Era Erotica

Disclaimer: This is a work of fiction. It is not real. It did not/will not ever happen in real life and should not be mistaken or confused as such.

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Chapter One: Taylor Swift

Codes: MF, Cons, Oral, Virgin

2018

Cole stirred as his phone buzzed, the screen illuminating the darkness of his room. He groaned and rolled over, blinking blearily as he looked to see who would be calling him at this hour. Her name was emblazoned across the screen. Becky. He reached over and clumsily groped for his phone with unresponsive reflexes. He swiped, answering the phone just in time.

"Hello..." He asked groggily into the darkness.

"Cole? Did I wake you? Shit, what time is it there?"

"Do you mean here in New York, where you allegedly live? It's 3:30 AM."

"You were asleep."

"Yes, I was Swift."

"Shit, I'm sorry! I always mess up the time difference."

There was a slight slur to her words that made him think she might have been drinking.

"It's alright Swift." He said as an enormous yawn overtook him. "I always have time for you. I'm glad you called."

He rolled onto his back, sinking deeper into the sheets, eyelids feeling heavy. The thoughts of their last conversation suddenly weighed heavily on his mind. It had been a while since they had spoken and they hadn't left things in a great place.

"Yea...I was just doing some thinking...but you know. It's nothing, just stupid stuff. Reminiscing is all. I didn't mean to wake you."

"Nonsense, I'm very much awake now. You might as well spit it out."

"You remember when we met, right?" She asked hesitantly.

"Of course, two middle school misfits thrown into the vicious Pennsylvania school system."

"Do you ever...do you ever wonder if things had been different?" She asked.

"Like how? Like if the other kids had never been such dicks, we would have never met?"

"No... like the later stuff."

"Gotta be more specific Swift. I lied earlier about being 100% awake."

"I meant like us being together. You know, the first time?"

That caused him to perk up a bit. Was this just another booty call? Over the years there had been many. It usually happened in-between shitty boyfriends and high-pressure album releases. Sometimes he wished it had been more than that. Still, there was no way he would ever forget their first time together. It had been over a decade ago and he could still picture it as clear as day.

"Yes Taylor. I remember it." He said quietly.

"Do you ever wish we had maybe done things differently?" She asked just as quietly.

"You know that I have, but I never once regretted it. I care about you too much."

There was a long pause. Cole didn't break it and neither did Taylor.

"Let's just talk in the morning. Sorry to have woken you!" She said a little breathlessly.

"Swift! Wait!" He said quickly, but she ended the call.

He thought about calling her back. He thought about telling her what he had often thought about over the years, long before she had been famous. Then he thought about when he had told her those things before and where it had sent them. So instead, he put his phone back on his nightstand and settled back into bed, now very much awake.

"Our first time. Now that was really something." He said out loud to himself. No one else was in his apartment to hear him.

2007

My phone vibrated, buzzing on my desk. I glanced over to see the number. A wide grin broke out over my face. I grabbed it, flipped it open and pressed the answer button.

"Swift!" I exclaimed excitedly. "You got my message? How was the latest gig? I haven't seen you in ages! How have you been?"

"Cole!" She squealed into the phone. "I know. I know. It's been a year of this and I still can't believe it."

"I never doubted you for one second."

"Liar." She said with mirth in her voice.

"So, what's up?" I asked. "Will you be home the weekend I am coming down?"

"Yes, I am! I'll be home for a few days next week. I was hoping we could hang out, just the two of us."

"Ah, well no worries on that front. I'm staying on campus with my cousin for the weekend while he gives me the real tour of Vanderbilt. I can easily slip away for a while."

"Excellent! How's everything else going?" She asked.

"Well, Stephanie dumped me a couple of days ago." I admitted. It still stung a bit, but it actually felt good to say it out loud. "So, high school has been more terrible than usual lately."

"Oh, Cole. I'm so sorry."

"Hey, don't sweat it. It's not your fault."

"I do wonder what high school would have been like together if I had never moved away."

"Taylor. Never apologize for wanting to pursue your dream. All those other dickheads couldn't see that. My time will come, eventually. I'm good really. I have missed you though."

"Damn. My manager is calling me to talk to me about something. I can't get five minutes to myself. I'll IM you the details. Sound good?"

