24 Aggressive & Filthy Stories 2

by Heather Monroe

“Holy fucking shit,” Andrew said between deep, gasping breaths. The pained look on his face had come back with a vengeance and his while his hand was still around his cock, he was no longer jerking himself off. The knee that he had hooked his arm around the back of was mere centimeters from his mouth as he held his ass open for her.

  “Keep playing with yourself,” Mandy said. “Don’t let up now.”

  Gritting his teeth, Andrew went back to jerking himself off.

  “That’s a good boy,” Mandy said as she started moving her hips forward and back, pumping Andrew’s ass with her cock, giving it to him balls-deep every time.

  She gave him the whole dildo in long, slow thrusts at first, but quickly sped things up, pumping his asshole with her cock at a pretty quick pace within half a minute.

  It was obvious from the look on Andrew’s face that was struggling with it quite a bit. But Mandy didn’t care at this point. She was going to give it to him how she wanted to, not how he wanted it.

  “Bite your fucking knee if it hurts,” Mandy said. “Don’t even think about pushing my cock out of your asshole. Bite your fucking knee. You bite your fucking knee if it’s too much for you to handle.”

  So Andrew did just that, biting down on the skin above his kneecap while Mandy continued fucking his asshole with her cock, giving it to him hard and fast now, hammering the dildo in and out of his anus while he groaned and took deep, gasping breaths.

  “That’s right,” Mandy said, pummeling him harder now. “Take that dick. Take it deep inside your asshole.”

  Andrew’s eyes were closed and his mouth was open but his dick was still hard, which meant that no matter how much it hurt, he was still enjoying himself on some level.

  And so was Mandy. Things weren’t nearly as rough as they were with some of her regular partners, but popping a young man’s anal cherry more than made up for the lack of aggression in this session.

  “Am I the best dick you’ve ever had?” Mandy asked.

  “Yes, mistress, ” Andrew said, his voice barely above a whisper.

  “I can’t hear you,” Mandy said.

  “Yes, mistress,” Andrew said again, louder this time.

  “I want to hear you say it,” she said, glaring down at him with an annoyed face even though she was thoroughly enjoying herself, and especially Andrew’s discomfort. “Tell me I’m the best dick you’ve ever had.”

  “You’re the best dick I’ve ever had,” he said between gasps and moans.

  “That’s what I like to hear,” Mandy said, smiling sweetly now.

  She leaned forward so her body was lying atop Andrew’s and her face was right above him, no more than two inches away.

  “Tell me you like it,” she said, staring right at him. “Tell me you fucking like it.”

  “I like it,” Andrew said.

  “Like you mean it,” Mandy said.

  “I love it,” he said with more emotion. “I fucking love it.”

  “Yeah?” Mandy said, still pounding his asshole with her cock. “You’re my fucking bitch, aren’t you?”

  “Yes, mistress,” Andrew said.

  “Tell me you’re my fucking bitch,” she said.

  “I’m your fucking bitch.”

  “Again,” Mandy said. “Tell me you’re my fucking little bitch.”

  “I’m your fucking little bitch,” Andrew said.

  Smiling wickedly, enjoying herself immensely, Mandy bent over a little further and jammed her tongue into Andrew’s mouth, roughly exploring around for a few seconds before pulling back.

  She loved having all the control, all the power over a man. Telling him what to do, what he was going to do, what he was going to enjoy. It was more tempting than the most addictive drug, as intoxicating as the strongest aphrodisiac. But like all things, it must come to an end, and from the look on Andrew’s face and the bulging hardness of his cock, that end was near.

  “You want to cum, don’t you?” she asked him.

  Andrew nodded.

  “You want to cum and for this to be over, right?”

  “Yes, mistress,” he said.

  “Don’t worry,” Mandy said. “It will be soon, I promise. But first I need something from you.”

  “Anything, mistress,” Andrew said.

  “I need you to grab your other leg and pull your knees back a little further,” she said. “Open yourself up more to me so I can fuck you like you deserve to be fucked. Then I’ll help you cum.”

  Andrew did as he was told, hooking his arm around his other knee and pulling back on both of them so his ass was sticking up in the air.

