The Prom Date

She leaned in and gave me another gentle kiss, this time I tried to kiss her back. The kiss deepened before I realized it. I felt her tongue pushing into my mouth and felt her pressing her body closer to me. I put my hands on her hips and held her. When she slipped away from me I couldn't help but shiver.

"That's what I've been missing." I breathed softly.

Anna cupped her hand to my cheek and leaned her forehead against mine. "You have no idea." She whispered against my lips.

"I'd do anything to experience it all with you Anna." I told her.

She paused and took a breath, her head turned to look at the condom she had left on the bed. She reached over and picked it up, and pressed it into my hand. "Later." She said softly. Then backed away from me slowly, biting her lower lip.

Then she was gone and I let out a deep breath. What was happening? I couldn't believe how things were going with Anna right now. I mean I really think we almost really had sex just now. Something held her back, but whatever it is, I don't think it was a huge barrier to actually losing my damn cherry to the beautiful actress.

The prom was going to be an incredible experience after all.

Anna met me after school the day of the prom. A few hours before the prom actually began of course. Together we set up our stuff on stage and ran through some final ideas. When we were done she drove me home again so I could change for tonight. "I'll be back to get you at seven okay?"

I smiled, "Sounds amazing." I took her hand and gave it a squeeze before getting out of the car.

I showered, I scrubbed and I washed. I wanted to look my absolute best tonight. This could end up being the biggest night of my life. My mom rented me a tuxedo for prom, black with a white shirt and dark blue tie. I looked amazing in it. Anna was going to jump my bones when she sees me in this. Finally I used some cologne and before I left the room I grabbed that condom from last week off my table and tucked it into my jacket pocket. I still didn't think that Anna would go all the way with me, but I wanted to be safe and I was pretty confident that something sexy was going to happen tonight.

I don't know really. Things definitely heated up between Anna and I but I'm not sure how far she was willing to go. At first it was an act to give me some slack with my Mom, but that kiss in the bedroom certainly hadn't. My lack of any kind of girl experience had me clueless to what she wanted. The way I saw it was this, if I got to have sex with Anna Kendrick then great. But if nothing happened at all, and maybe Anna and I just have a few dances, a good show, and a drink or two. Even if that is all that we do, it will still be the best fucking night of my life.

I heard my Mom called my name and I glanced at the clock. Realizing it was seven I launched myself out of my room. I darted downstairs and stopped dead in my tracks as I caught sight of what waited for me in the doorway. Anna had dolled herself up incredibly. Her hair was full and fell around her face and shoulders and it just seemed to shimmer. She wore a tight black silk dress, strapless so the tops of her breasts and her shoulders were completely bare. There was very little to imagine to the shape of her amazing body.

The best part about it was that she was looking up at me with the most incredible smile. "Hey Handsome." She said.

"Hi." I said softly, stepped down the final steps. "You look incredible."

She stepped in with me and kissed me softly. "Come on tiger let's go put on a show."

As we left I think my Mom was about to explode. Anna and I snuck into the gymnasium before any of the students arrived so we could do one final check of the stage and make sure we had everything right. I couldn't help looking at Anna every chance I got. I was trying to be sneaky but she caught me more than once, but each time she caught me she only returned my looks with a warm smile.

Finally people started showing up for the prom. It was a lavish event as couples had their pictures taken at the door. A DJ played music while the crowd thicken. Meanwhile Anna and I hung out and joked backstage. The principal brought us a little punch and said that if we wanted our picture taken he would keep the booth open for us to get a shot after the show.

"I love punch." I said, sipping from my solo cup. "Tastes like diabetes."

Anna chuckled, "It tastes like punch to me. But whatever you say."

The principal came around the stage and said, "It's time guys, I'm go introduce you."

"Here we go. I'm fucking so nervous." I said setting the cup of punch down.

Anna stepped up to me and cupped my face in her hands. "You are gonna be great okay. If you get nervous you just look at me, watch me and pretend we are just in your room. That's it okay." She kissed me and moaned against my lips.

I smiled, "God I love kissing you."

Anna smiled, "I'm kinda fond of kissing you too." Then she patted my chest as her name came from the principal on stage. "Time to do this tiger." She winked and spun heading out on stage to the cheers of the school.

