Era Erotica Ch. 25

"Oh fuck! Yes! Fuck me! Fuck! Fuck! FUCK!" Hailee said, stretching her legs skywards.

Releasing her arms, I grabbed hold of each smooth calf and placing one on each shoulder. Her heels clicked together behind my head as my frenzied thrusting continued. Leaning forward, she suddenly felt her pussy stretching as my stiff fleshpole banged right into her g-spot.

"S-S-S-H-H-ITTT COLE! Oh my god! Right there! Fuck yea!" Suddenly, I felt her snatch tighten around me as her raspy screams reached an even higher pitch. "GOD! GONNA CUM! KEEP GOING!"

Leaning forward, her legs stretched even further as I pummeled her pussy for all it was worth. Her eyes crossed, before they rolled into the back of her head. Her fists balled up the sheets of the bed, and her mouth formed wordless sounds before she screamed out my name.

"COLE! COLE! C-C-C-COOOOOLLLLEEE!!

Her snug cunt closed even tighter as the orgasm racked her body. Guttural, animalistic noises emanated from deep in her throat. Her supple frame trembled and her legs squeezed tight around my neck as she climaxed spectacularly. And truth be told, I wasn't far behind as I kept up my frantic furious fucking.

"Hailee. Need. To. Cum." I grunted out, unable to hold out any longer.

"Mhmmm, cum here!" She said, licking her lips sensuously and uncrossing her eyes as I extracted myself from her and she spun around, flopping down onto her stomach.

Cock wet and shining, it throbbed as her lips wrapped back around the meaty fuckstick. Her head quickly bobbed along the shaft as I threw my head back, groaning louder and louder as I swelled inside her talented mouth before a pent-up torrent of thick creamy virile cum burst forth. Hailee's eyes went wide and she moaned appreciatively as her mouth flooded was with hot sperm, cheeks bulging as she continued sucking like a vacuum. Spasm after spasm, my cock fired out sticky jism until it was spent, relaxing with her lips still pressed tight around me. Releasing me, my dick fell from betwixt her lips, and she smiled up at me. Opening wide, she revealed the thick pool of semen held there. Her pink tongue swirled around the virile mixture. Leaning her head back, she gave a gargle, bubbling the goopy soup of seed before closing her mouth and gulping the whole thing down in one big swallow with the biggest grin of her face.

Smacking her lips appreciatively, she said, "So much and so good. If I were Taylor, you'd be giving that up every day! A perfect not-so-little protein snack."

Shrugging noncommittally, I fell onto the bed and closed my eyes. Taylor's cum covered face still appeared there. I felt Hailee get up and make her way to the bathroom. Busing herself, it was several minutes before she ventured back out.

"Oh my." I heard her exclaim.

I quickly opened my eyes. "What's wrong?"

"Nothing! Nothing at all! It's just...you're...you're still kind of hard is all."

"Ummmm..." I said, hurriedly sitting upright. I'd been lost in a fantasy of a different version of this night. One spent with Taylor.

"Do...do you want go again?" Hailee asked, having the decency to look embarrassed.

"Hell yea." I said with a grin.

Hailee moved onto the bed, now completely naked, the trappings of her award show outfit now fully discarded. "Taylor said you weren't a one and done kind of guy." She pointed towards my member, getting even harder as the conversation dragged on. "And clearly she wasn't lying."

"What did she tell you about my pussy eating skills?" I said before gently grabbing her and tossing her flat on her back.

Spreading her legs, the singular landing strip of dark hair above her pink pussy lips gave me the perfect target as my tongue pressed against her glistening velvety folds.

"She said you're better than Karlie!" Hailee called out, her voice high-pitched and breathy, already squirming from the sensation.

I tickled her stiff clit with the tip of my tongue, my lips running along hers. Our eyes locked onto one another, digging in deeper, stretching my tongue as far as it could inside. Hailee watched me with the hungriest of expressions as I licked, lapped, sucked and slurped every bit of labia I could get my mouth on. Hailee tasted different than Taylor. Not better or worse. Just different. Try as I might, I just couldn't get her out of my head. My arms wrapped around her thighs, lifting her up slightly as I closed my eyes, all my efforts focused on eating out the California girl. Hailee moaned and cooed, but I needed more. We both needed more.

