Hailees Birthday

Hailee's Birthday

(The events in this story are a complete work of fiction and should not be treated as fact)

Hailee Steinfeld and I have been close friends since we were in high school together. Growing up, I had a crush on her but like a typical boy whose best friends with a girl and is way too nervous to be honest about his feelings, I held in my crush and never told her. If I'm being honest, I was just happy to have her in my life. She had been such a great person to talk to and have fun with, I just wish there was a moment in time where we dated.

After high school ended, we went our separate ways but always tried our best to stay in touch. But as she has gotten more and more famous, the less we've talked. I've tried to move on from my crush on her, but I never could. I dated some women, and some relationships lasted awhile, but I never felt as loved as I did with Hailee. The only action with Hailee I had ever gotten was jerking off to her photos she'd post. It made me feel guilty, but it felt good.

To my surprise, I found out she was back in town for a while, and I had recently gotten an invitation to her birthday party at her house. And I knew I had to take this opportunity to tell her how I've felt all these years.

It was December 11

th

, Hailee's birthday and I showed up to her house with a gift, dressed somewhat well. And I obviously showed up a tiny bit early in excitement. I rang her doorbell and anxiously waited to see her again.

"Oh my god, Tony!" she said as she opened the door and hugged me. "It's been so long, I've missed you!"

"I know Hailee, it's been too long. I've missed you too." I said as her body pressed against mine. I'd be lying if I said I didn't get slightly hard seeing my crush in person for the first time in years. She looked incredible. She wore a leather jacket with a blue shirt underneath and a black skirt on with some heels on. She looked so sexy and beautiful.

She took my hand and led me in and had me put my gift for her on the table with the others. I saw plenty of our friends from high school and felt a sense of nostalgia seeing everyone again. But no one had me as excited and nostalgic as Hailee did.

"Tony, you should meet up with everyone again. I gotta still help the others with the food and everything. I'll talk to you later." She said as she left to help set up with her party.

The party went on and while it was nice to see old friends again, it bummed and bored me that I couldn't see Hailee and tell her how I felt due to her business. I left the main party area the sit on the stairs in front of the front door, looking through my phone waiting for something interesting to happen. All I heard for over ten minutes was the music on the speakers blaring, until I heard a familiar voice.

"Damn, I didn't think you'd look so bored." Hailee said as she came out of the kitchen.

"No Hailee, I'm not bored. It's great seeing everyone again, it really is. Please don't think that I'm really happy to see you again." I said to hopefully reassure her.

Hailee moved towards me and sat next to me on the stairs. "So, why are you sitting out here and not out there with everyone." The way she said that made it seem like she was empathizing with me. Had she been bored too?

"I don't know, I guess I could've seen our old friends whenever. But you Hailee. I haven't seen you in years. It's been impossible." I said that and I looked in her eyes and could tell she was a bit upset about this. "I'm not blaming you; I get it. You're famous. I just wish we could see each other more often."

"I know Tony, I wish we could. You were always my best friend." She said as she hugged me and kissed me on the cheek to my surprise.

"Hailee, I gotta tell you something important..." I stopped as I looked at her, waiting for the confidence to come. But it didn't. "The gift I got you isn't that great. I got the invitation last second and I got you something shitty."

"Oh Tony, whatever you got me is perfectly fine. No gift would've been fine. Just seeing you is a great gift." I blushed after she said that. "You know Tony, I'm glad you came to my party."

I smiled and said "I am too. It's great to see you." We were both keeping eye contact.

"I'm sure it'll get fun down here with our friends. But I think we'd have a bit more fun upstairs in my bedroom." She said with a blush on her face.

I couldn't tell if I was dreaming. Did she just say that? No way she could mean what I think she means.

"Hailee, what do you mean?" I said nervously as I was still in excited disbelief of this situation and figured that there was no way this was happening.

She moved closer to me and said "The music down hear is loud, no one would hear us." She pushed her head towards mine and kissed me on the lips and we started making out. What the actual fuck was happening?

I moved back and said "Holy shit Hailee. I mean... I..." I was at a loss for words.

"Wanna come upstairs and give the birthday girl a special present?" She said as she kissed me again and giggled waiting for words to pour out of my mouth.

