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My First Time

"Andy finally sees the girl next door as more than just his best friend."

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I can remember it like it was yesterday, even though it’s been close to eight years ago. The summer between my junior and senior years of high school. A time when a boy my age has one thing on his mind. Sex!

I had been close friends with the girl next door since we were in diapers. Her name was Emily. She and I were in many ways best friends. Our part of the neighborhood was mostly older folks, so we were the only kids on the block. Growing up it helped that she was a bit of a tomboy. I guess since we had grown up so close, I had never realized that she had blossomed into such a beauty.

All of that changed on a summer's day in mind July. I was assigned some chores to do around the house by my parents while they were working. I figured it could be worse, since I was inside and in the air conditioning. While doing some cleanup in my room, I happened to look out the window; I had to do a double take. It’s when I had my epiphany, for on a lounge chair, soaking up the hot sun by the family pool was Emily.

Lying there, I didn't see my soccer playing tomboy friend. I was gazing at a brown haired, tight bodied sexpot with what looked like perfect C cup breasts, all covered by a barely-there bikini. I was transfixed. It was as if a light switch was flipped. I suddenly had a carnal desire. I must have looked out that window for a solid fifteen minutes, pawing at my growing cock through my pants. The fantasy playing out in my mind was interrupted by the ring of the telephone. Fucking telemarketer.

By the time I returned to my window, Emily had left her spot poolside. But not in my head. I reluctantly went back to my list of chores, which brought me outside. Just as I was finishing, I heard a familiar voice. Emily was along the fence, still in her bikini. We exchanged small talk while I did my best to hide my growing erection. My eyes wandered all over her, catching glimpses of her breasts, down to her legs, back to her toned stomach, up to her sexy smile, then her breasts again.

She asked if when I was done did I want to join her by the pool for a bit.

Did I? Of course I did! Now that I had woken to Emily's beauty, I wanted to be as close as possible to her. I told her I needed to freshen up and get into a bathing suit, but I'd be over. She told me to come get her in the house when I came over. I quickly headed in to my house and took a fast shower to clean all the dirt and sweat off of myself.

About fifteen minutes later, I was ready. Knocking and entering her place, I called out. Nothing. Not in the living room or kitchen. When I called out again, she responded.

She called me up to her room. I figured she was either on the phone or her computer talking to a girlfriend so I headed up.

Emily was lying on her bed, still in her bikini, book in hand. Putting the book aside she started talking. “You know, earlier I saw you at your window.”

Stammering, I tried denying it. Then she said something that changed everything. “Listen, its okay you were checking me out. To be honest, it’s about time.”

“Huh?” was all I could reply.

“I was starting to wonder if, ya know, if you were into guys. I’ve been taking notice of you for ages now.”

My cock was now stirring, straining against my swim shorts. “Seriously?” I asked, unsure if she was pulling a prank.

Beginning to get off the bed Emily said, “Yes, seriously. And I must say, your time on the soccer team has done you good.” Once she was on her feet, she convinced me she wasn’t pranking me. Reaching behind her back she untied her bikini top and let it fall to the floor, bringing my jaw with it.

My knees buckled a bit, as we stepped towards each other, our lips meeting. My hands found her breasts and massaged them. Breaking our kiss, Emily sank to her knees, her hands latching onto my shorts’ waistband. As she pulled them down, my sevenand a half inches sprang out and her eyes widened. Grasping at the base, Emily’s hand began to stroke me off.

Looking up at me with her big hazel eyes, she asked if I’d like it in her mouth. My head spinning, I looked down; shaking my head yes, all I could do was breathlessly sound out, “Uh-huh”.

Flicking her tongue out she licked around the head, she tilted my dick upwards and ran her tongue the length of the underside of my engorged cock from the tip to my balls and back. Then she enclosed the tip of my cock in between her lips and slowly drew it into her willing mouth. She continued to slide my cock in, until she reached the base. She had all of me, literally and figuratively.

Bobbing her head up and down, my dick passed in and out of her mouth, it was all I could do not to flood her mouth. She began to massage my balls and I latched onto her head with my hands and gently guided her along my cock. Before long, I was at the point of no return. My eyes closed, my muscles tensed, I held her head against me and lurched forward. Jet after jet of my cum shot into Emily’s sweet mouth. She instinctively pulled her head back, allowing all of my juice to pool in her mouth.

Spent, I slid my cock out, bringing with it, a strand of my cum which trailed onto Emily’s chin. Seductively, she looked up at me, winked, and gulped down my milk. Then she took her thumb, trailed it across her chin, and wiped away the remnants of my explosion.

Still not believing what had just happened, I helped Emily up, and we kissed again. Breaking the kiss, I pushed Em down onto her bed, allowing her legs to overhang. Dropping to the floor, I pulled her bikini bottoms off and uncovered a tight slit topped with a neatly manicured strip of trimmed hair.