  “That’s a good boy,” Mandy said, lifting herself up higher, towering over Andrew now.

  It wasn’t quite the piledriver position, but it was close. And from here, Mandy could force her cock deeper into Andrew’s asshole than it had been all night.

  “It’s time to take the training wheels off,” she said. “It’s time for you to see what it’s really like to get fucked in the ass. That’s what you want, right?”

  “Yes, mistress,” Andrew said. But he didn’t seem too enthusiastic about it. Which was fine by Mandy. At this point, she could care less how Andrew felt.

  She put her legs in front of her hips and scooted forward, giving herself the best angle to stick her cock deep in Andrew’s ass, then pushed her hips forward, jamming the dildo deeper into his ass than it had been all night.

  Andrew yelped and flinched and his eyes widened suddenly.

  In a condescending tone, Mandy said, “Oooohhhh, poor baby, was that too much dick for you?”

  But she didn’t let Andrew answer. She just continued pummeling his asshole with her cock, driving it deep into his anus, slamming her hips into his asscheeks with every thrust.

  “Take my cock,” she said, growling the words now. “Tell me you can take my cock. Tell me you can take all of my cock.”

  “I can take it,” Andrew said, barely able to get the words out. “I can take all of your cock.”

  “Yes you can,” Mandy said. “Yes you can! You’re a good little boy, aren’t you? You’re a good little ass slut!”

  “Yes I am,” Andrew said. “Yes I am!”

  “Now jerk your cock off,” she said. “Jerk yourself off while I fuck your asshole.”

  Andrew did as he was told, just as he had been all afternoon. But he didn’t seem to be making any progress towards cumming, so Mandy decided to help him out.

  “Do you want me to help you cum?” she asked.

  “Yes please,” Andrew said.

  “Yeah?” Mandy asked. “Do you want me to jerk you off so you can cum?”

  “Yes, mistress.”

  “Then move your hand,” she said.

  After Andrew released his cock, Mandy reached over and again grabbed the bottle of lube. While still fucking his asshole (albeit more slowly for the moment) she squeezed the bottle, squirting the liquid all over Andrew’s cock. Then she dropped the bottle and worked the lube all around, coating his cock with it.

  Once that was done, Mandy went back to fucking Andrew’s ass with a renewed intensity, giving it to him balls-deep again, pummeling him with her cock, bottoming out with every thrust.

  As Andrew grunted and groaned, Mandy went to work on his cock, jerking him off just as aggressively as she was fucking his ass, the lube coating his cock making her job easy.

  “Holy fucking shit,” Andrew said, clearly going through a wide range of feelings from the look on his face—part excitement, part pleasure, part pain, and part confusion.

  “You like that, baby?” Mandy asked. “You like when I jerk you off while I fuck your asshole?”

  “Yes, mistress,” Andrew said. His eyes were wide and his entire body was quivering as though is was hooked up to a low dose of electricity.

  “Tell me,” she said, her hand flying over his rock-hard cock. “I want to hear you say it!”

  “I love it when you fuck my ass and jerk me off!”

  “That’s it,” Mandy said. Th
ey were both talking loudly now, if not quite outright screaming. “Are you ready to cum?”

  “Yes, mistress,” Andrew said.

  “You can cum whenever you want,” she said. “But you’re going to have to do it while I’m pounding your asshole. Do you think you can do that?”

  “I don’t know, mistress!” Andrew said. He was breathing heavily and his whole body was heaving. “I don’t know!”

  “Well, if you want to cum that’s how it’s going to have to happen,” she said, smiling down on him like a demon.

  Andrew’s eyes were closed now and his face was screwed up in a grimace. He was obviously trying to cum but not quite able to get himself there.

  Mandy watched him struggle with it for a minute while still hammering away at his asshole and jerking him off like a madwomen before finally taking mercy on him. Reaching out with her free hand, she cupped his ballsack and started to rub his testicles.

  Andrew’s eyes immediately opened wide and a gasp of pleasure escaped from his throat.

  “I take it you like that?” Mandy said.

