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Two Cougars Ch. 02

"After a night of drinks, I take two curvy cougars to a hotel..."

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Chapter One

The Hotel Room

“Well, I’m sitting, so you don’t get the full effect,” I tapped the low side of my waist where the small amount of skin and fat I did have on my body accumulated and hid my lower set of abs. “My eight pack is more of a 4… 4.5?” I shrugged, looking down at my flexed chest.

While judging by Helen’s and Trisha’s almost completely naked bodies, I had been winning at strip poker in this hotel room I booked, the fact that I was sitting on the edge of this bed in my boxers was proof that I hadn’t won either.

“Oh, I have to feel–I’m sorry,” Trisha said, throwing her hands up and shaking them as if quieting a crowd of spectators. Trisha wore a white bra that made her large, natural breasts bounce up together on their own. The shirt and pants she once wore were now draped over her thick, bare thighs, and what little pudge gathered at the bottom of her belly. If we hadn’t consumed the absurd amount of alcohol at the bar already, I doubted that the quiet Trisha I met earlier tonight would even consider appearing like this.

 She stood up from her chair on her side of the table and groped at my chest. Her fingers explored the grooves between my pecs and slid down to the top of my shredded abs. My eyes lingered on her white panties that hugged her hips and crotch. I felt her delicate touch and saw the way her eyes lit up and how she chewed on her lower lip.

“It’s like feeling a gym poster come to life! And you’re a teacher?”

Helen laughed, smacking her own thigh as she took another long pull at the whiskey bottle. Helen’s confidence seemed unwavering, even half-naked. Her mature body was covered in faded tattoos. Roses on her waist that disappeared under her black panties. A tribal symbol was designed between her breasts that reached up from her cleavage. She leaned back, owning her curving body without a care in the world. Teetering her Jack Daniel’s bottle in her hand, Helen shook her dirty blonde hair to one side as she stared at me.

“I like to work out,” I said. My eyes, though distracted by Trisha’s wondrous eyes and flushed cheeks, could stay away from her round ass that was protruding beside his shoulder, nor could he ignore her exposed plump breasts that were inches from my face.

It was a combination of the liquor and how horny I was at that moment, but my left hand raised from the mattress and cupped her right ass cheek.

“Whoop, oh my!” Trisha jumped out of the trance she was in, feeling me when she felt my grope.

“Oh, sorry, I thought it was only fair that if you felt me I got to feel you,” I said, honestly not knowing where my sudden confidence came from.

“Oh, nope, no, you're fine… you're fine. It’s just, um,” Trisha cleared her throat and placed her palm on her chest as if she was trying to slow her heart. My warm palm slid slow, wide circles over her ass cheeks as she tried to focus. My fingertips gently traced beneath her white panties where her cheeks met her thighs. With each rub, my fingers pushed closer and closer to the fold of fabric where her panties bunched and disappeared between her thick thighs. “I-I, um, wow, is it hot in here?” Trisha laughed as she fanned herself, looking at Helen.

“No, but you are, girl,” Helen shouted as she clapped her hands excitedly. “Sexy ass birthday girl! Granny panties and all!”

I didn’t think Trisha’s face could get any redder, but it was as she fought back a smile and gave her laughing best friend the middle finger. It was almost the same moment; I slipped my middle finger down from her ass crack between her thighs and felt the warm moist fabric resting atop her sex as I reached my finger deep between her legs and slowly dragged it backward over her slit through her dampening underwear.

“Oh, my… god…” Trisha’s hands shot to her mouth as she formed a tent around her lips as if she thought she might scream. “It’s, um, it’s just been a while since, wow-oh my god…” she stepped out with one foot, widening her stance for me, and had to reach out and grab my shoulder to balance herself. With more room, my finger reached through the gap and could rub the fabric over her clit. “Oh my god, don-your, oh, we really shouldn’t be doing this,” Trisha giggled nervously as she looked down at me. She saddled closer to me, though, and leaned more on my shoulder.

