Allie's Adventures Pt. 03 - Punishment

The girl on the screen was laid on her back with her hips propped up on a pillow, rubbing herself with her legs spread wide, as the cock violated her back door over and over again. She was moaning and leaning into it, but at the same time kept saying "But I shouldn't! I have a boyfriend."

"Do you let your boyfriend fuck you in the ass?" the boss asked.

"No! And I shouldn't be letting you do it! It feels so wrong!"

"Well if he won't do this to you, then you're not cheating on him. Just like I'm not cheating on my wife right now- she never lets me put it in her ass. Now relax and make me cum before she catches us."

The girl moaned again. She started to repeat her protest, but could only manage to say "it feels so good, but we can't!" Even as she was saying it, she continued to rub her pussy and lean into the thrusting.

Jack interrupted her focus on the screen. "Do you still have a boyfriend, Allie?" he asked as he worked her pussy and fingered her back door.

"No, Mr. McConnell, I broke up with him after you made me cum."

"Because he couldn't make you cum, could he Allie?"

"No," Allie moaned. "Only you. Only you can fuck me like I need." She turned her attention back to the screen.

The male actor told the brunette he couldn't couldn't cum until she did, and that it would hurt his balls too much to stop without cumming. He promised no one would have to know about them fucking and he would keep it a secret as long as his wife didn't catch them. He needed her to hurry and orgasm for him though, because if his wife found out, she'd tell everyone. Every dad on the block would know what a seductive little slut she was, and they'd all want to use her willing little asshole too.

Allie thought for a moment about being passed around that way. Fucked by one man after another, all dying to get their fill of her. As she watch the ass fucking, she couldn't believe how much the brunette, who had at this point clearly forgotten her boyfriend, seemed to enjoy it. She could admit to herself that at first the finger had been a little... different... but mostly Allie had been afraid to let on how much it excited her. She loved feeling like she was breaking the rules. The finger was a tight fit, but with it all the way in she was enjoying it. A cock would be much too big for her virgin little asshole and petite frame, but his finger felt just right.

Jack had other ideas though, and Allie heard the lube cap snap open again. His finger slid out until just enough remained to keep her o-ring spread. When he began pushing forward again, Allie realized there was a second finger starting to penetrate her.

Before she could protest, Jack reminded her that naughty little pet sitters who fuck themselves on their boss's couch needed to be punished. He also kept reminding her how sexy she was, and how hot it was that she was willing to accept that she deserved this. By the time his second finger was all the way in, Allie was loving it. The sensations in her tight little hole were like nothing she'd ever experienced. She watched the girl on the screen, and pretended Mr. McConnell's fingers were his cock, even though the real thing would be too big for her. She pushed back into him, humping his cock and fingers for all they were worth.

Jack stared down at Allie's virgin back door stretching to accommodate his fingers. He started to spread them apart, working to gape her hole a bit in between sliding his fingers out and pushing them back in. She was so hot, and so willing, thank god he'd jerked off this morning and she'd sucked him off tonight or he'd have cum already. "How does it feel? Is this what you wanted, you naughty little slut?"

"Mmmm it's starting to feel really good. I know I shouldn't like it, but feeling you inside both my holes is just... soooo sexy. All I want is to have you fuck me over and over again. Mmm I just wish you didn't have fingernails," she said, squirming slightly.

Despite the complaint, Allie wasn't slowing down. The more he fucked her and stretched her holes, the more she moaned and gripped him with her pussy. Her breathing was getting short again and he knew she was getting close. He pulled out his fingers and Allie made a sound of disappointment, then he pulled out his cock. She begged him to put it back, that she was so close, and she wanted to cum for him like a good girl who had learned her lesson.

"Not yet, you little tease. You need a little more punishment before we're done." Allie heard the cap click again and wondered what Mr. McConnell had planned this time. What else could he do to her? Add a third finger? She would do anything, she told him, if only he'd put himself inside her again.