"Come here." I said, prying my lips away from her pussy. "Turn around on all fours and get ready for round two."

"Doggystyle. I like it!" Hailee said with a giggle and assumed the position.

Getting on my knees, she presented her ass for me. I took a moment to admire it. Not enormous, but damn if it wasn't nice. A plump bubble butt with a fantastic curve and tight enough to bounce a quarter off of. Grabbing a handful of each cheek, I lined up my prick with her dripping twat and thrusted.

"Ffffuuuccckkk!" Hailee squealed as I stuffed her full again, sheathing myself to the hilt.

No time was wasted as I quickly built up speed, using her hips like handlebars. Before long, the sweaty clap of pelvis-on-pelvis echoed around the messy bedroom. Each frenzied thrust of my hips sent my balls slapping against her clit, coming away wet with arousal. Every so often her head turned to stare at me, biting down on her lip in-between moans as her eyes rolled every which way. Her once sleek and shiny dark brown hair was a mess. The very definition of bed head. A deep, throaty guttural growl escaped from me and I drilled her even harder, desperate to get the images of Taylor out of my head.

Prying those pert buttcheeks apart once more, the tips of my fingers ever so lightly tease across the rounded entrance to her backdoor. It elicited a shudder that reverberated throughout her entire body, one so strong that made me slow down.

"Mhhhmmm...so, tell me. Does Taylor let you fuck her in the ass?" She asked, turning her head, my thumb now pressing lightly against her rosebud.

"Sometimes." I blurted out without thinking.

"Ohhhhh really?" Hailee asked, now sliding herself slowly along my length. "She lets you stick that monster up her butt?" She paused, as though considering something. "Well, if it's good enough for Taylor Swift, it's good enough for me."

"What are you saying?" I asked, my brain a fuddled mess with her tight cunt still wrapped around me.

"Fuck me in the ass."

"You sure?"

"Uh-huh. But you need to warm me up first. Use your fingers."

If this didn't get my mind off of Taylor, then nothing would. Quickly, I popped two fingers into my mouth until they were dripping with spit. I pushed them against her brown starfish, spitting on it for good measure. "Ever done anal before?"

"Never with anything that big. Fingers, tongues and toys only. The squad is very forward thinking when it comes to backdoor fun." She looked back at me, batting her huge hazel eyes. "I hope I can handle your big hard cock."

That was apparently the right thing to say as my big hard cock swelled another inch inside of her at those words. Keeping a slow and steady pace, I continued fucking her as my fingers slowly worked their way in and out of her asshole, continually spitting on the ever-loosening backdoor. A few more minutes of that and she gave me the green light. Quickly, she opened a nightstand drawer and grabbed a bottle of lube, but not before I spotted a couple of other brightly colored instruments of female pleasure. Pulling out of her with a slurp, I drizzled the veiny shaft and doused her winking butthole with the slippery stuff. Then I pressed my swollen crown between her cheeks.

"Go slow." She said, already breathing heavily as her perfectly manicured fingers teased her clit in small concentric circles.

There was some resistance, her taut sphincter struggling to accommodate my fat cockhead. Hailee took a deep breath and played with her pussy even more. I continued pressing until the crown was enveloped and I slipped inside with a loud grunt of satisfaction. Slowly I crammed inch after veiny throbbing inch up her asshole. A quiet whine escaped from between her generous dick sucking lips.

"Want me to stop?" I asked.

"God no! Keep going! Just slow!" She said breathlessly.

It was indeed slow going at first. The first pass saw only about half my length fit inside, but with each repeated motion it became easier and easier. After my entire member was vanished from sight, balls flush with her taint, it was all downhill. Before long, I was slamming into her, each thrust rippling her supple booty with the force of my hips against hers. Every possible millimeter of my cock was being squeezed by her rectum. And it absolutely did the trick. For the first time that whole night, my mind was totally free of any thought of Taylor Swift as I railed Hailee Steinfeld straight up the ass.

Hailee seemed to be having the time of her life. Her screams of pleasure reverberated around the room, sending my eardrums a rattling as I gave it to her up with the butt with renewed and vigorous energy.

"COLE! FUCK! THIS FEELS AMAZING!" She screamed out. "FUCK THAT ASS! YES! YES! OH GOD! FUCK THAT ASS!"