My multiple fingers now rubbed her panties and began to press harder on her sex as I felt a damp circle forming in the center.

“Why not?” Helen protested. Her intoxication was evident in her volume. “We’re all adults. Besides, it’s your birthday!”

“It is your birthday,” I said.

Trisha looked down at me with pouty lips as if making a decision. I smile and shrug as I bring my right hand to the front of her sex. Without warning, I pulled her panties to the side with my left hand and slid my middle finger between her wet pussy lips, entering her slowly. She gasped, and her eyes went wide as she was shocked at the moment. I held her gaze as I pushed my finger in and out of her slowly, over and over again, as her mouth hung open in a silent scream.

The room went quiet as Helen just watched and groped her own breasts before sliding her palm between her thighs.

Chapter Two

The Bar

“Jesus, this place is packed,” I said as we drove by Jack’s Bar and Grill. The parking lot, which was already small and covered in potholes and faded yellow parking lines, was completely filled.

“I told you, hun,” Helen slapped her knee, “too many people are livin’ here now. They need to go.”

I laughed and heard Trisha in the back seat lean forward between our chairs. “You can park across the street at the hotel. That’s where we park when we drive.” She said, pointing at a run-down motel with a red vacancy sign in the front window. It was strange seeing all these places. I left this town seven years ago for college and never really returned. I had visited my parents, of course, multiple times over the past years, but usually just stayed in the house for a weekend, or the three of them visited a nearby city on a mini-vacation. My mother used to love those brief trips. Shopping locally and helping small businesses. She was a good woman. Could never pass a homeless person on a street corner without giving them something.

Smiling as I got out of the vehicle, I shook my head at the nostalgic memories when I caught Trisha studying my expression. I didn’t want to think of my dead parents right now. I had spent the past month wallowing in self-pity long enough. This was one of the few times I’ve been out of the house and had a chance to take my mind off things.

Jack’s looked, smelled, and felt just the way I remembered it. In high school, my friends and I would come here on the weekends, and if we were lucky enough to have the right combination of bartenders and patrons, we would stumble out at night drunk. The stain of cigarette smoke on our clothes from the outdoor patio and the souls of our shoes sticking to the floor with each step.

The small wooden bar in the corner was packed with people on stools. Old timers, regulars, and a few younger faces standing around them waiting for their drinks. The tables and booths were mostly full with couples and friend groups as they ate appetizers and downed beers. The jukebox roared mostly oldies from a few decades ago. Fan favorites.

Helen brought us to her usual table, which still had remnants of empty glasses and plates. “First rounds on me.” Helen winked as she took her purse off and hung it on the chair.

Trisha stacked the plates and glasses to the side of the table, and I quickly joined her in grabbing a handful of napkins to wipe the table down. “Oh, I can do that.”

“No, please. It’s your birthday, right? Take a load off!” I smiled.

Trisha rolled her eyes and shook his head as she sat down. “Please, I’m old, but I’m not that old.”

“You’re not old. You look great.”

Trisha blushed and seemed to try to make herself smaller in her seat. I felt bad but found myself extremely attracted to her. She was in great shape, with an hourglass body, a round butt, and large natural breasts. She seemed uncomfortable with how revealing she was dressed. Maybe Helen picked out her clothes for tonight’s occasion. Maybe Helen said something like, ‘Here, wear this tonight. This will surely get you laid.’

Trisha noticed me leering at her cleavage, and I quickly averted my eyes. A coy smile grew across her lips. “How old are you?”

“Twenty-four,” I said.

Her eyes widened, slightly alarmed, before she covered her eyes with a hand. “Oh, my god…”

“What? How old are you?”

After a long sigh, Trisha said, “Thirty-Eight… today. We’re a whole generation apart. Way too old for you.”

I smirked, “way too old to do what?”

Trisha stuttered and looked as though she couldn’t get any redder in her cheeks.

“Trisha, I didn’t think I’d see you here,” a high-pitched voice said over my shoulder.

