The Prom Date

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I shivered under her, "God." I breathed. "Good thing I brought this then huh?"

She took the condom from me and rose up over me. Her fingers deftly tearing the package open. "Get ready Jake, I'm going to make you a man." She took hold of my cock and rolled the condom down my girth in a couple of strokes. Then I was hard and ready to enter her. Anna of course, didn't keep me waiting. She shifted over me, and lined my cock to her waiting slit.

I watched eagerly, as she lowered herself down on me. I felt the warmth of her soft tunnel open u around me as she worked herself down. Anna moaned and I gasped, as her hips rested against mine. She was tight and hot, it was the most amazing thing I've ever felt. She rocked her hips back and forth and her walls began to rub and milk around me. I reached up and cupped her breasts and savored the way her body felt.

"Oh jesus Anna." I gasped.

She smiled and bounced on my lap. "You like that huh?" She teased, "Like it when I fuck you?"

"It's incredible."

She leaned down and kissed me, bobbing her hips up and down on my length faster. She worked me up and down, our tongues dancing with a furry and a need that had been building in both of us. I put my arms around her and rolled her over roughly which only made her laugh. "Oh Jake, getting frisky are you?"

I shook my head and I brushed the hair out of her face. "No Anna. I'm horny."

And I began to thrust into her, hard and fast. The bed screamed in protest, and Anna moaned in delight. Her legs hooked around my waist, which opened her wider for me and aloud me to push into her deeper, until I swear I was smashing against her cervix. I felt her fingers claw at my back and I swear I hear her hiss, "Jesus!" but it was drowned in her moans and my grunts.

I pushed into her hard and held still because I felt something pop. There was a wetness on my dick that wasn't there a second ago. I moved in and out a few times to check and I felt her wetness around me, a sensation that I didn't have a moment ago. Anna must have felt it too because she gasped and looked at me. "Jake, Jake hold on. I think the condom broke."

"Ah shit." I said and slid off of her. I watched as I slowly slid myself out of her. The tattered remains of the condom dangling off my dick uselessly. The part of my dick that has been bare inside of her was shimmering with her juices. My tip was dripping with my own pre-cum which I knew had been dripping inside of her too.

Anna rolled the ruined rubber off of me and sighed, "Well that sucks." She said, her finger rubbing over my tip and flicking the pre-cum away. "I hope you don't leak sperm in your pre-cum." She looked up at me with a wink.

I sighed and suggested, "I could go get more condoms."

She looked up at me and smiled, "You could." Then she laid back down. "Or you can put it back inside me and see what it really feels like."

I took a breath and my cock gave a jump. "Anna, I don't think that's a good idea is it? I mean you just said you might get pregnant."

She sat up again quickly and kissed me. "Listen Jake, you told me that you never fit in anywhere with people around school. Unaccepted, alone, that's no way to go through life. You are an amazing guy and you deserve something great. I believe that the greatest way a woman can ever accept any man, is to accept his seed." She laid back against and shifted closer to me until my tip touched her slit again. "Consider me accepting of you in every way. If you knock me up though...I'll just have to marry you or something." She smiled.

I rose up over her and pushed myself back into her. I laid on top of her and kissed her, "I can't thank you enough. You are amazing Anna." I told her. Her wetness gave me such a rush. It felt incredible without a condom. I could feel her walls and folds sliding along my shaft. I trembled each time I moved in and out of her, and I had to take a much slower pace or I was going to pop.

Anna moaned softly and smiled, "Does it better better inside me? You feel even harder in me now."

"It's, it's amazing." I panted. "My going to cum though. I'm sorry I can't hold it."

The pressure in my balls was incredible. The tingles raced through my shaft and I grunted.

"Go ahead Jake. Cum in me. Give me all of that giant load as deep as you want." she urged me.

I increased my pace a few final strokes. Then I was cumming and I cried out, "Anna!"

"Kendrick motherfucker!" She cried with me and moaned as my shaft spewed into her. I grunted and buried my face in her neck as my cock throbbed and pulsed waves of cum into her belly. "Christ that's a lot." She screamed, with pleasure.

Finally I finished, and rolled to the side, to catch my breath. Anna lay there with a hand on her stomach, like she could feel my cream, lathering around inside of her. "Wow! I've never been cummed in before." She told me.

I laughed and kissed her shoulder, "I've never cummed in anyone before. Was it good?"

She looked at me and laughed, "Was it good? I'm still cumming a bit right now. Christ."

I sighed and nodded, "Anna look, whatever happens. You know if you get pregnant, I'll do whatever you want me to do."

She patted my chest, "Oh don't worry too much about it. I am not a child Jake, and I can take care of myself. But that is very kind of you to offer."

I rolled onto my back and looked up at the ceiling. "So what happens now?"

She shifted onto her side and said, "We spend the night in each other's arms like boyfriend and girlfriend. Then tomorrow I'll take you home and I have to catch my flight."

I frowned and took a deep breath. "Yeah and then it's back to normal for me."

"I wouldn't be to sure about that. You put on a great show, and people will remember that you left the prom with me. You don't realize the impact that will have, trust me things will be different for you."

Anna was right about that. Things were definitely different. People cheered at me in the halls, Megan Malhony gave me her phone number, and she was like the hottest girl in school. Everyone wanted to know how my night with Anna Kendrick went. Of course I never told anyone the truth, that night stayed between me and Anna. I never did get a really girlfriend. Megan flirted with me but we never went anywhere with it.

Three months later i graduated I was sitting in my room like any other day. School was out forever, though I was exploring my college opportunities. In was a gloomy day at the end of June when my Mom called my name. I glanced out the window and saw a car in out driveway that I didn't recognize. With a sigh, I tossed my Xbox controller down and got up.

The front door was open as I headed downstairs. My mom was looking up at me with tears and I felt worry overwhelm me. A woman stood at the door with her back to me, as if she was taking in her surroundings. She was short, her hair brunette and beautiful and there was no way it was who I thought she was.

I stepped down off the last step of the stairs and said, "Anna?"

Anna Kendrick spun toward me smiling. But my breath caught in my chest when I saw the definite swell of pregnancy in her stomach. "Hi Jake." She said softly.

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16 Comments
AnonymousAnonymous4 months ago

What a delightful story of a young man losing his virginity. So sweet.

AnonymousAnonymousover 2 years ago

Please update

AnonymousAnonymousalmost 4 years ago

one of my all time favourite stories! read it for the fifth time now. thanks for that! any chance for a second part of the story?

AnonymousAnonymousabout 5 years ago
Well done!

Excellent writing and the story worked really well! It had a natural build to the intimacy that really works for Kendrick.

Kudos

AnonymousAnonymousover 5 years ago
Wow!

I loved the fact that this wasn’t another “so blah blah blah just happened to come to my town and I totally boned her though she had absolutely no reason to hive me the time of day” stories!

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