Allie's Adventures Pt. 03 - Punishment

Allie had broken up with Chad the day after she rode Mr. McConnell at such a frantic, desperate pace. When he whined and asked why, she told him because he was either too lazy or pathetic to satisfy her, and then blocked him.

Allie was relieved to be single, but frustrated with the current state of things. It had now been three days since she had been over to dog sit. She was worried Mr. McConnell didn't want her there anymore. She tried to remind herself that she normally didn't dog sit on the weekends, but she had hoped he'd look for a reason to invite her anyway. She was afraid he thought she was disgusting. Why hadn't she controlled herself? She shouldn't have talked like that.

Beyond that, she'd left her White Knight laying on the floor at Mr. McConnell's house. She'd finally had a chance to see how good sex could feel, and now she'd laid awake the last two nights imagining not only the vibrator, but the feel of Mr. McConnell's magic tongue and thick cock, and wondered if she'd ever feel that good again. She thought about calling him or stopping by, but she didn't want to look desperate.

As she was finishing up her morning workout, Allie's phone dinged. It was him! The message was very simple. Just Mr. McConnell asking in his usual cheery way if she could come by after her classes to watch the dogs that night. Even though there was nothing special about the message, Allie felt a twinge between her thighs. She wondered if he wanted a repeat of the other night as desperately as she did. She hoped so.

As Allie got ready for classes, she debated what to wear. Remembering how good she felt when Mr. McConnell had complimented her breasts and clung to her waist and ass, she decided it was time to stop hiding her body. She pulled out a pink angora sweater from the back of her closet that was a size too small and a short pleated denim skirt, complete with cute girly tennis shoes. She'd worn the skirt recently, but always with an oversized sweater and leggings because of how short it was. With this sweater, the skirt sat just low enough on her hips to show her midriff and a peek of her navel. Without the leggings, her creamy thighs begged to be touched. Underneath she had a pink demi-cut bra that barely covered her nipples and a matching lacy g-string. When he'd given her the extra $200, she'd decided to spend a bit of it on a little extra something to remind herself how sexy she could be. Looking at herself in the mirror before she put on the sweater and skirt, she'd never felt so powerful.

At school that day, she got more attention than she ever had before. Her status had been upgraded from "cute" to "bombshell". Boys staring, boys whistling, one boy even walked into a door craning his neck to see her. Even her professors seemed to treat her differently. She felt a sense of control, and it added a little extra sashay to her hips as she walked down the halls.

Chad tried twice to speak to her, but she just walked away. The second time he yelled after her "whore!"

Allie just laughed. Maybe she was.

When she got to Mr. McConnell's at 4:30, the house was empty. She let the dogs out, and played with them as usual. In the living room she looked around carefully, hoping to find her White Knight accidentally kicked under the couch or tucked discreetly in an end table drawer. No luck. For a moment, she felt like he regretted Friday night. She wondered, was she stupid for dressing up this way? What if she made him uncomfortable and he sent her home? Then she remembered how good the attention at school felt. This didn't have to be about him. Why shouldn't she embrace her newfound confidence? Maybe she'd find another man to make her cum. Mr. McConnell didn't have a monopoly on incredible sex. He just had a monopoly on Allie having incredible sex- at least for now.

Allie did her best to focus on homework and do her usual job, taking care of the dogs and tidying up the kitchen. The boxes in the corner were gone. Just looking at the couch where she'd ridden Mr. McConnell soaked Allie's panties. She bit her bottom lip and tried to focus on something else. At 7, she heard the back door open; Mr. McConnell was home early! Allie pulled at her hair tie and shook out her waves as the pugs waddled into the kitchen. When he came in, she smiled warmly.

"Nice to see you again, Mr. McConnell." She stood up to walk over to him, mostly to let him see how good she looked.

In between jerking off to the video he'd accidentally recorded of them, Jack had debated all weekend what to do about Allie. Would she be angry with him? Or want to pretend as if the night never happened? Expecting she'd be up for another round seemed too much to ask. Most of all, he hoped she didn't feel guilty; Friday night was his fault, not hers.