Jack looked down at his dick in his hand. He stroked it, covering it in lube. He wanted this to be as comfortable as possible for Allie. She was leaning back, begging to have his cock again, begging to cum. He held it and leaned forward, pointing it at her puckered little sphincter. The feeling of the head of his shaft touching her forbidden little hole shot a bolt of lightning through him. It took everything he had to take it slow and not hurt her.

When it first touched her, Allie thought it was his fingers again, and he'd just lubed them up more. She moaned and relaxed, assuming his cock in her pussy would be next. As Jack pushed forward further though, she realized she was stretching way more than before.

"Mr. McConnell, what are you doing to me?" she cried out.

"Giving you what you asked for, you sexy little slut," he said, grabbing her hips and continuing to slowly push forward. "You begged to be punished with my cock, and now you are. You deserve it. You've been just as bad as that little whore on the screen."

"Oh, but you're too big! You'll never fit in my ass."

"I thought you said you'd do anything if I'd just put my cock back inside you."

"But I didn't mean-"

Jack gripped her hips firmly so she couldn't pull away and interrupted her. "Maybe you'll remember this the next time you want to fuck yourself on my couch."

Allie gasped and gave a whimper as the full head of his penis entered her. Jack gently said "Relax and trust me, Allie. Are you still teasing yourself with your vibrator?"

"Mmm yes, just like you told me to," she said meekly.

"Good girl." Jack moved forward further, and felt the head of his cock push past her o-ring. He felt her sphincter contract around his shaft, gripping him. "That's the worst of it, baby. The biggest part. Now you're going to enjoy this, just like that little slut on the screen, aren't you Allie?"

Allie let out another whimper as he continued to penetrate her tight virgin hole, but she didn't resist. She looked up at the screen to see the brunette in her tennis shoes now on top, bouncing on her employer's cock as he invaded her asshole completely. The babysitter continued to protest that it was wrong, but her disapproval of their behavior didn't seem to damper her enthusiasm as she lifted up and thrusted back down onto his cock over and over again.

She let out an involuntary "mmm" as she continued to watch and play with her vibrator. Jack continued to push forward, telling Allie how beautiful she was and that she deserved this. Soon he was all the way inside her, and he gave an extra thrust to bury himself completely. Allie felt his hips pressing against hers, and another moan escaped her. Slowly she rotated her hips, trying to stretch herself so it didn't hurt quite so much. Even with the pain, Allie felt pleasure coursing through her.

Jack was staring down at his cock buried completely inside sweet innocent Allie's back door. She was whimpering and writhing on him, and he worried he was hurting her.

"Are you okay, Allie?"

"Yes, but I need a minute. You're just so big, Mr. McConnell," she moaned, continuing to roll her hips.

Jack did as she asked, holding perfectly still, letting Allie get used to the sensation. It was taking all the self control he had not to blow his load with the way she was wriggling around his pole, but he knew it was too soon. He needed to show her how good it could feel, or she might not let him do it again.

After a few minutes of deep breathing and thinking about anything except what was going on in front of him, he noticed Allie was starting to pull away and push back again. She was practically inviting him to fuck her asshole, and he willingly accepted. He pulled out a few inches, and gave a thrust. Allie gasped, and let out a guttural sound as she leaned into him. Jack watched, mesmerized, as he pulled out and thrust in again. Every time he pulled away, her sphincter clung to him, like she never wanted him to leave her ass.

He was thrusting slowly, but Allie began to beg for more and buck her hips back into him.

"You like that, don't you, you little slut?" he grunted to Allie as he picked up his pace and thrusted harder. "Say it for me. Admit it."

Allie paused for a moment, but she realized it was a little late for embarrassment. The words spilled out of her mouth before she could censor herself.