When I turned to look, I nearly had a face full of breasts as the woman hovered so closely behind me.

A surprised look broke across Trisha’s face as she seemed to force a fake smile. “Hi Cynthia, how are you?”

Chapter Three

The Hotel Room

Trisha looked down at me with pouty lips as if making a decision. I smile and shrug as I bring my right hand to the front of her sex. Without warning, I pulled her panties to the side with my left hand and slid my middle finger between her wet pussy lips, entering her slowly. She gasped, and her eyes went wide as she was shocked at the moment. I held her gaze as I pushed my finger in and out of her slowly, over and over again, as her mouth hung open in a silent scream.

The room went quiet as Helen just watched and groped her own breasts before sliding her palm between her thighs.

“Oh, god!” Trisha gasped and stepped towards me. Her hips turned to face me, and suddenly, her knees were touching mine, and my lips were brushing just above her navel. Her hands grasped at the back of his head and neck, holding me to her soft skin as squeaks and gasps escaped her lips.

“Ah-ah ah, oh my god… oh my god…” she moaned as I slipped a second find inside her pussy. Her fat breasts bounced above my face as her hips shuddered, and she looked at the ceiling.

“Hey, now,” Helen said, taking another long gulp from the whiskey bottle as she stood. “That’s not fair. I want some of that!” She whined.

Helen stumbled over to my right side, sliding the table away so she could go beside her best friend. I could see Helen’s tattoos populating all over her bare arms and thighs and a few looping roses on her ribs. The roses went all the way down to her thigh on her left side. As my fingers pumped inside Trisha, Helen bent over in front of her, gripped my cheeks with her hands, and slid her tongue into my mouth as she kissed me. Her jet-black curls shrouded the sides of his face as her tongue lapped mine. I could taste the Jack Daniels on her tongue and feel her hot breath on my lips.

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My cock swelled in my boxers, and I felt it begin to stretch the fabric as I wished I had more hands as I would have loved to grab Helen’s massive breasts at that moment. My finger slowed inside Trisha, and I felt her begin to retreat and pull away. My fingers clung to her panties, and Helen straightened with a humming moan.

“Mmm mmm mmmmm,” Helen said, breaking the kiss as her hands grabbed at her friend’s hips.  “Where do you think you’re going?”

“No, it’s okay, I can, um, just sit. I’ll just go over here and you guys can-‘’ Trisha panted, looking around the room.

“No, no, no, birthday girl,” Helen said. “This is your birthday, now, so here. Have a seat.”

Pushing the table away, Helen made room and pushed Trisha despite her protests towards me. I quickly pulled my fingers from Trisha’s panties as she nearly fell on top of me. She caught herself at the last moment and was able to straddle me on the bed, putting a leg on either side as I laid back on the bed. Watching Trisha pull her hair to one side, my eyes fluttered from her lips to her eyes as her face hung inches above mine.

There was something different in the chemistry between me and her. Something more electric. My hands carefully slid up her body, cupped her face, and guided her lips down to mine. The tender kiss exchanged between us two was transformative. It felt as though we were not only alone in the room but alone in the world. The last survivors of some cataclysmic event or another. Ignorant of their doom and lost in the moment of this eternal kiss. I felt her arms close around my shoulders and face as she arched her back and pressed her breasts into my chest.

The only thing that woke me from that moment was the startling feel of Helen’s hand finding my flexed shaft and stroking it through my boxers. After several rubs, she found the hole in the front of my boxers and fed the begging shaft through it. It was a strange and almost helpless feeling I felt. My arms and sight were completely engulfed by the beautiful Trisha before me as we kissed deeper and deeper in our obsession. With that, I was completely unaware of what Helen did with my cock at the bottom of the bed.

Helen’s small hand struggled to wrap around my flexed shaft and began pumping it bare. She squeezed my shaft, and my shaft flexed back in her grip. Trisha’s kiss became deeper and more obsessive as the pumping of my cock grew faster. There was tension in my shaft as it was strained and pulled to the side and quickly overwhelmed by the feeling of the wet warm lips of Helen’s mouth engulfing the tip of his cock.