  Andrew nodded. At this point, she doubted that he could talk at all.

  “Is it going to make you cum?” she asked.

  He nodded again, more emphatically this time.

  “Then cum for me, big boy,” Mandy said, putting everything she had into working him over, fucking his ass, jerking him off, and rubbing his balls together all at the same time. “Cum all over yourself for me!”

  A few seconds later, Andrew’s entire body tensed up, then released. He cursed under his breath and let out a long, low groan as his cock shot out stream after stream of white cum, sending it up into the air only to splash down on his stomach and chest.

  Leaving her dildo planted in Andrew’s ass, Mandy continued to work his cock and balls until they were completely dry, squeezing every last drop out of them before releasing them from her grip.

  As Andrew shuddered and tried to catch his breath after his intense orgasm, Mandy let her cock slip out of his asshole.

  “Well, what did you think?” she asked, smirking down at him.

  “I think that was fucking insane,” Andrew said. His mouth was fixed in a goofy, exhausted smile.

  “Did you enjoy yourself?”

  “Hell yes,” he said. “I fucking loved it.”

  “Is it something you might want to do again?”

  “Not right away,” Andrew said, laughing. “But yeah, I’d love to do it again sometime.”

  “With me?” Mandy asked.

  “If you’d have me,” he said.

  “I would,” she said. “Under two conditions.”

  “Anything,” Andrew said. “Just tell me what you need from me.”

  “First, you have to understand that today was as mellow as it gets. If you want me to fuck you in the ass again, it’s going to get a whole lot more crazy.”

  Andrew’s smile grew wider. “That sounds great!”

  “And two,” Mandy said, running her finger along his stomach and chest as she did so. “You have to prove to me that you truly want to do this again.”

  “And how do I do that?” Andrew asked, still smiling.

  Mandy altered the path of her finger to collect a good amount of Andrew’s cum from his stomach. Once she had a large blob of it on the tip of her finger, she held it out towards Andrew’s mouth.

  “By eating this,” she said.

  Andrew’s smile faded quickly.

  “Seriously?” he asked.

  Mandy nodded.

  Andrew stared at her finger for a moment, then took a deep breath and said, “Fuck it.” Then he opened up his mouth.

  Mandy slipped her finger between his lips. Andrew sucked his own cum off her finger and held it in his mouth for a moment.

  “Swallow it,” Mandy said.

  Andrew tilted his head back and swallowed it down.

  Smiling, Mandy said, “Good boy,” and stood up. After helping Andrew to his feet, she gave him a smack on the ass and told him to go jump in the shower and get cleaned up.

  As he walked down the hall towards the bathroom, Mandy said, “And Andrew?”

  He turned around. “Yes?”

  “You did good today.”

  “Thanks,” he replied, smiling shyly. “You were incredible.”

  “My pleasure,” Mandy said, staring at his tight little ass as he turned and headed towards the bathroom.

  Mandy wasn’t one for letting men fuck her anymore, but she might just make an exception in Andrew’s case next time. After she’d fucked him first, of course.

  #####

  AGGRESSIVE & FILTHY: VOLUME 33

  Most people think of college as the best times of their lives. For good reason. College is where you can do those things that you have always wanted to do but real life and that voice inside your head doesn’t allow you to. Thankfully, reason and rational thought can be easily quieted by one thing, alcohol. Lots of alcohol.

  Johnny was handsome. He was just shy of six feet tall, in tremendous shape, and had a back and shoulders that made me wet just looking at them. His build was due to spending hours at the gym and occasionally going to class. He lived as most college students do, enjoying each day as it came and hoping his parents would continue to finance the next semester when his grades were mediocre at best. He was also a man whore. He had spent the night with many of my friends and they all agreed that it was a night worth spending. That made him off limits, at least when I was sober.

  Dorm dances were normally nights I would stay in and study since I was extremely self conscience about my two left feet. Tonight, however, was different. I had promised my best friend that I would go with her to the dance since she was hoping to hook up with her future husband as she referred to him. I had a feeling that her future husband was more like her future pray-I-had-enough-to-drink-that-I-can-talk-myself-into-thinking-it-was-all-a-dream-and-that-evening-never-happened but who was I to judge? So, I put on my little black dress and high heels and left my room hoping she’d leave with him early enough that I wouldn’t have time to make a total ass out of myself on the dance floor.

