone upon her wetness, highlighting the puffy lips of her labia, the pulsing demand of her pussy, and the softening of her little asshole as it began to relax with caresses. He slid his hand to gather more juices, rubbing, and then pressing his thumb at the center of her star. She gasped, arching her back further, feeling the slightly reluctant moue widen and transform as his thumb eased in.
It had only been a few days ago that he had introduced her to such unexpected touches. His initial success had much to do with the three glasses of wine she'd had at a neighbor's dinner party. He had known she was ready for sex, but had been surprised when she'd removed her panties in the car, and then unexpectedly raised her skirt and bent over the couch as soon as they'd entered the house. She'd been tipsy enough not to protest his slippery fingers gliding from her pussy to that small rosebud. Tipsy enough, that he was able to watch it pucker under his caresses by the light next to the couch. So tipsy, in fact, that he was able to feel the strong suck of the muscle along his finger as his cock moved in and out of her pussy.
It wasn't until the next morning that her sense of appropriateness had returned. Then, he'd lain behind her, rubbing his morning cock along her warm pussy, while kissing the back of her neck and pinching her nipples. She'd turned in his arms, pressing her hard, swollen nipples against his chest, and lifting a leg up and over his hip. His hands moved to her hips, but it wasn't until his cock was all the way inside her that he began to spread the globes of her bottom, and move fingertips over her asshole.
She stopped kissing him, and began to shake her head in protest, saying, "Tony..." in that corrective sort of voice. He didn't give her a chance to speak further, but kissed her aggressively and increased the friction of his sliding fingers. She tensed, hands tightening along his arms, and then softened slightly with the unexpected pleasure.
Her real protest happened when he began to press a finger to her hole. She pulled her head away, pushing at his arms with a sharp, "No, Tony!" But although inward push of the finger halted, he didn't stop entirely. His finger remained in place as he leaned forward to kiss and nip at her neck. When his mouth neared her ear, he whispered, "Relax and let me really fuck you."
His "let me" was mere politeness, because both his tone and his finger at her asshole were implacable. He resumed kissing her neck, and probing her with his finger. She was tense and very tight, giving a slight gasp of pain as he persisted. It wasn't until his finger was completely buried and he began to move his cock that he felt her soften and stretch. He had never heard her moan as she did that morning when he had her by her pussy and her ass. Later, with his finger sliding and wiggling, she came in a great gush that covered his cock and the sheets with her juices.