After all, for the most part, a more energetic partner is a better partner, no matter what the set-up, and when Mandy was doing it the way she wanted, she was happier, which made her more energetic, which meant that both of them had a better time.
So now, even when Mandy was pegging a man for the first time, she didn’t even bother asking him how he wanted it. She just gave it to him however she saw fit on that particular day and let the chips fall where they may.
Take Andrew, for example. It was not only his first time with Mandy, but it was his first time getting fucked in the ass by anyone. She got hooked up with him through one of her friends, a girl named Casey.
Andrew and Casey knew each other, and Casey came to find out that Andrew had always wanted to be pegged by a woman but had always been afraid to ask whoever he was dating at the time, for fear that it would ruin the relationship. Eventually, Andrew had got drunk enough to ask Casey to do it to him, but she was a submissive by nature, so she told Mandy about it.
Once Mandy heard about it, she was all for it, even more so once she was told all the particulars. Mandy agreed to give Andrew exactly what he wanted, as long as he understood that she was going to be in total control. Once Andrew agreed to Mandy’s terms, a date was set.
#
On the day of Andrew’s deflowering, he knocked on Mandy’s door precisely on time. She answered the door all ready to go, adorned in black leather, from her thigh-high boots to her mini-skirt to her jacket. Plus she had on black sunglasses and was wearing her long, raven-colored hair down.
In addition, Mandy had already strapped on her dildo. It was one of her smaller ones, right about 6-inches long and medium width. Even though she was going to have her way with Andrew, she didn’t want to hurt him (at least not too badly) and since he’d never been ass-fucked before she decided not to start him out with too large a dildo.
Mandy invited Andrew inside and told him to have a seat on the couch. He did as he was told without hesitation. It was a good start.
Mandy was pleased by Andrew’s appearance. He was a young man, no more than 22 years old, with a lanky but well-maintained body, a full head of brownish-blonde hair and boyish good looks. He seemed nice enough, with a shy little smile and blue, intelligent eyes. From the way he carried himself he wasn’t cocky and not even be all that confident but not completely shy and self-contained either. All in all he seemed like a good kid, and he definitely was attractive.
Mandy couldn’t wait to make him her bitch.
“So this is your first time getting fucked in the ass, right?” she asked, sitting down next to him on the couch. She couldn’t help but notice that his eyes went right to the dildo which was strapped to her waist.
“Yes,” Andrew replied, his face blushing a little bit.
“It’s nothing to be embarrassed about,” Mandy said.
“I know,” Andrew said. “It’s just a bit . . . weird to be hearing out loud like that.”
“Well you’d better get used to it,” she said, flashing him a smile. “Because you’re going to hear a whole lot more of that sort of thing. And worse.”
“I’ll try to,” Andrew said, smiling back.
“Have you ever had anything in your ass?”
“Not really,” Andrew said.
“No?” Mandy asked. “Or not really. Which one?”
“I’m not sure,” he replied. “I’ve had a girl lick my asshole with her tongue but I don’t know if that counts.”
“Not really,” she replied. “Is that it?”
Andrew nodded.
“So I get to pop your cherry,” Mandy said.
“Yes you do,” he said.
“I hope you don’t think I’m going to take it easy on you just because it’s your first time.”
“I don’t,” Andrew said.
“Good,” Mandy said. “Then let’s get to it. On your hands and knees.”
Andrew did as he was told.
“Very good,” Mandy said.
She climbed off the couch and stepped with one leg over his body, so she was straddling him, her ass resting on his lower back.
“For the rest of today, you are my bitch,” Mandy said. “You will do what I tell you to, without hesitation, understand?”
“Yes,” Andrew said.
“And if I sense any reluctance, I’m going to punish you, got it?”
Andrew nodded.
Mandy grabbed a handful of his hair and tugged on it, yanking his head back. “When I ask you a question, you answer me,” she said. “With words. Not with a nod.”
