30 Depraved & Wicked Stories 2

by Heather Monroe

After a few more thrusts he’s had enough of her doing the work. It’s time to take control. Tim brings his other leg up onto the couch to give him more leverage and grabs ahold of Tracy’s hips and starts slamming his cock into her, pummeling her ass like a wildman.

  “Just like that, just like that,” Tracy says, the words coming out in a breathless rush. “Stretch that tight fucking ass out. Yes, yes, yes!”

  His hands slide up her back to her shoulders and press down on them.

  Tracy gets the hint, relaxing her arms and dropping her head down to the couch. She turns her head so half of her face is lying flat on the cushion while the other is turned to the side, watching him fuck her ass in the reflection of the mirror.

  Tim’s legs are starting to tighten up so he scoots his feet further forwards, changing the angle and giving him even more leverage. Squatting over Tracy now, he hammers away at her ass, pounding her with everything he has.

  Tracy runs her arms backwards and grabs ahold of her asscheeks and spreads them wide, stretching her ass, opening her asshole up even further.

  “Ohmygod,” she screams as Tim fucks her. “You’re gonna make me fucking cum! FUCKFUCKFUCK!”

  Tracy’s body shakes and shimmies beneath him, her head moving back and forth, her hair flying everywhere. She lets out a wordless groan and then her body bucks a couple of times and then falls still, her breath coming in ragged bursts.

  Taking mercy on her, Tim slides his cock out of her ass, climbs off her and sits down on the couch, giving Tracy a moment to catch her breath.

  “Holy shit,” she says, rolling over until she’s sitting normally on the couch next to him. Her breathing is still deep and ragged but almost under control. “That was fucking incredible.”

  “What’s that? Orgasm number four for you?” he says, looking over at her with a little smirk.

  “Five, actually,” she says.

  He shakes his head. “That is so unfair.”

  “Like I said before, that’s life.”

  “Tell me about it,” Tim says, his voice filled with outrage that was only partially fake. “Five orgasms for you already and not a single one for me. And to top everything off, I’m the one paying.”

  Tracy’s smile grows wider. “Yeah, that sucks for you.”

  “Hell, you should be paying me.”

  She laughs and shakes her head dismissively.

  “What’s so funny?”

  “Nothing,” Tracy says, sliding towards him. “You’re right, that’s all. You should be getting paid for your talents.”

  “Tell me about it.”

  “Not by me, of course,” she says.

  “What? Why not?”

  Tracy grabs ahold of Tim’s still rock-hard cock and starts jerking him off. “Because,” she says, “Why you should I pay you to fuck me when you pay me to fuck me?”

  “Because you get five orgasms to my one,” Tim says.

  “Yes, but that’s only because I’m so good at my job,” Tracy says, leaning over and licking the tip of his cock. “If I wanted to, I could make you cum within minutes, and then what would we do for the rest of the hour? Talk?”

  “You couldn’t make me cum within minutes,” he says.

  Tracy looks at him like she can’t believe he just said that. “Please,” she says. “I can make you cum whenever I want to. It’s only because I want you to feel like you get your money’s worth that I wait until the end of the hour.”

  “Bullshit,” Tim says.

  “Fine,” she says. “Want to bet on it?”

  “Sure. How much?”

  “If you win, I’ll give you a freebie next time.”

  “And if you win?” Tim asks.

  “You pay me double for tonight.”

  “How long do I have to hold out?” he asks.

  “Five minutes,” she replies.

  “Two,” he counters.

  “Three,” Tracy says. “Three minutes without blowing your load and you win the bet.”

  “Done,” Tim says, grabbing for his phone on the end table near the couch.

  “But you can’t pull away,” Tracy adds. “You have to let me do whatever I want to you. Any funny business and you forfeit.”

  “Fair enough,” he says, cycling through the menu on his phone until he comes to the stopwatch app.

  “Shall we shake on it?” Tracy says.

  “Sure.”

  They shake hands.

  “When do we start?” Tim says, his finger over the button that starts the stopwatch.

  “Now ,” Tracy replies, dropping down to the floor, and spreading his legs wide before he has a chance to start the clock.

  He presses the button and drops the phone on the couch by his side just as she swallows his cock whole, deepthroating him with ease.

  Tracy holds his cock in her throat for full ten seconds, maintaining eye contact the whole time, before letting it slowly slip out, inch by inch. Once it’s free she starts attacking it immediately, moving her mouth rapidly up and down on it while her hand works his shaft right below her lips and her other hand works his balls, squeezing and caressing them. His cock is slippery as hell from all the saliva she’s generating, allowing her hand to work his shaft feverishly while still maintaining an insane level of pressure.

