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 continued 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.
&nb
sp; 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.
#####
TOP SHELF COUGAR
COUGAR TALES: VOLUME THREE
SCOTTY DIGGLER
Billy Jackson was embarrassed. He didn’t know what to do. A couple hours ago he’d called a number given to him by a friend, and now, at eight o’clock in the evening, he was standing in a hotel room next to a gorgeous cougar wearing high heels and a little purple dress that left very little to the imagination.
She’d said her name was Sandra and she was a tall, stunning brunette with an incredible body; rock hard from head to toe, tan skin, long, shapely legs, toned arms, and enormous tits.
Sandra was a little older than Billy had been expecting, probably in her early-thirties, a good 8-10 years older than him. Not that he minded. In fact, an older woman was exactly what he needed right now. Someone to take charge, to show him the ropes. That was what this whole night was about anyhow.
“Is this the first time you’ve done something like this?” Sandra asked.
Billy nodded. Then he realized that she might not have been asking what he’d thought she was. “Not my first time having sex,” he added hastily, “Just my first time with a—”
“Escort?” Sandra asked.
“Yeah,” he replied.
“And that makes you uncomfortable?”
“A little bit.”
“It’s not that big of a deal,” she said. “Just pretend like you picked me up in a bar or something. You’ve done that before, right?”
“Not exactly,” he said.
“What about a party or a concert, something like that? Have you ever gone home with a woman after a night on the town?”
Billy shook his head.
Sandra offered him a little smile laced with pity. “How many times have you had sex?”
He shrugged. “Fifteen, twenty times maybe. Something like that.”
“Let me guess,” Sandra said. “All with the same girl?”
“Yeah.”
“Your girlfriend, I assume?”
“My ex-girlfriend,” Billy said.
“Gotcha,” Sandra said. “And what kind of sex are we talking about here?”
“Just the basics,” he said.
“What does that mean to you exactly? I’m guessing your idea of the basics is far different from mine.”
Billy shrugged again. “I don’t know. Missionary, mostly,” he said, his tone reflecting his discomfort at talking openly about his sex life, or lack thereof.
“What about blow jobs?” Sandra asked.
“Not really,” he said, blushing just a hair. “Once or twice, and only for a short time. Thirty seconds each, maybe.”
“Did you give you hand jobs? Jerk you off?”
“Sometimes,” Billy said.
“Did you ever give her anal sex?”
His face turned bright red from embarrassment. “No. She said didn’t like it.”
“What about your fingers?” Sandra asked. “Did you ever use them on her? Play with her pussy, rub her clit, anything like that?”
“A few times,” he said. “Just to get her warmed up.”
Sandra laughed under her breath and shook her head.
“What?” Billy said.
“Nothing,” she replied. “I just feel bad for you, that’s all.”
“Why?”
“Because your girlfriend was such a prude,” Sandra said. “Okay, so a few more questions and then we can get started.”
“Okay,” Billy said.
“What about porn?” she asked.
“What about it?”
“Do you ever watch it?”
Billy shrugged. “Occasionally,” he said, his embarrassment growing even further. He looked down at the floor, unable to meet her eyes.
“Hardcore stuff?” Sandra asked.
His eyes flashed up in annoyance. “What difference does it make?”
“I’m just trying to get a feel for how much you know, what you’re aware of, so I don’t make you uncomfortable,” she said. “I want you to have a good time, you know. That’s kind of my job description.”
“Assume I don’t know anything at all,” he said. “Because I feel like I don’t.”
“Fair enough,” Sandra said. She took a couple steps towards Billy until she was standing right in front of him, their bodies practically touching. “So here’s what we’ll do. Imagine that ten minutes ago, we were at a bar. You were standing there, having a drink, when I came up to you.”
Her voice changed, grew infinitely more sexy, soft and throaty. She leaned forward and whispered in his ear: “You’re fucking gorgeous. I’d love to take you back to my hotel room and ravish you.”
Billy took a deep breath. He tried to swallow but his throat was suddenly dry. He knew Sandra was just playing a role, but she was so convincing that it didn’t matter. Even though he knew better, on some level he thought her words actually reflected her feelings.
“Just follow my lead,” Sandra said, still whispering seductively, her tone dripping need and desire. “I’ll take care of you, big boy. I’ll take you places you’ve never been before.”
“Okay,” Billy managed to squeak out, his entire body tingling with excitement as she took his hand and led him to the couch.
Once they reached the couch, Sandra turned Billy around so his back was towards it, then give him a little push, dropping him onto the cushions. She spread his legs apart, stepped in between them, and pulled her dress over her head, revealing her huge, natural breasts in all their glory. The only thing left on her body was her black g-string and 3-inch fuck-me pumps.
Billy took a deep breath and let it out slowly, trying to calm himself. His cock was hard just from looking at her. It was pressing up against his jeans painfully.
Looking down at him, her face deadly serious, Sandra grab ahold of her tits and started groping herself, rubbing her nipples and squeezing them to get them hard. She cupped her hand beneath one of her tits and brought it up towards her mouth and started sucking on the nipple.<
br />
“Do you like these tits?” Sandra said.
Billy nodded. There was no way he could talk right now.
“Do you want to taste them?”
Billy nodded again.
Sandra climbed onto the couch, straddling Billy’s groin. He sucked in his breath quickly and bit down on his bottom lip. Just the pressure of her ass on his dick was almost enough to make him cum.
“A little bit jumpy, huh?” Sandra said.
“Yeah,” Billy said softly, barely more than a whisper.
“That’s okay. When you’re ready to cum just let it go. It doesn’t matter how soon.”
“Are you sure?”
“Positive,” Sandra said. “There’s nothing wrong with expending one bullet early. In fact, it’s a good thing.”
“How can that possibly be a good thing?” Billy asked.
“Because it takes a lot of pressure off,” she replied. “Which makes it easier to last longer the second time around.”
“There’s going to be a second time?”
“There’s going to be as many as you can handle,” Sandra said. “You paid for a full hour and that’s what you’re going to get. You can cum as many times as you want.”
“Really?” Billy said.
“Really,” she said. “Now let’s get on with it. We’re wasting time here.”
Sandra leaned forward and stuck her tits in Billy’s face. She shook her chest from side to side, bouncing her tits off his head a few times before guiding one of her nipples into his mouth.
Billy sucked on Sandra’s hard nipple like a baby while she slowly moved her ass back and forth, grinding on his cock, which was still trapped beneath his jeans but pressing hard against the denim.
Sandra switched things up, giving Billy her other nipple and grinding on his cock more forcefully. His breath rate increased immediately, as did the force in which he went after Sandra’s nipple.
Despite Sandra telling him not to worry about how long he lasted before cumming, Billy was holding on as best he could. He was just too used to being done after his first orgasm.
But Sandra was having none of it. She could sense how far along Billy was and was determined to finish him off. She pulled her nipple from between his lips, then leaned in and stuck her tongue in his mouth and started to explore.
Rough & Aggressive - 4 Tales Of Extreme Filth Page 5
