5 Tales of Punishment

by Brock Landers

  “You do it better than they do,” Matt said.

  “You’re damn right I do,” Jen replied. She spit on his cock and jerked him off some more, then slid back a little bit and dropped her head down and sucked on his balls. “What about this?” she said after popping them out of her mouth. “They do this too, don’t they?”

  “Yes,” he said.

  Jen grabbed his legs and pulled on them, sliding him further down the couch so his ass was hanging off the end of it. She grabbed his legs and spread them apart, then pushed them back, exposing his asshole, which she proceeded to lick. Matt shuddered and took a deep breath.

  “And this?” she said after tonguing his asshole for a few seconds. “This too?”

  “Sometimes,” he said hoarsely. “But only in the really nasty ones.”

  “But those are the ones you like, right? The nastier the better?”

  Matt nodded and tried to swallow but his throat was too dry and there was just a soft click. It was taking everything he had to keep from cumming all over her face.

  Jen smiled and went back to work on his asshole, licking it, sticking her tongue in it, running her tongue up his taint to the bottom of his balls, sucking on them for a bit, then running her tongue back down to his asshole.

  “Holy fucking shit,” Matt said as Jen slipped the tip of her tongue into his asshole. “I can’t believe you’re doing this.”

  But Jen was, and doing it well, sending lightning bolts of pleasure up his spine as she tongue-fucked his asshole while continuing to jerk his cock off. It felt so good Matt had to bite down on his bottom lip to keep from screaming aloud. It felt too good, in fact. If Jen kept this up, Matt was going to cum within half a minute.

  With this in mind, he quickly scooted back onto the couch, forcing Jen’s tongue to slip out of his asshole.

  Smiling up at him, loving every second of his discomfort, Jen said, “Too much for you, huh?”

  “Almost,” he replied.

  “You know,” she said. “In those movies you watch, the guys last hours. And here you are, ready to cum after just a couple minutes of the freaky shit.”

  “There’s a reason I just watch them and don’t take part in them,” Matt said.

  “Fair enough,” Jen said. “Lucky for you, there are plenty of things you can do that won’t leave you in any danger of cumming. Things that happen in those movies you love to watch.”

  Smiling, Jen climbed up onto the couch, lying on it lengthwise, her back to the cushions. As Matt stared, the grin on his face matching Jen’s, she grabbed ahold of her ankles and pulled her legs open, spreading her legs wide and leaving her pussy staring Matt right in the face.

  “Your turn,” Jen said.

  Matt got into a better position, then buried his face between her legs and started eating her pussy. Now this was something he was comfortable with.

  Matt didn’t have a problem licking a woman’s pussy. As far as he was concerned, it was a no-lose situation. You got your girl off without having to worry about cumming yourself. Plus he’d never come across a woman who didn’t like it. Not to mention, Jen’s pussy was perfectly manicured and impeccably clean. He could lick her snatch all night long and be completely content.

  He ate Jen’s pussy like an expert, constantly mixing things up, sucking on her clit for a little while then running his tongue up and down her snatch before sticking a couple fingers inside her then fucking her with his rigid tongue. Every once in a while he would shift the angle of his head a bit so he could look up at her. Seeing her look of pure enjoyment would always excite him even further and get him more excited.

  They were about five minutes in and Jen was really starting to get into it, the sounds of her breathing becoming more and more labored as she rose towards orgasm. She grabbed ahold of his hair and pulled him deeper into her pussy, jamming his face into her flesh, nearly smothering him. Then she wrapped her legs around his neck so Matt couldn’t go anywhere.

  “My god,” she said in a deep, guttural voice. “Right there, don’t stop. Right fucking there, don’t you dare fucking stop!”

  Matt had no intention of stopping even before Jen said anything. He was having way too much fun. Besides, he couldn’t have stopped even if he wanted to because of Jen’s legs smashing his face against her pussy.

  Jen bucked against his face more aggressively, screaming loudly now as she rose higher and higher towards orgasm. Her pussy was gushing, soaking Matt with its wetness and drenching his face as though he’d just gotten out of the shower.