“Okay,” Andrew said.
She leaned over and gave him a light smack on the cheek. “And you are to call me mistress. Always. Understand?”
“Yes, mistress,” he replied.
“Very good,” Mandy said. She released his hair. “Now give me a ride around the room. I want to see how strong you are.”
“Yes, mistress,” Andrew said.
He started to crawl while Mandy rode his back.
“Around the couch and right back here,” Mandy said. “That’s a good boy. Be a good little bitch for me.”
Andrew made the trip around the couch in less than minute. He didn’t seem to have any problems at all carrying her.
“Not bad,” Mandy said, climbing off of him. “Not bad at all. You’re a strong little bitch, aren’t you?”
Andrew just looked at her. But he was new at this so Mandy gave him another chance.
“Aren’t you?” she asked, raising her eyebrows and giving him a look.
“Yes, mistress,” Andrew said.
“That’s better,” she replied, sitting down on the couch. “Now take your clothes off. I want to see your cock.”
Andrew did as he was told, stripping down until he was naked. His cock wasn’t yet hard but it was pretty chubby. Not to mention larger than average. It was obvious he was enjoying himself so far. Mandy grabbed ahold of his cock and started to stroke it.
Andrew let out a low groan and his cock immediately started growing larger.
“Oh, you like that do you?” Mandy asked. “You like it when I stroke your cock?”
“Yes, mistress,” Andrew said.
“Well don’t get used to it,” she said. “Because this is just a special treat. Maybe, just maybe, if you take it in the ass like a champ, then maybe I’ll do you the pleasure of touching your cock again before the day is up. But only if you’re lucky. Understand?”
“Yes, mistress,” he said again, between deep breaths.
“Good,” Mandy said, letting go of his cock. She spun around and climbed up onto her knees on the couch so her ass was facing him. “Now get on your knees.”
Andrew dropped to the floor. His head was at the same level as her ass now, just a few inches away.
Mandy turned her upper body so she was looking at him but her ass stayed in the same place, right in front of his face. “I’ve been nice to you because it’s your first time and all,” she said. “But now I’m ready to play.”
As soon as she finished her sentence, Mandy grabbed Andrew by the back of his head and pulled him towards her ass, smashing his face against her flesh so his tongue was touching her asshole.
“Get your face in there,” she said, holding Andrew in place by his hair. “Get your fucking face in there. Lick that fucking asshole.”
Andrew did as he was told, exploring her asshole with his tongue, constantly moving it around, mixing things up as best he could.
Mandy could feel his hot breath on her skin, could feel his nose pressing against the crack of her ass. “Grab your cock,” she said to him.
Again, Andrew did as he was told.
“Now play with yourself,” Mandy said. “Jerk yourself off while you lick my asshole clean.”
She released her hold on Andrew head and began bouncing her ass up and down, riding his tongue.
“That’s it,” Mandy said. “Keep your face right there while I ride your tongue. Right fucking there. And keep playing with you
r cock. Don’t stop.”
Mandy bounced harder and harder on Andrew’s face, forcing his tongue deeper and deeper inside her asshole. After half a minute, she caught him trying to back away to catch his breath.
“Where the fuck do you think you’re going?” she asked, once again grabbing ahold of his hair and holding him in place, his face smashed up against her ass, his tongue deep inside her asshole. “Don’t fucking move. Don’t fucking move until I tell you to.”
So Andrew didn’t, keeping his head still as Mandy rode his tongue with her asshole while continuing to smash his face up against her flesh.
“Right there, right fucking there!” she cried, hammering her ass back against Andrew now. “Don’t move, don’t you dare move! I’m gonna cum! I’m gonna fucking cum!”
And cum she did, her body freezing up for a moment before exploding in a mini-orgasm, sending juices shooting out of her pussy and onto Andrew.
