by Evan Harder
“It sure has,” Hailey replied. “Rock fucking hard the whole time I’ve been debasing you. Quite the feat, actually. You must really like this shit.”
“Even more than I’d realized,” Greg said.
“Well, it’s time to finish you off then,” Hailey replied. “After I have my fun first, of course.”
“Of course,” Greg said. “I wouldn’t have it any other way. Not that I have a choice in the matter,” he added.
Hailey smiled and ordered him to turn around so he was facing her. “On your back though,” she said. “I want to look into your pretty eyes as I fuck your ass raw.”
Greg laughed softly. “You’re one hell of a unique woman, you know that?”
“One of a kind, indeed,” she agreed, smiling at him. “Now do what you’re told, slave. I’m ready to burst from all this fun and I know that you are too.”
“Yes, mistress,” Greg said, flipping onto his back and turning around and spreading his legs wide.
“There you go,” Hailey said, grabbing him beneath the thighs and lifting them up, raising his ass off the bed and giving herself a better angle to attack his asshole. “Time to fuck your ass until we both cum.”
“Sounds like a plan.”
With the dildo still slick from Greg’s saliva, Hailey proceeded to slip it into his asshole, giving him just the tip at first but continually pumping her hips forward and back, giving him more and more of the cock with each thrust.
As the dildo went deeper and deeper, Greg’s sensations intensified. It wasn’t long before he was back to grunting and groaning with every thrust, although more loudly now that the ball-gag was no longer muffling the sounds.
“Tell me how much you like it when I fuck you ass,” Hailey said, grinning down at him like the devil.
“I love it,” Greg groaned. “I fucking love it.”
“Even when I do this?” Hailey said, slamming her hips forward, driving the dildo into his anus until it completely disappeared and holding it there.
“Yes,” Greg said after grunting loudly. “Even when you do that.”
“You’re such a good little boy,” Hailey said, laughing softly before letting her cock slip almost completely out of his asshole. “Now I want you to do me a favor,” she said.
“Anything,” Greg replied.
“Hold your legs up for me,” she said. “I want my hands free to do a few things.”
“My pleasure,” he said in a forced voice that sounded like it didn’t hold much pleasure at all. But his cock was still rock-hard, which proved he was enjoying himself, on some level, at least. He hooked his arms beneath his knees and held them aloft.
With her hands now free, Hailey went to work with them. While fucking Greg’s ass with long, slow strokes, she started playing with her pussy, rubbing her clit with one hand while sliding three fingers into her pussy with the other.
As she ramped up the intensity in which she fucked Greg, she also turned up the heat on herself, banging away at her pussy with her fingers while she slammed his asshole with the dildo.
After almost a full minute of pummeling him harder than any other time all night while simultaneously working her pussy with reckless abandon, Hailey was ready to cum.
“Holy fucking shit I’m gonna fucking cum,” she said, still working his ass and her pussy with a frenzied intensity. “Are you ready to taste me?” she asked.
Greg just nodded. He couldn’t have spoken right now under any circumstances.
“Fuck, fuck, fuck!” Hailey cried as she yanked her hand out of her pussy but kept rubbing away at her snatch while fucking Greg. “Here I cum, baby, here I fucking cum!”
The words had barely left her mouth when a jet stream of her juices flew out of her pussy, drenching Greg’s abdomen, chest and his face as Hailey squirted all over him.
Her pussy was like a firehouse, spraying juices everywhere and with serious velocity as Hailey screamed in pleasure and continued banging away at her clit until her well finally ran dry after nearly five seconds of squirting. The dildo was still planted deep in Greg’s ass but she was no longer pumping away.
“My god that was fucking intense,” she said, laughing as she stared down triumphantly at Greg. “And now that it’s out of the way, I can finish you off too. Would you like that?”
Greg nodded, taking a moment to catch his breath as Hailey recovered from her orgasm.
“I want to hear you say it,” she told him. “Tell me exactly what you want me to do to you.”
“I want you to make me cum while you’re fucking my ass,” Greg replied.
“How do you ask?” Hailey said.
“Please.”
“Ask again, and this time make it sound like you mean it,” she said.
“Please make me cum while you’re fucking my ass,” Greg said, begging now. “I want it. I need it. Please, mistress. Please.”
“If you insist,” Hailey said, smiling wickedly.
And with that she began to move her hips once again, pushing forward and back, forcing her cock deeper and deeper into Greg’s asshole as she turned up the intensity, until she was slamming away at him, giving him the entire dildo with each thrust, pummeling his anus as hard and fast as she could.
Greg was grunting and groaning continually now, his asshole raw and his cock as hard as a steel rod.
“Are you ready?” Hailey asked, staring down at him while she continued destroying his asshole. “Are you ready for me to finish you off?”
Greg nodded like crazy.
“What?” she said, grinning at him deviously. She was thoroughly enjoying herself. “I can’t hear you.”
“Yes,” Greg managed to say between gritted teeth. “Yes please.”
“Are you sure?” Hailey asked.
“Yes,” Greg said. “I need it. Please give it to me, I need it so bad.”