  His confidence growing due to Jen’s excitement, Matt decided to kick things up a notch. He grabbed ahold of Jen’s ass cheeks and slid his thumb along the crack of her ass until he found her asshole. Using her copious pussy juices as lubrication, Matt rubbed the tip of thumb around the outer edge of Jen’s asshole a couple times to get her warmed up. Then slipped his thumb into her anus.

  Jen let out a sharp, yelping gasp and her body froze up for a couple seconds before exhaling in a rush as an orgasm immediately passed through her. Her pussy released another wave of juices, drenching his face even further.

  Jen’s legs shimmied for another few seconds, then she released her leglock on Matt’s head. Yanking on his hair, she lifted him up towards her face. She scooted forward and aggressively shoved her tongue down into his mouth while simultaneously grabbing ahold of his cock and jerking him off.

  “You like sticking your thumb in my ass, do you?” she said, breaking off their kiss with a yank on his hair.

  Matt nodded.

  “Is there anything else you want to stick in there?”

  He nodded again.

  Jen laughed. “Yeah, I’m sure there is. You want to stick your cock in my little asshole, don’t you?”

  He nodded yet again.

  “Well, I’ll make you a deal,” Jen said. “If you do a good enough job licking my asshole, then maybe, just maybe, I’ll even let you stick your cock inside it.”

  “Are you serious?”

  Jen nodded.

  “I didn’t know you were into that sort of thing.”

  “That’s because you never asked,” she said.

  “So you mean all this time, all I had to do was make an attempt and you would have let it happen?“

  “Well, not just any time,” Jen said. “But certainly there was a couple times, where if you would have made a move towards it, I wouldn’t have fought you on it.”

  Matt mentally smacked himself in the forehead with his palm.

  “And here you thought the only girls willing to do that were the ones you watched on your movies,” Jen said.

  “Little did I know I had one sharing a bed with me.”

  Jen shrugged. “Well, now you know,” she said. “But you’d better do a great job with your tongue down there or we’ll have to wait until a different night to take things to the next level.”

  “Oh, don’t worry about that,” Matt said. “I’ll lick like I’ve never licked before.”

  “We’ll just see about that,” Jen said. “We’ll just see.”

  To show Jen how serious he was, Matt dropped his head down and immediately started licking her asshole, his tongue moving up and down and around the edges.

  “Holy shit that feels so fucking good,” Jen said, staring down at him. Her eyes were wide and her mouth was turned up in a huge smile. Matt didn’t think he’d ever seen her so excited. So he kept pushing the envelope.

  Making his tongue rigid, he jammed it into Jen’s asshole as far as he could and started to tongue fuck her. Jen’s screams turned even more animated and her breathing rate increased.

  “Oh my fucking god!” she said. “Tongue-fuck my dirty shithole, baby. Just like that. Yes, YES, YES!”

  Getting off himself on Jen’s excitement, Matt spread her asscheeks with his hands, allowing him deeper access to her insides. Tilting his eyes up, he could see Jen fingering her snatch with one hand and squeezing and pinching one of her nipples with the other.

  Matt c
ontinued working Jen’s asshole as aggressively as he could, jamming his tongue further and further inside it as she continued playing with herself, which opened her anus wider, allowing him deeper inside.

  Just as Jen was about to cum again, she transferred the hand that was squeezing her nipple to Matt’s hair and held his head in place, his tongued jammed deep into her asshole while she rubbed her clit forcefully.

  “Fuck, FUCK, FUCK!” Jen screamed. “I’m gonna fucking cum again!”

  Half a minute later she did exactly that, her pussy squirting juices everywhere again and her body shaking and shivering for nearly ten seconds before falling still this time.

  Using his hair, Jen pulled Matt’s head up towards her own. She pressed her forehead against his and said, “Okay. I think you earned the right to fuck my ass.”

  Smiling, Matt slipped his tongue into her mouth and they made out for a little bit while Jen ran her hand down to his cock and started playing with it.