"Fuck yes Hailee. Let's go!" I said as I picked her up which got a gasp out of her. I carried her upstairs and found her bedroom door and we both landed on the bed and started making out. Her cherry lip gloss tasted incredible as I started removing her jacket and she started removing my pants.

"My god, you're already hard." She removed my pants with my help, and she reached to yank my underwear down and my cock fell out in front of her. "My god, I didn't know my best friend had such a big cock.

I chuckled as she said that as I thought I was a bit average, but I guess I impressed her. I laid on my back as she climbed on top of me. She placed her hand around my cock and started lightly stroking which made me moan.

"Ohh fuck Hailee." I blurted out.

She giggled and said "I haven't even stuck it in my mouth yet and you're already moaning my name? I'm gonna make you weak for me."

I moaned and gained some confidence to say "I've wanted this for so fucking long Hailee, you have no idea." She ignored me and put the tip of my cock in her mouth which made me close my eyes and moan.

She knew how to tease and suck a cock perfectly. She was better than all my exes and it was amazing seeing Hailee fucking Steinfeld sucking my cock and looking up at me with those beautiful eyes of hers. She started sucking more and more of me until my entire cock was deepthroated by her. She could tell I was loving it and made it better by bobbing her head up and down on my cock.

"Jesus... don't stop Hailee." I moaned and I felt her mouth perfectly doing work and blowing me. I started thrusting a bit into her mouth which made her chuckle while I was still in her mouth.

All she could let out was "Mmmmmmmm." She didn't dare stop, she loved making me feel incredible. As she kept doing it, I felt myself getting closer and closer to the edge. She took her mouth off of my cock to say "I can't wait to feel you inside me." And she continued to suck me. After she said this, I was so close.

"Oh God. Oh, fuck Hailee... Hailee." I was breathing fast and barely keeping a grip. It felt too good. Her mouth skills were incredible, and I couldn't contain myself. "Hailee, I'm... I'm..." and I lost it.

I exploded in her mouth which made her widen her eyes and look back up at me. I was shaking as I came into her mouth. I expected her to get off in disgust, but she kept sucking my cock which only made me bust even harder. She swallowed every drop. I moaned so loud but knew no one downstairs could hear us as the music was blaring.

She eventually got off and I immediately said "Oh shit Hailee. I'm sorry. I couldn't control myself. Shit. I ruined this. I just-"

She cut me off by saying "Tony, you really think I haven't made a guy cum early before?" She chuckled as she said this. "You didn't ruin anything. Plus, I doubt your dick will go soft as you eat me out."

I gasped which caused her to laugh. Her reaction made me want to take a bit of control as she did when she blew me. "I want you to lay on your back. Now." I said in a serious tone.

She blushed as she got down and spread her legs, revealing she had not been wearing panties under her skirt. My jaw dropped which caused her to say "Oh relax, all my clothes are in the wash. I had no clean underwear!"

I didn't bother to reply as I just wanted to taste her so bad. I immediately started kissing her legs upwards, leading to her pussy until I finally got there and started rubbing her clit with my thumb.

"Yes Tony." She moaned. "I wanna feel your tongue. I want it." I listened to her and slowly put my tongue inside her pussy which caused her thighs to tighten around my head.

"Damn Hailee, you're already wet." I said as I felt her wet pussy all over my tongue.

This caused her to groan and say "I'm just so excited. I haven't been with a guy in a while. Please Tony, just keep going."

I did as she said and started licking the inside of her pussy in all directions my tongue could go. She was still fully clothed but feeling her skirt over my head made it feel sexier. I took my tongue out and started fingering her. "You like that Hailee?" I whispered.

"Mmmmmm." Was all she could let out.

I pulled my finger out and sarcastically said "I guess you don't like it." Which caused her to immediately grab my fingers which were just in her pussy and shoved them in her mouth. "Holy shit Hailee. You dirty girl."

"Don't tease me Tony, please. I want your cock inside me." She blurted as she started removing her clothing. She took off everything and got into a doggystyle position with her ass facing me. I immediately stuck my face in and started licking her pussy again which made her moan again. "Yes Tony... Mmmmm."

I put my hands on her ass and squeezed, loving her soft it felt. While still tongue-fucking her, I spanked her right ass cheek which made her simply moan "Harder." I spanked her left even harder and kept spanking her, realizing that she doesn't mind getting a little kinky. I decided to be ballsy, and I lifted my face up and stuck my tongue in her ass which made her scream "Oh fuck! Tony!"