"Yes, Mr. McConnell, I know I shouldn't. I know it's wrong and so dirty, but I love you fucking me in my virgin little asshole! I love being your dirty little slut- your dirty little secret. I deserve this. I deserve to be fucked and punished and passed around and I'd do anything to please you! Just don't stop baby, pleeeease don't stop. Fuck me. Give it to me like the little whore I am."

Jack listened to the torrent of words, enjoying each one more than the last.

"You're so sexy, Allie. I love watching my cock spread that little hole of yours wide. God you look good."

"Record it so I can see," Allie gasped. "I want to see myself getting fucked like all those bad little babysitters on the screen."

Jack was floored by her request to be on camera, but he was thrilled. He grabbed his phone and did as she asked. He loved point of view porn, and this was going to be gorgeous... Allie's tight little hole being stretched to its limit as she begged for more. He'd gotten several minutes of footage when Allie's breathing began to change again- his little slut was getting close.

He decided not to make her wait any longer. She was definitely going to allow him in her ass again, and he would have a willing little butt slut at his disposal after this.

"Okay baby, you've accepted your punishment like a good girl, so I think it's time for your reward. Are you ready to cum for me?"

"Oh god yes! Thank you Mr. McConnell. Mmm, fuck my ass! Harder baby, harder!"

Jack gripped her hips and slammed into her with complete abandon, thrusting again and again into her vulnerable little asshole until Allie let loose.

"Oh-oh-oh-uh-hunh yes, yes, yESSSSSS FUCK MEEEEE!" Allie screamed as she let loose. Her entire body tensed as the first wave of her orgasm hit, and her ass gripped onto Jack like she'd never let his cock go again. She was screaming and bucking, begging him not to stop. Jack thrust into Allie over and again, determined to make her release last. As she was finally starting to slow, Jack felt his own orgasm imminent.

"Fu-fu-FUUUUUCK ALLIIIIEEEE!" He thrust into her with complete abandon, his hips slapping against hers. His orgasm was loud and long. He thought he'd never finish cumming as he pumped shot after hot, sticky shot into her stretched little virgin hole. "Not a virgin hole anymore," he thought.

He and Allie collapsed to the floor.

"Mr. McConnell, that was incredible. I never thought I'd enjoy taking a cock into my asshole, but I enjoyed yours. I never thought I could stretch like that."

"And we're going to enjoy it again and again, gorgeous. But I think it's time you call me Jack. It's a little silly to be so formal with someone who just popped your back door cherry."

Allie smiled. "Ok Jack. Only... can I still call you Mr. McConnell when you're fucking me?"

They had laid together for about 10 minutes when Allie remembered and asked to see the video. Jack leaned against the couch and Allie sat with him in the crook of his arm. He grabbed a blanket off the couch with his left hand. As Allie covered them up, he grabbed his phone with his right hand and cued up the video.

Despite the fact the quality of the video wasn't great, Allie found it intoxicating. "Oh my God, look how much you're stretching me!" she gasped, her eyes glued to the video.

"And you loved it," Jack said confidently.

Allie tore her eyes away from the screen to look at him. "Yes... Jack. I did. I loved it like I love the way you eat me. I don't know what it is about you, but I've never felt anything like it." She looked back to the screen, watching Jack slide in and out of her, over and again, committing it to her memory.

"Look at the way your body clings to me, like you don't want me to stop," Jack whispered in her ear.

"Maybe it's because I don't," she replied.

Jack leaned in to kiss her once again. Allie kissed him back, then reluctantly pulled away and said she had to go.

"I'll send you the video; give you something to think about," Jack said with a wink.

"Oh, bad idea. My parents have some weird app on my phone to track keywords and photos until I pay for my own. I've been saving up."

Jack reached down to grab his wallet. He handed Allie a fistful of cash. "Maybe this can help toward the cause. I have to go out of town in a few weeks and I'd love to be able to send you a few things while I'm away."

Allie smiled. "You're always so sweet to me. I promise I'll send you some things back if you like," she said. And then once again she was gone, her perfume wafting behind her.