"Sounds good. Bye Swift."

"Goodbye!"

She hung up the phone. It would be good to see her. She had been away for some time, working on various promotions and shows for her debut album. She was actually starting work on her second album. It was nearly Christmas time when I flew down to Vanderbilt to meet up with my cousin. Taylor's 18th birthday had only been a few days before and so I brought a present with me, some custom designed guitar picks. The trip was promising to be an exciting one, even though senior year of high school was proving to be a stressful one. It felt like I was wading through a never-ending sea of college applications. It was frustrating doing all these essays when I only ever wanted to go to Vanderbilt in Nashville, Tennessee.

It was hard to explain my friendship with Taylor Swift. We had met in middle school and gotten close. That had been a rough time for both of us, but then she moved away to pursue her musical career in Nashville and I was stuck back in Pennsylvania. High school proved better for both of us, but it did seem like we both missed each other's company. In many ways we were very different people, but something about her drew me like a moth to a flame. We still kept in touch frequently and I supported her whenever I could make it to one of her shows.

As the weekend arrived, I flew in met up with cousin and told I was meeting a friend for a while. He was pretty busy with finals so he didn't mind at all. My excitement as seeing Taylor again had reached its peak. She came over the campus and picked me up. She ran up to greet me, throwing her arms around and I was treated to a face full of that curly blonde hair. She looked beautiful even wearing jeans and a t-shirt. I presented the guitar picks for her. She exclaimed over them and gave me another great big hug. We totted around the campus for a while, catching up and reminiscing. Finally, she suggested that we continue hanging out at her place. I heartily agreed and she drove us home, blasting the radio and singing at the top of our lungs all the way there. When we arrived, I was surprised to find that her brother and parents were out. In fact, she told me that her parents wouldn't be back until tomorrow and her brother was crashing at a friend's house. We walked inside and we settled on the couch, laughing and continuing to catch up. As night descended upon the house our conversations turned from the superficial to the serious. Eventually she broached the topic of my recent ex-girlfriend.

"I don't really know what happened. I thought we were clicking, emotionally and physically." I said.

"Physically?" Taylor asked, sipping her beer.

"Yea...you know...like..." I stammered, suddenly bashful and feeling myself blush furiously.

"Actually, I don't know." Taylor said. "I'm still a virgin."

I choked on my beer, spluttering as I struggled to maintain my composure. I found her sitting very still, those electric blue eyes watching me very carefully.

"No...I...um...didn't know that Swift."

"Surprised?"

"Well...yes...I mean no." I stammered out stupidly.

"I know what you're thinking. Most of my songs are about boys. Right? The truth is that most of those were flings or silly schoolgirl crushes. I think part of the reason is because of the physical stuff. I've been called a prude by more than one of them."

"A prude? That's seems harsh."

"Well, you know I'm a good girl with proper moral values." She said as she sipped her underage beer.

"Sure you are Swift." I said chuckling.

"I've just never been that confident around boys. Especially ones that I think are cute."

"Ouch. You wound me." I said mockingly.

Taylor looked at me intensely and laid her hand on top of mine. "Expect for you."

"Ok. Very funny Swift." I said, waiting for the punch line to drop.

"The truth is Cole, that there isn't a boy in this whole world I trust as much as you. Let me tell you, getting into this industry...there just aren't a lot of trustworthy people. And the truth is that I've wanted to do this for a while a now. I just haven't found a trustworthy enough person to do it with. I thought...I thought..."

She paused here and took a deep breath as though steeling herself to say something. Then she looked me square in the eyes and spoke.

"I thought that my first time could be with you."

I sat there on her living room couch thunderstruck. Over the years, I had occasionally toyed with the idea of romantic notions with Taylor, but never anything serious. Now here she was propositioning me.

"Taylor...about us..." I began to say.

"Hey!" She said quickly. "I get it. I love our friendship! It means the world to me and I don't want to tarnish that. This would just be one friend helping another, right?"

"Yea... that's always how it works out in those movies you're always watching."

She chuckled, but still looked to me for an answer.

"What do you think?"

Hundreds of thoughts suddenly began bombarding my brain. The swarmed around my mind like a hurricane, each battling to be heard. Then I looked at her, sitting there in jeans and t-shirt on her parent's living room couch, curly hair falling around her shoulders, full pink lips, bright blue eyes and I banished all those thoughts.