  Within minutes of arriving, I had downed a few shots and started to feel my anxiety melting away, exchanged by the false courage that alcohol so easily provides. I saw Johnny, breathed deep, and turned the other way. I was not about to end up in bed with this guy who so easily seemed to have that effect on all my friends.

  I steered myself toward Brandon. He was in my English Lit class and was just under six feet tall and perfectly average. Brandon was safe. Brandon would be my choice for dancing and drinking and no way would I end up taking my clothes off. Sorry Brandon but we girls do this a lot. We find that one safe guy who will never exit the friend zone and that’s how we maneuver our way through an evening when we know we will be drinking heavily. Guys like Brandon must hate girls like me. We must seem like a tease but if Brandon had known to ask me right up front, Will we end up together? I would have told him no and he could have saved himself some heartache. Instead, Brandon and I laughed, toasted, drank, and did something slightly resembling dancing. It probably looked more like I was having a seizure but I didn’t care. I was drunk and having a blast.

  Soon Brandon must have realized that he was in the friend zone or maybe he met someone who felt his average features were more than average in her eyes because he politely excused himself, handed me off to the guy next to him on the dance floor and left. I looked up half in shock and half laughing that Brandon wasn’t going to put up with my crap for the whole night and saw Johnny grinning back at me. SHIT! We slow danced for the remainder of the song and when it ended I quickly excused myself and headed back to the bar.

  I ordered another shot, reached into my purse and saw a twenty get passed over me, another glass poured and Johnny handed me my drink. “To you,” he said and downed his glass. Fuck. There are always those times in your life when you know, regardless of how drunk you are, where things are going to end up. I had a decision to mak
e and fast. If I didn’t want to end up with my panties lost in Johnny’s room this evening, I needed to say I didn’t feel well and run back to my dorm, lock the door and not let myself out until my blood alcohol level returned to zero. But as he stood there in his black shirt and black pants with his built body underneath I wanted nothing more than to see what all the fuss was about. “To us,” I replied.

  Things get fuzzy when shots are on the menu but the sex was crystal clear. It all started with a backrub. An innocent kind-hearted gesture. Bullshit. Don’t ever believe that ladies. All backrubs are is a way to get physical without your pretty little head thinking it’s a gateway to sex. Trust me, it’s like walking down the gangplank to a waiting plane. You might not end up in the air within a few minutes but the chances of you running screaming the other way in time aren’t good at all.

  I was lying facedown on his bed with my little black dress straining to keep my ass covered. My heels had long ago been removed and were dropped by his bedroom door. He straddled my ass and began to rub my shoulders and neck. That’s nice. He slowly was working my muscles and if he wasn’t careful, I’d be asleep in minutes. Nope, he’d done this before because his hands were working my back area and reaching around to the sides near my breasts. He didn’t touch my breasts, not yet. But he knew enough that my nipples had turned rock hard in anticipation and my breathing was becoming more shallow by the minute.

  Then, he got up off my ass which was getting very restless during the massage and moved to the end of the bed. Whew. That was close. “You’re legs and feet must be sore from dancing in those shoes.” He softly lifted a foot and began to rub. This was nice. My body was relaxing as if it had been fooled into thinking that he was trying to make a pass at me when he really wasn’t. That was a relief. Then, he began to rub the other foot, then my calves. He continued to make his way up my legs to my thighs. Hello! The tips of his fingers got to within an inch of the cloth of my panties and I was gasping for air. Remain calm, remain calm. You don’t want him to know that you want nothing more than to fuck his brains out right now! Again, he moved both hands up and down my thighs. Accidently brushing my panties from time to time. He never said a word but he had to have noticed that each time the fabric was more and more wet. Then, he started massaging my ass. I sucked in air as he reached up and grabbed both cheeks in his hands. “You’re so tense.” You have no fucking idea! My pussy was on fire and yearning for his hands to massage it too!