Band One Shots & Weird Shit

Awkward Date X Ash Costello*

"Look, you've been on the dating scene for way too long now. You need to find someone already." My friend Lexi said, taking a sip of her coffee. "Why do you care so much?" I asked. "To be honest, it's because I placed a bet on you. I don't wanna pay Carly ten bucks." Lexi replied. "Seriously?" I asked.

"I admit, that sounded terrible. However, I'm friends with another hopeless romantic. Her name is Ashley, and I'm setting you up with tonight." Lexi said. I sighed, "I hope she's cool." I replied, taking a final sip of my coffee.
-
I spent the next hour getting ready, trying on my entire closet. I finally settled on a floral mini dress with converse. I grabbed my phone and keys and drove to where we were meeting up for dinner.

"Hey! I'm Gwen, you must be Ashley," I said, approaching a woman with red and black hair. "Guilty as charged, and you can call me Ash." She said, leaving in for a hug. We talked for a few minutes while we put our food orders in.

"So, what do you do for a living?" I asked. "I'm actually a musician in a rock band. My band is called New Years Day, and I'm actually about to leave on tour." She answered. "What about you?" Ash asked. "I just work in an office. Could you tell me more about touring? I'd love to here about it!" I replied, seeing our waiter bring our food.

Ash nodded, "It's honestly the best thing! I've met so many cool people and fans. I'm grateful for having this opportunity to connect with people everyday." She said, a glimmer in her eye. She told me some more tour stories and about festivals she's played. I couldn't stop laughing over the stories she told, especially the ones about pranking her bandmates.

"Do you wanna go back to my place?" I asked, holding the door for her as she walked out into the street. "Sure," she said, grinning. I opened her car door and got in. "Since I now have you trapped, it's probably a good moment to let you know that I've never been with a woman before. I'm apologizing now because I have a feeling I'm gonna fuck this up somehow." I admitted, switching onto the highway.

"I honestly wouldn't have been able to tell otherwise. You showed no signs of anxiety when we were in the restaurant. I wish I was as confident as you are right now when I first got with women," Ash said, squeezing my hand for comfort. I smiled at the gesture.

We drove for a few more minutes in silence. I took some deep breaths through my nose to steady my racing heartbeat. We walked up a flight of stairs to apartment and I opened the door. I wiped my sweaty palms on my dress.

"This is really cute! Needs more crystals though," Ash remarked, circling my living room. I sat down on the couch, Ash joining me a few moments later.

"Gwen, I want you to kiss me."

I did just that. Kissing her reminded me of when I was younger having my first kiss. It was awkward, filled with groping, but wild passion too. This felt a bit more normal as my hands roamed all over her. I lifted her shirt off gently, careful not to get it caught in her delicate lace bra. She didn't care, ripping off the rest of my clothes. Both of our breathing became frantic as we undressed each other.

"What you're about to feel is probably going to be uncomfortable at first, as long as you're calm, it'll start to feel good. Now close your eyes," Ash said seductively. I did what I was told, gasping as she inserted herself in me.

Ash began to thrust her fingers harder, kissing all over my neck and collarbones. I moaned softly, paranoid of my nosy neighbors. She put her thumb over my clit, rubbing in small circles. "Fuck!" I moaned loudly, feeling myself tighten around her fingers.

My hips thrusted as I climaxed; I fell back onto the mattress, drenched with sweat. I took a few deep breaths in an attempt to calm my racing heartbeat. "I may be inexperienced, but I know I can make you feel good." I said, turning to face Ash on my bed. "Prove it."

I immediately straddled her, kissing her with intense passion. I made a trail of kisses as I moved further down, stopping right in front of her core. I continued to do the same on both of her inner thighs, driving her wild. Ash was getting impatient, so I went in for the kill.

I put my tongue inside her and moved it with circular motions while also rubbing her clit. "Gwen, I'm so close-" She moaned, clenching around me. "I love when you moan my name," I whispered in her ear, thrusting my fingers into her. She climaxed, moaning loudly while doing so. So much for worrying about the neighbors.

She laid on my bed, moving her sweaty hair that was plastered on her body. "For someone who claims to be inexperienced, you certainly have it down. If you need someone to practice your skills on, just call me." Ash said, kissing me passionately. "I'll take you up on that," I said, pulling the covers over us.