"Yes..." I said quietly.

A wide smile broke out over her face and she leaned forward. I leaned forward as well and suddenly my nostrils were filled with the sweetest smell of her perfume. We paused for a moment, our lips centimeters apart before they touched gently. Her lips were incredibly soft, full and they tasted sweet like candy. It felt like we sat there for eternity, our lips locked and electricity flying between us. Eventually we came apart and suddenly she was quite pink in the face and looked down bashfully. I cleared my throat loudly.

"That was..." I said.

"Enchanting?" She said.

I nodded silently, eyes wide. I moved forward to kiss her again and she responded, parting her lips and we kissed again. This time I probed my tongue gently forward and she responded in kind. It was impossible to say how long we sat on that couch kissing, but eventually we broke apart and sat back, adolescent hormones raging through each of our bodies.

"Just so I know... how much experience do you have, exactly?"

"Subtle." She said laughing. "I've kissed my fair share of boys...but not too much more than that."

"Uh huh."

"It's not like I haven't thought it. I've gotten plenty of details from some of my other friends. I know where everything goes and all that. In fact, there was one time where I think I might have made him cum."

"You think? You can usually tell."

"There was a lot of rolling around and rubbing of things. Then we were interrupted. It's hard to say."

"So... you've never even seen..."

"Not in real life. Well, I've seen it through underwear and jeans."

"Doesn't count."

"Does too!" She said, miming offense at my comment. "Also, I...um... may have masturbated once or twice before."

I raised my eyebrows in response.

"Nothing wrong with that. Are you... are you sure about this?" I asked.

"You're the boy I trust the most." She said simply. "You just also happen to be my friend."

"Ok Swift. Then let's do this."

"That sure took a lot of convincing." She said mockingly.

"When a beautiful, funny, talented and smart girl wants to have sex with you, you do not turn her down."

She actually blushed at that and looked down slyly.

"Ok then. Meet me upstairs in a few minutes?"

I nodded mutely. She stood up from the couch and walked away. I watched her hips sway as she went. She lightly treaded up the stairs and then I was alone with only my throbbing erection to keep me company. The anticipation stretched those few minutes into what felt like hours until finally I heard her calling for me.

I quickly raced up the stairs to her bedroom. After a quick knock on her door, I was granted entry. The lights had been turned off, but Taylor had lit several large candles, which filled the room with a dim radiance. She stood across the room, clad in only a grey camisole and a pair of bright pink cotton panties. Her curly mess of hair fell around her shoulders and down her back. Her erect nipples were easily visible through the thin fabric of the camisole. I stood there, jaw agape and frozen in the doorway. Her beauty enraptured me. My erection throbbed uncomfortably within the confines of my jeans. She looked down shyly, as if embarrassed by the state of her wardrobe.

"Taylor..." I said, my mouth suddenly very dry.

"How do I look?" She asked sheepishly.

"Incredible." I said quickly. "Like a literal angel."

"Boys will say anything to get in a girl's pants." She said with a sly smile on her face.

I couldn't help but laugh at the absurdity of the situation.

"That is definitely true, but I still meant what I said."

"You're sweet. Now it's your turn. Strip down."

I hurriedly peeled off my shirt, noting that her gaze was fixated on me. I unbuttoned my pants slowly and then let them drop to the ground. I stood there in front of her with my boxer briefs pitching a tent. Her blue eyes grew wide and round as they stared at my crotch.

"Oh...my...goodness..." She said, transfixed. "It's big... I mean, bigger than I thought it would be."

"Want to see it?" I asked cautiously.

She nodded, curls bouncing around her head. I gradually lifted the waistband of my boxer briefs and then dragged them down until they fell around my ankles. My member popped free, standing at attention. I had only ever been with one girl before, my ex, but she had never looked at me the way that Taylor was now looking at me. She was biting her lower lip, staring and utterly transfixed my manhood.

"That's supposed to fit inside me?" She asked with a little giggle.

"That's the plan." I said, heart thumping in my chest. "Want to touch it?"