  Matt was excited. Probably too excited, really. He’d dreamt about fucking Jen in the ass ever since he’d met her but figured it would never come to pass. And he was so wound up after all the foreplay that he doubted he’d last long. But those were the breaks. It was better to have fucked Jen’s ass for a couple minutes than not at all. Or something like that.

  So he broke off the kiss and slid back down her body until he was standing on the floor. He was tempted to put Jen on her hands and knees so he could fuck her doggy-style, but considering how much he liked that position, he was sure it would just serve lessen the (already limited) amount of time he’d be able to fuck her before cumming, so he kept her on her back.

  Matt grabbed Jen’s ankles and pulled her legs up, lifting her ass off the cushions of the couch and bringing her asshole closer to his cock. Jen hooked her arms under her knees to hold her legs in place and looked at him with a filthy little grin.

  “Are you ready for this?” Matt asked her.

  “I am,” Jen said. “The real question is, are you?”

  “Hell yes,” he replied.

  “Then do it,” she said. “Stick that hard cock of yours into my pretty little asshole.”

  Matt couldn’t turn down a request like that, so he did as Jen had asked, grabbing ahold of his cock and sticking the tip of it against her asshole, then taking a deep breath and pushing his hips forward.

  The tip of his cock slipped into Jen’s asshole. It was a tight fit but not uncomfortable. Just weird. Unlike her pussy, Jen’s asshole provided consistent pressure to every centimeter of his cock at one. Plus it was tight as shit.

  But it felt incredible. So good, in fact, that Matt was afraid he was going to cum just from breaking the seal. After entering Jen, he stayed completely still, taking a couple of deep breaths while trying not to move at all.

  Jen could tell the difference too. She was taking short, shallow breaths and her eyes were closed in concentration. A strange combination of pleasure and pain played over her features.

  Matt knew how she felt. While the pleasure was undeniable, there was a certain level of discomfort there too. Too bad he didn’t have any lube; that would certainly help. Well, next time he’d know. For now, he would just have to make the best out of it.

  Jen helped things a bit, spitting onto her hand and rubbing her saliva over his cock. That helped some, allowing him to move a little bit without too much effort. And when Jen started rubbing her clit it helped even more.

  The more she played with herself, the more she relaxed, and the more her anus loosened up. After half a minute or so, Matt was able to move at a slow but consistent pace, his cock going deeper and deeper into Jen’s asshole with every pump.

  “Your asshole is so fucking tight,” Matt said, staring down at her with an intense gaze.

  Jen just nodded her head and continued playing with her pussy.

  “It feels good though,” Matt said. “Doesn’t it?”

  Jen nodded again.

  And it did to Matt too, despite the tightness. There was just something about fucking Jen in the ass that was so nasty, so perverted, so flat-out wrong that it turned him on like crazy just thinking about it. And even though he was barely moving against her at all, it took everything he had to keep from cumming.

  Matt leaned forward and stuck his tongue into Jen’s mouth, hoping to take his mind off how close he was to orgasm, but it didn’t work. If anything, her lips on his felt so good that it brought him even closer to cumming. Which wasn’t a surprise; kissing while fucking almost always had that effect on him.

  “I don’t know how much longer I can last,” he said, pulling his mouth off Jen’s for a moment.

  “That’s okay,” she said, speaking desperately. “I don’t know how much more I can take.”

  “In fact, I think I’m ready to cum right now.”

  “I think that’s a great idea,” Jen said.

  “Yeah?” Matt asked.

  Jen nodded her head. Then she grabbed the back of Matt’s head and pulled him closer to her. She knew how much he liked kissing while fucking and figured it would get him to finish up that much quicker.

  She was right.

  Matt started moving more rapidly against her, still not all the quickly but at a faster pace than any other time since he’d stuck his cock in her ass. In the end, it was more than enough.

  Five seconds later, he was ready to cum.

  “Shit, shit, shit,” he said under his breath, just like he always did before he came.

  “Spray my stomach with it,” Jen said, staring him right in the eyes, knowing exactly what was coming.