I grabbed my guitar and picked it up waiting for my que. Anna greeted the crowd shouting, "What's up Portland High!?" She laughed and cheered with the promgoers. "Are you all ready to have a good time tonight?"

Then she started the cup thing. Why that shit was so popular was beyond me, but our version was going to blow people's minds. I listened as Anna started to sing, then she paused mid-verse and said, "Portland High, please welcome your one and only Jake Cooper on guitar, and my prom date tonight."

I step out to a cheering and murmuring crowd. I started played a guitar solo to match the beats Anna did with the cups. As I bleed the solo back into the chords of the song, Anna resumes singing. "Cups" goes smoothly and we head directly into "Bring Me to Life". I step on my distortion and relax as I get to play a song I'm pretty familiar with. The crowd cheers as we kick off and start rocking the house. I can't believe how well we go together, I even stepped up and did the fucking rap part with Anna and I could tell that part surprised her.

We ended on a big finisher "Hit Me With Your Best Shot" and man the crowd loved it. When we finished, "Give it up one more time for Jake Cooper on the guitar!" She cried. I got a big cheer and start shredding a guitar solo, just for the sake of showing off. Then it was over and we headed backstage where I dropped off the guitar and spun toward Anna who pounced on me.

"Jake you were incredible!" She cried throwing her arms around me. Then she was kissing me and I just gave into it. The relief of how great that went just had me so relaxed I couldn't stand it. I held Anna and kissed her back as best I could. Our tongues danced, and we tasted each other, it was amazing.

I set her down and I gestured to the dance floor where the DJ had resumed the party. "My dear, I believe our prom awaits."

She smiled and took my arm. "Let's do this shit."

Together we walked out onto the dance floor and almost immediately got bombarded with people. They nearly overwhelmed us, asking questions and wanted pictures with Anna. Despite my performance, her fame simply over took all of it and I found myself stepping away and letting her do her thing.

I went to the punch bowl and grabbed a drink and a couple of crackers. Then I felt arms wrap around my waist and a warm soft body press against my back. Anna laid her head on my shoulder and said, "I'm sorry. I couldn't beat them back. Vultures."

I smiled and shook my head, "It's fine. Cracker?" I asked holding a cracker back to her mouth, she opened and I gave her the cracker. Then I spun while she still held onto to me and our bodies pressed together. "You are an amazing woman Anna."

She smiled and sighed, "You are pretty great yourself Mister Cooper."

I winced, "Oh way to make me feel old. Mister Cooper. Geez."

"Oh fine. Jake whatever you say." She patted my chest. "Come on Jake, dance with me." She backed away from me but held onto my hands to pull me out onto the dance floor with her.

"Oh man, I dance like a spaz." I confessed.

Anna laughed and started to sway and move to the beat of the music. "Me too, who cares?"

We danced although it took me a couple of songs to relax into it a bit. Then we really started to move together. Our bodies bumped and I would be lying if I said there wasn't a little bit of grinding. Anna would turn away from me and rub her ass against my crotch, with an arch of her back. She would flick her hair over her shoulder to smile back at me, like she knew she was rubbing her ass against my cock the whole time and she wanted it.

When the tempo changed and it was time for a slow song, Anna turned and stepped lightly into my arms. She put her arms around my neck and my hands rested on her hips. She smiled up into my eyes as we swayed. I flexed my fingers against her hips, just happy to be touching her.

She let go of my neck for a second and reached down to take my hands off her hips. I thought I was in trouble but she pulled my hands around behind her and had me cup her tight ass. Oh there is nothing like cupped a girls ass. Wow, and Anna's ass was incredible.

"Since you like squeezing so much." She teased as she put her arms back around me.

I smiled, "It's just what I always wanted for Christmas."

"I'll bet." She laughed, "Except it's not Christmas."

"Close enough for me. Early presents and all."

"Oh early presents is it?"

I shrugged, and squeezed her ass hard enough to get a squeal out of her. "Oh she likes that I think." I smiled.

Anna laughed and bumped herself against me. "I know I like that. And I like you. And I think...." She paused and bit her lip.

I frowned, "What is it Anna?"

She sighed and said, "Look I like you a lot Jake. I do, and I know that's like really weird because I barely met you and everything and God you're still in fucking high school so I have no right." She stopped and shook her head, "I want to, I really do. I just don't want to do it and then just leave you or expect you to wait for me or something."