“Not bad,” Mandy said after her mini-orgasm had passed. “Not too fucking bad at all. You’re off to a good little start my friend,” she said. After spinning around on the couch again so she was facing him, with her strap-on sticking up the air, practically touching his chin, she added, “But now it’s time to get the party started for real.”
Andrew took a deep breath to help prepare himself.
Mandy laughed softly and jerked off her cock. “Are you ready for this?” she asked.
Andrew started to nod, but said, “Yes, mistress,” shortly after.
“Is this your first time sucking cock?” Mandy said.
“Yes, mistress,” Andrew replied.
“Are you scared?” she asked, flashing him a devilish smile.
“Should I be?” he countered, a concerned little grin playing on his lips.
“Maybe,” Mandy said. She grabbed ahold of her cock and smacked Andrew in the face with it a couple of times. “Do you think you handle this whole thing?”
“Yeah,” he said.
“Are you sure?” she replied.
“No,” Andrew said, smiling.
“Well let’s find out,” Mandy said. “Open up, big boy.”
Andrew did as he was told. Mandy grabbed him by the hair and pulled him towards her cock, then slid it into his mouth.
“There you go,” she said. “That’s a good boy. Suck that dick.”
And Andrew did, bobbing up and down on Mandy’s strap-on, taking it almost halfway down every time before popping back up. Saliva was dripping out of his mouth and gagging sounds were coming from his throat.
“Work that cock, baby, work it,” Mandy said. She leaned back and put her hands behind her head in a relaxed position and stared down at Andrew as he sucked her cock. “See how far down you can take it.”
Andrew pushed his head down on Mandy’s cock until it was almost three-quarters of the way gone. Then he started to gag and pulled his head back and gasped for air.
“Not so easy, is it?” Mandy asked.
Andrew shook his head while still trying to catch his breath.
“What?” Mandy said. “I didn’t hear you.”
“No, mistress,” he replied, talking through deep breaths. “It’s not easy.”
“Do it again,” she said. “And don’t stop until the whole thing has disappeared this time.”
“Yes mistress,” Andrew said. He took a deep breath then dove in.
Andrew almost had the whole cock down his throat when he started to cough. It looked like he was going to pull away, so Mandy reached down and held the back of his head so he couldn’t move.
“Don’t go anywhere,” she said. “You haven’t taken the whole thing yet.”
Then she pulled Andrew’s head forward, forcing the last inch of her cock into his throat.
“That’s a good boy,” Mandy said, keeping her hands on the back of Andrew’s head as he gagged and coughed and strained for breath. “Way to deepthroat that cock. Now hold it for a few seconds. Hold it. Hold it.”
Five seconds later, Mandy finally let go of Andrew’s head. He jerked back, saliva pouring from his mouth, his chest heaving up and down as his lungs searched for air. Tears were leaking out of his eyes.
“Pretty good job for your first time,” she said, smirking at him. “Did you enjoy deepthroating my cock?”
“Yes mistress,” Andrew croaked.
“That’s what I like to hear,” she replied. “Now onto the next stage. Get your ass up here on the couch.”
Andrew climbed up next to her.
“On your back with your head over there,” Mandy said, pointing towards the armrest.
Andrew got himself into position, his back on the couch, his legs spread wide and his cock standing straight up in the air.
“Good boy,” Mandy said, scooting in closer to him, until her body was situated between his legs. Her cock was touching his and her hips were underneath his thighs.
“First I’m going to get you warmed up,” Mandy said. She reached over to the end table and grabbed a bottle of lube of squirted some of it on her finger. “I don’t want to break you in half, at least, not in the beginning,” she said.
“Thank you, mistress,” Andrew said.
After she’d coated her finger with the lube, Mandy rubbed the outside of his anus with the tip of her finger.
Andrew moaned softly.
“You like that, do you?” Mandy asked.
“Very much, mistress,” he replied.
“Well, let’s see how you like this,” she said, suddenly jamming the tip of her finger inside his asshole.
Andrew let out a low gasp and gritted his teeth.