  Matt nodded as his orgasm arrived and pulled his cock out of Jen’s asshole and leaned forward, so his cock was lying atop her pussy. Jen reached down and grabbed ahold of his cock and jerked him off, bringing him the final last little bit to the edge, and then over it. He came right away, shooting his seed all over Jen’s stomach, just like she’d requested.

  It was a massive load, four full pumps, covering Jen’s washboard stomach with his pale white sperm.

  “That wasn’t quite what I expected,” Matt said after he was done, offering her a little smile.

  “Me neither,” Jen replied. “But it wasn’t bad.”

  “No, not at all,” he said. “It was just . . . different.”

  “Yeah,” she said. “Much different.”

  They shared a laugh then a kiss.

  “Next time we’ll have to prepare better,” Jen said.

  This surprised Matt a bit. “There’s going to be a next time?”

  “Sure,” she said. “You do want to try it again, right?”

  “Well, yeah,” he said. “I just figured you wouldn’t.”

  “Why not?”

  Matt shrugged.

  “Don’t get me wrong,” Jen said. “It wasn’t great. But it wasn’t bad either. And it was almost good. A little more warm up next time, some drinks beforehand and a little bit more attention to my asshole before you stick your cock in there, plus a whole lot of lube, and I think I could really get into it.”

  “Yeah?” Matt said.

  Jen nodded. “It was intense,” she said. “More intense than usual.”

  “That’s the truth,” he said.

  “If done properly, I think it would cause one hell of a monster orgasm.”

  “I can see that,” Dan said, thinking about how hard he came after just having his cock in her ass for a short time. “I can totally see that.”

  “Then it’s a date,” Jen said. “Saturday night. We’ll do it the right way.”

  “Sounds great,” Matt said. He couldn’t wait.

  #####

  PUNISHING THE TEEN

  FILTHY LITTLE TEEN: VOLUME TWO

  BROCK LANDERS

  I was out drinking with the guys when my phone buzzed. I pulled it out of my pocket and checked the screen. It was from Jamie. My pulse quickening, I stepped out the back door into the smoking area and flipped open my phone.

  “Hey Jamie, what’s up?” I
said.

  “Are you busy?” she replied.

  “Not really. Just at a bar with some friends.”

  “Do you have a problem bailing on them?”

  I laughed. Jamie wasn’t one for beating around the bush. It was one of the reasons I dug her so much. The fact that she was an 18-year hardbody with a insatiable lust for nasty sex was the main one, but her attitude played a major part in that.

  “Not if I have a good reason to,” I said.

  “Well, let’s just put it this way,” Jamie said. “I’ve been a bad girl and I need to be punished. Severely. Is that a good enough reason?”

  “I’ll be there in twenty minutes,” I said, my cock already starting to get hard just thinking about it.

  “I’ll be waiting.”

  I closed my phone and went back into the bar. I told my friends what was up and they bid me godspeed. They were cool with it; after all, that’s pretty much the only reason why we were out in the first place, to try and score. There was no use passing on a sure thing solely on the hope of getting something later. Besides, even if I did end up going home with someone at the end of the night, there was no way in hell she’d be half the freak that Jamie was. It simply wasn’t possible.

  #

  I showed up at Jamie’s door half an hour later.

  “It’s about fucking time,” she said upon opening up, her voice laced with disdain, as usual. If there was one thing that was consistent about Jamie it was her defiant attitude. But since we were just fuck-buddies and not in a relationship of any kind, I found it endearing instead of annoying. Plus it made the sex infinitely more interesting. It was far easier to get truly nasty with a girl who acted like a punk than one that was sweet and innocent.

  “Deal with it,” I said, pushing right back at her with attitude of my own. Handling it any other way would just encourage her more. And the last thing she needed was more encouragement. She had more than enough attitude without it. If you let her run you over without talking back she was all but intolerable.

  “Well, come on in already,” she said, opening the door wide. She was looking incredible as usual, wearing a white long-sleeved blouse with black dots covering it, white panties, and black, ankle-high, two-inch heeled boots. Her legs looked a hundred yards long, and her firm, thin body was as enticing as always. Even in her heels Jamie was a good 10 inches shorter than me but she held herself with so much confidence that she rarely seemed as small as she truly was.