I pulled out my tongue and nervously replied with "I'm sorry, I just thought... I don't know."

She looked back at me and said "Why did you stop?" which got my cock even harder than it already was and I stuck my tongue back inside of her tight little asshole and swirled around, making her moan loudly. "Fuck! No guy has ever done this to me. Keep going!" and I did. I kept eating her ass for a bit before I decided it was finally time.

"Hailee, I wanna fuck you." I told her as I started to get my dick in position to fuck her from behind before something came to mind. "Oh shit, I don't have a condom. I didn't think I'd need one today."

"It's fine Tony. I really want you inside me. Please." She said as she looked back and smiled. This made me worry no longer as I got behind her and slowly inserted my cock into her pussy.

My head slowly entered as the rest of my shaft did. I said "God, you're so fucking tight Hailee." I started slowly rocking my hips back and forth. I chuckled and started thrusting to the beat of the song playing downstairs which caused both of us to laugh. "Did you ever think your old best friend would be stretching you out today?"

She laughed and moaned "No, but I'm glad it's happening. Also, you were always my best friend. I never forgot about you." I began fucking her a bit faster which caused her to stick her face into her pillow which caused her to scream a muffled "Holy shit!" as she clenched her fists into the blankets as I fucked her from behind.

"God, you have no idea how many times I've thought about this Hailee." I blurted out as I continued to fuck her.

She lifted up her head and moaned back "Well, I think I've always known. You need to stop accidentally liking old posts of mine while you jerk off." Which caused me to stop.

"Woah. No. I wasn't jerking off, I was just-" I nervously spoke as I was interrupted.

"Tony it's fine. Your dick is inside me. You really think I care you did that?" She said as she moved her ass backwards onto my cock which made me start thrusting back into her. "Besides, it made me blush." She quietly moaned as I started fucking her fast again.

I moaned with fast breathing as I slapped her ass and said "You like getting fucked by your best friend."

"Yes! Yes! Keep fucking me!" She moaned as I noticed her begin to shake like I did when I was about to cum. I stuck my arm around and started rubbing her clit as I fucked her hard. "Oh fuck! I'm gonna cum Tony. All over that fucking dick!"

I fucked even harder and whispered "Cum Hailee, cum." And I felt her climax all over my cock. Feeling all her cum squirt onto my cock and run down my thighs. She stuck her face in the pillow and all I could hear as she came was muffled moans of "OH!" and "FUCK!" and I maybe heard her yell my name, but it was hard to tell. We both slowed down, and she looked back and said "I wanna make you cum again Tony."

"I'd like that as well Hailee." I chuckled. She got onto her back, and she lifted her legs up onto my shoulders so I could fuck her in missionary. I took this opportunity to squeeze her tits and kiss them as well, licking her nipples. I wanted to be classy, so I said "Ms. Steinfeld, you have amazing breasts."

She laughed at me and said "Breasts? Come on, they're tits. Don't be nervous." She said as she blushed and pulled me in for a kiss and whispered in my ear "I'm on the pill. That's why you don't need a condom."

I pulled my head back and looked her in the eyes with shock. "Do you mean..."

"Yes Tony. You know what I mean." She said with a blush.

I kissed her on the lips before pulling back and getting my cock lined up with her pussy before shoving it in again which caused us both to moan. Since she was stretched out, I didn't waste any time and began fucking at a fast rate knowing how this was all going to end.

"Come on Tony, don't fucking stop!" She said as I kept going. I felt her legs wrap around me as I thrusted inside her harder and harder each time, filling her pussy up with my cock. "Oh god Tony! Yes! I need you!"

"I need you too Hailee." I blurted out as I kept going and I could feel myself getting weaker and weaker with each thrust, getting closer and closer to the end.

She put her hand on my face and pulled me in to kiss her. I pulled my head back, but she kept her hands on my head as we made eye contact the whole time. Even as we fucked, we never broke eye contact. "I want you to look at me when you cum inside me. I wanna see you lose control. Please Tony, cum inside me."