“Oh, fine,” Hailey said, reaching down and grabbing ahold of his raging cock in her hand. “I guess you deserve it.”
Hailey continued hammering away at Greg’s asshole while she jerked him off, not wasting any time by taking it slow. She gripped his cock tight and let her hand fly, moving it up and down his shaft so fast it was a blur.
As wound up as Greg already was, it didn’t take long at all until he was right on the edge of cumming. He was too exhausted to say anything, but Hailey could see it on his face, and ramped up the intensity just a bit more in return.
Greg let out a low, deep moan and then released, sending his seed shooting out of the tip of his cock, which Hailey had cleverly aimed directly at his head.
And so Greg came all over of himself while Hailey grinned widely and hooted and hollered and continued fucking his ass. It was a monstrous load, the biggest he’d ever shot in his life by far, and it just continued pumping out, spraying him in the chest, the neck and the face, some of it even getting in his own mouth.
His entire body above the waist was covered in his and Hailey’s juices but he was too spent to care. He’d never been the exhausted in his life.
Once Hailey had jerked Greg off to completion, she finally let the dildo slip out of his asshole and climbed up on the bed next to him. She propped her head up on her arm and gloated over him with joy.
“Well, what did you think?” she asked.
“I think that was fucking incredible,” Greg replied, still trying to recover. “But I have to admit, I’m glad it’s over.”
“Fair enough,” Hailey said. “But the real question is: would you do it again?”
“In a heartbeat,” Greg said. Then, thinking better of it, he smiled and added, “Although I might have to let my asshole heal for a day or two.”
Hailey laughed. “I hear you there. And I might have a solution for you.”
“What’s that?” he asked.
“Well, maybe while your asshole it recovering, I’ll let you do to me what I just did to you.”
“You’d do that?”
“Fuck yeah,” Hailey replied. “After all, I follow the g
olden rule. Don’t do to others what you won’t let them do to you. Or something like that.”
“Close enough,” Greg said. “So what do you say? Tomorrow night?”
“Same time, same place,” Hailey said. “Minus the bar, of course. Just bring a few bottles of red wine over here and we’ll get drunk and do it all over again.”
“Except we switch places,” Greg reminded her.
“Of course,” she said. “As long as you promise me one thing.”
“What’s that?”
“That you fuck my ass as hard as I fucked yours tonight.”
“Oh, you don’t have to worry about that,” Greg said. “I’m going to give you a reaming you won’t forget.”
“I sure hope so, my friend. I sure hope so.”
#####
GETTING OWNED BY THE FREAKY BABE
I was minding my own business at the end of the bar, enjoying the scenery and my beer when I caught a glimpse of a woman who was completely different from the rest of the skinny, emaciated girls that populated the bars out here in Southern California. She was standing by herself, leaning against the bar on the other side of the room, checking things out, just like I was. And true to form, mere milliseconds after I spotted her, she turned towards me as if sensing my interest.
We locked eyes and stared at each other as our brains went through the millions of instantaneous, unconscious determinations that would decide our level of attraction for each other.
It took less than a second for my brain to come to inform me that I was, indeed, incredibly attracted to her. And she must have come to the same realization, as before I could even think about what my next move should be, she started walking across the bar towards me.
As she approached, I observed her in a more clinical, rational way, taking in her entire body at once, then piece by piece, and putting it all together.
She was a very tall woman—practically the same height as me even without heels—and built like a brick shithouse. She wasn’t fat but she wasn’t skinny either. She had some meat on her, from her midsection to her hips to her bubbly ass to her long, powerful, figure-skater legs.
As she came closer I got a better look at her face. She had prominent features; big, brown eyes, a good-sized nose, full lips and long blonde hair. Her makeup was subtle, accentuating her features but not drowning them, making her look more like an old-school pin-up star than a modern slut.
Then there were her tits. They were the first thing I noticed but I’d deliberately skipped over them so I could come back to them at the end and let my gaze linger. They were huge: the size of my head if not bigger. Absolutely incredible. And while it was too early to tell if they were natural, I didn’t really give a shit. The way I figured it, if I could touch them and play with them and suck on them, that was good enough for me.
It wasn’t until she sat down next to me that I realized she was a bit older. Early-thirties, probably. Not old by any stretch of the imagination, but older than me by a good seven or eight years. But that was okay, I didn’t have a problem with older women. In fact, I’d always dreamed of being with one.
“How’s it going?” she said after sitting down, taking charge of the situation right away, which was no surprise to me. That was one of the things I’d noticed immediately; she appeared to be the kind of woman who wasn’t afraid to take the lead.
“Not bad,” I replied.
“You want another beer?” she asked, gesturing towards my nearly empty glass.
“Sure,” I said.
She whistled down to the bartender and I came over immediately.
“Hey Angelica,” the bartender said. Apparently her name was Angelica. And from the way her and the bartender were interacting, she was obviously a regular.
“Hey Frank,” Angelica replied. “Two beers. A Killian’s for me, and—” She turned her head towards me.
“A Killian’s for me too,” I said.