I groaned into Trisha’s mouth, which licked the roof of my mouth as I sucked on her tongue; one of our hands intertwined fingers over my head, uniting each other, while my right hand cupped and squeezed at her left breast. Feeling her soft skin and full breast. I tried to hold my grunt as Helen pushed her lips down my throbbing shaft over and over. She cupped my balls and stroked the base of my cock–the part she couldn’t fit in her mouth.

There was a slurping sound, followed by Helen’s gasps as she stood upright over Trisha’s backside. There was a devious look on her face. Suddenly, Trisha broke the kiss with a shocking gasp. I worried I might’ve done something wrong when Trisha looked at me, then gasped and looked over her shoulder.

“Helen! Is that–oh god, what are ahh!” Trisha moaned, squinting her eyes.

“Mmmm… I thought I would have to slick your pussy up, honey, but damn, you're dripping, baby,” Helen bit her lip as she hovered over her best friend’s back. “What? Does my fingers sliding in your pussy feel good?”

Trisha stood tall on her hands and knees with a small dip in the small of her back as her body went stiff. Helen rocked her hand back and forth, fingering it hard, making her squirm and scream. The moment only lasted a few seconds until Helen pulled on and giggled to herself as she licked at her fingers. Helen worked my shaft, pumping it as she pulled on Trisha’s hips and lowered her pussy back and down on the head of my cock.

“Ohh gah!” Trisha’s eyebrows went tall.

“Oh my god, Trish- I… I don’t know if you can fit this boy- oh…” Helen commented, cupping a hand over her mouth.

“Jesus Chris- ahh!” Trisha cupped a hand over her mouth after swiping her hair out of her face. The head of my cock stretched her pussy lips as I slowly stuffed her deeper. Inching my cock higher and higher as I felt her warm and wet lips swallow my cock. Her pussy squeezed and flexed around his shaft.

“Ahhh! Oh god!” Trisha cried.

“Mmmm, you’re doing so good, baby, yes, fuck that pussy,” Helen encouraged as she stripped completely naked.

Trisha sat back completely and left, her pussy stretched to its limits with most of my cock stuffed inside. I could see her face was a mix of exhaustion, pleasure, shock, and confusion. Tisha was drunk on the feeling as she slowly circled her hips on my shaft. The moment of ecstasy built as I watched Helen crawl onto the bed beside me. Her extra-large breasts swayed from side to side between her arms as she saddled beside my face.

The moment was so surreal, even in my drunken state, to feel my cock flex and ooze pre-cum inside this gorgeous milf as another girl neared and smiled down at me.

“I have to get in here,” Helen panted. “Playing with that big cock made me so god damn wet, baby.”

Helen leaned over, kissing me wildly. I tasted the liquor on her tongue as she shoved it deep down into my mouth. Her perky, full breasts mashed into my chest as she bit my lip and grabbed at my hair. Slowly, I felt Trisha lowering and raising on my cock as her squealing began.

“Ahhmmm aaah.. ahh…” Trisha groaned.

Helen broke from the kiss and, without asking permission, maneuvered her leg over my face so her thick thighs surrounded my cheeks, and I watched her wet, shaved pussy lips lower onto my face.

Reaching around her legs, I cupped her ass cheeks and used my fingertips to spread her lips as I made a long wet lick across her entire pussy. Quickly and repeatedly, I licked her pussy lips again and again and felt a quiver go through her inner thighs as I heard her cry out.

“Oh baby, yes, get in there, lick my pussy, baby,” Helen cried. Pushing my tongue deep inside her pussy, I tasted her pussy, drowning my tongue. Juices poured around my tongue. At the same time, Trisha had gotten used to the girth of his cock enough and began to ride me like I was her dildo. Her pussy bouncing up and down on my cock harder and harder. Her pussy lips choked my head, milking it with every raise on my shaft.