Seeing her outfit and the way she carried herself answered all his questions. She wanted more. She wanted his fingers, his cock, his tongue... and she was going to get it. His eyes raked down her body and back up again. He wanted to grab that tiny waist and bury his face in her oversized breasts. He thought back to their conversation on Friday and paused for just a moment, realizing he had a very fun little game for them. He hoped she'd play along. He started by clearing his throat and saying "you look fantastic, Allie. You know though, I was supposed to punish you for your behavior on my couch last time, and I never did. The way you're dressed tells me it has to happen tonight."

Allie looked down, afraid he had changed his mind about not telling anyone. She couldn't risk her parents cutting off her tuition! She looked back up nervously and immediately realized that wasn't his intention. He wanted to fuck her again. She stepped so close she was almost touching him and smirked mischievously. "I was very, very naughty, Mr. McConnell. I should never have been bent over fucking myself on your couch when you walked in. And it's probably worse that I was moaning your name and fantasizing about your cock. In fact, I was tempted to do it again tonight, so I know I need discipline. Badly. What are you going to do about me?"

"Anything I want," he said firmly. "And if you don't agree to it, I might just change my mind and tell everyone what an orgasm hungry little slut you are. Do you understand?"

Allie nodded, excited to hear what he had in mind.

He went to the DVD rack, and reached around to the back. He pulled out a video and handed it to Allie. "Why don't I kennel the dogs, and you can start with putting this in the player."

Allie looked down at the video. This one was called "Bad Little Babysitters Do It All Vol 21". He definitely had a type. She went to the machine and bent forward at the waist to put the DVD in. From the way the skirt brushed her cheeks, Allie had a pretty good feeling he was getting a peek at her bare bottom teasing him from the edge of the hem.

She turned back to the couch, and Jack reached out to grab her. They began kissing, and he slid his hands across her bare midriff. His skin touching her shot through her like lightning, and Allie shivered. "What's the matter gorgeous?" he asked, kissing her neck. "Are you afraid of me?"

"Maybe a little," Allie breathed in his ear. "I like it." He slid his hand up her leg, boldly pushing past the bottom of her skirt up her thigh.

"I thought we could relax and watch another movie, since you liked the last one so much."

Allie blushed. "It was the first time I ever saw something so sexy."

"Well, seeing you bent over the couch with a toy inside you was the first time I've ever seen something so sexy. But I think you're purposely distracting me from what you know I need to do to you."

Allie looked at him, wide-eyed. He instantly pictured her the last time he saw her with those same wide eyes; kneeling while slobbering all over his dick shoved in her mouth. He felt his already hard cock jump in his pants, but paused. He wanted to take his time tonight and enjoy this. He told her to sit back and relax, and pushed play.

They began watching, but Jack couldn't take his eyes off Allie. When the first cock appeared on screen, she licked her lips in anticipation. He pulled her over into his lap, squeezing and stroking her bare ass cheeks under her skirt.

"You know Allie, you were very naughty the other night. And tonight you're teasing me again. Did you go without panties under your skirt all day today?"

"Oh, no, I have panties on. I'll show you." Allie stood up and bent over in front of him, flipping up her skirt to give him a full view of her round ass split by the lacy pink fabric.

Jack stood up continuing to stroke her cheeks, then licked his finger and slid it under the thong. He traced her body, brushing against her puckered little asshole. Allie shivered at the sensation, but didn't protest. His finger went further down, feeling the heat of her pussy and slowly sliding into her wetness. Allie moaned and leaned into him.

"You dirty little girl, look how wet you are already. You're practically drooling for me." He pulled his finger away and she looked back at him, watching him put the finger in his mouth to taste her. "I think you're trying to seduce me again. You just can't get enough cock. You know there are consequences for your behavior. Since you're so proud of those lacy little things, why don't you take off your skirt and let me get a good look?"

Allie, still with her back to him, did as she was told. She purposely wiggled her ass as she slid the skirt down, and then kicked off her shoes.

Jack kissed her neck as he groped her. "Turn around," he whispered. Allie did, and he stepped back. "And the sweater," he added, his throat dry. With a knowing smile, Allie crossed her arms and pulled the sweater over her head, then shook out her hair.

His eyes raked her up and down- she looked like a magazine centerfold. "If only I'd known sooner what you were wearing under all those clothes."

Allie smiled up at him. "This is new, actually. I bought it Saturday after class because I had an extra paycheck after putting in some overtime, and I was feeling especially sexy."