A lot of information was kind of coming at me fast. "Anna, Anna, Anna, it's okay." I told her moving my hand to brush a single tear that had started to roll down her cheek. "I gotta be honest with you. I have had a thing for you for a while. I know movie characters are not who you are, but I watch you on talk shows when you are just being you. You are awesome, and for some strange reason you are the only girl that ever gave me any kind of chance. I can't even begin to tell you how much that means." I leaned forward and pressed my forehead to hers, "I have never had a girlfriend, but in my dreams the girl that is always in my arms every night is you."

I moved back and looked at her. Her eyes still watered and she ran her hands back and forth on my shoulders. Then without another word she leaned back in and kissed me again. We swayed and we kissed, my hands coming up from her butt to hold her like a man should hold a woman. Her hands cupped my face, holding me against he so I couldn't pull away from her lips.

Finally we broke apart enough to get our breaths. We stood for a moment panting and smiling at each other. "What time does your mom want you home?" She asked.

I shrugged, "Who cares? She can worry. Let her imagine all the bad influences you're putting upon me."

Anna nudged my ribs, "You say that, but will have you know that I fully, FULLY, intend to corrupt the shit out of you."

I scoffed, and said, "You can try lady."

Anna tugged me against her by my tuxedo jacket and kissed me again. "Be careful what you wish for Jake. Come on. Let's go back to my hotel room and I'll teach you the ins and outs." She winked at me and I knew that in that moment I was not going to be a virgin after tonight.

So we snuck away from the prom, forgetting about taking a photo at the booth. We darted to her car giggling like two kids about to go do something very naughty. In a way I guess we were. I mean I'm only eighteen as of a month ago, and Anna was only twenty-six so still young right?

The drive to the hotel was kind of quiet. We didn't talk, but we held hands the whole way there. The closer to the hotel I got the more nervous I became. I didn't know how to have sex. I've only seen it in porno. Besides how would I keep my cool when I saw Anna naked? I had no idea the proper behavior. What if I embarrassed myself? Or what if she thought my dick was tiny and laughable.

She parked us in front of her room on the ground floor of the Motel 6 that was the meca of travel in Portland. With eighteen rooms, this hotel was a place. Okay it was a shit box, but it was OUR shitbox and apparently the place where my virginity was going to die.

Anna opened the room and slipped inside to turn on the lights. I followed her slowly, shutting the door behind me and flipping the locking latch. Anna came around and smiled at me. She walked up to me and smiled, "Unzip me?"

She spun and reached back to lift up her hair so I could get to the zipper. I took a deep breath and reached for her zipper. I fumbled with it for a moment, my hands were shaking. I think I heard Anna giggling. I got a hold of the zipper and hesitated for just a moment, before slipping the zipper down. The dress went slack around her body and it parted around the zipper momentarily allowing me glimpses of her bare back.

Her hair fell and she stepped away from me. She smiled and asked, "Are you ready?"

I swallowed and took a breath. "I'm so nervous."

"Well maybe I can bring a smile to your face." She shrugged her shoulders and the dress fell to the floor. Then she was naked before me, though she faced away from me still and I got to see her wonderful curves and firm tight ass. I felt the blood rush from my body directly into my cock.

"Oh dear god." I breathed.

She chuckled and turned toward me, revealing her glorious body to me. Her breasts, her stomach, the puff of her perfect little pussy lips, all of it live and in person before my eyes, it was all incredible and I stood there like a stupid ass just staring.

Anna raised her eyebrows and stepped closer, "Is that it? Just gonna stare and drool?" She took my hand and placed it to her breast. "Or maybe you might wanna touch. Anywhere you want." Her breast felt soft, yet warm and lovely in my hand. I glanced down as I let my hand rub over her. She closed her eyes and savored my touch, arching her back she pressed her chest against my touch.

"You like the way I feel?" She asked.

I nodded, "You're incredible. Beautiful."

She smiled and cupped my cheek, "You make a girl feel wonderful."

I licked my lips softly. "I try."

