I was desperate to have his cock inside me by now, so I quickly adjusted my position so my knees were bent and my shins were flat on the cushion underneath my thighs, then I grabbed ahold of his cock and slipped it into my soaking wet pussy.
We both let out soft but insistent groans as he entered me.
Scott was so big that it was a tight fit but I was wet enough that it wasn’t an issue. Just a little bit of pressure in all the right places as my pussy engulfed his cock.
I placed my palms on top of Scott’s thighs and leaned back, arching my back and tilting my chin towards the ceiling, exposing the hollow of my neck and offering him my still-clothed chest.
He took the bait, grabbing and squeezing them through the material of my shirt, then cupping his hands beneath them and pushing up while I bounced atop him, my hair flying everywhere as wet, slapping sounds filled the room as our bodies came together.
I hammered down on his cock a few more times before suddenly leaning forward, mixing things up a bit, changing the angle of penetration.
At this point in the evening, I was looking to do some damage, so I put my hands on Scott’s chest for balance and started bouncing atop him, impaling myself on his cock, hammering my body down onto his. I rode his cock from tip to base, slamming my ass down, taking the entire thing in fast, rhythmic thrusts.
“Do you like that?” I asked, whispering harshly between deep breaths. Our faces were inches apart, close enough that I could feel his hot breath in my face. It smelled like cinnamon and grapes. “Do you like it when I ride your cock?”
“I love it,” Scott said.
“Yeah?” I asked, taking a moment to slip my shirt off and then my bra, freeing up my tits. They were big and beautiful, not gigantic but perky and awesome and completely natural.
He nodded, his eyes locked onto my newly released puppies.
“What about my tits?” I asked, climbing a little bit higher atop him so my chest was in his face, mere centimeters away, close enough that my hard nipples brushed his lips every once in a while.
“I love them too,” he said, his trademarked sly little grin still on his face.
“Do you want to lick them?” I asked, still moving up and down on his cock, just not with as much force.
“Very much so,” he replied.
“Yeah, I thought you might,” I said, keeping his cock inside of me but no longer bouncing on him. “But first I want to do something to you.”
“Whatever you want,” Scott said.
Smiling, I grabbed the back of his head and pulled it forward, pressing his face into my chest, smothering him against my flesh. Then I squeezed my tits together, smashing his head between them and pulling his face further against my chest while I stayed put atop of him. His cock was pressing against my vaginal walls and I could feel it getting harder as I smothered him with my tits.
I held him in place for a full ten seconds before letting him free. Breathing deeply, he smiled up at me, his face red and his eyes full of excitement.
“It looks like you enjoyed that,” I said.
“It was awesome,” he replied.
“Do you want me to do it again?”
“Yes please,” Scott said.
So, after giving him another couple of seconds to catch his breath, I grabbed the back of his head and again pulled his face against my chest, smothering him. This time I upped the ante by starting to slowly ride his cock once again.
This time, after a full 15 seconds of holding him there, I could feel him starting to get a little antsy. He still hadn’t tried to pull away, but I could sense it was imminent. But I wanted to see how much he could take. Plus I knew at least part of him liked what was going on; his cock was bigger than ever inside me. So instead of releasing him, I leaned forward and put my mouth next to his ear.
“Just relax,” I whispered. “You’re a real man. You can handle it.”
He relaxed his body and calmed down considerably.
“There you go,” I said, stroking his hair with my fingers. “Don’t worry, I’ll let you up before anything bad happens.”
I could feel his hot breath against my skin as he struggled for air but still I held him tight. He wasn’t in any danger. And having control over him was turning me on like crazy.
When I finally let him free after almost half a minute, Scott’s face was bright red from exertion and he was gasping for breath, but his smile was wider than ever, and his cock his bigger than every before.
“That was incredible,” he said.
“Yeah, I could tell that you liked it,” I replied.
“And I’m guessing you did too,” Scott said.
“Oh yes,” I said. “It was awesome. But now I need for you to suck on my nipples.”
“With pleasure,” Scott said, pushing his head towards my tits.
I leaned forward until my hard nipple was touching his lips. He took it in his mouth and sucked on it.
“That’s a good boy,” I said. “Suck on those fucking titties. Don’t be shy. Get nasty with it. I can take it.”
So he did, flicking the nipple with his tongue, even biting down on it with his teeth, making me gasp in surprise and excitement.
“There you go,” I said as he worked one nipple until it was rock-hard before moving on to the other one while I gradually picked up the speed in which I was bouncing atop his cock. “That’s what I’m talking about.”
Scott gave my other nipple the same treatment. Once it was feeling as stimulated as the other I grabbed ahold of his hair and yanked back on his head, popping my nipple from his mouth.
Turned on immensely now, I slipped my tongue into Scott’s mouth and explored his tonsils with serious intensity while riding his cock like an insane cowgirl. His hands had made their way down to my ass and he was gripping my cheeks and spreading them apart, opening me up even further, allowing his cock deeper access to my insides.
