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My First Time With My Best Friend Jackie

Where a two best friends realize how much they both wanted each other.
Hey this is my first story so please don't be harsh. thank you :)

Also none of this story is real, it is completely fictional. Thank you once again :)

To start things off, my name is Chase. I am 16, and a sophomore in High School. I've had a lot of harsh times throughout my lifetime, including constant bullying throughout middle school, but I pushed through and made it through. That's when I met Jackie.

Jackie and I met in history class, freshman year. I was very shy and had a lot of trouble meeting new people, but she was one of those outgoing girls. She came up to greet me with a hug and I was very happy when I met her.

Throughout freshman year, she introduced me to tons of people and with her, along with joining the lacrosse team, I actually became pretty popular (although I hate using that word). This remained constant throughout the whole year and Jackie and I became closer and closer. Unfortunately, I never got to see her throughout the entire summer, but, I still had lots of fun over the summer (non-sexual fun that is).

Sophomore year came I was so excited to see all of my friends. I hugged and bro-hugged everyone who I remembered and even some that I didn't. Finally, about twenty minutes before the bell rang, I saw Jackie. I had never really thought of Jackie in a sexual way, although I did notice her stunning beauty constantly. That is, until now.

She was wearing an extremely revealing blue and white shirt, along with a miniskirt that I could barely see she was wearing it was so short. She didn't notice but I stared at her like none other. She came up and gave me a hug that sent jolts through my spine.

"Oh my god, Chase, you got so buff!" she said as I was hugging her. I don't like to brag a lot but at this point I had to show her the large muscles I acquired over the summer of hard training.

"Jeez, Chase, that's so hot!" She said. I blushed a little. Although she didn't say anything, I could tell she noticed.

"You look Gorgeous Jackie!" I said.

"Pfft, not really" she said as I could tell she wanted me to compliment her more.

"Jackie you are definitely one of the hottest girls at the school, don't even lie to yourself." I said with a huge smile at her face. I couldn't help it but I continually stole peeks of her very large 36C cup breasts. She didn't seem to notice though.

"Hey it looks like we have chemistry together so I'll talk to you then okay? I need to find my guidance counselor" She said.

"Alright, can't wait!" I said, thinking about what kind of things she wanted to talk about.

For the rest of the day, all I could think about was Jackie. I could not believe how gorgeous she looked. Some of my teachers even noticed me staring into random places, so I had some trouble getting to know my teachers that day.

Finally, It's 6th hour, Chemistry. I open the brown wooden door to see Jackie talking to one of her friends. She was laughing and smiling and when she and her friend saw me, her friend immediately whispered into her ear. The only thing I could make out was, "Is that the guy?"

"Hey Jackie" I said, not knowing what to say.

"Hey, sit with me in the back, I want to catch up with you and everything that's been going on!" she said.

"Sounds perfect to me" I said with a big smile. During the entire class we simply talked about everything we did over the break. She went to the Bahamas which wasn't very surprising since she had a perfect golden tan all over her body. She also apparently met a boyfriend who she ended up breaking up with before summer ended.

"So did you two umm..." I stumbled.

"Have sex? well of course silly we went out for a solid 3 months with no parents around!" she said. I immediately was turned on by this. Luckily I was sitting down.

We talked for a bit more and finally at the end she said, "Hey so do you wanna come hang out at my house tonight? My mom said she might be going out and she's really overprotective, as you know of course." She said in a teasing tone.

"Yeah that sounds, erm, wonderful. See you at six?"

"See you at six."

It was six o'clock and I told my mom I was going out to study with a friend. Little did I know that I would be doing a lot more than studying.

I knocked on the door, and Jackie answered.

"Hey come in, come in!" she said. "My parents just left so we have a couple hours to do whatever." I couldn't help but notice that she hesitated on the word 'whatever'.

We both decided to sit on the couch and watch some TV. She said she was feeling in a sexy mood (I of course was completely fine with this) so she turned on a romantic movie. Somewhere through the middle I could tell she was getting a little wet, as I was getting a half-hard-on. She said she was bored and we should go jump in the pool.

"I didn't bring a suit with me" I said, not knowing what to do.

"Just go in your boxers, there's no difference." She said, while stealing a glimpse at my shorts.

I immediately took up to this idea and took off my shorts and waited for her beside the pool. When she walked by, she was wearing an extremely skimpy pink and white Bikini.

"Go ahead, feel free to look" she said, noticing me somewhat staring at her in amazement.

"Sorry, couldn't help it" I said.

"No biggie, so you getting in or what?" she said.

"Well I know how your shy, so I'm taking you with me!" I said as I grabber her in a hug position, putting some pressure on her gorgeous sun-tanned ass. I took her and brought her in the pool with me. When we came up for air, we were both laughing very hard. I swam around for a bit and played with her like a little kid. At one point, I realized this was an opportunity to show my emotions. So Jokingly I squeezed her sides.

"Aah, stop it! hahaha" She said as she started giggling. I started to somewhat wrestle with her and at one point, I ended up in the corner on the steps with her in my lap. She was still laughing and hadn't really been bothered by it. I immediately started to get a raging hard-on.

"Looks like someone's enjoying themselves" she said as my prick pushed into her ass cheek.

"Sorry, I didn't.. I mean..." I said, not being able to come up with an excuse.

"It's okay, Chase. I kind of see it as a compliment" She said with a bit of a sexy tone. So that made me laugh and I began to grab and wrestle her a little bit more. Somehow in the midst of all this, her top came off and we both came up for air. I, of course, couldn't help but stare.