We remained locked in our doggystyle position. Unwilling to pause for even a moment to switch up the anal pleasure. Already Hailee was leaking more than a faulty dam. Her body tensed up as her screams intensified, orgasm close. Even though I'd just met her tonight, I could tell. So, I dug my fingers into that fine behind and pounded. Hailee's arms gave out, her face falling into the cascade of soft sheets as I rammed her butthole, clenching ever tighter around me. Then it hit. The orgasm rolling over her body like a tsunami crashing on a beach.

"CCCCUUUUMMMMMIIIINNNGGGG!!" She screeched, so loud even with her face buried in the mattress.

She didn't squirt, like Taylor did so often whenever we engaged in anal play, but the rush of fluids that flooded her loins dribbled down freely like a leaking faucet. Her sphincter squeezed me harder than ever before, so tight, it was felt like my dick might fall off. It all proved too much for me.

"Oh fuck! Gotta cum! Hailee!" I shouted.

"Mhmmm! Pull out!" Hailee said, just coherent enough to put those two words together.

Wrenching my cock from her snug asshole, the dark gaping chasm seemed to stare back at me before she spun around. Before I could even fist my prick, her succulent pink lips opened wide and swallowed me right down to the base. Positively howling with pleasure, the feeling of her hot, wet mouth had me spurting in seconds. The entirety of my balls were drained, as for the second time that night I sprayed the inside of her mouth with searing hot ropes of sticky cum. Wide hazel eyes never left my face as she greedily gulped down every ounce of cum I could produce. Utterly spent, she sucked my dick clean before releasing me with the loudest *POP* of the evening.

Feeling like my very soul had been sucked out, I asked, "Wow. Ass-to-mouth on the first date?"

Her pink tongue was licking her pink lips, tasting the remnants of sexual fluids gathered there. A look of realization slowly fell across her sexy-cute features. "Oh my god. I guess I did. I just love swallowing. Didn't even think about it really. Huh." She shrugged and laughed. "You know what? Still tasted great. Better even."

After that, the night was a blur as sleep quickly overtook both of us. I awoke the next morning, momentarily unsure of where I was. Taylor's room? No. The sound of a shower could be heard, traces of steam curling out from around the slightly ajar door. The events of the previous night swirled around my brain, along with the leftover dregs of alcohol. I got up and immediately stumbled over a pair of golden heels. I swore loudly.

"Cole?" Hailee called from the bathroom.

"Yea?" I replied.

"You're up...do you need a shower? I've got a pretty big one in here. Room for two."

Making my way over to the bathroom, I pushed open the door. Waving an arm through the haze of steam, the wet, soapy sight that present itself before me was far too resisting to say anything but yes.

2019

Cole sat up, the memory of that night and the next morning fresh in his mind. He wasn't mad anymore. Just sad. It wasn't the sex that stuck out strongest. It was the longing for Taylor. Those secret feelings that he'd tried to squash for years, but could never quite manage it. That night with Hailee had been great, but it had just been a desperate attempt to repress those feelings he had for her. Standing up, he still didn't know exactly what he was going to say in apology, but headed for the door nevertheless. Gripping the knob, he pulled it open and was greeted by Taylor standing there, fist raised as if about to knock. She looked at him through watery red-rimmed eyes.

"Hey." She said quietly.

"Hey Swift." He said, taken aback by her sudden appearance. "I was just coming to apologize."

"So was I." She said, a half-grin forming on her face.

"I'm sorry." They both blurted out at the same time.

"Let me!" Taylor butted in first. "I had no right to be angry. You didn't know the rule. It's just the thought... the thought that we wasted all those years on other people."

"That wasn't time wasted. It brought us here. Together." Cole said. "And I'm sorry too. I should've said no. I never did want to sleep with any of your friends. Only you. But that night. He was showing you off like a trophy...and then I saw you two going at it...I just needed to think about anything else. Hailee was an easy out."

"I get it. More than you know. Besides, it's really Hailee I should be mad at."

"So, we good?" He asked hesitantly.

"We good." She said, smiling. "Fight's over. That means makeup sex."

"Oh hell yes." He replied, stepping aside and gesturing for her to come inside.

And 45 minutes later, he was the one cumming inside.

End of Chapter Twenty-Five