“Just put it on my tab,” Angelica said to Frank.
“You got it,” Frank replied. He disappeared then reappeared ten seconds later with the two beers. He set one in front of Angelica and one in front of me then disappeared once again.
“Thanks for the beer,” I said, taking a sip from the chilled glass.
“No problem,” Angelica replied.
“I have to ask, though: What prompted this little palaver.”
“Well, I saw you looking over at me and decided to see if it was just casual or if you had something else in mind,” she replied.
“And what does your gut tell you?” I asked.
“If I thought it was just casual I wouldn’t have come over,” she said.
I laughed and we both took another drink of our beers.
“Was I correct in my assumption?” Angelica asked once she’d set her drink down.
“You were indeed,” I said. “I must confess to having more than just a casual interest in you.”
“That’s good to hear,” she said. “Because I feel the same way about you.”
A little tingle went down my spine and I tried unsuccessfully not to smile.
“But I have to warn you,” Angelica said. “You may want to think a little more carefully before you commit to anything.”
“Oh yeah?” I said, suddenly cautious. “And why is that?”
“Because I’m a bit of a control freak,” she said. “I like to be in charge, to take the lead and run the show, doing whatever I want along the way.”
I let out a relieved little laugh. “That’s it? I thought you were going to say you were really a man or something.”
“Nope,” Angelica said. “I just like to get that part out of the way up front. Most men don’t deal with it very well.”
“Actually, I don’t mind that sort of thing. I kind of enjoy it, to be perfectly honest.”
“Yeah, I kind of figured that about you,” Angelica said. “You look like you’re not afraid to get a little freaky in the sack.”
“Is that right?”
“Yep,” she said. “That’s why I headed over here in the first place. I’m an expert at reading people. Of course, just because I could tell you were into that sort of thing doesn’t mean that you can actually handle a night with me.”
I laughed softly.
“You think differently?” Angelica asked.
“Let’s just say I haven’t come across much that I can’t handle,” I said.
“Is that right?”
I nodded.
“Fair enough,” Angelica said, a knowing little smirk worming onto her face. “But I have to warn you, most of the men I approach like this same the same thing. They all think they can handle me. Every single one of them. But it’s rare I find one that actually can without complaint. Especially with what I dish out.”
“It’s that intense, huh?”
Smiling, Angelica nodded vigorously.
I smiled back. “Then it sounds like it would be fun.”
“So you’re game?”
“Absolutely,” I said. “On one condition.”
The look Angelica shot me was more intrigued than skeptical. “What’s that?”
“If I can handle whatever you can dish out tonight, then I earn another night with you. Where we find out if you can handle what I can dish out.”
“Sounds fair enough to me,” Angelica said.
“So you like to receive as much as you like to give?” I asked.
“Not as much,” she said, smiling. “But pretty close.”
“Same here,” I said.
“Then it appears we have come to an agreement,” Angelica said.
“It does indeed.”
Angelica pounded the rest of her beer and rose to her feet. “Do you mind if we go to my place? It’s just a couple blocks away.”
I too finished my beer and set the glass down. “No problem at all.”
She grabbed my hand and gruffly pulled me off the stool. “Then let’s go.”
###
Five minutes later we arri
ved at Angelica’s place. She unlocked the door and held it open for me. I walked in, stopped just inside, and looked around. It was a nice place, if a little plain. Comfortable but more functional than anything else.
Angelica closed the door behind us. I turned around to face her and found that she was already on her knees, right there in the hallway, looking up at me with focused intent.
“Oh,” I said as she reached out and started undoing my belt. “Okay then.” I knew she’d said she liked being in charge, but this wasn’t quite what I was expecting. Not that I minded.
It took her less than five seconds to have my belt unbuckled, my zipper down, my button undone and my pants and boxers down around my ankles. My cock was sticking straight out, already fully hard. It wasn’t enormous but it was pretty good sized; most girls found it to be a little too big for their tastes but I didn’t think Angelica would have that issue.
“It’s hard already, huh?” she said, staring right at it, obviously impressed.
“It always is,” I replied.
“Always?”
“Pretty much.”
“Well, that certainly makes things easy,” Angelica said. “And it’s just the right size too.”
“It isn’t too big for you?” I said, mostly just taunting her.
She scoffed. “Please.”
“Yeah, I kind of thought you’d be able to handle it,” I said.
“With ease,” she replied. And with that, she immediately went to work on it, licking up and down the shaft, one hand grasping the base in a death-grip while the other worked my balls. She popped the tip of my cock in her mouth and sucked on it while jerking me off, her hand and mouth working in tandem as her mouth dropped further and further down my cock, her head bobbing up and down, faster and faster, her hair flying everywhere, covering her face, blocking my view.
I grabbed a handful of her hair and pulled it back so I could get a better view of what was happening.
“You like to see what’s going on, do you?” Angelica said, popping my cock out of her mouth for a moment.
I nodded.
“That’s good,” she continued, jerking me off all the while. “Because I do too. Bright and clear, everything out in the open, no shame whatsoever.”