"If this is the result, you'll need to do a lot more overtime."

Allie reached behind her and unhooked her bra, then massaged her voluptuous curves without breaking eye contact. She closed the distance between them, and began to rub Jack's cock through his pants. He let out a moan, and Allie unbuckled his belt. Soon his pants were down, his cock was out, and she was stroking him. She eagerly got to her knees and took him deep in her mouth, stroking what she couldn't swallow.

Jack groaned and leaned in. He hadn't meant for it to go like this, but that little mouth of hers felt so fucking good. As naive as she was, Allie sucked a better cock than any woman he'd ever met. She stroked slowly at first, but sped up as he did. Christ, she was an expert at matching his pace, and he had no idea how she took so much of him down her throat without gagging. Jack put his hands on the back of her head, wrapping his fingers in her hair.

Soon his legs were trembling and a trickle of sweat ran down his back. He looked down to see her wide-eyed once again, staring up at his face as she expertly worked his cock. Those eyes... Jack couldn't hold back anymore, and with a guttural noise he came deep into Allie's throat. She swallowed it all, and kept working him until he pulled away.

"God, I don't know where a sweet little thing like you learned to suck cock like such a pro, but I'm grateful you did."

Allie, still wearing nothing but the tiny pink panties, laid back on the couch and began to tease her pussy as Mr. McConnell watched. He knew what she wanted, but he wasn't about to give in so easily.

He walked to the mantle while unbuttoning his shirt and reached behind a photo, bringing out the White Knight and the lube from where he'd hidden it. "Have you been missing something?"

"I have, but don't you want to taste me again?" she asked with an innocent pout.

Jack set the toy on the end table and reached for her. He slid his finger under her thong and buried it into her. She let out a moan and he felt his limp member tingle- christ she was addictive. He teased her for a few moments and then suddenly pulled his finger away and looked at her sternly. "You haven't learned a thing, have you Allie? Well, you're about to- now get on your hands and knees," he growled.

Allie was enjoying herself immensely, but feigned shy. She liked this little game. "I'm so sorry, Mr. McConnell. I can't help it. Your cock is so delicious, it's all I think about." She got down as she was told, and Jack caressed her cheeks slowly and gave her a squeeze.

"Such a naughty little thing," he breathed. He pulled his hand back and gave her ass a smack, enjoying watching her jump and her cheeks jiggle. Allie let out a small squeal as he made contact.

After a few more smacks, Allie's backside was red. He pulled the panties off her and buried his tongue in her soaking pussy. She tasted so good.

Allie looked up at a bad little babysitter getting titty fucked on the screen as she moaned and leaned her hips into Jack's mouth.

"Tell me, Allie," he murmured into her pussy. "Tell me what I want to hear."

"Mr. McConnell, I'm so sorry I was naughty. I know I'm a bad girl, and I'm so appreciative of your correcting me. I just can't resist you. You're so sexy, and your cock is just perfect. Lick me baby. I want you to eat my pussy and fuck my naughty little holes!"

Her words did the trick- Jack was hard again and ready to teach her a lesson.

He pulled his tongue away and a moment later Allie felt Mr. McConnell pushing his cock between her pussy lips to enter her wet little hole. She arched her hips back, welcoming him with a breathless "Yes baby!" Feeling him inside her from behind for the first time made her feel like she might cum immediately- he was hitting parts of her body she didn't know existed. She let out a long, low moan as she felt his hips meet hers. Soon he was thrusting hard, making her breasts jiggle and her cheeks clap. She was letting out soft little moans to the rhythm of his fucking. Watching her bent over like that gave Jack an idea. He was supposed to be disciplining her after all... He slowed down into long, rhythmic strokes, and Allie whimpered in frustration.

"Allie, you know you're being punished."

"You're not going to stop, are you?" Allie cried out, desperate to keep going.

Jack laughed. "No gorgeous, I'd never want to leave you unsatisfied. But I do need to make sure you learn your lesson, so you're going to do some things for me."

"Mmmm," Allie said, leaning back into him. "If you promise not to stop fucking me, I'll do anything you want."

"That's a good girl," he said to her. She heard him opening a cap on a bottle, and a moment later he was pressing the White Knight into her hand. He'd lubed it up for her. "I want you to start teasing your clitty with this. Make that red little cherry jump for me."