I was so turned on I could barely take it. I was close to cumming but I needed to switch things up to get myself over the edge.
So, keeping Scott’s cock deep inside of me, I spun around so I was facing away from him, riding him reverse cowgirl. I grabbed his knees and pushed them closer together, then adjusted my body so my feet were on the floor, giving me more leverage to work with.
Once I was properly positioned, I began slamming down onto him harder than ever, impaling myself on his cock. His hands were on my hips, holding on for dear life while I pummeled him, my ass hammering down onto his legs.
“Holy shit that feels so fucking good,” Scott said.
“Fuck yeah it does,” I said. I put my hands on his knees and bent forward, then started pounding him even more aggressively.
His cock felt incredible inside me but I still needed something more. “Slap my ass,” I said.
Scott did as he was told.
“Harder,” I said. “Like you mean it.”
So he did, smacking my asscheek again.
“That’s right,” I said. “That’s what I’m talking about. Keep going. Don’t fucking stop.”
I continued pounding away at him, smashing his balls as I dropped my body onto him with full force, my breath growing quicker by the second, while he continued smacking my ass.
“Yes, yes, yes!” I screamed. My ass was starting to hurt a little bit from all the slapping but the pain was just getting me more excited. “Right there, right there, holy fuck, right fucking there!”
Scott turned up the intensity even more, smacking away at my ass relentlessly. My screams turned wordless and reached a fever-pitch, culminating in a final, expletive-laced, ear-splitting bellow as I reached orgasm. My body shuddered and shook but I didn’t slow down, still pounding away at him for a few more seconds before finally falling still.
I didn’t have much time to relax though, as Scott wrapped his arms around me and climbed up from the couch, letting his cock slip out of my pussy for the moment. As soon as he rose to his feet, he turned around, then dumped me onto the couch. He knew
I’d just cum and now it was his turn to finish up, which was perfectly fine by me.
Scott grabbed ahold of my legs and pushed them forward, lifting up my ass to give himself a better angle to work with. Holding my legs in place, he slipped his rock-hard, monstrous cock into my soaking wet pussy. I took it all the way inside me without any resistance.
Perhaps because he was already so far along, Scott pounded me with everything he had right from the beginning, giving me his entire cock with every thrust, holding it deep inside of me for just a moment before pulling it almost all the way out and slamming it back into me.
I was way too into it to talk by now. I was relegated to growls and grunts and the occasional curse word as Scott hammered me practically into submission with his cock.
And just when I thought he couldn’t possibly fuck me any harder, Scott grabbed a hold of my ankles and forced my legs back even further until I was essentially folded in half, my legs pressed against the couch, one on either side of my body.
This position allowed Scott to use gravity and all his weight to pound me with everything he had, his balls slapping against me, his body hammering down on mine hard enough to make me flinch as he bottomed out.
I let out a wordless cry full of pleasure and just a hint of discomfort, my eyes wide and my body tingling with pleasure. I hooked my own arms around my legs, freeing Scott’s arms up. He shifted slightly, putting one foot up onto the couch, giving himself even more leverage. With his hands gripping the back of the couch for support, he fucked me with furious intensity, as though trying to break me in half.
Scott’s grunts and groans and breathing rate intensified, as did mine. Our faces were just a inches apart and we stared intensely at each other while I quickly approached yet another orgasm.
“Give it to me, give it to me, give it to me!” I said, somehow finding my voice. “I’m gonna cum again, I’m gonna fucking cum!”
And cum I did, my body tensing up before releasing in a massive, violent orgasm, the strongest one of the night.
Almost as soon as my orgasm passed, Scott’s arrived. As he rose towards orgasm, he started pounding me harder than he had all night. It took everything I had to not scream out in pain, but I knew he was nearly done, so I took what he had to offer.
“Oh my God I’m gonna fucking cum,” he said finally.
“Come inside me,” I said, barely able to get the words out. “I want to feel your seed inside my body.”
Scott didn’t have to be told twice, cumming mere seconds later. His hot jizm felt great inside me, filling me up, buckets of it from what I could tell as he squirted at least seven separate times inside me.
Eventually he fell still, finally spent. He rolled off of me and flopped onto the couch, clearly worn out.
Smiling at him, pretending like I was doing fine, I rose up and poured us both glasses of wine, dusting off the last of the bottle.
“A toast,” I said, handing him one of the glasses then clinking mine off his. “To the beginning of a wonderful friendship. With benefits, of course.”
“Of course,” he replied, taking a drink of his wine at the same time I did.
“I only wish I’d known you were into women earlier,” I said, even I didn’t know if I actually meant it. Who knows how this night would have turned out if I hadn’t thought he was off limits all this time. Certainly not the same. And considering it had been pretty much perfect, perhaps there was no reason to cry over spilled milk. Besides, we’d have plenty of time to make up for the amount that was lost. Plenty of time indeed.
#####
TOP SHELF COUGAR
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.
“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.”
Bend Over Babes - 4 Dirty Stories Page 5