"We can't do anything else with your clothes on too." She slid her hands into my jacket and forced it off my shoulders. Then her hands worked on my tie, I let her breast go and helped her take it off. As I worked the buttons of my shirt off she reached down and unfastened my pants. Her eyes dipped down and I knew she could see the bludge that had formed. "I hope that's for me." She teased.

"All for you Anna." I said.

I peeled my shirt off at the same time my pants fell. Anna looked up at me, locking our eyes together as she slowly dropped to her knees before me. I trembled with anticipation and need. I never thought I could want a woman as badly as I wanted Anna right now. Not that I had experience with that.

She looked up at me and reached up slowly to hook her fingers around the waistband of my boxers. The tent nearly bulged against her face from how hard I was. I took a breath as her fingers hooked and tugged my boxers down around my ankles in one motion. It was like it all happened in slow motion, she looked up and I swear her eyes widened as she caught a glimpse of me.

"Wow someone is happy to see me." She said with a chuckle as her fingers softly wrapped around me. I shivered at her touch, my cock throbbed in her grasp. "Oh was it something I said? I barely touched you." She giggled.

I blushed and shook my head, "I'm sorry."

Anna looked up at me, "I'm gonna suck it. Okay?"

I let out a long breath, "Okay."

Then she did. Her mouth opened up and her soft, warm lips wrapped around my tip. I let out a moan as she mouth slid down my cock. I fell her tongue lapping around the underside of my shaft, "Holy Christ!" I gasped and my hands went to her head, gripping her hair.

She chuckled on my shaft and bobbed her head. She would suck in her cheeks and let them slide back along me shaft when she pulled me out, but lapped her tongue around me length when she took my length back in. And such was the rhythm she built, each time my cock surged with the urge to cum, I gripped her hair out of reflex and I held it back by some miracle.

After a few minutes she pulled away from my shaft. She eyed my tip and saw a bit of pre-cum leaking from my tip and licked it off with the tip of her tongue. "You know what I want?" She asked lifting my shaft with her hands so she could give gentle little kisses on my balls. I gasped and my cock surged in her hand. "I want to drink your cum."

She opened her mouth and was about to put me back in when I just popped. She coughed as a burst of sperm blasted into her open mouth. The shock surprised her enough that she fell back, cum dribbling from her lips down onto her chest. My orgasm wasn't through either and my cock was unrelentingly squirting ropes of cum at her. I watched it splatter on her chest and belly. I tumbling onto my ass as my pleasure faded and I sat there panting with breath and watching in horror as Anna sat there in a cum covered shock.

I watched in fear as Anna looked at herself over. She ran her fingers over her body and wiped up thick globs of my seed with her fingers. She held up a hand with sticky strings of goo between her fingers. "Holy shit Jake." She gasped, licking a bit of my cum off her chin. "I've never seen someone cum so much, do you even jack off?" She asked.

I blushed and nodded, "I do. But that was unlike anything I ever experienced before. Anna that was ridiculous."

She got back on her knees, and loomed over me. "Well I need to feel that inside me next. But first," She ran a hand through the cum on her tits. "Let me go wash this off. Wouldn't wanna get any inside me on accident now would I?" She winked and got to her feet. Then darted off into the bathroom.

I sat there in disbelief and looked down at my dripping dick. I've only had a taste of what it was like to have sex, and in a few minutes it would be time to perform again. I sighed and looked around for my jacket. I kicked off the boxers and had a sudden brilliant idea to be naked on the bed waiting for her with the condom from my jacket.

I used my boxers to wipe my dick clean and leapt onto the bed. I propped my back up with pillows the condom between my fingers. I looked up as I heard the shower shut off and I watched the bathroom door, waiting for Anna to reappear. I couldn't help the smile on my face as the door opened.

Although Anna pretty much set herself up to wipe that smile off my face real fucking quick. She stood in the doorway, her hair wet and heavy around her shoulders, a sexy smirk on her face. "Hey there."

I smiled back as I felt the blood rushing back into my member. "Hey yourself, beautiful." I held up the condom wrapper like a card. "Look what I brought."

She slid over to the bed and crawled over me. "That was very thoughtful." She said, moving over me and kissing me gently. She laid her body on top of mine, my cock hardening against her stomach. "You know I wasn't really thinking about that when I started tonight. I figured I was just going to let you cum inside me. But after seeing that load you just blew, I don't know if i can keep from getting pregnant."