Allie did as she was told, and let out an "mmmm" as it pressed against her swollen pussy lips. She ground her hips against it. Mr. McConnell picked up his pace again, and Allie saw stars. Soon she was moaning while she humped the toy, and she felt her body tensing. She had never imagined sex could be this good. "Please Mr. McConnell, I know I've been a bad little slut, but I've been craving your cock so hard. I need you. Don't stop, baby. Don't stop until I cum all down that big thick cock of yours!"

Jack slowed his pace and Allie let out a noise of frustration. "You don't get to cum yet. I'll let you after you're finished with your punishment, but not before."

"Please Mr. McConnell, I'll do anything you say! Just don't make me wait."

Jack looked at the TV to see a babysitter in nothing but a bra and running shoes bent over, learning to take a cock in her ass. Perfect timing.

Allie heard the lube cap again and wondered what Mr. McConnell was up to. Wasn't her pussy wet enough? She felt soaked. A moment later, she felt her ass cheeks being spread and a gooeyness brushed against her asshole. Soon there was pressure, and she realized it was Mr. McConnell's finger!

"Ohh, oh what are you doing?" Allie moaned. She began to pull away, but when his cock started to slip out she pushed back again, allowing his finger to penetrate her just the tiniest bit.

"Punishing you Allie, for being a dirty little tease who can't keep her hands off her own pussy. I thought if you found out what happened to horny little college girls, you might learn to behave."

"Ohh, but I've never done this before!"

"Really Allie? You've never even slid your own finger in there? Just to try it out?"

"No! Why would I do that? I've never had anything in there at all!"

Jack's cock somehow got harder. She was a complete anal virgin; this was too good to be true.

"Because it can feel really, really good. Aren't you curious? I know you've never tried it, but until last week you'd never cum before, and you liked that."

"But this is different!" Allie protested.

Jack began to pull his cock back from her, but kept up the pressure from his finger. "Well, if you changed your mind about trusting me to punish you, we can get dressed right now and I can just call your parents instead."

"No! Don't do that! You promised!"

"Allie," he cooed, picking up the pace of his hips again, "are you telling me this doesn't feel good at all? Be honest with me." He stopped pushing with his finger and instead used it to massage the tight virgin hole he so desperately wanted to penetrate.

"Oh, ohhh unh hunh, it feels a little good. I like when you press against me like that. It's just so naughty! I'm not sure that we should do this. What if someone found out?"

"It is very naughty, Allie. And that's why you're going to let me do it. Because deep down you're a dirty little cock tease and you secretly like it." He kept fucking Allie with his cock while pushing forward a bit at a time with his finger.

"Mmm, you're not going to tell anyone, are you?" It was clear she was getting turned on now.

"Not as long as you keep doing what I say."

Allie didn't protest any further, and even leaned into him slightly, telling him it felt good as long as he didn't push it in too far. She was so tight, he didn't have to worry about that at first. However, before long he realized her hole was starting to spread for him. Not wanting to have another debate, he decided to distract her until he was inside. "Are you still teasing yourself with the vibrator, gorgeous?"

"Mmm yes. It feels so good against my clit. I'm so grateful for all the things you're teaching me, Mr. McConnell."

"And how does your pussy feel, Allie?"

"Ohh, you've got me so wet! And you're so big, I'm loving every inch. Fuck me, Mr. McConnell! I want to cum for you agai- Oh! What is that?" Allie suddenly cried out.

"Just my finger tip. I love the feel of you stretching around me. Give it a chance."

Allie let out a whimper, but the more Jack encouraged her by telling her how sexy she was, the more she warmed up to the sensation and leaned into him. Within a few minutes he had pushed his last knuckle into her puckered little hole and she was back to moaning and squeezing his shaft with her tight little pussy. Slowly he moved his finger around, stretching her. She was going to need to be nice and loose for what he had planned. He noticed that every time he pushed all the way in and pressed his knuckles around her opening she gasped, so he kept his finger deep inside her, hoping she wouldn't try to stop him again.

"Look at the screen, Allie," Jack instructed. Allie looked up to see the girl now in only her tennis shoes getting fucked hard. As the camera zoomed in, Allie realized it was going in the girl's asshole! She watched, mesmerized as always, by the penetration.