“Not so much, huh?” Mandy said.
Andrew just shook his head but she let it slide.
“Don’t worry,” she said. “Your asshole will loosen up real quick.”
And it did, along with some help from her finger. She slid it in and out of Andrew’s anus for a bit, then held it halfway inside him and wiggled it around, getting him loosened up.
“Are you ready for another one?” she asked.
“Yes, mistress,” Andrew said.
Smiling, she slid another finger inside him. Again he gasped and flinched, but just like before, after a little bit of working it, he was able to take both fingers inside his asshole without too much discomfort.
“I think you’re ready for the real thing,” Mandy said after a full minute of working his asshole with her fingers. “What about you, big boy? Do you think you’re ready to take my cock in your ass?”
“As ready as I’ll ever be,” Andrew said.
Mandy tilted her head slightly and giving him an admonishing look. “You don’t sound too enthusiastic about it,” she said. “I don’t think I like that.”
“Sorry, mistress,” Andrew said. Then, in a more upbeat tone, he said, “I can’t wait to have your cock in my asshole.”
“That’s better,” Mandy said, looking down at his wide open legs and tight little asshole.
She grabbed the bottle of lube from the end table and squirted it all over her cock. Then she worked it in with her hand, jerking herself off as Andrew looked on.
“All right, big boy,” Mandy said. Holding her cock tight, she moved her hips towards Andrew until the tip was just barely touching his asshole. “Here comes the moment of truth.”
Mandy pushed forward, inserting the tip of her cock into Andrew’s anus. He let out a gasp and followed that with a long, slow exhalation of breath. Smiling widely, Mandy looked down at him, getting off on the discomfort playing upon his face.
“Don’t push me out,” she said. “Don’t push my cock out of your ass. Keep it right fucking there, understand?”
“Yes mistress,” Andrew managed to say.
“It’s not so easy, is it?” Mandy said. “It’s no piece of cake taking a dick in your ass, is it?”
“No mistress,” Andrew said through gritted teeth.
“Don’t worry,” Mandy said. “Just relax. It’ll get easier soon enough.”
She worked her
hips slowly, giving him no more than a quarter of the dildo per pump. But still, Andrew seemed to be struggling with it, so Mandy decided to help him out a bit by playing with his cock while she fucked his ass. After all, if he couldn’t get past this first part of the session, she’d have no opportunity to give it to him like she wanted to. And that was no good.
Playing with Andrew’s cock seemed to relax him, and it wasn’t long before his asshole was loosened up enough that Mandy was able to give him half of her cock at a time before pulling back.
“There we go,” she said. “That’s better.”
Andrew was more into it too, barely even grimacing as Mandy pumped his asshole with her cock. Which meant that she had to turn the heat up. She didn’t want him getting too comfortable . . .
“Grab ahold of your cock,” Mandy said. “Jerk yourself off while I fuck your ass.”
As Andrew started playing with himself, Mandy reached underneath his legs and lifted them up and back, exposing more of his asshole to her and giving her better leverage.
“Open up for me,” she said. “Open your legs wider.”
Andrew did as he was told.
“Now hook your arm under your knee,” Mandy said.
Andrew did this too.
“That’s better,” she said, pausing for a moment but leaving her cock planted halfway in his ass. “Now I can fuck your ass like it deserves to be fucked. Do you like that idea?”
“Yes, mistress,” Andrew said.
Mandy rose up on her legs a little bit higher, altering the angle of penetration and allowing her to get her whole cock into his ass more easily.
“Are you ready to take all of my cock in your ass?” she asked.
Andrew only nodded but Mandy didn’t care. She didn’t even really need a response from him at all, she was just messing with him.
“Good, because shit’s about to get real right now.”
And with that, she forced the entire dildo into Andrew’s ass, giving it to him balls-deep (metaphorically, of course) and holding it there.
24 Aggressive & Filthy Stories 2 Page 12