Her telling me this only made me get closer to climax. The thrusting, her bouncing tits, her legs wrapped around me were all amazing. But looking into those eyes of hers. Those beautiful eyes looking back at me as I was about to cum inside her, Hailee Steinfeld. The girl I've had a crush on for years upon years. All these years we haven't seen each other, and here I am fucking the most beautiful girl in the world.

"Oh Hailee, I'm about to cum." I said as my breath shortened and my mouth wouldn't close.

"Come on baby. Cum inside me." She said and that was it. After she moaned that, it was game over.

I moaned loud as I shot my cum inside of her, making her already warm pussy even warmer with my load. The orgasm I had was incredible. All I could moan as I came was "Hailee... I love you."

To which she replied "I love you too." I kept shooting ropes of mine inside her for a good twenty second before my orgasm finally climaxed and I got out of her and laid next to her on the bed.

I looked over at her and said "Hailee, that was the greatest I've ever had." I kissed her on the lips which caused us to make out for some time.

After we stopped, she got up and cleaned her pussy with all of my cum inside of it and came back to lay next to me. "So..." She started "I have something to admit."

I looked at her with a confused expression. "What is it Hailee?"

She blushed before saying "Tony, I knew you liked me. I could tell as we grew up. The way you'd look at me. The number of times you helped me out when no one else would. The accidental liking of my old posts while you jerked yourself!" She finished with a chuckle.

"Hailee, come on. I..." I couldn't even continue. We just had sex. I had to tell her how I felt. "Yes. I've liked you for so long Hailee. I've had this crush on you for years and I've wanted to tell you for so long."

She blushed and said "Well... if I have to be honest. I've always sorta liked you back."

I sat up and looked at her in shock "What!?" was all I could speak.

She sat up next to me and said "I liked you too. But I never wanted to hurt our friendship, especially back then. I was always nervous that we were going to end up like most of our friends who dated and broke up and ruined their friendships. I didn't want that for us." She looked upset as it seemed like we both had a great time now and possibly missed out on years of dating.

I wanted to express to her that it was okay. "Hailee. I understand why you felt that way. And I know that maybe back then things might've ended shitty. But we're adults now and we just did very adult things." I said as we both laughed. "And if this is a one-time thing then I'm okay with just staying friends. If you still worry about that, I'm okay. I just want you to choose what you think is best."

We sat in silence as we both reflected on what had happened. Eventually, she smiled and looked at me as she said "Thank you so much for your gift."

I was confused yet again and replied with "What gift Hailee? My stupid gift is downstairs."

She rolled her eyes and said "No, the gift you just gave me." She blushed.

I looked at her and thought about everything that had just happened and what she could be referring to. And all I could think to say was "The creampie?"

This caused her to erupt in laughter which caused me to blush and chuckle. She calmed her laughing down and wrapped her arms around my back and pulled me close. "No silly, you gave me the gift of a new boyfriend."

I had that confused look for a second before it hit me, and I looked at her with joy in my eyes and smiled. "Hailee, do you... is this happening?"

She blushed and said "Yes. Fuck it. We're adults now and I think we'll be fine. I know I'm busy a lot but now that we're out of school, maybe you can come with me wherever I go to film movies. I want you by my side. I've missed you all these years. I just want you in my life Tony. I love you."

I smiled and admittedly got a little emotional as I said "I love you too." I pulled her in for another kiss as we passionately made out and felt each other's naked bodies pressing up and embracing this incredible moment.

She stopped and said "By the way, I can't wait to have sex again. But let's go on a date before we do it again next time. Deal?"

"Deal." I said as we kissed again and started getting dressed. "It's so weird hearing my best friend saying we should go on a date before we fuck though." I chuckled.

She pulled my fully clothed body close and said "I'm your girlfriend and your best friend. It's normal to say those things now."

We both smiled and headed back downstairs into the party, holding hands and showing off to our old friends that we were in fact now a couple. I saw some shocked faces from our friends as I'm sure some of them saw us go upstairs and probably can guess what we did in her bedroom.

We sat down on the couch and held each other close. I wasn't sure what was going to happen next. What our first official date was going to be, what our next sex will be like, or how we'll manage seeing each other with her busy schedule. But I don't have to worry about that. I was sitting next to my best friend, who was now my girlfriend, and she looks so beautiful. Whatever happens next, I'm glad that I have her by my side.