I felt hands on my chest and stomach rubbing and bracing themselves as they rode various parts of my body. My tongue made long laps on Helen’s clit over and over as I felt her thighs flex and tighten around my cheeks. I gasped for air as I spread her pussy lips wide, and tongue fucked her pussy over and over again. Her juices drip to my cheeks as I push my tongue deeper.

“Ah ah ah ah! Oh my… oh my god!” Trisha moaned as she rode me harder. Her fat ass cheeks smacked against my thighs with every thrust down on me.

“Oh, my god, baby, you're so fucking good with the fucking tongue!” Helen yelped. At her moan, I wrapped my lips around her swollen clit, sucking on it. Harder and harder, I sucked on her clit. Helen gasped, and she moved to try to lift off of my face, but I wouldn’t let her. Holding her down on my face, I dragged my tongue across her clitoris. “Fuuuck! Holy fucking shit! Yes! Yes!”

Helen sucked in a deep, ragged breath and went silent as her inner thighs trembled around my face. My tongue flicked repeatedly on her clit, and a sudden jolt went through her body. Her muscles flexed and spasmed until she screamed.

“Oh, fuck! I’m cumming, I’m cumming I’m ahh!” She moaned, and I felt a stream of her juices fall down my chin and around my neck. I felt her hips tense like they were trying to pull away until, finally, she released a long sigh and relaxed her hips back down onto my face. She left her pussy to be cleaned and lapped at by my warm tongue, cleaning her up.

It wasn’t until Helen’s moan quieted that I could focus on the speed and force that Trisha was riding me. Her tight wet pussy slammed down on my hips with a roughness. I could see the corner of her massive tits bouncing wildly around Helen’s hips.

“Oh Jesus…” Trisha cried out as her ass clapped down faster.

Instinctually, my hands slid up blindly on Trisha’s body, and Trisha’s hand grabbed ahold of my hands, guiding them to her breasts. I squeezed them, mashing them into her chest, and pinched her nipples.

“Oh god! I can’t- I… Oh god, I’m gonna cum!” Trisha sang as her hips ground on my cock. Helen leaned forward and sucked on her friend’s neck. My hands that cupped Trisha’s perfect breasts were now mashed between Helen and Trisha’s fat tits. “Jesus Chrriiiisst ahhh!” Trisha came and convulsed on my shaft.

Helen rose off of me, and I felt how wet my chin was. Helen giggled as she bent down, shrouding me in her hair, and kissed me slowly, then licked and kissed at the juices on my chin. Trisha was panting as she slowly raised herself off of my shaft. My hard cock bounced erect as the two women sat on the bed on either side of me.

Helen broke away from the kiss and smiled down at my still-erect member. “Mmmm… I love fucking you, young guys,” she purred. Trisha ran a hand over her face and through her sweaty hair. Her eyes were dazed as if she was still trying to find her senses. Helen giggled more, “Come here, Trish.”

Helen gave her friend a lingering kiss that seemed to wake her up in confusion, but Helen quickly pulled on the back of her neck, lowering Trisha’s lips to my cock. Without prompting, Trisha’s lips swallowed the head of my cock, making me groan as Helen pulled her hair back into a ponytail with her fist.

Trisha’s head bobbed up and down eagerly. I could feel the warm pressure her mouth gave my cock. Helen’s hand and fingernails scraped my chest as she coaxed me.

“That’s it, baby, cum for us,” Helen said. “Cum in this birthday girl’s mouth.”

Trisha's sloppy lips slid down my shaft, and I felt it cumming.

“Yes, watch those slutty lips swallow you,” Helen purred. “Cum in your whore. Cum in her mouth.”

I groaned as my cock spasmed, and Trisha’s eyes went wide as I pumped loads of cum into her mouth.

“Yessss! That’s it, baby! Cum hard for us, yesss!” Helen commanded.

Trisha’s lips remained wrapped around my shaft as my cock flexed over and over. Slithering her tongue up and down the head of my shaft, Trisha swallowed every drop of my cum.

 

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Written by djmiles
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