She nodded and we moved towards each other. Inches apart, I moved in for a kiss and the instant I felt my lips touched hers the sparks flew between us. She pulled in close, pressing up against my erection as I savored the sweet taste of her lips on mine. I felt her delicate hand slide down from my back inching slowly to my cock pressed up against her. She moved her thin fingers to grasp it and she held on lightly before starting to move up and down very slowly.

"It's very smooth." She whispered.

"Let's move to the bed." I said breathlessly.

We moved together as one, lips still locked and her hand still gripped around my prick. We fell onto the sheets and I ran my hands over her body and breathed in the scent of her hair, an intoxicating coconut smell. We lay there, just taking in each other.

I pulled back to look at her and said, "I'm totally naked. How about you?"

She looked at me, smiled and stood back up at the edge of the bed. Slowly, she stripped off the camisole, one strap at a time. She pulled it over her head, revealing her petite breasts with very perky pink areoles. Then she hooked a thumb in her underwear and pulled slowly downward, revealing a trimmed blonde bush. She looked back up at me, covering herself shyly, holding an arm across her breasts and concealing her vagina from view with a hand. My eyes grew wide and I stiffened further as she stripped.

"Taylor Swift, you might just be the most beautiful thing I have ever seen."

She gave a trilling laugh and slowly removed her limbs, giving me a full view of her body. My eyes roved up and down hungrily, taking all of her in. Then she moved forward, back onto the bed. She kissed me fiercely again, our naked forms intermingling. We rolled around on the bed, passionately kissing and savoring the taste of each other's lips and feeling of soft skin. Gradually I moved my hands down towards her pussy, but she stopped me and looked at me.

"Can...can I suck on it?" She asked.

"Yes! Of course!" I said eagerly.

I laid flat on my back so that my cock stuck up in the air, high above the bed. She clambered between my legs and examined it, stroking it softly with a hand.

"It's still so big."

"Thanks. I'm flattered."

"Is this cum?" She asked, looking at the trickle of precum oozing from the head as she squeezed it gently.

"Nope, just precum!" I responded nervously.

"Oh!" She said, wiping it away with her finger and rubbing it to feel the consistency. She moved her head down; blonde curls falling forward. Ever so gently, she kissed the tip of my cock and then rested her lips on the head. Even that gentle sensation sent a wave of pleasure coursing through my body and I threw my head back, groaning. My ex had never wanted to suck my cock, but here was Taylor who was even more inexperienced but was eager and ready to try new things. I tucked her hair behind her ear, so that way I could watch what she was doing. She wrapped her lips further around my cock and began to take more of me into her talented mouth. She rocked up and down slowly, each time taking just a bit more of me between those pink lips. Inside she waggled her tongue around as she dragged her lips back and forth. I lay there, curling my toes and grunting out affirmations and she worked over my cock. Eventually she moved her lips down my shaft and in response I thrusted my hips up slightly, forcing more of me into her mouth. She coughed and pulled back to clear her throat.

"Sorry." I said dazedly. "It just felt so good, I couldn't help it."

"So, I was doing good?" She asked quizzically staring at my moistened shaft.

"Amazing." I said, staring back at her. "But I want something more. It's time to return the favor."

Her hand went to cover her pussy again.

"Down there?"

"Yes. You tasted me, now I want to taste you."

"I know about cunnilingus, but is that something a lot of guys do? None of them has ever asked me about that before. It's always been about what they want me to do to them."

"Only the good ones do."

"Ok...then."

We swapped positions and now Taylor was on her back and I positioned myself in-between her thighs, gently sliding my fingers along her smooth alabaster thighs. She trembled. I gently placed my lips against her damp pussy lips. Just that simple contact elicited a visible reaction. I kissed it again, pressing harder, this time probing ever so slightly with my tongue.

"Wow! That's a new feeling!" Taylor said blue eyes going wide.

"A good feeling?" I asked.

"Yes! Keep going!"

I was by no means an expert, but I did my best. I thrust my tongue deep into her folds, feeling her pubic hair tickle my nose, as I tasted her. I worked my lips, rubbing them against hers as I made licking motions with my tongue. She grabbed my head and ran fingers through my hair as she writhed beneath me. Pulling back slightly I popped one finger into my mouth and then placed it against her quivering lips. I slid it in slowly as I resumed my oral treatment. I got a particularly loud moan from that.