Not really having any idea what to do, I began to rub the outer parts of her opening. Then I relied on what I had seen done in porn scenes. I took a finger and entered her, moving in and out. Then a second finger, prodding into her.  I lowered my face to her mound. Flicking my tongue out, I circled around her edges. Using her breathing and noises as a guide, I settled at the top. My tongue alternating between quick, darting motions and long strokes in and out. I pulled apart her lips and found her pearl. I began to gently massage it with my fingers.

“Oh fuck…that’s it right there…mmmm…Fuck yeah…Keep doing it right there…FASTER!...FASTER!”

Seeing her getting excited was having an affect on me as well. My cock began to stiffen as Em’s moans and gasps became louder and longer. I placed my mouth directly over her clit, and began licking and sucking for all I was worth. It was all she could take. Her legs slammed closed, trapping my head in place. She reached down, holding the top of my head tight to her, and she started to grind against me.

“Oh my God, I’m Cumming! Fuck, keep licking me …AAAGGGGHHHHHHHH! Yeah baby! That feels amazing!”

Like a river that didn’t know where it was flowing her juices were oozing out. I could taste and feel them coating my chin, tingling my taste buds. Her sweet nectar had gotten me fully hard again.

Joining her on the bed, I leaned in for a kiss. Our lips intertwined, sharing the remnants of her climax. “So you wanna fuck me now?” she asked.

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“What do you think?” was my simple, pointed reply. Giving my cock a few tugs I got into position, aligning myself with her pussy.

Just as I was about to break into the 'Promised Land' for the first time, Emily took a deep breath and said, “I’ve been waiting a couple years for this. Please be gentle, I have been saving myself for you.”

“Em, you should have said something. We could have been enjoying this a long time ago!” I said. “Don’t worry; I’ll let you take the lead on until you’re totally comfortable.”

I plopped onto her bed, laying flat. Emily flung her leg across me, straddling me. Grabbing hold of my dick, she guided me to her folds. I slipping inside as she slowly and gently began to lower herself on me.

It took all my self control to not grab hold of her hips and either force her down or thrust into her. We were both holding our breath. She gasped and whimpered a little as I broke through her virgin barrier. My arms wrapped behind her back and onto her hips, drawing her down towards me.

I whispered into her ear trying to reassure her, “Em, just relax, baby. If it hurts too much, we don’t have to do this.” She adjusted herself so we were eye to eye.

“I want this Andy. I’ve wanted this moment for too long now to turn back.” She raised herself up along my cock, then glided back down. Slowly at first, then gradually picking up pace until she had a nice rhythm. I adjusted my legs to better support her and to allow myself to meet her bouncing with thrusts of my own.

Not wanting to blow too early I pushed her Emily off and had her get on her hands and knees. Getting behind her, I grabbed hold of her ass, kneading it and then playfully smacking each cheek. I ran my cock up and down her pussy lips, not penetrating until she looked at me over her shoulder and said, “Will you stop fooling around and just fuck me already?”

I didn’t need to be asked twice. With one thrust, I was balls deep into Em. I started with long deliberate strokes, and then worked up some speed. Before long my cock was pumping into her from the tip to the base.  Emily breathlessly begged me to fuck her faster. I began to give her all I had, even if that meant not lasting as long as I wanted.

“C’mon baby, fuck me! Oh, your cock feels so big inside me… MMMMMMM... AAAHHHHHH… FUCK ME ANDY!” Emily knew just what to say to me.

I began to feel that familiar tightening and stirring in my balls. It wouldn’t be long now. Moving my hands from her hips to shoulders, I bucked into Emily a bit harder. I started to pull her back towards me until she was in a kneeling position. While still rocking into her, I embraced her and gently kissed her on the neck. With my free hand I used my fingers to rub her clit. My pace quickened,

“I’m gonna cum Em, where do you want it?”

Her reply sent me right to the edge. “I want to feel you explode inside me. Please cum inside me!”

With some final thrusts, I grabbed onto her tits and bottomed out, pulling her back into me. “Here it comes Em, OH FUCK! I’m cumming… AAGGGHH, my cock erupted. Spurting shot after shot into her pussy. I could feel Emily’s walls contract, and her juices flowing over me as she was also in the throws of her own orgasm.

We both collapsed onto her bed like a house of cards. Spent and fulfilled. After some recovery time, we curled up into each other. Out lips met and we shared a kiss. A new kiss. A kiss with a different feel. A different meaning. We had moved on from friends into something more.

Breaking the kiss, I asked, “So was that at least worth the wait?”

Giggling a bit, Emily said through a cheeky grin, “Oh, and then some. But you’ll have to make up for all that lost time.” I just smiled, knowing that wouldn’t be a problem.

 

**Author's Note**  This is my first attempt at writing a story of any kind. Feedback would be great, whether positive or negative. Also, names have been altered to respect privacy.

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Written by am1992
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