  Watching Tracy work is just making it that much harder to maintain control so Tim pulls his eyes away and looks around the room, trying to distract himself. But nothing’s working. What she’s doing simply feels too good.

  Tim glances down at his phone and sees that only 20 seconds have passed. He chuckles under his breath and shakes his head. He has absolutely no chance of lasting 3 minutes without blowing his load. He’ll be lucky if he makes it to the 1 minute mark.

  Fuck it, he thinks to himself. No reason to fight it. Might as well sit back and enjoy the ride.

  He turns his attention back to Tracy just as she pulls her lips off his cock and takes his balls in her mouth, sucking and slurping them intensely while still working his cock with her free hand.

  She takes both balls in her mouth at the same time and pulls down on his sack, pushing the envelope between pleasure and pain but bringing him ever closer to orgasm.

  Tim tries to not make any noise, hoping to fool her into thinking he’s still far away from cumming but he can’t help himself. A brief gasp escapes his throat and she looks up at the sound.

  Catching his eye, Tracy gives him a knowing little wink, then goes back to work, pushing on the back of his legs, lifting them up, rolling him back in the couch, giving her a better angle to work with.

  And—he quickly learns—giving her easier access to his asshole.

  With his underside more exposed, Tracy goes to work on his taint, licking and rubbing it with one hand while she works his cock more slowly with her other one.

  She quickly makes her way down to his asshole proper, exploring the outside of it for a few seconds before licking it, then sucking it, then sticking her rigid tongue inside it and bouncing her face against his ass, forcing her tongue deeper and deeper and deeper inside his asshole while continuing to jerk him off.

  Tim’s been desperately holding on for the last 15 seconds and riding the edge of orgasm for the last 5 but he simply can’t hold out any longer.

  “Fuckingshitgodammitmotherfucker,” he says in a breathless rush as his body tenses up like it never has before.

  Smiling like a demon, Tracy lays off his asshole but continues jerking him off as Tim’s body bucks beneath him. She pulls back slightly on his cock as he cums, pointing it at her face as the white ribbons of sperm shoot out of his cock with a force unlike ever before, spraying her face and hair and over her head and flying into her open mouth.

  Tim bucks again, and again, and again, each time sending an ever-decreasing spray of cum onto Tracy’s smiling face.

  “Holy shit that’s a big load,” she says, laughing under her breath.

  “Tell me about it,” Tim says.

  Once he’s finally done she licks his co
ck clean before finally releasing it.

  “Did you even make it halfway?” she asks.

  He looks at his phone. It has just passed the 2 minute mark. He presses the button, stopping the clock.

  “It was probably close,” he says. “But I doubt it.”

  “I tried to tell you.”

  “You sure did,” Tim says. “I should have listened.”

  He walks over to the other side of the room, grabs his wallet out of the desk, and pulls 5 one-hundred dollar bills from it.

  “Here you go,” he says, handing her the money. “Another five hundred in cash on top of the five that went on my card.”

  Tracy drops the money in her purse and heads towards the bathroom to get cleaned up. “It was a pleasure doing business with you,” she says.

  “I wish I could say the same,” he says under his breath as she closes the bathroom door behind her.

  But he doesn’t mean it. The way he figures it, even at a grand an hour Tracy is well worth the money. Hell, he’d pay more for her if he had to.

  Hopefully I never have to, he thinks to himself.

  He flops down on the couch and takes a deep, exhausted breath, already looking forward to their next session.

  #####

  DEPRAVED & WICKED: VOLUME 34

  I was sitting at the end of the bar, minding my own business and enjoying the scenery, when I caught a glimpse of a woman who was vastly different from the rest of the skinny, emaciated girls that seemed to populate the bars out here in SoCal. 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 Gianna,” the bartender said. Apparently her name was Gianna. And from the way her and the bartender were interacting, she was obviously a regular.

  “Hey Frank,” Gianna 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,” Gianna 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 Gianna 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,” Gianna 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?” Gianna 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,” Gianna 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,” Gianna 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,” Gianna 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?” Gianna 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,” Gianna 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, Gianna 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 Gianna 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,” Gianna 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,” G
ianna said.

  “It does indeed.”

  Gianna 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 arrived at Gianna’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.

  Gianna 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 Gianna 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,” Gianna 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.