"Oh woops, hahaha, well stop staring!" She said trying to cover herself, although she didn't really look like she was trying too hard.

"Sorry, I can't help it, you have amazing boobs Jackie." I said, still staring.

"Well, it's okay. Listen, go inside and get yourself dried off, I think that is enough pool time for one night." She said.

I went back and dried myself off. I lost my shorts so she said I could borrow some oh her brothers. She handed me a pair of basketball shorts. This made me wonder. She came into the living room with just a pair of panties and a lingerie bra. This turned me on so much.

"It's okay right? I need to do some laundry" she said.

"Yeah of course!" I said, thinking about how much I wanted to fuck her.

"Hey do you wanna watch another movie?" she said teasingly.

"Yeah sure, sounds good to me" I said.

She put on a porn movie this time and about twenty minutes in, I noticed she was getting wet in her panties. I was so turned on, that my hard on stuck up through the shorts like a tent. She definitely noticed and took peeks at it. She took another look at the movie and asked, "So have you had sex yet?"

"Nope, just haven't had the chance with the right girl, you know." I said.

"Well do you ever think about who the right girl is or sex at all?" she said.

"All the time!" I said

"Well who do you imagine your first being." she said

Finally, this was the moment.

"Well, I always thought about doing it with you, Jackie."

She looked at me in wonder and then bit her lip.

"Well looks like it might be your lucky day." She said in the sexiest tone I have ever heard. "So what do you want to do?" She asked

"Jackie, I've wanted this for so long" I said as I held her and started to kiss her passionately. I felt the warmth of her moist tongue rubbing against mine. We kissed like that for minutes.

"Oh I've wanted this since last year, Chase!" She said.

I began to kiss her neck and at the same time, unstrapped her bra with one hand. I had been practicing for this moment.

I slowly moved down to her breast and began to circle around her nipples with my tongue.

"Ooooohhhh, Chaseee, that feels soooo good." She said, letting out soft moans every once in a while.

I continued to do this until I couldn't wait any longer. I laid her down and slipped off her panties, showing a perfectly shaven and wet pussy.

"Oh baby eat me, I want you down there so bad!" She said.

I immediately began to lick around and tease her clit. I was finding out what she liked and what she didn't by her large moans that she put out constantly. I then began to stick my tongue in and out and to finger fuck her.

"Oohhhh my gooodd, Chase, that feeelsss soooo gooood." she said.

"Oooh baby im bout to cum, don't stop licking that pussy. Keep on going! Don't Stop! OOOoohh GOOood!" She said as she jerked around harshly, letting all of her juice squeeze into my face. I was enjoying every second of it.

She finally settled down and said, "Now let me do you honey" with a large wink.

"I might not last that long the first time around" I said.

"Don't worry, I'll take good care of you." she said

She removed my shorts and boxers to reveal my 8-inch cock.

"It's so big! how does no girl want this?" she said

She immediately began to stroke it as she passionately kissed me. She moved her head farther and farther down until she slipped my head in and started to suck me.

"Oh my good that feels amazing!" I said with feelings of already pre-cum.

She continued to suck me hard and fondle with my balls for a few minutes until...

"Oh Jackie I'm about to cum!"

She continued to suck me until I couldn't hold it in any longer. I let out a massive load into her mouth and she licked every drop of it up.

"Now baby Lets get that dick hard again so you can fuck me." She said, letting my dick still for a bit and then teasing me by rubbing my hand on her pussy, It's silky warm feeling got me hard again pretty quick.

"Sorry if I'm really bad at this" I said, worried I won't be what she expects.

"Don't worry, you'll do just fine. Fuck me with that large cock baby, cmon, I want that inside me now."

I laid her down in her bedroom and positioned my cock right in front of her pussy. I stuck it in and I felt the most amazing feeling of excitement.

"Oh my god your pussy feels so good!" I said, feeling her from the inside.

I began to fuck her properly. I started with a slow rhythm and began to pick up the pace.

"Oh baby, that's it! Oooo give it to me, oh that feeeeels sooooo good. Don't stop!" She said as I continued to fuck her.

Her moans increased, as did mine, as we fucked for a straight 20 minutes. Finally I felt the cum getting ready to spurt.

"Oh Jackie I think I'm about to cum!"

"Oh baby so am I!"

I kept on fucking her, harder and harder.

"OOOH BABY DONT STOOOP. OH IT FEEELSSSSSS SOOO GOOD. OOH BABY IM SO CLOSE, I WANNA FEEL YOU CUM INSIDE ME. FILL ME UP BABY, CMON. HARDER, HARDER, HARDER, OH YESSSS!!" she said as both of us exploded in an intense orgasm.

I felt my hot cum fill her pussy up, as I felt her juicy liquid drench my dick. We just sat there in astonishment for a couple minutes. Finally Jackie said something.

"Oh my god that was the best sex I've ever had!"

"Are you sure it's gonna be okay that I came inside of you?" I asked

"Yeah, I'm on the pill." she said

"Oh ok good."

"So looks like you just found yourself the perfect girlfriend."

"So it looks like I have."

Thank you for reading, feel free to leave a comment on how I did. Thank you :)

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Comments(4)

hot2trott
Posted 21 Mar 2014 22:56
great story!
real69luvr
Posted 19 Jan 2014 13:30
I want Jackie as my best friend hahahhaa good story
Orgasmic
Posted 02 May 2011 23:44
Nicely written , next time be more descriptive about intimate details
Midnightlust
Posted 02 May 2011 23:29
One of the best first time stories i ever read! Defnitely 5 : )
 

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