Slave For A Week Ch. 02

Will watched happily from his seat at the kitchen table as Jessica made him breakfast clothed in nothing more than an apron. Her cute butt was sticking out from in between the clothe, and when she turned he could catch glimpses of her breasts... despite the fact that he had seen her naked just this morning - and had fucked her just this morning as well - he was getting excited by the teasing glimpses. And he loved the way the apron framed her ass... he had big plans for that gorgeous ass today.

They ate breakfast, sitting right next to each other so that he could reach out and caress her if he felt like it. He made it his goal to keep her nipples hard for the entire meal, and for the most part he did a pretty good job. When she got up to do the dishes he had her put the apron back on, and she gave him a sexy look as she pulled it over her head and tied it around her waist. Whistling happily as he watched her clean, he thought that she looked fantastic like that.

Going over to the pantry he pulled out some of the vegetable oil, bringing it back to the table and waited for her to finish the dishes.

"Come here," he told her, "No, leave the apron on."

Raising an eyebrow she came over and gave him an affectionate kiss. He pulled away after a bit and patted the table next to him, "Bend over."

"Oh my," she said, laughing a little as she bent over, her breasts hanging underneath the apron and her ass peeking out cutely. When he pressed an oiled finger to her asshole she let out a startled, "OH!"

"Hold still," he ordered her, and she did, groaning a little as his finger pressed up into her hole.

"Will, I'm not sure I want to do this..." she said, feeling uncomfortably full as his finger wriggled around inside her ass.

"Shhh," he told her, pressing his finger all the way into her ass. It was hot and tight in there and his dick was swollen in anticipation, "I won remember... and I want my dick plugging this delicious ass."

Biting her lip she obeyed, knowing that in all fairness he had won and that she'd known he'd probably want to do some things that she wasn't as into this week. And honestly, it turned her on a little knowing that she was going to be doing things that she didn't necessarily want, just because he wanted to do them. Bearing down, she tried to adjust to the unaccustomed pressure in her ass, clenching and releasing around the invading finger. Smiling, Will added a second one for her to play with, and listened lovingly to her moans as her ass stretched. His fingers looked so erotic, sliding in and out of that tight virginal hole... this was actually only the second time that he'd fuck a girl in the ass, and he'd really loved it the first time. This was also his first virgin asshole, and he was really looking forward to it.

Jessica was starting to feel good, the fullness in her ass made her pussy throb anxiously, the slick thrusting turning her on. Although she'd thought about anal sex before she'd always thought that it would hurt too much to try... ok, so this hurt a little and it was uncomfortable when her hole stretched, but it really wasn't as bad as she thought it would be. Pressing back against his thrusting fingers she arched her back, enjoying the naughty sensation of something in her asshole. Will grinned, knowing that she was ready now.

Pulling his fingers out of her ass, he wiped off the slickness onto a napkin before coating his dick with the vegetable oil and lining it up with her ass. She gasped as the head pressed against her tight hole and stretched her open, hanging her head as it burned with the pressure, the head finally popping into her hole. Will groaned happily as her tightness bore down on his head, enclosing the sensitive organ and massaging it with her sphincter. Gasping, Jessica felt tears come to her eyes as he pressed forward a little more; feeling her resistance he retreated before pressing forward again, sawing back and forth in her ass in order to accustom her to the invasion. Slowly she felt her ass accept the intrusion and she relaxed a little... Will pressed forward more and felt her tense up again.

It was slow work into her ass, moving back and forth, pressing just a little bit more forward each time. She couldn't believe how huge he felt in her asshole, his dick felt much bigger than it did in her pussy... probably because her hole was so small. Groaning she rested her head on her forearms, all of her concentration was on the slow burning slide into her unused asshole.

For Will it was heaven, her ass was incredibly tight and slick, he loved the way it tried to grip at his dick but couldn't quite hold him because of the oil that was coating his dick. When he finally buried himself completely in her virgin ass - well no longer virginal ass! - he just held himself there; partially just to allow her to adjust completely and partially just to enjoy the way her inner muscles rippled across his dick. Her ass massaged his shaft as he held himself inside her, listening to her gasp and pant as his dick twitched inside that tight space.

When he began to draw out again, almost all the way to the tip of his dick, Jessica shuddered and moaned as the invading dick thrust its way back into her body. It burned, cramping her stomach a little as he began to slowly, but firmly, fuck her ass. Reaching around to grab her tits, Will whispered in her ear, "Play with your clit." and he pinched her nipples firmly.

Reaching down to rub her pussy, she found that the stimulation to her nipples and clit helped to relieve some of the discomfort in her ass. In fact, it was helping to relieve a lot of it. Maybe it was just that with every thrust she was getting more used to being fucked anally, but she was starting to feel kinda good. His dick made her ass feel a lot more stuffed than his fingers had, and even though her pussy burned to be filled up, it was rather erotic to have him in another hole. Fingers tugged at her nipples, making them throb with pleasure as they were toyed with, her own fingers rubbing her pussy incessantly as the stimulation roiled in her belly and began to build.

Moaning, she started to push back against his thrusts, moving her ass in rhythm with him. Delighted that she'd finally adjusted completely, he squeezed her tits hard and used them as leverage to begin really fucking her, riding her ass like he would her pussy. Squealing as the first of the hard, fast thrusts began, Jessica rubbed her clit faster in response, loving the way his rough hands felt on her breasts. The burning in her ass was becoming wrapped up in the pleasure of her pussy, making her bite her lip as her clit burned happily. Slick thrusting drove her higher and higher, she rubbed her clit harder and harder, until she felt her legs shake and she came.

It felt incredibly odd to be cumming with an empty pussy and a full ass, but good too. There was something hot and dirty about it, and she shuddered with ecstasy as her fingers continued to rub. Will could feel her ass convulsing around his dick, and knowing that she had cum while he fucked her ass was one of the hottest things he'd ever imagined. As her own orgasm began to slow down, he slammed hard into her ass, banging her hips against the table roughly before squeezing her tits as hard as he could and thrusting brutally one last time. She gasped as his dick throbbed inside her ass, she could actually feel every pulse of cum as it passed through his shaft and into her asshole. Groaning, Will emptied himself into her, shuddering happily as her ass continued to squeeze him throughout his orgasm.

When he pulled out he gave her ass a light smack, making her jump as he grinned, "Go ahead and start on the chores... I want to watch my cum leak out of that beautiful ass."

Grinning, he watched as she waddled slightly, going to get the vacuum.